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for invention","granted":true,"earliest_filing_date":"1999-10-15","grant_date":"2003-08-19","anticipated_term_date":"2019-10-15","has_disclaimer":false,"patent_status":"EXPIRED","publication_count":2,"has_spc":false,"has_grant_event":true,"has_entry_into_national_phase":false},"abstract":{"en":[{"text":"\n Novel compounds of the pyridinium series useful for the management of diabetes and aging-related vascular and neurovascular complications, including kidney disease, nerve damage, atherosclerosis, retinopathy, inflammatory disorders, immunological disorders, oxidative stress, dermatological disorders and discoloration of teeth, by breaking preformed AGE, of the general formula I, or pharmaceutically acceptable salts thereof, \n\n wherein, R _{ 1 } , R _{ 2 } , R _{ 3 } , X and m are as defined in the specification. Also disclosed is a method for preparation of the compounds of general formula (I) and pharmaceutical composition containing one or more compounds as defined above as active ingredients. Also disclosed is a method of treatment of a diabetic patient by administering the compounds as defined above, either singly or in combination with drugs for antidiabetic therapy. \n","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"}]},"abstract_lang":["en"],"has_abstract":true,"claim":{"en":[{"text":"1. A compound represented by general formula (I), or a pharmaceutically acceptable salt thereof wherein","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"2. The compound as claimed in claim 1 , wherein C(O)R _{ 1 } group is at position 3 or 4.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"3. The compound as claimed in claim 2 , wherein the position for C(O)R _{ 1 } group is at position 3.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"4. The compound as claimed in claim 1 , wherein m is 0 or 1.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"5. The compound as claimed in claim 2 , wherein m is 0 or 1.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"6. The compound as claimed in claim 3 , wherein m is 0 or 1.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"7. The compound as claimed in claim 1 , wherein m is 0.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"8. The compound as claimed in claim 2 , wherein m is 0.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"9. The compound as claimed in claim 3 , wherein m is 0.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"10. The compound as claimed in claim 1 , wherein X is a halide ion.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"11. The compound as claimed in claim 1 , which is selected from the group consisting of the following compounds:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"12. The compound as claimed in claim 1 , which is selected from the group consisting of the following compounds:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"13. A process for the preparation of a compound represented by general formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof, which comprises providing a substituted pyridine having a backbone structure the same as the compound of general formula (I) or a pharmaceutically acceptable salt thereof that is to be prepared, followed by quaternizing the substituted pyridine with a quaternizing reagent in an alcoholic and/or high boiling solvent under reflux for 6-48 hrs. to give the desired compound represented by general formula (I) or a pharmaceutically acceptable salt thereof.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"14. A pharmaceutical composition comprising a pharmaceutically effective amount of one or more compounds represented by general formula (I), as defined in claim 1 or pharmaceutically acceptable salt(s) thereof in admixture with a pharmaceutically acceptable carrier, diluent, solvent or excepient.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"15. The pharmaceutical composition as claimed in claim 14 in the form of an oral formulation.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"16. The pharmaceutical composition as claimed in claim 14 , wherein said acceptable carrier, diluent, solvent or excepient is selected from group consisting of starch, lactose, polyvinyl pyrolidone (K-30), talc and magnesium stearate.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"17. The pharmaceutical composition as claimed in claim 14 in the form of a parenteral formulation.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"18. A method for the preparation of a parenteral formulation as claimed in claim 17 , which comprises dissolving one or more compounds represented by general formula (I), as defined in claim 1 or pharmaceutically acceptable salt(s) thereof, in polyethylene glycol 400 and diluting the solution so obtained with an isotonic solution or water to a desired concentration.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"19. The pharmaceutical composition as claimed in claim 14 in the form of a lotion, oral rinse and toothpaste.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"20. The pharmaceutical composition as claimed in claim 14 , wherein said compound is selected from the group consisting of:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"21. The pharmaceutical composition as claimed in claim 14 , wherein said compound is selected from the group consisting of:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"22. A method for treating a diabetic patient by breaking a preformed AGE, within said patient, which comprises, administering an effective amount of a compound represented by general formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof, either singly or in combination with other drugs for antidiabetic therapy.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"23. A method of preventing or treating diseases caused by diabetes and aging related complications including vascular and neuro-vascular complications, which comprises, administering to a patient in need thereof, an effective amount of a compound represented by general formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof, either singly or in combination with a pharmaceutically acceptable carrier, diluent or excepient.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"24. The method as claimed in claim 23 , wherein the disease prevented or treated is a nephrological disorder, neurological disorder, atherosclerosis, retinal disorder, dermatological disorder, non-enzymatic browning of oral cavity, endothelial or other organ dysfunction and growth impairment.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"25. The method as claimed in claim 23 , wherein the disease prevented or treated is an inflammatory disorder, immunological disorder, or oxidative stress.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"26. The method as claimed in claim 22 , wherein said compound is selected from the group consisting of:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"27. The method as claimed in claim 22 , wherein said compound is selected from the group consisting of:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"28. The method as claimed in claim 23 , wherein said compound is selected from the group consisting of:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"29. The method as claimed in claim 23 , wherein said compound is selected from the group consisting of:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"30. The process as claimed in claim 13 , wherein the substituted pyridine is selected from the group consisting of: and said quaternizing agent is selected from the group consisting of:","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"31. Pyridinium, 3-2-(ethoxycarbonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide or a pharmaceutically acceptable salt thereof.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"32. A pharmaceutical composition comprising a pharmaceutically effective amount of the compound as claimed in claim 31 or pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable carrier, diluent, solvent or excepient.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"33. The pharmaceutical composition as claimed in claim 32 in the form of an oral formulation.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"34. The pharmaceutical composition as claimed in claim 32 , wherein said acceptable carrier, diluent, solvent or excepient is selected from the group consisting of starch, lactose, polyvinyl pyrolidone (K-30), talc and magnesium stearate.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"35. The pharmaceutical composition as claimed in claim 32 , in the form of a parenteral formulation.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"36. A method for preparation of a parenteral formulation as claimed in claim 35 , which comprises dissolving pyridinium, 3-2-(ethoxycarbonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide or a pharmaceutically acceptable salt thereof in polyethylene glycol 400 and diluting the solution so obtained with an isotonic solution or water to a desired concentration.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"37. The pharmaceutical composition as claimed in claim 32 in the form of a lotion, oral rinse and toothpaste.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"38. A method for treating a diabetic patient by breaking a preformed AGE, within said patient, which comprises, administering an effective amount of the compound as claimed in claim 31 or pharmaceutically acceptable salt thereof, either singly, or in combination with other drugs for antidiabetic therapy.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"39. A method of preventing or treating diseases caused by diabetic and aging related complications including vascular and neuro-vascular complications which comprises administering to a patient in need thereof an effective amount of the compound as claimed in claim 31 or pharmaceutically acceptable salt thereof, either singly or in combination with a pharmaceutically acceptable carrier, diluent, solvent or excepient.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"40. The method as claimed in claim 39 , wherein the disease prevented or treated is a nephrological disorder, neurological disorder, atherosclerosis, retinal disorder, dermatological disorder, non-enzymatic browning of oral cavity, endothelial or other organ dysfunction and growth impairment.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"},{"text":"41. The method as claimed in claim 39 , wherein the disease prevented or treated is an inflammatory disorder, immunological disorder, or oxidative stress.","lang":"en","source":"USPTO_FULLTEXT","data_format":"ORIGINAL"}]},"claim_lang":["en"],"has_claim":true,"description":{"en":{"text":"\n BACKGROUND OF THE INVENTION \n\n 1. Field of the Invention \n\n The present invention relates to a new class of compounds of pyridinium series and to their use in treatment of diabetes and related illnesses. More particularly the invention relates to compounds of this series, methods for their preparation, pharmaceutical composition containing these compounds and their use in the treatment of complications of diabetes mellitus. The compounds of this series exhibit AGE breaking and inhibiting activity, which is essential for the treatment of diabetic and aging-related vascular and neurovascular complications including kidney disease, nerve damage, atherosclerosis, retinopathy, inflammatory disorders, immunological disorders, oxidative stress and dermatological conditions. The invention also extends to the method of reversing the discoloration of teeth resulting from nonenzymatic browning in the oral cavity which comprises administration of an amount effective to reverse pre-formed advanced glycosylation crosslinks. \n\n 2. Description of the Related Art \n\n Maillard in 1912 found that reducing sugars, such as glucose and ribose react with proteins to form brown pigments. Further studies have shown that this is an irreversible non-enzymatic reaction, which occurs in several natural systems including stored foodstuff. Maillard reaction occurs in two stages, early and advanced. Initially, proteins react with glucose to form stable Amadori products, which subsequently crosslinks to form advanced glycation end products (AGE). In most cases, the formation of AGE also accompanies browning of the proteins and increase in the fluorescence. \n\n In diabetes, where blood glucose level is significantly higher than normal, the reaction of glucose with several proteins such as haemoglobin, lens crystallin and collagen, gives rise to the formation of AGE, which in turn, is responsible for the complications associated with diabetes, such as nephropathy, microangiopathy, endothelial dysfunction and other organ dysfunctions. In addition, the activity of several growth factors, such as basic fibroblast growth factor, is also impaired. AGE products, unlike normal proteins in tissue, have a slower rate of turnover and replenishment. It has been reported that AGE products may in fact elicit a complex immunological reaction involving RAGE (Receptor for Advanced Glycation End Products) receptors and activation of several incompletely defined immunological processes. It has been documented that diabetes with evidence of microangiopathy and macroangiopathy also show evidence of oxidative stress, the mechanism of which has not been elucidated. \n\n In vitro AGE formation can be studied in the laboratory by incubating reducing sugars, such as ribose or glucose with bovine serum albumin. AGE formation can be detected by increase in the fluorescence or increased cross reactivity with anti-AGE antibodies. The increase in fluorescence seems to precede formation of AGE specific antigenic epitopes. This increase in fluorescence is used to monitor the increased AGE formation in vitro (Brownlee M et al, Science 1986; 232:1629-1632). In addition to the increase in the fluorescence, one of the most important features of in vitro AGE formation is the formation of antigenic epitopes that are specific to AGE and not to the native proteins. Therefore, it is possible to raise antibodies against advanced glycation end products of one protein and use them to detect AGE formation in other proteins. This has served as an important analytical tool in AGE research. \n\n Due to the clinical significance of AGE formation, many approaches are being used to diagnose, prevent, or revert AGE formation in the body. The formation of AGE could be inhibited by reacting with an early glycosylation product that results from the original reaction between the target protein and glucose. The inhibition was believed to take place as the reaction between the inhibitor and the early glycosylation product appeared to interrupt the subsequent reaction of the glycosylated protein with additional protein material to form the cross linked late stage product. Compounds like aminoguanidine act to inhibit AGE formation by such mechanism. \n\n The formation of AGE on long-lived proteins is also associated with cross-linking of these proteins. The AGE derived protein cross-links have been shown to be cleaved by compounds like N-phenacyl thiazolium bromide (PTB), which reacts with and cleaves covalent, AGE derived protein cross links (Vasan et al. Nature 1996; 382: 275-278; U.S. Pat. No. 5,853,703, Date of Patent: Dec. 29, 1998). The mechanism of reducing the AGE content in tissues is expected to take place relatively rapidly, in contrast to aminoguanidine, which acts slowly by its very nature of mechanism of action. This current specification is related to compounds of pyridinium class, which break pre-formed AGE, like PTB, and in some cases even more effectively by than PTB. \n\n SUMMARY OF THE INVENTION \n\n The main objective of the present invention is to provide a new class of compounds of the pyridinium series which are useful for the management of diabetes and aging related vascular and neurovascular complications and particularly in the treatment of complications of diabetes mellitus and other aging related conditions including kidney disease, nerve damage, atherosclerosis, retinopathy, inflammatory disorders, immunological disorders, oxidative stress and dermatological conditions. The invention also extends the method to reverse the discoloration of teeth resulting from nonenzymatic browning in the oral cavity which comprises administration of an amount effective to reverse the pre-formed advanced glycosylation crosslinks, etc. \n\n Another object of the present invention is to provide compounds of the pyridinium series, which exhibit AGE breaking activities. \n\n Yet another object of the present invention is to provide a method of preparation of compounds of the pyridinium series which exhibit AGE breaking activities. \n\n Still another object of the invention is to provide pharmaceutical compositions with a new class of compounds of the pyridinium series according to the invention and their pharmaceutically acceptable salts in combination with suitable carriers, solvents, excepients, diluents and other media normally employed in preparing such compositions. \n\n Still another object of the invention is to provide a method of treatment of a diabetic patient by administration of the compounds of the invention, either singly or in combination with drugs for anti-diabetic therapy, or pharmaceutically acceptable salts thereof in required dosage in admixture with pharmaceutically acceptable diluent, solvent, excepients, carriers or other media as may be appropriate for the purpose. \n\n\n DETAILED DESCRIPTION OF THE INVENTION \n\n The present invention provides for a new class of AGE breakers, of general formula I, \n\n wherein \n\n R _{ 1 } is R _{ 4 } R _{ 5 } or N(R _{ 7 } ) N (R _{ 7 } ) R _{ 9 } ; \n\n R _{ 4 } is selected from the group consisting of N(R _{ 7 } )R _{ 6 } O, N(R _{ 7 } )R _{ 6 } N(R _{ 7 } ), OR _{ 6 } O, and OR _{ 6 } N(R _{ 7 } ), where R _{ 6 } is alkyl with C _{ 2 } to C _{ 8 } carbon atoms; \n\n R _{ 5 } is selected from the group consisting of alkyl, aryl including heteroaryl, COR _{ 7 } , SO _{ 2 } R _{ 7 } , C(S)NHR _{ 7 } , C(NH)NHR _{ 7 } , COR _{ 10 } , \n\n where R _{ 7 } is selected from the group consisting of H, alkyl and aryl including heteroaryl provided R _{ 7 } may be the same or different for R _{ 1 } and R _{ 3 } in the same compound; \n\n R _{ 2 } is selected from the group consisting of F, Cl, Br, I, OR _{ 7 } , NO _{ 2 } , alkyl, aryl including heteroaryl, formyl, acyl, C(O)NR _{ 7 } R _{ 10 } , C(O)OR _{ 7 } , NR _{ 7 } R _{ 10 } , NC(R _{ 7 } )(R _{ 10 } ), SR _{ 7 } , SO _{ 2 } NH _{ 2 } , SO _{ 2 } alkyl and SO _{ 2 } aryl, and m is 0, 1 or 2; \n\n R _{ 3 } is selected from the group consisting of R _{ 7 } , OR _{ 7 } , N(R _{ 7 } )(R _{ 10 } ), NC(R _{ 7 } )(R _{ 10 } ), N(R _{ 7 } )N(R _{ 7 } )(R _{ 10 } ), N(R _{ 7 } )NC(R _{ 7 } )(R _{ 10 } ) and CH(R _{ 7 } )C(O)R _{ 8 } where R _{ 8 } is selected from the group consisting of R _{ 7 } , OR _{ 7 } and NR _{ 7 } R _{ 10 } ; \n\n R _{ 9 } is selected from the group consisting of hydrogen, alkyl, aryl including heteroaryl, C(O)R _{ 10 } , SO _{ 2 } R _{ 10 } , C(S)NHR _{ 10 } , C(NH)NH(R _{ 10 } ) and C(O)NHR _{ 10 } ; \n\n R _{ 10 } is selected for the group consisting of H, alkyl or aryl including heteroaryl and in each case may be the same or different from substituent R _{ 7 } , provided R _{ 10 } may be the same or different for R _{ 1 } and R _{ 3 } in the same compound; \n\n X is selected from group consisting of a halide ion, acetate ion, perchlorate ion, sulfonate ion, oxalate ion, citrate ion, tosylate ion, maleate ion, mesylate ion, carbonate ion, sulfite ion, phosphoric hydrogen ion, phosphonate ion, phosphate ion, BF _{ 4 } ^{ } and PF _{ 6 } ^{ } ; with proviso that, \n\n (i) when two alkyl groups are present on the same carbon or nitrogen, they may be linked together to form a cyclic structure and \n\n (ii) the nitrogen of heteroaryl ring of R _{ 10 } , when present, may be quaternized with compound such as XCH _{ 2 } C(O)R _{ 3 } . \n\n In a preferred embodiment, (iii) R _{ 3 } is OR _{ 7 } and R _{ 1 } is NHNH _{ 2 } then R _{ 7 } is not alkyl, and (iv) when R _{ 3 } is OR _{ 7 } , R _{ 1 } is N(R _{ 7 } )(NR _{ 7 } )R _{ 9 } and R _{ 9 } is C(O)R _{ 10 } where R _{ 10 } is alkyl, then R _{ 7 } is not hydrogen. \n\n As used herein, alkyl refers to an optionally substituted hydrocarbon group joined by single carbon-carbon bonds and having 1 to 8 carbon atoms joined together. The alkyl hydrocarbon group may be linear, branched or cyclic, saturated or unsaturated. The substituents are selected from F, Cl, Br, I, N, S, O and aryl. Preferably, no more than three substituents are present. \n\n As used herein aryl refers to an optionally substituted aromatic group with at least one ring having a conjugated pi-electron system, containing up to two conjugated or fused ring systems. Aryl includes carbocyclic aryl, heterocyclic aryl and biaryl groups, all of which may be optionally substituted. The substituents are selected from F, Cl, Br, I, N, O, S and straight chain or branched C _{ 1 } -C _{ 6 } hydrocarbon. The substituents for the aryl group are preferably selected from F, Cl, Br, I, N, O and straight chain or branched C _{ 1 } -C _{ 6 } hydrocarbon. \n\n The novel compounds of the invention of general formula I having m as 0 or 1 and COR _{ 1 } at position 3 are listed in Table 1A and the novel compounds of the invention of general formula I having m as 0 and COR _{ 1 } at position 4 are listed in Table 1B. The following compounds suggested are by way of example alone of the representative compounds of the general formula I as defined above and in no way restrict the invention: \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-(2-oxo-2-phenylethyl)-, dibromide (Compound No. 1) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-(2-ethoxy-2-oxoethyl)-, dibromide (Compound No.2) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(2,4-dichlorophenyl)-2-oxoethyl-, dibromide (Compound No.3) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)- 3 -2-(2-pyridinyl)hydrazinocarbonyl-, bromide (Compound No.4) \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No.5) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-oxo-2-(2-thienyl)ethyl-, dibromide (Compound No.6) \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-(2-ethoxy-2-oxoethyl)-, bromide (Compound No.7) \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-2-(2,4-dichlorophenyl)-2-oxoethyl-, bromide (Compound No.8) \n\n Pyridinium, 1-2-oxo-2-(2-thienyl)ethyl-3-2-(2-pyridinyl)hydrazinocarbonyl-, bromide (Compound No.9) \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-2-(2-pyridinyl)hydrazinocarbonyl-, bromide (Compound No.10) \n\n Pyridinium, 3-(hydrazinocarbonyl)-1-(2-oxo-2-phenylethyl)-, bromide (Compound No. 11) \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No.12) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(methylsulfonyl)hydrazinocarbonyl-, bromide (Compound No.13) \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound No.14) \n\n Pyridinium, 2-chloro-1-(2-oxo-2-phenylethyl)-3-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound No.15) \n\n Pyridinium, 3-2-(acetyloxy)ethoxycarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No.16) \n\n Pyridinium, 3-2-(benzoyloxy)ethoxycarbonyl-1-(2-ethoxy-2-oxoethyl)-, bromide (Compound No.17) \n\n Pyridinium, 4-2-(benzoyloxy)ethylaminocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No.18) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-4-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound No. 19) \n\n Pyridinium, 1-2-oxo-2-(phenylamino)ethyl-4-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound No.20) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(phenlysulfonyl)hydrazinocarbonyl-, bromide (Compound No.21) \n\n Pyridinium, 1-2-(2,4-dichlorophenyl)-2-oxoethyl-3-(2-methoxyethoxy)carbonyl-, bromide (Compound No.22) \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-2-oxo-2-(phenylamino)ethyl-, chloride (Compound No.23) \n\n Pyridinium, 1-2-oxo-2-(2-thienyl)ethyl-3-2-(phenylamino)carbonylhydrazinocarbonyl-, bromide (Compound No.24) \n\n Pyridinium, 3-2-(acetyloxy)ethylaminocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No.25) \n\n Pyridinium, 1-2-oxo-2-(phenylamino)ethyl-3-2-(phenylsulfonyl)hydrazinocarbonyl-, chloride (Compound No.26) \n\n Pyridinium, 3-2-(4-methylphenyl)sulfonylhydrazinocarbonyl-1-2-oxo-2-(phenylamino)ethyl-, chloride (Compound No.27) \n\n Pyridinium, 3-2-(benzoyloxy)ethoxycarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No.28) \n\n Pyridinium, 3-(2-benzoylhydrazino)carbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No.29) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(phenylmethyl)sulfonylhydrazinocarbonyl-, bromide (Compound No.30) \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-2-(phenylmethyl)sulfonylhydrazinocarbonyl-, bromide (Compound No.31) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(2-furanyl)-2-oxoethyl-, dibromide (Compound No. 32) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(2-thienyl)-2-oxoethyl-, dichloride (Compound No. 33) \n\n Pyridinium, 3-2-(3-cyclohexyl-1-oxopropyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No. 34) \n\n Pyridinium, 3-2-(3-cyclohexyl-1-oxopropyl)hydrazinocarbonyl-1-2-oxo-2-(phenylamino)ethyl-, chloride (Compound No. 35) \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No. 36) \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-(4-ethoxy-2,4-dioxobutyl)-, chloride (Compound No. 37) \n\n Pyridinium, 3-(2-methoxyethyl)aminocarbonyl-1-2-(2,4-dichlorophenyl)-2-oxoethyl-, bromide (Compound No. 38) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(cyclopropylamino)-2-oxoethyl-, dichloride(Compound No. 39) \n\n Pyridinium, 1-2-(cyclopropylamino)-2-oxoethyl-3-(2-methoxyethyl)aminocarbonyl-, chloride (Compound No. 40) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(1-methylethyl)amino-2-oxoethyl-, dichloride (Compound No. 41) \n\n Pyridinium, 3-2-(2-chloro-3-pyridinyl)carbonylhydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, chloride (Compound No. 42) \n\n Pyridinium, 1-2-(1-methylethyl)amino-2-oxoethyl-3-2-(methylsulfonyl)hydrazinocarbonyl-, chloride (Compound No. 43) \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(1-pyrrolidinyl)ethyl-, chloride (Compound No. 44) \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, chloride (Compound No. 45) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-(carboxymethyl)-, dichloride (Compound No. 46) \n\n Pyridinium, 3-bromo-5-2-methoxyethyl)aminocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, chloride (Compound No. 47) \n\n Pyridinium, 3-2-6-(methoxycarbonyl)-3-pyridinylcarbonylhydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, chloride (Compound No. 48) \n\n Pyridinium, 2-methyl-1-(2-oxo-2-thien-2-yl-ethyl)-5-2-1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-ylcarbonylhydrazinocarbonyl-, dichloride (Compound No. 49) \n\n Pyridinium, 3-2-(1-methylethyl)sulfonylhydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No. 50) \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-4-(phenylmethyl)-1-piperidinylethyl-, chloride (Compound No. 51) \n\n Pyridinium, 1-2-2-(ethoxycarbonyl)-1-pyrrolidinyl-2-oxoethyl-3-2-(methylsulfonyl)hydrazinocarbonyl-, chloride (Compound No. 52) \n\n Pyridinium, 3-bromo-5-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No. 53) \n\n Pyridinium, 3-2-(ethoxycarbonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No. 54) \n\n Pyridinium, 1-2-(5-chloro-2-thienyl)-2-oxoethyl-3-2-(methylsulfonyl)hydrazinocarbonyl-, bromide (Compound No. 55) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(4-nitro-2-thienyl)-2-oxoethyl-, dichloride (Compound No. 56) \n\n Pyridinium, 2-methyl-5-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No. 57) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(5-methyl-2-thienyl)-2-oxoethyl-, dichloride (Compound No. 58) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-2-(ethoxy carbonyl)-1-pyrrolidinyl-2-oxoethyl-, dichloride (Compound No. 59) \n\n Pyridinium, 3-(aminocarbonyl)-1-(2-oxo-2-thien-2-yl-ethyl)- -5 -2-1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-ylcarbonylhydrazinocarbonyl-, dichloride (Compound No. 60) \n\n Pyridinium, 1-2-4-(ethoxycarbonyl)-3-thiazolidinyl-2-oxoethyl-3-2-(methylsulfonyl)hydrazinocarbonyl-, chloride (Compound No. 61) \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(5-chloro-2-thienyl)-2-oxoethyl-, dichloride (Compound No. 62) \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-(5-methyl-2-thienyl)-2-oxoethyl-, chloride (Compound No. 63) \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-(4-nitro-2-thienyl)-2-oxoethyl-, bromide (Compound No. 64) \n\n Pyridinium, 1-2-oxo-2-(phenylamino)ethyl-3-(2-phenylhydrazino)carbonyl-, chloride(Compound No. 65) \n\n Pyridinium, 4-2-(benzoyloxy)ethylaminocarbonyl-1-2-oxo-2-(phenylamino)ethyl-, chloride (Compound No. 66) \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-(5-nitro-2-thienyl)-2-oxoethyl-, chloride (Compound No. 67) \n\n Pyridinium, 1-2-oxo-2-(2-thienyl)ethyl-3-2-(trifluoromethyl)sulfonylhydrazinocarbonyl-, bromide (Compound No. 68) \n\n Pyridinium, 1-2-oxo-2-(2-thienyl)ethyl-3-(2-phenylhydrazino)carbonyl-, bromide (Compound No. 69) \n\n Pyridinium, 3-2-(4-methoxyphenyl)sulfonylhydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No. 70) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(phenylamino)carbonylhydrazinocarbonyl-, bromide (Compound No. 71) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(4-methylphenyl)sulfonylhydrazinocarbonyl-, bromide (Compound No. 72) \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-2-(phenylamino)carbonylhydrazinocarbonyl-, bromide (Compound No.73) \n\n Pyridinium, 1-2-oxo-2-(phenylamino)ethyl-3-2-(phenylmethyl)sulfonylhydrazinocarbonyl-, chloride (Compound No. 74) \n\n Pyridinium, 4-2-(methylsulfonyl)hydrazinocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No. 75) \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-(2-phenylhydrazino)carbonyl-, bromide (Compound No. 76) \n\n Pyridinium, 4-2-(benzoyloxy)ethylaminocarbonyl-1-(2-ethoxy-2-oxoethyl)-, bromide (Compound No. 77) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-(2-phenylhydrazino)carbonyl-, bromide (Compound No. 78) \n\n Pyridinium, 3-2-(4-methoxyphenyl)sulfonylhydrazinocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No. 79) \n\n Pyridinium, 4-2-(benzoyloxy)ethylaminocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No. 80) \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-4-2-(methylsulfonyl)hydrazinocarbonyl-, bromide (Compound No. 81) \n\n In place of specific halide salts of the compounds listed above, these compounds may also be in the form of other pharmaceutically acceptable salts falling within the definition of X as given above. The words and pharmaceutically acceptable salts thereof as used herein following the names of specific compounds of general formula (I) of the invention means that such compounds encompass other pharmaceutically acceptable salts falling within. the definition of X. \n\n\n TABLE 1A \n\n Representative Pyridinium derivatives \n (having m as 0 or 1 and COR _{ 1 } at position 3) \n\n\n Com- \n pound R _{ 1 } R _{ 2 } R _{ 3 } X \n\n 1 Structure (a) phenyl Br \n 2 Structure (b) OEt Br \n 3 Structure (c) 2,4-dichlorophenyl Br \n 4 NHNH-(2-pyridyl) OEt Br \n 5 NHNHSO _{ 2 } CH _{ 3 } 2-thienyl Br \n 6 Structure (d) 2-thienyl Br \n 7 NHCH _{ 2 } CH _{ 2 } OCOPh OEt Br \n 8 NHCH _{ 2 } CH _{ 2 } OCOPh 2,4-dichlorophenyl Br \n 9 NHNH-(2-pyridyl) 2-thienyl Br \n 10 NHNH-(2-pyridyl) phenyl Br \n 11 NHNH _{ 2 } phenyl Br \n 12 NHNHSO _{ 2 } CH _{ 3 } phenyl Br \n 13 NHNHSO _{ 2 } CH _{ 3 } OEt Br \n 14 NHNH-SO _{ 2 } phenyl phenyl Br \n 15 NHNH-SO _{ 2 } phenyl 2-Cl phenyl Br \n 16 OCH _{ 2 } CH _{ 2 } OCOCH _{ 3 } phenyl Br \n 17 OCH _{ 2 } CH _{ 2 } OCOPh OEt Br \n 21 NHNHSO _{ 2 } Ph OEt Br \n 22 OCH _{ 2 } CH _{ 2 } OCH _{ 3 } 2,4-dichlorophenyl Br \n 23 NHCH _{ 2 } CH _{ 2 } OCOPh NH phenyl CI \n 24 NHNHCONHPh 2-thienyl Br \n 25 NHCH _{ 2 } CH _{ 2 } OCOCH _{ 3 } phenyl Br \n 26 NHNHSO _{ 2 } Ph NH phenyl CI \n 27 NHNHSO _{ 2 } Ph(4-CH _{ 3 } ) NH phenyl CI \n 28 OCH _{ 2 } CH _{ 2 } OCOPh phenyl Br \n 29 NHNHCOPh 2-thienyl Br \n 30 NHNHSO _{ 2 } CH _{ 2 } Ph OEt Br \n 31 NHNHSO _{ 2 } CH _{ 2 } Ph phenyl Br \n 32 Structure (e) 2-furyl Br \n 33 Structure-(f) 2-thienyl Cl \n 34 NHNHCOCH _{ 2 } CH _{ 2 } - 2-thienyl Br \n cyclohexyl \n 35 NHNHCOCH _{ 2 } CH _{ 2 } - NH-phenyl Cl \n cyclohexyl \n 36 NHCH _{ 2 } CH _{ 2 } OCO- 2-thienyl Br \n phenyl \n 37 NHCH _{ 2 } CH _{ 2 } OCO- CH _{ 2 } CO _{ 2 } -ethyl Cl \n phenyl \n 38 NHCH _{ 2 } CH _{ 2 } OCH _{ 3 } -2,4-dichlorophenyl Br \n 39 Structure-(g) NH-cyclopropyl Cl \n 40 NHCH _{ 2 } CH _{ 2 } OCH _{ 3 } NH-cyclopropyl Cl \n 41 Structure-(h) NH-isopropyl Cl \n 42 Structure-(i) 2-thienyl Cl \n 43 NHNHSO _{ 2 } CH _{ 3 } NH-isopropyl Cl \n 44 NHNHSO _{ 2 } CH _{ 3 } 1-pyrrolidinyl Cl \n 45 NHNHSO _{ 2 } CH _{ 3 } 2-thienyl Cl \n 46 Structure-(j) OH Cl \n 47 NHCH _{ 2 } CH _{ 2 } OCH _{ 3 } 3-bromo 2-thienyl Cl \n 48 Structure-(k) 2-thienyl Cl \n 49 Structure-(l) 2-thienyl Cl \n 50 NHNHSO _{ 2 } isopropyl 2-thienyl Br \n 51 NHNHSO _{ 2 } CH _{ 3 } Structure (m) Cl \n 52 NHNHSO _{ 2 } CH _{ 3 } Structure (n) Cl \n 53 NHNHSO _{ 2 } CH _{ 3 } 3-bromo 2-thienyl Br \n 54 NHNHCOC _{ 2 } H _{ 5 } 2-thienyl Br \n 55 NHNHSO _{ 2 } CH _{ 3 } 5-chloro-2-thienyl Br \n 56 Structure (o) 4-nitro-2-thienyl Cl \n 57 NHNHSO _{ 2 } CH _{ 3 } 2-methyl 2-thienyl Br \n 58 Structure (p) 5-methyl-2-thienyl Cl \n 59 Structure (q) Structure (n) Cl \n 60 Structure (r) 2-thienyl Cl \n 61 NHNHSO _{ 2 } CH _{ 3 } Structure (s) Cl \n 62 Structure (t) 5-chloro-2-thienyl Cl \n 63 NHNHSO _{ 2 } CH _{ 3 } 5-methyl-2-thienyl Cl \n 64 NHNHSO _{ 2 } CH _{ 3 } 4-nitro-2-thienyl Br \n 65 NHNHPh NHPh Cl \n 67 NHNHSO _{ 2 } CH _{ 3 } 5-nitro-2-thienyl Cl \n 68 NHNHSO _{ 2 } CF _{ 3 } 2-thienyl Br \n 69 NHNHPh 2-thienyl Br \n 70 NHNHSO _{ 2 } -4- 2-thienyl Br \n methoxy-Phenyl \n 71 NHNHCONHPh OEt Br \n 72 NHNHSO _{ 2 } -4- OEt Br \n methyl-Phenyl \n 73 NHNHCONHPh Ph Br \n 74 NHNHSO _{ 2 } CH _{ 2 } Ph NHPh Cl \n 76 NHNHPh Ph Br \n 78 NHNHPh OEt Br \n 79 NHNHSO _{ 2 } -4- Ph Br \n methoxy-Phenyl \n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n TABLE 1B \n\n Representative Pyridinium derivatives \n (having m as 0 and COR _{ 1 } at position 4) \n Compound R _{ 1 } R _{ 2 } R _{ 3 } X \n\n 18 NHCH _{ 2 } CH _{ 2 } OCOPh 2-thienyl Br \n 19 NHNHSO _{ 2 } Ph OEt Br \n 20 NHNHSO _{ 2 } Ph NH phenyl CI \n 66 NHCH _{ 2 } CH _{ 2 } OCOPh NHPh CI \n 75 NHNHSO _{ 2 } CH _{ 3 } Ph Br \n 77 NHCH _{ 2 } CH _{ 2 } OCOPh OEt Br \n 80 NHCH _{ 2 } CH _{ 2 } OCOPh Ph Br \n 81 NHNHSO _{ 2 } CH _{ 3 } OEt Br \n\n\n According to the embodiment of the present invention, the present compounds are used for the treatment of diabetic complications, and aging related vascular and neurovascular complications including kidney disease, nerve damage, atherosclerosis, retinopathy, inflammatory discorders, immunological disorders, oxidative stress, dermatological conditions, and cosmetic conditions including colouration of teeth occurring due to the higher levels of preformed AGE. The increased levels of preformed AGE can be brought under control by breaking the AGE products using compounds mentioned in the invention. \n\n The invention also provides a process for the preparation of novel compounds of the pyridinium series. \n\n The said process for the preparation of compound 1, comprises, adding a solution of phenacyl bromide in isopropanol to N,N-bis(nicotinyl)hydrazine dissolved in methanol, refluxing for six hours, cooling, filtering the precipitated solid, washing the solid with hot ethyl acetate and finally purifying the solid with 20 ml of methanol ethyl acetate (3:1) to yield the desired compound. \n\n Similarly, the other novel compounds of general formula I, are prepared from properly substituted pyridine derivatives followed by quarternization with appropriate reagent by refluxing in alcoholic solvents like, methanol, ethanol, propanol, etc and high boiling solvents like toluene or xylene etc, for 6-48 hrs. to give the desired compounds. \n\n The examples of substituted pyridine derivatives which can be used for preparation of specific compounds of the invention are given below: \n\n 1. N,N-bis(nicotinyl)hydrazine \n\n 2. 3-(2-pyridyl)hydrazinocarbonylpyridine \n\n 3. 3-2-methanesulfonyl)hydrazinocarbonylpyridine \n\n 4. 3-(2-benzoyloxy)ethylaminocarbonylpyridine \n\n 5. 3-(2-phenylsulfonyl)hydrazinocarbonylpyridine \n\n 6. 3-(2-acetoxy)ethyloxycarbonylpyridine \n\n 7. 3-(2-benzoyloxy)ethyloxycarbonylpyridine \n\n 8. 3-(2-methoxy)ethyloxycarbonylpyridine \n\n 9. 3-(2-phenylaminocarbonyl)hydrazinocarbonylpyridine \n\n 10. 3-(2-acetoxy)ethylaminocarbonylpyridine \n\n 11. 3-(2-(4-methylphenyl sulfonylhydrazinocarbonyl))pyridine \n\n 12. 3-(2-benzoyl)-hydrazinocarbonylpyridine \n\n 13. 3-(2-phenylmethane sulfonyl)hydrazino carbonylpyridine \n\n 14. 3-(2-(3-cyclohexylpropanoyl)hydrazino carbonylpyridine \n\n 15. 3-(2-methoxy)ethylaminocarbonylpyridine \n\n 16. 3-1-oxo-1-(2-methoxycarbonyl)pyridylhydrazino pyridine \n\n The examples of quaternizing agents which may be used in the reaction are given below: \n\n 1. 2-bromoacetyl thiophene \n\n 2. 2-chloroacetyl thiopene \n\n 3. phenacylbromide \n\n 4. phenacylchloride \n\n 5. 2,4-dichloropheanacylbromide \n\n 6. N-phenyl chloroacetamide \n\n 7. N-cyclopropyl chloroacetamide \n\n 8. ethylbromoacetate \n\n 9. bromo acetylfuran \n\n 10. N-isopropylchloroacetamide \n\n 11. N-chloroacetyl-2-pyrrolidinone \n\n 12. chloroacetic acid \n\n In-vitro Screening for AGE-breaking Activity \n\n The in vitro AGE formation, studied in the laboratory, by incubating reducing sugar glucose, with protein bovine serum albumin, resulted in browning of solution and increase in the fluorescence. Fluorescence was used as the criteria to monitor the increased AGE formation. \n\n EXAMPLE 1 \n\n AGE breaker Activity has been Confirmed by the Screening Procedure as Mentioned Below \n\n Materials \n\n Bovine serum albumin (fraction V) (BSA) \n\n Glucose, analytical grade \n\n Phosphate buffered saline (PBS) \n\n Equipment \n\n Microplate ELISA ReaderSpectramax Plus (Molecular Devices, USA) \n\n Microplate washer, (Bio-Tec Instruments, USA) pH meter \n\n Methods of Experiment \n\n Elisa (Enzyme Linked Immunosorbent Assay) 160 mg/ml of protein, bovine serum albumin, BSA and 1.6M glucose sugar were dissolved in phosphate buffered saline, PBS. Sodium azide was added at 0.02% concentration as a preservative. The solution was filtered asceptically through a 0.22 M filter and kept for aging at 37 C. for 16 weeks. After 16 weeks the solution was dialyzed against PBS, aliquoted and stored at 20 C. \n\n To determine the AGE breaking activity, 10 g/ml of the 16 weeks AGE-BSA was incubated with different concentrations of the test compounds at 37 C. for 24 hours and AGE breaking activity of the test compounds by ELISA was determined. \n\n ELISA was Performed as Follows \n\n 1. Different concentrations of 16 weeks AGE-BSA were coated on a microtitre plate as standard. Each concentration is coated in triplicates. \n\n 2. The test samples were coated on microtitre plate at a concentration of 5 ng. to 20 ng per well in triplicates. \n\n 3. The plate was incubated at 37 C. for one hour. \n\n 4. After incubation the plate was washed with PBST (PBS with 0.05% Tween 20). \n\n 5. Blocking with 5% skimmed milk in PBS at 37 C. for one hour was done. \n\n 6. The plate was washed with PBST. \n\n 7. Primary antibody against AGE-BSA was added and the plate is incubated at 37 C. for one hour. \n\n 8. The plate was washed with PBST \n\n 9. Secondary antibody anti rabbit HRPO (Horse-Radish Per Oxidase) conjugate was added and the plate is incubated at 37 C. for one hour. \n\n 10. The plate was washed with PBST. \n\n 11. Colour development with OPD (orthophenylenediamine dihydrochloride) and hydrogen peroxide was done. \n\n 12. OD (optical density) at (450 nm reading-620 nm reading) was measured after incubation at 37 C. for 15 minutes with Microplate ELISA Reader. \n\n The breaker activity of the compounds were determined by the following formula: % Breaker activity = OD 450 - 620 Control - OD 450 - 620 Test OD 450 - 620 Control 100 \n\n OD _{ 450-620 } ControlAbsorbance of 20 ng AGE-BSA after incubation at 37 C. for 24 hours without test compound \n\n OD _{ 450-620 } TestAbsorbance of 20 ng AGE-BSA after incubation at 37 C. for 24 hours with required concentration of test compound Using specific examples, the % AGE breaking activity was calculated and recorded in Table 2. \n\n\n TABLE 2 \n\n Sample Concentration % Breakage \n\n\n PTB 10 mM 27 \n 20 mM 47 \n Compound 1 5 mM 13 \n Compound 4 10 mM 30 \n Compound 5 10 mM 16 \n 50 mM 68 \n Compound 6 5 mM 53 \n Compound 7 20 mM 36 \n Compound 16 10 mM 16 \n Compound 17 10 mM 19 \n Compound 22 10 mM 13 \n 25 mM 41 \n Compound 23 10 mM 37 \n 25 mM 90 \n Compound 32 10 mM 14 \n Compound 33 5 mM 20 \n Compound 38 5 mM 17.66 \n Compound 39 5 mM 22.8 \n Compound 40 10 mM 12.38 \n Compound 42 10 mM 12.51 \n Compound 43 10 mM 10.85 \n Compound 45 10 mM 17.53 \n Compound 47 10 mM 32.38 \n Compound 49 2.5 mM 85.67 \n Compound 50 10 mM 31.45 \n Compound 51 10 mM 20.94 \n Compound 52 10 mM 25.34 \n Compound 53 2.5 mM 29.36 \n Compound 54 10 mM 33.43 \n Compound 55 10 mM 40.85 \n Compound 56 10 mM 75.92 \n Compound 57 1.0 mM 77.69 \n Compound 58 10 mM 81.95 \n Compound 59 10 mM 20.31 \n Compound 60 1 mM 95.36 \n Compound 61 10 mM 25.06 \n Compound 62 10 mM 78.41 \n Compound 63 10 mM 25.17 \n Compound 64 10 mM 60.94 \n Compound 65 2.5 mM 68.35 \n Compound 66 10 mM 19.07 \n Compound 67 1 mM 42.01 \n Compound 68 10 mM 92.64 \n\n\n Hence compounds 4,6, 23,33,39, 47, 49, 50, 53-58, 60, 62, 64, 65, 67 and 68 have superior AGE breaking activity compared to PTB, of which the potency of compounds 49, 56-58,60 62, 64, 65, 67 and 68 are significantly much higher. \n\n In-vivo Screening for AGE-breaking Activity \n\n The test compounds were studied for their beneficial effects on diabetic neuropathy and nephropathy in a rat model of diabetes. The rats were divided into three groups. The first group consisted of age matched untreated non-diabetic animals. The second group consisted of diabetic controls and the third group was the diabetic group treated with the test compound. Each treatment group had its own corresponding control and diabetic groups. The second and third groups were treated with Streptozotocin (STZ) at 60 mg/kg for the induction of diabetes. After completion of 12 weeks of diabetes the rats were treated with the test compound daily (doses shown in table) for a period of 8 weeks. At the end of the treatment the creatinine clearances and nerve conduction velocities (NCV) of the animals were estimated. \n\n Creatinine clearances of the rats were estimated as follows Creatinine clearance = Concentration of creatinine in the urine Concentration of creatinine in the blood . ml urine passed / minute \n\n The creatinine clearance in untreated diabetic group was compared with the treated group and the percentage improvements are shown in the Table 3. \n\n The nerve conduction velocity was measured using a modified method of Biro et al 1998. Briefly under ether anesthesia the sciatic and tibial nerves were electrically stimulated at the sciatic notch or ankle, respectively. Electromyograms (EMG's) recorded from the plantar muscles consisted of two components: (1) the short latency direct motor response (M) and the monosynaptically elicited long-latency sensory response (H, Hoffmann reflex). Latency and the duration of the M responses were measured and the motor nerve conduction velocity (MNCV) was calculated as follows: MNCV = Distance between the sciatic and tibial stimulation points Differences of the latency for M sciatic and M tibial . \n\n The percentage improvement in the nerve conduction velocities in the group treated with the test compounds was calculated as follows: % Improvement in the NCV s = NCV of the treated group - NCV of the diabetic group NCV of the control group - NCV of the diabetic group . \n\n\n TABLE 3 \n\n Effect of compound Nos 33 and 39 on the creatinine clearance and \n nerve conduction velocities: \n Compound No. 33 Compound No. 39 \n Parameters (7.5 mg/kg, b.i.d.) (6.0 mg/kg, b.i.d.) \n\n % Increase in creatinine 103.0 5.0 \n clearance \n % Increase in the NCV 60.0 58.4 \n\n\n The results show that compounds of this class have beneficial effects on creatinine clearance and nerve conduction velocities. \n\n Discussion of the Test Results \n\n All the test compounds mentioned in the current application have shown an invitro AGE-breaker effect. Under conditions of chronic hyperglycemia in rats there is a spontaneous non-enzymatic reaction between glucose, lipids and proteins that leads to the formation of advanced glycosylation end products. In this animal model decreased creatinine clearance and decreased nerve conduction velocity have been demonstrated. These changes are related to damage to renal and neuronal tissues. During chronic NIDDM patients, there is a decrease in the creatinine clearances as a manifestation of the diabetes induced renal damage. One of the major factors contributing to renal damage is the glycation of the long-lived proteins in the kidney. It is well recognized that there is a decrease in the nerve conduction velocities in chronic diabetic subjects, which is a manifestation of neuropathy. Breaking of cross-linked proteins in the neuronal tissues and associated vasculature could lead to an improvement in the neuronal function. \n\n The compounds of the present invention have shown a functional improvement both in terms of the improvement in the creatinine clearance and an improvement in the nerve conduction velocities. The evidences stated above clearly demonstrate that these compounds could play a major role in the prevention and treatment of various diabetic and aging related complications like nephropathy and neuropathy. \n\n The following examples give method of preparation of the specific novel compounds of the invention as given in Table 1. The following compounds suggested are by way of example alone and in no way restrict the invention. \n\n EXAMPLE 2 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-(2-oxo-2-phenylethyl)dibromide (Compound 1) \n\n To a boiling solution of N,N-bis-(nicotinyl)hydrazine (1.21 g., 0.005 mol.) in methanol (20 ml.), a solution of phenacyl bromide (1.99 g., 0.01 mol.) in isopropanol (10 ml.) was added and the reaction mixture was refluxed for 6 hrs. The reaction mixture was concentrated under vacuum (10 ml.) and filtered. The obtained residue was washed with hot ethylacetate and then the isolated solid was powdered. It was recrystallised from a mixture of methanol and ethylacetate (3:1, 20 ml) to afford a pale yellow solid. \n\n Yield: 60% \n\n m.p.: 260-262 C. (decomp.) \n\n IR(KBr, cm ^{ 1 } ): 1696 and 1680 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 11.65(2H,s), 9.56(2H,s), 9.21-9.16(4H,m), 8.49-8.45 (2H,m), 8.08-8.05 (4H,d), 7.81-7.77(2H,m), 7.68-7.64 (4H,m), 6.58 (4H,s) \n\n Mass (m/z): 479, 480 \n\n According to the above mentioned procedure the following compounds are synthesized by reacting the corresponding pyridine derivatives with appropriate reagents by refluxing in methanol, ethanol, propanol, toluene or xylene for 6-48 hrs. to get the desired compounds: \n\n EXAMPLE 3 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-(2-ethoxy-2-oxoethyl)-, dibromide (Compound 2) \n\n Yield: 47% \n\n m.p.: 180-182 C. (decomp.) \n\n IR(KBr, cm ^{ 1 } ): 1744, 1664 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 11.65 (2H,s), 9.62 (2H,s), 9.28-9.26 (2H,d), 9.17-9.15 (2H,d), 8.47-8.44 (2H,m), 5.77 (4H,s), 4.26 (4H,q), 1.27 (6H,t) \n\n Mass (m/z): 415, 416 \n\n EXAMPLE 4 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(2,4-dichlorophenyl)-2-oxoethyl-, dibromide (Compound 3) \n\n Yield: 24% \n\n m.p.: 225-227 C. (decomp.) \n\n IR (KBr, cm ^{ } ): 1702, 1666 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 11.69 (2H,s), 9.58 (2H,bs), 9.20-9.18 (4H,m), 8.49-8.47 (2H,m), 8.17-8.15 (2H,d), 7.92 (2H,bs), 7.78-7.76 (2H,d), 6.50 (4H,s) \n\n Mass (m/z): 615, 617, 618, 620. \n\n EXAMPLE 5 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(2-pyridinyl)hydrazinocarbonyl-, bromide (Compound 4) \n\n Yield: 16% \n\n m.p.: 210-212 C. \n\n IR (KBr, cm ^{ 1 } ): 3140, 3005, 1732 and 1690 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 9.63 (1H,s), 9.27 (2H,d), 8.49-8.45 (1H,m) 8.13-8.07 (2H,m), 7.32-7.30 (1H,m), 7.12-7.11(1H,m), 5.77 (2H,s), 4.23 (2H,q), 1.25 (3H,t) \n\n Mass (m/z): 301, 302 \n\n EXAMPLE 6 \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound 5) \n\n Yield: 30% \n\n m.p.: 199-200 C. \n\n IR (KBr, cm ^{ 1 } ): 1714, 1673 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.38 (1H,s), 9.97 (1H,s) 9.51 (1H,s), 9.16 (1H,d), 9.06-9.04 (1H,m), 8.43-8.39 (1H,m), 8.25-8.21 (2H,m), 7.43-7.41 (1H,t), 6.45 (2H,s), 3.08 (3H,s). \n\n Mass (m/z): 340, 341, 342 \n\n EXAMPLE 7 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-oxo-2-(2-thienyl)ethyl-, dibromide (Compound 6) \n\n Yield: 33% \n\n m.p.: 259-261 C. (decomp.) \n\n IR (KBr, cm ^{ 1 } ): 3330, 1702, 1674, 1655 and 1626 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 11.59 (2H,s), 9.50 (2H,s), 9.15-9.08 (4H,m), 8.40-8.36 (2H,m), 8.17-8.14 (4H,m), 7.33(2H,t), 6.42 (4H,s) \n\n Mass (m/z): 491, 492. \n\n EXAMPLE 8 \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-(2-ethoxy-2-oxoethyl)-, bromide (Compound 7) \n\n Yield: 85% \n\n m.p.: 132-134 C. \n\n IR (KBr, cm ^{ 1 } ): 3210, 3067, 1726, 1687, 1656 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 9.46 (1H,s), 9.37 (1H,t), 9.11(1H,t), 8.97 (1H,d), 8.33-8.29 (1H,m) 7.95-7.93 (2H,m), 7.63-7.59 (1H,m), 7.49-7.45 (2H,m), 5.65 (2H,s), 4.39 (2H,t), 4.19 (2H,q), 3.70-3.69 (2H,m), 1.20 (3H,t) \n\n Mass (m/z): 357, 358, 359 \n\n EXAMPLE 9 \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-2-(2,4-dichlorophenyl)-2-oxoethyl-, bromide (Compound 8): \n\n Yield: 75% \n\n m.p.: 102-104 C. \n\n IR(KBr, cm ^{ 1 } ): 1703, 1685, 1675 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 9.41-9.37 (2H,m), 9.03-8.98 (2H,m)8.34-8.30 (1H,m), 8.04 (1H,d), 7.91-7.89 (2H,m), 7.82 (1H,d), 7.68-7.65 (1H,m), 7.58-7.55 (1H,m), 7.43 (2H,t), 6.35 (2H,s), 4.36 (2H,t), 3.68-3.64 (2H,m) \n\n Mass (m/z): 457, 458, 459, 460, 461, 462 \n\n EXAMPLE 10 \n\n Pyridinium, 1-2-oxo-2-(2-thienyl)ethyl-3-2-(2-pyridinyl)hydrazinocarbonyl-, bromide (Compound 9) \n\n Yield: 10% \n\n m.p.: 212-214 C. (decomp) \n\n IR(KBr, cm ^{ 1 } ): 1685, 1649 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 11.21 (1H,bs), 9.59 (1H,s), 9.19 (2H,d), 8.44 (1H,t), 8.27-8.24 (2H,m), 8.08 (1H,bs), 7.62 (1H,bs), 7.44 (1H,t), 6.85-6.79 (2H,m), 6.50 (2H,s) \n\n Mass (m/z): 339, 340, 341 \n\n EXAMPLE 11 \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-2-(2-pyridinyl)hydrazinocarbonyl-, bromide (Compound 10) \n\n Yield: 4% \n\n m.p.: 190 C. (decomp) \n\n IR(KBr, cm ^{ 1 } ): 1683, 1670, 1648 \n\n ^{ 1 } H NMR (DMSOd _{ 6 } , 400 MHz) : 11.14 (1H,bs), 9.53 (1H,s), 9.18-9.13 (2H,m), 8.45-8.42 (1H,t), 8.08-8.06 (3H,m), 7.80 (1H,t), 7.67 (2H,t), 7.62-7.55 (1H,m), 6.83-6.76 (2H,m), 6.54 (2H,s) \n\n Mass (m/z): 333, 334, 335 \n\n EXAMPLE 12 \n\n Pyridinium, 3-(hydrazinocarbonyl)-1-(2-oxo-2-phenylethyl)-, bromide (Compound 11) \n\n Yield: 15% \n\n m.p.: 215-216 C. \n\n IR(KBr, cm ^{ 1 } ): 1695, 1680 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 10.25 (1H,s) 9.65 (1H,s), 9.35-9.32 (2H,m), 8.90-8.88 (1H,m) 8.50-8.46 (2H,d), 8.21-8.17 (1H,m), 8.05-8.07 (2H,m), 6.50 (2H,s), 4.45 (2H,s). \n\n Mass (m/z): 256, 257. \n\n EXAMPLE 13 \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound 12) \n\n Yield: 35% \n\n m.p.: 227-228 C. \n\n IR(KBr, cm ^{ 1 } ): 1710, 1702 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.30, (1H,s), 9.88 (1H,s), 9.41 (1H,s), 9.06-9.05 (1H,d) 8.98-8.96 (1H,d), 8.34-8.31 (1H,m), 7.97 (2H,d), 7.72-7.69 (1H,t), 7.59-7.56 (2H,t), 6.44 (2H,s), 2.99 (3H,s) \n\n Mass (m/z): 334, 335 \n\n EXAMPLE 14 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(methylsulfonyl)hydrazinocarbonyl-, bromide (Compound 13) \n\n Yield: 38% \n\n m.p.: 75-76 C. \n\n IR(KBr, cm ^{ 1 } ): 1739, 1697 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.39 (1H,s), 9.96 (1H,s), 9.56 (1H,s), 9.23 (1H,d), 9.06 (1H,d), 8.40 (1H,t), 5.75 (2H,s), 4.27-4.22 (2H,q), 3.08 (3H,s), 1.26 (3H,t) \n\n Mass (m/z): 301, 302, 303 \n\n EXAMPLE 15 \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound 14) \n\n Yield: 28% \n\n m.p.: 187-188 C.(dec.) \n\n IR(KBr, cm ^{ 1 } ): 1700, 1633 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.38 (1H,s), 10.45 (1H,s), 9.33(1 H,s), 9.13-9.12 (1H,d), 8.95 (1H,d), 8.38 (1H,t), 8.05 (2H,d), 7.89 (2H,d), 7.80 (1H,t), 7.66 (3H,t), 7.57 (2H,t), 6.50 (2H,s). \n\n Mass (mn/z): 396, 397, 398 \n\n EXAMPLE 16 \n\n Pyridinium, 2-chloro-1-(2-oxo-2-phenylethyl)-3-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound 15) \n\n Yield: 23% \n\n m.p.: 247-250 C. (decomp) \n\n IR(KBr, cm ^{ 1 } ): 1685, 1679, \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.12 (1H,s), 9.49 (1H,s), 9.07-9.03(1H,m), 8.44 (1H, t), 8.07 (2H,d), 7.80 (1H,t), 7.67 (2H,t), 7.18 (2H,t), 6.87 (2H,d), 6.77 (1H,t), 6.50 (2H,s). \n\n Mass (m/z): 430, 431, 432 \n\n EXAMPLE 17 \n\n Pyridinium, 3-2-(acetyloxy)ethoxycarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound 16) \n\n Yield: 40% \n\n m.p.: 152-153 C. \n\n IR(KBr, cm ^{ 1 } ): 1737, 1691, 1635 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 9.63 (1H,s), 9.24 (1H,d), 9.12 (1H,d), 8.43 (1H,t), 8.07 (2H,d), 7.80 (1H,t), 7.67 (2H,t), 6.59 (2H,s), 4.62-4.60 (2H,m), 4.39-4.37 (2H,m), 2.03 (3H,s) \n\n Mass (m/z): 328, 329 \n\n EXAMPLE 18 \n\n Pyridinium, 3-2-(benzoyloxy)ethoxycarbonyl-1-(2-ethoxy-2-oxoethyl)-, bromide (Compound 17) \n\n Yield: 35% \n\n m.p.: 142-143 C. \n\n IR(KBr, cm ^{ 1 } ): 1736, 1718, 1636 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 9.60 (1H,s), 9.20-9.18 (1H,d), 9.04-9.02 (1H,d), 8.33-8.29 (1H,m), 7.90-7.88 (2H,d), 7.58-7.57 (1H,m), 7.46-7.42 (2H,m), 5.67 (2H,s), 4.71-4.68 (2H,m), 4.58-4.56 (2H,m), 4.15 (2H,q), 1.16 (3H,t) \n\n Mass (m/z): 358, 359, 360 \n\n EXAMPLE 19 \n\n Pyridinium, 4-2-(benzoyloxy)ethylaminocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound 18) \n\n m.p.: 210-211 C. \n\n IR(KBr, cm ^{ 1 } ): 1723, 1680, 1668 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 9.52 (1H,t), 9.14 (2H,d), 8.50 (2H,d), 8.25-8.21 (2H,m), 8.01-7.99 (2H,d), 7.67 (1H,t), 7.55-7.51 (2H,m), 7.42-7.40 (1H,m), 6.42 (1H,s) 4.47-4.45 (2H,t), 3.77-3.73 (2H, m). \n\n Mass (m/z): 395, 396 \n\n EXAMPLE 20 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-4-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound 19) \n\n Yield: 60% \n\n m.p.: 171-173 C. \n\n IR (KBr, cm ^{ 1 } ): 1745, 1685, 1645. \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.41 (1H,s), 10.39 (1H,s), 9.10 (2H,d), 8.27 (2H,d), 7.82-7.80 (2H,d), 7.60-7.57 (1H,t), 7.50-7.46 (2H,t), 5.63 (2H,s), 4.18-4.12 (2H,q), 1.19-1.15 (3H,t). \n\n Mass (m/z): 364, 365, 366 \n\n EXAMPLE 21 \n\n Pyridinium, 1-2-oxo-2-(phenylamino)ethyl-4-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound 20) \n\n Yield: 10% \n\n m.p.: 225-227 C. \n\n IR (KBr, cm ^{ 1 } ): 1693, 1642, 1592 \n\n ^{ 1 } HNMR(DMSOd _{ 6 } , 400 MHz) : 11.55 (1H,s), 10.99 (1H,s), 10.49 (1H,s), 9.20 (2H,d), 8.34 (2H,d), 7.89 (2H,d), 7.73-7.64 (1H,t), 7.61-7.56 (4H,m), 7.37-7.33 (2H,t), 7.12-7.09 (1H,t), 5.73 (2H,s). \n\n Mass (m/z): 411, 412, 413, 414 \n\n EXAMPLE 22 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(phenylsulfonyl)hydrazinocarbonyl-, bromide (Compound 21) \n\n Yield: 75% \n\n m.p.: 145-147 C. \n\n IR(KBr cm ^{ 1 } ): 1744, 1713, 1633 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.27(1H,s), 10.36 (1H,s), 9.28 (1H,s), 9.09 (1H,d), 8.83 (1H,d), 8.27-8.24 (1H,m), 7.82-7.79 (2H,m), 7.58 (1H,t), 7.48 (2H,t), 5.59 (2H,s), 4.17-4.12 (2H, q), 1.16 (3H,t). \n\n Mass (m/z): 364, 365, 366 \n\n EXAMPLE 23 \n\n Pyridinium, 1-2-(2,4-dichlorophenyl)-2-oxoethyl-3-(2-methoxyethoxy)carbonyl-, bromide (Compound 22) \n\n Yield: 25% \n\n m.p.: 156-158 C. \n\n IR (KBr, cm ^{ 1 } ): 1731, 1706, 1640 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) :9.61 (1H,s), 9.20 (1H,d), 9.13 (1H,d), 8.45-8.41 (1H,m), 8.15 (1H,d), 7.92 (1H,d), 7.78-7.76 (1H,m), 6.49 (2H,s), 4.56-4.54 (2H,m), 3.72-3.69 (2H,q), 3.31 (3H,s). \n\n Mass (m/z): 368, 369, 370, 371 \n\n EXAMPLE 24 \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-2-oxo-2-(phenylamino)ethyl-, chloride (Compound 23) \n\n Yield: 70% \n\n m.p.: 171-172 C. \n\n IR (KBr, cm ^{ 1 } ): 1720, 1692, 1668 \n\n ^{ 1 } HNMR:(DMSOd _{ 6 } , 400 MHz) : 11.06 (1H,s), 9.67 (1H,t), 9.59 (1H,s), 9.20 (1H,d), 9.11 (1H,d), 8.36-8.32(1H,m), 8.00 (2H,d), 7.66-7.61 (3H,m),7.51 (2H,t),7.34 (2H,t), 7.10 (1H,t), 5.77 (2H,s), 4.45 (2H,t), 3.76-3.72 (2H,q). \n\n Mass (m/z): 404, 405, 406, 407 \n\n EXAMPLE 25 \n\n Pyridinium, 1-2-oxo-2-(2-thienyl)ethyl-3-2-(phenylamino)carbonylhydrazinocarbonyl-, bromide (Compound 24) \n\n Yield: 30% \n\n m.p.: 202-204 C. \n\n IR (KBr, cm ^{ 1 } ): 1718, 1673 \n\n ^{ 1 } HNMR : (DMSOd _{ 6 } , 400 MHz) : 11.03 (1H,s), 9.55 (1H,s), 9.18 (1H,d), 9.10 (1H,d), 9.00 (1H,s),8.57 (1H,s), 8.46-8.42 (1H,t), 8.25-8.22 (2H,m), 7.47-7.45 (2H,d), 7.43-7.41 (1H,t), 7.29-7.25 (2H,t), 7.0-6.96 (1H,t), 6.46 (2H,s). \n\n Mass (m/z): 381, 382, 383 \n\n EXAMPLE 26 \n\n Pyridinium, 3-2-(acetyloxy)ethylaminocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound 25) \n\n Yield: 55% \n\n m.p.: 186-188 C. \n\n IR (KBr, cm ^{ 1 } ): 1734, 1697, 1679 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 9.47(1H,s), 9.36 (1H,t), 9.13-9.05 (2H,m), 8.42-8.38 (1H,m), 8.06 (2H,d), 7.80 (1H,t), 7.67 (2H,t), 6.54 (2H,s), 4.18 (2H,t), 3.61-3.57 (2H,q), 2.02 (3H,s). \n\n Mass (m/z): 327, 328, 329. \n\n EXAMPLE 27 \n\n Pyridinium, 1-2-oxo-2-(phenylamino)ethyl-3-2-(phenylsulfonyl)hydrazinocarbonyl-, chloride (Compound 26) \n\n Yield: 38% \n\n m.p.: 232-234 C. \n\n IR (KBr, cm ^{ 1 } ): 1689, 1636, 1596 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.30 (1H,s), 10.80 (1H,s), 10.37 (1H,s), 9.29 (1H,s), 9.09 (1H,d), 8.81 (1H,d), 8.25-8.21 (1H,t), 7.82-7.80 (2H,d), 7.59-7.46 (5H,m), 7.28-7.24 (2H,t), 7.04-7.00 (1H,t), 5.62 (2H,s). \n\n Mass (m/z):411, 412, 413, 414 \n\n EXAMPLE 28 \n\n Pyridinium, 3-2-(4-methylphenyl)sulfonylhydrazinocarbonyl-1-2-oxo-2-(phenylamino)ethyl-, chloride (Compound 27) \n\n Yield: 48% \n\n m.p.: 205-206 C. \n\n IR(KBr, cm ^{ 1 } ): 1712, 1681, 1632 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.35 (1H,s), 10.86 (1H,s), 10.36 (1H,s), 9.38 (1H,s), 9.17 (1H,d), 8.90 (1H,d), 8.34-8.30 (1H,m), 7.78 (2H,d), 7.59 (2H,d), 7.37-7.33 (4H,m), 7.11 (1H,t), 5.70 (2H,s), 2.36 (3H,s). \n\n Mass (m/z): 425, 426, 427, 428 \n\n EXAMPLE 29 \n\n Pyridinium, 3-2-(benzoyloxy)ethoxycarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound 28) \n\n Yield: 35% \n\n m.p.: 132-134 C. \n\n IR (KBr, cm ^{ 1 } ): 1730, 1705, 1690 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 9.80 (1H,s), 9.36 (1H,d), 9.30 (1H,d), 8.58 (1H,t), 8.21 (2H,d), 8.12 (2H,d), 7.95 (1H,t), 7.85-7.80 (3 H,m), 7.68 (2H,t), 6.71 (2H,s), 4.95-4.93 (2H,m), 4.82-4.80 (2H,m). \n\n Mass (m/z): 390, 391, 392. \n\n EXAMPLE 30 \n\n Pyridinium, 3-(2-benzoylhydrazino)carbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound 29) \n\n Yield: 45% \n\n m.p.: 80-81 C. \n\n IR(KBr Cm ^{ 1 } ): 1700, 1663, 1631 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.49 (1H,s), 10.95 (1H,s), 9.67 (1H,s), 9.34 (1H,d), 9.27 (1H,d), 8.52-8.48 (1H,m), 8.29-8.28 (2H,m), 8.00 (2H,d), 7.68 (1H,t), 7.59 (2H,t), 7.46 (1H,t), 6.63 (2H,s) \n\n Mass (m/z): 366, 367, 368, 369 \n\n EXAMPLE 31 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(phenylmethyl)sulfonylhydrazinocarbonyl-, bromide (Compound 30) \n\n Yield: 50% \n\n m.p.: 147-148 C. \n\n IR (KBr, cm ^{ 1 } ): 1749, 1698, 1640 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.57 (1H,s), 10.21 (1H,s), 9.75 (1H,s), 9.38 (1H,d), 9.24 (1H,d), 8.59-8.56(1H,m), 7.67-7.65 (2H,m), 7.58-7.52 (3H,m), 5.90 (2H,s), 4.68 (2H,s), 4.45-4.39(2H,q),1.43 (3H,t). \n\n Mass (m/z): 377, 378, 379 \n\n EXAMPLE 32 \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-2-(phenylmethyl)sulfonylhydrazinocarbonyl-, bromide (Compound 31) \n\n Yield: 80% \n\n m.p.: 205-207 C. \n\n IR (KBr, Cm ^{ 1 } ): 1687, 1637 \n\n ^{ 1 } HNMR (DMSOd _{ 6 } , 400 MHz) : 11.59 (1H,s), 10.20 (1H,s), 9.71 (1H,s), 9.33 (1H,d), 9.27 (1H,d), 8.62-8.59 (1H,m), 8.25-8.23 (2H,d), 7.99-7.95 (1H,t), 7.86-7.82 (2H,t), 7.67-7.65 (2H,m), 7.57-7.52 (3H,m), 6.72 (2H,s), 4.69 (2H,s). \n\n Mass (m/z): 410, 411, 412, 413 \n\n EXAMPLE 33 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(2-furanyl)-2-oxoethyl-, dibromide (Compound No: 32) \n\n Yield: 23% \n\n m.p.: 267-269 C. (dec) \n\n IR (KBr, cm ^{ 1 } ): 1687, 1660 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 11.65 (2H,s), 9.56 (2H,s), 9.21-9.15 (4H,m), 8.48-8.44 (2H,t), 8.23 (2H,s), 7.74-7.73 (2H,d), 6.91-6.90 (2H,d) 6.34 (4H,s) \n\n Mass (m/z): 459, 460, 461 \n\n EXAMPLE 34 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(2-thienyl)-2-oxoethyl-, dichloride (Compound No: 33) \n\n Yield: 35% \n\n m.p.: 275-277 C. \n\n IR (KBr, cm ^{ 1 } ): 3374, 1665,1632, 1410 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 11.88 (2H,s), 9.66 (2H,s), 9.29-9.24 (4H,m), 8.48-8.44 (2H,m), 8.25-8.23 (4H,m), 7.43-7.41 (2H,m), 6.53 (4H,s). \n\n Mass (m/z): 491, 492, 493, 494 \n\n EXAMPLE 35 \n\n Pyridinium, 3-2-(3-cyclohexyl-1-oxopropyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No: 34) \n\n Yield: 15% \n\n m.p.: 217-219 C. (dec) \n\n IR (KBr, cm ^{ 1 } ): 3190, 1708, 1667 and 1404 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 11.07 (1H,s), 10.22 (1H,s), 9.51 (1H,s), 9.16-9.15 (1H,d), 9.06-9.04 (1H,d), 8.42-8.40 (1H,m), 8.25-8.21 (2H,m), 7.43-7.40 (1H,m), 6.44 (2H,s), 2.25-2.22 (2H,t), 1.72-1.60 (5H,m), 1.49-1.43 (2H,q), 1.24-1.10 (4H,m), 0.9-0.85 (2H,m) \n\n Mass (m/z): 400,401,402 and 403 \n\n EXAMPLE 36 \n\n Pyridinium, 3-2-(3-cyclohexyl-1-oxopropyl)hydrazinocarbonyl-1-2-oxo-2-(phenylamino)ethyl-, chloride (Compound No: 35) \n\n Yield: 25% \n\n m.p.: 234-236 C. (dec) \n\n IR (KBr, cm ^{ 1 } ): 1689, 1652 and 1625 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 11.11 (1H,s), 10.95 (1H,s), 10.23 (1H,s), 9.56 (1H,s), 9.23-9.21 (1H,d), 9.06-9.04 (1H,d), 8.38-8.35 (1H,m), 7.62-7.60 (2H,d), 7.37-7.33 (2H,t), 7.12-7.09 (1H,t), 5.75 (2H,s), 2.25-2.22 (2H,t), 1.72-1.60 (5H,m) 1.49-1.43 (2H,m), 1.25-1.10 (4H,m), 0.91-0.83 (2H,m) \n\n Mass (m/z): 409, 410, 411 and 412 \n\n EXAMPLE 37 \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No:36) \n\n Yield: 40% \n\n m.p.: 125-127 C. \n\n IR (KBr, cm ^{ 1 } ): 1710 and 1675 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 9.48 (1H,s), 9.43-9.41 (1H,t), 9.12-9.11 (1H,d), 9.05-9.02 (1H,d), 8.40-8.36 (1H,m), 8.25-8.20 (2H,m), 8.00-7.98 (2H,m), 7.68-7.64 (1H,m), 7.54-7.50 (2H,m), 7.42-7.40 (1H,m), 6.43 (2H,s), 4.46-4.43 (2H,t), 3.77-3.73 (2H,q) \n\n Mass (m/z): 395, 396, 397 and 398 \n\n EXAMPLE 38 \n\n Pyridinium, 3-2-(benzoyloxy)ethylaminocarbonyl-1-(4-ethoxy-2,4-dioxobutyl)-, chloride (Compound No: 37) \n\n Yield: 35% \n\n m.p.: 147-149 C. \n\n IR (KBr, cm ^{ 1 } ): 1743, 1720, 1680 and 1627 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 9.62-9.59 (1H,t), 9.32-9.29 (1H,s), 9.05-9.03 (1H,d), 8.93-8.90 (1H,d), 8.27-8.24 (1H,m), 7.92-7.89 (2H,d), 7.59-7.55 (1H,m), 7.45-7.41 (2H,m), 5.82 (2H,s), 4.37-4.34 (2H,t), 4.08-4.03 (2H,q), 3.80 (2H,s), 3.67-3.63 (2H,q), 1.15-1.11 (3H,t), \n\n Mass (m/z): 399, 400 and 401 \n\n EXAMPLE 39 \n\n Pyridinium, 3-(2-methoxyethyl)aminocarbonyl-1-2-(2,4-dichlorophenyl)-2-oxoethyl-, bromide (Compound No: 38) \n\n Yield: 70% \n\n m.p.: 93-95 C. \n\n IR (KBr, cm ^{ 1 } ): 1704, 1664 and 1636 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 9.48 (1H,s), 9.29 (1H,bs), 9.11-9.08 (2H,m), 8.41-8.38 (1H,m), 8.15-8.13 (1H,d), 7.92-7.91 (1H,t), 7.78-7.75 (1H,m), 6.44 (2H,s) 3.52 (2H,bs), 3.51 (2H,bs), 3.28 (3H,s) \n\n Mass (m/z): 367,368,369 and 370 \n\n EXAMPLE 40 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(cyclopropylamino)-2-oxoethyl-, dichloride (Compound No: 39) \n\n Yield: 40% \n\n m.p.: 228-230 C. \n\n IR (KBr cm ^{ 1 } ): 1675, 1636 and 1298 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 11.85 (2H,s), 9.59 (2H,s), 9.25-9.19 (4H,m), 9.00-8.99 (2H,d), 8.39-8.36 (2H,m), 5.53 (4H,s), 2.73-2.66 (2H,m), 0.78-0.62 (4H,m), 0.53-0.49 (4H,m) \n\n Mass (m/z): 437, 438 and 439 \n\n EXAMPLE 41 \n\n Pyridinium, 1-2-(cyclopropylamino)-2-oxoethyl-3-(2-methoxyethyl)aminocarbonyl-, chloride (Compound No: 40) \n\n Yield: 10% \n\n m.p.: 122-124 C. \n\n IR (KBr, cm ^{ 1 } ): 1661, 1633, 1549 and 1121 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 9.40 (1H,s), 9.08-9.02 (2H,m), 8.28-8.25 (1H,m), 5.53 (2H,s), 3.66-3.61 (4H,m), 3.39 (3H,s), 2.78-2.74 (1H,m), 0.80-0.75 (2H,m), 0.64-0.61 (2H,m) \n\n Mass (m/z): 278, 279 and 280 \n\n EXAMPLE 42 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(1-methylethyl)amino-2-oxoethyl-, dichloride (Compound No: 41) \n\n Yield: 35% \n\n m.p.: 114-116 C. (dec) \n\n IR (KBr, cm ^{ 1 } ): 1707, 1668 and 1637 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 11.84 (2H,s), 9.59 (2H,s), 9.21-9.18 (4H,m), 8.74-8.72 (2H,d), 8.39-8.35 (2H,m), 5.53 (4H,s), 3.92 3.84 (2H,m), 1.14-1.02 (12H,d) \n\n Mass (m/z): 441, 442 and 443 \n\n EXAMPLE 43 \n\n Pyridinium, 3-2-(2-chloro-3-pyridinyl)carbonylhydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, chloride (Compound No: 42) \n\n Yield: 56% \n\n m.p.: 233-235 C. \n\n IR (KBr, cm ^{ 1 } ): 1680, 1637, 1404 and 1293 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 11.62 (1H,s), 11.05 (1H,s), 9.62 (1H,s), 9.24-9.23 (1H,d), 9.18-9.16 (1H,d), 8.58-8.56 (1H,m), 8.46-8.43 (1H,m), 8.26-8.24 (2H,m), 8.02-8.00 (1H,m), 7.61-7.58 (1H,m), 7.43-7.41 (1H,m), 6.51 (2H,s) \n\n Mass (m/z): 401, 402, 403, 404 and 405 \n\n EXAMPLE 44 \n\n Pyridinium, 1-2-(1-methylethyl)amino-2-oxoethyl-3-2-(methylsulfonyl)hydrazinocarbonyl-, chloride (Compound No: 43) \n\n Yield: 10% \n\n m.p.: 227-229 C. \n\n IR (KBr, cm ^{ 1 } ): 1691, 1670, 1566 and 1330 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MHz) : 11.55 (1H,s), 9.94 (1H,s), 9.52 (1H,s), 9.16-9.14 (1H,m), 9.09-9.07 (1H,m), 8.72-8.70 (1H,m), 8.34-8.30 (1H,m), 5.50 (2H,s), 3.89-3.84 (1H,m), 3.11 (3H,s), 1.13-1.12 (6H,d) \n\n Mass (m/z): 315, 316 and 317 \n\n EXAMPLE 45 \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(1-pyrrolidinyl)ethyl-, chloride (Compound No: 44) \n\n Yield: 21.00% \n\n m.p.: 205-207 C. \n\n IR (KBr, cm1): 1699, 1646 and 1589 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.50 (1H,s), 9.94 (1H,s), 9.46 (1H,s), 9.11-9.06 (2H,m), 8.36-8.33 (1H,t), 5.75 (2H,s), 3.55-3.48 (3H,m), 3.10 (3H,s), 2.00-1.95 (2H,m), 1.87-1.81 (2H,m) \n\n Mass (m/z): 327, 328, 329 and 330 \n\n EXAMPLE 46 \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, chloride (Compound No: 45) \n\n Yield: 31.00% \n\n m.p.: 215-217 C. \n\n IR (KBr, cm ^{ 1 } ): 1685, 1666 and 1635 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.49, (1H,s), 9.96 (1H,s), 9.55 (1H,s), 9.18 (1 H,d), 9.10 (1H,d), 8.43-8.39 (1H,t), 8.25-8.22 (2H,m), 7.42 (1H,t) 6.47 (2H,s), 3.09 (3H,s). \n\n Mass (m/z): 340, 341, 342 and 343 \n\n EXAMPLE 47 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-carboxymethyl)-, dichloride (Compound No: 46) \n\n Yield: 43.00% \n\n m.p.: 235-240 C. (d) \n\n IR (KBr, cm ^{ 1 } ): 1743, 1700 and 1672 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.89 (2H,s), 9.69 (2H,s), 9.31-9.29 (2 H,d), 9.25-9.23 (2H,d), 8.43-8.39 (2H,t) 5.70 (4H,s) \n\n Mass (m/z): 360,361,362 \n\n EXAMPLE 48 \n\n Pyridinium, 3-bromo-5-2-methoxyethyl)aminocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, chloride (Compound No: 47) \n\n Yield: 31.00% \n\n m.p.: 180-182 C. \n\n IR (KBr, cm ^{ 1 } ): 1661 and 1620 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MH _{ z } ) : 9.58-9.54 (2H,d), 9.43-9.39 (2H,d), 8.25-8.21 (2H,m), 7.41 (1H,t), 6.43 (2H,s), 3.51 (4H,m), 3.29 (3H,s). \n\n Mass (m/z): 384, 385, 386, 387 and 388 \n\n EXAMPLE 49 \n\n Pyridinium, 3-2-6-(methoxycarbonyl)-3-pyridinylcarbonylhydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, chloride (Compound No: 48) \n\n Yield: 30.00% \n\n m.p.: 222-225 C. \n\n IR (KBr, cm ^{ 1 } ): 1726, 1708 and 1662 \n\n ^{ 1 } H NMR (DMSO d _{ 6 } , 400 MH _{ z } ) : 11.47 (1H,s), 11.23 (1H,s), 9.58 (1H,s), 9.22-9.15 (3H,m), 8.56-8.53 (1H,d), 8.46-8.43 (1H,t),. 8.25-8.21 (3H,m), 7.42 (1H,t), 6.49 (2H,s), 3.95 (3H,s) \n\n Mass (m/z): 425, 426 and 427 \n\n EXAMPLE 50 \n\n Pyridinium, 2-methyl-1-(2-oxo-2-thien-2-yl-ethyl)-5-2--1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-ylcarbonylhydrazinocarbonyl-, dichloride (Compound No: 49) \n\n Yield: 40% \n\n m.p.: 76-80 C. (dec) \n\n IR (KBr,cm ^{ 1 } ): 1637,1513 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.69 (2H,s), 9.59-9.53 (2H,d), 9.19 (2H,m), 9.05 (1H,d), 8.46-8.43 (1H,t),8.34 (1H,d), 8.27-8.23 (4H,m), 7.45-7.41 (2H,m), 6.56 (2H,s), 6.48 (2H,s), 2.81 (3H,s). \n\n Mass (m/z): 505,506,507. \n\n EXAMPLE 51 \n\n Pyridinium, 3-2-(1-methylethyl)sulfonylhydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No: 50) \n\n Yield: 70% \n\n m.p.: 90-95 C. (dec) \n\n IR (KBr,cm ^{ 1 } ): 1638,1589 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.27 (1H,s) ,9.91 (1H,s), 9.60 (1H,s), 9.19-9.15 (2H,m), 8.42-8.36 (1H,m) ,8.25-8.21 (2H,m) ,7.43-7.41 (1H,t), 6.45 (2H,s), 1.35-1.34 (6H,d). \n\n Mass (m/z): 368,369,370 \n\n EXAMPLE 52 \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-4-(phenylmethyl)-1-piperidinylethyl-, chloride (Compound No: 51) \n\n Yield: 17% \n\n m.p.: 76-78 C. \n\n IR (KBr,cm ^{ 1 } ): 1684,1650,1556,1540. \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.46 (1H,s), 9.55 (1H,s), 9.46 (1H,s), 9.09-9.03 (2H,m), 8.36-8.32 (1H,t), 7.33-7.29 (2H,m), 7.23-7.19 (3H,m), 5.88-5.79 (2H,m), 4.30-4.27 (1H,d), 3.76-3.73 (1H,d), 3.10 (4H,m), 2.64 (1H,t), 2.57-2.55 (2H,d), 1.85 (1H,bs), 1.72-1.63 (2H,t), 1.36-1.28 (1H,q), 1.13-1.03 (1H,m) \n\n Mass (m/z): 431,432,433 \n\n EXAMPLE 53 \n\n Pyridinium, 1-2-2-(ethoxycarbonyl)-1-pyrrolidinyl-2-oxoethyl-3-2-(methylsulfonyl)hydrazinocarbonyl-, chloride (Compound No: 52) \n\n Yield: 14% \n\n m.p.: 88-91 C. \n\n IR (KBr,cm ^{ 1 } ): 1735,1665,1539 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.48 (1 H,s), 9.96 (1H,s), 9.46 (1H,s), 9.09-9.05 (2H,m), 8.38-8.34 (1H,t), 5.94-5.80 (2H,q), 4.37-4.36 (1H,d), 4.08-4.06 (2H,d), 3.68-3.65 (2H,m), 3.09 (4H,m), 2.23-2.18 (2H,m), 2.04-1.93 (3H,m), 1.18-1.09 (3H,t) \n\n Mass (m/z): 399,400,401 \n\n EXAMPLE 54 \n\n Pyridinium, 3-bromo-5-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No: 53) \n\n Yield: 54% \n\n m.p.: Above 190-195 C.(dec) \n\n IR (KBr,cm ^{ 1 } ): 1682,1557,1540,1520 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.35 (1H,s),10.01 (1H,s), 9.57-9.54 (2H,d), 9.32 (1H,s), 8.26-8.22 (2H,m), 7.42 (1H,s), 6.39 (2H,s), 3.08 (3H,s) \n\n Mass (m/z): 418,419,420 \n\n EXAMPLE 55 \n\n Pyridinium, 3-2-(ethoxycarbonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No: 54) \n\n Yield: 69% \n\n m.p.: 155-157 C. \n\n IR (KBr,cm ^{ 1 } ): 1731,1665,1637 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.04 (1H,s), 9.59 (1H,s), 9.53 (1H,s), 9.18 (1H,s), 9.05-9.04 (1H,d), 8.42 (1H,s), 8.25-8.23 (2H,m), 7.43 (1H,s), 6.46 (2H,s), 4.12-4.11 (2H,s), 1.23 (3H,s) \n\n Mass (m/z): 334,335,336 \n\n EXAMPLE 56 \n\n Pyridinium, 1-2-(5-chloro-2-thienyl)-2-oxoethyl-3-2-(methylsulfonyl)hydrazinocarbonyl-, bromide (Compound No: 55) \n\n Yield: 87% \n\n m.p.: 228-230 C. \n\n IR (KBr,cm ^{ 1 } ): 1708,1664,1631,1550 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.40 (1H,s), 9.98 (1H,s), 9.50 (1 H,s), 9.15 (1H,d), 9.06 (1H,d), 8.43-8.39 (1H,t), 8.16-8.15 (1H,d), 7.51-7.50 (1H,d), 6.41(2H,s), 3.09 (3H,s) \n\n Mass (m/z): 374,375,376,377 \n\n EXAMPLE 57 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(4-nitro-2-thienyl)-2-oxoethyl-, dichloride (Compound No: 56) \n\n Yield: 27% \n\n m.p.: 204-207 C. \n\n IR (KBr,cm ^{ 1 } ): 1681,1539,1514 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.90 (2H,s), 9.63 (2H,s), 9.31-9.30 (4H,m), 9.24-9.22 (2H,m), 8.87 (2H,s), 8.49-8.46 (2H,t), 6.56 (4H,s) \n\n Mass (m/z): 581,582,583 \n\n EXAMPLE 58 \n\n Pyridinium, 2-methyl-5-2-(methylsulfonyl)hydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No: 57) \n\n Yield: 14% \n\n m.p.: 90-95 C.(dec) \n\n IR (KBr,cm ^{ 1 } ): 1677,1575 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.32 (1H,s), 9.97 (1H,s), 9.52(1H,s), 8.94-8.92 (1H,d), 8.32-8.24 (3H,m), 7.44 (1H,t), 6.54 (2H,s), 3.08 (3H,s), 2.79 (3H,s) \n\n Mass (m/z): 354,355,356 \n\n EXAMPLE 59 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(5-methyl-2-thienyl)-2-oxoethyl-, dichloride (Compound No: 58) \n\n Yield: 37% \n\n m.p.: Above 166-168 C.(dec) \n\n IR (KBr,cm ^{ 1 } ): 1666,1500 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.73 (2H,s), 9.59 (2H,s), 9.19-9.15 (4H,d), 8.45-8.42 (2H,t), 8.06-8.05 (2H,d), 7.15-7.14 (2H,d), 6.43 (4H,s), 2.59 (6H,s) \n\n Mass (m/z): 519,520,521,522 \n\n EXAMPLE 60 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-2-(ethoxy carbonyl)-1-pyrrolidinyl-2-oxoethyl-, dichloride (Compound No: 59) \n\n Yield: 28% \n\n m.p.: 118-120 C. \n\n IR (KBr,cm ^{ 1 } ): 1660,1510 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.75 (2H,s), 9.51 (2H,s), 9.20-9.10 (4H,m), 8.43-8.40 (2H,t), 5.97-5.83 (4H,m), 4.39-4.36 (2H,m), 4.27-4.22 (1 H,q), 4.12-4.05 (4H,m), 3.71-3.63 (4H,m), 3.48-3.40 (1 H,m), 2.26-2.19 (2H,m), 2.05-1.91 (5H,m), 1.30-1.27 (1H,t), 1.19-1.15 (5H,t) \n\n Mass (m/z): 609,610,611 \n\n EXAMPLE 61 \n\n Pyridinium, 3-(aminocarbonyl)-1-(2-oxo-2-thien-2-yl-ethyl)-5-2-1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-ylcarbonylhydrazinocarbonyl-, dichloride (Compound No: 60) \n\n Yield: 54% \n\n m.p.: Above 127-129 C.(dec) \n\n IR (KBr,cm ^{ 1 } ): 1678,1513 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.86 (2H,s), 9.83-9.64 (4H,t), 9.24-9.23 (2H,s), 8.82 (1H,s), 8.48-8.45 (1H,t), 8.34 (1H,s), 8.26-8.24 (4H,m), 7.44-7.42 (2H,d), 6.52-6.46 (4H,d) \n\n Mass (m/z): 534,535,536 \n\n EXAMPLE 62 \n\n Pyridinium, 1-2-4-(ethoxycarbonyl)-3-thiazolidinyl-2-oxoethyl-3-2-(methylsulfonyl)hydrazinocarbonyl-, chloride (Compound No: 61) \n\n Yield: 29% \n\n m.p.: 190-192 C. \n\n IR (KBr,cm ^{ 1 } ): 1673,1541 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.50 (1H,s), 9.55 (1H,s), 9.48 (1H,s), 9.12-9.08 (2H,m), 8.39-8.34 (1H,t), 6.04-5.99 (2H,m), 4.94-4.91 (1H,m), 4.87-4.84 (1H,d), 4.73-4.71 (1H,d), 4.28-4.23 (1H,q), 4.14-4.09 (1H,q), 3.43-3.38 (1H,m), 3.27-3.22 (1H,m), 3.10 (3H,s), 1.30-1.27 (1H,t), 1.20-1.17 (2H,m) \n\n Mass (m/z): 439,440,441 \n\n EXAMPLE 63 \n\n Pyridinium, 3,3-(hydrazodicarbonyl)bis1-2-(5-chloro-2-thienyl)-2-oxoethyl-, dichloride (Compound No: 62) \n\n Yield: 35% \n\n m.p.: Above 200-205 C. (dec) \n\n IR (KBr,cm ^{ 1 } ): 1674,1590,1500 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.90 (2H,s), 9.64-9.61 (2H,d), 9.29-9.20 (4H,m), 8.47-8.44 (2H,t), 8.18-8.17 (2H,d), 7.51-7.50 (2H,d), 6.49-6.48 (4H,s) \n\n Mass (m/z): 559,560,561,562,563,564 \n\n EXAMPLE 64 \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-(5-methyl-2-thienyl)-2-oxoethyl-, chloride (Compound No: 63) \n\n Yield: 22% \n\n m.p.: 196-198 C. \n\n IR(KBr,cm ^{ 1 } ): 1689,1657 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.47 (1H,s), 9.98 (1H,s), 9.53(1H,s), 9.17-9.16 (1H,d), 9.09-9.07 (1H,d), 8.42-8.38 (1H,t), 8.06-8.05 (1H,d), 7.15-7.14 (1H,d), 6.41 (2H,s), 3.09 (3H,s), 2.59 (3H,s) \n\n Mass (m/z): 354,355,356,357 \n\n EXAMPLE 65 \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-(4-nitro-2-thienyl)-2-oxoethyl-, bromide (Compound No: 64) \n\n Yield: 52% \n\n m.p.: Above 200-205 C.(dec) \n\n IR (KBr,cm ^{ 1 } ): 1688,1631,1541 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.41 (1H,s), 9.50 (1 H,s), 9.309-9.306 (1H,d), 9.17-9.15 (1H,d), 9.09-9.07 (1H,d), 8.866-8.862 (1H,d), 8.45-8.41 (1H,t), 6.50 (2H,s), 3.09 (3H,s) \n\n Mass (m/z): 385,386,387 \n\n EXAMPLE 66 \n\n Pyridinium, 1-2-oxo-2-(phenylamino)ethyl-3-(2-phenylhydrazino)carbonyl-, chloride (Compound No: 65) \n\n Yield: 45% \n\n m.p.: 165-167 C. \n\n IR (KBr,cm ^{ 1 } ): 1679,1626,1600,1497 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.18 (1H,s), 11.10 (1H,s), 9.62 (1 H,s), 9.24-9.22 (1 H,d), 9.17-9.15 (1 H,d), 8.40-8.36 (1 H,t), 8.19 (1H,s), 7.63-7.61 (2H,d), 7.37-7.33 (2H,t), 7.20-7.16 (2H,t), 7.12-7.09 (1H,t), 6.88-6.86 (2H,d), 6.78-6.74 (1H,t), 5.78 (2H,s) \n\n Mass (m/z): 347,348,349 \n\n EXAMPLE 67 \n\n Pyridinium, 4-2-(benzoyloxy)ethylaminocarbonyl-1-2-oxo-2-(phenylamino)ethyl-, chloride (Compound No: 66) \n\n Yield: 40% \n\n m.p.: 178-180 C. \n\n IR (KBr,cm ^{ 1 } ): 1700,1666,1559 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.13 (1H,s), 9.74-9.71 (1H,t), 9.23-9.22 (2H,d), 8.52-8.50 (2H,d), 8.01-7.99 (2H,d), 7.68-7.60 (3H,m), 7.54-7.51 (2H,t), 7.36-7.32 (2H,t), 7.12-7.08 (1H,t), 5.75 (2H,s), 4.47-4.45 (2H,t), 3.77-3.72 (2H,q). \n\n Mass (m/z): 404,405,406 \n\n EXAMPLE 68 \n\n Pyridinium, 3-2-(methylsulfonyl)hydrazinocarbonyl-1-2-(5-nitro-2-thienyl)-2-oxoethyl-, chloride (Compound No: 67) \n\n Yield: 10% \n\n m.p.: Above 105-110 C.(dec) \n\n IR (KBr,cm ^{ 1 } ): 1680,1620 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.48 (1H,s), 9.98 (1H,s), 9.52 (1H,s), 9.16-9.10 (2H,m), 8.45-8.41 (1H,t), 8.35-8.34 (1H,d), 8.25-8.24 (1H,d), 6.50 (2H,s), 3.09 (3H,s). \n\n Mass (m/z): 385,386,387 \n\n EXAMPLE 69 \n\n Pyridinium, 1-2-oxo-2-(2-thienyl)ethyl-3-2-(trifluoromethyl)sulfonylhydrazinocarbonyl-, bromide (Compound No: 68) \n\n Yield: 22% \n\n m.p.: 77-79 C. \n\n IR (KBr,cm ^{ 1 } ): 2960, 1690, 1673, 1591 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.76 (1H,s), 11.27 (1H,s), 9.61 (1H,s), 9.20-9.19 (1H,d), 9.07-9.05 (1H,d), 8.44-8.41 (1H,t), 8.25-8.22 (2H,m), 7.34-7.41 (1H,m), 6.46 (2H,s). \n\n Mass (m/z): 394, 395, 396 \n\n EXAMPLE 70 \n\n Pyridinium, 1-2-oxo-2-(2-thienyl)ethyl-3-(2-phenylhydrazino)carbonyl-, bromide (Compound No. 69) \n\n Yield: 10% \n\n m.p.: 192-194 C. \n\n IR (KBr,cm ^{ 1 } ): 1669,1663,1603, \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 10.99 (1H,s), 9.54 (1H,s), 9.17-9.14 (2H,t), 8.44-8.41 (1H,t), 8.25-8.22 (3H,m), 7.43-7.41 (1H,t), 7.20-7.16 (2H,t), 6.87-6.85 (2H,d), 6.79-6.75 (1H,t), 6.46 (2H,s) \n\n Mass (m/z): 338,339,340 \n\n EXAMPLE 71 \n\n Pyridinium, 3-2-(4-methoxyphenyl)sulfonylhydrazinocarbonyl-1-2-oxo-2-(2-thienyl)ethyl-, bromide (Compound No. 70) \n\n Yield: 28% \n\n m.p.: 126-128 C. \n\n IR (KBr,cm ^{ 1 } ): 1672,1653,1596 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.34-11.33 (1H,d), 10.27-10.26 (1H,d), 9.34 (1H,s), 9.13-9.12 (1H,d), 8.94-8.92 (1H,d), 8.38-8.34(1H,t), 8.24-8.19 (2H,m), 7.82-7.75 (2H,m), 7.42-7.40 (1H,t), 7.07-7.04 (2H,d), 6.40 (2H,s), 3.81 (3H,s). \n\n Mass (m/z): 432,433,434 \n\n EXAMPLE 72 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(phenylamino)carbonylhydrazinocarbonyl-, bromide (Compound No. 71) \n\n Yield: 25% \n\n m.p.: 183-185 C. \n\n IR (KBr,cm ^{ 1 } ): 1746,1717,1682 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.02 (1H,s), 9.57 (1H,s), 9.22-9.21 (1 H,d), 9.11-9.09 (1 H,d), 9.00 (1H,s), 8.57 (1H,s), 8.44-8.41 (1H,m), 7.47-7.45 (2H,d), 7.29-7.25 (2H,t), 7.00-6.96 (1H,t), 5.74 (2H,s), 4.28-4.23 (2H,q), 1.28-1.25 (3H,t). \n\n Mass (m/z): 343,344,345,346 \n\n EXAMPLE 73 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-2-(4-methylphenyl)sulfonylhydrazinocarbonyl-, bromide (Compound No. 72) \n\n Yield: 54% \n\n m.p.: 174-176 C. \n\n IR (KBr,cm ^{ 1 } ): 1746,1712,1634 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.33 (1H,s), 10.36 (1H,s), 9.37 (1H,s), 9.18-9.16 (1H,d), 8.93-8.91 (1H,d), 8.37-8.33 (1H,t), 7.78-7.76 (2H,d), 7.37-7.35 (2H,d), 5.68 (2H,s), 4.26-4.20 (2H,q), 2.37 (3H,s), 1.27-1.23 (3H,t). \n\n Mass (m/z): 378,379,380,381 \n\n EXAMPLE 74 \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-2-(phenylamino)carbonylhydrazinocarbonyl-, bromide (Compound No. 73) \n\n Yield: 70% \n\n m.p.: 206-208 C. \n\n IR (KBr,cm ^{ 1 } ): 1713,1684,1634 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.05 (1H,s), 9.55 (1H,s), 9.18-9.13 (2H,m), 9.02 (1H,s), 8.59 (1H,s), 8.49-8.45 (1H,m), 8.09-8.07 (2H,d), 7.84-7.80 (1H,t), 7.71-7.67 (2H,t), 7.49-7.47 (2H,d), 7.30-7.26 (2H,t), 7.01-6.97 (1H,t), 6.56 (2H,s). \n\n Mass (m/z): 375,376,377 \n\n EXAMPLE 75 \n\n Pyridinium, 1-2-oxo-2-(phenylamino)ethyl-3-2-(phenylmethyl)sulfonylhydrazinocarbonyl-, chloride (Compound No. 74) \n\n Yield: 48% \n\n m.p.: 208-210 C. \n\n IR (KBr,cm ^{ 1 } ): 1712,1681,1632 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.46 (1H,s), 10.80 (1H,s), 9.59 (1H,s), 9.22-9.20 (1H,d), 9.08-9.06 (1H,d), 8.38-8.36 (1H,t), 7.60-7.58 (2H,d), 7.49 (2H,m), 7.39-7.34 (5H,m), 7.13-7.10 (1H,t), 5.74(2H,s), 4.52 (2H,s). \n\n Mass (m/z): 425,426,427,428 \n\n EXAMPLE 76 \n\n Pyridinium, 4-2-(methylsulfonyl)hydrazinocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No. 75) \n\n Yield: 10% \n\n m.p: 190-192 C. \n\n IR (KBr,cm ^{ 1 } ): 1679,1630,1650 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.54 (1H,s), 10.03 (1H,s), 9.20-9.18 (2H,d), 8.59-8.57 (2H,d), 8.10-8.08 (2H,d), 7.84-7.80 (1H,t), 7.71-7.67 (2H,t), 6.56 (2H,s), 3.08 (3H,s). \n\n Mass (m/z): 334,335,336 \n\n EXAMPLE 77 \n\n Pyridinium, 1-(2-oxo-2-phenylethyl)-3-(2-phenylhydrazino)carbonyl-, bromide (Compound No. 76) \n\n Yield: 36% \n\n m.p.: 204-206 C. \n\n IR (KBr,cm ^{ 1 } ): 1686,1653,1630 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.01 (1H,s), 9.53 (1H,s), 9.17-9.16 (2H,m), 8.46-8.42 (1H,t), 8.09-8.07 (2H,d), 7.82-7.78 (1H,t), 7.69-7.65 7.65 (2H,t), 7.20-7.16 (2H,t), 6.88-6.86 (2H,d), 6.79-6.75 (1H,t), 6.56 (2H,s) \n\n Mass (m/z): 332,333 \n\n EXAMPLE 78 \n\n Pyridinium, 4-2-(benzoyloxy)ethylaminocarbonyl-1-(2-ethoxy-2-oxoethyl)-, bromide (Compound No. 77) \n\n Yield: 82% \n\n m.p.: 154-156 C. \n\n IR (KBr,cm ^{ 1 } ): 1742,1719,1707,1675 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 9.57-9.54 (1H,t), 9.22-9.20 (2H,d), 8.51-8.49 (2H,d), 8.00-7.98 (2H,d), 7.68-7.64 (1H,t), 7.54-7.51 (2H,t), 5.72 (2H,s), 4.47-4.44 (2H,t), 4.27-4.21 (2H,q), 3.76-3.72 (2H,q), 1.27-1.24 (3H,t) \n\n Mass (m/z): 357,358,359. \n\n EXAMPLE 79 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-(2-phenylhydrazino)carbonyl-, bromide (Compound No. 78) \n\n Yield: 37% \n\n m.p.: 185-187 C. \n\n IR (KBr,cm ^{ 1 } ): 1740,1690,1630. \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.01 (1H,s), 9.58 (1H,s), 9.23-9.14 (2H,m), 8.42-8.39 (1H,t), 8.19 (1H,s), 7.20-7.16 (2H,t), 6.87-6.85 (2H,d), 6.78-6.75 (1H,t), 5.75 (2H,s), 4.28-4.22 (2H,q), 1.28-1.24 (3H,t) \n\n Mass (m/z): 300,301,302. \n\n EXAMPLE 80 \n\n Pyridinium, 3-2-(4-methoxyphenyl)sulfonylhydrazinocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No. 79) \n\n Yield: 59% \n\n m.p.: 188-190 C. \n\n IR (KBr,cm ^{ 1 } ): 1671,1634,1580. \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.26-11.25 (1H,d), 10.17-10.16 (1H,d), 9.24 (1H,s), 9.03-9.01 (1H,d), 8.87-8.85 (1H,d), 8.31-8.27 (1H,t), 7.97-7.96 (2H,d), 7.74-7.69 (3H,m), 7.60-7.56 (2H,t), 6.99-6.97 (2H,d), 6.40 (2H,s), 3.73 (3H,s). \n\n Mass (m/z): 426,427,428,429 \n\n EXAMPLE 81 \n\n Pyridinium, 4-2-(benzoyloxy)ethylaminocarbonyl-1-(2-oxo-2-phenylethyl)-, bromide (Compound No. 80) \n\n Yield: 92% \n\n m.p.: 202-204 C. \n\n IR (KBr,cm ^{ 1 } ): 1715,1692,1650 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 9.55 (1H,s), 9.14-9.13 (2H,d), 8.52-8.51 (2H,d), 8.07-7.99 (4H,m), 7.80-7.51 (6H,m), 6.52 (2H,s), 4.46 (2H,s), 3.76-3.75 (2H,s). \n\n Mass (m/z): 389,390,391,392 \n\n EXAMPLE 82 \n\n Pyridinium, 1-(2-ethoxy-2-oxoethyl)-4-2-(methylsulfonyl)hydrazinocarbonyl-, bromide (Compound No. 81) \n\n Yield: 45% \n\n m.p.: 94-96 C. \n\n IR (KBr,cm ^{ 1 } ): 1726,1681,1643 \n\n ^{ 1 } HNMR (DMSO d _{ 6 } , 400 MHz) : 11.49 (1H,s), 9.98 (1H,s), 9.23-9.21 (2H,d), 8.54-8.52 (2H,d), 5.73 (2H,s), 4.28-4.22 (2H,q), 3.09 (3H,s), 1.28-1.25 (3H,t). \n\n Mass (m/z): 302,303,304,305. \n\n PHARMACEUTICAL COMPOSITIONS \n\n Pharmaceutical compositions may be prepared with a pharmaceutically effective quantity of compounds of general formula I, individually or in combination. The following pharmaceutical formulations suggested are by way of example alone and in no way restrict the forms in which they can be used. \n\n Oral Formulations \n\n Oral formulations may be administered as solid dosage forms for example pellets, powders, sachets or discreet units such as tablets or capsules and like. Other orally administered pharmaceutical preparations include monophasic and biphasic liquid dosage forms either in ready to use form or forms suitable for reconstitution such as mixtures, syrups, suspensions or emulsions. The preparations in addition may contain diluents, dispersing agents, buffers, stabilizers, solubilizers, surfactants, preservatives, chelating agents and/or other pharmaceutical additives as are used. Aqueous or non aqueous vehicle or their combination may be used and if desired may contain suitable sweetener, flavoring agent or similar substances. In case of suspension or emulsion a suitable thickening agent or suspending agent or emulsifying agent may be present in addition. Alternatively, the compounds may be administered as such in their pure form unassociated with other additives for example as capsules or sachets. It may also be administered with a vehicle. Pharmaceutical preparations can have a slow, delayed or controlled release of active ingredients as is provided by a matrix or diffusion controlled system. \n\n When the present invention or its salts or suitable complexes is presented as a discreet unit dosage form like tablet, it may contain in addition medically inert excipients as are used in the art. Diluents such as starch, lactose, dicalcium phosphate, talc, magnesium stearate, polymeric substances like methyl cellulose, fatty acids and derivatives, sodium starch glycollate, etc. may also be used. \n\n EXAMPLE 83 \n\n Preparation of Oral Dosage Form \n\n A typical tablet has the following composition: \n\n Active ingredient of formula I as given above \n\n Lactose 135 mg \n\n Starch 76 mg \n\n Polyvinyl pyrolidone (K-30) 2 mg \n\n Talc 1.5 mg \n\n Magnesium Stearate 1.0 mg \n\n Parenteral Formulations \n\n For parenteral administration, the compounds or their salts or suitable complexes thereof may be present in a sterile vehicle which may be an aqueous or non aqueous vehicle or a combination thereof. The examples of vehicles are water, ethyl oleate, oils and derivatives of polyols, glycols and their derivatives. It may contain additives common in injectable preparations like stabilizers, solubilizers, pH modifiers, buffers, antioxidants, cosolvents, complexing agents, tonicity modifiers, etc. \n\n Some suitable additives are for example tartrate, citrate or similar buffers, alcohol, sodium chloride, dextrose and high molecular weight polymers. Another alternative is sterile powder reconstitution. The compound may be administered in the form of injection for more than once daily administration, or intravenous infusion/drip or suitable depot preparation. \n\n EXAMPLE 84 \n\n Preparation Suitable for Parenteral Administration has the Following Composition \n\n Active ingredient of formula I as given above \n\n Polyethylene glycol (400) 0.75 ml \n\n Sodium metabisulphite 0.01% \n\n Isotonic saline/WFI q.s. \n\n Other Formulations \n\n For the dermatological application and for the discoloration of teeth, the recommended formulations are lotions, oral rinse and toothpaste containing appropriate amount of the compounds of the general formula I. \n\n The above examples are presented by way of illustration alone and in no way limit the scope of the invention. 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ALANGUDI","valueNormalised":"Sankaranarayanan Alangudi"},"inventorship":null}],"inventorships":[],"unmatchedInventorships":[],"activeUserHasInventorship":false},"simpleFamilyId":207145428,"citesPatentCount":2,"countrySpec":{"countryName":"USA","description":"GRANTED PATENT AS SECOND PUBLICATION [FROM 2001 ONWARDS]","rule":"pubdate:AFTER:01-01-2001","docType":"GRANTED_PATENT"},"pageTitle":"US 6608094 B2 - Compounds for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof","documentTitle":"Compounds for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof"},"claims":{"source":"xml_claims","claims":[{"lines":["What is claimed is:"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["A compound represented by general formula (I), or a pharmaceutically acceptable salt thereof wherein
Y is —C(O)R 1 ;
R 1 is —R 4 —R 5 or —N(R 7 )N(R 7 )R 9 ;
R 4 is selected from the group consisting of —N(R 7 )R 6 O—, —N(R 7 )R 6 N(R 7 )—, —OR 6 O—, and —OR 6 N(R 7 )—, where R 6 is alkyl with C 2 -C 8 carbon atoms;
R 5 is selected from the group consisting of alkyl, aryl containing up to two conjugated or fused ring systems including heteroaryl, —COR 7 , —SO 2 R 7 , —C(S)NHR 7 , —C(NH)NHR 7 , —COR 10 , and —C(O)NHR 7 where R 7 is selected from the group consisting of H, alkyl and aryl containing up to two conjugated or fused ring systems including heteroaryl, provided R 7 may be the same or different for R 1 and R 3 in the same compound;
R 2 is selected from the group consisting of F, Cl, Br, I, OR 7 , NO 2 , alkyl, aryl containing up to two conjugated or fused ring systems including heteroaryl, formyl, acyl, C(O)NR 7 R 10 , C(O)OR 7 , NR 7 R 10 , SR 7 , SO 2 NH 2 , SO 2 alkyl and SO 2 aryl;
m is 0, 1 or 2;
R is —CH 2 —C(O)—R 3 ;
R 3 is selected from the group consisting of R 7 , —O-alkyl, —O-aryl, N(R 7 )(R 10 ), N(R 7 )N(R 7 )(R 10 ), and CH(R 7 )C(O)R 8 where R 8 is selected from the group consisting of R 7 , OR 7 and NR 7 R 10 ;
R 9 is selected from the group consisting of hydrogen, alkyl, aryl containing up to two conjugated or fused ring systems including heteroaryl, —C(O)R 10 , —SO 2 R 10 , —C(S)NHR 10 , —C(NH)NH(R 10 ) and —C(O)NHR 10 ;
R 10 is selected from the group consisting of H, alkyl and aryl containing up to two conjugated or fused ring systems including heteroaryl and in each case may be the same or different from substituent R 7 , provided R 10 may be the same or different for R 1 and R 3 in the same compound;
X is selected from group consisting of a halide ion, acetate ion, perchlorate ion, sulfonate ion, oxalate ion, citrate ion, tosylate ion, maleate ion, mesylate ion, carbonate ion, sulfite ion, phosphoric hydrogen ion, phosphonate ion, phosphate ion, BF 4 − and PF 6 − ; with proviso that,
(i) when two alkyl groups are present on the same carbon or nitrogen, they may be linked together to form a cyclic structure; and
(ii) the nitrogen of heteroaryl ring of R 10 , when present, may be quaternized with a compound X—CH 2 —C(O)—R 3 , where X and R 3 have the meaning as given above."],"number":1,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 1 , wherein —C(O)R 1 group is at position 3 or 4."],"number":2,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 2 , wherein the position for —C(O)R 1 group is at position 3."],"number":3,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 1 , wherein m is 0 or 1."],"number":4,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 2 , wherein m is 0 or 1."],"number":5,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 3 , wherein m is 0 or 1."],"number":6,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 1 , wherein m is 0."],"number":7,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 2 , wherein m is 0."],"number":8,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 3 , wherein m is 0."],"number":9,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 1 , wherein X is a halide ion."],"number":10,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 1 , which is selected from the group consisting of the following compounds:
(aa) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(2-furanyl)-2-oxoethyl]-, dibromide or a pharmaceutically acceptable salt thereof,
(ab) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ac) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(cyclopropylamino)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ad) Pyridinium, 3-[[(2-methoxyethyl)amino]carbonyl]-1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ae) Pyridinium, 3-bromo-5-[[2-(methoxyethyl)amino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(af) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ag) Pyridinium, 3-[[2-[(2-chloro-3-pyridinyl)carbonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ah) Pyridinium, 1-[2-(cyclopropylamino)-2-oxoethyl]-3-[[(2-methoxyethyl)amino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ai) Pyridinium, 1-[2-[(1-methylethyl)amino]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(aj) Pyridinium, 3-[[2-(3-cyclohexyl-1-oxopropyl)hydrazino]carbonyl]-1-[2-oxo-2-(phenylamino)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ak) Pyridinium, 3-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide, or a pharmaceutically acceptable salt thereof,
(al) Pyridinium, 3-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(4-ethoxy-2,4-dioxobutyl)-, chloride or a pharmaceutically acceptable salt thereof, and
(am) Pyridinium, 3-[[2-[[6-(methoxycarbonyl)-3-pyridinyl]carbonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof."],"number":11,"annotation":false,"title":false,"claim":true},{"lines":["The compound as claimed in claim 1 , which is selected from the group consisting of the following compounds:
(an) Pyridinium, 3-(aminocarbonyl)-1-(2-oxo-2-thien-2-yl-ethyl)-5-[[2-[[1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-yl]carbonyl]hydrazino]carbonyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ao) Pyridinium, 1-[2-oxo-2-(2-thienyl)ethyl]-3-[[2-[(trifluoromethyl)sulfonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ap) Pyridinium, 2-methyl-1-(2-oxo-2-thien-2-yl-ethyl)-5-[[2-[[1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-yl]carbonyl]hydrazino]carbonyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(aq) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(5-methyl-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ar) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(5-chloro-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(as) Pyridinium, 2-methyl-5-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-(2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(at) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(4-nitro-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(au) Pyridinium, 1-[2-oxo-2-(phenylamino)ethyl]-3-[(2-phenylhydrazino)carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(av) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(4-nitro-2-thienyl)-2-oxoethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(aw) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(5-nitro-2-thienyl)-2-oxoethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ax) Pyridinium, 1-[2-(5-chloro-2-thienyl)-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(az) Pyridinium, 3-[[2-[(1-methylethyl)sulfonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ba) Pyridinium, 3-bromo-5-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bb) Pyridinium, 1-[2-[2-(ethoxycarbonyl)-1-pyrrolidinyl]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bc) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(5-methyl-2-thienyl)-2-oxoethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bd) Pyridinium, 1-[2-[4-(ethoxycarbonyl)-3-thiazolidinyl]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(be) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-[4-(phenylmethyl)-1-piperidinyl]ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bf) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-[2-(ethoxy carbonyl)-1-pyrrolidinyl]-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(bg) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-[2-oxo-2-(phenylamino)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bh) Pyridinium, 1-[2-oxo-2-(2-thienyl)ethyl]-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bi) Pyridinium, 3-[[2-[(4-methoxyphenyl)sulfonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bj) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[[2-[(phenylamino)carbonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bk) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[[2-[(4-methylphenyl)sulfonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bl) Pyridinium, 1-(2-oxo-2-phenylethyl)-3-[[2-[(phenylamino)carbonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bm) Pyridinium, 1-[2-oxo-2-(phenylamino)ethyl]-3-[[2-[(phenylmethyl)sulfonyl]hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bn) Pyridinium, 4-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bo) Pyridinium, 1-(2-oxo-2-phenylethyl)-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bp) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(2-ethoxy-2-oxoethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bq) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(br) Pyridinium, 3-[[2-[(4-methoxyphenyl)sulfonyl]hydrazino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bs) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof, and
(bt) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-4-[[2-(methylsulfonyl)hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof."],"number":12,"annotation":false,"title":false,"claim":true},{"lines":["A process for the preparation of a compound represented by general formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof, which comprises providing a substituted pyridine having a backbone structure the same as the compound of general formula (I) or a pharmaceutically acceptable salt thereof that is to be prepared, followed by quaternizing the substituted pyridine with a quaternizing reagent in an alcoholic and/or high boiling solvent under reflux for 6-48 hrs. to give the desired compound represented by general formula (I) or a pharmaceutically acceptable salt thereof."],"number":13,"annotation":false,"title":false,"claim":true},{"lines":["A pharmaceutical composition comprising a pharmaceutically effective amount of one or more compounds represented by general formula (I), as defined in claim 1 or pharmaceutically acceptable salt(s) thereof in admixture with a pharmaceutically acceptable carrier, diluent, solvent or excepient."],"number":14,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 14 in the form of an oral formulation."],"number":15,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 14 , wherein said acceptable carrier, diluent, solvent or excepient is selected from group consisting of starch, lactose, polyvinyl pyrolidone (K-30), talc and magnesium stearate."],"number":16,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 14 in the form of a parenteral formulation."],"number":17,"annotation":false,"title":false,"claim":true},{"lines":["A method for the preparation of a parenteral formulation as claimed in claim 17 , which comprises dissolving one or more compounds represented by general formula (I), as defined in claim 1 or pharmaceutically acceptable salt(s) thereof, in polyethylene glycol 400 and diluting the solution so obtained with an isotonic solution or water to a desired concentration."],"number":18,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 14 in the form of a lotion, oral rinse and toothpaste."],"number":19,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 14 , wherein said compound is selected from the group consisting of:
(aa) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(2-furanyl)-2-oxoethyl]-, dibromide or a pharmaceutically acceptable salt thereof,
(ab) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ac) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(cyclopropylamino)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ad) Pyridinium, 3-[[(2-methoxyethyl)amino]carbonyl]-1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ae) Pyridinium, 3-bromo-5-[[2-(methoxyethyl)amino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(af) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ag) Pyridinium, 3-[[2-[(2-chloro-3-pyridinyl)carbonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ah) Pyridinium, 1-[2-(cyclopropylamino)-2-oxoethyl]-3-[[(2-methoxyethyl)amino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ai) Pyridinium, 1-[2-[(1-methylethyl)amino]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(aj) Pyridinium, 3-[[2-(3-cyclohexyl-1-oxopropyl)hydrazino]carbonyl]-1-[2-oxo-2-(phenylamino)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ak) Pyridinium, 3-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(al) Pyridinium, 3-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(4-ethoxy-2,4-dioxobutyl)-, chloride or a pharmaceutically acceptable salt thereof, and
(am) Pyridinium, 3-[[2-[[6-(methoxycarbonyl)-3-pyridinyl]carbonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof."],"number":20,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 14 , wherein said compound is selected from the group consisting of:
(an) Pyridinium, 3-(aminocarbonyl)-1-(2-oxo-2-thien-2-yl-ethyl)-5-[[2-[[1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-yl]carbonyl]hydrazino]carbonyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ao) Pyridinium, 1-[2-oxo-2-(2-thienyl)ethyl]-3-[[2-[(trifluoromethyl)sulfonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof, (ap) Pyridinium, 2-methyl-1-(2-oxo-2-thien-2-yl-ethyl)-5-[[2-[[1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-yl]carbonyl]hydrazino]carbonyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(aq) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(5-methyl-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ar) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(5-chloro-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(as) Pyridinium, 2-methyl-5-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(at) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(4-nitro-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(au) Pyridinium, 1-[2-oxo-2-(phenylamino)ethyl]-3-[(2-phenylhydrazino)carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(av) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(4-nitro-2-thienyl)-2-oxoethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(aw) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(5-nitro-2-thienyl)-2-oxoethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ax) Pyridinium, 1-[2-(5-chloro-2-thienyl)-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(az) Pyridinium, 3-[[2-[(1-methylethyl)sulfonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ba) Pyridinium, 3-bromo-5-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bb) Pyridinium, 1-[2-[2-(ethoxycarbonyl)-1-pyrrolidinyl]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bc) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(5-methyl-2-thienyl)-2-oxoethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bd) Pyridinium, 1-[2-[4-(ethoxycarbonyl)-3-thiazolidinyl]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(be) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-[4-(phenylmethyl)-1-piperidinyl]ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bf) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-[2-(ethoxy carbonyl)-1-pyrrolidinyl]-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(bg) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-[2-oxo-2-(phenylamino)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bh) Pyridinium, 1-[2-oxo-2-(2-thienyl)ethyl]-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bi) Pyridinium, 3-[[2-[(4-methoxyphenyl)sulfonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bj) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[[2-[(phenylamino)carbonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bk) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[[2-[(4-methylphenyl)sulfonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bl) Pyridinium, 1-(2-oxo-2-phenylethyl)-3-[[2-[(phenylamino)carbonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bm) Pyridinium, 1-[2-oxo-2-(phenylamino)ethyl]-3-[[2-[(phenylmethyl)sulfonyl]hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bn) Pyridinium, 4-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bo) Pyridinium, 1-(2-oxo-2-phenylethyl)-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bp) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(2-ethoxy-2-oxoethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bq) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(br) Pyridinium, 3-[[2-[(4-methoxyphenyl)sulfonyl]hydrazino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bs) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof, and
(bt) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-4-[[2-(methylsulfonyl)hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof."],"number":21,"annotation":false,"title":false,"claim":true},{"lines":["A method for treating a diabetic patient by breaking a preformed AGE, within said patient, which comprises, administering an effective amount of a compound represented by general formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof, either singly or in combination with other drugs for antidiabetic therapy."],"number":22,"annotation":false,"title":false,"claim":true},{"lines":["A method of preventing or treating diseases caused by diabetes and aging related complications including vascular and neuro-vascular complications, which comprises, administering to a patient in need thereof, an effective amount of a compound represented by general formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof, either singly or in combination with a pharmaceutically acceptable carrier, diluent or excepient."],"number":23,"annotation":false,"title":false,"claim":true},{"lines":["The method as claimed in claim 23 , wherein the disease prevented or treated is a nephrological disorder, neurological disorder, atherosclerosis, retinal disorder, dermatological disorder, non-enzymatic browning of oral cavity, endothelial or other organ dysfunction and growth impairment."],"number":24,"annotation":false,"title":false,"claim":true},{"lines":["The method as claimed in claim 23 , wherein the disease prevented or treated is an inflammatory disorder, immunological disorder, or oxidative stress."],"number":25,"annotation":false,"title":false,"claim":true},{"lines":["The method as claimed in claim 22 , wherein said compound is selected from the group consisting of:
(aa) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(2-furanyl)-2-oxoethyl]-, dibromide or a pharmaceutically acceptable salt thereof,
(ab) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ac) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(cyclopropylamino)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ad) Pyridinium, 3-[[(2-methoxyethyl)amino]carbonyl]-1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ae) Pyridinium, 3-bromo-5-[[2-(methoxyethyl)amino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(af) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ag) Pyridinium, 3-[[2-[(2-chloro-3-pyridinyl)carbonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ah) Pyridinium, 1-[2-(cyclopropylamino)-2-oxoethyl]-3-[[(2-methoxyethyl)amino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ai) Pyridinium, 1-[2-[(1-methylethyl)amino]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(aj) Pyridinium, 3-[[2-(3-cyclohexyl-1-oxopropyl)hydrazino]carbonyl]-1-[2-oxo-2-(phenylamino)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ak) Pyridinium, 3-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(al) Pyridinium, 3-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(4-ethoxy-2,4-dioxobutyl)-, chloride or a pharmaceutically acceptable salt thereof, and
(am) Pyridinium, 3-[[2-[[6-(methoxycarbonyl)-3-pyridinyl]carbonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof."],"number":26,"annotation":false,"title":false,"claim":true},{"lines":["The method as claimed in claim 22 , wherein said compound is selected from the group consisting of:
(an) Pyridinium, 3-(aminocarbonyl)-1-(2-oxo-2-thien-2-yl-ethyl)-5-[[2-[[1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-yl]carbonyl]hydrazino]carbonyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ao) Pyridinium, 1-[2-oxo-2-(2-thienyl)ethyl]-3-[[2-[(trifluoromethyl)sulfonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ap) Pyridinium, 2-methyl-1-(2-oxo-2-thien-2-yl-ethyl)-5-[[2-[[1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-yl]carbonyl]hydrazino]carbonyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(aq) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(5-methyl-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ar) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(5-chloro-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(as) Pyridinium, 2-methyl-5-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(at) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(4-nitro-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(au) Pyridinium, 1-[2-oxo-2-(phenylamino)ethyl]-3-[(2-phenylhydrazino)carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(av) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(4-nitro-2-thienyl)-2-oxoethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(aw) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(5-nitro-2-thienyl)-2-oxoethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ax) Pyridinium, 1-[2-(5-chloro-2-thienyl)-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(az) Pyridinium, 3-[[2-[(1-methylethyl)sulfonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ba) Pyridinium, 3-bromo-5-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bb) Pyridinium, 1-[2-[2-(ethoxycarbonyl)-1-pyrrolidinyl]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bc) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(5-methyl-2-thienyl)-2-oxoethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bd) Pyridinium, 1-[2-[4-(ethoxycarbonyl)-3-thiazolidinyl]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(be) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-[4-(phenylmethyl)-1-piperidinyl]ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bf) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-[2-(ethoxy carbonyl)-1-pyrrolidinyl]-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(bg) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-[2-oxo-2-(phenylamino)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bh) Pyridinium, 1-[2-oxo-2-(2-thienyl)ethyl]-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bi) Pyridinium, 3-[[2-[(4-methoxyphenyl)sulfonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bj) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[[2-[(phenylamino)carbonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bk) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[[2-[(4-methylphenyl)sulfonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bl) Pyridinium, 1-(2-oxo-2-phenylethyl)-3-[[2-[(phenylamino)carbonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bm) Pyridinium, 1-[2-oxo-2-(phenylamino)ethyl]-3-[[2-[(phenylmethyl)sulfonyl]hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bn) Pyridinium, 4-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bo) Pyridinium, 1-(2-oxo-2-phenylethyl)-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bp) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(2-ethoxy-2-oxoethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bq) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(br) Pyridinium, 3-[[2-[(4-methoxyphenyl)sulfonyl]hydrazino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bs) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof and
(bt) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-4-[[2-(methylsulfonyl)hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof."],"number":27,"annotation":false,"title":false,"claim":true},{"lines":["The method as claimed in claim 23 , wherein said compound is selected from the group consisting of:
(aa) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(2-furanyl)-2-oxoethyl]-, dibromide or a pharmaceutically acceptable salt thereof,
(ab) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ac) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(cyclopropylamino)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ad) Pyridinium, 3-[[(2-methoxyethyl)amino]carbonyl]-1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ae) Pyridinium, 3-bromo-5-[[2-(methoxyethyl)amino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(af) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ag) Pyridinium, 3-[[2-[(2-chloro-3-pyridinyl)carbonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ah) Pyridinium, 1-[2-(cyclopropylamino)-2-oxoethyl]-3-[[(2-methoxyethyl)amino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ai) Pyridinium, 1-[2-[(1-methylethyl)amino]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(aj) Pyridinium, 3-[[2-(3-cyclohexyl-1-oxopropyl)hydrazino]carbonyl]-1-[2-oxo-2-(phenylamino)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ak) Pyridinium, 3-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(al) Pyridinium, 3-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(4-ethoxy-2,4-dioxobutyl)-, chloride or a pharmaceutically acceptable salt thereof, and
(am) Pyridinium, 3-[[2-[[6-(methoxycarbonyl)-3-pyridinyl]carbonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, chloride or a pharmaceutically acceptable salt thereof."],"number":28,"annotation":false,"title":false,"claim":true},{"lines":["The method as claimed in claim 23 , wherein said compound is selected from the group consisting of:
(an) Pyridinium, 3-(aminocarbonyl)-1-(2-oxo-2-thien-2-yl-ethyl)-5-[[2-[[1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-yl]carbonyl]hydrazino]carbonyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ao) Pyridinium, 1-[2-oxo-2-(2-thienyl)ethyl]-3-[[2-[(trifluoromethyl)sulfonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ap) Pyridinium, 2-methyl-1-(2-oxo-2-thien-2-yl-ethyl)-5-[[2-[[1-(2-oxo-2-thien-2-yl-ethyl)pyridinium-3-yl]carbonyl]hydrazino]carbonyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(aq) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(5-methyl-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(ar) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(5-chloro-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(as) Pyridinium, 2-methyl-5-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(at) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-(4-nitro-2-thienyl)-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(au) Pyridinium, 1-[2-oxo-2-(phenylamino)ethyl]-3-[(2-phenylhydrazino)carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(av) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(4-nitro-2-thienyl)-2-oxoethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(aw) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(5-nitro-2-thienyl)-2-oxoethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(ax) Pyridinium, 1-[2-(5-chloro-2-thienyl)-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(az) Pyridinium, 3-[[2-[(1-methylethyl)sulfonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(ba) Pyridinium, 3-bromo-5-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bb) Pyridinium, 1-[2-[2-(ethoxycarbonyl)-1-pyrrolidinyl]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bc) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-(5-methyl-2-thienyl)-2-oxoethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bd) Pyridinium, 1-[2-[4-(ethoxycarbonyl)-3-thiazolidinyl]-2-oxoethyl]-3-[[2-(methylsulfonyl)hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(be) Pyridinium, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-[4-(phenylmethyl)-1-piperidinyl]ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bf) Pyridinium, 3,3′-(hydrazodicarbonyl)bis[1-[2-[2-(ethoxy carbonyl)-1-pyrrolidinyl]-2-oxoethyl]-, dichloride or a pharmaceutically acceptable salt thereof,
(bg) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-[2-oxo-2-(phenylamino)ethyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bh) Pyridinium, 1-[2-oxo-2-(2-thienyl)ethyl]-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bi) Pyridinium, 3-[[2-[(4-methoxyphenyl)sulfonyl]hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bj) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[[2-[(phenylamino)carbonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bk) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[[2-[(4-methylphenyl)sulfonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bl) Pyridinium, 1-(2-oxo-2-phenylethyl)-3-[[2-[(phenylamino)carbonyl]hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bm) Pyridinium, 1-[2-oxo-2-(phenylamino)ethyl]-3-[[2-[(phenylmethyl)sulfonyl]hydrazino]carbonyl]-, chloride or a pharmaceutically acceptable salt thereof,
(bn) Pyridinium, 4-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bo) Pyridinium, 1-(2-oxo-2-phenylethyl)-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(bp) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(2-ethoxy-2-oxoethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bq) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-3-[(2-phenylhydrazino)carbonyl]-, bromide or a pharmaceutically acceptable salt thereof,
(br) Pyridinium, 3-[[2-[(4-methoxyphenyl)sulfonyl]hydrazino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof,
(bs) Pyridinium, 4-[[[2-(benzoyloxy)ethyl]amino]carbonyl]-1-(2-oxo-2-phenylethyl)-, bromide or a pharmaceutically acceptable salt thereof, and
(bt) Pyridinium, 1-(2-ethoxy-2-oxoethyl)-4-[[2-(methylsulfonyl)hydrazino]carbonyl]-, bromide or a pharmaceutically acceptable salt thereof."],"number":29,"annotation":false,"title":false,"claim":true},{"lines":["The process as claimed in claim 13 , wherein the substituted pyridine is selected from the group consisting of:
N,N′-bis(nicotinyl)hydrazine,
3-[(2-pyridyl)hydrazinocarbonyl]pyridine,
3-[(2-methanesulfonyl)hydrazinocarbonyl]pyridine,
3-[(2-benzoyloxy)ethylaminocarbonyl]pyridine,
3-[(2-phenylsulfonyl)hydrazinocarbonyl]pyridine,
3-[(2-acetoxy)ethyloxycarbonyl]pyridine,
3-[(2-benzoyloxy)ethyloxycarbonyl]pyridine,
3-[(2-methoxy)ethyloxycarbonyl]pyridine,
3-[(2-phenylaminocarbonyl)hydrazinocarbonyl]pyridine,
3-[(2-acetoxy)ethylaminocarbonyl]pyridine,
3-[(2-(4-methylphenyl sulfonylhydrazinocarbonyl))]pyridine,
3-[(2-benzoyl)-hydrazino carbonyl]pyridine,
3-[(2-phenylmethane sulfonyl)hydrazino carbonyl]pyridine,
3-[(2-(3-cyclohexylpropanoyl)hydrazino carbonyl]pyridine,
3-[(2-methoxy)ethylaminocarbonyl]pyridine, and
3-[1-oxo-1-(2-methoxycarbonyl)pyridyl]hydrazino pyridine;and said quaternizing agent is selected from the group consisting of:
2-bromoacetyl thiophene,
2-chloroacetyl thiopene,
phenacylbromide,
phenacylchloride,
2,4-dichloropheanacylbromide,
N-phenyl chloroacetamide,
N-cyclopropyl chloroacetamide,
ethylbromoacetate,
bromo acetylfuran,
N-isopropylchloroacetamide,
N-chloroacetyl-2-pyrrolidinone, and
chloroacetic acid."],"number":30,"annotation":false,"title":false,"claim":true},{"lines":["Pyridinium, 3-[[2-(ethoxycarbonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof."],"number":31,"annotation":false,"title":false,"claim":true},{"lines":["A pharmaceutical composition comprising a pharmaceutically effective amount of the compound as claimed in claim 31 or pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable carrier, diluent, solvent or excepient."],"number":32,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 32 in the form of an oral formulation."],"number":33,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 32 , wherein said acceptable carrier, diluent, solvent or excepient is selected from the group consisting of starch, lactose, polyvinyl pyrolidone (K-30), talc and magnesium stearate."],"number":34,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 32 , in the form of a parenteral formulation."],"number":35,"annotation":false,"title":false,"claim":true},{"lines":["A method for preparation of a parenteral formulation as claimed in claim 35 , which comprises dissolving pyridinium, 3-[[2-(ethoxycarbonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]-, bromide or a pharmaceutically acceptable salt thereof in polyethylene glycol 400 and diluting the solution so obtained with an isotonic solution or water to a desired concentration."],"number":36,"annotation":false,"title":false,"claim":true},{"lines":["The pharmaceutical composition as claimed in claim 32 in the form of a lotion, oral rinse and toothpaste."],"number":37,"annotation":false,"title":false,"claim":true},{"lines":["A method for treating a diabetic patient by breaking a preformed AGE, within said patient, which comprises, administering an effective amount of the compound as claimed in claim 31 or pharmaceutically acceptable salt thereof, either singly, or in combination with other drugs for antidiabetic therapy."],"number":38,"annotation":false,"title":false,"claim":true},{"lines":["A method of preventing or treating diseases caused by diabetic and aging related complications including vascular and neuro-vascular complications which comprises administering to a patient in need thereof an effective amount of the compound as claimed in claim 31 or pharmaceutically acceptable salt thereof, either singly or in combination with a pharmaceutically acceptable carrier, diluent, solvent or excepient."],"number":39,"annotation":false,"title":false,"claim":true},{"lines":["The method as claimed in claim 39 , wherein the disease prevented or treated is a nephrological disorder, neurological disorder, atherosclerosis, retinal disorder, dermatological disorder, non-enzymatic browning of oral cavity, endothelial or other organ dysfunction and growth impairment."],"number":40,"annotation":false,"title":false,"claim":true},{"lines":["The method as claimed in claim 39 , wherein the disease prevented or treated is an inflammatory disorder, immunological disorder, or oxidative stress."],"number":41,"annotation":false,"title":false,"claim":true}]}},"filters":{"npl":[],"notNpl":[],"applicant":[],"notApplicant":[],"inventor":[],"notInventor":[],"owner":[],"notOwner":[],"tags":[],"dates":[],"types":[],"notTypes":[],"j":[],"notJ":[],"fj":[],"notFj":[],"classIpcr":[],"notClassIpcr":[],"classNat":[],"notClassNat":[],"classCpc":[],"notClassCpc":[],"so":[],"notSo":[],"sat":[]},"sequenceFilters":{"s":"SEQIDNO","d":"ASCENDING","p":0,"n":10,"sp":[],"si":[],"len":[],"t":[],"loc":[]}}