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for invention","granted":false,"earliest_filing_date":"2003-12-17","has_disclaimer":false,"patent_status":"PENDING","publication_count":2,"has_spc":false,"has_grant_event":false,"has_entry_into_national_phase":true},"abstract":{"en":[{"text":"The present invention provides a compound of formula (I), or a pharmaceutically acceptable salt thereof. These compounds are inhibitors of protein kinases, particularly inhibitors of PIM-1, CDK-2, GSK-3, and SRC mammalian protein kinases. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of utilizing those compounds and compositions in the treatment of various protein kinase mediated disorders.","lang":"en","source":"WIPO_FULLTEXT","data_format":"ORIGINAL"}],"fr":[{"text":"L'invention concerne un composé représenté par la formule (I), ou un sel pharmaceutiquement acceptable de celle-ci. Ces composés sont des inhibiteurs des protéine kinases, en particulier des protéine kinases de mammifères PIM-1, CDK-2, GSK-3, et SRC. L'invention concerne également des compositions pharmaceutiquement acceptables contenant les composés décrits et des méthodes d'utilisation de ces composés et compositions pour le traitement de divers troubles dans lesquels les protéine kinases interviennent comme médiateurs.","lang":"fr","source":"WIPO_FULLTEXT","data_format":"ORIGINAL"}]},"abstract_lang":["en","fr"],"has_abstract":true,"claim":{"en":[{"text":"CLAIMS 1. A compound of formula (I): (I) or a pharmaceutically acceptable salt thereof, wherein R 1 is OR 3 , SR 3 , or NR 3 R 4 ; wherein each occunence of R 3 and R 4 is independently (U) m R\\ wherein U is an optionally substituted Cι- 6 alkylidene chain, wherein up to two methylene units of the chain are optionally and independently replaced by -C(O)-, -C(O)C(O)-, -CONR-, -CONRNR-, -CO 2 -, -OC(O)-, -NRCO 2 -, -O-, - NRCONR-, -OC(O)NR-, -NRNR, -NRCO-, -S-, -SO-, -SO 2 -, -NR-, -SO 2 NR-, or- NRSO 2 -; m is 0 or 1; or wherein R 3 and R 4 , taken together with the nitrogen form an optionally substituted 5-8 membered heterocyclyl or heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur; each occunence of R is independently selected from hydrogen or an optionally substituted Cι- 6 aliphatic group, and each occunence of R' is independently selected from hydrogen or an optionally substituted group selected from Cι- 8 aliphatic, C 6 -ιo aryl, a heteroaryl ring having 5-10 ring atoms, or a heterocyclyl ring having 3-10 ring atoms, or wherein R and R' taken together, or two occunences of R' on the same substituent or different substituents, taken together, form a 5-8 membered heterocyclyl or heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and R 2 is -(T) n Ar 1 , wherein T is NR; n is 0 or 1; Ar 1 is a 3-7 membered saturated, partially unsaturated, or fully unsaturated monocyclic ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-10 membered saturated, partially unsaturated, or fully unsaturated bicyclic ring system having 0-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur; provided that: 9 1 1) when R is optionally substituted 1,3, 5-triazine, then R is not N-morpholino; 2) when R 2 is nitro substituted pyrazolyl, furyl, or thiophene, then R 1 is not NR 3 R 4 ; 3) when R 2 is furyl, then R 2 is not NH 2 ; 4) when R 2 is optionally substituted pyridyl or phenyl, then R 1 is not OR 3 , where R 3 is halogen substituted alkyl; 5) when R 2 is phenyl substituted with haloalkyl or haloalkoxy, then R 1 is not NH(C 1 - 4 alkyl) or O(CH 2 ) 2 N(Me) 2 ; 6) compounds of formula I exclude: a. Butanoic acid, 2-(benzylamino)-3[(3-phenyl-l,2,4-triazolo [4,3-b] pyridazin-6-yl) hydrazono] -methyl ester; b. Benzamide, N-[2,5-dihydro-3-methyl-5-oxo-l-(3-phenyl-l,2,4-trazolo [4,3- b] pyridazin-6-yl)-lH-pyrazol-4-yl]; and c. 2-propenoic acid, 2-(benzylamino)-3-[3,5-dimethyl-l-(3-phenyl-l,2,4- triazolo [4,3-b] pyridazin-6-yl)-lH-pyrazol-4-yl]-; 7) when R 2 is phenyl substituted with one or more occunences of OMe, Me, NO 2 , CI, or CF 3 , then R 1 is not optionally substituted morpholino or piperazinyl; 8) when R 2 is phenyl or fluoro-substituted phenyl, R 1 is not -O-CH 2 -(triazolyl); 9) when R 1 is -NH(cyclopropyl), then R 2 is not phenyl substituted with one occunence of CF 3 in the para position; 10) when R 2 is unsubstituted phenyl, then R 1 is not -SR 3 , wherein R 3 is phenyl substituted with CF 3 in the meta position, phenyl substituted with two occunences of OCH 3 , (CH 2 ) 2 OH, -(CH 2 )COOCH 2 CH 3 , or phenyl substituted with one occunence of CI in the para position; and 11) when R 2 is unsubstituted phenyl, then R 1 is not NH(CH)=NOH. 2. The compound of claim 1, wherein R 1 is NR 3 R 4 , OR 3 , or SR 3 , and compounds have one of the following general formulas II, III or IV: II III IV 3. The compound of claim 1, wherein n is 1, T is NR, and R 2 is -NRAr 1 , and compounds have one of the general formulas IIA, IIIA, or IVA: IIA IIIA IVA The compound of claim 1, wherein m is 0, and R is -Ar , and compounds have one of the general formulas IIB, IIIB, or IVB: IIB IIIB IVB 5. The compound of claim 1, wherein R 4 is hydrogen or optionally substituted - 4 alkyl and R is an optionally substituted aryl, heteroaryl, cycloaliphatic, or heterocycloaliphatic group. 6. The compound of claim 1, wherein R 4 is hydrogen or optionally substituted Ci- alkyl and R 3 is an optionally substituted 5- or 6-membered aryl or heteroaryl group. 7. The compound of claim 1, wherein R 4 is hydrogen or optionally substituted C\\. alkyl and R 3 is an optionally substituted 3-7-membered cycloaliphatic or heterocycloaliphatic group. 8. The compound of claim 1, wherein R 4 is hydrogen or optionally substituted Ci- 4 alkyl, and R 3 is an optionally substituted cyclic group selected from: u iii ιv VI vu Vlll IX X XI xu XVII XV111 XIX XX XXI xu xxm XXIV XXV XXVI XXV11 xxvm zR Y ) y xxxiii XXXIV XXXV XXXVI XXXVH wherein any substitutable carbon or nitrogen atom is optionally substituted and wherein y is 0-5, Z is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R γ is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 9. The compound of claim 1, wherein R 1 is NR 3 R 4 and R 3 and R 4 , taken together with the nitrogen atom, form a group selected from: xxxviii xxxix xl xli 10. The compound of claim 8, wherein one of R is selected from one of the following groups: i xxvii xxxiv xxxvi xxxvii 11. The compound of claim 8, wherein y is 0-3 and thus R 3 is substituted with 0-3 occunences of ZR Y . 12. The compound of claim 8, wherein y is 1 or 2. 13. The compound of claim 8, wherein y is 0 and R 3 is unsubstituted. 14. The compound of claim 8, wherein each occunence of ZR is independently halogen, CN, NO 2 , or an optionally substituted group selected from Cι- 4 alkyl, aryl, aralkyl, -N(R') 2 , CH 2 N(R') 2 , -OR', CH 2 OR', -SR', CH 2 SR', COOR', or -S(O) 2 N(R') 2 . r 15. The compound of claim 8, wherein each occunence of ZR is independently CI, Br, F, CN, CF 3 , COOH, -N(CH 3 ) 2 , -OH, CH 2 OH, or an optionally substituted group selected from Cι- 4 alkoxy, Cι- 4 alkyl, phenyl, phenyloxy, benzyl, or benzyloxy. 16. The compound of claim 1, wherein R 4 is hydrogen or optionally substituted Ci- 4 alkyl, and R 3 is (U) m R\\ wherein m is 1, and U is an optionally substituted Ci- 6 alkylidene chain, wherein up to two methylene units of the chain are optionally and independently replaced by -C(O)-, -C(O)C(O)-, -CONR-, -CONRNR-, -CO 2 -, -OC(O)-, -NRCO 2 -, -O-, - NRCONR-, -OC(O)NR'-, -NRNR, -NRCO-, -S-, -SO-, -SO 2 -, -NR-, -SO 2 NR-, or - NRSO2-. 17. The compound of claim 16, wherein U is an optionally substituted Cι- 4 alkylidene chain, wherein one methylene unit of the chain is optionally replaced by -C(O)-, -CONR-, -CO 2 -, -OC(O)-, O, or -NRCO-. 18. The compound of claim 16, wherein U is -CH 2 (C=O)NH-, -CH 2 (C=O)O-, - (CH 2 ) O-, or -CH=NO-, wherein each occunence of R' is independently hydrogen or Ci- 4 alkyl. 19. The compound of claim 1, wherein R 2 is wherein n is 0 or 1, T is NR, and Ar 1 is an optionally substituted cyclic group selected from: a g k m n o aa bb QR X ) X cc dd ee ff : 4 gg hh 11 JJ kk wherein any substitutable carbon or nitrogen atom is optionally substituted and wherein x is 0-5, Q is a bond or is a -C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R x is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R\\ C(O)R\\ CO 2 R\\ OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 20. The compound of claim 19, wherein x is 0-3 and R 2 is substituted with 0-3 occunences of QR X . 21. The compound of claim 19, wherein x is 1 or 2. 22. The compound of claim 19, wherein x is 0 and R 2 is unsubstituted. V' 23. The compound of claim 19, wherein each occunence of QR is independently halogen, CN, NO 2 , or an optionally substituted group selected from Cι- 4 alkyl, aryl, aralkyl, -N(R') 2 , CH 2 N(R') 2 , -OR', CH 2 OR', -SR', CH 2 SR', COOR', or -S(O) 2 N(R') 2 . 24. The compound of claim 19, wherein each occunence of QR is independently CI, Br, F, CN, CF 3 , COOH, -N(CH 3 ) 2 , -OH, CH 2 OH, or an optionally substituted group selected from Cι- 4 alkoxy, Cι- 4 alkyl, phenyl, phenyloxy, benzyl, or benzyloxy. 25. The compound of claim 1, wherein R 4 is hydrogen or Cι- 4 alkyl; R 3 is optionally 9 1 substituted phenyl; and R is -NRAr , and compounds have one of the following formulas: II-A-i III-A-i IV-A-i II-A-xxvii III-A-xxvii IV-A-xxvii II-A-xxxvi III-A-xxxvi IV-A-xxxvi II-A-xxvii III-A-xxvii IV-A-xxvii wherein y is 0-5, Z is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R γ is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 26. The compound of claim 1, wherein R 2 is -Ar 1 , and compounds have one of the following formulas: II-B-i III-B-i IV-B-i II-B-xxvii III-B-xxvii IV-B-xxvii II-B-xxxvi III-B-xxxvi IV-B-xxxvi II-B-xxvii III-B-xxvii IV-B-xxvii wherein y is 0-5, Z is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R γ is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 27. The compound of claim 1, wherein R 2 is NRAr 1 and Ar 1 is optionally substituted phenyl, and compounds have one of the following formulas: II-A-a III-A-a IV-A-a wherein x is 0-5, Q is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R x is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 28. The compound of claim 1, wherein R 2 is -Ar 1 , wherein Ar 1 is optionally substituted phenyl, and compounds have one of the following formulas: II-B-a III-B-a IV-B-a wherein x is 0-5, Q is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R x is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 29. The compound of claim 27 or 28, wherein: a. R 4 is hydrogen or Cι- 4 alkyl; b. when n is 1, and T is NR, R is hydrogen or Cι_ 4 alkyl; c. R 3 is a group selected from: i xxvn xxxiv xxxvi xxxvii wherein y is 0-3, Z is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R γ is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'; and d. x is 0-3, Q is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R x is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 30. The compound of claim 29, wherein y is 0-3 and R 3 is substituted with 0-3 occunences of ZR Y , and x is 0-3 and R 2 is substituted with 0-3 occunences of QR x . 31. The compound of claim 29, wherein y is 0, 1, or 2; and x is 0, 1, or 2. 32. The compound of claim 29, wherein y is 0; and x is 0, 1, or 2. 33. The compound of claim 29, wherein x is 0; and y is 0, 1, or 2. 34. The compound of claim 29, wherein each occunence of ZR Y is independently halogen, CN, NO 2 , or an optionally substituted group selected from Cι- 4 alkyl, aryl, aralkyl, -N(R') 2 , CH 2 N(R') 2 , -OR', CH 2 OR', -SR', CH 2 SR', COOR', or -S(O) 2 N(R') 2 ; and each occunence of QR X is independently halogen, CN, NO 2 , or an optionally substituted group selected from Cι- 4 alkyl, aryl, aralkyl, -N(R') 2 , CH 2 N(R') 2 , -OR', CH 2 OR', -SR', CH 2 SR', COOR', or -S(O) 2 N(R') 2 . 35. The compound of claim 29, wherein each occunence of ZR Y is independently CI, Br, F, CN, CF 3 , COOH, -N(CH 3 ) 2 , -OH, CH 2 OH, or an optionally substituted group selected from Cι- 4 alkoxy, Cι- 4 alkyl, phenyl, phenyloxy, benzyl, or benzyloxy; and each occunence of QR X is independently CI, Br, F, CN, CF 3 , COOH, -N(CH 3 ) 2 , -OH, CH 2 OH, or an optionally substituted group selected from Cι- alkoxy, Cι- 4 alkyl, phenyl, phenyloxy, benzyl, or benzyloxy. 36. The compound of claim 1, wherein R 3 is an optionally substituted group selected from phenyl, cyclohexyl, cyclobutyl or cyclopropyl, and R 2 is NRAr 1 , wherein R is hydrogen or Cι- 4 alkyl, and Ar 1 is optionally substituted phenyl, and compounds have one of the following formulas: -A-i-a III-A-i-a IV-A-i-a II-A-xxvii-a III-A-xxvii-a IV-A-xxvii-a R*)* -A-xxxvi-a III-A-xxxvi-a IV-A-xxxvi-a II-A-xxvii-a III-A-xxvii-a IV-A-xxvii-a wherein x is 0-5, Q is a bond or is a Cχ-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R x is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R' ; and wherein y is 0-5, Z is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R γ is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 37. The compound of claim 1, wherein R 3 is an optionally substituted group selected from phenyl, cyclohexyl, cyclobutyl or cyclopropyl, and R 2 is Ar 1 , wherein Ar 1 is optionally substituted phenyl, and compounds have one of the following formulas: II-B-i-a III-B-i-a IV-B-i-a II-B-xxvii-a III-B-xxvii-a IV-B-xxvii-a II-B-xxxvi-a III-B-xxxvi-a IV-B-xxxvi-a II-B-xxvii-a III-B-xxvii-a IV-B-xxvii-a wherein x is 0-5, Q is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R x is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R' ; and wherein y is 0-5, Z is a bond or is a Cι-C 6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO 2 , COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO 2 , NRCONR, SO, SO 2 , NRSO 2 , SO 2 NR, NRSO 2 NR, O, S, or NR; and each occunence of R γ is independently selected from R', halogen, NO 2 , CN, OR', SR', N(R') 2 , NR'C(O)R', NR'C(O)N(R') 2 , NR'CO 2 R', C(O)R', CO 2 R', OC(O)R', C(O)N(R') 2 , OC(O)N(R') 2 , SOR', SO 2 R', SO 2 N(R') 2 , NR'SO 2 R', NR'SO 2 N(R') 2 , C(O)C(O)R', or C(O)CH 2 C(O)R'. 38. The compound of claim 36 or 37, wherein y is 0-3 and R 3 is substituted with 0-3 occunences of ZR Y , and x is 0-3 and R 2 is substituted with 0-3 occunences of QR X . 39. The compound of claim 36 or 37, wherein y is 0, 1, or 2; and x is 0, 1, or 2. 40. The compound of claim 36 or 37, wherein y is 0; and x is 0, 1, or 2. 41. The compound of claim 36 or 37, wherein x is 0; and y is 0, 1, or 2. 42. The compound of claim 36 or 37, wherein each occunence of ZR is independently halogen, CN, NO 2 , or an optionally substituted group selected from Ci- 4 alkyl, aryl, aralkyl, -N(R') 2 , CH 2 N(R') 2 , -OR', CH 2 OR', -SR', CH 2 SR', COOR', or - S(O) 2 N(R') 2 ; and each occunence of QR X is independently halogen, CN, NO 2 , or an optionally substituted group selected from Cι- 4 alkyl, aryl, aralkyl, -N(R') 2 , CH 2 N(R') 2 , - OR', CH 2 OR', -SR', CH 2 SR', COOR', or -S(O) 2 N(R') 2 . 43. The compound of claim 36 or 37, wherein each occunence of ZR is independently CI, Br, F, CN, CF 3 , COOH, -N(CH 3 ) 2 , -OH, CH 2 OH, or an optionally substituted group selected from Cι- 4 alkoxy, Cι- 4 alkyl, phenyl, phenyloxy, benzyl, or benzyloxy; and each occunence of QR X is independently CI, Br, F, CN, CF 3 , COOH, - N(CH 3 ) 2 , -OH, CH 2 OH, or an optionally substituted group selected from Cι- 4 alkoxy, Ci- 4 alkyl, phenyl, phenyloxy, benzyl, or benzyloxy. The compound of claim 1, having one of the structures: I-l 1-2 1-3 1-4 1-5 1-6 1-7 1-8 1-9 1-10 1-11 1-12 1-13 1-14 1-15 » A A . 3 ArA 0 H O H O H 50 % inhibition versus standard wells containing DMSO, but no compound, were titrated and IC50's determined using a similar protocol. [00164] Compounds of the invention were shown to inhibit PEVI-l using the assay methods described above. In certain embodiments, the following compounds were shown to have ICso or K values less than 1.0 μM for PIM-1: 1-5, 1-18, 1-20, 1-21, 1-24, 1-25, 1-26, and 1-28. [00165] Example 3: Inhibition of GSK-3: [00166] Compounds were screened for their ability to inhibit GSK-3β (AA 1-420) activity using a standard coupled enzyme system (Fox et al. (1998) Protein Sci. 1, 2249). Reactions were carried out in a solution containing 100 mM HEPES (pH 7.5), 10 mM MgCl 2 , 25 mM NaCl, 300 μM NADH, 1 mM DTT and 1.5% DMSO. Final substrate concentrations in the assay were 20 μM ATP (Sigma Chemicals, St Louis, MO) and 300 μM peptide (American Peptide, Sunnyvale, CA). Reactions were carried out at 30 °C and 20 nM GSK-3β. Final concentrations of the components of the coupled enzyme system were 2.5 mM phosphoenolpyruvate, 300 μM NADH, 30 μg/ml pyruvate kinase and 10 μg/ml lactate dehydrogenase. [00167] An assay stock buffer solution was prepared containing all of the reagents listed above with the exception of ATP and the test compound of interest. The assay stock buffer solution (175 μl) was incubated in a 96 well plate with 5 μl of the test compound of interest at final concentrations spanning 0.002 μM to 30 μM at 30°C for 10 min. Typically, a 12 point titration was conducted by preparing serial dilutions (from 10 mM compound stocks) with DMSO of the test compounds in daughter plates. The reaction was initiated by the addition of 20 μl of ATP (final concentration 20 μM). Rates of reaction were obtained using a Molecular Devices Spectramax plate reader (Sunnyvale, CA) over 10 min at 30°C. The Kj values were determined from the rate data as a function of inhibitor concentration. [00168] Compounds of the invention were shown to inhibit GSK-3 using the assay methods described above. In certain embodiments, the following compounds were shown to have Ki values less than 2.0 μM for GSK-3: 1-18, 1-21, 1-37, 1-38, 1-39, 1-40, 1-62, 1-66, 1- 85, and 1-86. [00169] Example 4: Inhibition of CDK-2: [00170] Compounds were screened for their ability to inhibit CDK-2/Cyclin A using a standard coupled enzyme assay (Fox et al (1998) Protein Sci 1, 2249). Reactions were carried out in 100 mM HEPES pH 7.5, 10 mM MgCl 2 , 25 mM NaCl, 1 mM DTT and 1.5% DMSO. Final substrate concentrations in the assay were 100 μM ATP (Sigma chemicals) and 100 μM peptide (American Peptide, Sunnyvale, CA). Assays were carried out at 30°C and 25 nM CDK-2/Cyclin A. Final concentrations of the components of the coupled enzyme system were 2.5 mM phosphoenolpyruvate, 350 μM NADH, 30 μg/ml pyruvate kinase and 10 μg/ml lactate dehydrogenase. [00171] An assay stock buffer solution was prepared containing all of the reagents listed above, with the exception of CDK-2/Cyclin A, DTT and the test compound of interest. 56 μl of the test reaction was placed in a 384 well plate followed by addition of 1 μl of 2 mM DMSO stock containing the test compound (final compound concentration 30 μM). The plate was preincubated for -10 minutes at 30 °C and the reaction initiated by addition of 10 μl of enzyme (final concentration 25 nM). Rates of reaction were obtained using a BioRad Ultramark plate reader (Hercules, CA) over a 5 minute read time at 30°C. K; values were determined according to standard methods. [00172] Compounds of the invention were shown to inhibit CDK-2 using the assay methods described above. In certain embodiments, the following compounds were shown to have Ki values less than 2.0 μM for CDK-2: 1-68 and 1-73. [00173] Example 5: Inhibition of SRC: [00174] The compounds are evaluated as inhibitors of human Src kinase using either a radioactivity-based assay or spectrophotometric assay. [00175] Src Inhibition Assay A: Radioactivity-based Assay [00176] The compounds are assayed as inhibitors of full length recombinant human Src kinase (from Upstate Biotechnology, cat. no. 14-117) expressed and purified from baculo viral cells. Src kinase activity is monitored by following the incorporation of 33 P from ATP into the tyrosine of a random poly Glu-Tyr polymer substrate of composition, Glu:Tyr = 4:1 (Sigma, cat. no. P-0275). The following are the final concentrations of the assay components: 0.05 M HEPES, pH 7.6, 10 mM MgCl 2 , 2 mM DTT, 0.25 mg/ml BSA, 10 μM ATP (1-2 μCi 33 P-ATP per reaction), 5 mg/ml poly Glu-Tyr, and 1-2 units of recombinant human Src kinase. In a typical assay, all the reaction components with the exception of ATP are pre-mixed and aliquoted into assay plate wells. Inhibitors dissolved in DMSO are added to the wells to give a final DMSO concentration of 2.5%. The assay plate is incubated at 30 °C for 10 min before initiating the reaction with 33 P-ATP. After 20 min of reaction, the reactions are quenched with 150 μl of 10% trichloroacetic acid (TCA) containing 20 mM Na 3 PO 4 . The quenched samples are then transfened to a 96-well filter plate (Whatman, TJNI- Filter GF/F Glass Fiber Filter, cat no. 7700-3310) installed on a filter plate vacuum manifold. Filter plates are washed four times with 10% TCA containing 20 mM Na 3 PO 4 and then 4 times with methanol. 200μl of scintillation fluid is then added to each well. The plates were sealed and the amount of radioactivity associated with the filters is quantified on a TopCount scintillation counter. The radioactivity incorporated is plotted as a function of the inhibitor concentration. The data is fitted to a competitive inhibition kinetics model to get the Ki for the compound. [00177] Src Inhibition Assay B: Spectrophotometric Assay [00178] The ADP produced from ATP by the human recombinant Src kinase-catalyzed phosphorylation of poly Glu-Tyr substrate is quantified using a coupled enzyme assay (Fox et al (1998) Protein Sci 1, 2249). In this assay one molecule of NADH is oxidised to NAD for every molecule of ADP produced in the kinase reaction. The disappearance of NADH is conveniently followed at 340 nm. [00179] The following are the final concentrations of the assay components: 0.025 M HEPES, pH 7.6, 10 mM MgCl 2 , 2 mM DTT, 0.25 mg/ml poly Glu-Tyr, and 25 nM of recombinant human Src kinase. Final concentrations of the components of the coupled enzyme system are 2.5 mM phosphoenolpyruvate, 200 μM NADH, 30 μg/ml pyruvate kinase and 10 μg/ml lactate dehydrogenase. [00180] In a typical assay, all the reaction components with the exception of ATP are pre- mixed and aliquoted into assay plate wells. Inhibitors dissolved in DMSO are added to the wells to give a final DMSO concentration of 2.5%. The assay plate is incubated at 30°C for 10 min before initiating the reaction with 100 μM ATP. The absorbance change at 340 nm with time, the rate of the reaction, is monitored on a molecular devices plate reader. The data of rate as a function of the inhibitor concentration is fitted to competitive inhibition kinetics model to get the Ki for the compound. [00181] Compounds of the invention were shown to inhibit SRC using the assay methods described above. In certain embodiments, the following compounds were shown to have Ki values less than 5.0 μM for SRC: 1-25, 1-26, 1-28, and 1-29.","lang":"en","source":"WIPO_FULLTEXT","data_format":"ORIGINAL"}},"description_lang":["en"],"has_description":true,"has_docdb":true,"has_inpadoc":true,"has_full_text":true,"biblio_lang":"en"},"jurisdiction":"WO","collections":[],"usersTags":[],"lensId":"166-014-743-110-129","publicationKey":"WO_2004_058769_A2","displayKey":"WO 2004/058769 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(P.C.T.)","inventorModel":{"inventors":[{"name":{"value":"GREEN JEREMY","valueNormalised":"Green Jeremy"},"inventorship":null},{"name":{"value":"GREY RONALD JR","valueNormalised":"Grey Ronald Jr"},"inventorship":null},{"name":{"value":"PIERCE ALBERT C","valueNormalised":"Pierce Albert C"},"inventorship":null}],"inventorships":[],"unmatchedInventorships":[],"activeUserHasInventorship":false},"simpleFamilyId":188643861,"citesPatentCount":1,"countrySpec":{"countryName":"WIPO (P.C.T.)","description":"INTERNATIONAL APPLICATION PUBLISHED WITHOUT INTERNATIONAL Search Report","rule":"","docType":"PATENT_APPLICATION"},"pageTitle":"WO 2004/058769 A2 - Compositions Useful As Inhibitors Of Protein Kinases","documentTitle":"Compositions Useful As Inhibitors Of Protein Kinases"},"claims":{"source":"xml_claims","claims":[{"lines":["CLAIMS"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["A compound of formula (I):"],"number":1,"annotation":false,"title":false,"claim":true},{"lines":["(I) or a pharmaceutically acceptable salt thereof, wherein R1 is OR3, SR3, or NR3R4; wherein each occunence of R3 and R4 is independently (U)mR\\ wherein U is an optionally substituted Cι-6alkylidene chain, wherein up to two methylene units of the chain are optionally and independently replaced by -C(O)-, -C(O)C(O)-, -CONR-, -CONRNR-, -CO2-, -OC(O)-, -NRCO2-, -O-, - NRCONR-, -OC(O)NR-, -NRNR, -NRCO-, -S-, -SO-, -SO2-, -NR-, -SO2NR-, or- NRSO2-; m is 0 or 1; or wherein R3 and R4, taken together with the nitrogen form an optionally substituted 5-8 membered heterocyclyl or heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur; each occunence of R is independently selected from hydrogen or an optionally substituted Cι-6 aliphatic group, and each occunence of R' is independently selected from hydrogen or an optionally substituted group selected from Cι-8 aliphatic, C6-ιo aryl, a heteroaryl ring having 5-10 ring atoms, or a heterocyclyl ring having 3-10 ring atoms, or wherein R and R' taken together, or two occunences of R' on the same substituent or different substituents, taken together, form a 5-8 membered heterocyclyl or heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["R2 is -(T)nAr1, wherein T is NR; n is 0 or 1; Ar1 is a 3-7 membered saturated, partially unsaturated, or fully unsaturated monocyclic ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-10 membered saturated, partially unsaturated, or fully unsaturated bicyclic ring system having 0-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur; provided that:"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["9 1"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["1) when R is optionally substituted 1,3, 5-triazine, then R is not N-morpholino;"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["2) when R2 is nitro substituted pyrazolyl, furyl, or thiophene, then R1 is not NR3R4;"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["3) when R2 is furyl, then R2 is not NH2; \n\n 4) when R2 is optionally substituted pyridyl or phenyl, then R1 is not OR3, where R3 is halogen substituted alkyl;"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["5) when R2 is phenyl substituted with haloalkyl or haloalkoxy, then R1 is not NH(C1-4alkyl) or O(CH2)2N(Me)2;"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["6) compounds of formula I exclude: a. Butanoic acid, 2-(benzylamino)-3[(3-phenyl-l,2,4-triazolo [4,3-b] pyridazin-6-yl) hydrazono] -methyl ester; b. Benzamide, N-[2,5-dihydro-3-methyl-5-oxo-l-(3-phenyl-l,2,4-trazolo [4,3- b] pyridazin-6-yl)-lH-pyrazol-4-yl]; and c. 2-propenoic acid, 2-(benzylamino)-3-[3,5-dimethyl-l-(3-phenyl-l,2,4- triazolo [4,3-b] pyridazin-6-yl)-lH-pyrazol-4-yl]-;"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["7) when R2 is phenyl substituted with one or more occunences of OMe, Me, NO2, CI, or CF3, then R1 is not optionally substituted morpholino or piperazinyl;"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["8) when R2 is phenyl or fluoro-substituted phenyl, R1 is not -O-CH2-(triazolyl);"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["9) when R1 is -NH(cyclopropyl), then R2 is not phenyl substituted with one occunence of CF3 in the para position;"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["10) when R2 is unsubstituted phenyl, then R1 is not -SR3, wherein R3 is phenyl substituted with CF3 in the meta position, phenyl substituted with two occunences of OCH3, (CH2)2OH, -(CH2)COOCH2CH3, or phenyl substituted with one occunence of CI in the para position; and"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["11) when R2 is unsubstituted phenyl, then R1 is not NH(CH)=NOH."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein R1 is NR3R4, OR3, or SR3, and compounds have one of the following general formulas II, III or IV:"],"number":2,"annotation":false,"title":false,"claim":true},{"lines":["II III IV"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein n is 1, T is NR, and R2 is -NRAr1, and compounds have one of the general formulas IIA, IIIA, or IVA:"],"number":3,"annotation":false,"title":false,"claim":true},{"lines":["IIA IIIA IVA"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein m is 0, and R is -Ar , and compounds have one of the general formulas IIB, IIIB, or IVB:"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IIB IIIB IVB"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein R4 is hydrogen or optionally substituted - 4alkyl and R is an optionally substituted aryl, heteroaryl, cycloaliphatic, or heterocycloaliphatic group."],"number":5,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 1, wherein R4 is hydrogen or optionally substituted Ci- alkyl and R3 is an optionally substituted 5- or 6-membered aryl or heteroaryl group."],"number":6,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 1, wherein R4 is hydrogen or optionally substituted C\\. alkyl and R3 is an optionally substituted 3-7-membered cycloaliphatic or heterocycloaliphatic group."],"number":7,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 1, wherein R4 is hydrogen or optionally substituted Ci- 4alkyl, and R3 is an optionally substituted cyclic group selected from:"],"number":8,"annotation":false,"title":false,"claim":true},{"lines":["u iii ιv"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["VI vu Vlll"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IX X XI xu"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["XVII XV111 XIX XX"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["XXI xu xxm XXIV"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["XXV XXVI XXV11 xxvm"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["zRY)y \n\n \n\n \n\n\n\n xxxiii XXXIV XXXV XXXVI XXXVH"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["wherein any substitutable carbon or nitrogen atom is optionally substituted and wherein y is 0-5, Z is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rγ is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein R1 is NR3R4 and R3 and R4, taken together with the nitrogen atom, form a group selected from:"],"number":9,"annotation":false,"title":false,"claim":true},{"lines":["xxxviii xxxix xl xli"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 8, wherein one of R is selected from one of the following groups:"],"number":10,"annotation":false,"title":false,"claim":true},{"lines":["i xxvii xxxiv xxxvi xxxvii"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 8, wherein y is 0-3 and thus R3 is substituted with 0-3 occunences of ZRY."],"number":11,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 8, wherein y is 1 or 2."],"number":12,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 8, wherein y is 0 and R3 is unsubstituted."],"number":13,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 8, wherein each occunence of ZR is independently halogen, CN, NO2, or an optionally substituted group selected from Cι-4alkyl, aryl, aralkyl, -N(R')2, CH2N(R')2, -OR', CH2OR', -SR', CH2SR', COOR', or -S(O)2N(R')2."],"number":14,"annotation":false,"title":false,"claim":true},{"lines":["r"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 8, wherein each occunence of ZR is independently CI, Br, F, CN, CF3, COOH, -N(CH3)2, -OH, CH2OH, or an optionally substituted group selected from Cι-4alkoxy, Cι-4alkyl, phenyl, phenyloxy, benzyl, or benzyloxy."],"number":15,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 1, wherein R4 is hydrogen or optionally substituted Ci- 4alkyl, and R3 is (U)mR\\ wherein m is 1, and U is an optionally substituted Ci-6alkylidene chain, wherein up to two methylene units of the chain are optionally and independently replaced by -C(O)-, -C(O)C(O)-, -CONR-, -CONRNR-, -CO2-, -OC(O)-, -NRCO2-, -O-, - NRCONR-, -OC(O)NR'-, -NRNR, -NRCO-, -S-, -SO-, -SO2-, -NR-, -SO2NR-, or - NRSO2-."],"number":16,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 16, wherein U is an optionally substituted Cι-4alkylidene chain, wherein one methylene unit of the chain is optionally replaced by -C(O)-, -CONR-, -CO2-, -OC(O)-, O, or -NRCO-."],"number":17,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 16, wherein U is -CH2(C=O)NH-, -CH2(C=O)O-, - (CH2) O-, or -CH=NO-, wherein each occunence of R' is independently hydrogen or Ci- 4alkyl."],"number":18,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 1, wherein R2 is \n\n wherein n is 0 or 1, T is NR, and Ar1 is an optionally substituted cyclic group selected from:"],"number":19,"annotation":false,"title":false,"claim":true},{"lines":["a \n\n \n\n g"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["k"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["m n o"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["aa bb"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["QRX)X \n\n cc dd ee ff \n\n : 4 \n\n gg hh 11 JJ kk"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["wherein any substitutable carbon or nitrogen atom is optionally substituted and wherein x is 0-5, Q is a bond or is a -C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rx is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R\\ C(O)R\\ CO2R\\ OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 19, wherein x is 0-3 and R2 is substituted with 0-3 occunences of QRX."],"number":20,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 19, wherein x is 1 or 2."],"number":21,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 19, wherein x is 0 and R2 is unsubstituted."],"number":22,"annotation":false,"title":false,"claim":true},{"lines":["V'"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 19, wherein each occunence of QR is independently halogen, CN, NO2, or an optionally substituted group selected from Cι-4alkyl, aryl, aralkyl, -N(R')2, CH2N(R')2, -OR', CH2OR', -SR', CH2SR', COOR', or -S(O)2N(R')2."],"number":23,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 19, wherein each occunence of QR is independently CI, Br, F, CN, CF3, COOH, -N(CH3)2, -OH, CH2OH, or an optionally substituted group selected from Cι-4alkoxy, Cι-4alkyl, phenyl, phenyloxy, benzyl, or benzyloxy."],"number":24,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 1, wherein R4 is hydrogen or Cι-4alkyl; R3 is optionally"],"number":25,"annotation":false,"title":false,"claim":true},{"lines":["9 1 substituted phenyl; and R is -NRAr , and compounds have one of the following formulas:"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["II-A-i III-A-i"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IV-A-i II-A-xxvii"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["III-A-xxvii IV-A-xxvii"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["II-A-xxxvi III-A-xxxvi"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IV-A-xxxvi II-A-xxvii"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["III-A-xxvii IV-A-xxvii wherein y is 0-5, Z is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, \n\nOCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rγ is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein R2 is -Ar1, and compounds have one of the following formulas:"],"number":26,"annotation":false,"title":false,"claim":true},{"lines":["II-B-i III-B-i"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IV-B-i II-B-xxvii"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["III-B-xxvii IV-B-xxvii"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["II-B-xxxvi III-B-xxxvi"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IV-B-xxxvi II-B-xxvii"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["III-B-xxvii IV-B-xxvii"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["wherein y is 0-5, Z is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rγ is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein R2 is NRAr1 and Ar1 is optionally substituted phenyl, and compounds have one of the following formulas:"],"number":27,"annotation":false,"title":false,"claim":true},{"lines":["II-A-a III-A-a IV-A-a wherein x is 0-5, Q is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rx is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein R2 is -Ar1, wherein Ar1 is optionally substituted phenyl, and compounds have one of the following formulas:"],"number":28,"annotation":false,"title":false,"claim":true},{"lines":["II-B-a III-B-a IV-B-a wherein x is 0-5, Q is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rx is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 27 or 28, wherein: a. R4 is hydrogen or Cι-4alkyl; b. when n is 1, and T is NR, R is hydrogen or Cι_4alkyl; c. R3 is a group selected from:"],"number":29,"annotation":false,"title":false,"claim":true},{"lines":["i xxvn xxxiv xxxvi xxxvii wherein y is 0-3, Z is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rγ is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'; and d. x is 0-3, Q is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rx is independently selected from R', \n\nhalogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 29, wherein y is 0-3 and R3 is substituted with 0-3 occunences of ZRY, and x is 0-3 and R2 is substituted with 0-3 occunences of QRx."],"number":30,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 29, wherein y is 0, 1, or 2; and x is 0, 1, or 2."],"number":31,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 29, wherein y is 0; and x is 0, 1, or 2."],"number":32,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 29, wherein x is 0; and y is 0, 1, or 2."],"number":33,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 29, wherein each occunence of ZRY is independently halogen, CN, NO2, or an optionally substituted group selected from Cι-4alkyl, aryl, aralkyl, -N(R')2, CH2N(R')2, -OR', CH2OR', -SR', CH2SR', COOR', or -S(O)2N(R')2; and each occunence of QRX is independently halogen, CN, NO2, or an optionally substituted group selected from Cι-4alkyl, aryl, aralkyl, -N(R')2, CH2N(R')2, -OR', CH2OR', -SR', CH2SR', COOR', or -S(O)2N(R')2."],"number":34,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 29, wherein each occunence of ZRY is independently CI, Br, F, CN, CF3, COOH, -N(CH3)2, -OH, CH2OH, or an optionally substituted group selected from Cι-4alkoxy, Cι-4alkyl, phenyl, phenyloxy, benzyl, or benzyloxy; and each occunence of QRX is independently CI, Br, F, CN, CF3, COOH, -N(CH3)2, -OH, CH2OH, or an optionally substituted group selected from Cι- alkoxy, Cι-4alkyl, phenyl, phenyloxy, benzyl, or benzyloxy."],"number":35,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 1, wherein R3 is an optionally substituted group selected from phenyl, cyclohexyl, cyclobutyl or cyclopropyl, and R2 is NRAr1, wherein R is hydrogen or Cι-4alkyl, and Ar1 is optionally substituted phenyl, and compounds have one of the following formulas: \n\n\n\n -A-i-a III-A-i-a"],"number":36,"annotation":false,"title":false,"claim":true},{"lines":["IV-A-i-a II-A-xxvii-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["III-A-xxvii-a IV-A-xxvii-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["R*)* -A-xxxvi-a III-A-xxxvi-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IV-A-xxxvi-a II-A-xxvii-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["III-A-xxvii-a IV-A-xxvii-a wherein x is 0-5, Q is a bond or is a Cχ-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rx is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R' ; and wherein y is 0-5, Z is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rγ is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 1, wherein R3 is an optionally substituted group selected from phenyl, cyclohexyl, cyclobutyl or cyclopropyl, and R2 is Ar1, wherein Ar1 is optionally substituted phenyl, and compounds have one of the following formulas:"],"number":37,"annotation":false,"title":false,"claim":true},{"lines":["II-B-i-a III-B-i-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IV-B-i-a II-B-xxvii-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["III-B-xxvii-a IV-B-xxvii-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["II-B-xxxvi-a III-B-xxxvi-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["IV-B-xxxvi-a II-B-xxvii-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["III-B-xxvii-a IV-B-xxvii-a"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["wherein x is 0-5, Q is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rx is independently selected from R', \n\nhalogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R' ; and wherein y is 0-5, Z is a bond or is a Cι-C6 alkylidene chain wherein up to two non- adjacent methylene units of Q are optionally replaced by CO, CO2, COCO, CONR, OCONR, NRNR, NRNRCO, NRCO, NRCO2, NRCONR, SO, SO2, NRSO2, SO2NR, NRSO2NR, O, S, or NR; and each occunence of Rγ is independently selected from R', halogen, NO2, CN, OR', SR', N(R')2, NR'C(O)R', NR'C(O)N(R')2, NR'CO2R', C(O)R', CO2R', OC(O)R', C(O)N(R')2, OC(O)N(R')2, SOR', SO2R', SO2N(R')2, NR'SO2R', NR'SO2N(R')2, C(O)C(O)R', or C(O)CH2C(O)R'."],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["The compound of claim 36 or 37, wherein y is 0-3 and R3 is substituted with 0-3 occunences of ZRY, and x is 0-3 and R2 is substituted with 0-3 occunences of QRX."],"number":38,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 36 or 37, wherein y is 0, 1, or 2; and x is 0, 1, or 2."],"number":39,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 36 or 37, wherein y is 0; and x is 0, 1, or 2."],"number":40,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 36 or 37, wherein x is 0; and y is 0, 1, or 2."],"number":41,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 36 or 37, wherein each occunence of ZR is independently halogen, CN, NO2, or an optionally substituted group selected from Ci- 4alkyl, aryl, aralkyl, -N(R')2, CH2N(R')2, -OR', CH2OR', -SR', CH2SR', COOR', or - S(O)2N(R')2; and each occunence of QRX is independently halogen, CN, NO2, or an optionally substituted group selected from Cι-4alkyl, aryl, aralkyl, -N(R')2, CH2N(R')2, - OR', CH2OR', -SR', CH2SR', COOR', or -S(O)2N(R')2."],"number":42,"annotation":false,"title":false,"claim":true},{"lines":["The compound of claim 36 or 37, wherein each occunence of ZR is independently CI, Br, F, CN, CF3, COOH, -N(CH3)2, -OH, CH2OH, or an optionally substituted group selected from Cι-4alkoxy, Cι-4alkyl, phenyl, phenyloxy, benzyl, or benzyloxy; and each occunence of QRX is independently CI, Br, F, CN, CF3, COOH, - N(CH3)2, -OH, CH2OH, or an optionally substituted group selected from Cι-4alkoxy, Ci- 4alkyl, phenyl, phenyloxy, benzyl, or benzyloxy. \n\n The compound of claim 1, having one of the structures:"],"number":43,"annotation":false,"title":false,"claim":true},{"lines":["I-l 1-2 1-3"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["1-4 1-5 1-6"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["1-7 1-8 1-9"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["1-10 1-11 1-12"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["1-13 1-14 1-15"],"number":-1,"annotation":true,"title":false,"claim":false},{"lines":["» A A .3 ArA 0 H O H O H