{"search_session":{},"preferences":{"l":"en","queryLanguage":"en"},"patentId":"US_7507739_B2","frontPageModel":{"patentViewModel":{"ref":{"entityRefType":"PATENT","entityRefId":"199-737-147-574-118"},"entityMetadata":{"linkedIds":{"empty":true},"tags":[],"collections":[{"id":11844,"type":"PATENT","title":"University of Kansas Patent Portfolio","description":"","access":"OPEN_ACCESS","displayAvatar":true,"attested":false,"itemCount":8584,"tags":[],"user":{"id":91044780,"username":"Cambialens","firstName":"","lastName":"","created":"2015-05-04T00:55:26.000Z","displayName":"Cambialens","preferences":"{\"usage\":\"public\",\"beta\":false}","accountType":"PERSONAL","isOauthOnly":false},"notes":[{"id":8456,"type":"COLLECTION","user":{"id":91044780,"username":"Cambialens","firstName":"","lastName":"","created":"2015-05-04T00:55:26.000Z","displayName":"Cambialens","preferences":"{\"usage\":\"public\",\"beta\":false}","accountType":"PERSONAL","isOauthOnly":false},"text":"
Search Applicants and Owners separately: univ* AND Kansas. Select more for logical variants. Add to collection. Select all patents in the collection and expand by simple families. Add to collection. Total patents: 1781
Search Applicants and Owners separately: univ* AND Kansas. Select more for logical variants. Add to collection. Select all patents in the collection and expand by simple families. Add to collection. Total patents: 1781
R1 is selected from\n\n
and C6-C8 cycloalkyl optionally substituted with R8;\n
R2 is a moiety of the group\n\n
n is an integer of 2, 3, or 4;\n
X is Cl or Br;\n
Y is S, CH2 or NR4;\n
Q is selected from —NR6R7 and —OH;\n
L1 and L2 are each independently H, F, Cl, Br, or CF3;\n
R3 is CF3 or C2F5;\n
R4 and R5 are each independently H or C1-C3 alkyl;\n
R6 and R7 are each independently H or C1-C3 alkyl; or\n
R6 and R7 when optionally taken together with the nitrogen atom to which each is attached form a 4 to 6 membered saturated heterocyclic ring with 1-2 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms, and optionally substituted with R8;\n
R8 is C1-C3 alkyl;\n
or pharmaceutically acceptable salts thereof."],"number":1,"annotation":false,"title":false,"claim":true},{"lines":["A compound according to claim 1, represented by formula (Ia)\nor pharmaceutically acceptable salts thereof."],"number":2,"annotation":false,"title":false,"claim":true},{"lines":["A compound according to claim 1, represented by formula (Ib)\nor pharmaceutically acceptable salts thereof."],"number":3,"annotation":false,"title":false,"claim":true},{"lines":["A compound according to claim 1 wherein R2 is\nor pharmaceutically acceptable salts thereof."],"number":4,"annotation":false,"title":false,"claim":true},{"lines":["A compound according to claim 1 wherein R1 is C6-C8 cycloalkyl optionally substituted with R8 or pharmaceutically acceptable salts thereof."],"number":5,"annotation":false,"title":false,"claim":true},{"lines":["The compound according to claim 1, 5-chloro-6-(4-{[3-(dimethylamino)propyl]thio}-2,6-difluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine or pharmaceutically acceptable salts thereof."],"number":6,"annotation":false,"title":false,"claim":true},{"lines":["The compound according to claim 1, 2-[4-(5-chloro-7-{[(1S)-2,2,2-trifluoro-1-methylethyl]amino}[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]ethanol or pharmaceutically acceptable salts thereof."],"number":7,"annotation":false,"title":false,"claim":true},{"lines":["The compound according to claim 1, 3-[4-(5-chloro-7-{[(1S)-2,2,2-trifluoro-1-methylethyl]amino}[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]propan-1-ol or pharmaceutically acceptable salts thereof."],"number":8,"annotation":false,"title":false,"claim":true},{"lines":["The compound according to claim 1, N1-[4-(5-chloro-7-{[(1S)-2,2,2-trifluoro-1-methylethyl]amino}[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenyl]-N1, N3, N3-trimethylpropane-1,3-diamine or pharmaceutically acceptable salts thereof."],"number":9,"annotation":false,"title":false,"claim":true},{"lines":["The compound according to claim 1, N1-[4-(5-chloro-7-{[(1S)-2,2,2-trifluoro-1-methylethyl]amino}[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenyl]-N3, N3-dimethylpropane-1,3-diamine or pharmaceutically acceptable salts thereof."],"number":10,"annotation":false,"title":false,"claim":true},{"lines":["The compound according to claim 1, N1-[4-(5-chloro-7-{[(1S)-2,2,2-trifluoro-1-methylethyl]amino}[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenyl]-N2, N2-dimethylethane-1,2-diamine or pharmaceutically acceptable salts thereof."],"number":11,"annotation":false,"title":false,"claim":true},{"lines":["The compound according to claim 1, 5-chloro-6-{4-[4-(dimethylamino)butyl]-2,6-difluorophenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine or pharmaceutically acceptable salts thereof."],"number":12,"annotation":false,"title":false,"claim":true},{"lines":["A compound according to claim 1 or pharmaceutically acceptable salts thereof selected from the group:\n
5-chloro-6-(4-{[3-(dimethylamino)propyl]thio}-2,6-difluorophenyl-N-[(1R)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,\n
N1-[4-(5-chloro-7-{[(1R)-2,2,2-trifluoro-1-methylethyl]amino}[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenyl]-N1, N3, N3-trimethylpropane-1,3-diamine,\n
N1-[4-(5-chloro-7-{[(1R)-2,2,2-trifluoro-1-methylethyl]amino}[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenyl]-N3,N3-dimethylpropane-1,3-diamine,\n
N1-[4-(5-chloro-7-{[(1R)-2,2,2-trifluoro-1-methylethyl]amino}[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenyl]-N2, N2-dimethylethane-1,2-diamine and\n
5-chloro-6-{4-[4-(dimethylamino)butyl]-2,6-difluorophenyl}-N-[(1R)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine."],"number":13,"annotation":false,"title":false,"claim":true},{"lines":["A pharmaceutical composition which comprises an effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier."],"number":14,"annotation":false,"title":false,"claim":true},{"lines":["A process for the preparation of a compound of Formula (I)\nwherein:\n
R1 is\n\n
R2 is a moiety\n\n
n is an integer of 2, 3, or 4;\n
X is Cl or Br;\n
Y is S, or NR4;\n
Q is selected from —NR6R7 and —OH;\n
L1 and L2 are each independently H, F, Cl, Br or CF3;\n
R3 is CF3 or C2F5;\n
R4 and R5 are each independently H or C1-C3 alkyl;\n
R6 and R7 are each independently H or C1-C3 alkyl; or\n
R6 and R7 when optionally taken together with the nitrogen atom to which each is attached form a 4 to 6 membered saturated heterocyclic ring with 1-2 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms, and optionally substituted with R8;\n
R8 is C1-C3 alkyl;\n
comprising the step of reacting a compound of formula (II)\n\nwhere L3 is a leaving group with a compound of the formula HY—(CH2)nQ in the presence of a strong base optionally in the presence of an aprotic solvent to give a compound of Formula (I) and pharmaceutically acceptable salts thereof."],"number":15,"annotation":false,"title":false,"claim":true},{"lines":["A process according to claim 15 wherein the leaving group L3 is F."],"number":16,"annotation":false,"title":false,"claim":true},{"lines":["A process according to claim 15 wherein the strong base is selected from an alkali metal hydroxide, alkali metal carbonate and alkali metal hydride."],"number":17,"annotation":false,"title":false,"claim":true},{"lines":["A process according to claim 15 wherein the aprotic solvent is selected from dimethylsulfoxide and dimethylformamide."],"number":18,"annotation":false,"title":false,"claim":true},{"lines":["A process according to claim 15 wherein formula (II) is represented by the formula"],"number":19,"annotation":false,"title":false,"claim":true},{"lines":["A process for the preparation of a compound of Formula (I)\nwherein:\n
R1 is\n\n
R2 is a moiety of the group\n\n
n is an integer of 2, 3, or 4;\n
X is Cl or Br;\n
Y is CH2;\n
Q is —NR6R7;\n
L1 and L2 are each independently H, F, Cl, Br or CF3;\n
R3 is CF3 or C2F5;\n
R5 is H or C1-C3 alkyl;\n
R6 and R7 are each independently H or C1-C3 alkyl; or\n
R6 and R7 when optionally taken together with the nitrogen atom to which each is attached form a 4 to 6 membered saturated heterocyclic ring with 1-2 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms, and optionally substituted with R8;\n
R8 is C1-C3 alkyl;\nand pharmaceutically acceptable salts thereof comprising the steps of:\n
a) reacting diester (III)\n\nwith 2-amino-1,3,4-triazole in the presence of a tertiary base to afford a compound (V) of the formula\n
b) halogenating compound (V) with POX3 to afford 5,7-dihalo compound (VI)\n\n
c) reacting the 5,7-dihalo compound (VI) with amine (VII)\n\nin the presence of base in an aprotic solvent to afford compounds of Formula (I) where Y is —CH2—\nand pharmaceutically acceptable salts thereof."],"number":20,"annotation":false,"title":false,"claim":true},{"lines":["A process according to claim 20 wherein the base is N,N-diisopropylethylamine."],"number":21,"annotation":false,"title":false,"claim":true},{"lines":["A process according to claim 20 wherein the aprotic solvent is selected from dimethylsulfoxide and dimethylformamide."],"number":22,"annotation":false,"title":false,"claim":true},{"lines":["A process according to claim 20 wherein the amine (VII)\nhas the (S) configuration."],"number":23,"annotation":false,"title":false,"claim":true},{"lines":["A compound of Formula (I)\nwherein:\n
R1 is\n\n
R2 is a moiety\n\n
n is an integer of 2, 3, or 4;\n
X is Cl or Br;\n
Y is S, or NR4;\n
Q is selected from —NR6R7 and —OH;\n
L1 and L2 are each independently H, F, Cl, Br or CF3;\n
R3 is CF3 or C2F5;\n
R4 and R5 are each independently H or C1-C3 alkyl;\n
R6 and R7 are each independently H or C1-C3 alkyl; or\n
R6 and R7 when optionally taken together with the nitrogen atom to which each is attached form a 4 to 6 membered saturated heterocyclic ring with 1-2 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms, and optionally substituted with R8;\n
R8 is C1-C3 alkyl;\n
and pharmaceutically acceptable salts thereof\nproduced by the process which comprises the step of reacting a compound of Formula (II)\nwhere L3 is a leaving group with a compound of the formula HY—(CH2)nQ in the presence of a strong base optionally in the presence of an aprotic solvent to give a compound of Formula (I) and pharmaceutically acceptable salts thereof."],"number":24,"annotation":false,"title":false,"claim":true},{"lines":["A compound produced by the process according to claim 24 wherein the leaving group L3 is F."],"number":25,"annotation":false,"title":false,"claim":true},{"lines":["A compound produced by the process according to claim 24 wherein the strong base is selected from an alkali metal hydroxide, alkali metal carbonate and alkali metal hydride."],"number":26,"annotation":false,"title":false,"claim":true},{"lines":["A compound produced by the process according to claim 24 wherein the aprotic solvent is selected from dimethylsulfoxide and dimethylformamide."],"number":27,"annotation":false,"title":false,"claim":true},{"lines":["A compound produced by the process according to claim 24 wherein Formula (II) is represented by the formula"],"number":28,"annotation":false,"title":false,"claim":true},{"lines":["A compound of Formula (I)\nwherein:\n
R1 is\n\n\n
R2 is a moiety of the group\n\n
n is an integer of 2, 3, or 4;\n
X is Cl or Br;\n
Y is CH2;\n
Q is —NR6R7;\n
L1 and L2 are each independently H, F, Cl, Br or CF3;\n
R3 is CF3 or C2F5;\n
R5 is H or C1-C3 alkyl;\n
R6 and R7 are each independently H or C1-C3 alkyl; or\n
R6 and R7 when optionally taken together with the nitrogen atom to which each is attached form a 4 to 6 membered saturated heterocyclic ring with 1-2 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms, and optionally substituted with R8;\n
R8 is C1-C3 alkyl;\n
and pharmaceutically acceptable salts thereof,\nproduced by the process which comprises the steps of:\n
a) reacting diester (III)\n\n
with 2-amino-1,3,4-triazole in the presence of a tertiary amine base to afford a compound (V) of the formula\n\n
b) halogenating compound (V) with POX3 to afford 5,7-dihalo compound (VI)\n\n
c) reacting the 5,7-dihalo compound (VI) with amine (VII)\n\nin the presence of base in an aprotic solvent to afford compounds of Formula (I) where Y is —CH2—,\nand pharmaceutically acceptable salts thereof."],"number":29,"annotation":false,"title":false,"claim":true},{"lines":["A compound produced by the process according to claim 29 wherein the base is N,N-diisopropylethylamine."],"number":30,"annotation":false,"title":false,"claim":true},{"lines":["A compound produced by the process according to claim 29 wherein the aprotic solvent is selected from dimethylsulfoxide and dimethylformamide"],"number":31,"annotation":false,"title":false,"claim":true},{"lines":["A compound produced by the process according to claim 29 wherein the amine (VII)\nhas the (S) configuration."],"number":32,"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":[]}}