JP2007538102A5 - - Google Patents
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- JP2007538102A5 JP2007538102A5 JP2007527506A JP2007527506A JP2007538102A5 JP 2007538102 A5 JP2007538102 A5 JP 2007538102A5 JP 2007527506 A JP2007527506 A JP 2007527506A JP 2007527506 A JP2007527506 A JP 2007527506A JP 2007538102 A5 JP2007538102 A5 JP 2007538102A5
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- JP
- Japan
- Prior art keywords
- alkoxy
- alkyl
- optionally substituted
- group
- optionally
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000005843 halogen group Chemical group 0.000 claims 53
- 125000001424 substituent group Chemical group 0.000 claims 48
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 43
- -1 NR 4 R 4 Chemical group 0.000 claims 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 37
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims 32
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 29
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 23
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 229920006395 saturated elastomer Polymers 0.000 claims 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 13
- 125000004414 alkyl thio group Chemical group 0.000 claims 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 206010012601 diabetes mellitus Diseases 0.000 claims 9
- 239000003112 inhibitor Substances 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000002883 imidazolyl group Chemical group 0.000 claims 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims 6
- 125000002971 oxazolyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 6
- 125000000335 thiazolyl group Chemical group 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 5
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000003613 bile acid Substances 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000008177 pharmaceutical agent Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims 2
- QRFDLOOIDFPYBJ-UHFFFAOYSA-N 5-chloro-2-[[2-(2-methoxyphenyl)-4-(4-methoxy-1,3-thiazol-2-yl)-5-methylpyrazol-3-yl]amino]benzoic acid Chemical compound COC1=CSC(C2=C(N(N=C2C)C=2C(=CC=CC=2)OC)NC=2C(=CC(Cl)=CC=2)C(O)=O)=N1 QRFDLOOIDFPYBJ-UHFFFAOYSA-N 0.000 claims 2
- 239000005541 ACE inhibitor Substances 0.000 claims 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 229940122199 Insulin secretagogue Drugs 0.000 claims 2
- 229940100389 Sulfonylurea Drugs 0.000 claims 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 2
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 2
- 239000003524 antilipemic agent Substances 0.000 claims 2
- 239000002876 beta blocker Substances 0.000 claims 2
- 229940097320 beta blocking agent Drugs 0.000 claims 2
- 239000000480 calcium channel blocker Substances 0.000 claims 2
- 239000002934 diuretic Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000002792 enkephalinase inhibitor Substances 0.000 claims 2
- 229940125753 fibrate Drugs 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 230000003228 microsomal effect Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 239000002461 renin inhibitor Substances 0.000 claims 2
- 229940086526 renin-inhibitors Drugs 0.000 claims 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 230000032258 transport Effects 0.000 claims 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 229940124681 11 beta HSD inhibitor Drugs 0.000 claims 1
- HDCLQSAPEAGUAR-UHFFFAOYSA-N 2-[[2-(2-chlorophenyl)-4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-5-methylpyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound S1C(C)=C(OCC)N=C1C1=C(NC=2C(=CC(OC)=CC=2)C(O)=O)N(C=2C(=CC=CC=2)Cl)N=C1C HDCLQSAPEAGUAR-UHFFFAOYSA-N 0.000 claims 1
- TZUCHNVNTMUPBQ-UHFFFAOYSA-N 2-[[2-(2-chlorophenyl)-4-(4-methoxy-1,3-thiazol-2-yl)-5-methylpyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound COC1=CSC(C2=C(N(N=C2C)C=2C(=CC=CC=2)Cl)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 TZUCHNVNTMUPBQ-UHFFFAOYSA-N 0.000 claims 1
- ADLBGAFLRDORRB-UHFFFAOYSA-N 2-[[2-(2-chlorophenyl)-4-(4-methoxy-5-methyl-1,3-thiazol-2-yl)-5-methylpyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound S1C(C)=C(OC)N=C1C1=C(NC=2C(=CC(OC)=CC=2)C(O)=O)N(C=2C(=CC=CC=2)Cl)N=C1C ADLBGAFLRDORRB-UHFFFAOYSA-N 0.000 claims 1
- YGKKVRRPCWWXJX-UHFFFAOYSA-N 2-[[2-(2-chlorophenyl)-4-(5-ethyl-4-methoxy-1,3-thiazol-2-yl)-5-methylpyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound COC1=C(CC)SC(C2=C(N(N=C2C)C=2C(=CC=CC=2)Cl)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 YGKKVRRPCWWXJX-UHFFFAOYSA-N 0.000 claims 1
- ZFZAEMUTEFIYAQ-UHFFFAOYSA-N 2-[[2-(2-methoxyphenyl)-4-(4-methoxy-1,3-thiazol-2-yl)-5-methylpyrazol-3-yl]amino]-5-methylbenzoic acid Chemical compound COC1=CSC(C2=C(N(N=C2C)C=2C(=CC=CC=2)OC)NC=2C(=CC(C)=CC=2)C(O)=O)=N1 ZFZAEMUTEFIYAQ-UHFFFAOYSA-N 0.000 claims 1
- IYIGHEAIRROOOJ-UHFFFAOYSA-N 2-[[4-(4,5-dimethyl-1,3-thiazol-2-yl)-5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=C(C=2SC(C)=C(C)N=2)C(C)=NN1C1=CC=CC=C1C IYIGHEAIRROOOJ-UHFFFAOYSA-N 0.000 claims 1
- RGGFDGLSJXTFSH-UHFFFAOYSA-N 2-[[4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-5-ethyl-2-(2-methoxyphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound S1C(C)=C(OCC)N=C1C1=C(NC=2C(=CC(OC)=CC=2)C(O)=O)N(C=2C(=CC=CC=2)OC)N=C1CC RGGFDGLSJXTFSH-UHFFFAOYSA-N 0.000 claims 1
- MWCAGCXRBPNNPY-UHFFFAOYSA-N 2-[[4-(4-ethyl-1,3-oxazol-2-yl)-5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound CCC1=COC(C2=C(N(N=C2C)C=2C(=CC=CC=2)C)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 MWCAGCXRBPNNPY-UHFFFAOYSA-N 0.000 claims 1
- JLXCBCIMXWTGPG-UHFFFAOYSA-N 2-[[4-(4-ethyl-1,3-thiazol-2-yl)-2-(2-methoxyphenyl)-5-methylpyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound CCC1=CSC(C2=C(N(N=C2C)C=2C(=CC=CC=2)OC)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 JLXCBCIMXWTGPG-UHFFFAOYSA-N 0.000 claims 1
- JKYDTNFPIQBIRF-UHFFFAOYSA-N 2-[[4-(4-ethyl-1,3-thiazol-2-yl)-2-(2-methoxyphenyl)-5-methylpyrazol-3-yl]amino]-5-methylbenzoic acid Chemical compound CCC1=CSC(C2=C(N(N=C2C)C=2C(=CC=CC=2)OC)NC=2C(=CC(C)=CC=2)C(O)=O)=N1 JKYDTNFPIQBIRF-UHFFFAOYSA-N 0.000 claims 1
- GJBAQIPMXKZJNW-UHFFFAOYSA-N 2-[[4-(5-ethyl-4-methoxy-1,3-thiazol-2-yl)-5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound COC1=C(CC)SC(C2=C(N(N=C2C)C=2C(=CC=CC=2)C)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 GJBAQIPMXKZJNW-UHFFFAOYSA-N 0.000 claims 1
- SSYBYVMOLUFFGZ-UHFFFAOYSA-N 2-[[5-ethyl-2-(2-methoxyphenyl)-4-(1,3-thiazol-2-yl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound N=1C=CSC=1C=1C(CC)=NN(C=2C(=CC=CC=2)OC)C=1NC1=CC=C(OC)C=C1C(O)=O SSYBYVMOLUFFGZ-UHFFFAOYSA-N 0.000 claims 1
- PJTXGRXRCUITBH-UHFFFAOYSA-N 2-[[5-ethyl-2-(2-methoxyphenyl)-4-(4-methoxy-1,3-thiazol-2-yl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound N=1C(OC)=CSC=1C=1C(CC)=NN(C=2C(=CC=CC=2)OC)C=1NC1=CC=C(OC)C=C1C(O)=O PJTXGRXRCUITBH-UHFFFAOYSA-N 0.000 claims 1
- HVLYAIBIXYUHJE-UHFFFAOYSA-N 2-[[5-ethyl-2-(2-methoxyphenyl)-4-(4-methoxy-1,3-thiazol-2-yl)pyrazol-3-yl]amino]-5-methylbenzoic acid Chemical compound N=1C(OC)=CSC=1C=1C(CC)=NN(C=2C(=CC=CC=2)OC)C=1NC1=CC=C(C)C=C1C(O)=O HVLYAIBIXYUHJE-UHFFFAOYSA-N 0.000 claims 1
- KYHAQPQUZAEBDO-UHFFFAOYSA-N 2-[[5-ethyl-2-(2-methoxyphenyl)-4-(4-methoxy-1,3-thiazol-2-yl)pyrazol-3-yl]amino]benzoic acid Chemical compound N=1C(OC)=CSC=1C=1C(CC)=NN(C=2C(=CC=CC=2)OC)C=1NC1=CC=CC=C1C(O)=O KYHAQPQUZAEBDO-UHFFFAOYSA-N 0.000 claims 1
- KJHRPJGNMJETLX-UHFFFAOYSA-N 2-[[5-ethyl-2-(2-methoxyphenyl)-4-(4-methyl-1,3-thiazol-2-yl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound N=1C(C)=CSC=1C=1C(CC)=NN(C=2C(=CC=CC=2)OC)C=1NC1=CC=C(OC)C=C1C(O)=O KJHRPJGNMJETLX-UHFFFAOYSA-N 0.000 claims 1
- IRHKXDQPYBOEMK-UHFFFAOYSA-N 2-[[5-ethyl-2-(2-methylphenyl)-4-(1,3-thiazol-2-yl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound N=1C=CSC=1C=1C(CC)=NN(C=2C(=CC=CC=2)C)C=1NC1=CC=C(OC)C=C1C(O)=O IRHKXDQPYBOEMK-UHFFFAOYSA-N 0.000 claims 1
- WWWSQZRCZZHQER-UHFFFAOYSA-N 2-[[5-ethyl-2-(2-methylphenyl)-4-(4-methyl-1,3-thiazol-2-yl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound N=1C(C)=CSC=1C=1C(CC)=NN(C=2C(=CC=CC=2)C)C=1NC1=CC=C(OC)C=C1C(O)=O WWWSQZRCZZHQER-UHFFFAOYSA-N 0.000 claims 1
- MPVJXLIBDZLKPL-UHFFFAOYSA-N 2-[[5-ethyl-4-(4-ethyl-1,3-thiazol-2-yl)-2-(2-methoxyphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound CCC1=CSC(C2=C(N(N=C2CC)C=2C(=CC=CC=2)OC)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 MPVJXLIBDZLKPL-UHFFFAOYSA-N 0.000 claims 1
- YBOCUHWKDATXSL-UHFFFAOYSA-N 2-[[5-ethyl-4-(4-ethyl-1,3-thiazol-2-yl)-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound CCC1=CSC(C2=C(N(N=C2CC)C=2C(=CC=CC=2)C)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 YBOCUHWKDATXSL-UHFFFAOYSA-N 0.000 claims 1
- QDXRIDVEAGXKRM-UHFFFAOYSA-N 2-[[5-ethyl-4-(4-methoxy-1,3-thiazol-2-yl)-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound N=1C(OC)=CSC=1C=1C(CC)=NN(C=2C(=CC=CC=2)C)C=1NC1=CC=C(OC)C=C1C(O)=O QDXRIDVEAGXKRM-UHFFFAOYSA-N 0.000 claims 1
- LGSPTOWHJAJECS-UHFFFAOYSA-N 2-[[5-ethyl-4-(4-methoxy-5-methyl-1,3-thiazol-2-yl)-2-(2-methoxyphenyl)pyrazol-3-yl]amino]-5-methylbenzoic acid Chemical compound N=1C(OC)=C(C)SC=1C=1C(CC)=NN(C=2C(=CC=CC=2)OC)C=1NC1=CC=C(C)C=C1C(O)=O LGSPTOWHJAJECS-UHFFFAOYSA-N 0.000 claims 1
- VFHQGAHHCPMWPF-UHFFFAOYSA-N 2-[[5-ethyl-4-(4-methoxy-5-methyl-1,3-thiazol-2-yl)-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound N=1C(OC)=C(C)SC=1C=1C(CC)=NN(C=2C(=CC=CC=2)C)C=1NC1=CC=C(OC)C=C1C(O)=O VFHQGAHHCPMWPF-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- REMZIDSEUXZXMJ-UHFFFAOYSA-N 5-chloro-2-[[4-(4-methoxy-5-methyl-1,3-thiazol-2-yl)-2-(2-methoxyphenyl)-5-methylpyrazol-3-yl]amino]benzoic acid Chemical compound S1C(C)=C(OC)N=C1C1=C(NC=2C(=CC(Cl)=CC=2)C(O)=O)N(C=2C(=CC=CC=2)OC)N=C1C REMZIDSEUXZXMJ-UHFFFAOYSA-N 0.000 claims 1
- NXWIGEDSJXSXMK-UHFFFAOYSA-N 5-ethyl-2-[[5-ethyl-4-(4-ethyl-1,3-thiazol-2-yl)-2-(2-methoxyphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound CCC1=CSC(C2=C(N(N=C2CC)C=2C(=CC=CC=2)OC)NC=2C(=CC(CC)=CC=2)C(O)=O)=N1 NXWIGEDSJXSXMK-UHFFFAOYSA-N 0.000 claims 1
- SLORYBSYHSCHNU-UHFFFAOYSA-N 5-methoxy-2-[[2-(2-methoxyphenyl)-4-(4-methoxy-1,3-thiazol-2-yl)-5-methylpyrazol-3-yl]amino]benzoic acid Chemical compound COC1=CSC(C2=C(N(N=C2C)C=2C(=CC=CC=2)OC)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 SLORYBSYHSCHNU-UHFFFAOYSA-N 0.000 claims 1
- PBNQNYRZSWHUBD-UHFFFAOYSA-N 5-methoxy-2-[[4-(4-methoxy-1,3-thiazol-2-yl)-5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound COC1=CSC(C2=C(N(N=C2C)C=2C(=CC=CC=2)C)NC=2C(=CC(OC)=CC=2)C(O)=O)=N1 PBNQNYRZSWHUBD-UHFFFAOYSA-N 0.000 claims 1
- PWMMWNOQYLABKH-UHFFFAOYSA-N 5-methoxy-2-[[4-(4-methoxy-5-methyl-1,3-thiazol-2-yl)-2-(2-methoxyphenyl)-5-methylpyrazol-3-yl]amino]benzoic acid Chemical compound S1C(C)=C(OC)N=C1C1=C(NC=2C(=CC(OC)=CC=2)C(O)=O)N(C=2C(=CC=CC=2)OC)N=C1C PWMMWNOQYLABKH-UHFFFAOYSA-N 0.000 claims 1
- KLEMQUVXVMVZSX-UHFFFAOYSA-N 5-methoxy-2-[[4-(4-methoxy-5-methyl-1,3-thiazol-2-yl)-5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound S1C(C)=C(OC)N=C1C1=C(NC=2C(=CC(OC)=CC=2)C(O)=O)N(C=2C(=CC=CC=2)C)N=C1C KLEMQUVXVMVZSX-UHFFFAOYSA-N 0.000 claims 1
- GQFUOTINEXOCPU-UHFFFAOYSA-N 5-methoxy-2-[[5-methyl-2-(2-methylphenyl)-4-(1,3-thiazol-2-yl)pyrazol-3-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=C(C=2SC=CN=2)C(C)=NN1C1=CC=CC=C1C GQFUOTINEXOCPU-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 1
- 229940097420 Diuretic Drugs 0.000 claims 1
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 claims 1
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 229940126033 PPAR agonist Drugs 0.000 claims 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 1
- 239000000400 angiotensin II type 1 receptor blocker Substances 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 239000000883 anti-obesity agent Substances 0.000 claims 1
- 229940125710 antiobesity agent Drugs 0.000 claims 1
- 229920000080 bile acid sequestrant Polymers 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 230000001882 diuretic effect Effects 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 239000004026 insulin derivative Substances 0.000 claims 1
- 230000003914 insulin secretion Effects 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- BNYHRGTXRPWASY-UHFFFAOYSA-N nonylsulfonylurea Chemical compound CCCCCCCCCS(=O)(=O)NC(N)=O BNYHRGTXRPWASY-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 1
- 230000000580 secretagogue effect Effects 0.000 claims 1
- 239000003352 sequestering agent Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57306604P | 2004-05-20 | 2004-05-20 | |
| PCT/US2005/017889 WO2005112923A2 (en) | 2004-05-20 | 2005-05-20 | 5-anilino-4-heteroarylpyrazole derivatives useful for the treatment of diabetes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007538102A JP2007538102A (ja) | 2007-12-27 |
| JP2007538102A5 true JP2007538102A5 (https=) | 2008-07-10 |
Family
ID=35428833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007527506A Pending JP2007538102A (ja) | 2004-05-20 | 2005-05-20 | 糖尿病の処置に有用な５−アニリノ−４−ヘテロアリールピラゾール誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20080009531A1 (https=) |
| EP (1) | EP1750698A4 (https=) |
| JP (1) | JP2007538102A (https=) |
| CA (1) | CA2567352A1 (https=) |
| WO (1) | WO2005112923A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007004733A1 (ja) * | 2005-07-06 | 2007-01-11 | Nippon Chemiphar Co., Ltd. | ペルオキシソーム増殖剤活性化受容体δの活性化剤 |
| US8324265B2 (en) | 2005-11-21 | 2012-12-04 | Shionogi & Co., Ltd. | Heterocyclic compounds having type I 11β hydroxysteroid dehydrogenase inhibitory activity |
| DE102007003036A1 (de) | 2006-12-20 | 2008-06-26 | Bayer Cropscience Ag | Pyrimidinylpyrazole |
| ES2535317T3 (es) | 2007-05-18 | 2015-05-08 | Shionogi & Co., Ltd. | Derivado heterocíclico que contiene nitrógeno que tiene actividad inhibidora de la 11 beta-hidroxiesteroide deshidrogenasa de tipo 1 |
| DE102008039083A1 (de) | 2008-08-21 | 2010-02-25 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Aminopyrazole und ihre Verwendung |
| DE102008039082A1 (de) | 2008-08-21 | 2010-02-25 | Bayer Schering Pharma Aktiengesellschaft | Azabicyclisch-substituierte 5-Aminopyrazole und ihre Verwendung |
| WO2016092559A1 (en) * | 2014-12-12 | 2016-06-16 | Oat & Iil India Laboratories Private Limited | Substituted pyrazole derivatives having activity as fungicides |
| WO2020227368A1 (en) * | 2019-05-08 | 2020-11-12 | Trustees Of Boston University | Hsp90 inhibitors and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000212141A (ja) * | 1999-01-13 | 2000-08-02 | Warner Lambert Co | ジアリ―ルアミン |
| US6989385B2 (en) * | 2000-12-21 | 2006-01-24 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| MXPA03009847A (es) * | 2001-04-27 | 2004-02-12 | Vertex Pharma | Inhibidores de cinasa derivados de pirazol. |
| US6989451B2 (en) * | 2002-06-04 | 2006-01-24 | Valeant Research & Development | Heterocyclic compounds and uses thereof |
| AR042067A1 (es) * | 2002-11-27 | 2005-06-08 | Bayer Pharmaceuticals Corp | Derivados de anilinopirazol utiles en el tratamiento de la diabetes |
-
2005
- 2005-05-20 CA CA002567352A patent/CA2567352A1/en not_active Abandoned
- 2005-05-20 WO PCT/US2005/017889 patent/WO2005112923A2/en not_active Ceased
- 2005-05-20 JP JP2007527506A patent/JP2007538102A/ja active Pending
- 2005-05-20 EP EP05756060A patent/EP1750698A4/en not_active Withdrawn
- 2005-05-20 US US11/596,959 patent/US20080009531A1/en not_active Abandoned
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