JP2006510728A5 - - Google Patents
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- JP2006510728A5 JP2006510728A5 JP2004570952A JP2004570952A JP2006510728A5 JP 2006510728 A5 JP2006510728 A5 JP 2006510728A5 JP 2004570952 A JP2004570952 A JP 2004570952A JP 2004570952 A JP2004570952 A JP 2004570952A JP 2006510728 A5 JP2006510728 A5 JP 2006510728A5
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- JP
- Japan
- Prior art keywords
- optionally substituted
- alkoxy
- alkyl
- halo
- group
- 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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- 125000001475 halogen functional group Chemical group 0.000 claims 63
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 57
- 125000001424 substituent group Chemical group 0.000 claims 54
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 50
- -1 CF 3 Chemical group 0.000 claims 41
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 33
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims 31
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 19
- 125000001188 haloalkyl group Chemical group 0.000 claims 19
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 13
- 206010012601 diabetes mellitus Diseases 0.000 claims 13
- 239000003814 drug Substances 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
- 229940079593 drug Drugs 0.000 claims 4
- 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 4
- 238000000034 method Methods 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 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 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 239000008103 glucose Substances 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 2
- 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
- 229940077274 Alpha glucosidase inhibitor Drugs 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
- 229940122199 Insulin secretagogue Drugs 0.000 claims 2
- 229940122355 Insulin sensitizer Drugs 0.000 claims 2
- 229940126033 PPAR agonist Drugs 0.000 claims 2
- 229940100389 Sulfonylurea Drugs 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 2
- 239000000883 anti-obesity agent Substances 0.000 claims 2
- 229940030600 antihypertensive agent Drugs 0.000 claims 2
- 239000002220 antihypertensive agent Substances 0.000 claims 2
- 229940125710 antiobesity agent Drugs 0.000 claims 2
- 150000008366 benzophenones Chemical group 0.000 claims 2
- 229920000080 bile acid sequestrant Polymers 0.000 claims 2
- 239000012472 biological sample Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000029142 excretion Effects 0.000 claims 2
- 229940125753 fibrate Drugs 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000006377 halopyridyl group Chemical group 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- BNYHRGTXRPWASY-UHFFFAOYSA-N nonylsulfonylurea Chemical compound CCCCCCCCCS(=O)(=O)NC(N)=O BNYHRGTXRPWASY-UHFFFAOYSA-N 0.000 claims 2
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 230000000580 secretagogue effect Effects 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 2
- TVYNJEQUZKNBAI-UHFFFAOYSA-N 2-[(2,5-diphenylpyrazol-3-yl)amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 TVYNJEQUZKNBAI-UHFFFAOYSA-N 0.000 claims 1
- CWUFCHYCMHXCMB-UHFFFAOYSA-N 2-[(5-tert-butyl-2-methylpyrazol-3-yl)amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C(C)(C)C)=NN1C CWUFCHYCMHXCMB-UHFFFAOYSA-N 0.000 claims 1
- PTPTXMIUFHELGS-UHFFFAOYSA-N 2-[(5-tert-butyl-2-phenylpyrazol-3-yl)amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C(C)(C)C)=NN1C1=CC=CC=C1 PTPTXMIUFHELGS-UHFFFAOYSA-N 0.000 claims 1
- IEOICNMIUQLXOE-UHFFFAOYSA-N 2-[[2-(2,6-dimethylphenyl)-5-(1-methylcyclopropyl)pyrazol-3-yl]amino]benzoic acid Chemical compound CC1=CC=CC(C)=C1N1C(NC=2C(=CC=CC=2)C(O)=O)=CC(C2(C)CC2)=N1 IEOICNMIUQLXOE-UHFFFAOYSA-N 0.000 claims 1
- RYCVKUCWFFFSJE-UHFFFAOYSA-N 2-[[2-(2,6-dimethylphenyl)-5-(3,3,3-trifluoropropyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(CCC(F)(F)F)=NN1C1=C(C)C=CC=C1C RYCVKUCWFFFSJE-UHFFFAOYSA-N 0.000 claims 1
- NHKSFTWZJYECNC-UHFFFAOYSA-N 2-[[4-(2-fluorophenyl)-5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=C(C=2C(=CC=CC=2)F)C(C)=NN1C1=CC=CC=C1C NHKSFTWZJYECNC-UHFFFAOYSA-N 0.000 claims 1
- WXQAIZBHCIUKRG-UHFFFAOYSA-N 2-[[5-(3-methoxyphenyl)-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methylbenzoic acid Chemical compound COC1=CC=CC(C2=NN(C(NC=3C(=CC(C)=CC=3)C(O)=O)=C2)C=2C(=CC=CC=2)C)=C1 WXQAIZBHCIUKRG-UHFFFAOYSA-N 0.000 claims 1
- CDCPTBGPKQMRED-UHFFFAOYSA-N 2-[[5-(3-methoxyphenyl)-2-(2-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound COC1=CC=CC(C2=NN(C(NC=3C(=CC=CC=3)C(O)=O)=C2)C=2C(=CC=CC=2)C)=C1 CDCPTBGPKQMRED-UHFFFAOYSA-N 0.000 claims 1
- QFFAKBRCYHZZNT-UHFFFAOYSA-N 2-[[5-(4-fluorophenyl)-2-(2-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound CC1=CC=CC=C1N1C(NC=2C(=CC=CC=2)C(O)=O)=CC(C=2C=CC(F)=CC=2)=N1 QFFAKBRCYHZZNT-UHFFFAOYSA-N 0.000 claims 1
- GYQDDDHUXXWBRB-UHFFFAOYSA-N 2-[[5-ethyl-4-(6-methoxypyridin-3-yl)-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound C=1C=C(OC)N=CC=1C=1C(CC)=NN(C=2C(=CC=CC=2)C)C=1NC1=CC=C(OC)C=C1C(O)=O GYQDDDHUXXWBRB-UHFFFAOYSA-N 0.000 claims 1
- JEHNTRZLCOFDBK-UHFFFAOYSA-N 2-[[5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]benzamide Chemical compound C=1C=CC=C(C)C=1N1N=C(C)C=C1NC1=CC=CC=C1C(N)=O JEHNTRZLCOFDBK-UHFFFAOYSA-N 0.000 claims 1
- XWFUKNZKYZNJCG-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2,3-dimethylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C(C)(C)C)=NN1C1=CC=CC(C)=C1C XWFUKNZKYZNJCG-UHFFFAOYSA-N 0.000 claims 1
- WYDDJHVVQWLCPB-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2,6-dimethylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C(C)(C)C)=NN1C1=C(C)C=CC=C1C WYDDJHVVQWLCPB-UHFFFAOYSA-N 0.000 claims 1
- STVZMCWHWRPKLW-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2,6-dimethylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound CC1=CC=CC(C)=C1N1C(NC=2C(=CC=CC=2)C(O)=O)=CC(C(C)(C)C)=N1 STVZMCWHWRPKLW-UHFFFAOYSA-N 0.000 claims 1
- DRDCSOYROQGYBO-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2-ethoxyphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound CCOC1=CC=CC=C1N1C(NC=2C(=CC(OC)=CC=2)C(O)=O)=CC(C(C)(C)C)=N1 DRDCSOYROQGYBO-UHFFFAOYSA-N 0.000 claims 1
- DRCPLNPPNOXXAJ-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2-ethoxyphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound CCOC1=CC=CC=C1N1C(NC=2C(=CC=CC=2)C(O)=O)=CC(C(C)(C)C)=N1 DRCPLNPPNOXXAJ-UHFFFAOYSA-N 0.000 claims 1
- UNSXSYFBXLWJLR-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2-methoxy-5-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound COC1=CC=C(C)C=C1N1C(NC=2C(=CC=CC=2)C(O)=O)=CC(C(C)(C)C)=N1 UNSXSYFBXLWJLR-UHFFFAOYSA-N 0.000 claims 1
- RPJMQJRLXOLESP-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2-methoxy-6-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C(C)(C)C)=NN1C1=C(C)C=CC=C1OC RPJMQJRLXOLESP-UHFFFAOYSA-N 0.000 claims 1
- OIDPPOQHTRYROA-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2-methoxyphenyl)-4-methylpyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=C(C)C(C(C)(C)C)=NN1C1=CC=CC=C1OC OIDPPOQHTRYROA-UHFFFAOYSA-N 0.000 claims 1
- DRZLAROFLUFDGC-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2-methoxyphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C(C)(C)C)=NN1C1=CC=CC=C1OC DRZLAROFLUFDGC-UHFFFAOYSA-N 0.000 claims 1
- DPXRSDZSUCTWBU-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C(C)(C)C)=NN1C1=CC=CC=C1C DPXRSDZSUCTWBU-UHFFFAOYSA-N 0.000 claims 1
- JVYBEYCMSGSXBT-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(2-methylsulfanylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC(C(C)(C)C)=NN1C1=CC=CC=C1SC JVYBEYCMSGSXBT-UHFFFAOYSA-N 0.000 claims 1
- OSOFUBGPFZFAOQ-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(5-fluoro-2-methylphenyl)pyrazol-3-yl]amino]-6-fluorobenzoic acid Chemical compound CC1=CC=C(F)C=C1N1C(NC=2C(=C(F)C=CC=2)C(O)=O)=CC(C(C)(C)C)=N1 OSOFUBGPFZFAOQ-UHFFFAOYSA-N 0.000 claims 1
- WQNLZMSCTZADHA-UHFFFAOYSA-N 2-[[5-tert-butyl-2-(5-fluoro-2-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound CC1=CC=C(F)C=C1N1C(NC=2C(=CC=CC=2)C(O)=O)=CC(C(C)(C)C)=N1 WQNLZMSCTZADHA-UHFFFAOYSA-N 0.000 claims 1
- XPSNAKCMUNSHOI-UHFFFAOYSA-N 2-fluoro-6-[[2-(2-methylphenyl)-5-(4-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound C1=CC(C)=CC=C1C1=NN(C=2C(=CC=CC=2)C)C(NC=2C(=C(F)C=CC=2)C(O)=O)=C1 XPSNAKCMUNSHOI-UHFFFAOYSA-N 0.000 claims 1
- RFYHZTKILJZFKL-UHFFFAOYSA-N 2-fluoro-6-[[5-(4-fluorophenyl)-2-(2-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound CC1=CC=CC=C1N1C(NC=2C(=C(F)C=CC=2)C(O)=O)=CC(C=2C=CC(F)=CC=2)=N1 RFYHZTKILJZFKL-UHFFFAOYSA-N 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- LVSQVORYVDULSC-UHFFFAOYSA-N 5-methoxy-2-[[2-(2-methoxyphenyl)-5-methyl-4-phenylpyrazol-3-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(C)=NN1C1=CC=CC=C1OC LVSQVORYVDULSC-UHFFFAOYSA-N 0.000 claims 1
- OCZOTOZJCRJWAU-UHFFFAOYSA-N 5-methoxy-2-[[2-(2-methylphenyl)-4-pyridin-4-yl-5-(trifluoromethyl)pyrazol-3-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=C(C=2C=CN=CC=2)C(C(F)(F)F)=NN1C1=CC=CC=C1C OCZOTOZJCRJWAU-UHFFFAOYSA-N 0.000 claims 1
- DTZMRSQXUMFQTF-UHFFFAOYSA-N 5-methoxy-2-[[4-(4-methoxyphenyl)-2-(2-methylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]amino]benzoic acid Chemical compound C1=CC(OC)=CC=C1C(C(=NN1C=2C(=CC=CC=2)C)C(F)(F)F)=C1NC1=CC=C(OC)C=C1C(O)=O DTZMRSQXUMFQTF-UHFFFAOYSA-N 0.000 claims 1
- VKYSDBRFDIGIDK-UHFFFAOYSA-N 5-methoxy-2-[[4-(6-methoxypyridin-3-yl)-5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=C(C=2C=NC(OC)=CC=2)C(C)=NN1C1=CC=CC=C1C VKYSDBRFDIGIDK-UHFFFAOYSA-N 0.000 claims 1
- KLUDNRDSXNPPLA-UHFFFAOYSA-N 5-methoxy-2-[[5-(3-methoxyphenyl)-2-(2-methylphenyl)pyrazol-3-yl]amino]benzoic acid Chemical compound COC1=CC=CC(C2=NN(C(NC=3C(=CC(OC)=CC=3)C(O)=O)=C2)C=2C(=CC=CC=2)C)=C1 KLUDNRDSXNPPLA-UHFFFAOYSA-N 0.000 claims 1
- XHQHCXZEPXDRLH-UHFFFAOYSA-N 5-methoxy-2-[[5-methyl-2-(2-methylphenyl)-4-phenylpyrazol-3-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(C)=NN1C1=CC=CC=C1C XHQHCXZEPXDRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 102000018997 Growth Hormone Human genes 0.000 claims 1
- 108010051696 Growth Hormone Proteins 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 claims 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 208000004104 gestational diabetes Diseases 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- 239000000122 growth hormone Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 230000003914 insulin secretion Effects 0.000 claims 1
- 230000000366 juvenile effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 230000008506 pathogenesis Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000028591 pheochromocytoma Diseases 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42991702P | 2002-11-27 | 2002-11-27 | |
| US49821403P | 2003-08-27 | 2003-08-27 | |
| PCT/US2003/037829 WO2004050651A1 (en) | 2002-11-27 | 2003-11-25 | Anilinopyrazole derivatives useful for the treatment of diabetes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006510728A JP2006510728A (ja) | 2006-03-30 |
| JP2006510728A5 true JP2006510728A5 (https=) | 2007-01-11 |
Family
ID=32474531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004570952A Pending JP2006510728A (ja) | 2002-11-27 | 2003-11-25 | 糖尿病の処置に有用なアニリノピラゾール誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7265144B2 (https=) |
| EP (1) | EP1567517A1 (https=) |
| JP (1) | JP2006510728A (https=) |
| KR (1) | KR20050085170A (https=) |
| AR (1) | AR042067A1 (https=) |
| AU (2) | AU2003295890A1 (https=) |
| BR (1) | BR0316723A (https=) |
| CA (1) | CA2507186A1 (https=) |
| HN (1) | HN2003000379A (https=) |
| MX (1) | MXPA05004621A (https=) |
| MY (1) | MY141528A (https=) |
| PE (1) | PE20040907A1 (https=) |
| PL (1) | PL377164A1 (https=) |
| TW (1) | TW200418803A (https=) |
| UY (1) | UY28098A1 (https=) |
| WO (2) | WO2004050650A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007538102A (ja) * | 2004-05-20 | 2007-12-27 | バイエル・フアーマシユーチカルズ・コーポレーシヨン | 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 |
| ES2395952T3 (es) | 2005-03-16 | 2013-02-18 | Toyama Chemical Co., Ltd. | Nuevo derivado del ácido antranílico o una sal del mismo |
| JP5193861B2 (ja) * | 2005-07-07 | 2013-05-08 | アボット・ラボラトリーズ | アポトーシス促進剤 |
| CA2620425A1 (en) * | 2005-08-31 | 2007-03-08 | Bayer Healthcare Llc | Anilinopyrazole derivatives useful for the treatment of diabetes |
| WO2007129195A2 (en) * | 2006-05-04 | 2007-11-15 | Pfizer Products Inc. | 4-pyrimidine-5-amino-pyrazole compounds |
| US8022217B2 (en) | 2006-07-31 | 2011-09-20 | Cadila Healthcare Limited | Compounds suitable as modulators of HDL |
| WO2008042639A1 (en) | 2006-10-02 | 2008-04-10 | Irm Llc | Compounds and compositions as protein kinase inhibitors |
| WO2008093639A1 (ja) | 2007-01-29 | 2008-08-07 | Takeda Pharmaceutical Company Limited | ピラゾール化合物 |
| US20110034521A1 (en) * | 2007-09-28 | 2011-02-10 | Alan Jacobson | Compounds and methods for treating zinc matrix metalloprotease dependent diseases |
| 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 |
| CA2737437A1 (en) * | 2008-09-19 | 2010-03-25 | Absolute Science, Inc. | Methods of treating a botulinum toxin related condition in a subject |
| WO2010034657A1 (en) * | 2008-09-25 | 2010-04-01 | F. Hoffmann-La Roche Ag | 3-amino-indazole or 3-amino-4,5,6,7-tetrahydro-indazole derivatives |
| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TWI568721B (zh) | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
| WO2014007228A1 (ja) * | 2012-07-03 | 2014-01-09 | 小野薬品工業株式会社 | ソマトスタチン受容体作動活性を有する化合物およびその医薬用途 |
| CN103074693A (zh) * | 2013-01-18 | 2013-05-01 | 桐昆集团股份有限公司 | 带双导丝辊的poy纺丝卷绕装置 |
| EP3663287B1 (en) | 2013-12-23 | 2023-09-20 | Amazentis SA | Process scale synthesis of urolithins |
| EP3805213A3 (en) * | 2015-06-18 | 2021-06-09 | Nippon Soda Co., Ltd. | 1-(2-(ethylsulfonyl)-phenyl)-4-(phenyl)-1h-1,2,3-triazole and 4-(2-(ethylsulfonyl)-phenyl)-1-(phenyl)-1h-1,2,3-triazole and related compounds derivatives as pesticides |
| EP3632904B1 (en) * | 2017-05-26 | 2022-04-20 | Jiangsu Atom Bioscience and Pharmaceutical Co., Ltd. | Urat1 inhibitors for promoting uric acid excretion |
| US11312722B2 (en) * | 2019-05-08 | 2022-04-26 | Trustees Of Boston University | Hsp90 inhibitors and uses thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL263568A (https=) | 1960-04-14 | |||
| US3790576A (en) * | 1972-03-20 | 1974-02-05 | Parke Davis & Co | 9 substituted 4,9-dihydro-1,3,4,4-tetraalkyl-1h-pyrazolo(3,4-b)quinolines |
| WO1993019054A1 (en) | 1992-03-26 | 1993-09-30 | Dowelanco | N-heterocyclic nitro anilines as fungicides |
| WO1996014843A2 (en) | 1994-11-10 | 1996-05-23 | Cor Therapeutics, Inc. | Pharmaceutical pyrazole compositions useful as inhibitors of protein kinases |
| DE19532066A1 (de) | 1995-08-31 | 1997-03-06 | Bayer Ag | Substituierte 5-Aminopyrazole |
| FR2763334A1 (fr) | 1997-05-13 | 1998-11-20 | Lipha | Derives anthraniliques |
| US5998424A (en) | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
| US5942520A (en) | 1998-01-27 | 1999-08-24 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells by exposure to substituted N-cycloalkylmethyl-1-H-pyrazolo (3,4-B) quinolone-4 amines |
| WO2004076414A2 (en) * | 2003-02-27 | 2004-09-10 | Smithkline Beecham Corporation | Novel compounds |
-
2003
- 2003-11-18 AR ARP030104252A patent/AR042067A1/es unknown
- 2003-11-21 US US10/719,485 patent/US7265144B2/en not_active Expired - Fee Related
- 2003-11-21 WO PCT/US2003/037578 patent/WO2004050650A1/en not_active Ceased
- 2003-11-21 AU AU2003295890A patent/AU2003295890A1/en not_active Abandoned
- 2003-11-25 KR KR1020057009560A patent/KR20050085170A/ko not_active Withdrawn
- 2003-11-25 JP JP2004570952A patent/JP2006510728A/ja active Pending
- 2003-11-25 PL PL377164A patent/PL377164A1/pl not_active Application Discontinuation
- 2003-11-25 BR BR0316723-2A patent/BR0316723A/pt not_active IP Right Cessation
- 2003-11-25 MX MXPA05004621A patent/MXPA05004621A/es not_active Application Discontinuation
- 2003-11-25 WO PCT/US2003/037829 patent/WO2004050651A1/en not_active Ceased
- 2003-11-25 AU AU2003297565A patent/AU2003297565A1/en not_active Abandoned
- 2003-11-25 EP EP03812454A patent/EP1567517A1/en not_active Withdrawn
- 2003-11-25 CA CA002507186A patent/CA2507186A1/en not_active Abandoned
- 2003-11-26 TW TW092133242A patent/TW200418803A/zh unknown
- 2003-11-26 PE PE2003001198A patent/PE20040907A1/es not_active Application Discontinuation
- 2003-11-26 UY UY28098A patent/UY28098A1/es not_active Application Discontinuation
- 2003-11-26 HN HN2003000379A patent/HN2003000379A/es unknown
- 2003-11-27 MY MYPI20034545A patent/MY141528A/en unknown
-
2007
- 2007-08-31 US US11/897,620 patent/US20080064734A1/en not_active Abandoned
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