CA2567352A1 - 5-anilino-4-heteroarylpyrazole derivatives useful for the treatment of diabetes - Google Patents
5-anilino-4-heteroarylpyrazole derivatives useful for the treatment of diabetes Download PDFInfo
- Publication number
- CA2567352A1 CA2567352A1 CA002567352A CA2567352A CA2567352A1 CA 2567352 A1 CA2567352 A1 CA 2567352A1 CA 002567352 A CA002567352 A CA 002567352A CA 2567352 A CA2567352 A CA 2567352A CA 2567352 A1 CA2567352 A1 CA 2567352A1
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- Prior art keywords
- optionally substituted
- alkoxy
- methoxy
- group
- alkyl
- 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.)
- Abandoned
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- 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 52
- 238000011282 treatment Methods 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 238000000034 method Methods 0.000 claims abstract description 63
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- -1 NR4R4 Chemical group 0.000 claims description 108
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 85
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 71
- 125000005843 halogen group Chemical group 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 64
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 55
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 43
- 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 description 43
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 42
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 40
- 239000003814 drug Substances 0.000 claims description 39
- 125000004043 oxo group Chemical group O=* 0.000 claims description 39
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 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 description 30
- 229940079593 drug Drugs 0.000 claims description 30
- 239000003112 inhibitor Substances 0.000 claims description 27
- 239000008103 glucose Substances 0.000 claims description 25
- 229940125396 insulin Drugs 0.000 claims description 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 21
- 102000004877 Insulin Human genes 0.000 claims description 20
- 108090001061 Insulin Proteins 0.000 claims description 20
- 239000008177 pharmaceutical agent Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 239000000556 agonist Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 238000009472 formulation Methods 0.000 claims description 12
- 229940122199 Insulin secretagogue Drugs 0.000 claims description 10
- 229940122355 Insulin sensitizer Drugs 0.000 claims description 9
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 9
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 9
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 9
- 230000003914 insulin secretion Effects 0.000 claims description 9
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 8
- 229940100389 Sulfonylurea Drugs 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000000883 anti-obesity agent Substances 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 8
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 230000002440 hepatic effect Effects 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 239000002464 receptor antagonist Substances 0.000 claims description 7
- 229940044551 receptor antagonist Drugs 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 206010056997 Impaired fasting glucose Diseases 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- BNYHRGTXRPWASY-UHFFFAOYSA-N nonylsulfonylurea Chemical compound CCCCCCCCCS(=O)(=O)NC(N)=O BNYHRGTXRPWASY-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 239000005541 ACE inhibitor Substances 0.000 claims description 5
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 230000000580 secretagogue effect Effects 0.000 claims description 5
- 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 description 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 4
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 208000035180 MODY Diseases 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 208000029078 coronary artery disease Diseases 0.000 claims description 4
- 229940125753 fibrate Drugs 0.000 claims description 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 4
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 4
- 201000008980 hyperinsulinism Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 201000006950 maturity-onset diabetes of the young Diseases 0.000 claims description 4
- 229960003512 nicotinic acid Drugs 0.000 claims description 4
- 235000001968 nicotinic acid Nutrition 0.000 claims description 4
- 239000011664 nicotinic acid Substances 0.000 claims description 4
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 230000032258 transport Effects 0.000 claims description 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 description 3
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims description 3
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 3
- 239000003613 bile acid Substances 0.000 claims description 3
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- 229940096699 bile acid sequestrants Drugs 0.000 claims description 3
- 239000000480 calcium channel blocker Substances 0.000 claims description 3
- 239000002934 diuretic Substances 0.000 claims description 3
- 229940030606 diuretics Drugs 0.000 claims description 3
- 208000004104 gestational diabetes Diseases 0.000 claims description 3
- 239000003862 glucocorticoid Substances 0.000 claims description 3
- 230000003228 microsomal effect Effects 0.000 claims description 3
- 150000002823 nitrates Chemical class 0.000 claims description 3
- 239000002461 renin inhibitor Substances 0.000 claims description 3
- 229940086526 renin-inhibitors Drugs 0.000 claims description 3
- 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 description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 229940123208 Biguanide Drugs 0.000 claims description 2
- 108010051696 Growth Hormone Proteins 0.000 claims description 2
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 150000004283 biguanides Chemical class 0.000 claims description 2
- 239000000122 growth hormone Substances 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 208000028591 pheochromocytoma Diseases 0.000 claims description 2
- 230000004936 stimulating effect Effects 0.000 claims description 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 34
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 17
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 229940125710 antiobesity agent Drugs 0.000 claims 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 3
- 201000001421 hyperglycemia Diseases 0.000 claims 3
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 3
- 238000011321 prophylaxis Methods 0.000 claims 3
- 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
- 239000002792 enkephalinase inhibitor Substances 0.000 claims 2
- 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
- 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
- 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
- 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
- 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
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- 229960000999 sodium citrate dihydrate Drugs 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229960003339 sodium phosphate Drugs 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008227 sterile water for injection Substances 0.000 description 1
- 239000008229 sterile water for irrigation Substances 0.000 description 1
- 230000010009 steroidogenesis Effects 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940127230 sympathomimetic drug Drugs 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical class OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 239000003749 thyromimetic agent Substances 0.000 description 1
- 229950004437 tiqueside Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
- 229960004813 trichlormethiazide Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- WAAWARRPZBNTNS-UHFFFAOYSA-N trimethylbenzylammonium dichloroiodate Chemical compound ClI(=O)=O.ClI(=O)=O.C[N+](C)(C)CC1=CC=CC=C1 WAAWARRPZBNTNS-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000777 urocortin Substances 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229940002552 xenical Drugs 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57306604P | 2004-05-20 | 2004-05-20 | |
| US60/573,066 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2567352A1 true CA2567352A1 (en) | 2005-12-01 |
Family
ID=35428833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002567352A Abandoned CA2567352A1 (en) | 2004-05-20 | 2005-05-20 | 5-anilino-4-heteroarylpyrazole derivatives useful for the treatment of diabetes |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20080009531A1 (enExample) |
| EP (1) | EP1750698A4 (enExample) |
| JP (1) | JP2007538102A (enExample) |
| CA (1) | CA2567352A1 (enExample) |
| WO (1) | WO2005112923A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2007004733A1 (ja) * | 2005-07-06 | 2009-01-29 | 日本ケミファ株式会社 | ペルオキシソーム増殖剤活性化受容体δの活性化剤 |
| BRPI0618885A8 (pt) | 2005-11-21 | 2018-06-26 | Shionogi & Co | compostos heterocíclicos tendo atividade inibitória de 11beta-hidroxiesteroide deidrogenase tipo i |
| DE102007003036A1 (de) | 2006-12-20 | 2008-06-26 | Bayer Cropscience Ag | Pyrimidinylpyrazole |
| BRPI0811191A2 (pt) | 2007-05-18 | 2014-10-29 | Shionogi & Co | Derivado heterocíclico contendo nitrogênio tendo atividade inibitória para 11beta-hidroxiesteroide deidrogenase tipo 1 |
| DE102008039082A1 (de) | 2008-08-21 | 2010-02-25 | Bayer Schering Pharma Aktiengesellschaft | Azabicyclisch-substituierte 5-Aminopyrazole und ihre Verwendung |
| DE102008039083A1 (de) | 2008-08-21 | 2010-02-25 | Bayer Schering Pharma Aktiengesellschaft | 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 |
| AP2003002825A0 (en) * | 2000-12-21 | 2003-09-30 | Vertex Pharma | 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 JP JP2007527506A patent/JP2007538102A/ja active Pending
- 2005-05-20 WO PCT/US2005/017889 patent/WO2005112923A2/en not_active Ceased
- 2005-05-20 EP EP05756060A patent/EP1750698A4/en not_active Withdrawn
- 2005-05-20 US US11/596,959 patent/US20080009531A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20080009531A1 (en) | 2008-01-10 |
| JP2007538102A (ja) | 2007-12-27 |
| EP1750698A2 (en) | 2007-02-14 |
| WO2005112923A2 (en) | 2005-12-01 |
| EP1750698A4 (en) | 2010-06-02 |
| WO2005112923A3 (en) | 2006-09-14 |
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