KR20050085170A - 당뇨병 치료에 유용한 아닐리노피라졸 유도체 - Google Patents

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Publication number

KR20050085170A

KR20050085170A KR1020057009560A KR20057009560A KR20050085170A KR 20050085170 A KR20050085170 A KR 20050085170A KR 1020057009560 A KR1020057009560 A KR 1020057009560A KR 20057009560 A KR20057009560 A KR 20057009560A KR 20050085170 A KR20050085170 A KR 20050085170A

Authority

KR

South Korea

Prior art keywords

optionally substituted

alkoxy

alkyl

group

halo

Prior art date

2002-11-27

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.)

Withdrawn

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• Global Dossier
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• 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 50
• 238000011282 treatment Methods 0.000 title claims description 25
• CMAOIURPBUCSJE-UHFFFAOYSA-N n-phenyl-1h-pyrazol-5-amine Chemical class C=1C=CC=CC=1NC=1C=CNN=1 CMAOIURPBUCSJE-UHFFFAOYSA-N 0.000 title abstract description 4
• 238000000034 method Methods 0.000 claims abstract description 97
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
• 201000010099 disease Diseases 0.000 claims abstract description 18
• 150000001875 compounds Chemical class 0.000 claims description 178
• -1 NR 8 R 8 Chemical group 0.000 claims description 113
• 239000000203 mixture Substances 0.000 claims description 90
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 85
• 125000001424 substituent group Chemical group 0.000 claims description 82
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 62
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 53
• 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 52
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 50
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 47
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
• 239000003814 drug Substances 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
• 229940079593 drug Drugs 0.000 claims description 32
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 29
• 229940125396 insulin Drugs 0.000 claims description 27
• 102000004877 Insulin Human genes 0.000 claims description 25
• 108090001061 Insulin Proteins 0.000 claims description 25
• 239000003795 chemical substances by application Substances 0.000 claims description 25
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 14
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 13
• 230000003914 insulin secretion Effects 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000000217 alkyl group Chemical group 0.000 claims description 12
• 238000009472 formulation Methods 0.000 claims description 11
• 229940122199 Insulin secretagogue Drugs 0.000 claims description 10
• 229920000642 polymer Polymers 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 229940122355 Insulin sensitizer Drugs 0.000 claims description 9
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 8
• 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
• 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 8
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
• 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 description 7
• 208000008589 Obesity Diseases 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• BNYHRGTXRPWASY-UHFFFAOYSA-N nonylsulfonylurea Chemical compound CCCCCCCCCS(=O)(=O)NC(N)=O BNYHRGTXRPWASY-UHFFFAOYSA-N 0.000 claims description 7
• 235000020824 obesity Nutrition 0.000 claims description 7
• 230000000580 secretagogue effect Effects 0.000 claims description 7
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 7
• 206010056997 Impaired fasting glucose Diseases 0.000 claims description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
• 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims description 4
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
• 206010022489 Insulin Resistance Diseases 0.000 claims description 4
• 201000001421 hyperglycemia 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
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 239000011347 resin Substances 0.000 claims description 4
• 229920005989 resin Polymers 0.000 claims description 4
• 208000011580 syndromic disease Diseases 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 group 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
• 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 3
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 3
• 102000007399 Nuclear hormone receptor Human genes 0.000 claims description 3
• 108020005497 Nuclear hormone receptor Proteins 0.000 claims description 3
• 239000002220 antihypertensive agent Substances 0.000 claims description 3
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 3
• 239000003613 bile acid Substances 0.000 claims description 3
• 239000012472 biological sample Substances 0.000 claims description 3
• 208000035475 disorder Diseases 0.000 claims description 3
• 229940125753 fibrate Drugs 0.000 claims description 3
• 208000004104 gestational diabetes Diseases 0.000 claims description 3
• 239000003862 glucocorticoid Substances 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
• 230000000144 pharmacologic effect Effects 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 3
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
• 239000000122 growth hormone Substances 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 208000028591 pheochromocytoma Diseases 0.000 claims description 2
• 230000004936 stimulating effect Effects 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 63
• 229940126033 PPAR agonist Drugs 0.000 claims 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
• 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 5
• 239000008177 pharmaceutical agent Substances 0.000 claims 5
• 208000032928 Dyslipidaemia Diseases 0.000 claims 3
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims 3
• 208000017170 Lipid metabolism disease Diseases 0.000 claims 3
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims 3
• 201000008980 hyperinsulinism Diseases 0.000 claims 3
• 230000002265 prevention Effects 0.000 claims 3
• 229940030600 antihypertensive agent Drugs 0.000 claims 2
• 230000002440 hepatic effect Effects 0.000 claims 2
• 150000003018 phosphorus compounds Chemical class 0.000 claims 2
• 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
• IUUZXUVQYMPZGD-UHFFFAOYSA-N 2-[[4-(2,4-dimethoxyphenyl)-5-methyl-2-(2-methylphenyl)pyrazol-3-yl]amino]-5-methoxybenzoic acid Chemical compound COC1=CC(OC)=CC=C1C1=C(NC=2C(=CC(OC)=CC=2)C(O)=O)N(C=2C(=CC=CC=2)C)N=C1C IUUZXUVQYMPZGD-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
• 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
• 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
• 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
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