JP2002302458A

JP2002302458A - 併用薬

併用薬

Info

Publication number: JP2002302458A
Authority: JP; Japan
Prior art keywords: pyridyl; group; thiazol; methylphenyl; substituent
Prior art date: 2000-12-26
Legal status : Abandoned

Application number

JP2001392778A

Other languages

English (en)

Japanese (ja)

Other versions

JP2002302458A5 (enExample

Inventor

Shigenori Ookawa

滋紀大川

Kenichi Naruo

憲一成尾

Seiji Miwatari

誠司見渡

Current Assignee

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date

2000-12-26

Filing date

2001-12-25

Publication date

2002-10-18

2001-12-25 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

2001-12-25 Priority to JP2001392778A priority Critical patent/JP2002302458A/ja

2002-10-18 Publication of JP2002302458A publication Critical patent/JP2002302458A/ja

2005-05-19 Publication of JP2002302458A5 publication Critical patent/JP2002302458A5/ja

Status Abandoned legal-status Critical Current

Links

239000003814 drug Substances 0.000 title claims abstract description 112
229940079593 drug Drugs 0.000 claims abstract description 81
239000003112 inhibitor Substances 0.000 claims abstract description 53
102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims abstract description 42
108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 42
230000006433 tumor necrosis factor production Effects 0.000 claims abstract description 33
229940043355 kinase inhibitor Drugs 0.000 claims abstract description 26
239000003757 phosphotransferase inhibitor Substances 0.000 claims abstract description 26
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims abstract description 20
108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 17
230000003092 anti-cytokine Effects 0.000 claims abstract description 17
150000003431 steroids Chemical class 0.000 claims abstract description 17
239000002988 disease modifying antirheumatic drug Substances 0.000 claims abstract description 16
239000002955 immunomodulating agent Substances 0.000 claims abstract description 15
229940121354 immunomodulator Drugs 0.000 claims abstract description 15
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims abstract description 9
239000003795 chemical substances by application Substances 0.000 claims abstract description 6
229940123907 Disease modifying antirheumatic drug Drugs 0.000 claims abstract description 5
-1 1,3-thiazole compound Chemical class 0.000 claims description 576
125000001424 substituent group Chemical group 0.000 claims description 295
150000001875 compounds Chemical class 0.000 claims description 241
150000003839 salts Chemical class 0.000 claims description 81
229910052717 sulfur Inorganic materials 0.000 claims description 79
229910052757 nitrogen Inorganic materials 0.000 claims description 69
125000003118 aryl group Chemical group 0.000 claims description 66
125000000217 alkyl group Chemical group 0.000 claims description 65
125000005843 halogen group Chemical group 0.000 claims description 65
125000003277 amino group Chemical group 0.000 claims description 63
125000005842 heteroatom Chemical group 0.000 claims description 61
125000000623 heterocyclic group Chemical group 0.000 claims description 61
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 61
125000004434 sulfur atom Chemical group 0.000 claims description 59
150000002430 hydrocarbons Chemical class 0.000 claims description 58
229910052799 carbon Inorganic materials 0.000 claims description 57
125000004430 oxygen atom Chemical group O* 0.000 claims description 55
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
125000004076 pyridyl group Chemical group 0.000 claims description 50
125000002252 acyl group Chemical group 0.000 claims description 39
239000004215 Carbon black (E152) Substances 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 28
150000001412 amines Chemical class 0.000 claims description 28
229930195733 hydrocarbon Natural products 0.000 claims description 28
239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims description 28
238000000034 method Methods 0.000 claims description 24
208000010125 myocardial infarction Diseases 0.000 claims description 22
208000011231 Crohn disease Diseases 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
206010006895 Cachexia Diseases 0.000 claims description 17
229940122696 MAP kinase inhibitor Drugs 0.000 claims description 17
125000002947 alkylene group Chemical group 0.000 claims description 17
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 16
208000030507 AIDS Diseases 0.000 claims description 15
206010061218 Inflammation Diseases 0.000 claims description 15
201000008937 atopic dermatitis Diseases 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
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125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 14
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229940124597 therapeutic agent Drugs 0.000 claims description 14
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239000003435 antirheumatic agent Substances 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
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206010003210 Arteriosclerosis Diseases 0.000 claims description 11
208000014644 Brain disease Diseases 0.000 claims description 11
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206010007556 Cardiac failure acute Diseases 0.000 claims description 11
206010007558 Cardiac failure chronic Diseases 0.000 claims description 11
206010007559 Cardiac failure congestive Diseases 0.000 claims description 11
206010008111 Cerebral haemorrhage Diseases 0.000 claims description 11
208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims description 11
208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims description 11
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201000009906 Meningitis Diseases 0.000 claims description 11
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206010035664 Pneumonia Diseases 0.000 claims description 11
208000001647 Renal Insufficiency Diseases 0.000 claims description 11
201000010001 Silicosis Diseases 0.000 claims description 11
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208000011775 arteriosclerosis disease Diseases 0.000 claims description 11
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201000011510 cancer Diseases 0.000 claims description 11
206010008118 cerebral infarction Diseases 0.000 claims description 11
230000015271 coagulation Effects 0.000 claims description 11
238000005345 coagulation Methods 0.000 claims description 11
238000000502 dialysis Methods 0.000 claims description 11
208000006454 hepatitis Diseases 0.000 claims description 11
231100000283 hepatitis Toxicity 0.000 claims description 11
201000006370 kidney failure Diseases 0.000 claims description 11
201000008383 nephritis Diseases 0.000 claims description 11
229940002612 prodrug Drugs 0.000 claims description 11
239000000651 prodrug Substances 0.000 claims description 11
230000000069 prophylactic effect Effects 0.000 claims description 11
201000003651 pulmonary sarcoidosis Diseases 0.000 claims description 11
208000008128 pulmonary tuberculosis Diseases 0.000 claims description 11
208000020431 spinal cord injury Diseases 0.000 claims description 11
230000009885 systemic effect Effects 0.000 claims description 11
208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims description 10
208000001953 Hypotension Diseases 0.000 claims description 10
206010000891 acute myocardial infarction Diseases 0.000 claims description 10
201000000448 autoimmune hemolytic anemia Diseases 0.000 claims description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
230000001684 chronic effect Effects 0.000 claims description 10
230000036543 hypotension Effects 0.000 claims description 10
201000008482 osteoarthritis Diseases 0.000 claims description 10
238000004393 prognosis Methods 0.000 claims description 10
208000026872 Addison Disease Diseases 0.000 claims description 9
206010009900 Colitis ulcerative Diseases 0.000 claims description 9
201000006704 Ulcerative Colitis Diseases 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 9
208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims description 9
238000002054 transplantation Methods 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 5
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 4
WCKYFUICHIUXND-UHFFFAOYSA-N 4-[2-butyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-n-(2-phenylethyl)pyridin-2-amine Chemical compound S1C(CCCC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NCCC1=CC=CC=C1 WCKYFUICHIUXND-UHFFFAOYSA-N 0.000 claims description 4
CPOSJEHRNPTYDH-UHFFFAOYSA-N 4-[4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]-n-(3-phenylpropyl)pyridin-2-amine Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(NCCCC=3C=CC=CC=3)N=CC=2)=C1 CPOSJEHRNPTYDH-UHFFFAOYSA-N 0.000 claims description 4
KVEWTWVMAGNFJU-UHFFFAOYSA-N 4-[4-(3-methylphenyl)-2-propyl-1,3-thiazol-5-yl]-n-(3-phenylpropyl)pyridin-2-amine Chemical compound S1C(CCC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NCCCC1=CC=CC=C1 KVEWTWVMAGNFJU-UHFFFAOYSA-N 0.000 claims description 4
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
HEKAIDKUDLCBRU-UHFFFAOYSA-N N-[4-[2-ethyl-4-(3-methylphenyl)-5-thiazolyl]-2-pyridinyl]benzamide Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)C1=CC=CC=C1 HEKAIDKUDLCBRU-UHFFFAOYSA-N 0.000 claims description 4
150000007942 carboxylates Chemical class 0.000 claims description 4
DEBAAZLQBLIHOY-UHFFFAOYSA-N n-[4-[2-(4-fluorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-2-phenylacetamide Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(F)=CC=2)C=2C=C(NC(=O)CC=3C=CC=CC=3)N=CC=2)=C1 DEBAAZLQBLIHOY-UHFFFAOYSA-N 0.000 claims description 4
BFOKBWPFXFDYML-UHFFFAOYSA-N n-[4-[2-(4-fluorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-3-phenylpropanamide Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(F)=CC=2)C=2C=C(NC(=O)CCC=3C=CC=CC=3)N=CC=2)=C1 BFOKBWPFXFDYML-UHFFFAOYSA-N 0.000 claims description 4
JHSFUGLKBDOULU-UHFFFAOYSA-N n-[4-[2-(4-fluorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]benzamide Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(F)=CC=2)C=2C=C(NC(=O)C=3C=CC=CC=3)N=CC=2)=C1 JHSFUGLKBDOULU-UHFFFAOYSA-N 0.000 claims description 4
VEZJXQNKSYPLCY-UHFFFAOYSA-N n-[4-[2-butyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C(CCCC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)CCC1=CC=CC=C1 VEZJXQNKSYPLCY-UHFFFAOYSA-N 0.000 claims description 4
CMSCQBAHJRZXDI-UHFFFAOYSA-N n-[4-[2-butyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]benzamide Chemical compound S1C(CCCC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)C1=CC=CC=C1 CMSCQBAHJRZXDI-UHFFFAOYSA-N 0.000 claims description 4
IKWWNWZDGSCJRW-UHFFFAOYSA-N n-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-2-phenylacetamide Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)CC1=CC=CC=C1 IKWWNWZDGSCJRW-UHFFFAOYSA-N 0.000 claims description 4
XLMIKSYZFWHWMU-UHFFFAOYSA-N n-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)CCC1=CC=CC=C1 XLMIKSYZFWHWMU-UHFFFAOYSA-N 0.000 claims description 4
OIWPBELDCSJQPD-UHFFFAOYSA-N n-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-4-phenylbutanamide Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)CCCC1=CC=CC=C1 OIWPBELDCSJQPD-UHFFFAOYSA-N 0.000 claims description 4
USKHXTHUERIOSE-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-(4-methylsulfanylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-2-phenylacetamide Chemical compound C1=CC(SC)=CC=C1C1=NC(C=2C=C(C)C=CC=2)=C(C=2C=C(NC(=O)CC=3C=CC=CC=3)N=CC=2)S1 USKHXTHUERIOSE-UHFFFAOYSA-N 0.000 claims description 4
DKPFMWKBOLOUJQ-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-(4-methylsulfanylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-3-phenylpropanamide Chemical compound C1=CC(SC)=CC=C1C1=NC(C=2C=C(C)C=CC=2)=C(C=2C=C(NC(=O)CCC=3C=CC=CC=3)N=CC=2)S1 DKPFMWKBOLOUJQ-UHFFFAOYSA-N 0.000 claims description 4
JYNRYHSNQFWROO-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-(4-methylsulfanylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]benzamide Chemical compound C1=CC(SC)=CC=C1C1=NC(C=2C=C(C)C=CC=2)=C(C=2C=C(NC(=O)C=3C=CC=CC=3)N=CC=2)S1 JYNRYHSNQFWROO-UHFFFAOYSA-N 0.000 claims description 4
DWRZQPYLTVJMKG-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-2-phenylacetamide Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(NC(=O)CC=3C=CC=CC=3)N=CC=2)=C1 DWRZQPYLTVJMKG-UHFFFAOYSA-N 0.000 claims description 4
QFFMVMUPGHCQTC-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-3-phenylpropanamide Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(NC(=O)CCC=3C=CC=CC=3)N=CC=2)=C1 QFFMVMUPGHCQTC-UHFFFAOYSA-N 0.000 claims description 4
SCIGNWNFAKREND-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]benzamide Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(NC(=O)C=3C=CC=CC=3)N=CC=2)=C1 SCIGNWNFAKREND-UHFFFAOYSA-N 0.000 claims description 4
CMUUIQIXHFCRMI-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-propyl-1,3-thiazol-5-yl]pyridin-2-yl]-2-phenylacetamide Chemical compound S1C(CCC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)CC1=CC=CC=C1 CMUUIQIXHFCRMI-UHFFFAOYSA-N 0.000 claims description 4
PMPPDEOJNIKDEQ-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-propyl-1,3-thiazol-5-yl]pyridin-2-yl]-3-phenylpropanamide Chemical compound S1C(CCC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)CCC1=CC=CC=C1 PMPPDEOJNIKDEQ-UHFFFAOYSA-N 0.000 claims description 4
OFRAIZACHYVYMG-UHFFFAOYSA-N n-[4-[4-(3-methylphenyl)-2-propyl-1,3-thiazol-5-yl]pyridin-2-yl]benzamide Chemical compound S1C(CCC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC(=O)C1=CC=CC=C1 OFRAIZACHYVYMG-UHFFFAOYSA-N 0.000 claims description 4
DZIKYKCJRCOVCN-UHFFFAOYSA-N n-[4-[4-(4-methoxyphenyl)-2-methyl-1,3-thiazol-5-yl]pyridin-2-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(NC(=O)C=3C=CC=CC=3)N=CC=2)SC(C)=N1 DZIKYKCJRCOVCN-UHFFFAOYSA-N 0.000 claims description 4
XMZJXLUVFMBXBC-UHFFFAOYSA-N n-[5-[2-(benzylamino)pyridin-4-yl]-4-(3,5-dimethylphenyl)-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C=2C=C(C)C=C(C)C=2)=C1C(C=1)=CC=NC=1NCC1=CC=CC=C1 XMZJXLUVFMBXBC-UHFFFAOYSA-N 0.000 claims description 4
XNUPFQFHYSTKFA-UHFFFAOYSA-N n-benzyl-4-[4-(3-methylphenyl)-2-propyl-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound S1C(CCC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NCC1=CC=CC=C1 XNUPFQFHYSTKFA-UHFFFAOYSA-N 0.000 claims description 4
GUCDKKHGPMSFAE-IBGZPJMESA-N 2-chloro-n-[4-(3-methylphenyl)-5-[2-[[(1s)-1-phenylethyl]amino]pyridin-4-yl]-1,3-thiazol-2-yl]pyridine-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=CC=1)=CC=1C(=C(N=1)C=2C=C(C)C=CC=2)SC=1NC(=O)C1=CC=CN=C1Cl GUCDKKHGPMSFAE-IBGZPJMESA-N 0.000 claims description 3
DWNSSAAMIFQWAN-FQEVSTJZSA-N 2-methoxy-n-[4-(3-methylphenyl)-5-[2-[[(1s)-1-phenylethyl]amino]pyridin-4-yl]-1,3-thiazol-2-yl]pyridine-3-carboxamide Chemical compound COC1=NC=CC=C1C(=O)NC1=NC(C=2C=C(C)C=CC=2)=C(C=2C=C(N[C@@H](C)C=3C=CC=CC=3)N=CC=2)S1 DWNSSAAMIFQWAN-FQEVSTJZSA-N 0.000 claims description 3
FRCZBTSAYXAPTH-HXUWFJFHSA-N 2-methyl-n-[4-(3-methylphenyl)-5-[2-[[(1r)-1-phenylethyl]amino]pyridin-4-yl]-1,3-thiazol-2-yl]pyridine-3-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=CC=1)=CC=1C(=C(N=1)C=2C=C(C)C=CC=2)SC=1NC(=O)C1=CC=CN=C1C FRCZBTSAYXAPTH-HXUWFJFHSA-N 0.000 claims description 3
FRCZBTSAYXAPTH-FQEVSTJZSA-N 2-methyl-n-[4-(3-methylphenyl)-5-[2-[[(1s)-1-phenylethyl]amino]pyridin-4-yl]-1,3-thiazol-2-yl]pyridine-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=CC=1)=CC=1C(=C(N=1)C=2C=C(C)C=CC=2)SC=1NC(=O)C1=CC=CN=C1C FRCZBTSAYXAPTH-FQEVSTJZSA-N 0.000 claims description 3
SRDLZWVKGPVOSM-FQEVSTJZSA-N 4-[2-(4-fluorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyridin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=CC=1)=CC=1C=1SC(C=2C=CC(F)=CC=2)=NC=1C1=CC=CC(C)=C1 SRDLZWVKGPVOSM-FQEVSTJZSA-N 0.000 claims description 3
ZEPFJMJGPOIVBS-HXUWFJFHSA-N 4-[2-butyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-n-[(1r)-1-phenylethyl]pyridin-2-amine Chemical compound C1([C@@H](C)NC=2N=CC=C(C=2)C2=C(N=C(S2)CCCC)C=2C=C(C)C=CC=2)=CC=CC=C1 ZEPFJMJGPOIVBS-HXUWFJFHSA-N 0.000 claims description 3
ZEPFJMJGPOIVBS-FQEVSTJZSA-N 4-[2-butyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyridin-2-amine Chemical compound C1([C@H](C)NC=2N=CC=C(C=2)C2=C(N=C(S2)CCCC)C=2C=C(C)C=CC=2)=CC=CC=C1 ZEPFJMJGPOIVBS-FQEVSTJZSA-N 0.000 claims description 3
XIVWBJMVECVXMH-GOSISDBHSA-N 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-n-[(1r)-1-phenylethyl]pyridin-2-amine Chemical compound C1([C@@H](C)NC=2N=CC=C(C=2)C2=C(N=C(S2)CC)C=2C=C(C)C=CC=2)=CC=CC=C1 XIVWBJMVECVXMH-GOSISDBHSA-N 0.000 claims description 3
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