JP2002302488A - 置換１，３−チアゾール化合物、その製造法および用途 - Google Patents

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Publication number

JP2002302488A

JP2002302488A JP2001100546A JP2001100546A JP2002302488A JP 2002302488 A JP2002302488 A JP 2002302488A JP 2001100546 A JP2001100546 A JP 2001100546A JP 2001100546 A JP2001100546 A JP 2001100546A JP 2002302488 A JP2002302488 A JP 2002302488A

Authority

JP

Japan

Prior art keywords

group

alkyl

atom

substituent

pyridyl

Prior art date

2000-03-30

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Withdrawn

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• -1 1,3-thiazole compound Chemical class 0.000 title claims abstract description 675
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• 125000001424 substituent group Chemical group 0.000 claims abstract description 288
• 150000001875 compounds Chemical class 0.000 claims abstract description 218
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 162
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 92
• 125000003118 aryl group Chemical group 0.000 claims abstract description 70
• 150000003839 salts Chemical class 0.000 claims abstract description 58
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 40
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 37
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• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 135
• 229910052799 carbon Inorganic materials 0.000 claims description 128
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 122
• 229910052717 sulfur Inorganic materials 0.000 claims description 118
• 125000000217 alkyl group Chemical group 0.000 claims description 114
• 125000000623 heterocyclic group Chemical group 0.000 claims description 108
• 125000005843 halogen group Chemical group 0.000 claims description 100
• 125000001931 aliphatic group Chemical group 0.000 claims description 78
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 74
• 229910052760 oxygen Inorganic materials 0.000 claims description 74
• 239000001301 oxygen Substances 0.000 claims description 74
• 150000001721 carbon Chemical group 0.000 claims description 71
• 125000003277 amino group Chemical group 0.000 claims description 69
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 67
• 239000011593 sulfur Substances 0.000 claims description 67
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• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 55
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 52
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 44
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 44
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• 125000004429 atom Chemical group 0.000 claims description 42
• 229910052801 chlorine Inorganic materials 0.000 claims description 41
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 36
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• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 30
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 29
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• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 26
• 125000002252 acyl group Chemical group 0.000 claims description 26
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 24
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• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
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• 150000002430 hydrocarbons Chemical class 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 17
• 125000004122 cyclic group Chemical group 0.000 claims description 17
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 229940124597 therapeutic agent Drugs 0.000 claims description 17
• 241000124008 Mammalia Species 0.000 claims description 16
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
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• 229930195733 hydrocarbon Natural products 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
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• 102000009346 Adenosine receptors Human genes 0.000 claims description 12
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
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• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
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• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 9
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• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
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• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 8
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• 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 7
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• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
• 208000036142 Viral infection Diseases 0.000 claims description 7
• 125000001118 alkylidene group Chemical group 0.000 claims description 7
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
• 206010008118 cerebral infarction Diseases 0.000 claims description 7
• 230000001684 chronic effect Effects 0.000 claims description 7
• 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims description 7
• 230000015271 coagulation Effects 0.000 claims description 7
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• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
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• 229940122696 MAP kinase inhibitor Drugs 0.000 claims description 6
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• SWVVZFVYYBURLS-UHFFFAOYSA-N [4-[2-acetamido-4-(3,5-dimethylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl] acetate Chemical compound S1C(NC(=O)C)=NC(C=2C=C(C)C=C(C)C=2)=C1C1=CC=NC(OC(C)=O)=C1 SWVVZFVYYBURLS-UHFFFAOYSA-N 0.000 claims description 6
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• KIYXQJKZXUCPGE-UHFFFAOYSA-N n-[4-(3,5-dimethylphenyl)-5-(2-oxo-1h-pyridin-4-yl)-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C=2C=C(C)C=C(C)C=2)=C1C1=CC=NC(O)=C1 KIYXQJKZXUCPGE-UHFFFAOYSA-N 0.000 claims description 6
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• 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 5
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• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
• PYSLGEQMEPZSNF-UHFFFAOYSA-N n-[4-[4-(3-chlorophenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]-2,2-dimethylpropanamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=CC(C2=C(N=C(S2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(Cl)C=CC=2)=C1 PYSLGEQMEPZSNF-UHFFFAOYSA-N 0.000 claims description 4
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• UPFRRHSKRDTERI-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)-2-ethyl-1,3-thiazol-5-yl]-n-cyclopentylpyridin-2-amine Chemical compound S1C(CC)=NC(C=2C=C(Cl)C=CC=2)=C1C(C=1)=CC=NC=1NC1CCCC1 UPFRRHSKRDTERI-UHFFFAOYSA-N 0.000 claims description 3
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• ZKGYOUSGGVYINQ-UHFFFAOYSA-N n-[4-(3,5-dimethylphenyl)-5-(2-methylpyridin-4-yl)-1,3-thiazol-2-yl]-6-methoxypyridine-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(=O)NC1=NC(C=2C=C(C)C=C(C)C=2)=C(C=2C=C(C)N=CC=2)S1 ZKGYOUSGGVYINQ-UHFFFAOYSA-N 0.000 claims description 3
• RKTVEQYGNFFPPQ-UHFFFAOYSA-N n-[4-(3,5-dimethylphenyl)-5-(2-methylpyridin-4-yl)-1,3-thiazol-2-yl]-6-methylpyridine-3-carboxamide Chemical compound CC1=CC(C)=CC(C2=C(SC(NC(=O)C=3C=NC(C)=CC=3)=N2)C=2C=C(C)N=CC=2)=C1 RKTVEQYGNFFPPQ-UHFFFAOYSA-N 0.000 claims description 3
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
• MZQLXNAHNXDOEL-UHFFFAOYSA-N 2-ethyl-5-(2-fluoropyridin-4-yl)-4-(3-methylphenyl)-1,3-thiazole Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C1=CC=NC(F)=C1 MZQLXNAHNXDOEL-UHFFFAOYSA-N 0.000 claims description 2
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• CPTCWHKUYHDMIZ-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(3-methylphenyl)-2-(4-methylsulfanylphenyl)-1,3-thiazole Chemical compound C1=CC(SC)=CC=C1C1=NC(C=2C=C(C)C=CC=2)=C(C=2C=C(F)N=CC=2)S1 CPTCWHKUYHDMIZ-UHFFFAOYSA-N 0.000 claims description 2
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• BRJDUUXGDCRANN-UHFFFAOYSA-N 6-chloro-n-[4-(3,5-dimethylphenyl)-5-(2-methylpyridin-4-yl)-1,3-thiazol-2-yl]pyridine-3-carboxamide Chemical compound CC1=CC(C)=CC(C2=C(SC(NC(=O)C=3C=NC(Cl)=CC=3)=N2)C=2C=C(C)N=CC=2)=C1 BRJDUUXGDCRANN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
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• FYENHNKKDWSFFG-UHFFFAOYSA-N n-[4-(3,5-dimethylphenyl)-5-(2-methylpyridin-4-yl)-1,3-thiazol-2-yl]pyridine-3-carboxamide Chemical compound CC1=CC(C)=CC(C2=C(SC(NC(=O)C=3C=NC=CC=3)=N2)C=2C=C(C)N=CC=2)=C1 FYENHNKKDWSFFG-UHFFFAOYSA-N 0.000 claims description 2
• FAGYPCZAQRPZJO-UHFFFAOYSA-N n-[4-(3-methylphenyl)-5-(2-methylpyridin-4-yl)-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C=2C=C(C)C=CC=2)=C1C1=CC=NC(C)=C1 FAGYPCZAQRPZJO-UHFFFAOYSA-N 0.000 claims description 2
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• QVEWLQUEUPMWAW-UHFFFAOYSA-N n-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)CC)=CC(C2=C(N=C(CC)S2)C=2C=C(C)C=CC=2)=C1 QVEWLQUEUPMWAW-UHFFFAOYSA-N 0.000 claims description 2
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