JP2002302488A5 - - Google Patents
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- JP2002302488A5 JP2002302488A5 JP2001100546A JP2001100546A JP2002302488A5 JP 2002302488 A5 JP2002302488 A5 JP 2002302488A5 JP 2001100546 A JP2001100546 A JP 2001100546A JP 2001100546 A JP2001100546 A JP 2001100546A JP 2002302488 A5 JP2002302488 A5 JP 2002302488A5
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- JP
- Japan
- Prior art keywords
- group
- alkyl
- atom
- carbonyl
- pyridyl
- Prior art date
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- 125000001424 substituent group Chemical group 0.000 description 62
- 125000000217 alkyl group Chemical group 0.000 description 48
- 229910052757 nitrogen Inorganic materials 0.000 description 40
- 125000005842 heteroatom Chemical group 0.000 description 33
- 229910052717 sulfur Inorganic materials 0.000 description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 description 26
- 125000000623 heterocyclic group Chemical group 0.000 description 25
- 125000005843 halogen group Chemical group 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 23
- -1 1,3-thiazole compound Chemical group 0.000 description 22
- 125000004430 oxygen atom Chemical group O* 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 125000004434 sulfur atom Chemical group 0.000 description 20
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 18
- 125000001931 aliphatic group Chemical group 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 14
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
- 239000011593 sulfur Chemical group 0.000 description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 229910052760 oxygen Chemical group 0.000 description 10
- 239000001301 oxygen Chemical group 0.000 description 10
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 8
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000005116 aryl carbamoyl group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 description 3
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 3
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 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 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 description 2
- 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 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 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 description 1
- ZKRZKOYFMQHGLU-UHFFFAOYSA-N 4-(3-methylphenyl)-5-(2-methylpyridin-4-yl)-1,3-thiazol-2-amine Chemical compound CC1=CC=CC(C2=C(SC(N)=N2)C=2C=C(C)N=CC=2)=C1 ZKRZKOYFMQHGLU-UHFFFAOYSA-N 0.000 description 1
- BMRNMQNHGZILHO-UHFFFAOYSA-N 4-(3-methylphenyl)-5-(2-methylpyridin-4-yl)-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(C)N=CC=2)S1 BMRNMQNHGZILHO-UHFFFAOYSA-N 0.000 description 1
- UCPSQOUWQZVUSL-UHFFFAOYSA-N 4-(3-methylphenyl)-5-(2-methylpyridin-4-yl)-2-(4-methylsulfinylphenyl)-1,3-thiazole Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)=O)C=2C=C(C)N=CC=2)=C1 UCPSQOUWQZVUSL-UHFFFAOYSA-N 0.000 description 1
- YGTCECUHLREAQV-UHFFFAOYSA-N 4-(3-methylphenyl)-5-(2-methylpyridin-4-yl)-2-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(C)N=CC=2)=C1 YGTCECUHLREAQV-UHFFFAOYSA-N 0.000 description 1
- VMHXXKMCQDJJSH-UHFFFAOYSA-N 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C1=CC=NC(N)=C1 VMHXXKMCQDJJSH-UHFFFAOYSA-N 0.000 description 1
- YKVIZYUAHDBQCM-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)-2-ethyl-1,3-thiazol-5-yl]-n-cyclohexylpyridin-2-amine Chemical compound S1C(CC)=NC(C=2C=C(Cl)C=CC=2)=C1C(C=1)=CC=NC=1NC1CCCCC1 YKVIZYUAHDBQCM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- DXLRQMZUECHTTN-UHFFFAOYSA-N 5-(2-fluoropyridin-4-yl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(F)N=CC=2)=C1 DXLRQMZUECHTTN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000026872 Addison Disease Diseases 0.000 description 1
- 102000009346 Adenosine receptors Human genes 0.000 description 1
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- 206010048962 Brain oedema Diseases 0.000 description 1
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 1
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
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- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 1
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- 102000004127 Cytokines Human genes 0.000 description 1
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- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
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- 125000001118 alkylidene group Chemical group 0.000 description 1
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- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
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- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
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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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- IZNYNBDTJRTLTA-UHFFFAOYSA-N n-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl]acetamide Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C1=CC=NC(NC(C)=O)=C1 IZNYNBDTJRTLTA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
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- YXZASXSSCXVALU-UHFFFAOYSA-N n-[4-[4-(3-chlorophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-yl]acetamide Chemical compound S1C(CC)=NC(C=2C=C(Cl)C=CC=2)=C1C1=CC=NC(NC(C)=O)=C1 YXZASXSSCXVALU-UHFFFAOYSA-N 0.000 description 1
- DGEORHVOUMRVML-UHFFFAOYSA-N n-[4-[4-(3-chlorophenyl)-2-ethyl-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(Cl)C=CC=2)=C1 DGEORHVOUMRVML-UHFFFAOYSA-N 0.000 description 1
- RXZBKSKENJRLKP-UHFFFAOYSA-N n-[4-[4-(3-chlorophenyl)-2-methyl-1,3-thiazol-5-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C2=C(N=C(C)S2)C=2C=C(Cl)C=CC=2)=C1 RXZBKSKENJRLKP-UHFFFAOYSA-N 0.000 description 1
- ASTRXNHXBQFXDO-UHFFFAOYSA-N n-[4-[4-(3-chlorophenyl)-2-methyl-1,3-thiazol-5-yl]pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)CC)=CC(C2=C(N=C(C)S2)C=2C=C(Cl)C=CC=2)=C1 ASTRXNHXBQFXDO-UHFFFAOYSA-N 0.000 description 1
- WURLIRVPQHPYNB-UHFFFAOYSA-N n-[4-[4-(3-chlorophenyl)-2-propyl-1,3-thiazol-5-yl]pyridin-2-yl]acetamide Chemical compound S1C(CCC)=NC(C=2C=C(Cl)C=CC=2)=C1C1=CC=NC(NC(C)=O)=C1 WURLIRVPQHPYNB-UHFFFAOYSA-N 0.000 description 1
- ARNBJHOVHNFWFN-UHFFFAOYSA-N n-[4-[4-(3-chlorophenyl)-2-propyl-1,3-thiazol-5-yl]pyridin-2-yl]propanamide Chemical compound S1C(CCC)=NC(C=2C=C(Cl)C=CC=2)=C1C1=CC=NC(NC(=O)CC)=C1 ARNBJHOVHNFWFN-UHFFFAOYSA-N 0.000 description 1
- YJYKOHXNNCEGQK-UHFFFAOYSA-N n-cyclohexyl-4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC1CCCCC1 YJYKOHXNNCEGQK-UHFFFAOYSA-N 0.000 description 1
- CIROQZHOCKAZOI-UHFFFAOYSA-N n-cyclohexyl-4-[4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(NC3CCCCC3)N=CC=2)=C1 CIROQZHOCKAZOI-UHFFFAOYSA-N 0.000 description 1
- KRJISXKXXCKOEU-UHFFFAOYSA-N n-cyclopentyl-4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound S1C(CC)=NC(C=2C=C(C)C=CC=2)=C1C(C=1)=CC=NC=1NC1CCCC1 KRJISXKXXCKOEU-UHFFFAOYSA-N 0.000 description 1
- FYHJSQPBUNNCHZ-UHFFFAOYSA-N n-cyclopentyl-4-[4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound CC1=CC=CC(C2=C(SC(=N2)C=2C=CC(=CC=2)S(C)(=O)=O)C=2C=C(NC3CCCC3)N=CC=2)=C1 FYHJSQPBUNNCHZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001100546A JP2002302488A (ja) | 2000-03-30 | 2001-03-30 | 置換１，３−チアゾール化合物、その製造法および用途 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000097876 | 2000-03-30 | ||
| JP2000-97876 | 2001-02-02 | ||
| JP2001-27571 | 2001-02-02 | ||
| JP2001027571 | 2001-02-02 | ||
| JP2001100546A JP2002302488A (ja) | 2000-03-30 | 2001-03-30 | 置換１，３−チアゾール化合物、その製造法および用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002302488A JP2002302488A (ja) | 2002-10-18 |
| JP2002302488A5 true JP2002302488A5 (https=) | 2008-03-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2001100546A Withdrawn JP2002302488A (ja) | 2000-03-30 | 2001-03-30 | 置換１，３−チアゾール化合物、その製造法および用途 |
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| JP (1) | JP2002302488A (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4758337B2 (ja) * | 2003-03-31 | 2011-08-24 | 株式会社アールテック・ウエノ | 血管透過性亢進疾患を治療する方法 |
| TWI336697B (en) * | 2003-09-19 | 2011-02-01 | Solvay Pharm Bv | Thiazole derivatives as cannabinoid receptor modulators |
| CA2551611C (en) * | 2003-12-26 | 2013-06-25 | Kyowa Kirin Co., Ltd. | Thiazole derivatives for treating or preventing parkinson's disease |
| BRPI0515519A (pt) * | 2004-09-22 | 2008-07-29 | H. Lundbeck & Co A/S | composto, e, uso do mesmo |
| AU2006217742A1 (en) * | 2005-02-25 | 2006-08-31 | Kudos Pharmaceuticals Limited | Hydrazinomethyl, HYDR zonomethyl and 5-membered heterocylic compounds which act as MTOR inhibitors and their use as anti cancer agents |
| WO2006137527A1 (ja) * | 2005-06-23 | 2006-12-28 | Kyowa Hakko Kogyo Co., Ltd. | チアゾール誘導体 |
| DK1921077T3 (en) * | 2005-08-02 | 2017-10-23 | Kyowa Hakko Kirin Co Ltd | Means for treating and / or preventing sleep disorders |
| CA2639910A1 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| CN101535303B (zh) * | 2006-08-15 | 2012-07-18 | 诺瓦提斯公司 | 适合用于治疗与升高的脂质水平有关的疾病的杂环化合物 |
| UY32730A (es) * | 2009-06-26 | 2011-01-31 | Novartis Ag | Inhibidores de cyp17 |
-
2001
- 2001-03-30 JP JP2001100546A patent/JP2002302488A/ja not_active Withdrawn
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