JP2009513563A5 - - Google Patents
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- JP2009513563A5 JP2009513563A5 JP2008525998A JP2008525998A JP2009513563A5 JP 2009513563 A5 JP2009513563 A5 JP 2009513563A5 JP 2008525998 A JP2008525998 A JP 2008525998A JP 2008525998 A JP2008525998 A JP 2008525998A JP 2009513563 A5 JP2009513563 A5 JP 2009513563A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- methyl
- methylthiazole
- amide
- thiazole
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 claims 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 201000010099 disease Diseases 0.000 claims 19
- -1 -R 6 -OR 7 Chemical group 0.000 claims 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 16
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims 12
- 108010028096 Stearoyl-CoA Desaturase Proteins 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 12
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims 12
- 125000005418 aryl aryl group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 8
- 125000003367 polycyclic group Chemical group 0.000 claims 8
- 230000027455 binding Effects 0.000 claims 7
- 230000002401 inhibitory effect Effects 0.000 claims 6
- 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 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 230000001404 mediated Effects 0.000 claims 5
- 206010012601 Diabetes mellitus Diseases 0.000 claims 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrugs Drugs 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- 125000004952 trihaloalkoxy group Chemical group 0.000 claims 4
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 4
- DTHNMHAUYICORS-KTKZVXAJSA-N 107444-51-9 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 3
- 102000004877 Insulin Human genes 0.000 claims 3
- 108090001061 Insulin Proteins 0.000 claims 3
- 206010022489 Insulin resistance Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- GGNIKGLUPSHSBV-UHFFFAOYSA-N 1,3-thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 claims 2
- 206010058108 Dyslipidaemia Diseases 0.000 claims 2
- 208000004930 Fatty Liver Diseases 0.000 claims 2
- 102100003818 GCG Human genes 0.000 claims 2
- 101710042131 GCG Proteins 0.000 claims 2
- 101700071595 GRZ1 Proteins 0.000 claims 2
- 206010019708 Hepatic steatosis Diseases 0.000 claims 2
- 206010061227 Lipid metabolism disease Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 206010053219 Non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 208000006641 Skin Disease Diseases 0.000 claims 2
- 208000001072 Type 2 Diabetes Mellitus Diseases 0.000 claims 2
- 101700078733 ZGLP1 Proteins 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 2
- VLIQUKXIEPYSKY-UHFFFAOYSA-N 2-(adamantane-1-carbonylamino)-4-methyl-N-phenyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)C23CC4CC(CC(C4)C2)C3)SC=1C(=O)NC1=CC=CC=C1 VLIQUKXIEPYSKY-UHFFFAOYSA-N 0.000 claims 1
- SPDBHWFZMQBCCK-UHFFFAOYSA-N 2-(adamantane-1-carbonylamino)-N-(3-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=CC(NC(=O)C2=C(N=C(NC(=O)C34CC5CC(CC(C5)C3)C4)S2)C)=C1 SPDBHWFZMQBCCK-UHFFFAOYSA-N 0.000 claims 1
- HKFDNWAYIYAEPK-UHFFFAOYSA-N 2-(adamantane-1-carbonylamino)-N-(4-bromophenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)C23CC4CC(CC(C4)C2)C3)SC=1C(=O)NC1=CC=C(Br)C=C1 HKFDNWAYIYAEPK-UHFFFAOYSA-N 0.000 claims 1
- GGZFXQNWOMNLMF-UHFFFAOYSA-N 2-(adamantane-1-carbonylamino)-N-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)C23CC4CC(CC(C4)C2)C3)S1 GGZFXQNWOMNLMF-UHFFFAOYSA-N 0.000 claims 1
- YFSYYDMKPUGXJJ-UHFFFAOYSA-N 2-(adamantane-1-carbonylamino)-N-benzyl-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)C23CC4CC(CC(C4)C2)C3)SC=1C(=O)NCC1=CC=CC=C1 YFSYYDMKPUGXJJ-UHFFFAOYSA-N 0.000 claims 1
- IDAICGYHWIDEND-UHFFFAOYSA-N 2-(adamantane-1-carbonylamino)-N-cyclohexyl-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(NC(=O)C23CC4CC(CC(C4)C2)C3)SC=1C(=O)NC1CCCCC1 IDAICGYHWIDEND-UHFFFAOYSA-N 0.000 claims 1
- KLRMOJAEJFTUKN-UHFFFAOYSA-N 2-(cyclohexanecarbonylamino)-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=C3OCCOC3=CC=2)=C(C)N=C1NC(=O)C1CCCCC1 KLRMOJAEJFTUKN-UHFFFAOYSA-N 0.000 claims 1
- FGHTZCGRZARSTI-UHFFFAOYSA-N 2-(cyclohexanecarbonylamino)-N-(2,3-dihydro-1H-inden-5-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=C3CCCC3=CC=2)=C(C)N=C1NC(=O)C1CCCCC1 FGHTZCGRZARSTI-UHFFFAOYSA-N 0.000 claims 1
- WIVAFIPIRYDUPG-UHFFFAOYSA-N 2-(cyclohexanecarbonylamino)-N-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)C2CCCCC2)S1 WIVAFIPIRYDUPG-UHFFFAOYSA-N 0.000 claims 1
- VADCVJMOSZEHJD-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)-4-methyl-N-(2-methylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC=CC=2)C)=C(C)N=C1NC(=O)C1CC1 VADCVJMOSZEHJD-UHFFFAOYSA-N 0.000 claims 1
- CKJSARLXLUFZSU-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)-4-methyl-N-phenyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1CC1 CKJSARLXLUFZSU-UHFFFAOYSA-N 0.000 claims 1
- NVTSHLRAUHCNOQ-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)-N-(2,3-dihydro-1H-inden-5-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=C3CCCC3=CC=2)=C(C)N=C1NC(=O)C1CC1 NVTSHLRAUHCNOQ-UHFFFAOYSA-N 0.000 claims 1
- GAPNCDYWAMKXRL-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)-N-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)C2CC2)S1 GAPNCDYWAMKXRL-UHFFFAOYSA-N 0.000 claims 1
- ODSGGDGRAYREDJ-UHFFFAOYSA-N 2-(furan-2-carbonylamino)-4-methyl-N-(2-methylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC=CC=2)C)=C(C)N=C1NC(=O)C1=CC=CO1 ODSGGDGRAYREDJ-UHFFFAOYSA-N 0.000 claims 1
- ACJDFTFXUVWTPP-UHFFFAOYSA-N 2-(furan-2-carbonylamino)-4-methyl-N-phenyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=CO1 ACJDFTFXUVWTPP-UHFFFAOYSA-N 0.000 claims 1
- VDNQGOYRMZFXMJ-UHFFFAOYSA-N 2-(furan-2-carbonylamino)-N-(3-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=CC(NC(=O)C2=C(N=C(NC(=O)C=3OC=CC=3)S2)C)=C1 VDNQGOYRMZFXMJ-UHFFFAOYSA-N 0.000 claims 1
- LJOPCFKGLLSAEH-UHFFFAOYSA-N 2-(furan-2-carbonylamino)-N-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)C=2OC=CC=2)S1 LJOPCFKGLLSAEH-UHFFFAOYSA-N 0.000 claims 1
- XPRILLPYKLYJEF-UHFFFAOYSA-N 2-[(2,6-difluorobenzoyl)amino]-N,N,4-trimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)N(C)C)SC(NC(=O)C=2C(=CC=CC=2F)F)=N1 XPRILLPYKLYJEF-UHFFFAOYSA-N 0.000 claims 1
- WAEUCPJLEKTDNQ-UHFFFAOYSA-N 2-[(2-fluorobenzoyl)amino]-4-methyl-N-(2-methylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC=CC=2)C)=C(C)N=C1NC(=O)C1=CC=CC=C1F WAEUCPJLEKTDNQ-UHFFFAOYSA-N 0.000 claims 1
- LGAGLGKDTZLBFL-UHFFFAOYSA-N 2-[(2-fluorobenzoyl)amino]-N-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)C=2C(=CC=CC=2)F)S1 LGAGLGKDTZLBFL-UHFFFAOYSA-N 0.000 claims 1
- JUPUHXSAEJUNCO-UHFFFAOYSA-N 2-[(3,4-dimethoxybenzoyl)amino]-N,N,4-trimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=NC(C)=C(C(=O)N(C)C)S1 JUPUHXSAEJUNCO-UHFFFAOYSA-N 0.000 claims 1
- GXRWTEXBAFYUTG-UHFFFAOYSA-N 2-[(3-chlorobenzoyl)amino]-4-methyl-N-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=NC=CC=2)=C(C)N=C1NC(=O)C1=CC=CC(Cl)=C1 GXRWTEXBAFYUTG-UHFFFAOYSA-N 0.000 claims 1
- QRBLCSFOPHGZTG-UHFFFAOYSA-N 2-[(3-chlorobenzoyl)amino]-N-cyclohexyl-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC2CCCCC2)=C(C)N=C1NC(=O)C1=CC=CC(Cl)=C1 QRBLCSFOPHGZTG-UHFFFAOYSA-N 0.000 claims 1
- JIVOUFQCAKZGIZ-UHFFFAOYSA-N 2-[(3-fluorobenzoyl)amino]-4-methyl-N-phenyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=CC(F)=C1 JIVOUFQCAKZGIZ-UHFFFAOYSA-N 0.000 claims 1
- UGPLMWZNVWBFMN-UHFFFAOYSA-N 2-[(3-fluorobenzoyl)amino]-N-(3-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=CC(NC(=O)C2=C(N=C(NC(=O)C=3C=C(F)C=CC=3)S2)C)=C1 UGPLMWZNVWBFMN-UHFFFAOYSA-N 0.000 claims 1
- HWPUVTPZRTVOCS-UHFFFAOYSA-N 2-[(3-methoxybenzoyl)amino]-N-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)C=2C=C(OC)C=CC=2)S1 HWPUVTPZRTVOCS-UHFFFAOYSA-N 0.000 claims 1
- ACCZUFUAAWJOFF-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-methyl-N-(2-methylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC=CC=2)C)=C(C)N=C1NC(=O)C1=CC=C(Br)C=C1 ACCZUFUAAWJOFF-UHFFFAOYSA-N 0.000 claims 1
- NYNGPHCKHRMRTO-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-methyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NN=C1NC(=O)C1=C(C)N=C(NC(=O)C=2C=CC(Br)=CC=2)S1 NYNGPHCKHRMRTO-UHFFFAOYSA-N 0.000 claims 1
- MZDNHDMQDBCUSC-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-methyl-N-phenyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=C(Br)C=C1 MZDNHDMQDBCUSC-UHFFFAOYSA-N 0.000 claims 1
- AGPOHGLIDBVZFV-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=C3OCCOC3=CC=2)=C(C)N=C1NC(=O)C1=CC=C(Br)C=C1 AGPOHGLIDBVZFV-UHFFFAOYSA-N 0.000 claims 1
- BPKOSGSKZHLOGF-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-N-(2,3-dihydro-1H-inden-5-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=C3CCCC3=CC=2)=C(C)N=C1NC(=O)C1=CC=C(Br)C=C1 BPKOSGSKZHLOGF-UHFFFAOYSA-N 0.000 claims 1
- SJWWHZUQPNCUFF-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-N-(2-chlorophenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC=CC=2)Cl)=C(C)N=C1NC(=O)C1=CC=C(Br)C=C1 SJWWHZUQPNCUFF-UHFFFAOYSA-N 0.000 claims 1
- YAYCOAKURJYPMR-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-N-(3-chlorophenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=C(Cl)C=CC=2)=C(C)N=C1NC(=O)C1=CC=C(Br)C=C1 YAYCOAKURJYPMR-UHFFFAOYSA-N 0.000 claims 1
- SXPKOFURMHQDAA-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-N-(3-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=CC(NC(=O)C2=C(N=C(NC(=O)C=3C=CC(Br)=CC=3)S2)C)=C1 SXPKOFURMHQDAA-UHFFFAOYSA-N 0.000 claims 1
- UCNCQVUBGAYCQD-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-N-(4-chlorophenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=CC(Cl)=CC=2)=C(C)N=C1NC(=O)C1=CC=C(Br)C=C1 UCNCQVUBGAYCQD-UHFFFAOYSA-N 0.000 claims 1
- RJSHOQINULMKFZ-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-N-cyclohexyl-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC2CCCCC2)=C(C)N=C1NC(=O)C1=CC=C(Cl)C=C1 RJSHOQINULMKFZ-UHFFFAOYSA-N 0.000 claims 1
- ZFUNSSFJDKYBGQ-UHFFFAOYSA-N 2-[(4-fluorobenzoyl)amino]-4-methyl-N-(2-methylphenyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC=CC=2)C)=C(C)N=C1NC(=O)C1=CC=C(F)C=C1 ZFUNSSFJDKYBGQ-UHFFFAOYSA-N 0.000 claims 1
- HKDQLLSSZBTEHN-UHFFFAOYSA-N 2-[(4-fluorobenzoyl)amino]-4-methyl-N-phenyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=C(F)C=C1 HKDQLLSSZBTEHN-UHFFFAOYSA-N 0.000 claims 1
- VKIUTSMYUNUFBY-UHFFFAOYSA-N 2-[(4-fluorobenzoyl)amino]-N-(3-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=CC(NC(=O)C2=C(N=C(NC(=O)C=3C=CC(F)=CC=3)S2)C)=C1 VKIUTSMYUNUFBY-UHFFFAOYSA-N 0.000 claims 1
- IGXFSZXDMNSWLF-UHFFFAOYSA-N 2-[(4-fluorobenzoyl)amino]-N-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(C)N=C(NC(=O)C=2C=CC(F)=CC=2)S1 IGXFSZXDMNSWLF-UHFFFAOYSA-N 0.000 claims 1
- NXLIWBXLXGCDTL-UHFFFAOYSA-N 2-[(4-methoxybenzoyl)amino]-4-methyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC(C)=C(C(=O)NC=2SC(C)=NN=2)S1 NXLIWBXLXGCDTL-UHFFFAOYSA-N 0.000 claims 1
- CHMHSZJFHVIZAS-UHFFFAOYSA-N 2-[(4-methoxybenzoyl)amino]-4-methyl-N-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC(C)=C(C(=O)NC=2C=NC=CC=2)S1 CHMHSZJFHVIZAS-UHFFFAOYSA-N 0.000 claims 1
- UGJUYPFNXBFDBO-UHFFFAOYSA-N 2-[(4-methoxybenzoyl)amino]-N-(3-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC(C)=C(C(=O)NC=2C=C(OC)C=CC=2)S1 UGJUYPFNXBFDBO-UHFFFAOYSA-N 0.000 claims 1
- JKWYMYLDQJWLQW-UHFFFAOYSA-N 2-[(4-tert-butylbenzoyl)amino]-4-methyl-N-phenyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 JKWYMYLDQJWLQW-UHFFFAOYSA-N 0.000 claims 1
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- UMYBKNRMIGIODC-UHFFFAOYSA-N N-benzyl-4-methyl-2-[[2-(trifluoromethyl)benzoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=CC=C1C(F)(F)F UMYBKNRMIGIODC-UHFFFAOYSA-N 0.000 claims 1
- KLJXPGPPZGRRQJ-UHFFFAOYSA-N N-benzyl-4-methyl-2-[[3-(trifluoromethoxy)benzoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=CC(OC(F)(F)F)=C1 KLJXPGPPZGRRQJ-UHFFFAOYSA-N 0.000 claims 1
- BWBDKZKVUKSMBT-UHFFFAOYSA-N N-benzyl-4-methyl-2-[[3-(trifluoromethyl)benzoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BWBDKZKVUKSMBT-UHFFFAOYSA-N 0.000 claims 1
- VYXBXLDDXONFGY-UHFFFAOYSA-N N-benzyl-4-methyl-2-[[4-(2-oxopyridin-1-yl)benzoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCC=2C=CC=CC=2)=C(C)N=C1NC(=O)C(C=C1)=CC=C1N1C=CC=CC1=O VYXBXLDDXONFGY-UHFFFAOYSA-N 0.000 claims 1
- QQAGAKZSFRNLJT-UHFFFAOYSA-N N-benzyl-4-methyl-2-[[4-(2H-tetrazol-5-yl)benzoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCC=2C=CC=CC=2)=C(C)N=C1NC(=O)C(C=C1)=CC=C1C=1N=NNN=1 QQAGAKZSFRNLJT-UHFFFAOYSA-N 0.000 claims 1
- ACYDLNLJTFEXPO-UHFFFAOYSA-N N-benzyl-4-methyl-2-[[4-(trifluoromethoxy)benzoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 ACYDLNLJTFEXPO-UHFFFAOYSA-N 0.000 claims 1
- AJUWIRBQPBCTOM-UHFFFAOYSA-N N-benzyl-4-methyl-2-[[4-(trifluoromethyl)benzoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCC=2C=CC=CC=2)=C(C)N=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 AJUWIRBQPBCTOM-UHFFFAOYSA-N 0.000 claims 1
- NZCIQXYBXKGMNX-UHFFFAOYSA-N N-cyclohexyl-2-(cyclopropanecarbonylamino)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC2CCCCC2)=C(C)N=C1NC(=O)C1CC1 NZCIQXYBXKGMNX-UHFFFAOYSA-N 0.000 claims 1
- RRJYRLPUJGQLID-UHFFFAOYSA-N N-cyclohexyl-4-methyl-2-(propanoylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NC(=O)CC)=NC(C)=C1C(=O)NC1CCCCC1 RRJYRLPUJGQLID-UHFFFAOYSA-N 0.000 claims 1
- WPFDWGOOONLNAT-UHFFFAOYSA-N N-cyclohexyl-4-methyl-2-[(3,4,5-trimethoxybenzoyl)amino]-1,3-thiazole-5-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2SC(=C(C)N=2)C(=O)NC2CCCCC2)=C1 WPFDWGOOONLNAT-UHFFFAOYSA-N 0.000 claims 1
- QUCAQBJMPOINFV-UHFFFAOYSA-N N-cyclohexyl-4-methyl-2-[(3-methylbenzoyl)amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC2CCCCC2)=C(C)N=C1NC(=O)C1=CC=CC(C)=C1 QUCAQBJMPOINFV-UHFFFAOYSA-N 0.000 claims 1
- YBIOAXJHNHVCDZ-UHFFFAOYSA-N N-cyclohexyl-4-methyl-2-[(4-methylbenzoyl)amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC2CCCCC2)=C(C)N=C1NC(=O)C1=CC=C(C)C=C1 YBIOAXJHNHVCDZ-UHFFFAOYSA-N 0.000 claims 1
- RNDCRLKFJASAKU-OUKQBFOZSA-N N-cyclohexyl-4-methyl-2-[[(E)-3-phenylprop-2-enoyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC2CCCCC2)=C(C)N=C1NC(=O)\C=C\C1=CC=CC=C1 RNDCRLKFJASAKU-OUKQBFOZSA-N 0.000 claims 1
- 206010033307 Overweight Diseases 0.000 claims 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 1
- 102000018692 Sulfonylurea Receptors Human genes 0.000 claims 1
- 101700012936 Sur Proteins 0.000 claims 1
- HGMSJMJPXGGEBP-UHFFFAOYSA-N [4-[3-(4-ethylphenyl)butyl]phenyl]-trimethylazanium Chemical compound C1=CC(CC)=CC=C1C(C)CCC1=CC=C([N+](C)(C)C)C=C1 HGMSJMJPXGGEBP-UHFFFAOYSA-N 0.000 claims 1
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 1
- 229940058933 biguanide antimalarials Drugs 0.000 claims 1
- 229940090145 biguanide blood glucose lower drugs Drugs 0.000 claims 1
- 150000004283 biguanides Chemical class 0.000 claims 1
- 229940090127 blood glucose lowering Alpha glucosidase inhibitors Drugs 0.000 claims 1
- 230000003247 decreasing Effects 0.000 claims 1
- 230000001419 dependent Effects 0.000 claims 1
- 201000004624 dermatitis Diseases 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 231100001003 eczema Toxicity 0.000 claims 1
- JNWSTEWIXVHYNR-UHFFFAOYSA-N ethyl 2-[(2-benzamido-4-methyl-1,3-thiazole-5-carbonyl)amino]acetate Chemical compound CC1=C(C(=O)NCC(=O)OCC)SC(NC(=O)C=2C=CC=CC=2)=N1 JNWSTEWIXVHYNR-UHFFFAOYSA-N 0.000 claims 1
- IHFWDNOFDRSICE-UHFFFAOYSA-N ethyl 2-[[2-[(2-fluorobenzoyl)amino]-4-methyl-1,3-thiazole-5-carbonyl]amino]acetate Chemical compound CC1=C(C(=O)NCC(=O)OCC)SC(NC(=O)C=2C(=CC=CC=2)F)=N1 IHFWDNOFDRSICE-UHFFFAOYSA-N 0.000 claims 1
- DVPBEXPNYNWGRK-UHFFFAOYSA-N ethyl 2-[[2-[(3-fluorobenzoyl)amino]-4-methyl-1,3-thiazole-5-carbonyl]amino]acetate Chemical compound CC1=C(C(=O)NCC(=O)OCC)SC(NC(=O)C=2C=C(F)C=CC=2)=N1 DVPBEXPNYNWGRK-UHFFFAOYSA-N 0.000 claims 1
- KVUMEZRFGIOHOQ-UHFFFAOYSA-N ethyl 2-[[2-[(3-methoxybenzoyl)amino]-4-methyl-1,3-thiazole-5-carbonyl]amino]acetate Chemical compound CC1=C(C(=O)NCC(=O)OCC)SC(NC(=O)C=2C=C(OC)C=CC=2)=N1 KVUMEZRFGIOHOQ-UHFFFAOYSA-N 0.000 claims 1
- FSNMMMLVOKEPKN-UHFFFAOYSA-N ethyl 2-[[2-[(4-fluorobenzoyl)amino]-4-methyl-1,3-thiazole-5-carbonyl]amino]acetate Chemical compound CC1=C(C(=O)NCC(=O)OCC)SC(NC(=O)C=2C=CC(F)=CC=2)=N1 FSNMMMLVOKEPKN-UHFFFAOYSA-N 0.000 claims 1
- DXHAMFRIDXFDMH-UHFFFAOYSA-N ethyl 2-[[2-[(4-methoxybenzoyl)amino]-4-methyl-1,3-thiazole-5-carbonyl]amino]acetate Chemical compound CC1=C(C(=O)NCC(=O)OCC)SC(NC(=O)C=2C=CC(OC)=CC=2)=N1 DXHAMFRIDXFDMH-UHFFFAOYSA-N 0.000 claims 1
- RYNURAKYSLCLAP-UHFFFAOYSA-N ethyl 2-[[4-methyl-2-(3-phenylprop-2-enoylamino)-1,3-thiazole-5-carbonyl]amino]acetate Chemical compound CC1=C(C(=O)NCC(=O)OCC)SC(NC(=O)C=CC=2C=CC=CC=2)=N1 RYNURAKYSLCLAP-UHFFFAOYSA-N 0.000 claims 1
- HUCZWZCBANVUJV-UHFFFAOYSA-N ethyl 2-[[4-methyl-2-[(3,4,5-trimethoxybenzoyl)amino]-1,3-thiazole-5-carbonyl]amino]acetate Chemical compound CC1=C(C(=O)NCC(=O)OCC)SC(NC(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=N1 HUCZWZCBANVUJV-UHFFFAOYSA-N 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 201000001431 hyperuricemia Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000003914 insulin secretion Effects 0.000 claims 1
- 229940039781 leptin Drugs 0.000 claims 1
- 230000003278 mimic Effects 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000020825 overweight Nutrition 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 201000004681 psoriasis Diseases 0.000 claims 1
- 230000036573 scar formation Effects 0.000 claims 1
- 230000000580 secretagogue Effects 0.000 claims 1
- 231100000489 sensitizer Toxicity 0.000 claims 1
- 239000004059 squalene synthase inhibitor Substances 0.000 claims 1
- 230000004936 stimulating Effects 0.000 claims 1
- 201000010874 syndrome Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 201000005665 thrombophilia Diseases 0.000 claims 1
- 230000004580 weight loss Effects 0.000 claims 1
Claims (24)
- ヒトのステアロイル−CoAデサチュラーゼ(hSCD)活性を阻害するための組成物であって、式(I):
Wは、−O−、−OC(O)−、−OC(O)N(R5)−、−OS(O)2N(R5)−、−C(O)−、−C(O)O−、−C(O)N(R5)−、−N(R5)−、−N(R5)C(O)−、−N(R5)C(O)O−、−N(R5)C(O)N(R5)−、−N(R5)S(O)2−、−S(O)t−(ここで、tは0、1もしくは2である)または−S(O)2N(R5)−から選択され;
Vは、−C(O)−、−C(O)N(R5)−、−C(O)O−、−S(O)t−(ここで、tは1もしくは2である)または直接結合から選択され;
R1は、アルキル、アルケニル、−R6−OR7、ヒドロキシアルケニル、シクロアルキル、シクロアルキルアルキル、アリール、アラルキル、アラルケニル、ヘテロシクリル、ヘテロシクリルアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群から選択されるか;
あるいは、R1は2〜4個の環を有する多環構造体であり、該環は、シクロアルキル、ヘテロシクリル、アリールおよびヘテロアリールからなる群から独立に選択され、かつ、該環のいくつかまたはすべては互いに縮合していてもよく;
R2は、アルキル、アルケニル、−R6−OR7、ヒドロキシアルケニル、シクロアルキル、シクロアルキルアルキル、アリール、アラルキル、アラルケニル、ヘテロシクリル、ヘテロシクリルアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群から選択されるか;
あるいは、R2は2〜4個の環を有する多環構造体であり、該環は、シクロアルキル、ヘテロシクリル、アリールおよびヘテロアリールからなる群から独立に選択され、かつ、該環のいくつかまたはすべては互いに縮合していてもよく;
R3は、水素、アルキル、アルケニル、ヒドロキシアルキル、ヒドロキシアルケニル、アルコキシアルキル、シクロアルキル、シクロアルキルアルキル、ヘテロシクリル、アリール、アラルキル、ヘテロアリール、フルオロ、クロロ、ブロモ、トリハロアルキル、トリハロアルコキシ、シアノ、ニトロ、−OR4、−OC(O)R2、−OC(O)N(R4)(R5)、−OS(O)2N(R4)(R5)、−S(O)tR2(ここで、tは0、1もしくは2である)、−S(O)tN(R4)(R5)(ここで、tは1もしくは2である)、−C(O)R2、−C(O)OR2、−C(O)N(R4)(R5)、−N(R4)(R5)、−N(R5)C(O)R5、−N(R5)C(O)OR5、−N(R5)C(O)N(R4)(R5)または−N(R5)S(O)2R2から選択され;
各R4およびR5は、−R6−N(R7)2、−R6−OR7、−R6−C(O)OR7、水素、アルキル、シクロアルキルアルキルおよびアラルキルからなる群から独立に選択され;
各R6は直鎖または分岐鎖のアルキレン鎖であり;
各R7は水素、アルキル、アリールまたはアラルキルである、組成物。 - 哺乳動物のステアロイル−CoAデサチュラーゼ(SCD)によって媒介される疾患または状態を治療するための組成物であって、治療有効量の式(I):
Wは、−O−、−OC(O)−、−OC(O)N(R5)−、−OS(O)2N(R5)−、−C(O)−、−C(O)O−、−C(O)N(R5)−、−N(R5)−、−N(R5)C(O)−、−N(R5)C(O)O−、−N(R5)C(O)N(R5)−、−N(R5)S(O)2−、−S(O)t−(ここで、tは0、1もしくは2である)または−S(O)2N(R5)−から選択され;
Vは、−C(O)−、−C(O)N(R5)−、−C(O)O−、−S(O)t−(ここで、tは1もしくは2である)または直接結合から選択され;
R1は、アルキル、アルケニル、−R6−OR7、ヒドロキシアルケニル、シクロアルキル、シクロアルキルアルキル、アリール、アラルキル、アラルケニル、ヘテロシクリル、ヘテロシクリルアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群から選択されるか;
あるいは、R1は2〜4個の環を有する多環構造体であり、該環は、シクロアルキル、ヘテロシクリル、アリールおよびヘテロアリールからなる群から独立に選択され、かつ、該環のいくつかまたはすべては互いに縮合していてもよく;
R2は、アルキル、アルケニル、−R6−OR7、ヒドロキシアルケニル、シクロアルキル、シクロアルキルアルキル、アリール、アラルキル、アラルケニル、ヘテロシクリル、ヘテロシクリルアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群から選択されるか;
あるいは、R2は2〜4個の環を有する多環構造体であり、該環は、シクロアルキル、ヘテロシクリル、アリールおよびヘテロアリールからなる群から独立に選択され、かつ、該環のいくつかまたはすべては互いに縮合していてもよく;
R3は、水素、アルキル、アルケニル、ヒドロキシアルキル、ヒドロキシアルケニル、アルコキシアルキル、シクロアルキル、シクロアルキルアルキル、ヘテロシクリル、アリール、アラルキル、ヘテロアリール、フルオロ、クロロ、ブロモ、トリハロアルキル、トリハロアルコキシ、シアノ、ニトロ、−OR4、−OC(O)R2、−OC(O)N(R4)(R5)、−OS(O)2N(R4)(R5)、−S(O)tR2(ここで、tは0、1もしくは2である)、−S(O)tN(R4)(R5)(ここで、tは1もしくは2である)、−C(O)R2、−C(O)OR2、−C(O)N(R4)(R5)、−N(R4)(R5)、−N(R5)C(O)R5、−N(R5)C(O)OR5、−N(R5)C(O)N(R4)(R5)または−N(R5)S(O)2R2から選択され;
各R4およびR5は、−R6−N(R7)2、−R6−OR7、−R6−C(O)OR7、水素、アルキル、シクロアルキルアルキルおよびアラルキルからなる群から独立に選択され;
各R6は直鎖または分岐鎖のアルキレン鎖であり;
各R7は水素、アルキル、アリールまたはアラルキルである、組成物。 - 前記哺乳動物がヒトである、請求項2に記載の組成物。
- 前記疾患または状態が、2型糖尿病、耐糖能異常、インスリン抵抗性、肥満、脂肪肝、非アルコール性脂肪性肝炎、異脂肪血症およびメタボリックシンドローム、ならびにこれらの任意の組合せからなる群から選択される、請求項2に記載の組成物。
- 前記疾患または状態が2型糖尿病である、請求項4に記載の組成物。
- 前記疾患または状態が肥満である、請求項4に記載の組成物。
- 前記疾患または状態がメタボリックシンドロームである、請求項4に記載の組成物。
- 前記疾患または状態が脂肪肝である、請求項4に記載の組成物。
- 前記疾患または状態が非アルコール性脂肪性肝炎である、請求項4に記載の組成物。
- 前記式(I)の化合物が以下:
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸o−トリルアミド;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸フェニルアミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−[(チオフェン−2−カルボニル)アミノ]チアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−(シクロヘキサンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(2,3−ジヒドロ−ベンゾ[1,4]ジオキシン−6−イル)アミド;
2−(4−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ピリジン−3−イルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸(5−メチル[1,3,4]チアジアゾール−2−イル)アミド;
2−[(フラン−2−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸o−トリルアミド;
2−[(フラン−2−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−(3−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−[(フラン−2−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−[(フラン−2−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
2−[(フラン−2−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−(2−フェノキシアセチルアミノ)チアゾール−5−カルボン酸フェニルアミド;
4−メチル−2−(2−フェノキシアセチルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
2−クロロ−N−[4−メチル−5−(モルホリン−4−カルボニル)チアゾール−2−イル]ベンズアミド;
2−(3−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−(2−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−アセチルアミノ−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
2−アセチルアミノ−4−メチルチアゾール−5−カルボン酸シクロヘキシルアミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸フェニルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸インダン−5−イルアミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸フェニルアミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸フェニルアミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸o−トリルアミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
N−[4−メチル−5−(ピペリジン−1−カルボニル)−チアゾール−2−イル]ベンズアミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸ピリジン−3−イルアミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸ベンジルアミド;
[(2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボニル)アミノ]酢酸エチルエステル;
N−[4−メチル−5−(モルホリン−4−カルボニル)チアゾール−2−イル]プロピオンアミド;
N−(5−ベンジルカルバモイル−4−メチルチアゾール−2−イル)イソニコチンアミド;
N−[5−(3−クロロフェニルカルバモイル)−4−メチルチアゾール−2−イル]イソニコチンアミド;
N−[5−(2−クロロフェニルカルバモイル)−4−メチルチアゾール−2−イル]イソニコチンアミド;
N−(4−オキソ−5,6,7,8−テトラヒドロ−4H−チアゾロ[5,4−c]アゼピン−2−イル)アセトアミド;
N−(7,7−ジメチル−4−オキソ−5,6,7,8−テトラヒドロ−4H−チアゾロ[5,4−c]アゼピン−2−イル)アセトアミド;
2−(3−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸フェニルアミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸o−トリルアミド;
2−(2−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸o−トリルアミド;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
4−メチル−2−(3−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−(3−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
4−メチル−2−(2−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(2−クロロフェニル)アミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸(2−クロロフェニル)アミド;
4−メチル−2−(3−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(2−クロロフェニル)アミド;
2−(3−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2,3−ジヒドロ−ベンゾ[1,4]ジオキシン−6−イル)アミド;
2−(4−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2,3−ジヒドロ−ベンゾ[1,4]ジオキシン−6−イル)アミド;
4−メチル−2−(3−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(2,3−ジヒドロベンゾ[1,4]ジオキシン−6−イル)アミド;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
4−メチル−2−(3−メチルベンゾイルアミノ)チアゾール−5−カルボン酸インダン−5−イルアミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸シクロヘキシルアミド;
2−フルオロ−N−[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]ベンズアミド;
4−ブロモ−N−[4−メチル−5−(モルホリン−4−カルボニル)チアゾール−2−イル]ベンズアミド;
4−メトキシ−N−[4−メチル−5−(モルホリン−4−カルボニル)チアゾール−2−イル]ベンズアミド;
2−(シクロヘキサンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸o−トリルアミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−(4−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(2,3−ジヒドロベンゾ[1,4]ジオキシン−6−イル)アミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸(2,3−ジヒドロ−ベンゾ[1,4]ジオキシン−6−イル)アミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸インダン−5−イルアミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(4−クロロフェニル)アミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(3−クロロフェニル)アミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(2−クロロフェニル)アミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸フェニルアミド;
2−(シクロヘキサンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−(シクロヘキサンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[5−(2−クロロ−フェニルカルバモイル)−4−メチルチアゾール−2−イル]アミド;
2−(シクロヘキサンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
{[2−(4−メトキシ−ベンゾイルアミノ)−4−メチルチアゾール−5−カルボニル]アミノ}酢酸エチルエステル;
3−フルオロ−N−[4−メチル−5−(モルホリン−4−カルボニル)チアゾール−2−イル]ベンズアミド;
2−[(5−クロロ−3−メチル−1−フェニル−1H−ピラゾール−4−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸シクロヘキシルアミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(2−ジメチルアミノエチル)アミド;
2−[(フラン−2−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸フェニルアミド;
2−[(アダマンタン−1−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸フェニルアミド;
2−[(アダマンタン−1−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−(3−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−[(フラン−2−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−(3−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−(3−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
2−(3−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2,3−ジヒドロ−ベンゾ[1,4]ジオキシン−6−イル)アミド;
2−(3−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
{[2−(3−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボニル]アミノ}酢酸エチルエステル;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(5−メチル[1,3,4]チアジアゾール−2−イル)アミド;
2−(3−メトキシ−ベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
2−[(アダマンタン−1−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸(4−メチル−5−フェニルカルバモイル−チアゾール−2−イル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸(4−メチル−5−o−トリルカルバモイル−チアゾール−2−イル)アミド;
2−[(5−クロロ−3−メチル−1−フェニル−1H−ピラゾール−4−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−[(5−クロロ−3−メチル−1−フェニル−1H−ピラゾール−4−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[5−(2,3−ジヒドロ−ベンゾ[1,4]ジオキシン−6−イルカルバモイル)−4−メチルチアゾール−2−イル]アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[5−(インダン−5−イルカルバモイル)−4−メチルチアゾール−2−イル]アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[4−メチル−5−(5−メチル−[1,3,4]チアジアゾール−2−イルカルバモイル)チアゾール−2−イル]アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]アミド;
3−メチル−N−[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]ベンズアミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[5−(4−メトキシ−フェニルカルバモイル)−4−メチルチアゾール−2−イル]アミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸シクロヘキシルアミド;
2−(シクロヘキサンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
4−メチル−2−[(チオフェン−2−カルボニル)アミノ]チアゾール−5−カルボン酸(2,3−ジヒドロ−ベンゾ[1,4]ジオキシン−6−イル)アミド;
2−[(アダマンタン−1−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−(シクロヘキサンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
4−メチル−2−(3−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−(2−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−(2−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
2−(3−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[5−(4−クロロ−フェニルカルバモイル)−4−メチルチアゾール−2−イル]アミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−アセチルアミノ−4−メチルチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
2−アセチルアミノ−4−メチルチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−アセチルアミノ−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(5−メチル[1,3,4]チアジアゾール−2−イル)アミド;
2−(4−ブロモベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸フェニルアミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−プロピオニルアミノ−チアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸(2−クロロフェニル)アミド;
{[2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボニル]アミノ}酢酸エチルエステル;
{[2−(3−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボニル]アミノ}酢酸エチルエステル;
2−(2−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
N−[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]−2−フェノキシアセトアミド;
2−(4−tert−ブチルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−(4−tert−ブチルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−(4−tert−ブチルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
2−(4−tert−ブチルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸シクロヘキシルアミド;
2−(4−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(5−メチル[1,3,4]チアジアゾール−2−イル)アミド;
4−メチル−2−(4−ニトロ−ベンゾイルアミノ)チアゾール−5−カルボン酸o−トリルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
4−メチル−2−(2−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
4−メチル−2−(2−フェノキシアセチルアミノ)チアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[5−(4−ブロモ−フェニルカルバモイル)−4−メチルチアゾール−2−イル]アミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸(4−クロロフェニル)アミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
4−メチル−2−(2−フェノキシアセチルアミノ)チアゾール−5−カルボン酸(3−クロロフェニル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[5−(3−クロロ−フェニルカルバモイル)−4−メチルチアゾール−2−イル]アミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸o−トリルアミド;
4−メチル−2−(2−フェノキシ−アセチルアミノ)チアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸(2,3−ジヒドロベンゾ[1,4]ジオキシン−6−イル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸(5−ベンジルカルバモイル−4−メチルチアゾール−2−イル)アミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸[5−(3−メトキシ−フェニルカルバモイル)−4−メチルチアゾール−2−イル]アミド;
4−メチル−2−(2−メチルベンゾイルアミノ)チアゾール−5−カルボン酸インダン−5−イルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−(2−フェノキシアセチルアミノ)チアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸(4−メトキシフェニル)アミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸o−トリルアミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸(4−クロロフェニル)アミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(2,3−ジヒドロベンゾ[1,4]ジオキシン−6−イル)アミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
4−フルオロ−N−[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]ベンズアミド;
2−(4−tert−ブチルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸シクロヘキシルアミド;
N−[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]プロピオンアミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−(3−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(2−クロロフェニル)アミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸フェニルアミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸シクロヘキシルアミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸(2,3−ジヒドロベンゾ[1,4]ジオキシン−6−イル)アミド;
2−(4−tert−ブチルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸フェニルアミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸フェニルアミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸o−トリルアミド;
4−メチル−2−[(チオフェン−2−カルボニル)アミノ]チアゾール−5−カルボン酸(5−メチル−[1,3,4]チアジアゾール−2−イル)アミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(2−クロロフェニル)アミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸インダン−5−イルアミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(2−ヒドロキシ−エチル)アミド;
3−メチル−1−フェニル−1H−チエノ[2,3−c]ピラゾール−5−カルボン酸(5−シクロヘキシルカルバモイル−4−メチルチアゾール−2−イル)アミド;
{[2−(2−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボニル]アミノ}酢酸エチルエステル;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
2−(シクロヘキサンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
N−[4−メチル−5−(モルホリン−4−カルボニル)チアゾール−2−イル]−3−フェニルアクリルアミド;
N−[4−メチル−5−(モルホリン−4−カルボニル)チアゾール−2−イル]−4−ニトロベンズアミド;
{[4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボニル]アミノ}酢酸エチルエステル;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(2,3−ジヒドロベンゾ[1,4]ジオキシン−6−イル)アミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸ピリジン−3−イルアミド;
N−[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]−3−フェニルアクリルアミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸シクロヘキシルアミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸(5−メチル−[1,3,4]チアジアゾール−2−イル)アミド;
4−メチル−2−プロピオニルアミノチアゾール−5−カルボン酸o−トリルアミド;
シクロプロパンカルボン酸[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]アミド;
4−メチル−2−(2−フェノキシアセチルアミノ)チアゾール−5−カルボン酸o−トリルアミド;
4−メチル−2−(2−フェノキシアセチルアミノ)チアゾール−5−カルボン酸(2,3−ジヒドロベンゾ[1,4]ジオキシン−6−イル)アミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸(4−ブロモフェニル)アミド;
4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボン酸インダン−5−イルアミド;
2−[(アダマンタン−1−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸シクロヘキシルアミド;
2−(3−クロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ピリジン−3−イルアミド;
2−(3−クロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸シクロヘキシルアミド;
{[4−メチル−2−(3,4,5−トリメトキシベンゾイルアミノ)チアゾール−5−カルボニル]アミノ}酢酸エチルエステル;
4−メチル−2−(2−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(3−クロロフェニル)アミド;
2−(4−クロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸シクロヘキシルアミド;
4−メチル−2−(4−メチルベンゾイルアミノ)チアゾール−5−カルボン酸(2−ジメチルアミノエチル)アミド;
5−tert−ブチル−2−メチル−2H−ピラゾール−3−カルボン酸(7,7−ジメチル−4−オキソ−5,6,7,8−テトラヒドロ−4H−チアゾロ[5,4−c]アゼピン−2−イル)アミド;
2−[(5−クロロ−3−メチル−1−フェニル−1H−ピラゾール−4−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸インダン−5−イルアミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸インダン−5−イルアミド;
2−アセチルアミノ−4−メチルチアゾール−5−カルボン酸(5−メチル[1,3,4]チアジアゾール−2−イル)アミド;
2−クロロ−N−(7,7−ジメチル−4−オキソ−5,6,7,8−テトラヒドロ−4H−チアゾロ[5,4−c]アゼピン−2−イル)−ベンズアミド;
N−(7,7−ジメチル−4−オキソ−5,6,7,8−テトラヒドロ−4H−チアゾロ[5,4−c]アゼピン−2−イル)ベンズアミド;
N−(4−オキソ−5,6,7,8−テトラヒドロ−4H−チアゾロ[5,4−c]アゼピン−2−イル)ベンズアミド;
2−クロロ−N−(4−オキソ−5,6,7,8−テトラヒドロ−4H−チアゾロ[5,4−c]アゼピン−2−イル)ベンズアミド;
2−(3,4−ジメトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ジメチルアミド;
4−メチル−2−(2−フェニル−プロピオニルアミノ)チアゾール−5−カルボン酸ジメチルアミド;
2−(2,6−ジフルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ジメチルアミド;
3−クロロ−N−[4−メチル−5−(ピペリジン−1−カルボニル)チアゾール−2−イル]ベンズアミド;
2−[2−(4−クロロ−2−メチルフェノキシ)プロピオニルアミノ]−4−メチルチアゾール−5−カルボン酸ジメチルアミド;
6,8−ジメチル−2−ピリジン−4−イルキノリン−4−カルボン酸(5−ジメチルカルバモイル−4−メチルチアゾール−2−イル)アミド;
4−メチル−2−[(3−メチルベンゾフラン−2−カルボニル)アミノ]チアゾール−5−カルボン酸ジメチルアミド;
2−アセチルアミノ−4−メチルチアゾール−5−カルボン酸(3−クロロフェニル)アミド;
4−メチル−2−(2−フェノキシアセチルアミノ)チアゾール−5−カルボン酸インダン−5−イルアミド;
5−(7,7−ジメチル−4−オキソ−5,6,7,8−テトラヒドロ−4H−チアゾロ[5,4−c]アゼピン−2−イルカルバモイル)−チオフェン−2−カルボン酸メチルエステル;
4−メチル−2−(3−メチルベンゾイルアミノ)チアゾール−5−カルボン酸シクロヘキシルアミド;
4−メチル−2−(3−フェニルアクリロイルアミノ)チアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
4−メチル−2−(4−ニトロベンゾイルアミノ)チアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
2−[(アダマンタン−1−カルボニル)アミノ]−4−メチルチアゾール−5−カルボン酸(3−メトキシフェニル)アミド;
N−[5−(2−シクロプロピルエチルカルバモイル)−4−メチルチアゾール−2−イル]イソニコチンアミド;
N−(4−メチル−5−フェネチルカルバモイルチアゾール−2−イル)イソニコチンアミド;
N−[4−メチル−5−(3−フェニルプロピルカルバモイル)チアゾール−2−イル]イソニコチンアミド;
N−[5−(4−クロロベンジルカルバモイル)−4−メチルチアゾール−2−イル]イソニコチンアミド;
2−(シクロプロパンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸4−クロロ−ベンジルアミド;
2−(2,5−ジフルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(シクロブタンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−[(2−フェニルシクロプロパンカルボニル)アミノ]チアゾール−5−カルボン酸ベンジルアミド;
2−(2−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(2,2−ジメチルプロピオニルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(2−トリフルオロメチルベンゾイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
2−(4−クロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(4−トリフルオロメチルベンゾイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
2−(2−クロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(2,4−ジクロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(シクロペンタンカルボニルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(2−クロロ−4−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(3−クロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(2−トリフルオロメトキシベンゾイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
2−(3,5−ジクロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(3−シアノベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(5−クロロ−2−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(3−フルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(4−トリフルオロメトキシベンゾイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(3−トリフルオロメチルベンゾイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
2−(3−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−[(ナフタレン−1−カルボニル)アミノ]チアゾール−5−カルボン酸ベンジルアミド;
2−(4−シアノベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(3,5−ジフルオロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(3−トリフルオロメトキシベンゾイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
2−(4−メトキシベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(3−メタンスルホニルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(2−メタンスルホニルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−ベンゾイルアミノ−4−トリフルオロメチルチアゾール−5−カルボン酸ベンジルアミド;
N−(5−ベンジルカルバモイル−4−メチルチアゾール−2−イル)ニコチンアミド;
2−(3,4−ジクロロベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(4−メタンスルホニルベンゾイルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(3−フェニルプロピオニルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
2−ベンジルアミノ−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−フェニルアセチルアミノチアゾール−5−カルボン酸ベンジルアミド;
2−ベンゾイルアミノ−4−フェニルチアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(3−フェニルウレイド)チアゾール−5−カルボン酸ベンジルアミド;
2−[3−(4−フルオロフェニル)ウレイド]−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−[3−(4−クロロフェニル)ウレイド]−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−(2−シクロプロピルアセチルアミノ)−4−メチルチアゾール−5−カルボン酸ベンジルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸2−トリフルオロメチルベンジルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸3−クロロベンジルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸シクロプロピルメチル−アミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸3−フルオロベンジルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸2−クロロベンジルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸2−フルオロベンジルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸4−フルオロベンジルアミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸ベンジルメチルアミド;
2−ベンゾイルアミノ−4−クロロチアゾール−5−カルボン酸ベンジルアミド;
2−[(4−ペンチルベンゾイル)アミノ]−N−(フェニルメチル)−4−(トリフルオロメチル)−5−チアゾールカルボキサミド;
2−ベンゾイルアミノ−4−メチルチアゾール−5−カルボン酸(1−フェニルプロピル)アミド;
4−メチル−2−(トルエン−4−スルホニルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−[4−(2H−テトラゾール−5−イル)ベンゾイルアミノ]チアゾール−5−カルボン酸ベンジルアミド;
2−ベンゾイルアミノ−チアゾール−5−カルボン酸ベンジルアミド;
4−アミノ−2−ベンゾイルアミノチアゾール−5−カルボン酸ベンジルアミド;
N−[5−(N−ベンゾイルヒドラジノカルボニル)−4−メチルチアゾール−2−イル]ベンズアミド;
N−[5−(イミダゾール−1−カルボニル)−4−メチルチアゾール−2−イル]ベンズアミド;
4−メチル−2−(4−フェニルブチリルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−(5−フェニルペンタノイルアミノ)チアゾール−5−カルボン酸ベンジルアミド;
4−メチル−2−[4−(2−オキソ−2H−ピリジン−1−イル)ベンゾイルアミノ]−チアゾール−5−カルボン酸ベンジルアミド;
2−[(5−ベンジルカルバモイル−4−メチル−チアゾール−2−イルカルバモイル)メチル]安息香酸;
N−(5−ベンジルカルバモイル−4−メチルチアゾール−2−イル)−2−メトキシイソニコチンアミド;
2−オキソ−1,2−ジヒドロピリジン−4−カルボン酸(5−ベンジルカルバモイル−4−メチルチアゾール−2−イル)アミド;
2−オキソ−1−フェニル−1,2−ジヒドロピリジン−4−カルボン酸(5−ベンジルカルバモイル−4−メチル−チアゾール−2−イル)アミド;
N,4−ジベンジル−2−(3−フェニルプロパンアミド)チアゾール−5−カルボキサミド;
2−ベンズアミド−N,4−ジベンジルチアゾール−5−カルボキサミド;
2−(4−ブロモ−2−ヒドロキシメチルベンゾイルアミノ)−4−メチル−チアゾール−5−カルボン酸ベンジルアミド;
N−ベンジル−4−メチル−2−(N−メチルベンズアミド)チアゾール−5−カルボキサミド;
N−ベンジル−N,4−ジメチル−2−(N−メチルベンズアミド)チアゾール−5−カルボキサミド;
2−(4−((1H−ピラゾール−1−イル)メチル)ベンズアミド)−N−ベンジル−4−メチルチアゾール−5−カルボキサミド;
N−ベンジル−4−(モルホリノメチル)−2−(3−フェニルプロパンアミド)チアゾール−5−カルボキサミド;
N−ベンジル−2−(4−ベンジルベンズアミド)−4−メチルチアゾール−5−カルボキサミド;
2−(4−ベンジルベンゾイルアミノ)−4−ジエチルアミノメチルチアゾール−5−カルボン酸ベンジルアミド;
2−ベンズアミド−N−ベンジル−4−((ジエチルアミノ)メチル)チアゾール−5−カルボキサミド;
2−(4−ベンジルベンズアミド)−N−(2−シアノエチル)−4−メチルチアゾール−5−カルボキサミド;
2−(4−ベンジルベンズアミド)−N−エチル−4−メチルチアゾール−5−カルボキサミド;および
N−ベンジル−2−(4−ベンジルベンズアミド)−4−((メチルアミノ)メチル)チアゾール−5−カルボキサミド
からなる群から選択される、請求項1〜9のいずれか一項に記載の組成物。 - 薬学的に許容可能な賦形剤、および治療有効量の式(I):
Wは、−O−、−OC(O)−、−OC(O)N(R5)−、−OS(O)2N(R5)−、−C(O)−、−C(O)O−、−C(O)N(R5)−、−N(R5)−、−N(R5)C(O)−、−N(R5)C(O)O−、−N(R5)C(O)N(R5)−、−N(R5)S(O)2−、−S(O)t−(ここで、tは0、1もしくは2である)または−S(O)2N(R5)−から選択され;
Vは、−C(O)−、−C(O)N(R5)−、−C(O)O−、−S(O)t−(ここで、tは1もしくは2である)または直接結合から選択され;
R1は、アルキル、アルケニル、−R6−OR7、ヒドロキシアルケニル、シクロアルキル、シクロアルキルアルキル、アリール、アラルキル、アラルケニル、ヘテロシクリル、ヘテロシクリルアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群から選択されるか;
あるいは、R1は2〜4個の環を有する多環構造体であり、該環は、シクロアルキル、ヘテロシクリル、アリールおよびヘテロアリールからなる群から独立に選択され、かつ、該環のいくつかまたはすべては互いに縮合していてもよく;
R2は、アルキル、アルケニル、−R6−OR7、ヒドロキシアルケニル、シクロアルキル、シクロアルキルアルキル、アリール、アラルキル、アラルケニル、ヘテロシクリル、ヘテロシクリルアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群から選択されるか;
あるいは、R2は2〜4個の環を有する多環構造体であり、該環は、シクロアルキル、ヘテロシクリル、アリールおよびヘテロアリールからなる群から独立に選択され、かつ、該環のいくつかまたはすべては互いに縮合していてもよく;
R3は、水素、アルキル、アルケニル、ヒドロキシアルキル、ヒドロキシアルケニル、アルコキシアルキル、シクロアルキル、シクロアルキルアルキル、ヘテロシクリル、アリール、アラルキル、ヘテロアリール、フルオロ、クロロ、ブロモ、トリハロアルキル、トリハロアルコキシ、シアノ、ニトロ、−OR4、−OC(O)R2、−OC(O)N(R4)(R5)、−OS(O)2N(R4)(R5)、−S(O)tR2(ここで、tは0、1もしくは2である)、−S(O)tN(R4)(R5)(ここで、tは1もしくは2である)、−C(O)R2、−C(O)OR2、−C(O)N(R4)(R5)、−N(R4)(R5)、−N(R5)C(O)R5、−N(R5)C(O)OR5、−N(R5)C(O)N(R4)(R5)または−N(R5)S(O)2R2から選択され;
各R4およびR5は、−R6−N(R7)2、−R6−OR7、−R6−C(O)OR7、水素、アルキル、シクロアルキルアルキルおよびアラルキルからなる群から独立に選択され;
各R6は直鎖または分岐鎖のアルキレン鎖であり;
各R7は水素、アルキル、アリールまたはアラルキルである、
医薬組成物。 - ヒトのステアロイル−CoAデサチュラーゼ(hSCD)活性を阻害する方法であって、hSCD源を式(I):
Wは、−O−、−OC(O)−、−OC(O)N(R5)−、−OS(O)2N(R5)−、−C(O)−、−C(O)O−、−C(O)N(R5)−、−N(R5)−、−N(R5)C(O)−、−N(R5)C(O)O−、−N(R5)C(O)N(R5)−、−N(R5)S(O)2−、−S(O)t−(ここで、tは0、1もしくは2である)または−S(O)2N(R5)−から選択され;
Vは、−C(O)−、−C(O)N(R5)−、−C(O)O−、−S(O)t−(ここで、tは1もしくは2である)または直接結合から選択され;
R1は、アルキル、アルケニル、−R6−OR7、ヒドロキシアルケニル、シクロアルキル、シクロアルキルアルキル、アリール、アラルキル、アラルケニル、ヘテロシクリル、ヘテロシクリルアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群から選択されるか;
あるいは、R1は2〜4個の環を有する多環構造体であり、該環は、シクロアルキル、ヘテロシクリル、アリールおよびヘテロアリールからなる群から独立に選択され、かつ、該環のいくつかまたはすべては互いに縮合していてもよく;
R2は、アルキル、アルケニル、−R6−OR7、ヒドロキシアルケニル、シクロアルキル、シクロアルキルアルキル、アリール、アラルキル、アラルケニル、ヘテロシクリル、ヘテロシクリルアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群から選択されるか;
あるいは、R2は2〜4個の環を有する多環構造体であり、該環は、シクロアルキル、ヘテロシクリル、アリールおよびヘテロアリールからなる群から独立に選択され、かつ、該環のいくつかまたはすべては互いに縮合していてもよく;
R3は、水素、アルキル、アルケニル、ヒドロキシアルキル、ヒドロキシアルケニル、アルコキシアルキル、シクロアルキル、シクロアルキルアルキル、ヘテロシクリル、アリール、アラルキル、ヘテロアリール、フルオロ、クロロ、ブロモ、トリハロアルキル、トリハロアルコキシ、シアノ、ニトロ、−OR4、−OC(O)R2、−OC(O)N(R4)(R5)、−OS(O)2N(R4)(R5)、−S(O)tR2(ここで、tは0、1もしくは2である)、−S(O)tN(R4)(R5)(ここで、tは1もしくは2である)、−C(O)R2、−C(O)OR2、−C(O)N(R4)(R5)、−N(R4)(R5)、−N(R5)C(O)R5、−N(R5)C(O)OR5、−N(R5)C(O)N(R4)(R5)または−N(R5)S(O)2R2から選択され;
各R4およびR5は、−R6−N(R7)2、−R6−OR7、−R6−C(O)OR7、水素、アルキル、シクロアルキルアルキルおよびアラルキルからなる群から独立に選択され;
各R6は直鎖または分岐鎖のアルキレン鎖であり;
各R7は水素、アルキル、アリールまたはアラルキルである、方法。 - 哺乳動物におけるステアロイル−CoAデサチュラーゼ(SCD)によって媒介される疾患または状態を治療するための組成物であって、治療有効量の請求項1に記載の式(I)の化合物を含む、組成物。
- 前記疾患または状態が、メタボリックシンドローム、症候群X、糖尿病、インスリン抵抗性、耐糖能の低下、インスリン非依存性糖尿病、II型糖尿病、I型糖尿病、糖尿病の合併症、体重障害、体重減少、ボディマスインデックス、またはレプチンと関係がある疾患である、請求項13に記載の組成物。
- 前記メタボリックシンドロームが、異脂肪血症、肥満、インスリン抵抗性、高血圧症、ミクロアルブミン血症、高尿酸血症、および過凝固能亢進である、請求項14に記載の組成物。
- 前記体重障害が、肥満、過体重、悪液質、および食欲不振である、請求項14に記載の組成物。
- 前記疾患または状態が皮膚障害である、請求項13に記載の組成物。
- 前記皮膚障害が、湿疹、ざ瘡、乾癬、あるいはケロイド瘢痕の形成または予防である、請求項17に記載の組成物。
- 治療有効量の、インスリン、インスリン誘導体または模倣体;インスリン分泌促進物質;インスリン分泌刺激スルホニル尿素レセプターリガンド;PPARリガンド;インスリン感作物質;ビグアニド;αグルコシダーゼ阻害剤;GLP−1、GLP−1類似体またはGLP−1模倣体;DPPIV阻害剤;HMG−CoA還元酵素阻害剤;スクアレンシンターゼ阻害剤;FXRまたはLXRリガンド;コレスチラミン;フィブラート;ニコチン酸;あるいはアスピリンと組み合わせて治療有効量の請求項1に記載の化合物を含む医薬組成物。
- ステアロイル−CoAデサチュラーゼの阻害によって被験体における該ステアロイル−CoAデサチュラーゼにより媒介される障害または疾患を治療するための医薬組成物を調製するための、請求項1に記載の式(I)の化合物の使用。
- 薬物として使用するための請求項1に記載の式(I)の化合物。
- ステアロイル−CoAデサチュラーゼの阻害によって被験体における該ステアロイル−CoAデサチュラーゼにより媒介される障害または疾患を治療するための医薬組成物を調製するための、請求項10に記載の式(I)の化合物の使用。
- 薬物として使用するための請求項11に記載の医薬組成物。
- ステアロイル−CoAデサチュラーゼの阻害によって被験体における該ステアロイル−CoAデサチュラーゼにより媒介される障害または疾患を治療するための薬物を調製するための、請求項11に記載の医薬組成物の使用。
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CN101084207A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶抑制剂的用途 |
BRPI0515477A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos bicìclicos e o uso dos mesmos como inibidores de estaroil-coa-desaturase (scd) |
EP2289510A1 (en) | 2004-09-20 | 2011-03-02 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
WO2006034440A2 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
DE602005022113D1 (de) * | 2005-01-07 | 2010-08-12 | Hoffmann La Roche | Phenyl)methanon-derivate als glycin-transporter 1 (glyt-1) hemmer zur behandlung von neurologischen und neuropsychiatrischen erkrankungen |
WO2006106423A2 (en) | 2005-04-07 | 2006-10-12 | Pfizer Inc. | Amino sulfonyl derivatives as inhibitors of human 11-.beta.-hydrosysteroid dehydrogenase |
CN101208089A (zh) | 2005-06-03 | 2008-06-25 | 泽农医药公司 | 氨基噻唑衍生物作为人硬酯酰-CoA去饱和酶抑制剂 |
AU2006255465A1 (en) | 2005-06-09 | 2006-12-14 | Merck Frosst Canada Ltd | Azacyclohexane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
US7662819B2 (en) * | 2007-04-09 | 2010-02-16 | Gilead Palo Alto, Inc. | Pteridinone derivatives for use as stearoyl CoA desaturase inhibitors |
-
2006
- 2006-06-05 CN CNA200680019628XA patent/CN101208089A/zh active Pending
- 2006-06-05 EP EP06784578A patent/EP2029138A1/en not_active Withdrawn
- 2006-06-05 WO PCT/US2006/021660 patent/WO2007130075A1/en active Application Filing
- 2006-06-05 US US11/916,243 patent/US8541457B2/en not_active Expired - Fee Related
- 2006-06-05 EP EP12005821A patent/EP2540296A1/en not_active Withdrawn
- 2006-06-05 JP JP2008525998A patent/JP2009513563A/ja active Pending
- 2006-06-05 CA CA002618646A patent/CA2618646A1/en not_active Abandoned
- 2006-06-05 BR BRPI0611187-4A patent/BRPI0611187A2/pt not_active IP Right Cessation
- 2006-06-05 AU AU2006343359A patent/AU2006343359A1/en not_active Abandoned
- 2006-06-05 MX MX2007015216A patent/MX2007015216A/es unknown
-
2012
- 2012-09-14 US US13/620,339 patent/US20130096056A1/en not_active Abandoned
-
2013
- 2013-03-05 JP JP2013042546A patent/JP2013100376A/ja active Pending
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