JP2003510359A - 化合物および方法 - Google Patents
化合物および方法Info
- Publication number
- JP2003510359A JP2003510359A JP2001527795A JP2001527795A JP2003510359A JP 2003510359 A JP2003510359 A JP 2003510359A JP 2001527795 A JP2001527795 A JP 2001527795A JP 2001527795 A JP2001527795 A JP 2001527795A JP 2003510359 A JP2003510359 A JP 2003510359A
- Authority
- JP
- Japan
- Prior art keywords
- anilino
- triazole
- methyl
- benzylthio
- ylthio
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims description 403
- 238000000034 method Methods 0.000 title claims description 343
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 201000011510 cancer Diseases 0.000 claims abstract description 14
- 230000033115 angiogenesis Effects 0.000 claims abstract description 13
- 230000001404 mediated effect Effects 0.000 claims abstract description 12
- 206010029113 Neovascularisation Diseases 0.000 claims abstract description 10
- 208000008589 Obesity Diseases 0.000 claims abstract description 9
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 9
- 206010038934 Retinopathy proliferative Diseases 0.000 claims abstract description 9
- 201000011066 hemangioma Diseases 0.000 claims abstract description 9
- 235000020824 obesity Nutrition 0.000 claims abstract description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 9
- 230000003143 atherosclerotic effect Effects 0.000 claims abstract description 7
- -1 3-anilino-5- (cyclohexylmethylthio) -1,2,4-triazole 3-anilino-5- (propylacetylthio) -1,2,4-triazole Chemical compound 0.000 claims description 436
- 125000000217 alkyl group Chemical group 0.000 claims description 158
- 238000004519 manufacturing process Methods 0.000 claims description 119
- 150000002540 isothiocyanates Chemical class 0.000 claims description 52
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 43
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- 125000000304 alkynyl group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- JVESHYAZMYQQGG-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 JVESHYAZMYQQGG-UHFFFAOYSA-N 0.000 claims description 15
- HOQOTPFYKDHPPO-UHFFFAOYSA-N n-(3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-yl)pyridin-3-amine Chemical compound C=1C=CN=CC=1NC(N=1)=NNC=1SC1=CC=CS1 HOQOTPFYKDHPPO-UHFFFAOYSA-N 0.000 claims description 15
- QBUZLNWDECJZMT-UHFFFAOYSA-N 3-benzylsulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C=1C=CC=CC=1CSC(NN=1)=NC=1NC1=CC=CC=C1 QBUZLNWDECJZMT-UHFFFAOYSA-N 0.000 claims description 13
- SSVJBYATJWWGDE-UHFFFAOYSA-N n-(4-methylphenyl)-3-(5-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(C)=CC=C1SC1=NNC(NC=2C=CC(C)=CC=2)=N1 SSVJBYATJWWGDE-UHFFFAOYSA-N 0.000 claims description 13
- MSCIKZGQDUGLMX-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 MSCIKZGQDUGLMX-UHFFFAOYSA-N 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- HSTMOEDERLQUGN-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 HSTMOEDERLQUGN-UHFFFAOYSA-N 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- NAFJUZKFEUUDKV-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 NAFJUZKFEUUDKV-UHFFFAOYSA-N 0.000 claims description 10
- UBZUXVQIHHRQHG-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 UBZUXVQIHHRQHG-UHFFFAOYSA-N 0.000 claims description 10
- CNWQUDKZKSKAST-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2,6-dimethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 CNWQUDKZKSKAST-UHFFFAOYSA-N 0.000 claims description 10
- FFIDUOXKZSOIBZ-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2-ethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 FFIDUOXKZSOIBZ-UHFFFAOYSA-N 0.000 claims description 10
- LCGRNWJSKOHUBU-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 LCGRNWJSKOHUBU-UHFFFAOYSA-N 0.000 claims description 10
- AQBIMSLMBXMPSV-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 AQBIMSLMBXMPSV-UHFFFAOYSA-N 0.000 claims description 10
- OIYTXJVMQLCGKD-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C=C(F)C(F)=CC=3)NN=2)=C1 OIYTXJVMQLCGKD-UHFFFAOYSA-N 0.000 claims description 10
- SQPPNLAFFBHMTB-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(4-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 SQPPNLAFFBHMTB-UHFFFAOYSA-N 0.000 claims description 10
- JCCLYBLQSDKYDK-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 JCCLYBLQSDKYDK-UHFFFAOYSA-N 0.000 claims description 10
- MKZCDFBGFBYCCQ-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 MKZCDFBGFBYCCQ-UHFFFAOYSA-N 0.000 claims description 10
- NSQLTDMTLKMKJF-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 NSQLTDMTLKMKJF-UHFFFAOYSA-N 0.000 claims description 10
- KCAHISAOWMHACF-UHFFFAOYSA-N 5-benzylsulfanyl-3-ethyl-n-phenyl-1,2,4-triazol-3-amine Chemical compound N1=NC(SCC=2C=CC=CC=2)=NC1(CC)NC1=CC=CC=C1 KCAHISAOWMHACF-UHFFFAOYSA-N 0.000 claims description 10
- QHSDUGQGPSMGLM-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 QHSDUGQGPSMGLM-UHFFFAOYSA-N 0.000 claims description 10
- CWWQVJYPJGUIIE-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-3-[(4-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 CWWQVJYPJGUIIE-UHFFFAOYSA-N 0.000 claims description 10
- NCNIBQLSTUFUFR-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 NCNIBQLSTUFUFR-UHFFFAOYSA-N 0.000 claims description 10
- YMRMQAFSXBDKPX-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-[(4-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 YMRMQAFSXBDKPX-UHFFFAOYSA-N 0.000 claims description 10
- SVBPPCULWIQVTO-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C=C(OC)C(OC)=CC=2)=NN1 SVBPPCULWIQVTO-UHFFFAOYSA-N 0.000 claims description 10
- LXPYJMBMOSTEOW-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-[(3-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC(CSC=2NN=C(NC=3C=C(OC)C(OC)=CC=3)N=2)=C1 LXPYJMBMOSTEOW-UHFFFAOYSA-N 0.000 claims description 10
- IPTPWKJLWLOGSK-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(4-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 IPTPWKJLWLOGSK-UHFFFAOYSA-N 0.000 claims description 10
- YJFCWNYTKZVLEA-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=C(F)C(F)=CC=C1CSC1=NC(NC=2C=CC(Cl)=CC=2)=NN1 YJFCWNYTKZVLEA-UHFFFAOYSA-N 0.000 claims description 10
- GNKKFOKAICLWIY-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)OC)=N1 GNKKFOKAICLWIY-UHFFFAOYSA-N 0.000 claims description 10
- SWBHUFGZKMHJDT-UHFFFAOYSA-N n-[3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound COC1=CC=CC=C1CSC1=NC(NC=2C=NC=CC=2)=NN1 SWBHUFGZKMHJDT-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- DABRIDCJWJCDLJ-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC2=C(C=CS2)Cl)=NN1 DABRIDCJWJCDLJ-UHFFFAOYSA-N 0.000 claims description 9
- DHHDNUXVQYYLPA-UHFFFAOYSA-N 3-(3-methylthiophen-2-yl)sulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CSC(SC=2N=C(NC=3C=CC=CC=3)NN=2)=C1C DHHDNUXVQYYLPA-UHFFFAOYSA-N 0.000 claims description 9
- JPZYMONDMULCCK-UHFFFAOYSA-N 3-(5-bromothiophen-2-yl)sulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(Br)=CC=C1SC1=NNC(NC=2C=CC=CC=2)=N1 JPZYMONDMULCCK-UHFFFAOYSA-N 0.000 claims description 9
- PGDTXMNNIGGIQT-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)sulfanyl-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound S1C(Cl)=CC=C1SC1=NNC(NC=2C=CC=CC=2)=N1 PGDTXMNNIGGIQT-UHFFFAOYSA-N 0.000 claims description 9
- ZGYUDXYEKJBWGQ-UHFFFAOYSA-N 3-(furan-2-ylsulfanyl)-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC=2OC=CC=2)=NN1 ZGYUDXYEKJBWGQ-UHFFFAOYSA-N 0.000 claims description 9
- SMQLCSMMAKTBSJ-UHFFFAOYSA-N 3-(furan-3-ylsulfanyl)-n-(2-methoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC2=COC=C2)=NN1 SMQLCSMMAKTBSJ-UHFFFAOYSA-N 0.000 claims description 9
- NXBLUWQGGLQYQM-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C(=CC=CC=3)F)NN=2)=C1 NXBLUWQGGLQYQM-UHFFFAOYSA-N 0.000 claims description 9
- GDZHHXOYXPKDLO-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 GDZHHXOYXPKDLO-UHFFFAOYSA-N 0.000 claims description 9
- YYIJNRPVYDYLRE-UHFFFAOYSA-N 3-[(2-fluorophenyl)methylsulfanyl]-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)F)=N1 YYIJNRPVYDYLRE-UHFFFAOYSA-N 0.000 claims description 9
- PPUFZAUHFAXGBM-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(2,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 PPUFZAUHFAXGBM-UHFFFAOYSA-N 0.000 claims description 9
- CQFAERVRCDLGBQ-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 CQFAERVRCDLGBQ-UHFFFAOYSA-N 0.000 claims description 9
- KTWYUXALXXVYQE-UHFFFAOYSA-N 3-[(3,4-difluorophenyl)methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound C1=C(F)C(F)=CC=C1CSC1=NC(NC=2C=CC=CC=2)=NN1 KTWYUXALXXVYQE-UHFFFAOYSA-N 0.000 claims description 9
- MWNYEANTJBPRNF-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2N=C(SCC=3C=CC(F)=CC=3)NN=2)=C1 MWNYEANTJBPRNF-UHFFFAOYSA-N 0.000 claims description 9
- CVZWCPNYLAZZKB-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 CVZWCPNYLAZZKB-UHFFFAOYSA-N 0.000 claims description 9
- JZJFXCKLZBMUKY-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-methoxy-2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC(OC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 JZJFXCKLZBMUKY-UHFFFAOYSA-N 0.000 claims description 9
- CUQBEBOKLIGHEG-UHFFFAOYSA-N CC(C)c1ccccc1Nc1n[nH]c(Sc2ccoc2)n1 Chemical compound CC(C)c1ccccc1Nc1n[nH]c(Sc2ccoc2)n1 CUQBEBOKLIGHEG-UHFFFAOYSA-N 0.000 claims description 9
- DOYJEQSIVADNPC-UHFFFAOYSA-N CC(C)c1ccccc1Nc1n[nH]c(Sc2ccsc2)n1 Chemical compound CC(C)c1ccccc1Nc1n[nH]c(Sc2ccsc2)n1 DOYJEQSIVADNPC-UHFFFAOYSA-N 0.000 claims description 9
- NRIPGQLYDKKSSR-UHFFFAOYSA-N Fc1ccc(Nc2n[nH]c(Sc3ccoc3)n2)cc1 Chemical compound Fc1ccc(Nc2n[nH]c(Sc3ccoc3)n2)cc1 NRIPGQLYDKKSSR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- BZRABYOGPQHVJS-UHFFFAOYSA-N methyl 4-[[3-[(2-methoxyphenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C(=CC=CC=2)OC)=N1 BZRABYOGPQHVJS-UHFFFAOYSA-N 0.000 claims description 9
- WJUVOKOQWNBXMR-UHFFFAOYSA-N methyl 4-[[3-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 WJUVOKOQWNBXMR-UHFFFAOYSA-N 0.000 claims description 9
- FEKPHPGOKGXZOL-UHFFFAOYSA-N n-(2-ethylphenyl)-3-[(4-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 FEKPHPGOKGXZOL-UHFFFAOYSA-N 0.000 claims description 9
- XNPZSYHTBLCMEE-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 XNPZSYHTBLCMEE-UHFFFAOYSA-N 0.000 claims description 9
- BQOBXXPDLZZRJS-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-thiophen-3-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC=C1NC1=NC(SC2=CSC=C2)=NN1 BQOBXXPDLZZRJS-UHFFFAOYSA-N 0.000 claims description 9
- BBEIYRRUQXXVHC-UHFFFAOYSA-N n-(2-propan-2-ylphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 BBEIYRRUQXXVHC-UHFFFAOYSA-N 0.000 claims description 9
- REEAZBAQKRGCLX-UHFFFAOYSA-N n-(3,4-dimethoxyphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 REEAZBAQKRGCLX-UHFFFAOYSA-N 0.000 claims description 9
- DHAZWIIKGZEPGW-UHFFFAOYSA-N n-(4-butylphenyl)-3-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NNC(SCC=2C=C(F)C(F)=CC=2)=N1 DHAZWIIKGZEPGW-UHFFFAOYSA-N 0.000 claims description 9
- JPWRGMWKHAEHKC-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(2-fluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-amine Chemical compound FC1=CC=CC=C1CSC1=NC(NC=2C=CC(Cl)=CC=2)=NN1 JPWRGMWKHAEHKC-UHFFFAOYSA-N 0.000 claims description 9
- MMSDGZLDMNHFEJ-UHFFFAOYSA-N n-(4-fluorophenyl)-3-(furan-2-ylsulfanyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(SC=2OC=CC=2)=NN1 MMSDGZLDMNHFEJ-UHFFFAOYSA-N 0.000 claims description 9
- YASQUTIKKJKSSL-UHFFFAOYSA-N n-(4-fluorophenyl)-3-thiophen-3-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(SC2=CSC=C2)=NN1 YASQUTIKKJKSSL-UHFFFAOYSA-N 0.000 claims description 9
- IVCQNJJPZXCTQQ-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-thiophen-2-ylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC(SC=2SC=CC=2)=NN1 IVCQNJJPZXCTQQ-UHFFFAOYSA-N 0.000 claims description 9
- TWRSNUIWPOALRR-UHFFFAOYSA-N n-(4-methylphenyl)-3-(3-methylthiophen-2-yl)sulfanyl-1h-1,2,4-triazol-5-amine Chemical compound C1=CSC(SC=2N=C(NC=3C=CC(C)=CC=3)NN=2)=C1C TWRSNUIWPOALRR-UHFFFAOYSA-N 0.000 claims description 9
- ARJPWOXCGAOYMT-UHFFFAOYSA-N n-[3-[(3,4-difluorophenyl)methylsulfanyl]-1h-1,2,4-triazol-5-yl]pyridin-3-amine Chemical compound C1=C(F)C(F)=CC=C1CSC1=NC(NC=2C=NC=CC=2)=NN1 ARJPWOXCGAOYMT-UHFFFAOYSA-N 0.000 claims description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
- PWXLEAVSSVXZGL-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(2-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC=C1NC1=NC(SC2=C(C=CS2)Cl)=NN1 PWXLEAVSSVXZGL-UHFFFAOYSA-N 0.000 claims description 8
- CQUIZEMQWMKVMY-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(3-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC1=CC=CC(NC=2NN=C(SC3=C(C=CS3)Cl)N=2)=C1 CQUIZEMQWMKVMY-UHFFFAOYSA-N 0.000 claims description 8
- CWCKONMZORSQQK-UHFFFAOYSA-N 3-(3-chlorothiophen-2-yl)sulfanyl-n-(4-fluorophenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(SC2=C(C=CS2)Cl)=NN1 CWCKONMZORSQQK-UHFFFAOYSA-N 0.000 claims description 8
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- CLFNJJAUZYKYCJ-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-chlorophenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 CLFNJJAUZYKYCJ-UHFFFAOYSA-N 0.000 claims description 8
- FHIPHLQUMZUIKM-UHFFFAOYSA-N 5-[(5-anilino-1h-1,2,4-triazol-3-yl)sulfanylmethyl]furan-2-carbaldehyde Chemical compound O1C(C=O)=CC=C1CSC(N1)=NN=C1NC1=CC=CC=C1 FHIPHLQUMZUIKM-UHFFFAOYSA-N 0.000 claims description 8
- RFMCIVZPIQKMMO-UHFFFAOYSA-N 5-[[5-(2-methylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carbaldehyde Chemical compound CC1=CC=CC=C1NC(N1)=NN=C1SCC1=CC=C(C=O)O1 RFMCIVZPIQKMMO-UHFFFAOYSA-N 0.000 claims description 8
- VPUAEVACUKCMCW-UHFFFAOYSA-N 5-[[5-(3-methylanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carbaldehyde Chemical compound CC1=CC=CC(NC=2NC(SCC=3OC(C=O)=CC=3)=NN=2)=C1 VPUAEVACUKCMCW-UHFFFAOYSA-N 0.000 claims description 8
- USQQHLGLOVLGTK-UHFFFAOYSA-N 5-[[5-(4-fluoroanilino)-1h-1,2,4-triazol-3-yl]sulfanylmethyl]furan-2-carbaldehyde Chemical compound C1=CC(F)=CC=C1NC(N1)=NN=C1SCC1=CC=C(C=O)O1 USQQHLGLOVLGTK-UHFFFAOYSA-N 0.000 claims description 8
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- FBZQIZMRKIHQLV-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methylsulfanyl]-n-(2-phenylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound COC1=CC=CC(CSC=2NN=C(NC=3C(=CC=CC=3)C=3C=CC=CC=3)N=2)=C1 FBZQIZMRKIHQLV-UHFFFAOYSA-N 0.000 claims description 5
- BCCCCILCGLSRGI-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC=2C=CC(F)=CC=2)=N1 BCCCCILCGLSRGI-UHFFFAOYSA-N 0.000 claims description 5
- PPUXAINXZDSWQK-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(OC)=CC=C1CSC1=NC(NC=2C(=CC=CC=2)C(C)C)=NN1 PPUXAINXZDSWQK-UHFFFAOYSA-N 0.000 claims description 5
- ZGSGKKNNZBPUFR-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-n-(2-propan-2-ylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CC(C)C1=CC=CC=C1NC1=NNC(SCC2=NOC(C)=C2)=N1 ZGSGKKNNZBPUFR-UHFFFAOYSA-N 0.000 claims description 5
- OINGZPXMGXQZTC-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound O1C(C)=CC(CSC=2NN=C(NC=3C=CC=CC=3)N=2)=N1 OINGZPXMGXQZTC-UHFFFAOYSA-N 0.000 claims description 5
- ATBNJWRVIFSORI-UHFFFAOYSA-N 3-benzyl-5-benzylsulfanyl-n-phenyl-1,2,4-triazol-3-amine Chemical compound C=1C=CC=CC=1CSC(N=N1)=NC1(NC=1C=CC=CC=1)CC1=CC=CC=C1 ATBNJWRVIFSORI-UHFFFAOYSA-N 0.000 claims description 5
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- BVGOXRXSKKCIMN-UHFFFAOYSA-N 5-benzylsulfanyl-3-methyl-n-phenyl-1,2,4-triazol-3-amine Chemical compound N1=NC(SCC=2C=CC=CC=2)=NC1(C)NC1=CC=CC=C1 BVGOXRXSKKCIMN-UHFFFAOYSA-N 0.000 claims description 5
- AUPSHFREBQUIDS-UHFFFAOYSA-N Cc1cccc(Nc2n[nH]c(Sc3cccs3)n2)c1 Chemical compound Cc1cccc(Nc2n[nH]c(Sc3cccs3)n2)c1 AUPSHFREBQUIDS-UHFFFAOYSA-N 0.000 claims description 5
- ISTWVJVSILOJBB-UHFFFAOYSA-N Cc1ccccc1Nc1n[nH]c(Sc2cccs2)n1 Chemical compound Cc1ccccc1Nc1n[nH]c(Sc2cccs2)n1 ISTWVJVSILOJBB-UHFFFAOYSA-N 0.000 claims description 5
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- 150000001350 alkyl halides Chemical class 0.000 claims description 5
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- CWAAIZHOPULLPV-UHFFFAOYSA-N 3-(5-bromothiophen-2-yl)sulfanyl-n-(4-methylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(SC=2SC(Br)=CC=2)=NN1 CWAAIZHOPULLPV-UHFFFAOYSA-N 0.000 claims 5
- WAXBOCRNJSPCTC-UHFFFAOYSA-N 3-benzylsulfanyl-n-(2-ethylphenyl)-1h-1,2,4-triazol-5-amine Chemical compound CCC1=CC=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 WAXBOCRNJSPCTC-UHFFFAOYSA-N 0.000 claims 5
- OFJZILFQGXSVMM-UHFFFAOYSA-N 3-benzylsulfanyl-n-(3,4-dimethoxyphenyl)-1h-1,2,4-triazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NNC(SCC=2C=CC=CC=2)=N1 OFJZILFQGXSVMM-UHFFFAOYSA-N 0.000 claims 4
- ZTWFBOYRVWAZKD-UHFFFAOYSA-N 3-(2-methylbut-2-enylsulfanyl)-n-phenyl-1h-1,2,4-triazol-5-amine Chemical compound N1C(SCC(C)=CC)=NC(NC=2C=CC=CC=2)=N1 ZTWFBOYRVWAZKD-UHFFFAOYSA-N 0.000 claims 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15728699P | 1999-10-01 | 1999-10-01 | |
| US60/157,286 | 1999-10-01 | ||
| PCT/US2000/026951 WO2001024796A1 (en) | 1999-10-01 | 2000-09-29 | 1,2,4-triazole derivatives, composition, process of making and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003510359A true JP2003510359A (ja) | 2003-03-18 |
| JP2003510359A5 JP2003510359A5 (enExample) | 2007-11-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001527795A Pending JP2003510359A (ja) | 1999-10-01 | 2000-09-29 | 化合物および方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7304082B2 (enExample) |
| EP (1) | EP1223932A4 (enExample) |
| JP (1) | JP2003510359A (enExample) |
| AU (1) | AU7989400A (enExample) |
| WO (1) | WO2001024796A1 (enExample) |
Cited By (3)
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|---|---|---|---|---|
| JP2006503009A (ja) * | 2002-08-09 | 2006-01-26 | アストラゼネカ アクチボラグ | 代謝調節型グルタミン酸受容体−５の調節因子としての１，２，４−オキサジアゾール類 |
| JP2013532660A (ja) * | 2010-07-22 | 2013-08-19 | ザフゲン，インコーポレイテッド | 三環式化合物ならびにその作製および使用方法 |
| JP2017517546A (ja) * | 2014-06-12 | 2017-06-29 | ユニヴェルシテ・ドゥ・リール・２・ドロワ・エ・サンテ | イミダゾール−または１，２，４−トリアゾール−誘導体及びその使用 |
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| WO2002078697A1 (en) * | 2001-03-29 | 2002-10-10 | Smithkline Beecham Corporation | Compounds and methods |
| JP2006504627A (ja) * | 2002-03-27 | 2006-02-09 | スミスクライン・ビーチャム・コーポレイション | 化合物および方法 |
| FR2862060A1 (fr) * | 2003-11-06 | 2005-05-13 | Galderma Res & Dev | Procede de synthese en phase solide de composes de types sulfures de diaryle. |
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| WO2015089800A1 (en) * | 2013-12-19 | 2015-06-25 | Eli Lilly And Company | Fluorophenyl pyrazol compounds |
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| JPS5993063A (ja) * | 1982-09-01 | 1984-05-29 | ビオガル・ジヨジツエルジヤ−ル | アシル化１，２，４−トリアゾ−ル誘導体およびその製造方法 |
| JPS6452763A (en) * | 1980-02-28 | 1989-02-28 | Glaxo Group Ltd | Novel heterocyclic derivative, manufacture and medicinal composition |
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2000
- 2000-09-29 WO PCT/US2000/026951 patent/WO2001024796A1/en not_active Ceased
- 2000-09-29 EP EP00970527A patent/EP1223932A4/en not_active Withdrawn
- 2000-09-29 JP JP2001527795A patent/JP2003510359A/ja active Pending
- 2000-09-29 AU AU79894/00A patent/AU7989400A/en not_active Abandoned
-
2005
- 2005-07-21 US US11/186,519 patent/US7304082B2/en not_active Expired - Fee Related
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| JPS6452763A (en) * | 1980-02-28 | 1989-02-28 | Glaxo Group Ltd | Novel heterocyclic derivative, manufacture and medicinal composition |
| JPS5993063A (ja) * | 1982-09-01 | 1984-05-29 | ビオガル・ジヨジツエルジヤ−ル | アシル化１，２，４−トリアゾ−ル誘導体およびその製造方法 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006503009A (ja) * | 2002-08-09 | 2006-01-26 | アストラゼネカ アクチボラグ | 代謝調節型グルタミン酸受容体−５の調節因子としての１，２，４−オキサジアゾール類 |
| JP2010248214A (ja) * | 2002-08-09 | 2010-11-04 | Astrazeneca Ab | 代謝調節型グルタミン酸受容体−５の調節因子としての１，２，４−オキサジアゾール類 |
| JP2013532660A (ja) * | 2010-07-22 | 2013-08-19 | ザフゲン，インコーポレイテッド | 三環式化合物ならびにその作製および使用方法 |
| JP2017517546A (ja) * | 2014-06-12 | 2017-06-29 | ユニヴェルシテ・ドゥ・リール・２・ドロワ・エ・サンテ | イミダゾール−または１，２，４−トリアゾール−誘導体及びその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1223932A4 (en) | 2003-01-15 |
| AU7989400A (en) | 2001-05-10 |
| US20050267185A1 (en) | 2005-12-01 |
| WO2001024796A1 (en) | 2001-04-12 |
| US7304082B2 (en) | 2007-12-04 |
| WO2001024796A8 (en) | 2001-05-17 |
| EP1223932A1 (en) | 2002-07-24 |
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