JP2006520330A5 - - Google Patents
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- Publication number
- JP2006520330A5 JP2006520330A5 JP2006504158A JP2006504158A JP2006520330A5 JP 2006520330 A5 JP2006520330 A5 JP 2006520330A5 JP 2006504158 A JP2006504158 A JP 2006504158A JP 2006504158 A JP2006504158 A JP 2006504158A JP 2006520330 A5 JP2006520330 A5 JP 2006520330A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- guanidine
- benzothiazol
- formate salt
- thiazolo
- 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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- 150000004675 formic acid derivatives Chemical class 0.000 claims 42
- -1 arylalkanoyl Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- GYHPCMXILICUER-UHFFFAOYSA-N 2-[4-(aminomethyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound NCC1CCCC2=C1N=C(NC(N)=N)S2 GYHPCMXILICUER-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000007514 bases Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 229940127557 pharmaceutical product Drugs 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000029865 regulation of blood pressure Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- WUUADCHFBLXQKF-UHFFFAOYSA-N 2-(4,4-dimethyl-6,7-dihydro-5h-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1(C)CCCC2=C1N=C(NC(N)=N)S2 WUUADCHFBLXQKF-UHFFFAOYSA-N 0.000 claims 1
- FUGBYHUCJPEPJR-UHFFFAOYSA-N 2-(4-benzyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1CC1=CC=CC=C1 FUGBYHUCJPEPJR-UHFFFAOYSA-N 0.000 claims 1
- NDKWSGBHKXFNCC-UHFFFAOYSA-N 2-(4-butan-2-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CCC(C)C1CCCC2=C1N=C(NC(N)=N)S2 NDKWSGBHKXFNCC-UHFFFAOYSA-N 0.000 claims 1
- QSOMFWDDWOFLBS-UHFFFAOYSA-N 2-(4-ethyl-4-methyl-6,7-dihydro-5h-1,3-benzothiazol-2-yl)guanidine Chemical compound CCC1(C)CCCC2=C1N=C(NC(N)=N)S2 QSOMFWDDWOFLBS-UHFFFAOYSA-N 0.000 claims 1
- OYBQOMBJSHYEAL-UHFFFAOYSA-N 2-(4-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1CCCC2=C1N=C(NC(N)=N)S2 OYBQOMBJSHYEAL-UHFFFAOYSA-N 0.000 claims 1
- LYLYGOUPJRCBLS-UHFFFAOYSA-N 2-(4-methyl-4-propyl-6,7-dihydro-5h-1,3-benzothiazol-2-yl)guanidine Chemical compound CCCC1(C)CCCC2=C1N=C(NC(N)=N)S2 LYLYGOUPJRCBLS-UHFFFAOYSA-N 0.000 claims 1
- BYPPQYJAMBPADG-UHFFFAOYSA-N 2-(4-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C1=CC=CC=C1 BYPPQYJAMBPADG-UHFFFAOYSA-N 0.000 claims 1
- ALIMGROCSLBETQ-UHFFFAOYSA-N 2-(4-tert-butyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CC(C)(C)C1CCCC2=C1N=C(NC(N)=N)S2 ALIMGROCSLBETQ-UHFFFAOYSA-N 0.000 claims 1
- UCXUJAFVTACPGW-UHFFFAOYSA-N 2-(4-tert-butyl-6-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(N)=N)=NC=2C(C(C)(C)C)CC1C1=CC=CC=C1 UCXUJAFVTACPGW-UHFFFAOYSA-N 0.000 claims 1
- QXOFHSUKWFCEBI-UHFFFAOYSA-N 2-(5,5,7,7-tetramethyl-4,6-dihydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1(C)CC(C)(C)CC2=C1SC(NC(N)=N)=N2 QXOFHSUKWFCEBI-UHFFFAOYSA-N 0.000 claims 1
- WLACEDJDTIXJHA-UHFFFAOYSA-N 2-(5,5,7-trimethyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1CC(C)(C)CC2=C1SC(NC(N)=N)=N2 WLACEDJDTIXJHA-UHFFFAOYSA-N 0.000 claims 1
- KLFUHWVGNPXLLK-UHFFFAOYSA-N 2-(5,5-dimethyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C)(C)CCC2=C1N=C(NC(N)=N)S2 KLFUHWVGNPXLLK-UHFFFAOYSA-N 0.000 claims 1
- JVACMLRJYVWKJM-UHFFFAOYSA-N 2-(5,5-dimethyl-6-phenyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1(C)CC=2N=C(NC(N)=N)SC=2CC1C1=CC=CC=C1 JVACMLRJYVWKJM-UHFFFAOYSA-N 0.000 claims 1
- UFTXCRWHCXBQKN-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazol-2-yl)guanidine Chemical compound C1CCCCC2=C1N=C(NC(=N)N)S2 UFTXCRWHCXBQKN-UHFFFAOYSA-N 0.000 claims 1
- UAIBRYGHVVYQBK-UHFFFAOYSA-N 2-(5,6-dihydro-4h-cyclopenta[d][1,3]thiazol-2-yl)guanidine Chemical compound C1CCC2=C1N=C(NC(=N)N)S2 UAIBRYGHVVYQBK-UHFFFAOYSA-N 0.000 claims 1
- FSWGIXWSQKVRBR-UHFFFAOYSA-N 2-(5-benzyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCN1CC1=CC=CC=C1 FSWGIXWSQKVRBR-UHFFFAOYSA-N 0.000 claims 1
- LNXDWHDZNHLNAB-UHFFFAOYSA-N 2-(5-butyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(CCCC)CCC2=C1N=C(NC(N)=N)S2 LNXDWHDZNHLNAB-UHFFFAOYSA-N 0.000 claims 1
- GMABAPWOAXNDDE-UHFFFAOYSA-N 2-(5-butyl-5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazol-2-yl)guanidine Chemical compound C1C(CCCC)CCCC2=C1N=C(NC(N)=N)S2 GMABAPWOAXNDDE-UHFFFAOYSA-N 0.000 claims 1
- UPEQOVLNRJIVEL-UHFFFAOYSA-N 2-(5-butylsulfonyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(S(=O)(=O)CCCC)CCC2=C1SC(NC(N)=N)=N2 UPEQOVLNRJIVEL-UHFFFAOYSA-N 0.000 claims 1
- ZYPREDXHNDNTCV-UHFFFAOYSA-N 2-(5-ethyl-5-methyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(CC)(C)CCC2=C1N=C(NC(N)=N)S2 ZYPREDXHNDNTCV-UHFFFAOYSA-N 0.000 claims 1
- YFOHSVMOPDQBTG-UHFFFAOYSA-N 2-(5-ethyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(CC)CCC2=C1SC(NC(N)=N)=N2 YFOHSVMOPDQBTG-UHFFFAOYSA-N 0.000 claims 1
- DDMZPDGUXYIEAU-UHFFFAOYSA-N 2-(5-hexyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(CCCCCC)CCC2=C1SC(NC(N)=N)=N2 DDMZPDGUXYIEAU-UHFFFAOYSA-N 0.000 claims 1
- RDQBDBMPQLZPSN-UHFFFAOYSA-N 2-(5-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C)CCC2=C1N=C(NC(N)=N)S2 RDQBDBMPQLZPSN-UHFFFAOYSA-N 0.000 claims 1
- ICDGFGKAIBXUJJ-UHFFFAOYSA-N 2-(5-methyl-5-phenyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1CC=2SC(NC(N)=N)=NC=2CC1(C)C1=CC=CC=C1 ICDGFGKAIBXUJJ-UHFFFAOYSA-N 0.000 claims 1
- RHNOCHLHOYFGLC-UHFFFAOYSA-N 2-(5-methylsulfonyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(S(=O)(=O)C)CCC2=C1SC(NC(N)=N)=N2 RHNOCHLHOYFGLC-UHFFFAOYSA-N 0.000 claims 1
- BQTZVYKQEGHYIG-UHFFFAOYSA-N 2-(5-pentanoyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(C(=O)CCCC)CCC2=C1SC(NC(N)=N)=N2 BQTZVYKQEGHYIG-UHFFFAOYSA-N 0.000 claims 1
- AOCYGZXXCPMOJM-UHFFFAOYSA-N 2-(5-phenyl-5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazol-2-yl)guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2CC1C1=CC=CC=C1 AOCYGZXXCPMOJM-UHFFFAOYSA-N 0.000 claims 1
- JWSONFTVEHCGJQ-UHFFFAOYSA-N 2-(5-propan-2-ylsulfonyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(S(=O)(=O)C(C)C)CCC2=C1SC(NC(N)=N)=N2 JWSONFTVEHCGJQ-UHFFFAOYSA-N 0.000 claims 1
- FBUBOFVNIZACRW-UHFFFAOYSA-N 2-(5-propyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(CCC)CCC2=C1SC(NC(N)=N)=N2 FBUBOFVNIZACRW-UHFFFAOYSA-N 0.000 claims 1
- AKOBTVQNQFUIFL-UHFFFAOYSA-N 2-(6,6-dimethyl-5,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C)(C)CCC2=C1SC(NC(N)=N)=N2 AKOBTVQNQFUIFL-UHFFFAOYSA-N 0.000 claims 1
- WVXCYAIRSGWGBV-UHFFFAOYSA-N 2-(6,6-diphenyl-5,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 WVXCYAIRSGWGBV-UHFFFAOYSA-N 0.000 claims 1
- CYXYEESUXIALNC-UHFFFAOYSA-N 2-(6,7-dihydro-4h-pyrano[4,3-d][1,3]thiazol-2-yl)guanidine Chemical compound C1COCC2=C1N=C(NC(=N)N)S2 CYXYEESUXIALNC-UHFFFAOYSA-N 0.000 claims 1
- MCCUUZYXCGYWIN-UHFFFAOYSA-N 2-(6-cyano-6-phenyl-5,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCC1(C#N)C1=CC=CC=C1 MCCUUZYXCGYWIN-UHFFFAOYSA-N 0.000 claims 1
- GUWOIUDVUADBQM-UHFFFAOYSA-N 2-(6-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C)CCC2=C1SC(NC(N)=N)=N2 GUWOIUDVUADBQM-UHFFFAOYSA-N 0.000 claims 1
- WPRMMSUIODPDQQ-UHFFFAOYSA-N 2-(6-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCC1C1=CC=CC=C1 WPRMMSUIODPDQQ-UHFFFAOYSA-N 0.000 claims 1
- QDOXNVJQBUENNN-UHFFFAOYSA-N 2-(6-propan-2-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C(C)C)CCC2=C1SC(NC(N)=N)=N2 QDOXNVJQBUENNN-UHFFFAOYSA-N 0.000 claims 1
- GGSJEFBOSRYGBZ-UHFFFAOYSA-N 2-(6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(CCC)CCC2=C1SC(NC(N)=N)=N2 GGSJEFBOSRYGBZ-UHFFFAOYSA-N 0.000 claims 1
- RFZXGFBVQUEHCE-UHFFFAOYSA-N 2-(6-tert-butyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C(C)(C)C)CCC2=C1SC(NC(N)=N)=N2 RFZXGFBVQUEHCE-UHFFFAOYSA-N 0.000 claims 1
- XHPLIMKFVJUFOQ-UHFFFAOYSA-N 2-(6-thiophen-2-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCC1C1=CC=CS1 XHPLIMKFVJUFOQ-UHFFFAOYSA-N 0.000 claims 1
- WVIAKQLSKCZTNT-UHFFFAOYSA-N 2-(7-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1CCCC2=C1SC(NC(N)=N)=N2 WVIAKQLSKCZTNT-UHFFFAOYSA-N 0.000 claims 1
- UELDUEAYRHAPRG-UHFFFAOYSA-N 2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxylic acid Chemical compound OC(=O)C1CCCC2=C1N=C(NC(=N)N)S2 UELDUEAYRHAPRG-UHFFFAOYSA-N 0.000 claims 1
- IQSJJHUZFHAQCL-UHFFFAOYSA-N 2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1CC(C(O)=O)CC2=C1N=C(NC(=N)N)S2 IQSJJHUZFHAQCL-UHFFFAOYSA-N 0.000 claims 1
- LTLRBTVKAFNNIM-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n,n-di(propan-2-yl)-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound CC(C)N(C(C)C)C(=O)C1CCCC2=C1N=C(NC(N)=N)S2 LTLRBTVKAFNNIM-UHFFFAOYSA-N 0.000 claims 1
- VSXRAZUNVFIEQE-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n,n-dipropyl-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound CCCN(CCC)C(=O)C1CCCC2=C1N=C(NC(N)=N)S2 VSXRAZUNVFIEQE-UHFFFAOYSA-N 0.000 claims 1
- GOJROTMNJNWGMG-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-(1-methoxypropan-2-yl)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NC(C)COC)CCC2=C1SC(NC(N)=N)=N2 GOJROTMNJNWGMG-UHFFFAOYSA-N 0.000 claims 1
- UYKORIYFERXQTN-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-(3-methylbutyl)-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound CC(C)CCNC(=O)C1CCCC2=C1N=C(NC(N)=N)S2 UYKORIYFERXQTN-UHFFFAOYSA-N 0.000 claims 1
- SLQUKKCTGQRJSM-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-(3-methylbutyl)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxamide Chemical compound C1C(C(=O)NCCC(C)C)CCC2=C1SC(NC(N)=N)=N2 SLQUKKCTGQRJSM-UHFFFAOYSA-N 0.000 claims 1
- POANLTXZHXLSIR-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-methyl-n-(2-phenylethyl)-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound C1CCC=2SC(N=C(N)N)=NC=2C1C(=O)N(C)CCC1=CC=CC=C1 POANLTXZHXLSIR-UHFFFAOYSA-N 0.000 claims 1
- YHBVQQYSGAVNFE-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-pentyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carboxamide Chemical compound C1N(C(=O)NCCCCC)CCC2=C1SC(NC(N)=N)=N2 YHBVQQYSGAVNFE-UHFFFAOYSA-N 0.000 claims 1
- ALIKGSQZHJPGOJ-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C(=O)NC1=CC=CC=C1 ALIKGSQZHJPGOJ-UHFFFAOYSA-N 0.000 claims 1
- QMAOJYKWYMFLDP-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxamide Chemical compound C1C=2SC(NC(=N)N)=NC=2CCC1C(=O)NC1=CC=CC=C1 QMAOJYKWYMFLDP-UHFFFAOYSA-N 0.000 claims 1
- QJHYMDXVSYZIDQ-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-phenyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carboxamide Chemical compound C1C=2SC(NC(=N)N)=NC=2CCN1C(=O)NC1=CC=CC=C1 QJHYMDXVSYZIDQ-UHFFFAOYSA-N 0.000 claims 1
- ZCBZWGQVGHFAOB-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-propan-2-yl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NC(C)C)CCC2=C1SC(N=C(N)N)=N2 ZCBZWGQVGHFAOB-UHFFFAOYSA-N 0.000 claims 1
- VMNCXUGRHQUZEF-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound CCCNC(=O)C1CCCC2=C1N=C(NC(N)=N)S2 VMNCXUGRHQUZEF-UHFFFAOYSA-N 0.000 claims 1
- QWHJPAKVYVBKFQ-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxamide Chemical compound C1C(C(=O)NCCC)CCC2=C1SC(NC(N)=N)=N2 QWHJPAKVYVBKFQ-UHFFFAOYSA-N 0.000 claims 1
- YAJZFNWYKDVSPN-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-propyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NCCC)CCC2=C1SC(NC(N)=N)=N2 YAJZFNWYKDVSPN-UHFFFAOYSA-N 0.000 claims 1
- OLDBFYAXTHRQGT-UHFFFAOYSA-N 2-[4-(2-cyanoethyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound N#CCCC1CCCC2=C1N=C(NC(=N)N)S2 OLDBFYAXTHRQGT-UHFFFAOYSA-N 0.000 claims 1
- PGEHXVOYKVRYKK-UHFFFAOYSA-N 2-[4-(morpholine-4-carbonyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C(=O)N1CCOCC1 PGEHXVOYKVRYKK-UHFFFAOYSA-N 0.000 claims 1
- QBAXFGDLEDRYCD-UHFFFAOYSA-N 2-[4-(piperidine-1-carbonyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C(=O)N1CCCCC1 QBAXFGDLEDRYCD-UHFFFAOYSA-N 0.000 claims 1
- KUORHFIBNWNBCM-UHFFFAOYSA-N 2-[4-methyl-4-(2-methylpropyl)-6,7-dihydro-5h-1,3-benzothiazol-2-yl]guanidine Chemical compound CC(C)CC1(C)CCCC2=C1N=C(NC(N)=N)S2 KUORHFIBNWNBCM-UHFFFAOYSA-N 0.000 claims 1
- DGPJUHKVGVAYFQ-UHFFFAOYSA-N 2-[5-(2,2-dimethylpropanoyl)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl]guanidine Chemical compound C1N(C(=O)C(C)(C)C)CCC2=C1SC(NC(N)=N)=N2 DGPJUHKVGVAYFQ-UHFFFAOYSA-N 0.000 claims 1
- GKIINEKRXYIBOE-UHFFFAOYSA-N 2-[5-(2-cyclohexylethyl)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl]guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCN1CCC1CCCCC1 GKIINEKRXYIBOE-UHFFFAOYSA-N 0.000 claims 1
- BPPIBKABLSGTFE-UHFFFAOYSA-N 2-[5-(2-methoxyacetyl)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl]guanidine Chemical compound C1N(C(=O)COC)CCC2=C1SC(NC(N)=N)=N2 BPPIBKABLSGTFE-UHFFFAOYSA-N 0.000 claims 1
- RCNHNMAWLLOAOJ-UHFFFAOYSA-N 2-[5-(2-methylpropanoyl)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl]guanidine Chemical compound C1N(C(=O)C(C)C)CCC2=C1SC(NC(N)=N)=N2 RCNHNMAWLLOAOJ-UHFFFAOYSA-N 0.000 claims 1
- MYUICDHWHUMZEA-UHFFFAOYSA-N 2-[5-(2-phenylacetyl)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl]guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCN1C(=O)CC1=CC=CC=C1 MYUICDHWHUMZEA-UHFFFAOYSA-N 0.000 claims 1
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| CL2004000553A1 (es) | 2003-03-20 | 2005-02-04 | Actelion Pharmaceuticals Ltd | Uso de compuestos derivados de guanidina como antagonistas del receptor de neuropeptido ff; compuestos derivados de guanidina; procedimientos de preparacion; y composicion farmaceutica que los comprende. |
| CA2560128A1 (en) * | 2004-03-19 | 2005-10-06 | Dipharma S.P.A. | Intermediates for the preparation of pramipexole |
| JP2009543785A (ja) | 2006-07-14 | 2009-12-10 | メルク エンド カムパニー インコーポレーテッド | 架橋ジアゼパンオレキシン受容体アンタゴニスト |
| PE20081229A1 (es) | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
| JP2010527924A (ja) | 2007-05-18 | 2010-08-19 | メルク・シャープ・エンド・ドーム・コーポレイション | オキソ架橋ジアゼパンオレキシン受容体アンタゴニスト |
| US8030495B2 (en) | 2007-05-23 | 2011-10-04 | Coleman Paul J | Cyclopropyl pyrrolidine orexin receptor antagonists |
| ES2379744T3 (es) | 2007-05-23 | 2012-05-03 | Merck Sharp & Dohme Corp. | Antagonistas de piridil-piperidina de los receptores de orexinas |
| US8410284B2 (en) | 2008-10-22 | 2013-04-02 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US8329914B2 (en) | 2008-10-31 | 2012-12-11 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| PH12013501686A1 (en) | 2011-02-25 | 2017-10-25 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
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| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
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| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
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| EP3762008A1 (en) * | 2018-03-09 | 2021-01-13 | Centre National de la Recherche Scientifique | Hybrid mu opioid receptor and neuropeptide ff receptor binding molecules, their methods of preparation and applications in therapeutic treatment |
| CN110093348B (zh) * | 2018-12-05 | 2022-11-29 | 西北工业大学 | 增强小鼠NPFFR2基因表达的shRNA |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1620508A1 (de) * | 1965-07-23 | 1969-09-18 | Thomae Gmbh Dr K | Verfahren zur Herstellung neuer 4,5,6,7-Tetrahydrothiazolo-[5,4-c]-pyridine |
| BE795257A (fr) | 1972-02-10 | 1973-08-09 | Thomae Gmbh Dr K | Nouveaux oxazols |
| SU664965A1 (ru) * | 1977-02-01 | 1979-05-30 | Уральский ордена Трудового Красного Знамени политехнический институт им.С.М.Кирова | 3-Замещенные пиридо /2,3-е/-1,2,4тиадиазин-1,1-диоксиды,обладающие анальгетическим действием |
| GB8333514D0 (en) * | 1983-12-16 | 1984-01-25 | Erba Farmitalia | Tetrahydrothiazolo(5 4-c)pyridine derivatives |
| JPS60226810A (ja) | 1984-04-25 | 1985-11-12 | Ikeda Mohandou:Kk | 抗潰瘍剤 |
| GB2173187B (en) * | 1985-03-23 | 1988-05-18 | Erba Farmitalia | Condensed 2-substituted thiazole derivatives |
| JPS6233158A (ja) | 1985-08-02 | 1987-02-13 | Shionogi & Co Ltd | ベンズイミダゾ−ル誘導体および抗潰瘍剤 |
| WO1989005643A1 (en) | 1987-12-18 | 1989-06-29 | Pfizer Inc. | Heterocyclic-substituted quinoline-carboxylic acids |
| KR0168978B1 (ko) * | 1995-07-12 | 1999-01-15 | 김종인 | 헤테로고리 접합 티아졸 유도체 |
| JPH0959258A (ja) * | 1995-08-11 | 1997-03-04 | Ono Pharmaceut Co Ltd | グアニジル誘導体 |
| FR2814367B1 (fr) | 2000-09-25 | 2008-12-26 | Inst Nat Sante Rech Med | Ligands du recepteur npff pour le traitement de la douleur et des hyperalgies |
| CL2004000553A1 (es) | 2003-03-20 | 2005-02-04 | Actelion Pharmaceuticals Ltd | Uso de compuestos derivados de guanidina como antagonistas del receptor de neuropeptido ff; compuestos derivados de guanidina; procedimientos de preparacion; y composicion farmaceutica que los comprende. |
-
2004
- 2004-03-17 CL CL200400553A patent/CL2004000553A1/es unknown
- 2004-03-19 TW TW093107426A patent/TW200510434A/zh unknown
- 2004-03-19 AR ARP040100923A patent/AR043662A1/es unknown
- 2004-03-22 JP JP2006504158A patent/JP2006520330A/ja active Pending
- 2004-03-22 CA CA002518679A patent/CA2518679A1/en not_active Abandoned
- 2004-03-22 KR KR1020057016769A patent/KR20050107611A/ko not_active Withdrawn
- 2004-03-22 WO PCT/CH2004/000175 patent/WO2004083218A1/de not_active Ceased
- 2004-03-22 BR BRPI0408357-1A patent/BRPI0408357A/pt not_active IP Right Cessation
- 2004-03-22 EP EP04722212A patent/EP1608662A1/de not_active Withdrawn
- 2004-03-22 CN CNB2004800074476A patent/CN100355758C/zh not_active Expired - Fee Related
- 2004-03-22 MX MXPA05009855A patent/MXPA05009855A/es unknown
- 2004-03-22 AU AU2004222224A patent/AU2004222224A1/en not_active Abandoned
- 2004-03-22 US US10/549,685 patent/US7727979B2/en not_active Expired - Fee Related
- 2004-03-22 RU RU2005132308/04A patent/RU2337911C2/ru not_active IP Right Cessation
-
2005
- 2005-10-14 NO NO20054743A patent/NO20054743L/no unknown
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