JP2003534337A5 - - Google Patents
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- Publication number
- JP2003534337A5 JP2003534337A5 JP2001586279A JP2001586279A JP2003534337A5 JP 2003534337 A5 JP2003534337 A5 JP 2003534337A5 JP 2001586279 A JP2001586279 A JP 2001586279A JP 2001586279 A JP2001586279 A JP 2001586279A JP 2003534337 A5 JP2003534337 A5 JP 2003534337A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thiazol
- chloro
- acetyl
- methylbenzenesulfonamide
- 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.)
- Abandoned
Links
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 150000002431 hydrogen Chemical group 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 5
- -1 4-bromo-5-chloro-2-thienyl Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
- AQRONHMIKZUPDV-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-(4-pentyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CCCCCC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 AQRONHMIKZUPDV-UHFFFAOYSA-N 0.000 description 2
- YONLSQQDISIPRX-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-methyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YONLSQQDISIPRX-UHFFFAOYSA-N 0.000 description 2
- LLKPYCDTFPVDSU-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-methyl-5-propyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=C(CCC)SC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 LLKPYCDTFPVDSU-UHFFFAOYSA-N 0.000 description 2
- ZMOURMHOEOISKY-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-propan-2-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC(C)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 ZMOURMHOEOISKY-UHFFFAOYSA-N 0.000 description 2
- MQKRAYBWXSMTEC-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-propyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 MQKRAYBWXSMTEC-UHFFFAOYSA-N 0.000 description 2
- FKBBDKZYXDJBGC-UHFFFAOYSA-N 3-chloro-n-(4-ethenyl-1,3-thiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=C)=CS1 FKBBDKZYXDJBGC-UHFFFAOYSA-N 0.000 description 2
- ZLIJGGLRZJYQFO-UHFFFAOYSA-N 3-chloro-n-(4-ethyl-1,3-thiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 ZLIJGGLRZJYQFO-UHFFFAOYSA-N 0.000 description 2
- OREQNKNJTKBWIJ-UHFFFAOYSA-N 3-chloro-n-(4-ethyl-5-methyl-1,3-thiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound S1C(C)=C(CC)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C OREQNKNJTKBWIJ-UHFFFAOYSA-N 0.000 description 2
- MNSJVJKRADQCFU-UHFFFAOYSA-N 3-chloro-n-(5-ethyl-4-methyl-1,3-thiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(CC)SC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 MNSJVJKRADQCFU-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- KNKUKOSDOPKXJS-UHFFFAOYSA-N ethyl 2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 KNKUKOSDOPKXJS-UHFFFAOYSA-N 0.000 description 2
- HJDYIOHXQBXMQA-UHFFFAOYSA-N ethyl 2-[(3-chloro-2-methylphenyl)sulfonylamino]-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 HJDYIOHXQBXMQA-UHFFFAOYSA-N 0.000 description 2
- IUOAAYAMNDKEHN-UHFFFAOYSA-N ethyl 3-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-3-methylbutanoate Chemical compound CCOC(=O)CC(C)(C)C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 IUOAAYAMNDKEHN-UHFFFAOYSA-N 0.000 description 2
- KZNGELWLMODZPT-UHFFFAOYSA-N ethyl 4-methyl-2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 KZNGELWLMODZPT-UHFFFAOYSA-N 0.000 description 2
- VVBJTZJDNHUXFS-UHFFFAOYSA-N ethyl 4-methyl-2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 VVBJTZJDNHUXFS-UHFFFAOYSA-N 0.000 description 2
- QQEZVIJOZCZTID-UHFFFAOYSA-N ethyl 4-methyl-2-[(4-propylphenyl)sulfonylamino]-1,3-thiazole-5-carboxylate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C)=C(C(=O)OCC)S1 QQEZVIJOZCZTID-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- RBZGUHWMMJOALQ-UHFFFAOYSA-N n-(4-butyl-1,3-thiazol-2-yl)-3-chloro-2-methylbenzenesulfonamide Chemical compound CCCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 RBZGUHWMMJOALQ-UHFFFAOYSA-N 0.000 description 2
- BPTHAAUNEWLQSY-UHFFFAOYSA-N n-(4-tert-butyl-1,3-thiazol-2-yl)-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C(C)(C)C)=CS1 BPTHAAUNEWLQSY-UHFFFAOYSA-N 0.000 description 2
- CFQCDGGNFHOXTH-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2,4,5-trichlorobenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 CFQCDGGNFHOXTH-UHFFFAOYSA-N 0.000 description 2
- KHQBTIINCMGCHV-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2,4,6-trichlorobenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 KHQBTIINCMGCHV-UHFFFAOYSA-N 0.000 description 2
- UHHBLIGTCQFIQL-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2,4-dichloro-6-methylbenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 UHHBLIGTCQFIQL-UHFFFAOYSA-N 0.000 description 2
- XBFJEUAGXOUBKK-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2,6-dichlorobenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 XBFJEUAGXOUBKK-UHFFFAOYSA-N 0.000 description 2
- HAUBHWUSJGRODE-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-bromo-1,4-difluorocyclohexa-2,4-diene-1-sulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C2(F)C=C(Br)C(F)=CC2)=N1 HAUBHWUSJGRODE-UHFFFAOYSA-N 0.000 description 2
- UJTUJQVBTGZREF-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 UJTUJQVBTGZREF-UHFFFAOYSA-N 0.000 description 2
- QTAPTYOHUUDPKW-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-(3-chloro-2-cyanophenoxy)benzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C=CC(OC=3C(=C(Cl)C=CC=3)C#N)=CC=2)=N1 QTAPTYOHUUDPKW-UHFFFAOYSA-N 0.000 description 2
- ACRDEWAKELMRBD-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-chlorobenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 ACRDEWAKELMRBD-UHFFFAOYSA-N 0.000 description 2
- YMROFWINSIVBQO-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-phenylbenzenesulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 YMROFWINSIVBQO-UHFFFAOYSA-N 0.000 description 2
- SIYKFXOWZBEVSI-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C)=C(C(C)=O)S1 SIYKFXOWZBEVSI-UHFFFAOYSA-N 0.000 description 2
- GFWICMHJJWBKDL-UHFFFAOYSA-N n-(5-butyl-4-methyl-1,3-thiazol-2-yl)-2,4-dichloro-6-methylbenzenesulfonamide Chemical compound CC1=C(CCCC)SC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 GFWICMHJJWBKDL-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- ILVQJNYBERWUIJ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound S1C(CC(Cl)(Cl)Cl)=C(C)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C ILVQJNYBERWUIJ-UHFFFAOYSA-N 0.000 description 1
- XXOYUNQCBYNWNL-UHFFFAOYSA-N 4-chloro-n-(4-methyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 XXOYUNQCBYNWNL-UHFFFAOYSA-N 0.000 description 1
- KBQQNRQRLQSXMB-UHFFFAOYSA-N 4-chloro-n-[4-methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound S1C(CC(Cl)(Cl)Cl)=C(C)N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 KBQQNRQRLQSXMB-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 1
- 201000008980 hyperinsulinism Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- VOVYJLUBJANLEN-UHFFFAOYSA-N n-(4-methyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CSC(NS(=O)(=O)C=2C=CC=CC=2)=N1 VOVYJLUBJANLEN-UHFFFAOYSA-N 0.000 description 1
- KWYMIRMCLAOGGL-UHFFFAOYSA-N n-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-4-bromo-5-chlorothiophene-2-sulfonamide Chemical compound CC1=C(C(=O)C)SC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=N1 KWYMIRMCLAOGGL-UHFFFAOYSA-N 0.000 description 1
- LHALODNUSDEBTM-UHFFFAOYSA-N n-(5-bromo-4-tert-butyl-1,3-thiazol-2-yl)-4-chlorobenzenesulfonamide Chemical compound S1C(Br)=C(C(C)(C)C)N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 LHALODNUSDEBTM-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0001899-4 | 2000-05-22 | ||
| SE0001899A SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | New compounds |
| PCT/SE2001/001156 WO2001090091A1 (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003534337A JP2003534337A (ja) | 2003-11-18 |
| JP2003534337A5 true JP2003534337A5 (enExample) | 2008-05-15 |
Family
ID=20279781
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001586278A Abandoned JP2003534336A (ja) | 2000-05-22 | 2001-05-22 | １１−ベータ−ヒドロキシステロイド・デヒドロゲナーゼタイプ１の阻害因子 |
| JP2001586280A Abandoned JP2003534338A (ja) | 2000-05-22 | 2001-05-22 | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１型の阻害剤 |
| JP2001586279A Abandoned JP2003534337A (ja) | 2000-05-22 | 2001-05-22 | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１型の阻害剤 |
| JP2001586282A Abandoned JP2003534339A (ja) | 2000-05-22 | 2001-05-22 | １１−ベータヒドロキシステロイドデヒドロゲナーゼタイプ１の阻害剤 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001586278A Abandoned JP2003534336A (ja) | 2000-05-22 | 2001-05-22 | １１−ベータ−ヒドロキシステロイド・デヒドロゲナーゼタイプ１の阻害因子 |
| JP2001586280A Abandoned JP2003534338A (ja) | 2000-05-22 | 2001-05-22 | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１型の阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001586282A Abandoned JP2003534339A (ja) | 2000-05-22 | 2001-05-22 | １１−ベータヒドロキシステロイドデヒドロゲナーゼタイプ１の阻害剤 |
Country Status (23)
| Country | Link |
|---|---|
| US (7) | US7125900B2 (enExample) |
| EP (4) | EP1283832B1 (enExample) |
| JP (4) | JP2003534336A (enExample) |
| KR (4) | KR20030011341A (enExample) |
| CN (4) | CN1249039C (enExample) |
| AR (1) | AR033534A1 (enExample) |
| AT (2) | ATE485283T1 (enExample) |
| AU (6) | AU6093201A (enExample) |
| BR (1) | BR0111099A (enExample) |
| CA (4) | CA2409697C (enExample) |
| DE (3) | DE60139931D1 (enExample) |
| EA (1) | EA005274B1 (enExample) |
| ES (1) | ES2333846T3 (enExample) |
| HU (1) | HUP0302435A3 (enExample) |
| IL (4) | IL152670A0 (enExample) |
| MX (1) | MXPA02011632A (enExample) |
| NO (4) | NO323832B1 (enExample) |
| NZ (4) | NZ522506A (enExample) |
| PE (1) | PE20020100A1 (enExample) |
| PL (1) | PL360137A1 (enExample) |
| SE (1) | SE0001899D0 (enExample) |
| WO (5) | WO2001090094A1 (enExample) |
| ZA (4) | ZA200209360B (enExample) |
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