KR20060023570A - 새로운 용도 ｉ - Google Patents
새로운 용도 ｉ Download PDFInfo
- Publication number
- KR20060023570A KR20060023570A KR1020057024626A KR20057024626A KR20060023570A KR 20060023570 A KR20060023570 A KR 20060023570A KR 1020057024626 A KR1020057024626 A KR 1020057024626A KR 20057024626 A KR20057024626 A KR 20057024626A KR 20060023570 A KR20060023570 A KR 20060023570A
- Authority
- KR
- South Korea
- Prior art keywords
- thiazol
- ethyl
- amino
- sulfonyl
- chloro
- 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.)
- Withdrawn
Links
- 230000029663 wound healing Effects 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000003112 inhibitor Substances 0.000 claims abstract description 16
- 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 claims abstract description 12
- 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 10
- 230000001737 promoting effect Effects 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 229940079593 drug Drugs 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000002243 precursor Substances 0.000 claims abstract description 4
- 241000124008 Mammalia Species 0.000 claims abstract description 3
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 3
- 150000004677 hydrates Chemical class 0.000 claims abstract description 3
- 230000003287 optical effect Effects 0.000 claims abstract description 3
- 239000012453 solvate Substances 0.000 claims abstract description 3
- 101710088194 Dehydrogenase Proteins 0.000 claims abstract 2
- -1 (Benzoylamino) methyl Chemical class 0.000 claims description 281
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 71
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 206010052428 Wound Diseases 0.000 claims description 22
- 208000027418 Wounds and injury Diseases 0.000 claims description 22
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000003862 glucocorticoid Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 229940037128 systemic glucocorticoids Drugs 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 230000003111 delayed effect Effects 0.000 claims description 8
- 230000001771 impaired effect Effects 0.000 claims description 8
- YDPRNGAPPNPYQQ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YDPRNGAPPNPYQQ-UHFFFAOYSA-N 0.000 claims description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 206010056340 Diabetic ulcer Diseases 0.000 claims description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- 206010040943 Skin Ulcer Diseases 0.000 claims description 4
- 208000000558 Varicose Ulcer Diseases 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical class 0.000 claims description 4
- 125000004104 aryloxy group Chemical class 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 231100000019 skin ulcer Toxicity 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- CGPRKKGTHPOISW-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 CGPRKKGTHPOISW-UHFFFAOYSA-N 0.000 claims description 2
- OCKUKOAKTSTSHL-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 OCKUKOAKTSTSHL-UHFFFAOYSA-N 0.000 claims description 2
- JZBMRTMNGYNDHZ-UHFFFAOYSA-N 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 JZBMRTMNGYNDHZ-UHFFFAOYSA-N 0.000 claims description 2
- WSKHSWHWEKUKCK-UHFFFAOYSA-N 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 WSKHSWHWEKUKCK-UHFFFAOYSA-N 0.000 claims description 2
- JBKXGULGNQEDPS-UHFFFAOYSA-N 2-[2-[(2,4-difluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethylacetamide Chemical compound CCNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)F)=N1 JBKXGULGNQEDPS-UHFFFAOYSA-N 0.000 claims description 2
- WYWISWQMNVHCCM-UHFFFAOYSA-N 2-[2-[(2,5-dichlorothiophen-3-yl)sulfonylamino]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CSC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=N1 WYWISWQMNVHCCM-UHFFFAOYSA-N 0.000 claims description 2
- HEMVPFSRVDOYIS-UHFFFAOYSA-N 2-[2-[(2,5-dichlorothiophen-3-yl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=N1 HEMVPFSRVDOYIS-UHFFFAOYSA-N 0.000 claims description 2
- AJWZZHZNTINJCH-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 AJWZZHZNTINJCH-UHFFFAOYSA-N 0.000 claims description 2
- PNFMZAHWOASGJC-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 PNFMZAHWOASGJC-UHFFFAOYSA-N 0.000 claims description 2
- RVGOYEWLPWEFCI-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 RVGOYEWLPWEFCI-UHFFFAOYSA-N 0.000 claims description 2
- HCVDPOLLLJHUPC-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 HCVDPOLLLJHUPC-UHFFFAOYSA-N 0.000 claims description 2
- ZFZSPBPBECULLJ-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-phenylacetamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)NC=2C=CC=CC=2)=CS1 ZFZSPBPBECULLJ-UHFFFAOYSA-N 0.000 claims description 2
- SQGWOBDUXQBFJO-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)=O)=CS1 SQGWOBDUXQBFJO-UHFFFAOYSA-N 0.000 claims description 2
- VYZWVMVWGHXNGP-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl methanesulfonate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOS(C)(=O)=O)=CS1 VYZWVMVWGHXNGP-UHFFFAOYSA-N 0.000 claims description 2
- VISGQGQJQWSXHJ-UHFFFAOYSA-N 2-[2-[(4-acetamidophenyl)sulfonylamino]-4-thiazolyl]acetic acid ethyl ester Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)=N1 VISGQGQJQWSXHJ-UHFFFAOYSA-N 0.000 claims description 2
- KIYPUUWMSLECQJ-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-(furan-2-ylmethyl)acetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)NCC=2OC=CC=2)=CS1 KIYPUUWMSLECQJ-UHFFFAOYSA-N 0.000 claims description 2
- AYKJIFPXBJZYOI-UHFFFAOYSA-N 2-[2-[(4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(CC(O)=O)=CS1 AYKJIFPXBJZYOI-UHFFFAOYSA-N 0.000 claims description 2
- OEUIPTZTKZPHFU-UHFFFAOYSA-N 2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 OEUIPTZTKZPHFU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- LRSHRBXCWRJSCQ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-oxopentyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCCC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 LRSHRBXCWRJSCQ-UHFFFAOYSA-N 0.000 claims description 2
- PCURMNYHJKIXIK-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-phenylmethoxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOCC=2C=CC=CC=2)=CS1 PCURMNYHJKIXIK-UHFFFAOYSA-N 0.000 claims description 2
- RJBYZNYPFAZOTP-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-propan-2-yloxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC(C)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 RJBYZNYPFAZOTP-UHFFFAOYSA-N 0.000 claims description 2
- FCZLQYWUZTVEES-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[(3-oxomorpholin-4-yl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CN2C(COCC2)=O)=CS1 FCZLQYWUZTVEES-UHFFFAOYSA-N 0.000 claims description 2
- UZLWJPBUKCZYIM-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(2,2,2-trifluoroethoxy)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOCC(F)(F)F)=CS1 UZLWJPBUKCZYIM-UHFFFAOYSA-N 0.000 claims description 2
- UZWQRKFUNIGEEO-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(trifluoromethylsulfonylamino)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNS(=O)(=O)C(F)(F)F)=CS1 UZWQRKFUNIGEEO-UHFFFAOYSA-N 0.000 claims description 2
- WPQLIXHVJMZDCD-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[3-(3-oxomorpholin-4-yl)propyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCN2C(COCC2)=O)=CS1 WPQLIXHVJMZDCD-UHFFFAOYSA-N 0.000 claims description 2
- XNIJTLZWWZHATQ-UHFFFAOYSA-N 3-chloro-n-[4-(2-chloroethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCl)=CS1 XNIJTLZWWZHATQ-UHFFFAOYSA-N 0.000 claims description 2
- PMDHDRBKLSNVTO-UHFFFAOYSA-N 3-chloro-n-[4-(2-ethoxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCOCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 PMDHDRBKLSNVTO-UHFFFAOYSA-N 0.000 claims description 2
- PSIMSLBVQXNOEQ-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCO)=CS1 PSIMSLBVQXNOEQ-UHFFFAOYSA-N 0.000 claims description 2
- UQAMHSFHVDZYEN-UHFFFAOYSA-N 3-chloro-n-[4-(2-imidazol-1-ylethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2C=NC=C2)=CS1 UQAMHSFHVDZYEN-UHFFFAOYSA-N 0.000 claims description 2
- JOVCZOADHRKCLI-UHFFFAOYSA-N 3-chloro-n-[4-(2-methoxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound COCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 JOVCZOADHRKCLI-UHFFFAOYSA-N 0.000 claims description 2
- MQNNPMUEUFLKRU-UHFFFAOYSA-N 3-chloro-n-[4-[2-(2-fluoroethoxy)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOCCF)=CS1 MQNNPMUEUFLKRU-UHFFFAOYSA-N 0.000 claims description 2
- IBCZFVVJSBMGBI-UHFFFAOYSA-N 3-chloro-n-[4-[2-(2-hydroxyethylamino)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNCCO)=CS1 IBCZFVVJSBMGBI-UHFFFAOYSA-N 0.000 claims description 2
- GDULMDVSHSQBBG-UHFFFAOYSA-N 3-chloro-n-[4-[2-(diethylamino)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.CCN(CC)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GDULMDVSHSQBBG-UHFFFAOYSA-N 0.000 claims description 2
- GVEMPLKGNIFWOE-UHFFFAOYSA-N 3-chloro-n-[4-[2-(ethylamino)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCNCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GVEMPLKGNIFWOE-UHFFFAOYSA-N 0.000 claims description 2
- DZOVJGIRFXTALH-UHFFFAOYSA-N 4,5-dichloro-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound S1C(Cl)=C(Cl)C=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 DZOVJGIRFXTALH-UHFFFAOYSA-N 0.000 claims description 2
- NOLMXNHBTMCQLS-UHFFFAOYSA-N 4-chloro-n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound OCCC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 NOLMXNHBTMCQLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001769 aryl amino group Chemical class 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- IJNMHHJKXLKFJT-UHFFFAOYSA-N ethyl 2-[2-(benzenesulfonamido)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC=CC=2)=N1 IJNMHHJKXLKFJT-UHFFFAOYSA-N 0.000 claims description 2
- JJWLUBGKRMKXNK-UHFFFAOYSA-N ethyl 2-[2-(naphthalen-2-ylsulfonylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=N1 JJWLUBGKRMKXNK-UHFFFAOYSA-N 0.000 claims description 2
- JVAFXOOYGZUHAM-UHFFFAOYSA-N ethyl 2-[2-(quinolin-8-ylsulfonylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)=N1 JVAFXOOYGZUHAM-UHFFFAOYSA-N 0.000 claims description 2
- CAAGINURIJZJFA-UHFFFAOYSA-N ethyl 2-[2-[(1-methylimidazol-4-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2N=CN(C)C=2)=N1 CAAGINURIJZJFA-UHFFFAOYSA-N 0.000 claims description 2
- AYEZJMCEEUOZBO-UHFFFAOYSA-N ethyl 2-[2-[(2,3,4-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C(Cl)=CC=2)Cl)=N1 AYEZJMCEEUOZBO-UHFFFAOYSA-N 0.000 claims description 2
- CBVGFYLRKFMWIY-UHFFFAOYSA-N ethyl 2-[2-[(2,3-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=N1 CBVGFYLRKFMWIY-UHFFFAOYSA-N 0.000 claims description 2
- DFPIHKZQUYAUSJ-UHFFFAOYSA-N ethyl 2-[2-[(2,4,5-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 DFPIHKZQUYAUSJ-UHFFFAOYSA-N 0.000 claims description 2
- YVDPHJVUTMGFBK-UHFFFAOYSA-N ethyl 2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 YVDPHJVUTMGFBK-UHFFFAOYSA-N 0.000 claims description 2
- XTSPBSIOOVDLFL-UHFFFAOYSA-N ethyl 2-[2-[(2,4,6-trifluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2F)F)=N1 XTSPBSIOOVDLFL-UHFFFAOYSA-N 0.000 claims description 2
- RXLDVKZBTUCMEB-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 RXLDVKZBTUCMEB-UHFFFAOYSA-N 0.000 claims description 2
- AZFIPTGNCDPGCH-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)Cl)=N1 AZFIPTGNCDPGCH-UHFFFAOYSA-N 0.000 claims description 2
- KACQGQGBDKICBL-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)=N1 KACQGQGBDKICBL-UHFFFAOYSA-N 0.000 claims description 2
- FCKASCFOIWCCQJ-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dimethoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(OC)C=2)OC)=N1 FCKASCFOIWCCQJ-UHFFFAOYSA-N 0.000 claims description 2
- FUOFZFZFISSASM-UHFFFAOYSA-N ethyl 2-[2-[(2,6-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 FUOFZFZFISSASM-UHFFFAOYSA-N 0.000 claims description 2
- IQHJPEZHJFMMKA-UHFFFAOYSA-N ethyl 2-[2-[(2-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Br)=N1 IQHJPEZHJFMMKA-UHFFFAOYSA-N 0.000 claims description 2
- FIUOJUMQXLUVOT-UHFFFAOYSA-N ethyl 2-[2-[(2-chloro-4-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)Cl)=N1 FIUOJUMQXLUVOT-UHFFFAOYSA-N 0.000 claims description 2
- JDBWRECUZVWGNO-UHFFFAOYSA-N ethyl 2-[2-[(2-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 JDBWRECUZVWGNO-UHFFFAOYSA-N 0.000 claims description 2
- HAGXVJTVTTUNAP-UHFFFAOYSA-N ethyl 2-[2-[(2-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)C#N)=N1 HAGXVJTVTTUNAP-UHFFFAOYSA-N 0.000 claims description 2
- PMRYJIFBBGSVKP-UHFFFAOYSA-N ethyl 2-[2-[(2-methoxy-4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(C)=CC=2)OC)=N1 PMRYJIFBBGSVKP-UHFFFAOYSA-N 0.000 claims description 2
- ZCNWUMGMIAXUQD-UHFFFAOYSA-N ethyl 2-[2-[(2-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 ZCNWUMGMIAXUQD-UHFFFAOYSA-N 0.000 claims description 2
- HLIXWSCWOHFWJI-UHFFFAOYSA-N ethyl 2-[2-[(3,4-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 HLIXWSCWOHFWJI-UHFFFAOYSA-N 0.000 claims description 2
- XJVXNSMNVRSDPC-UHFFFAOYSA-N ethyl 2-[2-[(3,5-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=N1 XJVXNSMNVRSDPC-UHFFFAOYSA-N 0.000 claims description 2
- PDEKOPUOMNHLQP-UHFFFAOYSA-N ethyl 2-[2-[(3-bromo-5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C2=C(C=C(Cl)S2)Br)=N1 PDEKOPUOMNHLQP-UHFFFAOYSA-N 0.000 claims description 2
- ZTCSTONMUHDFKJ-UHFFFAOYSA-N ethyl 2-[2-[(3-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Br)C=CC=2)=N1 ZTCSTONMUHDFKJ-UHFFFAOYSA-N 0.000 claims description 2
- GZLJHVLKSZQICO-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GZLJHVLKSZQICO-UHFFFAOYSA-N 0.000 claims description 2
- WYLIDXHKCNSRSG-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WYLIDXHKCNSRSG-UHFFFAOYSA-N 0.000 claims description 2
- ANVGCTSGCSBOTQ-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(C)=CC=2)=N1 ANVGCTSGCSBOTQ-UHFFFAOYSA-N 0.000 claims description 2
- YTRIEVDHWCSHLN-UHFFFAOYSA-N ethyl 2-[2-[(3-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=N1 YTRIEVDHWCSHLN-UHFFFAOYSA-N 0.000 claims description 2
- WDZSIANQAZTVEH-UHFFFAOYSA-N ethyl 2-[2-[(3-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)C#N)=N1 WDZSIANQAZTVEH-UHFFFAOYSA-N 0.000 claims description 2
- BOFWWAXNVWTGKH-UHFFFAOYSA-N ethyl 2-[2-[(3-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(F)C=CC=2)=N1 BOFWWAXNVWTGKH-UHFFFAOYSA-N 0.000 claims description 2
- PZARFSJHMREGLA-UHFFFAOYSA-N ethyl 2-[2-[(3-methoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(OC)C=CC=2)=N1 PZARFSJHMREGLA-UHFFFAOYSA-N 0.000 claims description 2
- WZQBUAOAZRGEBW-UHFFFAOYSA-N ethyl 2-[2-[(3-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C)C=CC=2)=N1 WZQBUAOAZRGEBW-UHFFFAOYSA-N 0.000 claims description 2
- GIDZENNFVLMYKK-UHFFFAOYSA-N ethyl 2-[2-[(3-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=N1 GIDZENNFVLMYKK-UHFFFAOYSA-N 0.000 claims description 2
- JWPFFPNIEBVQBS-UHFFFAOYSA-N ethyl 2-[2-[(4,5-dichlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=N1 JWPFFPNIEBVQBS-UHFFFAOYSA-N 0.000 claims description 2
- UHAQMGZZUVKJHH-UHFFFAOYSA-N ethyl 2-[2-[(4-acetamido-3-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(NC(C)=O)=CC=2)=N1 UHAQMGZZUVKJHH-UHFFFAOYSA-N 0.000 claims description 2
- XQETZYRGNIDJBQ-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)F)=N1 XQETZYRGNIDJBQ-UHFFFAOYSA-N 0.000 claims description 2
- CWRLDLCBUSKDDE-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)C)=N1 CWRLDLCBUSKDDE-UHFFFAOYSA-N 0.000 claims description 2
- GJLYEXVGTDRIDB-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=N1 GJLYEXVGTDRIDB-UHFFFAOYSA-N 0.000 claims description 2
- PGUXTMPTPRTMHK-UHFFFAOYSA-N ethyl 2-[2-[(4-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(Br)=CC=2)=N1 PGUXTMPTPRTMHK-UHFFFAOYSA-N 0.000 claims description 2
- KKXBMETYIBLJLL-UHFFFAOYSA-N ethyl 2-[2-[(4-butoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OCC)=CS1 KKXBMETYIBLJLL-UHFFFAOYSA-N 0.000 claims description 2
- OAGJLQCJTUZHMJ-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2,6-dimethylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)C)=N1 OAGJLQCJTUZHMJ-UHFFFAOYSA-N 0.000 claims description 2
- AAWVIKWDCOANTH-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)C)=N1 AAWVIKWDCOANTH-UHFFFAOYSA-N 0.000 claims description 2
- IITATKCUYSUFMF-UHFFFAOYSA-N ethyl 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 IITATKCUYSUFMF-UHFFFAOYSA-N 0.000 claims description 2
- MSBRGTIONVCFPM-UHFFFAOYSA-N ethyl 2-[2-[(4-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C#N)=N1 MSBRGTIONVCFPM-UHFFFAOYSA-N 0.000 claims description 2
- IUMBUSOAXLMIQO-UHFFFAOYSA-N ethyl 2-[2-[(4-iodophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(I)=CC=2)=N1 IUMBUSOAXLMIQO-UHFFFAOYSA-N 0.000 claims description 2
- UZBKVHNVGKVIBK-UHFFFAOYSA-N ethyl 2-[2-[(4-methoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC)=CC=2)=N1 UZBKVHNVGKVIBK-UHFFFAOYSA-N 0.000 claims description 2
- GGFUIBCPKURKMT-UHFFFAOYSA-N ethyl 2-[2-[(4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 GGFUIBCPKURKMT-UHFFFAOYSA-N 0.000 claims description 2
- UWYFMDJTWUHYCH-UHFFFAOYSA-N ethyl 2-[2-[(4-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=N1 UWYFMDJTWUHYCH-UHFFFAOYSA-N 0.000 claims description 2
- JIHXZUUTKHVLNU-UHFFFAOYSA-N ethyl 2-[2-[(4-phenoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 JIHXZUUTKHVLNU-UHFFFAOYSA-N 0.000 claims description 2
- HTGLZCFZWSAEEN-UHFFFAOYSA-N ethyl 2-[2-[(4-propan-2-ylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C(C)C)=N1 HTGLZCFZWSAEEN-UHFFFAOYSA-N 0.000 claims description 2
- VJZNBJUIDMRTPW-UHFFFAOYSA-N ethyl 2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OCC)=CS1 VJZNBJUIDMRTPW-UHFFFAOYSA-N 0.000 claims description 2
- BAWTURGOYHDKPA-UHFFFAOYSA-N ethyl 2-[2-[(5-bromo-2-methoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(Br)C=2)OC)=N1 BAWTURGOYHDKPA-UHFFFAOYSA-N 0.000 claims description 2
- LVTJYYCKVHDIKX-UHFFFAOYSA-N ethyl 2-[2-[(5-chloro-1,3-dimethylpyrazol-4-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C2=C(N(C)N=C2C)Cl)=N1 LVTJYYCKVHDIKX-UHFFFAOYSA-N 0.000 claims description 2
- HKEFYAKHKFYMMG-UHFFFAOYSA-N ethyl 2-[2-[(5-fluoro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(F)C=2)C)=N1 HKEFYAKHKFYMMG-UHFFFAOYSA-N 0.000 claims description 2
- HMGOOODTJVJVDK-CMDGGOBGSA-N ethyl 2-[2-[[(e)-2-phenylethenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)\C=C\C=2C=CC=CC=2)=N1 HMGOOODTJVJVDK-CMDGGOBGSA-N 0.000 claims description 2
- LSUOHCBWXCYLMG-UHFFFAOYSA-N ethyl 2-[2-[[4-(benzenesulfonyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC=C(C=2)S(=O)(=O)C=2C=CC=CC=2)=N1 LSUOHCBWXCYLMG-UHFFFAOYSA-N 0.000 claims description 2
- ZODUISOKTTXHTP-UHFFFAOYSA-N ethyl 2-[2-[[4-(trifluoromethyl)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=N1 ZODUISOKTTXHTP-UHFFFAOYSA-N 0.000 claims description 2
- IGKYRCNENBYGMB-UHFFFAOYSA-N ethyl 2-[2-[[5-(2-methylsulfanylpyrimidin-4-yl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C=2N=C(SC)N=CC=2)=N1 IGKYRCNENBYGMB-UHFFFAOYSA-N 0.000 claims description 2
- MZTOQUINLWUTBG-UHFFFAOYSA-N ethyl 2-[2-[[5-(benzamidomethyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(CNC(=O)C=3C=CC=CC=3)=CC=2)=N1 MZTOQUINLWUTBG-UHFFFAOYSA-N 0.000 claims description 2
- SSTFTUKNWXIXKH-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 SSTFTUKNWXIXKH-UHFFFAOYSA-N 0.000 claims description 2
- PVWVVNUNHXAKGT-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 PVWVVNUNHXAKGT-UHFFFAOYSA-N 0.000 claims description 2
- SRRCAMPLVRPDHC-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C(=O)C(=O)OCC)=CS1 SRRCAMPLVRPDHC-UHFFFAOYSA-N 0.000 claims description 2
- IEGXMLXVLNHQQR-UHFFFAOYSA-N ethyl 3-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]propanoate Chemical compound CCOC(=O)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 IEGXMLXVLNHQQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
- 235000012054 meals Nutrition 0.000 claims description 2
- PDEPXTWYXQSUAK-UHFFFAOYSA-N methyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=C(C)C=C(Cl)C=C1Cl PDEPXTWYXQSUAK-UHFFFAOYSA-N 0.000 claims description 2
- BTWRJCDJRYLOCZ-UHFFFAOYSA-N methyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C BTWRJCDJRYLOCZ-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
본 발명은 상처 치유를 촉진시키는 방법에 관한 것으로, 상기 방법은 상처 치유가 필요한 인간을 포함한 포유류에 11-β-히드록시스테로이드 탈수소효소 타입 1 의 억제제의 유효량을 투여하는 것을 포함하며, 11-β-히드록시스테로이드 탈수소효소 타입 1 의 억제제는 화학식 I 의 화합물 및 그의 약학적으로 허용되는 염, 용매화물, 수화물, 기하이성질체, 호변이성체, 광학이성질체, N-옥시드 및 약물전구체이며, 상기 11-β-히드록시스테로이드 탈수소효소 타입 1 의 억제제는, T, B, X, Y, R1 및 R2 가 본원에 정의된 바와 같은 화학식 I 을 갖는 방법이다. 이러한 화합물은 또한 상처 치유 촉진을 위한 약품의 제조에 사용될 수 있다.
[화학식 I]
Description
관련 출원
본 발명은 2003 년 6 월 25 일에 출원된, 스웨덴 출원 제 0301882-7 호의 우선권을 주장하며, 그 내용은 본원에 참조로서 포함된다.
기술 분야
본 발명은 상처 치유를 위한 화합물의 용도에 관한 것이며, 상기 화합물은 인간 11-β-히드록시스테로이드 탈수소효소 타입 1 효소 (11βHSD1) 에 작용한다.
코티솔은 광범위한 대사 기능 및 다른 기능을 수행한다. 다수의 글루코코티코이드 작용이 혈장 글루코코티코이드의 연장된 증가, 소위 "쿠싱 증후군" 환자에서 예증된다. 쿠싱 증후군을 가진 환자는 혈장 글루코코티코이드의 연장된 증가를 보이며 손상된 글루코스 내성, 제 2 형 당뇨, 중심성 비만 및 골다공증을 나타낸다. 이러한 환자들은 또한 손상된 상처 치유 및 약한 피부를 가진다 (1).
글루코코티코이드는 감염의 위험을 증가하고 노출 상처의 치유를 지연시키는 것으로 나타났다 (2). 글루코코티코이드로 치료된 환자들은 수술을 시행하였을때, 2- 내지 5-배 증가된 합병증 위험율을 가진다 (3).
유럽 특허 출원 제 EP 0902288 은 환자에서의 상처 치유의 상태를 진단하는 방법을 개시하며, 이는 상기 상처 내의 코티솔 수준을 검출하는 방법을 포함한다. 저자들은 건강한 사람의 정상적인 혈장 수준에 비교하여 상처 체액의 상승된 코티솔 수준이 크고, 치료되지 않는 상처에 관련된다는 것을 암시한다 (4).
인간에서는, 11β-HSD 는 코티솔의 코티손으로의, 및 그 반대의 전환을 촉진한다. 설치류에서의 11β-HSD 의 비슷한 작용은 코티코스테론 및 11-디히드로코티코스테론의 상호전환이다 (5). 11β-HSD 의 두개의 동종효소, 11β-HSD1 및 11β-HSD2 를 특성화하였고, 기능 및 조직 분포가 서로 다르다 (6). GR 과 같이, 11β-HSD1 은 간, 지방 조직, 부신 피질, 생식샘, 폐, 뇌하수체, 뇌, 눈 등과 같은 다양한 조직에서 발현된다 (7~9). 11β-HSD1 의 기능은 국부 글루코코티코이드 작용을 미세조정하기 위한 것이다. 11β-HSD 활성은 인간 및 설치류의 피부, 인간 섬유모세포 및 래트 피부 주머니 조직에서 나타났다 (10~13).
상처 치유는 염증, 섬유모세포 증식, 바탕질의 분비, 콜라겐 제조, 혈관형성, 상처 수축 및 상피화를 포함하는 연속적인 작용으로 이루어진다. 이는 3개의 상으로 나뉠수 있다: 염증, 증식 및 재형성 상 ((2) 에 리뷰됨).
수술 환자에서는, 글루코코티코이드로의 치료가 상처 감염의 위험을 증가하고 노출 상처의 치유를 지연시킨다. 동물 모델에서 감금 스트레스가 피하 상처 치료 치유를 늦추고 상처 치유 동안 박테리아성 감염의 감수성을 증가시키는 것이 제시되었다. 이러한 영향은 글루코코티코이드 수용체 길항제 RU486 로의 치료에 의해 역전된다 (14, 15). 글루코코티코이드는 염증을 억제하고, 상처 강도 감소, 상처 구축 억제 및 상피화의 지연에 의해 이러한 영향을 준다 (2). 글루코코티코이드는 사이토카인 및 IGF, TGF-β, EGF, KGF 및 PDGF 와 같은 성장 인자의 작용 또는 생성을 방해하여 상처 치유에 영향을 미친다 (16~19). 또한 글루코코티코이드는 생체내에서 래트 및 마우스 피부 및 래트 및 인간 섬유모세포에서의 콜라겐 합성을 감소시키는 것으로 나타났다 (20).
WO 01/90090 는 이하 정의된 화학식 (I) 의 화합물을 개시하며, 상기 화합물은 인간 11β-HSD1 을 억제하며, 당뇨, 비만, 녹내장, 골다공증, 인지 장애 및 면역 장애와 같은 장애의 치료에 유용할 수 있다. 다른 11β-HSD1 억제제는 예를 들어, WO 01/90091 ; WO 01/90092 ; WO 01/90093 ; WO 01/90094 ; WO 03/044000; WO 03/044009; WO 03/043999; 및 2003년 5월 21일에 출원된 스웨덴 특허 출원 제 SE 0301504-7 호에 개시되어 있다. WO 02/072084 는 상처 치유에 대한 11β-HSD1 억제제로서 글리시리틴산 유도체, 프로게스테론 및 프로게스테론 유도체에 관한 것이다. 그러나, 상처 치유에 대한 본 발명에 따른 11β-HSD1 억제제의 용도는 이전에 개시되지 않았다.
발명의 개시
11β-HSD1 의 억제제가 놀랍게도 상처 치유 촉진에 유용한 것을 발견하였다. 따라서, 본 발명의 첫번째 측면은 상처 치유 촉진 방법을 제공하며, 상기 방법은 상처 치유가 필요한, 인간을 포함한 포유류에 11-β-히드록시스테로이드 탈수소효소 타입 1 의 억제제의 유효량을 투여하는 것을 포함하며, 11-β-히드록시스테로이드 탈수소효소 타입 1 의 억제제는 화학식 I 의 화합물 및 그의 약학적으로 허용되는 염, 용매화물, 수화물, 기하이성질체, 호변이성체, 광학이성질체, N-옥시드 및 약물전구체이다:
[식 중,
T 는 독립적으로 [R]n 으로 임의 치환된 아릴 고리 또는 헤테로아릴 고리 또는 아릴-C2-알케닐 고리이며, 여기서 n 은 0 내지 5 의 정수이며, R 은 수소, 아릴, 헤테로아릴, 헤테로환형 고리, 임의로 할로겐화된 Cl-6-알킬, 임의로 할로겐화된 Cl-6-알콕시, Cl-6-알킬설포닐, 카르복시, 시아노, 니트로, 할로겐, 임의로 1- 또는 2-치환된 아민, 임의로 1- 또는 2-치환된 아미드, 아릴옥시, 아릴설포닐, 아릴아미노이며, 여기서 아릴, 헤테로아릴 및 아릴옥시 잔기 및 헤테로환형 고리는 추가로 하나 이상의 위치에서 서로로부터 독립적으로 C1-6-아실, C1-6-알킬티오, 시아노, 니트로, 수소, 할로겐, 임의로 할로겐화된 Cl-6-알킬, 임의로 할로겐화된 C1-6-알콕시, 임의로 1- 또는 2-치환된 아미드, (벤조일아미노)메틸, 카르복시, 2-티에닐메틸아미 노 또는 ({[4-(2-에톡시-2-옥소에틸)-1,3-티아졸-2-일]아미노}카르보닐) 로 임의 치환될 수 있으며;
Rl 은 수소 또는 Cl-6-알킬이며;
X 는 CH2 또는 CO 이며;
Y 는 CH2, CO 또는 단일 결합이며;
B 는 수소 또는 Cl-6-알킬이며;
R2 는 Cl-6-알킬, 아지도, 아릴티오, 헤테로아릴티오, 할로겐, 히드록시메틸, 2-히드록시에틸아미노메틸, 메틸설포닐옥시메틸, 3-옥소-4-모르폴리놀리닐메틸렌, C1-6-알콕시카르보닐, 및 5-메틸-1,3,4-옥사디아졸-2-일; NR3R4 (여기서, R3 및 R4 는 각각 독립적으로 수소, C1-6-알킬, 임의로 할로겐화된 C1-6알킬설포닐, C1-6-알콕시, 2-메톡시에틸, 2-히드록시에틸, 1-메틸이미다졸릴설포닐, Cl-6-아실, 시클로헥실메틸, 시클로프로판카르보닐, 아릴, 임의로 할로겐화된 아릴설포닐, 푸릴카르보닐, 테트라히드로-2-푸라닐메틸, N-카르브에톡시피페리딜 및 하나 이상의 아릴 또는 헤테로아릴로 치환된 Cl-6-알킬로부터 선택되거나, NR3R4 는 함께 이미다졸, 피페리딘, 피롤리딘, 피페라진, 모르폴린, 옥사제핀, 옥사졸, 티오모르폴린, 1,1-디옥시도티오모르폴린, 2-(3,4-디히드로-2(1H)이소퀴놀리닐), (1S,4S)-2-옥사-5-아자비시클로 [2.2.1]헵트-5-일일 수 있는 헤테로환형계를 나타내며, 헤테로환형계는 Cl-6-알킬, Cl-6-아실, 히드록시, 옥소, t-부톡시카르보닐로 임의 치환될 수 있음); OCONR3R4 (여기서, R3 및 R4 는 각각 독립적으로 수소, Cl-6알킬로부터 선택되거나 함께 모르폴리닐을 형성함); R5O (여기서, R5 는 수소, 임의로 할로겐화된 Cl-6-알킬, 아릴, 헤테로아릴, Cl-6-아실, C1-6-알킬설포닐, 아릴카르보닐, 헤테로아릴카르보닐, 2-카르보메톡시페닐임) 로부터 선택된다].
바람직하게는:
T 가 5-클로로-1,3-디메틸-lH-피라졸-4-일; 4-클로로-2,3,1-벤즈옥사디아졸릴; 5-(디메틸아미노)-1-나프틸; 1-메틸이미다졸-4-일; 1-나프틸 ; 2-나프틸; (E) -2-페닐에테닐; 8-퀴놀리닐; (벤조일아미노) 메틸, 브로모, 클로로, 3-이속사졸릴, 2-(메틸설파닐)-4-피리미디닐, 1-메틸-5-(트리플루오로메틸)피라졸-3-일, 페닐설포닐, 피리딜 중 하나 이상으로 치환된 티에닐; 아세틸아미노, 3-아세틸아미노페닐, 3-아세틸페닐, 벤젠아미노, 1,3-벤조디옥솔-5-일, 2-벤조푸릴, 벤질아미노, 3,5- 비스(트리플루오로메틸)페닐, 브로모, 부톡시, 카르복시, 클로로, 4-카르복시페닐, 3-클로로-2-시아노페녹시, 4-클로로페닐, 5-클로로-2-티에닐, 시아노, 3,4-디클로로페닐, ({[4-(2-에톡시-2-옥소에틸)-1,3-티아졸-2-일]아미노}카르보닐), 플루오로, 5-플루오로-2-메톡시페닐, 2-푸릴, 수소, 요오도, 이소프로필, 메탄설포닐, 메 톡시, 메틸, 4-메틸-1-피페라지닐, 4-메틸-1-피페리디닐, 4-메틸설파닐페닐, 5-메틸-2-티에닐, 4-모르폴리닐, 니트로, 3-니트로페닐, 페녹시, 페닐, n-프로필, 4-피리딜, 3-피리딜메틸아미노, 1-피롤리디닐, 2-티에닐, 3-티에닐, 2-티에닐메틸아미노, 트리플루오로메톡시, 4-트리플루오로메톡시페닐, 및 트리플루오로메틸 중 하나 이상으로 치환된 페닐로부터 선택되며;
Rl 이 수소 또는 메틸이며;
X 가 CH2 또는 CO 이며;
Y 가 CH2, CO 또는 단일 결합이며;
B 가 수소 또는 메틸이며;
R2 가 n-프로필, 아지도, 브로모, 클로로, 2-피리디닐설파닐, 3-옥소-4-모르폴리놀리닐메틸렌, 에톡시카르보닐, 5-메틸-1,3,4-옥사디아졸-2-일; NR3R4 (여기서, R3 및 R4 는 각각 독립적으로 아세틸, 1,3-벤조디옥솔-5-일메틸, 벤질, 3-클로로-2-메틸페닐설포닐, 시클로헥실메틸, 에틸, 2-푸릴카르보닐, 2-푸릴메틸, 수소, 2-히드록시에틸, 2-(lH-인돌-3-일)에틸, 이소프로필, 메톡시, 2-메톡시에틸, 메틸, 4-(1-메틸이미다졸릴)설포닐, 메틸설포닐, 페닐, 프로필, 트리플루오로메틸설포닐로부터 선택되거나; NR3R4 는 함께 4-아세틸피페라지닐, 4-t-부톡시카르보닐피페라지닐, 2-(3,4-디히드로-2(1H)이소퀴놀리닐), (2R,6S)-2,6-디메틸모르폴리닐, (2R)- 2,4-디메틸-1-피페라지닐, 2-히드록시-3-옥소모르폴리닐, 이미다졸릴, 2-메틸-3-옥소모르폴리닐, 4-메틸-2-옥소피페라지닐, 4-메틸피페라지닐, 모르폴리닐, (lS,4S)-2-옥사-5-아자-비시클로[2.2.1]헵트-5-일, 2-옥소이미다졸리닐, 3-옥소모르폴리닐, 3-옥소-1,4-옥사제피닐, 2-옥소옥사졸리닐, 피페라지닐; 피페리디닐; 피롤리디닐; 피롤리도닐, 티오모르폴리닐; 1,1-디옥시도-티오모르폴리닐을 나타냄); OCONR3R4 (여기서, R3 및 R4 는 각각 독립적으로 에틸, 수소로부터 선택되거나 함께 모르폴리닐을 형성함); R5O (여기서, R5 는 아세틸, 벤조일, 벤질, 에틸, 2-플루오로에틸, 2-푸릴카르보닐, 수소, 이소부티릴, 이소프로필, 메틸, 2-카르보메톡시페닐, 메틸설포닐, 페닐, 프로피오닐, 3-피리디닐, 및 2,2,2-트리플루오로에틸임) 로부터 선택된다.
하기 화합물이 특히 바람직하다:
에틸 (2-{[(2,4-디클로로-5-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 2-(2-[[(4-클로로페닐)설포닐]아미노]-1,3-티아졸-4-일)아세테이트,
에틸 2-2(2-{[(4-클로로-2,5-디메틸페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,
에틸 2-(2-{[(2,4-디플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 2-(2-(((4-메틸페닐)설포닐)아미노)-1,3-티아졸-4-일)아세테이트,
에틸 2-(2-{[(2,5-디클로로-3-티에닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}아세테이트,
에틸 2-(2-{[(3-브로모페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-니트로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(3-니트로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(3-메틸페닐)설포닐] 아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(3-클로로페닐)설포닐]아미노}-1, 3-티아졸-4-일) 아세테이트,
에틸 (2-[(4-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(3-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 {2-[(페닐설포닐)아미노]-1,3-티아졸-4-일}아세테이트,
에틸 (2-{[(4-이소프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 [2-({[3-({[4-(2-에톡시-2-옥소에틸)-1,3-티아졸-2-일]아미노}카르보닐)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 [2-([4-({[4-(2-에톡시-2-옥소에틸)-1,3-티아졸-2-일]아미노}카르보닐) 페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 (2-{(2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 [2-{[2-(트리플루오로메틸)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 [2-{[3-(트리플루오로메틸)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 [2-({[4-(트리플루오로메틸)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 2-(2-{[(4-브로모페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-니트로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2,4-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(5-플루오로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-메톡시-4-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(3,5-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸[2-([4-(3-클로로-2-시아노페녹시)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 (2-{[(3,4-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-부톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 [2-({[4-(아세틸아미노)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 {2-[(8-퀴놀리닐설포닐)아미노]-1,3-티아졸-4-일}아세테이트,
에틸 (2-[(3,4-디메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-요오도페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(3-클로로-4-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 [2-([5-(디메틸아미노)-1-나프틸]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 (2-{[(1-메틸-1H-이미다졸-4-일)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(5-브로모-2-메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2,5-디메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 {2-[(2-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세테이트,
에틸 {2-[(메시틸설포닐)아미노]-1,3-티아졸-4-일}아세테이트,
에틸 (2-{[(3-브로모-5-클로로-2-티에닐)설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,
에틸 {2-[({5-[(벤조일아미노)메틸]-2-티에닐}설포닐)아미노]-1,3-티아졸-4- 일}아세테이트,
에틸 {2-[({5-[l-메틸-5-(트리플루오로메틸)-lH-피라졸-3-일]-2-티에닐}설포닐)아미노]-1,3-티아졸-4-일}아세테이트,
에틸 (2-{[(4-시아노페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 {2-[({5-[2-(메틸설파닐)-4-피리미디닐]-2-티에닐}설포닐)아미노]-1, 3-티아졸-4-일}아세테이트,
에틸 (2-{[(3-시아노페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2,4,5-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 [2-({[(E)-2-페닐에테닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 (2-{[(2,3,4-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-[(4-브로모-2,5-디플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일] 아세테이트,
에틸 [2-{[4-(트리플루오로메톡시)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 (2-{[(2,3-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-브로모페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4,5-디클로로-2-티에닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 [2-({[4-(페닐설포닐)-2-티에닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 [2-({[5-(페닐설포닐)-2-티에닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,
에틸 (2-{[(2,6-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-시아노페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-({[4-(아세틸아미노)-3-클로로페닐]설포닐}아미노)-l,3-티아졸-4-일]아세테이트,
에틸 (2-{[(5-클로로-1,3-디메틸-1H-피라졸-4-일)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(3-메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-브로모-5-클로로-2-티에닐)설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,
에틸 2-{2-[(l-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세테이트,
에틸 (2-{[(2,5-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-메탄설포닐페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-메탄설포닐페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-브로모-2-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-메틸-4-트리플루오로메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-[(2,3,4-트리플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-클로로-2,3,1-벤즈옥사디아졸릴)설포닐]아미노}-1,3-티아졸-4- 일)아세테이트,
에틸 (2-{[(2,4,6-트리플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(5-카르복시-4-클로로-2-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-(5-클로로티에닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-(5-(3-이속사졸로)티에닐))설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,
에틸 (2-{[(4-브로모-2-메틸페닐)설포닐]아미노)-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-페녹시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(4-클로로-2,6-디메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(2-메틸-4-트리플루오로메톡시페닐)설포닐]아미노}-1,3-티아졸-4- 일)아세테이트,
에틸 (2-{[(2,4-비스(트리플루오로메틸)페닐)설포닐]아미노}-1,3-티아졸-4- 일)아세테이트,
에틸 2-{2-[[(3-클로로-2-메틸페닐)설포닐](메틸)아미노]-1,3-티아졸-4-일}아세테이트,
에틸 옥소(2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 (2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)(옥소)아세테이트,
에틸 옥소(2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
에틸 {2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}(옥소)아세테이트,
에틸 (2-[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)(옥소)아세테이트,
2-(2-{[(4-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트산,
2-(2-{[(2,5-디클로로-3-티에닐)설포닐]아미노}-1,3-티아졸-4-일)아세트산,
(2-{[(2-클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트산,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트산,
이소프로필 2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,
페닐 2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
메틸 (2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
메틸 {2-[([1,1'-비페닐]-4-일설포닐)아미노]-5-메틸-1,3-티아졸-4-일}아세테이트,
메틸 (2-{[(4-클로로페닐)설포닐]아미노}-5-메틸-1,3-티아졸l-4-일)아세테이트,
메틸 (2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-5-메틸-1,3-티아졸-4-일) 아세테이트,
메틸 [2-({[4-(3-클로로-2-시아노페녹시)페닐]설포닐}아미노)-5-메틸-1,3- 티아졸-4-일]아세테이트,
메틸 (5-메틸-2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
메틸 (5-메틸-2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,
메틸 (2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-5-메틸-1,3-티아졸-4-일)아세테이트,
N-(2-메톡시에틸)-2-(2-{[(4-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,
2-(2-{[(2,5-디클로로-3-티에닐)설포닐]아미노}-1,3-티아졸-4-일)-N-메틸아세트아미드,
N-(1,3-벤조디옥솔-5-일메틸)-2-{2-[(l-나프틸설포닐)아미노]-l,3-티아졸-4-일}아세트아미드,
N-(2-푸릴메틸)-2-{2-[(l-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세트아미드,
2-(2-{[(2,4-디플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-에틸아세트아미드,
N-이소프로필-2-{2-[(1-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세트아미드,
N-[2-(1H-인돌-3-일)에틸]-2-{2-[(1-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세트아미드,
N-(시클로헥실메틸)-2-{2-[(페닐설포닐)아미노]-1,3-티아졸-4-일}아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노-1,3-티아졸-4-일)-N-메틸아세트아미드,
2-(2-{[(3-클로로-3-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-에틸아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-페닐아세트아미드,
2-(2-{[(4-클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-(2-푸릴메틸)아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디에틸아세트아미드,
2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}-N,N-디에틸아세트아미드,
N,N-디에틸-2-(2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,
2-(2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디에틸아세트아미드,
N,N-디에틸-2-(2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세트아미드,
2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}-N,N-디이소프로필아세트아미드,
N,N-디이소프로필-2-(2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세트아미드,
2-(2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디이소프로필아세트아미드,
N,N-디이소프로필-2-(2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디이소프로필아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디프로필아세트아미드,
N-벤질-2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N- 에틸아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디메틸아세트아미드,
3-클로로-N-{4-[2-(3,4-디히드로-2(1H)-이소퀴놀리닐)-2-옥소에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-메틸-N-페닐아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-이소프로필-N-메틸아세트아미드,
2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}-N-이소프로필-N-메틸아세트아미드,
N-에틸-N-메틸-2-(2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4- 일)아세트아미드,
2-(2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-에틸- N-메틸아세트아미드,
N-에틸-N-메틸-2-(2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,
2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}-N-에틸-N-메틸아세트아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-에틸-N- 메틸아세트아미드,
3-클로로-2-메틸-N-{4-[2-옥소-2-(1-피롤리디닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-옥소-2-(l-피페리디닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
N-{4-[2-옥소-2-(1-피페리디닐)에틸]-1,3-티아졸-2-일}[1,1'-비페닐]-4-설폰아미드,
N-4-[2-옥소-2-(l-피페리디닐)에틸]-1,3-티아졸-2-일}-4-프로필벤젠설폰아미드,
2,4-디클로로-6-메틸-N-{4-[2-옥소-2-(1-피페리디닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
2,4,6-트리클로로-N-{4-[2-옥소-2-(1-피페리디닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
2,4,6-트리클로로-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
2,4-디클로로-6-메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,
N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}[1,1'-비페닐]-4-설폰아미드,
N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-l,3-티아졸-2-일}-4-프로필벤젠설폰아미드,
2,4-디클로로-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-클로로-2,6-디메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,
N-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}-4-페녹시벤젠설폰아미드,
2-메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}-4-(트리플루오로메톡시)벤젠설폰아미드,
N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}-2,4-비스(트리플루오로메틸)벤젠설폰아미드,
4-브로모-2-메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(2-푸릴)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(5-플루오로-2-메톡시페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(5-메틸-2-티에닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,
4-(3-아세틸페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(4-트리플루오로메톡시페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(3,4-디클로로페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-l,3-티아졸-2-일}벤젠설폰아미드,
4-(3,4-메틸렌디옥시페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸- 2-일}벤젠설폰아미드,
4-(5-클로로-5-티에닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(4-피리딜)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(3-아세틸아미노페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(3-티에닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(2-티에닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(4-카르복시페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(4-메틸설파닐페닐)-N-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,
4-(3,5-비스(트리플루오로메틸)페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(4-클로로페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(3-니트로페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(2-벤조푸릴)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(1-피롤리디노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(4-메틸-1-피페리디노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(벤젠아미노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(벤질아미노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(2-티에닐메틸아미노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,
4-(4-모르폴리닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(4-메틸-1-피페라지닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
4-(3-피리딜메틸아미노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,
2,4-디클로로-6-메틸-N-{5-메틸-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
N-{5-메틸-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}[1,1'-비페닐]-4-설폰아미드,
2,4,6-트리클로로-N-{5-메틸-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{5-메틸-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,
3-클로로-N-(4-{2-[(2R,6S)-2,6-디메틸모르폴리닐]-2-옥소에틸}-1,3-티아졸-2-일)-2-메틸벤젠설폰아미드,
3-클로로-2-메틸-N-(4-{2-[(1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵트-5-일]-2-옥소에틸}-1,3-티아졸-2-일)벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2-일}[1,1'-비페닐]-4- 설폰아미드,
N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2-일}-4-프로필벤젠설폰아미드,
2,4-디클로로-6-메틸-N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
2,4,6-트리클로로-N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,
N-{4-[2-(1,1-디옥시도-4-티오모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}-4- 프로필벤젠설폰아미드,
tert-부틸 4-[(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세틸]-1-피페라진카르복실레이트,
4-아세틸-(4-[(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세틸])-1-피페라진,
4-[(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세틸]-1- 피페라진 트리플루오로아세테이트,
3-클로로-2-메틸-N-{4-[2-(4-메틸-1-피페라지닐)-2-옥소에틸]-1,3-티아졸-2- 일}벤젠설폰아미드 디히드로클로리드,
2-메틸-N-{4-[2-(4-메틸-1-피페라지닐)-2-옥소에틸]-1,3-티아졸-2-일}-4-(트리플루오로메톡시)벤젠설폰아미드,
2,4-디클로로-6-메틸-N-{4-[2-(4-메틸-1-피페라지닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
2,4-디클로로-N-{4-[2-(4-메틸-1-피페라지닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,
3-클로로-N-(4-{2-[(2R)-2,4-디메틸피페라지닐]-2-옥소에틸}-1,3-티아졸-2-일)-2-메틸벤젠설폰아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-메톡시- N-메틸아세트아미드,
3-클로로-2-메틸-N-[4-(2-옥소펜틸)-1,3-티아졸-2-일]벤젠설폰아미드,
4-클로로-N-[4-(2-히드록시에틸)-l,3-티아졸-2-일]벤젠설폰아미드,
3-클로로-N-[4-(2-히드록시에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,
3-클로로-N-[4-(2-에톡시에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,
3-클로로-N-[4-(2-이소프로폭시에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,
N-{4-[2-(벤질옥시)에틸]-l,3-티아졸-2-일}-3-클로로-2-메틸벤젠설폰아미드,
3-클로로-N-[4-(2-메톡시에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,
3-클로로-N-{4-[2-(2-플루오로에톡시)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(2,2,2-트리플루오로에톡시)에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(2-피리디닐설파닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(3-피리디닐옥시)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-메틸살리실에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 메탄설 포네이트,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노-1,3-티아졸-4-일)에틸 아세테이트,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 프로피오네이트,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 2-메틸프로파노에이트,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 2-푸로에이트,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 벤조에이트,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 4-모르폴린카르복실레이트,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 디에틸카르바메이트,
2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 에틸카르바메이트,
N-[4-(2-아지도에틸)-1,3-티아졸-2-일]-3-클로로-2-메틸벤젠설폰아미드,
N-[4-(2-아미노에틸)-1,3-티아졸-2-일]-3-클로로-2-메틸벤젠설폰아미드 히드로클로리드,
4-클로로-N-{4-[2-(디에틸아미노)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,
3-클로로-N-{4-[2-(디에틸아미노)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드 히드로클로리드,
3-클로로-N-{4-[2-(1-이미다졸릴)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드 히드로클로리드,
3-클로로-2-메틸-N-{4-[2-(4-메틸-1-피페라지닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,
3-클로로-2-메틸-N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 디히드로클로리드,
3-클로로-2-메틸-N-{4-[(4-모르폴리닐)메틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,
2,4,6-트리클로로-N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,
2,4-디클로로-N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,
2,4-디클로로-6-메틸-N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,
N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}-4-프로필벤젠설폰아미드 디히드로클로리드,
3-클로로-N-{4-[2-(에틸아미노)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드,
3-클로로-N-(4-{2-[(2-히드록시에틸)아미노]에틸}-1,3-티아졸-2-일)-2-메틸벤젠설폰아미드,
N-[2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸]-N- 에틸아세트아미드,
3-클로로-2-메틸-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-N-{4-[2-(2-히드록시-3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드,
2,4-디클로로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-l,3-티아졸-2-일}벤젠설폰아미드,
2,4-디클로로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}-6-메틸벤젠설폰아미드,
N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-l,3-티아졸-2-일}-2,4,6-트리클로로벤젠설폰아미드,
4,5-디클로로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}-2-티에닐설폰아미드,
N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}-4-페녹시벤젠설폰아미드,
3-플루오로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-l,3-티아졸-2-일}-5-(2-피리딜)-2-티에닐설폰아미드,
4-아세틸아미노-3-클로로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
N-{4-[(3-옥소-4-모르폴리닐)메틸]-1,3-티아졸-2-일}-3-클로로-2-메틸벤젠설폰아미드,
N-{4-[3-(3-옥소-4-모르폴리닐)프로필]-1,3-티아졸-2-일}-3-클로로-2-메틸벤젠설폰아미드,
N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일},N-메틸-3-클로로-2-메틸벤젠설폰아미드,
3-클로로-2-메틸-N-4-[2-(2-메틸-3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,
N-{4-[2-(아세틸아미노)에틸]-1,3-티아졸-2-일}-3-클로로-2-메틸-벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(4-(3-옥소-1,4-옥사제피닐)에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(1-피롤리도닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(1-(2-옥소이미다졸리닐))에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(1-(2-옥소옥사졸리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-N-{4-[2-(N-(2-푸릴카르보닐),N-2-히드록시에틸아미노)에틸]-1,3- 티아졸-2-일}-2-메틸벤젠설폰아미드,히드로클로리드,
3-클로로-2-메틸-N-{4-[2-(4-메틸-2-옥소피페라지닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(메틸설포닐아미노)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(N-메틸,N-메틸설폰아미노)에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(트리플루오로메틸설포닐아미노)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(N-메틸,N-트리플루오로메틸설폰아미노)에틸]-1, 3-티아졸-2-일}벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[2-(4-(1-메틸이미다졸릴)설포닐아미노)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,
3-클로로-N-{4-[2-(N-(3-클로로-2-메틸페닐설포닐),N-메틸아미노)에틸]-1, 3-티아졸-2-일}-2-메틸벤젠설폰아미드,
N-[4-(2-브로모에틸)-1,3-티아졸-2-일]-3-클로로-2-메틸벤젠설폰아미드,
3-클로로-N-[4-(2-클로로에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,
3-클로로-2-메틸-N-{4-[(5-메틸-1,3,4-옥사디아졸-2-일)메틸]-1,3-티아졸-2- 일}벤젠설폰아미드, 및
3-클로로-N-{4-[2-(에톡시카르보닐)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드.
본 발명의 한 측면에서는, 상기 방법은 지연 또는 감소된 상처 치유를 수반하는 의학적 질환의 치료 또는 예방 방법이다. 이러한 의학적 질환의 예는 당뇨, 및 스테로이트, 특히 글루코코티코이드의 치료에 의해 초래된 질환이다. 본 발명에 따른 방법은 또한 당뇨병성 궤양, 정맥성 궤양 또는 피부 궤양과 같은 만성적 상처에서의 상처 치유의 촉진을 위한 것이다.
상기에 언급된 화합물은 또한 상처 치유 촉진, 예를 들어 지연 또는 손상된 상처 치유를 수반하는 의학적 질환의 치료 또는 예방을 위한 약품의 제조에 사용될 수 있다. 이러한 의학적 질환의 예는 당뇨, 및 스테로이트, 특히 글루코코티코이드의 치료에 의해 초래된 질환이다. 상기에 언급된 화합물은 또한 당뇨병성 궤양, 정맥성 궤양 또는 피부 궤양과 같은 만성적 상처에서의 상처 치유의 촉진을 위해서 사용될 수 있다.
화학식 (I) 을 갖는 화합물의 상기 정의에 독립적 및 조합으로 사용된 여러 용어가 설명될 것이다.
본원의 용어 "아릴"은 6 내지 10 고리 탄소 원자를 갖는 방향족 고리, 예컨 대 C1-6 알킬로 임의 치환될 수 있는 페닐 (Ph) 및 나프틸을 포함하는 것을 의도한다. 치환된 아릴기의 예는 벤질 및 2-메틸페닐이다.
본원에서 용어 "헤테로아릴"은 5 내지 14, 바람직하게는 5 내지 10 고리 원자 예컨대 5, 6, 7, 8, 9 또는 10 고리 원자 (단- 또는 2-환형)를 갖는 단환, 2- 또는 3-환형 방향족 고리계 (오로지 하나의 고리만이 방향족일 필요가있다)를 의미하며, 여기서 하나 이상의 고리 원자는 탄소 이외의 것, 예컨대 질소, 황, 산소 및 셀레늄이다. 이러한 헤테로아릴 고리의 예는 피롤, 이미다졸, 티오펜, 푸란, 티아졸, 이소티아졸, 티아디아졸, 옥사졸, 이속사졸, 옥사디아졸, 피리딘, 피라진, 피리미딘, 피리다진, 피라졸, 트리아졸, 테트라졸, 크로만, 이소크로만, 퀴놀린, 퀴녹살린, 이소퀴놀린, 프탈라진, 시놀린, 퀴나졸린, 인돌, 이소인돌, 인돌린, 이소인돌린, 벤조티오펜, 벤조푸란, 이소벤조푸란, 벤즈옥사졸, 2,1,3-벤즈옥사디아졸, 벤조티아졸, 2,1,3-벤조티아졸, 2,1,3-벤조셀레나디아졸, 벤즈이미다졸, 인다졸, 벤조디옥산, 인단, 1,2,3,4-테트라히드로퀴놀린, 3,4-디히드로-2H-1,4-벤족사진, 1,5-나프티리딘, 1,8-나프티리딘, 아크리딘, 페나진 및 잔텐이다. 단환형 헤테로아릴 고리의 예는 피롤, 이미다졸, 티오펜, 푸란, 티아졸, 이소티아졸, 티아디아졸, 옥사졸, 이속사졸, 옥사디아졸, 피리딘, 피라진, 피리미딘, 피리다진, 피라졸, 트리아졸 및 테트라졸이다.
본원의 용어 "헤테로환형"은 4 내지 14, 바람직하게는 4 내지 10 고리 원자를 갖는 불포화, 또한 부분적 및 완전히 포화된 단-, 2- 및 3-환형 고리, 예컨대, 예를 들어, 상기 언급된 헤테로아릴기 및 상응하는 부분적 포화 또는 완전히 포화된 헤테로환식 고리를 포함하는 것을 의도한다. 대표적인 포화 헤테로환형 고리는 아제티딘, 피롤리딘, 피페리딘, 피페라진, 모르폴린, 티오모르폴린 및 1,4-옥사제판이다.
본원에 따른 화학식 I 의 화합물의 C1-6-알킬은 선형 또는 분지형일 수 있으며, 바람직하게는 C1-4-알킬이다. 대표적인 알킬기는 메틸, 에틸, 프로필, 이소프로필, 부틸, sec-부틸, tert-부틸, 펜틸, 이소펜틸, 헥실 및 이소헥실이다. "Cl-6-알킬" 범위의 부분에 대해서는 그의 모든 하위기 예컨대 C1-5-알킬, C1-4-알킬, C2-6-알킬, C2-5-알킬, C2-4-알킬, C2-3-알킬, C3-6-알킬, C4-5-알킬 등이 고려된다.
본원에 따른 화학식 (I) 의 화합물의 Cl-6-알콕시는 선형 또는 분지형일 수 있으며, 바람직하게는 Cl-4-알콕시이다. 대표적인 알콕시기는 메톡시, 에톡시, 프로폭시, 이소프로폭시, 부톡시, sec-부톡시, tert-부톡시, 펜틸옥시, 이소펜틸옥시, 헥실옥시 및 이소헥실옥시이다. "Cl-6-알콕시" 범위의 부분에 대해서는 그의 모든 하위기 예컨대 C1-5-알콕시, C1-4-알콕시, C2-6-알콕시, C2-5-알콕시, C2-4-알콕시, C2-3-알콕시, C3-6-알콕시, C4-5-알콕시 등이 고려된다.
본원에 따른 화학식 I 의 화합물의 Cl-6-아실은 포화 또는 불포화일 수 있으며, 바람직하게는 Cl-4-아실이다. 대표적인 아실기는 포르밀, 아세틸, 프로피오 닐, 부티릴, 이소부티릴, 발레릴, 이소발레릴, 부테노일 (예를 들어, 3-부테노일), 헥세노일 (예를 들어 5-헥세노일)을 포함한다. "Cl-6-아실" 범위의 부분에 대해서는 그의 모든 하위기 예컨대 C1-5-아실, C1-4-아실, C2-6-아실, C2-5-알콕시, C2-4-아실, C2-3-아실, C3-6-아실, C4-5-아실 등이 고려된다.
본원에 따른 화학식 I 의 화합물의 C2-6-알케닐은 선형, 분지형 또는 환형일 수 있으며, 바람직하게는 C2-4-알케닐이다. 대표적인 알케닐기는 비닐, 1-프로페닐, 2-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 1-펜테닐, 2-펜테닐, 1-헥세닐, 및 2-헥세닐을 포함한다. "C2-6-알케닐" 범위의 부분에 대해서는 그의 모든 하위기 예컨대 C2-5-알케닐, C2-4-알케닐, C2-3-알케닐, C3-6-알케닐, C4-5-알케닐 등이 고려된다.
본원의 용어 "할로겐"은 플루오린, 클로린, 브로민 및 요오드를 포함하는 것으로 의도된다.
본원의 용어 "설파닐"은 티오기를 의미한다.
본원의 표현 1- 또는 2-치환은 문제가 되는 작용기가 독립적으로 H, C1-6-아실, C1-6- 알케닐, C1-6-(시클로)알킬, 아릴, 피리딜메틸, 또는 헤테로환형 고리, 예를 들어, 아제티딘, 피롤리딘, 피페리딘, 피페라진, 모르폴린 및 티오모르폴린로 치환될 수 있음을 의미하며, 헤테로환형 고리는 Cl-6-알킬로 임의 치환될 수 있다. 표현 "임의로 1- 또는 2-치환된"은 문제가되는 작용기가 또한 독립적으로 수소로 치환될 수 있음을 의미한다.
본 발명에서 계획한 치환체 및 변수는 오로지 안정적 화합물의 형성을 도모하는 것만이다. 본원에 사용된 이러한 용어 "안정적"은 제조되기에 충분한 안정성을 가지며 본원에 열거된 목적 (예를 들어, 11-β-HSD1-매개 질병, 11-β-HSD1 억제, 질병의 치료를 위한 대상으로의 치료적 투여)에 유용하기에 충분한 시간 동안 화합물의 보전 (integrity)을 유지시키는 화합물을 가리킨다.
본원의 용어 "약물전구체 형태"는 약리학적으로 허용되는 유도체, 예컨대 에스테르 또는 아미드를 의미하며, 유도체는 체내에서 생체전환되어 활성 약물을 형성한다 (Goodman and Gilman's, The Pharmacological basis of Therapeutics, 8th ed., McGraw-Hill, Int. Ed. 1992,"Biotransformation of Drugs, p. 13-15 참조).
본원의 "약학적으로 허용되는"은 일반적으로 안전하며, 무독성이고 생물학적으로나 달리 바람직스럽지 못한 것이 아닌, 약학적 조성물을 제조하기에 유용한 것을 의미하며, 수의학적 용도 및 인간 약학적 용도에 유용한 것을 포함한다.
본원의 "약학적으로 허용되는 염"은 상기에 정의된 바와 같고, 목적되는 약학적 활성을 지니는 약학적으로 허용되는 염을 의미한다. 이러한 염은 유기산 및 무기산, 예컨대 염화 수소, 브롬화 수소, 요오드화 수소, 황산, 인산, 아세트산, 글리콜산, 말레산, 말론산, 옥살산, 메탄설폰산, 트리플로오로아세트산, 푸마르산, 석신산, 타르타르산, 시트르산, 벤조산, 아스코르브산 등으로 형성된 산 부 가염을 포함한다. 염기 부가염은 유기염기 및 무기염기, 예컨대 소듐, 암모니아, 포타슘, 칼슘, 에탄올아민, 디에탄올아민, N-메틸글루카민, 콜린 등으로 형성될 수 있다.
화학식 (I) 의 화합물은 WO 01/90090 에 기술된 방법에 따라 제조될 수 있다.
본 발명에 따른 용도를 위해, 화학식 (I) 의 화합물은 바람직하게 국소적으로 투여될 수 있다. 그러나, 화합물은 또한 다른 경로, 예를 들어 경구, 복막내, 관절내, 두개내, 진피내, 근육내, 안내, 경막내, 정맥내, 피하를 통해 투여될 수 있다.
실시예 1
당뇨병성 KKAy 마우스를 마취하에 수술하였으며, 카테터를 목정맥에 삽입하였다. 11-β-HSD1 억제제 BVT.2733 (3-클로로-2-메틸-N-{4-[2-옥소-2-(1-피페라지닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드; 이러한 화합물의 트리플루오로아세테이트는 WO 01/90090 에 실시예 172A 에 개시된다) 또는 4 내지 6 일 후 시작되고 3.5 일 동안 지속된 비히클 (vehicle) 로의 일일 2회 경구 치료 (200 mg/kg/day).
수술 상처의 상처 치유에 대한 유리한 효과를 치료 동안 관찰하였다. BVT.2733 치료된 마우스에서는, 대조 마우스와 비교하여 상처 부위 및 주위에서 합병증이 덜 관찰되었다. 유리한 효과의 예는 상처 내의 보다 적은 고름, 및 보다 우수한 상처 강도이다. 58% 의 비히클 치료된 동물은 치료 기간 동안 합병 증을 나타낸 반면 BVT.2733 치료된 동물의 오로지 24% 에서만 합병증이 존재했다.
실시예 2
(a) 11-β-HSD1 억제제 (예를 들어 BVT.2733) 의 상처 치유에 대한 유리한 효과를 당뇨병성 KKAy 마우스에서 절제성 상치-치유 모델을 사용하여 확인하였다. 피부밑 근육층을 포함한 1 cm 의 전체층 상처를 외과용 칼로 마우스의 등에 내었다. 마우스를 BVT.2733 로 5 일 동안 치료하였다. 치료 제 2 일 및 9 일에 상처를 수확하고, 엠베딩 (embedding) 하고, 박편화 (section) 하였다. 헤마톡실린/에오신으로의 절편의 조직학적 염색을, 재상피화 (re-epithelialization) 및본빌레브란트 인자 (von Willebrand factor) 에 대한 면역염색법의 정도를 측정하기위해 만들어, 혈관재형성을 측정하였다.
(b) 11-β-HSD1 억제제의 유리한 효과를 시험관내 (in vitro) 실험에서 확인하였다. 상처 치유 과정에서 중요한 세표 유형인 인간 각질세포 및 섬유모세포의 증식을 11-β-HSD1 억제제와의 배양 후 연구하였다.
(c) 11-β-HSD1 억제제로의 치료 후, 상처 치유에 대한 효과를 인간 유방 피부로부터의 체외이식편 (explant) 상의 상처에서도 연구하였다. 상기 물질의 증식적 효과 및 재상피화에 대한 효과를 측정하였다.
[참조]
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Claims (12)
- 상처 치유를 촉진시키는 방법으로서, 상기 방법은 상처 치유가 필요한, 인간을 포함한 포유류에 11-β-히드록시스테로이드 탈수소효소 타입 1 의 억제제의 유효량을 투여하는 것을 포함하며, 11-β-히드록시스테로이드 탈수소효소 타입 1 의 억제제는 화학식 I 의 화합물 및 그의 약학적으로 허용되는 염, 용매화물, 수화물, 기하이성질체, 호변이성체, 광학이성질체, N-옥시드 및 약물전구체인 방법:[화학식 I]
[식 중,T 는 독립적으로 [R]n 으로 임의 치환된 아릴 고리 또는 헤테로아릴 고리 또는 아릴-C2-알케닐 고리이며, 여기서 n 은 0 내지 5 의 정수이며, R 은 수소, 아릴, 헤테로아릴, 헤테로환형 고리, 임의로 할로겐화된 Cl-6-알킬, 임의로 할로겐화된 Cl-6-알콕시, Cl-6-알킬설포닐, 카르복시, 시아노, 니트로, 할로겐, 임의로 1- 또는 2-치환된 아민, 임의로 1- 또는 2-치환된 아미드, 아릴옥시, 아릴설포닐, 아릴아미노이며, 여기서 아릴, 헤테로아릴 및 아릴옥시 잔기 및 헤테로환형 고리는 추가로 하 나 이상의 위치에서 서로로부터 독립적으로 C1-6-아실, C1-6-알킬티오, 시아노, 니트로, 수소, 할로겐, 임의로 할로겐화된 Cl-6-알킬, 임의로 할로겐화된 C1-6-알콕시, 임의로 1- 또는 2-치환된 아미드, (벤조일아미노)메틸, 카르복시, 2-티에닐메틸아미노 또는 ({[4-(2-에톡시-2-옥소에틸)-1,3-티아졸-2-일]아미노}카르보닐)로 임의 치환될 수 있으며;Rl 은 수소 또는 Cl-6-알킬이며;X 는 CH2 또는 CO 이며;Y 는 CH2, CO 또는 단일 결합이며;B 는 수소 또는 Cl-6-알킬이며;R2 는 Cl-6-알킬, 아지도, 아릴티오, 헤테로아릴티오, 할로겐, 히드록시메틸, 2-히드록시에틸아미노메틸, 메틸설포닐옥시메틸, 3-옥소-4-모르폴리놀리닐메틸렌, C1-6-알콕시카르보닐, 및 5-메틸-1,3,4-옥사디아졸-2-일; NR3R4 (여기서, R3 및 R4 는 각각 독립적으로 수소, C1-6-알킬, 임의로 할로겐화된 C1-6알킬설포닐, C1-6-알콕시, 2-메톡시에틸, 2-히드록시에틸, 1-메틸이미다졸릴설포닐, Cl-6-아실, 시클로헥실메틸, 시클로프로판카르보닐, 아릴, 임의로 할로겐화된 아릴설포닐, 푸릴카르보닐, 테트라히드로-2-푸라닐메틸, N-카르브에톡시피페리딜 및 하나 이상의 아릴 또는 헤 테로아릴로 치환된 Cl-6-알킬로부터 선택되거나, NR3R4 는 함께 이미다졸, 피페리딘, 피롤리딘, 피페라진, 모르폴린, 옥사제핀, 옥사졸, 티오모르폴린, 1,1- 디옥시도티오모르폴린, 2-(3,4-디히드로-2(1H)이소퀴놀리닐), (1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵트-5-일일 수 있는 헤테로환형계를 나타내며, 헤테로환형계는 Cl-6-알킬, Cl-6-아실, 히드록시, 옥소, t-부톡시카르보닐로 임의 치환될 수 있음); OCONR3R4 (여기서, R3 및 R4 는 각각 독립적으로 수소, Cl-6알킬로부터 선택되거나 함께 모르폴리닐을 형성함); R5O (여기서, R5 는 수소, 임의로 할로겐화된 Cl-6-알킬, 아릴, 헤테로아릴, Cl-6-아실, C1-6-알킬설포닐, 아릴카르보닐, 헤테로아릴카르보닐, 2-카르보메톡시페닐임) 로부터 선택된다]. - 제 1 항에 있어서,T 가 5-클로로-1,3-디메틸-lH-피라졸-4-일; 4-클로로-2,3,1-벤즈옥사디아졸릴; 5-(디메틸아미노)-1-나프틸; 1-메틸이미다졸-4-일; 1-나프틸 ; 2-나프틸; (E) -2-페닐에테닐; 8-퀴놀리닐; (벤조일아미노) 메틸, 브로모, 클로로, 3-이속사졸릴, 2-(메틸설파닐)-4-피리미디닐, 1-메틸-5-(트리플루오로메틸)피라졸-3-일, 페닐설포닐, 피리딜 중 하나 이상으로 치환된 티에닐; 아세틸아미노, 3-아세틸아미노페닐, 3-아세틸페닐, 벤젠아미노, 1,3-벤조디옥솔-5-일, 2-벤조푸릴, 벤질아미노, 3,5- 비스(트리플루오로메틸)페닐, 브로모, 부톡시, 카르복시, 클로로, 4-카르복시페닐, 3-클로로-2-시아노페녹시, 4-클로로페닐, 5-클로로-2-티에닐, 시아노, 3,4-디클로로페닐, ({[4-(2-에톡시-2-옥소에틸)-1,3-티아졸-2-일]아미노}카르보닐), 플루오로, 5-플루오로-2-메톡시페닐, 2-푸릴, 수소, 요오도, 이소프로필, 메탄설포닐, 메톡시, 메틸, 4-메틸-1-피페라지닐, 4-메틸-1-피페리디닐, 4-메틸설파닐페닐, 5-메틸-2-티에닐, 4-모르폴리닐, 니트로, 3-니트로페닐, 페녹시, 페닐, n-프로필, 4-피리딜, 3-피리딜메틸아미노, 1-피롤리디닐, 2-티에닐, 3-티에닐, 2-티에닐메틸아미노, 트리플루오로메톡시, 4-트리플루오로메톡시페닐, 및 트리플루오로메틸 중 하나 이상으로 치환된 페닐로부터 선택되며;Rl 이 수소 또는 메틸이며;X 가 CH2 또는 CO 이며;Y 가 CH2, CO 또는 단일 결합이며;B 가 수소 또는 메틸이며;R2 가 n-프로필, 아지도, 브로모, 클로로, 2-피리디닐설파닐, 3-옥소-4-모르폴리놀리닐메틸렌, 에톡시카르보닐, 5-메틸-1,3,4-옥사디아졸-2-일; NR3R4 (여기서, R3 및 R4 는 각각 독립적으로 아세틸, 1,3-벤조디옥솔-5-일메틸, 벤질, 3-클로로-2-메틸페닐설포닐, 시클로헥실메틸, 에틸, 2-푸릴카르보닐, 2-푸릴메틸, 수소, 2-히드록시에틸, 2-(lH-인돌-3-일)에틸, 이소프로필, 메톡시, 2-메톡시에틸, 메틸, 4- (1-메틸이미다졸릴)설포닐, 메틸설포닐, 페닐, 프로필, 트리플루오로메틸설포닐로부터 선택되거나; NR3R4 는 함께 4-아세틸피페라지닐, 4-t-부톡시카르보닐피페라지닐, 2-(3,4-디히드로-2(1H)이소퀴놀리닐), (2R,6S)-2,6-디메틸모르폴리닐, (2R)-2,4-디메틸-1-피페라지닐, 2-히드록시-3-옥소모르폴리닐, 이미다졸릴, 2-메틸-3-옥소모르폴리닐, 4-메틸-2-옥소피페라지닐, 4-메틸피페라지닐, 모르폴리닐, (lS,4S)-2-옥사-5-아자-비시클로[2.2.1]헵트-5-일, 2-옥소이미다졸리닐, 3-옥소모르폴리닐, 3-옥소-1,4-옥사제피닐, 2-옥소옥사졸리닐, 피페라지닐; 피페리디닐; 피롤리디닐; 피롤리도닐, 티오모르폴리닐; 1,1-디옥시도-티오모르폴리닐을 나타냄); OCONR3R4 (여기서, R3 및 R4 는 각각 독립적으로 에틸, 수소로부터 선택되거나 함께 모르폴리닐을 형성함); R5O (여기서, R5 는 아세틸, 벤조일, 벤질, 에틸, 2-플루오로에틸, 2-푸릴카르보닐, 수소, 이소부티릴, 이소프로필, 메틸, 2-카르보메톡시페닐, 메틸설포닐, 페닐, 프로피오닐, 3-피리디닐, 및 2,2,2-트리플루오로에틸임) 로부터 선택되는 방법.
- 제 1 항 내지 제 2 항에 있어서, 화합물이 하기로부터 선택되는 방법:에틸 (2-{[(2,4-디클로로-5-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 2-(2-[[(4-클로로페닐)설포닐]아미노]-1,3-티아졸-4-일)아세테이트,에틸 2-2(2-{[(4-클로로-2,5-디메틸페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,에틸 2-(2-{[(2,4-디플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 2-(2-(((4-메틸페닐)설포닐)아미노)-1,3-티아졸-4-일)아세테이트,에틸 2-(2-{[(2,5-디클로로-3-티에닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}아세테이트,에틸 2-(2-{[(3-브로모페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-니트로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(3-니트로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(3-메틸페닐)설포닐] 아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(3-클로로페닐)설포닐]아미노}-1, 3-티아졸-4-일) 아세테이트,에틸 (2-[(4-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(3-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 {2-[(페닐설포닐)아미노]-1,3-티아졸-4-일}아세테이트,에틸 (2-{[(4-이소프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 [2-({[3-({[4-(2-에톡시-2-옥소에틸)-1,3-티아졸-2-일]아미노}카르보닐)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 [2-([4-({[4-(2-에톡시-2-옥소에틸)-1,3-티아졸-2-일]아미노}카르보닐) 페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 (2-{(2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 [2-{[2-(트리플루오로메틸)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 [2-{[3-(트리플루오로메틸)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 [2-({[4-(트리플루오로메틸)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 2-(2-{[(4-브로모페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-니트로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2,4-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(5-플루오로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-메톡시-4-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(3,5-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸[2-([4-(3-클로로-2-시아노페녹시)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 (2-{[(3,4-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-부톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 [2-({[4-(아세틸아미노)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 {2-[(8-퀴놀리닐설포닐)아미노]-1,3-티아졸-4-일}아세테이트,에틸 (2-[(3,4-디메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-요오도페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(3-클로로-4-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 [2-([5-(디메틸아미노)-1-나프틸]설포닐}아미노)-1,3-티아졸-4-일]아세 테이트,에틸 (2-{[(1-메틸-1H-이미다졸-4-일)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(5-브로모-2-메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2,5-디메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 {2-[(2-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세테이트,에틸 {2-[(메시틸설포닐)아미노]-1,3-티아졸-4-일}아세테이트,에틸 (2-{[(3-브로모-5-클로로-2-티에닐)설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,에틸 {2-[({5-[(벤조일아미노)메틸]-2-티에닐}설포닐)아미노]-1,3-티아졸-4- 일}아세테이트,에틸 {2-[({5-[l-메틸-5-(트리플루오로메틸)-lH-피라졸-3-일]-2-티에닐}설포닐)아미노]-1,3-티아졸-4-일}아세테이트,에틸 (2-{[(4-시아노페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 {2-[({5-[2-(메틸설파닐)-4-피리미디닐]-2-티에닐}설포닐)아미노]-1, 3-티아졸-4-일}아세테이트,에틸 (2-{[(3-시아노페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2,4,5-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 [2-({[(E)-2-페닐에테닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 (2-{[(2,3,4-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-[(4-브로모-2,5-디플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일] 아세테이트,에틸 [2-{[4-(트리플루오로메톡시)페닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 (2-{[(2,3-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-브로모페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4,5-디클로로-2-티에닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 [2-({[4-(페닐설포닐)-2-티에닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 [2-({[5-(페닐설포닐)-2-티에닐]설포닐}아미노)-1,3-티아졸-4-일]아세테이트,에틸 (2-{[(2,6-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-시아노페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-({[4-(아세틸아미노)-3-클로로페닐]설포닐}아미노)-l,3-티아졸-4-일]아세테이트,에틸 (2-{[(5-클로로-1,3-디메틸-1H-피라졸-4-일)설포닐]아미노}-1,3-티아졸 -4-일)아세테이트,에틸 (2-{[(3-메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-브로모-5-클로로-2-티에닐)설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,에틸 2-{2-[(l-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세테이트,에틸 (2-{[(2,5-디클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-메탄설포닐페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-메탄설포닐페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-브로모-2-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-메틸-4-트리플루오로메톡시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-[(2,3,4-트리플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-클로로-2,3,1-벤즈옥사디아졸릴)설포닐]아미노}-1,3-티아졸-4- 일)아세테이트,에틸 (2-{[(2,4,6-트리플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(5-카르복시-4-클로로-2-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-(5-클로로티에닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-(5-(3-이속사졸로)티에닐))설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,에틸 (2-{[(4-브로모-2-메틸페닐)설포닐]아미노)-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-페녹시페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(4-클로로-2,6-디메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(2-메틸-4-트리플루오로메톡시페닐)설포닐]아미노}-1,3-티아졸-4- 일)아세테이트,에틸 (2-{[(2,4-비스(트리플루오로메틸)페닐)설포닐]아미노}-1,3-티아졸-4- 일)아세테이트,에틸 2-{2-[[(3-클로로-2-메틸페닐)설포닐](메틸)아미노]-1,3-티아졸-4-일}아세테이트,에틸 옥소(2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,에틸 (2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)(옥소)아세테이트,에틸 옥소(2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세 테이트,에틸 {2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}(옥소)아세테이트,에틸 (2-[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)(옥소)아세테이트,2-(2-{[(4-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트산,2-(2-{[(2,5-디클로로-3-티에닐)설포닐]아미노}-1,3-티아졸-4-일)아세트산,(2-{[(2-클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트산,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트산,이소프로필 2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세테이트,페닐 2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,메틸 (2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,메틸 {2-[([1,1'-비페닐]-4-일설포닐)아미노]-5-메틸-1,3-티아졸-4-일}아세테이트,메틸 (2-{[(4-클로로페닐)설포닐]아미노}-5-메틸-1,3-티아졸l-4-일)아세테이트,메틸 (2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-5-메틸-1,3-티아졸-4-일) 아세테이트,메틸 [2-({[4-(3-클로로-2-시아노페녹시)페닐]설포닐}아미노)-5-메틸-1,3- 티아졸-4-일]아세테이트,메틸 (5-메틸-2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,메틸 (5-메틸-2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세테이트,메틸 (2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-5-메틸-1,3-티아졸-4-일)아세테이트,N-(2-메톡시에틸)-2-(2-{[(4-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,2-(2-{[(2,5-디클로로-3-티에닐)설포닐]아미노}-1,3-티아졸-4-일)-N-메틸아세트아미드,N-(1,3-벤조디옥솔-5-일메틸)-2-{2-[(l-나프틸설포닐)아미노]-l,3-티아졸-4-일}아세트아미드,N-(2-푸릴메틸)-2-{2-[(l-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세트아미드,2-(2-{[(2,4-디플루오로페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-에틸아세트아미드,N-이소프로필-2-{2-[(1-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세트아미 드,N-[2-(1H-인돌-3-일)에틸]-2-{2-[(1-나프틸설포닐)아미노]-1,3-티아졸-4-일}아세트아미드,N-(시클로헥실메틸)-2-{2-[(페닐설포닐)아미노]-1,3-티아졸-4-일}아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노-1,3-티아졸-4-일)-N-메틸아세트아미드,2-(2-{[(3-클로로-3-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-에틸아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-페닐아세트아미드,2-(2-{[(4-클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-(2-푸릴메틸)아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디에틸아세트아미드,2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}-N,N-디에틸아세트아미드,N,N-디에틸-2-(2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아 미드,2-(2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디에틸아세트아미드,N,N-디에틸-2-(2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세트아미드,2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}-N,N-디이소프로필아세트아미드,N,N-디이소프로필-2-(2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세트아미드,2-(2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디이소프로필아세트아미드,N,N-디이소프로필-2-(2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디이소프로필아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디프로필아세트아미드,N-벤질-2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N- 에틸아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N,N-디메틸 아세트아미드,3-클로로-N-{4-[2-(3,4-디히드로-2(1H)-이소퀴놀리닐)-2-옥소에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-메틸-N-페닐아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-이소프로필-N-메틸아세트아미드,2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}-N-이소프로필-N-메틸아세트아미드,N-에틸-N-메틸-2-(2-{[(2,4,6-트리클로로페닐)설포닐]아미노}-1,3-티아졸-4- 일)아세트아미드,2-(2-{[(2,4-디클로로-6-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-에틸- N-메틸아세트아미드,N-에틸-N-메틸-2-(2-{[(4-프로필페닐)설포닐]아미노}-1,3-티아졸-4-일)아세트아미드,2-{2-[([1,1'-비페닐]-4-일설포닐)아미노]-1,3-티아졸-4-일}-N-에틸-N-메틸아세트아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-에틸-N- 메틸아세트아미드,3-클로로-2-메틸-N-{4-[2-옥소-2-(1-피롤리디닐)에틸]-1,3-티아졸-2-일}벤젠 설폰아미드,3-클로로-2-메틸-N-{4-[2-옥소-2-(l-피페리디닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,N-{4-[2-옥소-2-(1-피페리디닐)에틸]-1,3-티아졸-2-일}[1,1'-비페닐]-4-설폰아미드,N-4-[2-옥소-2-(l-피페리디닐)에틸]-1,3-티아졸-2-일}-4-프로필벤젠설폰아미드,2,4-디클로로-6-메틸-N-{4-[2-옥소-2-(1-피페리디닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,2,4,6-트리클로로-N-{4-[2-옥소-2-(1-피페리디닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,2,4,6-트리클로로-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,2,4-디클로로-6-메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}[1,1'-비페닐]-4-설폰아미드,N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-l,3-티아졸-2-일}-4-프로필벤젠설폰아 미드,2,4-디클로로-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-클로로-2,6-디메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,N-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}-4-페녹시벤젠설폰아미드,2-메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}-4-(트리플루오로메톡시)벤젠설폰아미드,N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}-2,4-비스(트리플루오로메틸)벤젠설폰아미드,4-브로모-2-메틸-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(2-푸릴)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(5-플루오로-2-메톡시페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(5-메틸-2-티에닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,4-(3-아세틸페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤 젠설폰아미드,4-(4-트리플루오로메톡시페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(3,4-디클로로페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-l,3-티아졸-2-일}벤젠설폰아미드,4-(3,4-메틸렌디옥시페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸- 2-일}벤젠설폰아미드,4-(5-클로로-5-티에닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(4-피리딜)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(3-아세틸아미노페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(3-티에닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(2-티에닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(4-카르복시페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(4-메틸설파닐페닐)-N-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,4-(3,5-비스(트리플루오로메틸)페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(4-클로로페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(3-니트로페닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(2-벤조푸릴)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(1-피롤리디노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(4-메틸-1-피페리디노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(벤젠아미노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(벤질아미노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(2-티에닐메틸아미노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,4-(4-모르폴리닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤 젠설폰아미드,4-(4-메틸-1-피페라지닐)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,4-(3-피리딜메틸아미노)-N-{4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,2,4-디클로로-6-메틸-N-{5-메틸-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,N-{5-메틸-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}[1,1'-비페닐]-4-설폰아미드,2,4,6-트리클로로-N-{5-메틸-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{5-메틸-4-[2-(4-모르폴리닐)-2-옥소에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,3-클로로-N-(4-{2-[(2R,6S)-2,6-디메틸모르폴리닐]-2-옥소에틸}-1,3-티아졸-2-일)-2-메틸벤젠설폰아미드,3-클로로-2-메틸-N-(4-{2-[(1S,4S)-2-옥사-5-아자비시클로[2.2.1]헵트-5-일]-2-옥소에틸}-1,3-티아졸-2-일)벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2-일}[1,1'-비페닐]-4- 설폰아미드,N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2-일}-4-프로필벤젠설폰아미드,2,4-디클로로-6-메틸-N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,2,4,6-트리클로로-N-{4-[2-옥소-2-(4-티오모르폴리닐)에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,N-{4-[2-(1,1-디옥시도-4-티오모르폴리닐)-2-옥소에틸]-1,3-티아졸-2-일}-4- 프로필벤젠설폰아미드,tert-부틸 4-[(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세틸]-1-피페라진카르복실레이트,4-아세틸-(4-[(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일) 아세틸])-1-피페라진,4-[(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)아세틸]-1- 피페라진 트리플루오로아세테이트,3-클로로-2-메틸-N-{4-[2-(4-메틸-1-피페라지닐)-2-옥소에틸]-1,3-티아졸-2- 일}벤젠설폰아미드 디히드로클로리드,2-메틸-N-{4-[2-(4-메틸-1-피페라지닐)-2-옥소에틸]-1,3-티아졸-2-일}-4-(트리플루오로메톡시)벤젠설폰아미드,2,4-디클로로-6-메틸-N-{4-[2-(4-메틸-1-피페라지닐)-2-옥소에틸]-1,3-티아 졸-2-일}벤젠설폰아미드,2,4-디클로로-N-{4-[2-(4-메틸-1-피페라지닐)-2-옥소에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,3-클로로-N-(4-{2-[(2R)-2,4-디메틸피페라지닐]-2-옥소에틸}-1,3-티아졸-2-일)-2-메틸벤젠설폰아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)-N-메톡시- N-메틸아세트아미드,3-클로로-2-메틸-N-[4-(2-옥소펜틸)-1,3-티아졸-2-일]벤젠설폰아미드,4-클로로-N-[4-(2-히드록시에틸)-l,3-티아졸-2-일]벤젠설폰아미드,3-클로로-N-[4-(2-히드록시에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,3-클로로-N-[4-(2-에톡시에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,3-클로로-N-[4-(2-이소프로폭시에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,N-{4-[2-(벤질옥시)에틸]-l,3-티아졸-2-일}-3-클로로-2-메틸벤젠설폰아미드,3-클로로-N-[4-(2-메톡시에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,3-클로로-N-{4-[2-(2-플루오로에톡시)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(2,2,2-트리플루오로에톡시)에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(2-피리디닐설파닐)에틸]-1,3-티아졸-2-일}벤젠설 폰아미드,3-클로로-2-메틸-N-{4-[2-(3-피리디닐옥시)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-메틸살리실에틸]-1,3-티아졸-2-일}벤젠설폰아미드,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 메탄설포네이트,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노-1,3-티아졸-4-일)에틸 아세테이트,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 프로피오네이트,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 2-메틸프로파노에이트,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 2-푸로에이트,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 벤조에이트,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 4-모르폴린카르복실레이트,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 디에틸카르바메이트,2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸 에틸카르바메이트,N-[4-(2-아지도에틸)-1,3-티아졸-2-일]-3-클로로-2-메틸벤젠설폰아미드,N-[4-(2-아미노에틸)-1,3-티아졸-2-일]-3-클로로-2-메틸벤젠설폰아미드 히드로클로리드,4-클로로-N-{4-[2-(디에틸아미노)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,3-클로로-N-{4-[2-(디에틸아미노)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드 히드로클로리드,3-클로로-N-{4-[2-(1-이미다졸릴)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드 히드로클로리드,3-클로로-2-메틸-N-{4-[2-(4-메틸-1-피페라지닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,3-클로로-2-메틸-N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 디히드로클로리드,3-클로로-2-메틸-N-{4-[(4-모르폴리닐)메틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,2,4,6-트리클로로-N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,2,4-디클로로-N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,2,4-디클로로-6-메틸-N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드 히드로클로리드,N-{4-[2-(4-모르폴리닐)에틸]-1,3-티아졸-2-일}-4-프로필벤젠설폰아미드 디히드로클로리드,3-클로로-N-{4-[2-(에틸아미노)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드,3-클로로-N-(4-{2-[(2-히드록시에틸)아미노]에틸}-1,3-티아졸-2-일)-2-메틸벤젠설폰아미드,N-[2-(2-{[(3-클로로-2-메틸페닐)설포닐]아미노}-1,3-티아졸-4-일)에틸]-N- 에틸아세트아미드,3-클로로-2-메틸-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-N-{4-[2-(2-히드록시-3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드,2,4-디클로로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-l,3-티아졸-2-일}벤젠설폰아미드,2,4-디클로로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}-6-메틸벤젠설폰아미드,N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-l,3-티아졸-2-일}-2,4,6-트리클로로벤 젠설폰아미드,4,5-디클로로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}-2-티에닐설폰아미드,N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}-4-페녹시벤젠설폰아미드,3-플루오로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-l,3-티아졸-2-일}-5-(2-피리딜)-2-티에닐설폰아미드,4-아세틸아미노-3-클로로-N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,N-{4-[(3-옥소-4-모르폴리닐)메틸]-1,3-티아졸-2-일}-3-클로로-2-메틸벤젠설폰아미드,N-{4-[3-(3-옥소-4-모르폴리닐)프로필]-1,3-티아졸-2-일}-3-클로로-2-메틸벤젠설폰아미드,N-{4-[2-(3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2-일},N-메틸-3-클로로-2-메틸벤젠설폰아미드,3-클로로-2-메틸-N-4-[2-(2-메틸-3-옥소-4-모르폴리닐)에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,N-{4-[2-(아세틸아미노)에틸]-1,3-티아졸-2-일}-3-클로로-2-메틸-벤젠설폰아 미드,3-클로로-2-메틸-N-{4-[2-(4-(3-옥소-1,4-옥사제피닐)에틸]-1,3-티아졸-2- 일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(1-피롤리도닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(1-(2-옥소이미다졸리닐))에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(1-(2-옥소옥사졸리닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-N-{4-[2-(N-(2-푸릴카르보닐),N-2-히드록시에틸아미노)에틸]-1,3- 티아졸-2-일}-2-메틸벤젠설폰아미드,히드로클로리드,3-클로로-2-메틸-N-{4-[2-(4-메틸-2-옥소피페라지닐)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(메틸설포닐아미노)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(N-메틸,N-메틸설폰아미노)에틸]-1,3-티아졸-2-일} 벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(트리플루오로메틸설포닐아미노)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(N-메틸,N-트리플루오로메틸설폰아미노)에틸]-1, 3-티아졸-2-일}벤젠설폰아미드,3-클로로-2-메틸-N-{4-[2-(4-(1-메틸이미다졸릴)설포닐아미노)에틸]-1,3-티아졸-2-일}벤젠설폰아미드,3-클로로-N-{4-[2-(N-(3-클로로-2-메틸페닐설포닐),N-메틸아미노)에틸]-1, 3-티아졸-2-일}-2-메틸벤젠설폰아미드,N-[4-(2-브로모에틸)-1,3-티아졸-2-일]-3-클로로-2-메틸벤젠설폰아미드,3-클로로-N-[4-(2-클로로에틸)-1,3-티아졸-2-일]-2-메틸벤젠설폰아미드,3-클로로-2-메틸-N-{4-[(5-메틸-1,3,4-옥사디아졸-2-일)메틸]-1,3-티아졸-2- 일}벤젠설폰아미드, 및3-클로로-N-{4-[2-(에톡시카르보닐)에틸]-1,3-티아졸-2-일}-2-메틸벤젠설폰아미드.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서, 지연 또는 손상된 상처 치유를 수반하는 의학적 질환의 치료 또는 예방 방법.
- 제 4 항에 있어서, 지연 또는 손상된 상처 치유를 수반하는 의학적 질환이 당뇨병인 방법.
- 제 4 항에 있어서, 지연 또는 손상된 상처 치유를 수반하는 의학적 질환이 글루코코티코이드로의 치료에 의해 초래되는 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서, 당뇨병성 궤양, 정맥성 궤양 또는 피부 궤양과 같은 만성적인 상처의 상처 치유 촉진 방법.
- 상처 치유 촉진을 위한 약품의 제조에서의 제 1 항 내지 제 3 항 중 어느 한 한에 정의된 화합물의 용도로서, 상기 화합물이 11-β-히드록시스테로이드 탈수소효소 타입 1 의 억제제인 용도.
- 제 8 항에 있어서, 지연 또는 손상된 상처 치유를 수반하는 의학적 질환의 치료 또는 예방을 위한 약품 제조의 용도.
- 제 9 항에 있어서, 지연 또는 손상된 상처 치유를 수반하는 의학적 질환이 당뇨병인 용도.
- 제 9 항에 있어서, 지연 또는 손상된 상처 치유를 수반하는 의학적 질환이 글루코코티코이드로의 치료에 의해 초래되는 용도.
- 제 8 항에 있어서, 당뇨병성 궤양, 정맥성 궤양 또는 피부 궤양과 같은 만성적인 상처의 상처 치유 촉진을 위한 약품 제조의 용도.
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| PH10639A (en) * | 1967-07-17 | 1977-07-22 | Research Corp | Method of treatment and composition containing silver sulfadiazine |
| NZ306734A (ko) * | 1995-04-04 | 2000-01-28 | Texas Biotechnology Corp | |
| JP2001503037A (ja) * | 1996-10-16 | 2001-03-06 | アメリカン・サイアナミド・カンパニー | マトリクス金属プロテナイーゼおよびｔａｃｅに対する阻害薬としてのオルト―スルホンアミドヘテロアリールヒドロキサム酸の製造および使用 |
| SE0001899D0 (sv) * | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
-
2003
- 2003-06-25 SE SE0301882A patent/SE0301882D0/xx unknown
-
2004
- 2004-06-21 EP EP04749034A patent/EP1638553A1/en not_active Withdrawn
- 2004-06-21 KR KR1020057024626A patent/KR20060023570A/ko not_active Withdrawn
- 2004-06-21 WO PCT/SE2004/000996 patent/WO2004112784A1/en not_active Ceased
- 2004-06-21 CA CA002529406A patent/CA2529406A1/en not_active Abandoned
- 2004-06-21 AU AU2004249099A patent/AU2004249099A1/en not_active Abandoned
- 2004-06-21 JP JP2006517048A patent/JP2007521264A/ja active Pending
- 2004-06-21 CN CNA2004800177434A patent/CN1812784A/zh active Pending
-
2006
- 2006-01-25 NO NO20060416A patent/NO20060416L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004112784A1 (en) | 2004-12-29 |
| NO20060416L (no) | 2006-03-24 |
| JP2007521264A (ja) | 2007-08-02 |
| AU2004249099A1 (en) | 2004-12-29 |
| CA2529406A1 (en) | 2004-12-29 |
| SE0301882D0 (sv) | 2003-06-25 |
| EP1638553A1 (en) | 2006-03-29 |
| CN1812784A (zh) | 2006-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20051222 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |