JP2003534336A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2003534336A5 JP2003534336A5 JP2001586278A JP2001586278A JP2003534336A5 JP 2003534336 A5 JP2003534336 A5 JP 2003534336A5 JP 2001586278 A JP2001586278 A JP 2001586278A JP 2001586278 A JP2001586278 A JP 2001586278A JP 2003534336 A5 JP2003534336 A5 JP 2003534336A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazol
- amino
- ethyl
- 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.)
- Abandoned
Links
- -1 di-substituted amide Chemical class 0.000 description 222
- 229910052739 hydrogen Inorganic materials 0.000 description 28
- 239000001257 hydrogen Substances 0.000 description 26
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- 150000002431 hydrogen Chemical group 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 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 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
- 125000002757 morpholinyl group Chemical group 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000004391 aryl sulfonyl group Chemical class 0.000 description 4
- 125000004104 aryloxy group Chemical class 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 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 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
- 125000006700 (C1-C6) alkylthio 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
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 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 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 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 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 description 2
- RBJALPGWPKFZJQ-UHFFFAOYSA-N 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethyl-n-methylacetamide Chemical compound CCN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 RBJALPGWPKFZJQ-UHFFFAOYSA-N 0.000 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 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 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 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 description 2
- OQUSPHXWLUOJKV-UHFFFAOYSA-N 2-[2-[(3-chloro-2-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(=C(Cl)C=CC=2)C)=N1 OQUSPHXWLUOJKV-UHFFFAOYSA-N 0.000 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 description 2
- NKUJXDCGXSYHFM-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NKUJXDCGXSYHFM-UHFFFAOYSA-N 0.000 description 2
- QOLLTXJGTDTYQY-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-dipropylacetamide Chemical compound CCCN(CCC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 QOLLTXJGTDTYQY-UHFFFAOYSA-N 0.000 description 2
- DGWGQUBCSAZGGX-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-cyclohexyl-n-methylacetamide Chemical compound C=1SC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=NC=1CC(=O)N(C)C1CCCCC1 DGWGQUBCSAZGGX-UHFFFAOYSA-N 0.000 description 2
- NSBLVGFETONCLJ-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethyl-n-methylacetamide Chemical compound CCN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NSBLVGFETONCLJ-UHFFFAOYSA-N 0.000 description 2
- MWLVRQCUVOUIBF-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethylacetamide Chemical compound CCNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 MWLVRQCUVOUIBF-UHFFFAOYSA-N 0.000 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 description 2
- RPZCXMXPXXVKKM-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methyl-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CC(N=1)=CSC=1NS(=O)(=O)C1=CC=CC(Cl)=C1C RPZCXMXPXXVKKM-UHFFFAOYSA-N 0.000 description 2
- NSIMZMOFHFLYCX-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methyl-n-propan-2-ylacetamide Chemical compound CC(C)N(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NSIMZMOFHFLYCX-UHFFFAOYSA-N 0.000 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 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 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 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 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 description 2
- LPCMLZYSJNPYRP-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-phenylacetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)NC=2C=CC=CC=2)=CS1 LPCMLZYSJNPYRP-UHFFFAOYSA-N 0.000 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 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 description 2
- LUYHJLGAOMXVJE-UHFFFAOYSA-N 2-chloro-5-[[4-(2-ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]sulfamoyl]-4-fluorobenzoic acid Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=C(C(O)=O)C=2)F)=N1 LUYHJLGAOMXVJE-UHFFFAOYSA-N 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 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 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 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 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 description 2
- GQMBSMSODYSGSD-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(morpholin-4-ylmethyl)-1,3-thiazol-2-yl]benzenesulfonamide;hydrochloride Chemical compound Cl.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CN2CCOCC2)=CS1 GQMBSMSODYSGSD-UHFFFAOYSA-N 0.000 description 2
- SKFUKFDKZSDFRR-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound O1C(C)=NN=C1CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 SKFUKFDKZSDFRR-UHFFFAOYSA-N 0.000 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 description 2
- WVMIWCKHGQQDRE-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2C(OCC2)=O)=CS1 WVMIWCKHGQQDRE-UHFFFAOYSA-N 0.000 description 2
- PHBNCWNLQYXOBD-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2C(CCC2)=O)=CS1 PHBNCWNLQYXOBD-UHFFFAOYSA-N 0.000 description 2
- UQQKCMWRIVOYAN-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(3-oxo-1,4-oxazepan-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2C(COCCC2)=O)=CS1 UQQKCMWRIVOYAN-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- NZQVGMPKUSPJFJ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(methylamino)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CNCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NZQVGMPKUSPJFJ-UHFFFAOYSA-N 0.000 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 description 2
- MWZDUDLJCVHQQA-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-[methyl(methylsulfonyl)amino]ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CS(=O)(=O)N(C)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 MWZDUDLJCVHQQA-UHFFFAOYSA-N 0.000 description 2
- AKQKZSLUWUYCND-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-[methyl(trifluoromethylsulfonyl)amino]ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(C)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 AKQKZSLUWUYCND-UHFFFAOYSA-N 0.000 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 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 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 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 description 2
- MIBSEMNJJNDMIY-UHFFFAOYSA-N 3-chloro-n-[4-(2-imidazol-1-ylethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide;dihydrate Chemical compound O.O.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2C=NC=C2)=CS1 MIBSEMNJJNDMIY-UHFFFAOYSA-N 0.000 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 description 2
- UOTYWFJEHQSZLC-UHFFFAOYSA-N 3-chloro-n-[4-(3-hydroxypropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCO)=CS1 UOTYWFJEHQSZLC-UHFFFAOYSA-N 0.000 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 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 description 2
- XXJRBYRRYDXBAK-UHFFFAOYSA-N 3-chloro-n-[4-[2-(3,4-dihydro-1h-isoquinolin-2-yl)-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CC3=CC=CC=C3CC2)=CS1 XXJRBYRRYDXBAK-UHFFFAOYSA-N 0.000 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 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 description 2
- CUVAORAJJTXNTP-GFCCVEGCSA-N 3-chloro-n-[4-[2-[(2r)-2,4-dimethylpiperazin-1-yl]-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C[C@@H]1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 CUVAORAJJTXNTP-GFCCVEGCSA-N 0.000 description 2
- BZJKTWZDZSLMID-UHFFFAOYSA-N 3-chloro-n-[4-[3-(2-hydroxyethylamino)propyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide;hydrate;hydrochloride Chemical compound O.Cl.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCNCCO)=CS1 BZJKTWZDZSLMID-UHFFFAOYSA-N 0.000 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 description 2
- APQOEJCRFPFNBZ-UHFFFAOYSA-N 4-[4-[[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]sulfamoyl]phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 APQOEJCRFPFNBZ-UHFFFAOYSA-N 0.000 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 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 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
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000001769 aryl amino group Chemical class 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 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 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- OBFRWCVXUAAEQG-UHFFFAOYSA-N ethyl 2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=N1 OBFRWCVXUAAEQG-UHFFFAOYSA-N 0.000 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 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 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 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 description 2
- FFIWDZOIZSYFCK-UHFFFAOYSA-N ethyl 2-[2-[(2,3,4-trifluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(F)C(F)=CC=2)F)=N1 FFIWDZOIZSYFCK-UHFFFAOYSA-N 0.000 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 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 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 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 description 2
- PWVFWMRVAJPZQZ-UHFFFAOYSA-N ethyl 2-[2-[(2,4,6-trimethylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 PWVFWMRVAJPZQZ-UHFFFAOYSA-N 0.000 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 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 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 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 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 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 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 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 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 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 description 2
- IWJABBCLSCEYRG-UHFFFAOYSA-N ethyl 2-[2-[(2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)C)=N1 IWJABBCLSCEYRG-UHFFFAOYSA-N 0.000 description 2
- LNAGTOPKTFQIIS-UHFFFAOYSA-N ethyl 2-[2-[(2-methylsulfonylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)S(C)(=O)=O)=N1 LNAGTOPKTFQIIS-UHFFFAOYSA-N 0.000 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 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 description 2
- PFPFBIQZBIPXNF-UHFFFAOYSA-N ethyl 2-[2-[(3,4-dimethoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(OC)C(OC)=CC=2)=N1 PFPFBIQZBIPXNF-UHFFFAOYSA-N 0.000 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 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 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 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 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 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 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 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 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 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 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 description 2
- GTGYIXMGPVAEAW-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2,5-difluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=C(F)C=2)F)=N1 GTGYIXMGPVAEAW-UHFFFAOYSA-N 0.000 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 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 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 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 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 description 2
- CDXAXVDUNJWIEK-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2,1,3-benzoxadiazol-7-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=NON=C3C(Cl)=CC=2)=N1 CDXAXVDUNJWIEK-UHFFFAOYSA-N 0.000 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 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 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 description 2
- MHIBAPFQSMMVMN-UHFFFAOYSA-N ethyl 2-[2-[(4-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(F)=CC=2)=N1 MHIBAPFQSMMVMN-UHFFFAOYSA-N 0.000 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 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 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 description 2
- OGXYMEROVHKCKW-UHFFFAOYSA-N ethyl 2-[2-[(4-methylsulfonylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 OGXYMEROVHKCKW-UHFFFAOYSA-N 0.000 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 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 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 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 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 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 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 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 description 2
- GJLFAKWHOGZISU-UHFFFAOYSA-N ethyl 2-[2-[[2-(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 GJLFAKWHOGZISU-UHFFFAOYSA-N 0.000 description 2
- FAJOFAUMOBXWQR-UHFFFAOYSA-N ethyl 2-[2-[[2-methyl-4-(trifluoromethoxy)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(OC(F)(F)F)=CC=2)C)=N1 FAJOFAUMOBXWQR-UHFFFAOYSA-N 0.000 description 2
- FLDPZLUGDUXEOR-UHFFFAOYSA-N ethyl 2-[2-[[3-(trifluoromethyl)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=N1 FLDPZLUGDUXEOR-UHFFFAOYSA-N 0.000 description 2
- DAFDNRSHQQFNSQ-UHFFFAOYSA-N ethyl 2-[2-[[4-(3-chloro-2-cyanophenoxy)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC=3C(=C(Cl)C=CC=3)C#N)=CC=2)=N1 DAFDNRSHQQFNSQ-UHFFFAOYSA-N 0.000 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 description 2
- AXHPKOPJFWOGEG-UHFFFAOYSA-N ethyl 2-[2-[[4-(trifluoromethoxy)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC(F)(F)F)=CC=2)=N1 AXHPKOPJFWOGEG-UHFFFAOYSA-N 0.000 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 description 2
- SEMYPGMDNTYNAW-UHFFFAOYSA-N ethyl 2-[2-[[5-(1,2-oxazol-3-yl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C2=NOC=C2)=N1 SEMYPGMDNTYNAW-UHFFFAOYSA-N 0.000 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 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 description 2
- REWJMTLJYJXMPA-UHFFFAOYSA-N ethyl 2-[2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)=N1 REWJMTLJYJXMPA-UHFFFAOYSA-N 0.000 description 2
- JPINMSJPGIZMAC-UHFFFAOYSA-N ethyl 2-[2-[[5-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C2=NN(C)C(=C2)C(F)(F)F)=N1 JPINMSJPGIZMAC-UHFFFAOYSA-N 0.000 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 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 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 description 2
- RWZWQUOQHYQFEY-UHFFFAOYSA-N ethyl 4-[[2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 RWZWQUOQHYQFEY-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 2
- 125000005368 heteroarylthio group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 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 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 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 description 2
- ZTUGURUGCPZKNN-UHFFFAOYSA-N methyl 2-[2-[(4-chlorophenyl)sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 ZTUGURUGCPZKNN-UHFFFAOYSA-N 0.000 description 2
- QAJVSRSYPVAURA-UHFFFAOYSA-N methyl 2-[2-[[4-(3-chloro-2-cyanophenoxy)phenyl]sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC(Cl)=C1C#N QAJVSRSYPVAURA-UHFFFAOYSA-N 0.000 description 2
- ZYBLYLRTWNHTON-UHFFFAOYSA-N methyl 2-[5-methyl-2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl ZYBLYLRTWNHTON-UHFFFAOYSA-N 0.000 description 2
- XGRFANQSTSFERT-UHFFFAOYSA-N methyl 2-[5-methyl-2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 XGRFANQSTSFERT-UHFFFAOYSA-N 0.000 description 2
- MSZAVOUFPRGJAK-UHFFFAOYSA-N n,n-diethyl-2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CCN(CC)C(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 MSZAVOUFPRGJAK-UHFFFAOYSA-N 0.000 description 2
- BHIDMTIWLFOOCH-UHFFFAOYSA-N n-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNS(=O)(=O)C=2N=CN(C)C=2)=CS1 BHIDMTIWLFOOCH-UHFFFAOYSA-N 0.000 description 2
- UFEUINZZSPOMIB-UHFFFAOYSA-N n-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl]-n-(2-hydroxyethyl)furan-2-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN(CCO)C(=O)C=2OC=CC=2)=CS1 UFEUINZZSPOMIB-UHFFFAOYSA-N 0.000 description 2
- NHJOUIXWKCQUBU-UHFFFAOYSA-N n-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl]-n-ethylacetamide Chemical compound CCN(C(C)=O)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NHJOUIXWKCQUBU-UHFFFAOYSA-N 0.000 description 2
- ZJQKUCRCTKWOGH-UHFFFAOYSA-N n-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl]-n-methylcyclopropanecarboxamide Chemical compound C1CC1C(=O)N(C)CCC(N=1)=CSC=1NS(=O)(=O)C1=CC=CC(Cl)=C1C ZJQKUCRCTKWOGH-UHFFFAOYSA-N 0.000 description 2
- IERVETIQARVCNC-UHFFFAOYSA-N n-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl]acetamide Chemical compound CC(=O)NCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 IERVETIQARVCNC-UHFFFAOYSA-N 0.000 description 2
- LWXASGPYUQKPDV-UHFFFAOYSA-N n-[2-chloro-4-[[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=C(Cl)C(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 LWXASGPYUQKPDV-UHFFFAOYSA-N 0.000 description 2
- RGRYQXXKBMGOMW-UHFFFAOYSA-N n-[4-(2-aminoethyl)-1,3-thiazol-2-yl]-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN)=CS1 RGRYQXXKBMGOMW-UHFFFAOYSA-N 0.000 description 2
- HDGAICTWOOQDHI-UHFFFAOYSA-N n-[4-(2-azidoethyl)-1,3-thiazol-2-yl]-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN=[N+]=[N-])=CS1 HDGAICTWOOQDHI-UHFFFAOYSA-N 0.000 description 2
- DIVHULOBFPKRPY-UHFFFAOYSA-N n-[4-(2-bromoethyl)-1,3-thiazol-2-yl]-3-chloro-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCBr)=CS1 DIVHULOBFPKRPY-UHFFFAOYSA-N 0.000 description 2
- KDBCMBSJLWWVBF-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-phenoxybenzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 KDBCMBSJLWWVBF-UHFFFAOYSA-N 0.000 description 2
- UXGQHVGRHUTAKE-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 UXGQHVGRHUTAKE-UHFFFAOYSA-N 0.000 description 2
- ULPWFZWHDRXKJM-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 ULPWFZWHDRXKJM-UHFFFAOYSA-N 0.000 description 2
- MRMBTSXGNCSWEL-UHFFFAOYSA-N n-[4-(2-morpholin-4-ylethyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide;hydrochloride Chemical compound Cl.C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CCN2CCOCC2)=CS1 MRMBTSXGNCSWEL-UHFFFAOYSA-N 0.000 description 2
- IQYUHYFDRRCXDI-UHFFFAOYSA-N n-[4-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound C1CCCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 IQYUHYFDRRCXDI-UHFFFAOYSA-N 0.000 description 2
- PEXLPZAFFFVDLN-UHFFFAOYSA-N n-[4-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCCCC2)=CS1 PEXLPZAFFFVDLN-UHFFFAOYSA-N 0.000 description 2
- DHGMBKNUQFOXNJ-UHFFFAOYSA-N n-[4-(2-oxo-2-thiomorpholin-4-ylethyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound C1CSCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DHGMBKNUQFOXNJ-UHFFFAOYSA-N 0.000 description 2
- GHPAJYUHXJJXPB-UHFFFAOYSA-N n-[4-(2-oxo-2-thiomorpholin-4-ylethyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCSCC2)=CS1 GHPAJYUHXJJXPB-UHFFFAOYSA-N 0.000 description 2
- YDLJYKPHLDWGPU-UHFFFAOYSA-N n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]-5-pyridin-2-ylthiophene-2-sulfonamide Chemical compound O=C1COCCN1CCC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C=2N=CC=CC=2)=N1 YDLJYKPHLDWGPU-UHFFFAOYSA-N 0.000 description 2
- YBVGJQHCLCAYNI-UHFFFAOYSA-N n-[4-[2-(4-acetylpiperazin-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]-3-chloro-2-methylbenzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YBVGJQHCLCAYNI-UHFFFAOYSA-N 0.000 description 2
- ZGFGGMMCEBVIEZ-UHFFFAOYSA-N n-[5-methyl-4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound N=1C(CC(=O)N2CCOCC2)=C(C)SC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZGFGGMMCEBVIEZ-UHFFFAOYSA-N 0.000 description 2
- SMNHFSUWUBCFBM-UHFFFAOYSA-N n-benzyl-2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethylacetamide Chemical compound C=1SC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=NC=1CC(=O)N(CC)CC1=CC=CC=C1 SMNHFSUWUBCFBM-UHFFFAOYSA-N 0.000 description 2
- QZOYSGLQCQUNIH-UHFFFAOYSA-N n-benzyl-2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound C=1SC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=NC=1CC(=O)N(C)CC1=CC=CC=C1 QZOYSGLQCQUNIH-UHFFFAOYSA-N 0.000 description 2
- NSBJXAREJWGDLL-UHFFFAOYSA-N n-ethyl-n-methyl-2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CCN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 NSBJXAREJWGDLL-UHFFFAOYSA-N 0.000 description 2
- JLCVXVYTCBEECT-UHFFFAOYSA-N n-methyl-2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-propan-2-ylacetamide Chemical compound CC(C)N(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 JLCVXVYTCBEECT-UHFFFAOYSA-N 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- KTNAKTBGOFTHKY-UHFFFAOYSA-N tert-butyl 4-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetyl]piperazine-1-carboxylate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=CS1 KTNAKTBGOFTHKY-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 1
- 125000006516 2-(benzyloxy)ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NVJSIBKMBSOZJK-UHFFFAOYSA-N 3-chloro-n-[4-[2-(2-hydroxy-3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2C(C(O)OCC2)=O)=CS1 NVJSIBKMBSOZJK-UHFFFAOYSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 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
- 208000013016 Hypoglycemia 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
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000021235 carbamoylation Effects 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
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- DGMIUIWULBYPQP-UHFFFAOYSA-N ethyl 2-[2-[(5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=CC=2)=N1 DGMIUIWULBYPQP-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 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
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- PKQBQRASDIOPOK-UHFFFAOYSA-N n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]-4-phenoxybenzenesulfonamide Chemical compound O=C1COCCN1CCC1=CSC(NS(=O)(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 PKQBQRASDIOPOK-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940124597 therapeutic agent Drugs 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 |
|---|---|---|---|
| SE0001899A SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | New compounds |
| SE0001899-4 | 2000-05-22 | ||
| PCT/SE2001/001155 WO2001090090A1 (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003534336A JP2003534336A (ja) | 2003-11-18 |
| JP2003534336A5 true JP2003534336A5 (enExample) | 2008-05-29 |
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 |
| 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 |
| 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 |
| 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 After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
| 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) | US7030135B2 (enExample) |
| EP (4) | EP1283832B1 (enExample) |
| JP (4) | JP2003534336A (enExample) |
| KR (4) | KR20030016269A (enExample) |
| CN (4) | CN1188403C (enExample) |
| AR (1) | AR033534A1 (enExample) |
| AT (2) | ATE485283T1 (enExample) |
| AU (6) | AU2001262831B9 (enExample) |
| BR (1) | BR0111099A (enExample) |
| CA (4) | CA2408144C (enExample) |
| DE (3) | DE1283831T1 (enExample) |
| EA (1) | EA005274B1 (enExample) |
| ES (1) | ES2333846T3 (enExample) |
| HU (1) | HUP0302435A3 (enExample) |
| IL (4) | IL152670A0 (enExample) |
| MX (1) | MXPA02011632A (enExample) |
| NO (4) | NO20025588L (enExample) |
| NZ (4) | NZ522506A (enExample) |
| PE (1) | PE20020100A1 (enExample) |
| PL (1) | PL360137A1 (enExample) |
| SE (1) | SE0001899D0 (enExample) |
| WO (5) | WO2001090093A1 (enExample) |
| ZA (4) | ZA200209359B (enExample) |
Families Citing this family (192)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
| AU2001276378A1 (en) * | 2000-07-05 | 2002-01-14 | Bayer Aktiengesellschaft | Regulation of human 11 beta-hydroxysteroid dehydrogenase 1-like enzyme |
| GB0107383D0 (en) * | 2001-03-23 | 2001-05-16 | Univ Edinburgh | Lipid profile modulation |
| IL160630A0 (en) * | 2001-11-22 | 2004-07-25 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| CN1564816A (zh) | 2001-11-22 | 2005-01-12 | 比奥维特罗姆股份公司 | 11－β－羟基类固醇脱氢酶1型抑制剂 |
| RS44304A (sr) * | 2001-11-22 | 2007-06-04 | Biovitrum Ab., | Inhibitori 11-beta- hidroksistereoidne dehidrogenaze tipa 1 |
| RS44204A (sr) | 2001-11-22 | 2007-06-04 | Biovitrum Ab., | Inhibitori 11-beta- hidroksistereoidne dehidrogenaze tipa 1 |
| EA200400709A1 (ru) * | 2001-11-22 | 2004-12-30 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
| AU2007205749B2 (en) * | 2001-11-22 | 2009-04-23 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| US7485655B2 (en) | 2002-01-16 | 2009-02-03 | University Of Virginia Patent Foundation | 2-Aminothiazole allosteric enhancers of A1 adenosine receptors |
| US7329683B2 (en) | 2002-02-01 | 2008-02-12 | Merck & Co., Inc. | 11-β-hydroxysteroid dehydrogenase 1 inhibitors useful for the treatment of diabetes, obesity and dyslipidemia |
| US7338969B2 (en) * | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
| MXPA04009414A (es) * | 2002-03-29 | 2005-01-25 | Schering Corp | Alquilacion estereoselectiva de piperazinas quirales 2-metil-4-protegidas. |
| US20030198965A1 (en) | 2002-04-19 | 2003-10-23 | Isis Pharmaceuticals Inc. | Antisense modulation of hydroxysteroid 11-beta dehydrogenase 1 expression |
| SE0201194D0 (sv) * | 2002-04-19 | 2002-04-19 | Astrazeneca Ab | New compounds |
| AR040241A1 (es) * | 2002-06-10 | 2005-03-23 | Merck & Co Inc | Inhibidores de la 11-beta-hidroxiesteroide deshidrogrenasa 1 para el tratamiento de la diabetes obesidad y dislipidemia |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| WO2004027047A2 (en) * | 2002-09-18 | 2004-04-01 | Hanauske-Abel Hartmut M | INHIBITORS OF 11β-HYDROXYSTEROID DEHYDROGENASE AND USES THEREFOR |
| BR0315166A (pt) * | 2002-10-11 | 2005-08-16 | Astrazeneca Ab | Uso de um composto ou de um sal farmaceuticamente aceitável do mesmo, composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, método para produzir um efeito inibidor de 11betahsd1 em um animal de sangue quente, tal como o homem, que necessita de tratamento |
| GB0224830D0 (en) | 2002-10-24 | 2002-12-04 | Sterix Ltd | Compound |
| KR20050059294A (ko) | 2002-10-24 | 2005-06-17 | 스테릭스 리미티드 | 11-베타-하이드록시 스테로이드 데하이드로게나제 형태 1및 형태 2의 억제제 |
| AU2003276458A1 (en) * | 2002-11-07 | 2004-06-07 | Astrazeneca Ab | 2-oxo-ethanesulfonamide derivates |
| PE20040693A1 (es) * | 2002-11-14 | 2004-11-23 | Novartis Ag | N-sulfonilaminotiazol como mediadores de la sulfatasa de esteroides |
| GB0226602D0 (en) * | 2002-11-14 | 2002-12-24 | Novartis Ag | Organic compounds |
| JO2397B1 (en) * | 2002-12-20 | 2007-06-17 | ميرك شارب اند دوم كوربوريشن | Terazol derivatives as beta-hydroxy steroid dihydrogenase-1 inhibitors |
| WO2004056744A1 (en) * | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| FR2849598B1 (fr) * | 2003-01-07 | 2006-09-22 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete, par augmentation du nombre de cellules des ilots de langerhans |
| FR2849599B1 (fr) * | 2003-01-07 | 2006-12-29 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete |
| TW200503994A (en) * | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| DE10314610A1 (de) | 2003-04-01 | 2004-11-04 | Aventis Pharma Deutschland Gmbh | Neues Diphenylazetidinon mit verbesserten physiologischen Eigenschaften, Verfahren zu dessen Herstellung, diese Verbindungen enthaltende Arzneimittel und dessen Verwendung |
| ES2338656T3 (es) | 2003-04-11 | 2010-05-11 | High Point Pharmaceuticals, Llc | Uso farmaceutico de 1,2,4-triazoles fusionados. |
| US7700583B2 (en) | 2003-04-11 | 2010-04-20 | High Point Pharmaceuticals, Llc | 11β-hydroxysteroid dehydrogenase type 1 active compounds |
| EP1618090A1 (en) * | 2003-04-11 | 2006-01-25 | Novo Nordisk A/S | 11ß-HYDROXYSTEROID DEHYDROGENASE TYPE 1 ACTIVE COMPOUNDS |
| EP1785424A3 (en) * | 2003-04-11 | 2009-12-23 | High Point Pharmaceuticals, LLC | Fused 1,2,4-triazoles and pharmaceutical uses thereof |
| US7501405B2 (en) | 2003-04-11 | 2009-03-10 | High Point Pharmaceuticals, Llc | Combination therapy using an 11β-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent for the treatment of metabolic syndrome and related diseases and disorders |
| US7173030B2 (en) | 2003-05-21 | 2007-02-06 | Biovitrum Ab | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 |
| AU2004240885A1 (en) * | 2003-05-21 | 2004-12-02 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type I |
| WO2004106294A2 (en) | 2003-05-29 | 2004-12-09 | Merck & Co., Inc. | Triazole derivatives as inhibitors of 11-beta hydroxysteroid dehydrogenase-1 |
| SE0301883D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use II |
| SE0301885D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use IV |
| SE0301882D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use I |
| SE0301884D0 (sv) * | 2003-06-25 | 2003-06-25 | Biovitrum Ab | New use III |
| WO2004113310A1 (en) * | 2003-06-25 | 2004-12-29 | Biovitrum Ab | Use of an inhibitor of 11-b-hydroxysteroid dehydrogenase type 1 compounds for promoting wound healing |
| WO2005028438A1 (ja) | 2003-09-22 | 2005-03-31 | Banyu Pharmaceutical Co., Ltd. | 新規ピペリジン誘導体 |
| GB0324792D0 (en) | 2003-10-23 | 2003-11-26 | Sterix Ltd | Compound |
| GB0325745D0 (en) * | 2003-11-05 | 2003-12-10 | Astrazeneca Ab | Chemical compounds |
| MXPA06007077A (es) * | 2003-12-19 | 2006-08-23 | Pfizer | Derivados de bencenosulfonilamino-piridin-2-ilo y compuestos relacionados como inhibidores de 11-beta-hidroxi esteroide deshidrogenasa tipo 1 para el tratamiento de diabetes y obesidad. |
| EP1703908A4 (en) | 2003-12-22 | 2009-07-08 | Amgen Inc | ARYLSULFONAMIDE COMPOUNDS AND RELATED APPLICATIONS |
| IN2012DN03023A (enExample) | 2004-01-26 | 2015-07-31 | Merck Sharp & Dohme | |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| JP2007261945A (ja) * | 2004-04-07 | 2007-10-11 | Taisho Pharmaceut Co Ltd | チアゾール誘導体 |
| US7402704B2 (en) | 2004-04-14 | 2008-07-22 | Amgen Inc. | Arylsulfones and uses related thereto |
| AU2005250336B2 (en) * | 2004-04-20 | 2011-06-09 | Amgen, Inc. | Arylsulfonamides and uses as hydroxysteroid dehydrogenase |
| GB0408771D0 (en) * | 2004-04-20 | 2004-05-26 | Sterix Ltd | Compound |
| WO2005108360A1 (en) | 2004-05-07 | 2005-11-17 | Janssen Pharmaceutica N.V. | Pyrrolidin-2-one and piperidin-2-one derivatives as 11-beta hydroxysteroid dehydrogenase inhibitors |
| US8686011B2 (en) | 2004-05-24 | 2014-04-01 | Amgen Inc. | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 |
| MY148480A (en) | 2004-05-24 | 2013-04-30 | Amgen Inc | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| JP4809339B2 (ja) | 2004-06-28 | 2011-11-09 | エフ．ホフマン−ラ ロシュ アーゲー | ピリミジン誘導体 |
| AU2005268899B2 (en) * | 2004-08-05 | 2009-09-24 | F. Hoffmann-La Roche Ag | Substituted N-acyl-2-aminothiazoles |
| JP5137574B2 (ja) | 2004-08-30 | 2013-02-06 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | １１−ベータヒドロキシステロイドヒドロゲナーゼ阻害剤としての三環式ラクタム誘導体 |
| DE602005017159D1 (de) | 2004-08-30 | 2009-11-26 | Janssen Pharmaceutica Nv | Oxysteroid-dehydrogenase-inhibitoren |
| JP5208505B2 (ja) | 2004-08-30 | 2013-06-12 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | １１−ベータヒドロキシステロイドデヒドロゲナーゼ阻害剤としてのｎ−２アダマンタニル−２−フェノキシ−アセトアミド誘導体 |
| HRP20090151T3 (en) * | 2004-09-29 | 2009-04-30 | F. Hoffmann - La Roche Ag | Indozolone derivatives as 11b-hsd1 inhibitors |
| CA2582276C (en) * | 2004-10-04 | 2011-09-13 | F. Hoffmann-La Roche Ag | Alkil-pyridines as 11-beta inhibitors for diabetes |
| CN103073460B (zh) * | 2004-10-14 | 2015-09-09 | Abbvie德国有限责任两合公司 | 适用于治疗对于多巴胺d3受体的调节有反应的疾病的芳基磺酰基甲基或芳基磺酰胺取代的芳族化合物 |
| CA2580690A1 (en) | 2004-10-21 | 2006-05-04 | Transtech Pharma, Inc. | Bissulfonamide compounds as agonists of galr1, compositions, and methods of use |
| EP1666467A1 (en) * | 2004-11-08 | 2006-06-07 | Evotec AG | 11Beta-HSD1 Inhibitors |
| EP1659113A1 (en) * | 2004-11-08 | 2006-05-24 | Evotec AG | Inhibitors of 11beta-hydroxy steroid dehydrogenase type 1 (11beta-HSD1) |
| WO2006051662A1 (ja) * | 2004-11-09 | 2006-05-18 | Taisho Pharmaceutical Co., Ltd. | チアゾール誘導体 |
| WO2006059507A1 (ja) * | 2004-11-30 | 2006-06-08 | Sankyo Company, Limited | 11β-HSD1アンチセンス化合物 |
| WO2006066109A2 (en) * | 2004-12-17 | 2006-06-22 | Takeda San Diego, Inc. | Hydroxysteroid dehydrogenase inhibitors |
| GB0506133D0 (en) * | 2005-03-24 | 2005-05-04 | Sterix Ltd | Compound |
| WO2006105127A2 (en) | 2005-03-31 | 2006-10-05 | Takeda San Diego, Inc. | Hydroxysteroid dehydrogenase inhibitors |
| ATE519744T1 (de) | 2005-04-05 | 2011-08-15 | Hoffmann La Roche | 1h-pyrazol-4-carbonsäure-amide, deren herstellung und verwendung als 11-beta-hydroxysteroid- dehydrogenase-hemmer |
| NZ562766A (en) | 2005-05-30 | 2011-03-31 | Banyu Pharma Co Ltd | Piperidine derivatives as histamine-H3 receptor antagonists |
| WO2006134481A1 (en) * | 2005-06-16 | 2006-12-21 | Pfizer Inc. | Inhibitors of 11-beta hydroxysteroid dehydrogenase type 1 |
| EP1893609B1 (en) * | 2005-06-16 | 2009-11-18 | Pfizer, Inc. | N-(pyridin-2-yl)-sulfonamide derivatives |
| EP1916239A4 (en) | 2005-08-10 | 2009-10-21 | Banyu Pharma Co Ltd | PYRIDOLVERBINDUNG |
| AU2006282260A1 (en) | 2005-08-24 | 2007-03-01 | Msd K.K. | Phenylpyridone derivative |
| US7622492B2 (en) | 2005-08-31 | 2009-11-24 | Hoffmann-La Roche Inc. | Pyrazolones as inhibitors of 11β-hydroxysteroid dehydrogenase |
| US20090264426A1 (en) | 2005-09-07 | 2009-10-22 | Shunji Sakuraba | Bicyclic aromatic substituted pyridone derivative |
| US8293900B2 (en) | 2005-09-29 | 2012-10-23 | Merck Sharp & Dohme Corp | Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators |
| JP2007099659A (ja) * | 2005-10-03 | 2007-04-19 | Toray Fine Chemicals Co Ltd | ピペラジンカルボン酸エステルの製造法 |
| CN101365690A (zh) * | 2005-10-12 | 2009-02-11 | 沃泰克斯药物股份有限公司 | 作为电压门控离子通道调控剂的联苯衍生物 |
| US20080255084A1 (en) | 2005-10-21 | 2008-10-16 | Randy Lee Webb | Combination of Organic Compounds |
| EP1944301A4 (en) | 2005-10-27 | 2012-01-04 | Msd Kk | NEW BENZOXATHIIN DERIVATIVES |
| CA2629018C (en) | 2005-11-10 | 2013-12-31 | Banyu Pharmaceutical Co., Ltd. | Aza-substituted spiro derivative |
| US20070110802A1 (en) * | 2005-11-15 | 2007-05-17 | Janan Jona | Wet granulation process |
| MX2008006530A (es) | 2005-11-22 | 2008-09-25 | Amgen Inc | Inhibidores de 11-beta-hidroxiesteroide deshidrogenasa tipo 1. |
| CN101365686A (zh) | 2005-12-21 | 2009-02-11 | 沃泰克斯药物股份有限公司 | 作为离子通道调节剂的杂环衍生物 |
| US20100048713A1 (en) * | 2006-01-06 | 2010-02-25 | Aarhus Universitet | Compounds acting on the serotonin transporter |
| KR101081293B1 (ko) | 2006-01-18 | 2011-11-08 | 에프. 호프만-라 로슈 아게 | 11 베타-에이치에스디1 억제제로서 티아졸 |
| JP5118692B2 (ja) * | 2006-04-24 | 2013-01-16 | イーライ リリー アンド カンパニー | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１の阻害剤としてのシクロヘキシル置換ピロリジノン |
| ATE473210T1 (de) * | 2006-04-24 | 2010-07-15 | Lilly Co Eli | Substituierte pyrrolidinone als hemmer von 11- beta-hydroxysteroiddehydrogenase 1 |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| CN101096363B (zh) * | 2006-06-27 | 2011-05-11 | 中国人民解放军军事医学科学院毒物药物研究所 | 2,4,5-三取代噻唑类化合物、其制备方法、药物组合物及其制药用途 |
| AU2007283113A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use |
| EP2698157B1 (en) | 2006-09-22 | 2015-05-20 | Merck Sharp & Dohme Corp. | Method of treatment using fatty acid synthesis inhibitors |
| WO2008038692A1 (en) | 2006-09-28 | 2008-04-03 | Banyu Pharmaceutical Co., Ltd. | Diaryl ketimine derivative |
| DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CN101668524B (zh) * | 2007-02-12 | 2012-10-24 | 阿斯利康(瑞典)有限公司 | 作为11-β-HSD1抑制剂的吡唑衍生物 |
| CA2675669C (en) | 2007-02-23 | 2015-05-26 | High Point Pharmaceuticals, Llc | Novel compounds |
| JP2010519240A (ja) | 2007-02-23 | 2010-06-03 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | １１−ベータ−ヒドロキシステロイドデヒドロゲナーゼの阻害剤としての、ｎ−アダマンチルベンズアミド |
| WO2008101885A1 (en) | 2007-02-23 | 2008-08-28 | High Point Pharmaceuticals, Llc | N-adamantyl benzamides as inhibitors of 11-beta-hydroxysteroid dehydrogenase |
| JP5361857B2 (ja) | 2007-03-23 | 2013-12-04 | ファイザー・リミテッド | イオンチャネルの阻害剤 |
| US8106086B2 (en) | 2007-04-02 | 2012-01-31 | Msd K.K. | Indoledione derivative |
| JP2010523692A (ja) * | 2007-04-11 | 2010-07-15 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | 新規合成物 |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
| EP2172453A4 (en) | 2007-06-27 | 2010-12-22 | Taisho Pharmaceutical Co Ltd | CONNECTION WITH 11-β-HSD1 INHIBITING ACTIVITY |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| EP2264026A4 (en) | 2008-03-06 | 2012-03-28 | Msd Kk | ALKYLAMINOPYRIDINDERIVATE |
| JPWO2009119726A1 (ja) | 2008-03-28 | 2011-07-28 | Ｍｓｄ株式会社 | メラニン凝集ホルモン受容体拮抗作用を有するジアリールメチルアミド誘導体 |
| CA2726917C (en) | 2008-06-04 | 2018-06-26 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US20110071129A1 (en) | 2008-06-19 | 2011-03-24 | Makoto Ando | Spirodiamine-diaryl ketoxime derivative |
| UY31968A (es) | 2008-07-09 | 2010-01-29 | Sanofi Aventis | Nuevos derivados heterocíclicos, sus procesos para su preparación, y sus usos terapéuticos |
| EP2321341B1 (en) | 2008-07-16 | 2017-02-22 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| WO2010013595A1 (ja) | 2008-07-30 | 2010-02-04 | 萬有製薬株式会社 | ５員－５員又は５員－６員縮環シクロアルキルアミン誘導体 |
| US8410284B2 (en) | 2008-10-22 | 2013-04-02 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| MX2011004551A (es) | 2008-10-30 | 2011-05-25 | Merck Sharp & Dohme | Antagonistas del receptor de orexina de isonicotinamida. |
| CA2741672A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| KR200452117Y1 (ko) * | 2008-11-10 | 2011-02-08 | 대성공업주식회사 | 휠체어용 브레이크 와이어 케이블 지지 브래킷 |
| MX2011005037A (es) | 2008-11-21 | 2011-06-16 | High Point Pharmaceuticals Llc | Compuestos de adamantilo benzamida. |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| ES2350077B1 (es) | 2009-06-04 | 2011-11-04 | Laboratorios Salvat, S.A. | Compuestos inhibidores de 11beta-hidroxiesteroide deshidrogenasa de tipo 1. |
| KR20120060207A (ko) | 2009-08-26 | 2012-06-11 | 사노피 | 신규한 결정성 헤테로방향족 플루오로글리코시드 수화물, 이들 화합물을 포함하는 약제 및 이들의 용도 |
| AU2011218830B2 (en) | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| US8513430B2 (en) | 2010-07-27 | 2013-08-20 | High Point Pharmaceuticals, Llc | Substituted thiazol-2-ylamine derivatives, pharmaceutical compositions, and methods of use as 11-beta HSD1 modulators |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| CA2826649C (en) | 2011-02-25 | 2016-07-26 | Merck Sharp & Dohme Corp. | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| EA201391254A1 (ru) | 2011-03-01 | 2014-02-28 | Синерджи Фармасьютикалз Инк. | Способ получения агонистов гуанилатциклазы c |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| AR088352A1 (es) | 2011-10-19 | 2014-05-28 | Merck Sharp & Dohme | Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina |
| CN103204824B (zh) * | 2012-01-12 | 2015-04-08 | 清华大学深圳研究生院 | 2-氨基噻唑-4-酰胺类衍生物及其制备方法与应用 |
| RU2015106909A (ru) | 2012-08-02 | 2016-09-27 | Мерк Шарп И Доум Корп. | Антидиабетические трициклические соединения |
| BR112015019836A2 (pt) | 2013-02-22 | 2017-07-18 | Merck Sharp & Dohme | composto, composição farmacêutica, e, uso de um composto |
| EP2970119B1 (en) | 2013-03-14 | 2021-11-03 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| WO2014151200A2 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| JP2016514671A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼのアゴニストおよびその使用 |
| TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
| CN105764916B (zh) | 2013-06-05 | 2021-05-18 | 博士医疗爱尔兰有限公司 | 鸟苷酸环化酶c的超纯激动剂、制备和使用所述激动剂的方法 |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| MX389591B (es) | 2014-08-29 | 2025-03-20 | Tes Pharma S R L | INHIBIDORES DE ACIDO A-AMINO-ß-CARBOXIMUCONICO SEMIALDEHIDO DESCARBOXILASA |
| US10208081B2 (en) | 2014-11-26 | 2019-02-19 | Enanta Pharmaceuticals, Inc. | Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof |
| CN105001152A (zh) * | 2015-07-19 | 2015-10-28 | 佛山市赛维斯医药科技有限公司 | 一类二甲胺基二吡啶叔醇结构的11β-HSD1抑制剂及其用途 |
| CN105017135A (zh) * | 2015-07-19 | 2015-11-04 | 佛山市赛维斯医药科技有限公司 | 一类二吡啶叔醇结构的11β-HSD1抑制剂、制备方法及其用途 |
| EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
| MX2019004321A (es) | 2016-10-14 | 2019-06-12 | Tes Pharma S R L | Inhibidores de la acido alfa-amino-beta-carboximuconico semialdehido descarboxilasa. |
| CN107663204A (zh) * | 2016-10-19 | 2018-02-06 | 首都医科大学附属北京世纪坛医院 | 一种化合物的抗结核应用 |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| US11505547B2 (en) | 2017-11-30 | 2022-11-22 | Step Pharma S.A.S. | Compounds |
| US11655246B2 (en) * | 2017-11-30 | 2023-05-23 | Step Pharma S.A.S. | Aminothiazole compounds as inhibitors of CTPS1 |
| EP3752510B1 (en) | 2018-02-15 | 2022-12-07 | Vertex Pharmaceuticals Incorporated | Macrocycles as modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions thereof, their use in the treatment of cycstic fibrosis, and process for making them |
| CN108358869B (zh) * | 2018-03-27 | 2019-09-10 | 河北师范大学 | 一种n-苯并噻唑基苯磺酰胺类衍生物、制备方法及用途 |
| CN108659219B (zh) * | 2018-06-08 | 2021-02-09 | 扬州大学 | 一种聚苯胺的制备方法 |
| WO2020033919A1 (en) | 2018-08-10 | 2020-02-13 | Diapin Therapeutics, Llc | Tri-peptides and treatment of metabolic, cardiovascular and inflammatory disorders |
| CN118496217A (zh) | 2018-11-20 | 2024-08-16 | Tes制药有限责任公司 | α-氨基-β-羧基己二烯二酸半醛去羧酶的抑制剂 |
| CN109748831A (zh) * | 2018-12-17 | 2019-05-14 | 南通正达农化有限公司 | 一种三氟甲磺酸三氟乙酯的制备方法 |
| US12331018B2 (en) | 2019-02-13 | 2025-06-17 | Merck Sharp & Dohme Llc | Pyrrolidine orexin receptor agonists |
| EP3924058B1 (en) | 2019-02-13 | 2026-01-07 | Merck Sharp & Dohme LLC | 5-alkyl pyrrolidine orexin receptor agonists |
| TWI848092B (zh) | 2019-04-03 | 2024-07-11 | 美商維泰克斯製藥公司 | 囊腫纖維化跨膜傳導調節蛋白調節劑 |
| US12312332B2 (en) | 2019-08-08 | 2025-05-27 | Merck Sharp & Dohme Llc | Heteroaryl pyrrolidine and piperidine orexin receptor agonists |
| KR20220064366A (ko) | 2019-08-14 | 2022-05-18 | 버텍스 파마슈티칼스 인코포레이티드 | Cftr 조절제의 결정질 형태 |
| TWI867024B (zh) | 2019-08-14 | 2024-12-21 | 美商維泰克斯製藥公司 | 囊腫纖維化跨膜傳導調節蛋白之調節劑 |
| TWI899097B (zh) | 2019-08-14 | 2025-10-01 | 美商維泰克斯製藥公司 | 製備cftr調節劑之方法 |
| US12545649B2 (en) | 2019-11-18 | 2026-02-10 | Vanderbilt University | WDR5-MYC inhibitors |
| CN111620837B (zh) * | 2020-06-29 | 2022-02-15 | 郑州大学 | 香柏酮噻唑酰胺类化合物、及其制备方法和应用 |
| US20230365533A1 (en) | 2020-08-18 | 2023-11-16 | Merck Sharp & Dohme Llc | Bicycloheptane pyrrolidine orexin receptor agonists |
| EP4225750A1 (en) * | 2020-10-07 | 2023-08-16 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| CN112451514A (zh) * | 2020-11-26 | 2021-03-09 | 江西农业大学 | 二氢杨梅素纳米硒及其制备方法和应用 |
| CA3204725A1 (en) | 2020-12-10 | 2022-06-16 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| CN113461635A (zh) * | 2021-07-07 | 2021-10-01 | 上海毕得医药科技股份有限公司 | 4-（2-氯乙基）噻唑-2-羧酸乙酯及其制备方法和应用 |
| CN118103038A (zh) | 2021-08-20 | 2024-05-28 | 英安塔制药有限公司 | 17β-羟基类固醇脱氢酶13型抑制剂及其使用方法 |
| CN117105824A (zh) * | 2023-08-26 | 2023-11-24 | 衢州市九洲化工有限公司 | 一种三氟甲磺酸三氟乙酯的制备方法 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB517272A (en) * | 1938-06-03 | 1940-01-25 | May & Baker Ltd | The preparation of new therapeutically useful heterocyclic compounds |
| GB620654A (en) | 1939-10-03 | 1949-03-29 | Chinoin Gyogyszer Es Vegyeszet | A process for the preparation of sulphonamide derivatives of 2-amino-thiazole |
| US2611770A (en) | 1949-04-16 | 1952-09-23 | American Cyanamid Co | N-(2-thiazolyl)-2-hydroxypyridine-5-sulfonamides |
| GB822947A (en) | 1957-01-25 | 1959-11-04 | Smith & Nephew | Improvements in and relating to sulphonamides |
| DE1620508A1 (de) * | 1965-07-23 | 1969-09-18 | Thomae Gmbh Dr K | Verfahren zur Herstellung neuer 4,5,6,7-Tetrahydrothiazolo-[5,4-c]-pyridine |
| CA1088049A (en) * | 1975-06-03 | 1980-10-21 | Takashi Masugi | 3-substituted-7-substituted alkanamido-3-cephem-4- carboxylic acid compounds and processes for preparation thereof |
| FR2384498A1 (fr) | 1975-11-26 | 1978-10-20 | Parcor | Nouveaux derives sulfonylamino thiazoliques et leurs applications en medecine humaine et veterinaire |
| EP0246749A3 (en) * | 1986-05-17 | 1988-08-31 | AgrEvo UK Limited | Triazole herbicides |
| US5591761A (en) | 1993-05-20 | 1997-01-07 | Texas Biotechnology Corporation | Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US5594021A (en) | 1993-05-20 | 1997-01-14 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US5962490A (en) * | 1987-09-25 | 1999-10-05 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| JPH021483A (ja) | 1988-03-10 | 1990-01-05 | Nippon Tokushu Noyaku Seizo Kk | 農業用殺菌剤 |
| JPH078863B2 (ja) | 1989-09-21 | 1995-02-01 | 久光製薬株式会社 | 新規なジフェニルチアゾール誘導体 |
| EP0532239B1 (en) | 1991-09-10 | 1995-12-13 | Zeneca Limited | Benzenesulphonamide derivatives as 5-lipoxygenase inhibitors |
| JPH0670024B2 (ja) | 1993-04-13 | 1994-09-07 | 塩野義製薬株式会社 | グルタコン酸エステル誘導体の製法 |
| US6030991A (en) | 1993-05-20 | 2000-02-29 | Texas Biotechnology Corp. | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| JPH07149745A (ja) * | 1993-11-30 | 1995-06-13 | Hisamitsu Pharmaceut Co Inc | 新規な２−アミノチアゾール誘導体 |
| JPH07149746A (ja) * | 1993-11-30 | 1995-06-13 | Hisamitsu Pharmaceut Co Inc | 新規な２−置換アミノチアゾール誘導体 |
| JPH07309757A (ja) * | 1994-05-18 | 1995-11-28 | Asahi Chem Ind Co Ltd | βアミロイド蛋白神経細胞毒性低減剤 |
| PT779810E (pt) | 1994-08-09 | 2003-11-28 | Cortendo Ab | Utilizacao de cetoconazole e substancias relacionadas em medicamentos para o tratamento da diabetes tipo ii |
| AU689972B2 (en) | 1994-11-29 | 1998-04-09 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/or salt thereof |
| SE505391C2 (sv) | 1995-05-30 | 1997-08-18 | Cortendo Ab | Användning av kortisol-agonister för framställning av ett system för diagnostisering av det metabola syndromet |
| GB9512697D0 (en) | 1995-06-22 | 1995-08-23 | Zeneca Ltd | Heterocyclic compounds |
| GB9517622D0 (en) | 1995-08-29 | 1995-11-01 | Univ Edinburgh | Regulation of intracellular glucocorticoid concentrations |
| WO1997047299A1 (en) * | 1996-06-12 | 1997-12-18 | 3-Dimensional Pharmaceuticals, Inc. | Amidino and guanidino heterocyclic protease inhibitors |
| US5877193A (en) | 1996-07-19 | 1999-03-02 | Hoffmann-La Roche Inc. | Use of N-(4-aryl-thiazol-2-yl)-sulfonamides |
| EP0934300B1 (en) | 1996-10-16 | 2002-12-18 | American Cyanamid Company | The preparation and use of ortho-sulfonamido heteroaryl hydroxamic acids as matrix metalloproteinase and tace inhibitors |
| DZ2376A1 (fr) | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
| SE9700642D0 (sv) | 1997-02-24 | 1997-02-24 | Kronvall Stefan Med Ab | Medel och sätt för förebyggande och behandling av det metabola syndromet |
| US5783597A (en) | 1997-03-04 | 1998-07-21 | Ortho Pharmaceutical Corporation | 2,5-disubstituted thiophenes: inhibitors of 5-lipoxygenase and inducible cyclooxygenase (COX-2) enzymes, composition and use |
| JP2002511097A (ja) | 1997-07-11 | 2002-04-09 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５−ｈｔ▲下６▼レセプターアンタゴニストであるスルホンアミド誘導体およびその製造方法 |
| GB9725141D0 (en) | 1997-11-27 | 1998-01-28 | Pharmacia & Upjohn Spa | Benzenesulfonamide compounds |
| CA2332325A1 (en) | 1998-06-18 | 1999-12-23 | Bristol-Myers Squibb Company | Carbon substituted aminothiazole inhibitors of cyclin dependent kinases |
| PL199236B1 (pl) | 1998-07-08 | 2008-08-29 | Sanofi Aventis Deutschland | N-Aryloamidy kwasów sulfonyloaminokarboksylowych podstawionych siarką, sposób ich wytwarzania, środek farmaceutyczny i zastosowanie N-aryloamidów kwasów sulfonyloaminokarboksylowych podstawionych siarką |
| GB9915625D0 (en) | 1999-07-02 | 1999-09-01 | Cortendo Ab | Method |
| GB0001449D0 (en) | 2000-01-21 | 2000-03-08 | Cortendo Ab | Compositions |
| IT1317735B1 (it) | 2000-01-26 | 2003-07-15 | Nicox Sa | Sali di agenti antimicrobici. |
| SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
| WO2002028353A2 (en) | 2000-10-05 | 2002-04-11 | Smithkline Beecham Corporation | Phosphate transport inhibitors |
| GB0118300D0 (en) | 2001-07-26 | 2001-09-19 | Cortendo Ab | Formulations |
| CN1564816A (zh) | 2001-11-22 | 2005-01-12 | 比奥维特罗姆股份公司 | 11－β－羟基类固醇脱氢酶1型抑制剂 |
| RS44304A (sr) | 2001-11-22 | 2007-06-04 | Biovitrum Ab., | Inhibitori 11-beta- hidroksistereoidne dehidrogenaze tipa 1 |
| RS44204A (sr) * | 2001-11-22 | 2007-06-04 | Biovitrum Ab., | Inhibitori 11-beta- hidroksistereoidne dehidrogenaze tipa 1 |
| EA200400709A1 (ru) * | 2001-11-22 | 2004-12-30 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
-
2000
- 2000-05-22 SE SE0001899A patent/SE0001899D0/xx unknown
-
2001
- 2001-05-18 PE PE2001000450A patent/PE20020100A1/es not_active Application Discontinuation
- 2001-05-22 JP JP2001586278A patent/JP2003534336A/ja not_active Abandoned
- 2001-05-22 US US10/296,132 patent/US7030135B2/en not_active Expired - Fee Related
- 2001-05-22 CA CA002408144A patent/CA2408144C/en not_active Expired - Fee Related
- 2001-05-22 WO PCT/SE2001/001154 patent/WO2001090093A1/en not_active Ceased
- 2001-05-22 WO PCT/SE2001/001157 patent/WO2001090094A1/en not_active Ceased
- 2001-05-22 CN CNB018099661A patent/CN1188403C/zh not_active Expired - Fee Related
- 2001-05-22 EP EP01934782A patent/EP1283832B1/en not_active Expired - Lifetime
- 2001-05-22 ES ES01937063T patent/ES2333846T3/es not_active Expired - Lifetime
- 2001-05-22 AU AU2001262831A patent/AU2001262831B9/en not_active Ceased
- 2001-05-22 WO PCT/SE2001/001155 patent/WO2001090090A1/en not_active Ceased
- 2001-05-22 NZ NZ522506A patent/NZ522506A/en unknown
- 2001-05-22 JP JP2001586279A patent/JP2003534337A/ja not_active Abandoned
- 2001-05-22 CN CN01809979A patent/CN1430614A/zh active Pending
- 2001-05-22 DE DE1283831T patent/DE1283831T1/de active Pending
- 2001-05-22 AU AU6093201A patent/AU6093201A/xx not_active Withdrawn
- 2001-05-22 US US10/296,552 patent/US7132436B2/en not_active Expired - Fee Related
- 2001-05-22 AT AT01934782T patent/ATE485283T1/de not_active IP Right Cessation
- 2001-05-22 EA EA200201271A patent/EA005274B1/ru not_active IP Right Cessation
- 2001-05-22 WO PCT/SE2001/001158 patent/WO2001090092A1/en not_active Ceased
- 2001-05-22 IL IL15267001A patent/IL152670A0/xx unknown
- 2001-05-22 US US10/296,553 patent/US7618961B2/en not_active Expired - Fee Related
- 2001-05-22 IL IL15266901A patent/IL152669A0/xx unknown
- 2001-05-22 NZ NZ522591A patent/NZ522591A/en unknown
- 2001-05-22 WO PCT/SE2001/001156 patent/WO2001090091A1/en not_active Ceased
- 2001-05-22 IL IL15279001A patent/IL152790A0/xx unknown
- 2001-05-22 AU AU2001262830A patent/AU2001262830A1/en not_active Abandoned
- 2001-05-22 CA CA002408142A patent/CA2408142C/en not_active Expired - Fee Related
- 2001-05-22 KR KR1020027015703A patent/KR20030016269A/ko not_active Withdrawn
- 2001-05-22 AU AU6093101A patent/AU6093101A/xx not_active Withdrawn
- 2001-05-22 PL PL36013701A patent/PL360137A1/xx not_active IP Right Cessation
- 2001-05-22 IL IL15275301A patent/IL152753A0/xx unknown
- 2001-05-22 EP EP01938885A patent/EP1283833A1/en not_active Withdrawn
- 2001-05-22 BR BR0111099-3A patent/BR0111099A/pt not_active IP Right Cessation
- 2001-05-22 NZ NZ522507A patent/NZ522507A/en unknown
- 2001-05-22 AU AU6283101A patent/AU6283101A/xx active Pending
- 2001-05-22 KR KR1020027015741A patent/KR20030011341A/ko not_active Withdrawn
- 2001-05-22 KR KR1020027015743A patent/KR20030016272A/ko not_active Withdrawn
- 2001-05-22 JP JP2001586280A patent/JP2003534338A/ja not_active Abandoned
- 2001-05-22 EP EP01934781A patent/EP1283831A1/en not_active Withdrawn
- 2001-05-22 DE DE60139931T patent/DE60139931D1/de not_active Expired - Lifetime
- 2001-05-22 CN CNB018116787A patent/CN1249039C/zh not_active Expired - Fee Related
- 2001-05-22 CN CN01811609A patent/CN1437588A/zh active Pending
- 2001-05-22 US US10/276,954 patent/US7125900B2/en not_active Expired - Fee Related
- 2001-05-22 AU AU6445601A patent/AU6445601A/xx not_active Withdrawn
- 2001-05-22 CA CA002408783A patent/CA2408783A1/en not_active Abandoned
- 2001-05-22 AR ARP010102421A patent/AR033534A1/es not_active Application Discontinuation
- 2001-05-22 AT AT01937063T patent/ATE443055T1/de not_active IP Right Cessation
- 2001-05-22 HU HU0302435A patent/HUP0302435A3/hu unknown
- 2001-05-22 KR KR1020027015742A patent/KR20030016271A/ko not_active Withdrawn
- 2001-05-22 EP EP01937063A patent/EP1283834B1/en not_active Expired - Lifetime
- 2001-05-22 DE DE60143293T patent/DE60143293D1/de not_active Expired - Lifetime
- 2001-05-22 CA CA2409697A patent/CA2409697C/en not_active Expired - Fee Related
- 2001-05-22 NZ NZ522538A patent/NZ522538A/en unknown
- 2001-05-22 JP JP2001586282A patent/JP2003534339A/ja not_active Abandoned
- 2001-05-22 MX MXPA02011632A patent/MXPA02011632A/es active IP Right Grant
-
2002
- 2002-11-18 ZA ZA200209359A patent/ZA200209359B/en unknown
- 2002-11-18 ZA ZA200209364A patent/ZA200209364B/en unknown
- 2002-11-18 ZA ZA200209362A patent/ZA200209362B/en unknown
- 2002-11-18 ZA ZA200209360A patent/ZA200209360B/en unknown
- 2002-11-21 NO NO20025588A patent/NO20025588L/no not_active Application Discontinuation
- 2002-11-21 NO NO20025586A patent/NO323832B1/no not_active IP Right Cessation
- 2002-11-21 NO NO20025587A patent/NO323779B1/no not_active IP Right Cessation
- 2002-11-21 NO NO20025585A patent/NO323831B1/no not_active IP Right Cessation
-
2005
- 2005-11-30 US US11/289,634 patent/US20060160797A1/en not_active Abandoned
-
2006
- 2006-08-29 US US11/511,224 patent/US20060287374A1/en not_active Abandoned
-
2009
- 2009-11-16 US US12/619,216 patent/US20100113435A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2003534336A5 (enExample) | ||
| CA2409697A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
| CA2466490A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
| US6150385A (en) | 1,3,4-thiadiazoles useful for the treatment of CMV infections | |
| WO2004103980A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type i | |
| CA2589271A1 (en) | Urea inhibitors of map kinases | |
| EP1152759A2 (en) | METHODS OF TREATING C1s-MEDIATED DISEASES AND CONDITIONS, AND COMPOUNDS AND COMPOSITIONS THEREFOR | |
| KR20050044578A (ko) | 11-베타-히드록시 스테로이드 탈수소효소 제 1 형의저해제 | |
| JP2005509677A (ja) | １型１１−ベータ−ヒドロキシステロイドデヒヒドロゲナーゼの阻害剤 | |
| CA2347188A1 (en) | 2-amino-thiazole derivatives, process for their preparation, and their use as antitumor agents | |
| NZ506507A (en) | Heteroaryl amidine, methylamidine or guanidine derivatives useful as urokinase inhibitors | |
| JPWO2002002542A1 (ja) | ５員環化合物 | |
| WO2002002542A1 (fr) | Compose annulaire a cinq chainons | |
| SK11422001A3 (sk) | Heteroarylamidíny, metylamidíny a guanidíny ako inhibítory proteázy | |
| JP2010533185A5 (enExample) | ||
| US20050009821A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
| ZA200401305B (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1. | |
| JP2003192591A (ja) | ５員環化合物からなる医薬 | |
| AU2001260931B2 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
| RU2007131275A (ru) | Производные n-[(4, 5-дифенил-2-тиенил)метил]сульфонамида, их получение и их применение в терапии | |
| ZA200401312B (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1. | |
| AU2001260931A1 (en) | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 | |
| JP2006169257A (ja) | ５員環化合物 | |
| RU2007115042A (ru) | Химические соединения |