DE1283831T1 - Inhibitoren der 11-beta-hydroxy-steroid-dehydrogenase des typs 1 - Google Patents
Inhibitoren der 11-beta-hydroxy-steroid-dehydrogenase des typs 1Info
- Publication number
- DE1283831T1 DE1283831T1 DE1283831T DE01934781T DE1283831T1 DE 1283831 T1 DE1283831 T1 DE 1283831T1 DE 1283831 T DE1283831 T DE 1283831T DE 01934781 T DE01934781 T DE 01934781T DE 1283831 T1 DE1283831 T1 DE 1283831T1
- Authority
- DE
- Germany
- 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.)
- Pending
Links
- 102000004277 11-beta-hydroxysteroid dehydrogenases Human genes 0.000 title claims 2
- 108090000874 11-beta-hydroxysteroid dehydrogenases Proteins 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title claims 2
- -1 aryloxy radicals Chemical class 0.000 claims 269
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 85
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 71
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 60
- 229910052739 hydrogen Inorganic materials 0.000 claims 39
- 239000001257 hydrogen Substances 0.000 claims 39
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
- 150000002431 hydrogen Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 150000001408 amides Chemical class 0.000 claims 11
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims 10
- 239000004305 biphenyl Substances 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 150000001412 amines Chemical class 0.000 claims 9
- 230000008878 coupling Effects 0.000 claims 9
- 238000010168 coupling process Methods 0.000 claims 9
- 238000005859 coupling reaction Methods 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- 125000002757 morpholinyl group Chemical group 0.000 claims 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 9
- 229940124530 sulfonamide Drugs 0.000 claims 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 6
- 125000004391 aryl sulfonyl group Chemical class 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 244000309464 bull Species 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 4
- JVFCCRJSBNUDDU-UHFFFAOYSA-N 4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 JVFCCRJSBNUDDU-UHFFFAOYSA-N 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 230000002519 immonomodulatory effect Effects 0.000 claims 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- KXYUTYUIHLDQAN-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 KXYUTYUIHLDQAN-UHFFFAOYSA-N 0.000 claims 3
- APWFGJZGVUNFET-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CC(=O)N2CCCCC2)=CS1 APWFGJZGVUNFET-UHFFFAOYSA-N 0.000 claims 3
- FEYIHTAVPXMQEK-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(2-oxo-2-thiomorpholin-4-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CC(=O)N2CCSCC2)=CS1 FEYIHTAVPXMQEK-UHFFFAOYSA-N 0.000 claims 3
- CGPRKKGTHPOISW-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 CGPRKKGTHPOISW-UHFFFAOYSA-N 0.000 claims 3
- UDSFXWYSYFILMF-UHFFFAOYSA-N 2,4,6-trichloro-n-[5-methyl-4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound N=1C(CC(=O)N2CCOCC2)=C(C)SC=1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl UDSFXWYSYFILMF-UHFFFAOYSA-N 0.000 claims 3
- FSWBELRWPNEUBN-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-[4-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CC(=O)N2CCCCC2)=CS1 FSWBELRWPNEUBN-UHFFFAOYSA-N 0.000 claims 3
- OHWFDVUOIJVLGT-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-[4-(2-oxo-2-thiomorpholin-4-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CC(=O)N2CCSCC2)=CS1 OHWFDVUOIJVLGT-UHFFFAOYSA-N 0.000 claims 3
- OCKUKOAKTSTSHL-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 OCKUKOAKTSTSHL-UHFFFAOYSA-N 0.000 claims 3
- VCZAXMJNUKICQT-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-[5-methyl-4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound N=1C(CC(=O)N2CCOCC2)=C(C)SC=1NS(=O)(=O)C1=C(C)C=C(Cl)C=C1Cl VCZAXMJNUKICQT-UHFFFAOYSA-N 0.000 claims 3
- IBGZNXCMLFPZRU-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 IBGZNXCMLFPZRU-UHFFFAOYSA-N 0.000 claims 3
- QUTPYRLKSYVDGL-UHFFFAOYSA-N 2,4-dichloro-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 QUTPYRLKSYVDGL-UHFFFAOYSA-N 0.000 claims 3
- JMBAHDKUIHPACC-UHFFFAOYSA-N 2-[2-(benzenesulfonamido)-1,3-thiazol-4-yl]-n-(cyclohexylmethyl)acetamide Chemical compound C1CCCCC1CNC(=O)CC(N=1)=CSC=1NS(=O)(=O)C1=CC=CC=C1 JMBAHDKUIHPACC-UHFFFAOYSA-N 0.000 claims 3
- JLAXYEKZOBHMQD-UHFFFAOYSA-N 2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CC1=CSC(NS(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=N1 JLAXYEKZOBHMQD-UHFFFAOYSA-N 0.000 claims 3
- WSKHSWHWEKUKCK-UHFFFAOYSA-N 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 WSKHSWHWEKUKCK-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- JBKXGULGNQEDPS-UHFFFAOYSA-N 2-[2-[(2,4-difluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethylacetamide Chemical compound CCNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)F)=N1 JBKXGULGNQEDPS-UHFFFAOYSA-N 0.000 claims 3
- WYWISWQMNVHCCM-UHFFFAOYSA-N 2-[2-[(2,5-dichlorothiophen-3-yl)sulfonylamino]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CSC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=N1 WYWISWQMNVHCCM-UHFFFAOYSA-N 0.000 claims 3
- HEMVPFSRVDOYIS-UHFFFAOYSA-N 2-[2-[(2,5-dichlorothiophen-3-yl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=N1 HEMVPFSRVDOYIS-UHFFFAOYSA-N 0.000 claims 3
- AJWZZHZNTINJCH-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 AJWZZHZNTINJCH-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- 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 claims 3
- HCVDPOLLLJHUPC-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 HCVDPOLLLJHUPC-UHFFFAOYSA-N 0.000 claims 3
- ZFZSPBPBECULLJ-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-phenylacetamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)NC=2C=CC=CC=2)=CS1 ZFZSPBPBECULLJ-UHFFFAOYSA-N 0.000 claims 3
- PBNMKZXABHYGGL-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(N)=O)=CS1 PBNMKZXABHYGGL-UHFFFAOYSA-N 0.000 claims 3
- WBXQHDLZILRZTA-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WBXQHDLZILRZTA-UHFFFAOYSA-N 0.000 claims 3
- YJJNYKUVWNSKQE-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl acetate Chemical compound CC(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YJJNYKUVWNSKQE-UHFFFAOYSA-N 0.000 claims 3
- HBSWMTRBCJGKNK-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl benzoate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOC(=O)C=2C=CC=CC=2)=CS1 HBSWMTRBCJGKNK-UHFFFAOYSA-N 0.000 claims 3
- DHILZBKTQNBASR-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl furan-2-carboxylate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOC(=O)C=2OC=CC=2)=CS1 DHILZBKTQNBASR-UHFFFAOYSA-N 0.000 claims 3
- VYZWVMVWGHXNGP-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl methanesulfonate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOS(C)(=O)=O)=CS1 VYZWVMVWGHXNGP-UHFFFAOYSA-N 0.000 claims 3
- VKMTYZOUAYGZLK-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl propanoate Chemical compound CCC(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 VKMTYZOUAYGZLK-UHFFFAOYSA-N 0.000 claims 3
- SFYSOCDXRYVHSP-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-(oxolan-2-ylmethyl)acetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)NCC2OCCC2)=CS1 SFYSOCDXRYVHSP-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- AYKJIFPXBJZYOI-UHFFFAOYSA-N 2-[2-[(4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(CC(O)=O)=CS1 AYKJIFPXBJZYOI-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- VNCUBHRMXCJHJU-UHFFFAOYSA-N 2-methyl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound CC1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 VNCUBHRMXCJHJU-UHFFFAOYSA-N 0.000 claims 3
- YWCBGZLJKFQWCX-UHFFFAOYSA-N 2-methyl-n-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(OC(F)(F)F)=CC=2)C)=N1 YWCBGZLJKFQWCX-UHFFFAOYSA-N 0.000 claims 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- JQAGIZSPAQASSK-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 JQAGIZSPAQASSK-UHFFFAOYSA-N 0.000 claims 3
- BNXRPBHLSFLTSL-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-oxo-2-piperazin-1-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCNCC2)=CS1 BNXRPBHLSFLTSL-UHFFFAOYSA-N 0.000 claims 3
- SPPUGWFMZNHQCI-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-oxo-2-piperidin-1-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCCCC2)=CS1 SPPUGWFMZNHQCI-UHFFFAOYSA-N 0.000 claims 3
- SBMGFUZZILGLEQ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-oxo-2-pyrrolidin-1-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCCC2)=CS1 SBMGFUZZILGLEQ-UHFFFAOYSA-N 0.000 claims 3
- PNOHBAWJVWEEEW-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-oxo-2-thiomorpholin-4-ylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCSCC2)=CS1 PNOHBAWJVWEEEW-UHFFFAOYSA-N 0.000 claims 3
- LRSHRBXCWRJSCQ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-oxopentyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCCC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 LRSHRBXCWRJSCQ-UHFFFAOYSA-N 0.000 claims 3
- PCURMNYHJKIXIK-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-phenylmethoxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOCC=2C=CC=CC=2)=CS1 PCURMNYHJKIXIK-UHFFFAOYSA-N 0.000 claims 3
- RJBYZNYPFAZOTP-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-propan-2-yloxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC(C)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 RJBYZNYPFAZOTP-UHFFFAOYSA-N 0.000 claims 3
- FEBDOOGGNQMLEA-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-pyridin-2-ylsulfanylethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCSC=2N=CC=CC=2)=CS1 FEBDOOGGNQMLEA-UHFFFAOYSA-N 0.000 claims 3
- GOOHJWXSYSIJCN-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-pyridin-3-yloxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOC=2C=NC=CC=2)=CS1 GOOHJWXSYSIJCN-UHFFFAOYSA-N 0.000 claims 3
- FCZLQYWUZTVEES-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[(3-oxomorpholin-4-yl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CN2C(COCC2)=O)=CS1 FCZLQYWUZTVEES-UHFFFAOYSA-N 0.000 claims 3
- BWXKSRWYBGUSHW-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(2-methyl-3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound O=C1C(C)OCCN1CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 BWXKSRWYBGUSHW-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- YASLYRKHUXLPPN-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YASLYRKHUXLPPN-UHFFFAOYSA-N 0.000 claims 3
- WZFHKKLPBJCDRS-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(4-methylpiperazin-1-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WZFHKKLPBJCDRS-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- UZWQRKFUNIGEEO-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(trifluoromethylsulfonylamino)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNS(=O)(=O)C(F)(F)F)=CS1 UZWQRKFUNIGEEO-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- 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 claims 3
- XNIJTLZWWZHATQ-UHFFFAOYSA-N 3-chloro-n-[4-(2-chloroethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCl)=CS1 XNIJTLZWWZHATQ-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- 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 claims 3
- MQNNPMUEUFLKRU-UHFFFAOYSA-N 3-chloro-n-[4-[2-(2-fluoroethoxy)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOCCF)=CS1 MQNNPMUEUFLKRU-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- GVEMPLKGNIFWOE-UHFFFAOYSA-N 3-chloro-n-[4-[2-(ethylamino)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCNCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GVEMPLKGNIFWOE-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- BZFCCDBKOGHSPH-UHFFFAOYSA-N 3-fluoro-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2SC=C(CCN3C(COCC3)=O)N=2)=C1 BZFCCDBKOGHSPH-UHFFFAOYSA-N 0.000 claims 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- DZOVJGIRFXTALH-UHFFFAOYSA-N 4,5-dichloro-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound S1C(Cl)=C(Cl)C=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 DZOVJGIRFXTALH-UHFFFAOYSA-N 0.000 claims 3
- QKLDLIUPDVKUJI-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1SC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=C3OCOC3=CC=2)=NC=1CC(=O)N1CCOCC1 QKLDLIUPDVKUJI-UHFFFAOYSA-N 0.000 claims 3
- QJQRNQNWXNMGTG-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 QJQRNQNWXNMGTG-UHFFFAOYSA-N 0.000 claims 3
- SXFRVZFEFYQRTN-UHFFFAOYSA-N 4-(5-methylthiophen-2-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound S1C(C)=CC=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 SXFRVZFEFYQRTN-UHFFFAOYSA-N 0.000 claims 3
- NGHRCUNMYJHQKD-UHFFFAOYSA-N 4-(furan-2-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CO1 NGHRCUNMYJHQKD-UHFFFAOYSA-N 0.000 claims 3
- NOLMXNHBTMCQLS-UHFFFAOYSA-N 4-chloro-n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound OCCC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 NOLMXNHBTMCQLS-UHFFFAOYSA-N 0.000 claims 3
- ZXBXNYWGPIFHCW-UHFFFAOYSA-N 4-chloro-n-[4-[2-(diethylamino)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide;hydrochloride Chemical compound Cl.CCN(CC)CCC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 ZXBXNYWGPIFHCW-UHFFFAOYSA-N 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 3
- 125000001769 aryl amino group Chemical class 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical class 0.000 claims 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- KFCUPNHUPHDVJC-UHFFFAOYSA-N bromine azide Chemical group BrN=[N+]=[N-] KFCUPNHUPHDVJC-UHFFFAOYSA-N 0.000 claims 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 3
- 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 claims 3
- JVAFXOOYGZUHAM-UHFFFAOYSA-N ethyl 2-[2-(quinolin-8-ylsulfonylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)=N1 JVAFXOOYGZUHAM-UHFFFAOYSA-N 0.000 claims 3
- CAAGINURIJZJFA-UHFFFAOYSA-N ethyl 2-[2-[(1-methylimidazol-4-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2N=CN(C)C=2)=N1 CAAGINURIJZJFA-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- YVDPHJVUTMGFBK-UHFFFAOYSA-N ethyl 2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 YVDPHJVUTMGFBK-UHFFFAOYSA-N 0.000 claims 3
- CQCXDXXEKHBZCA-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 CQCXDXXEKHBZCA-UHFFFAOYSA-N 0.000 claims 3
- AZFIPTGNCDPGCH-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)Cl)=N1 AZFIPTGNCDPGCH-UHFFFAOYSA-N 0.000 claims 3
- KACQGQGBDKICBL-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)=N1 KACQGQGBDKICBL-UHFFFAOYSA-N 0.000 claims 3
- OEECZQVLXUNUQW-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dichlorothiophen-3-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=N1 OEECZQVLXUNUQW-UHFFFAOYSA-N 0.000 claims 3
- IQHJPEZHJFMMKA-UHFFFAOYSA-N ethyl 2-[2-[(2-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Br)=N1 IQHJPEZHJFMMKA-UHFFFAOYSA-N 0.000 claims 3
- JDBWRECUZVWGNO-UHFFFAOYSA-N ethyl 2-[2-[(2-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 JDBWRECUZVWGNO-UHFFFAOYSA-N 0.000 claims 3
- HAGXVJTVTTUNAP-UHFFFAOYSA-N ethyl 2-[2-[(2-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)C#N)=N1 HAGXVJTVTTUNAP-UHFFFAOYSA-N 0.000 claims 3
- PMRYJIFBBGSVKP-UHFFFAOYSA-N ethyl 2-[2-[(2-methoxy-4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(C)=CC=2)OC)=N1 PMRYJIFBBGSVKP-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- 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 claims 3
- PDEKOPUOMNHLQP-UHFFFAOYSA-N ethyl 2-[2-[(3-bromo-5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C2=C(C=C(Cl)S2)Br)=N1 PDEKOPUOMNHLQP-UHFFFAOYSA-N 0.000 claims 3
- ZTCSTONMUHDFKJ-UHFFFAOYSA-N ethyl 2-[2-[(3-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Br)C=CC=2)=N1 ZTCSTONMUHDFKJ-UHFFFAOYSA-N 0.000 claims 3
- GZLJHVLKSZQICO-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GZLJHVLKSZQICO-UHFFFAOYSA-N 0.000 claims 3
- WYLIDXHKCNSRSG-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WYLIDXHKCNSRSG-UHFFFAOYSA-N 0.000 claims 3
- ANVGCTSGCSBOTQ-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(C)=CC=2)=N1 ANVGCTSGCSBOTQ-UHFFFAOYSA-N 0.000 claims 3
- YTRIEVDHWCSHLN-UHFFFAOYSA-N ethyl 2-[2-[(3-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=N1 YTRIEVDHWCSHLN-UHFFFAOYSA-N 0.000 claims 3
- WDZSIANQAZTVEH-UHFFFAOYSA-N ethyl 2-[2-[(3-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)C#N)=N1 WDZSIANQAZTVEH-UHFFFAOYSA-N 0.000 claims 3
- BOFWWAXNVWTGKH-UHFFFAOYSA-N ethyl 2-[2-[(3-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(F)C=CC=2)=N1 BOFWWAXNVWTGKH-UHFFFAOYSA-N 0.000 claims 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 claims 3
- WZQBUAOAZRGEBW-UHFFFAOYSA-N ethyl 2-[2-[(3-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C)C=CC=2)=N1 WZQBUAOAZRGEBW-UHFFFAOYSA-N 0.000 claims 3
- JWPFFPNIEBVQBS-UHFFFAOYSA-N ethyl 2-[2-[(4,5-dichlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=N1 JWPFFPNIEBVQBS-UHFFFAOYSA-N 0.000 claims 3
- UHAQMGZZUVKJHH-UHFFFAOYSA-N ethyl 2-[2-[(4-acetamido-3-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(NC(C)=O)=CC=2)=N1 UHAQMGZZUVKJHH-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- XQETZYRGNIDJBQ-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)F)=N1 XQETZYRGNIDJBQ-UHFFFAOYSA-N 0.000 claims 3
- GJLYEXVGTDRIDB-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=N1 GJLYEXVGTDRIDB-UHFFFAOYSA-N 0.000 claims 3
- PGUXTMPTPRTMHK-UHFFFAOYSA-N ethyl 2-[2-[(4-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(Br)=CC=2)=N1 PGUXTMPTPRTMHK-UHFFFAOYSA-N 0.000 claims 3
- AAWVIKWDCOANTH-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)C)=N1 AAWVIKWDCOANTH-UHFFFAOYSA-N 0.000 claims 3
- MSBRGTIONVCFPM-UHFFFAOYSA-N ethyl 2-[2-[(4-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C#N)=N1 MSBRGTIONVCFPM-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- IUMBUSOAXLMIQO-UHFFFAOYSA-N ethyl 2-[2-[(4-iodophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(I)=CC=2)=N1 IUMBUSOAXLMIQO-UHFFFAOYSA-N 0.000 claims 3
- UZBKVHNVGKVIBK-UHFFFAOYSA-N ethyl 2-[2-[(4-methoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC)=CC=2)=N1 UZBKVHNVGKVIBK-UHFFFAOYSA-N 0.000 claims 3
- GGFUIBCPKURKMT-UHFFFAOYSA-N ethyl 2-[2-[(4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 GGFUIBCPKURKMT-UHFFFAOYSA-N 0.000 claims 3
- JIHXZUUTKHVLNU-UHFFFAOYSA-N ethyl 2-[2-[(4-phenoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 JIHXZUUTKHVLNU-UHFFFAOYSA-N 0.000 claims 3
- HTGLZCFZWSAEEN-UHFFFAOYSA-N ethyl 2-[2-[(4-propan-2-ylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C(C)C)=N1 HTGLZCFZWSAEEN-UHFFFAOYSA-N 0.000 claims 3
- VJZNBJUIDMRTPW-UHFFFAOYSA-N ethyl 2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OCC)=CS1 VJZNBJUIDMRTPW-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- HKEFYAKHKFYMMG-UHFFFAOYSA-N ethyl 2-[2-[(5-fluoro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(F)C=2)C)=N1 HKEFYAKHKFYMMG-UHFFFAOYSA-N 0.000 claims 3
- HMGOOODTJVJVDK-CMDGGOBGSA-N ethyl 2-[2-[[(e)-2-phenylethenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)\C=C\C=2C=CC=CC=2)=N1 HMGOOODTJVJVDK-CMDGGOBGSA-N 0.000 claims 3
- 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 claims 3
- 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 claims 3
- 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 claims 3
- JJHPJQFQWBOQJM-UHFFFAOYSA-N ethyl 2-[2-[[3-[[4-(2-ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]sulfamoyl]benzoyl]amino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NC(=O)C=2C=C(C=CC=2)S(=O)(=O)NC=2SC=C(CC(=O)OCC)N=2)=N1 JJHPJQFQWBOQJM-UHFFFAOYSA-N 0.000 claims 3
- LSUOHCBWXCYLMG-UHFFFAOYSA-N ethyl 2-[2-[[4-(benzenesulfonyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC=C(C=2)S(=O)(=O)C=2C=CC=CC=2)=N1 LSUOHCBWXCYLMG-UHFFFAOYSA-N 0.000 claims 3
- ZODUISOKTTXHTP-UHFFFAOYSA-N ethyl 2-[2-[[4-(trifluoromethyl)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=N1 ZODUISOKTTXHTP-UHFFFAOYSA-N 0.000 claims 3
- IGKYRCNENBYGMB-UHFFFAOYSA-N ethyl 2-[2-[[5-(2-methylsulfanylpyrimidin-4-yl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C=2N=C(SC)N=CC=2)=N1 IGKYRCNENBYGMB-UHFFFAOYSA-N 0.000 claims 3
- BNACUUGAPKFPRZ-UHFFFAOYSA-N ethyl 2-[2-[[5-(benzenesulfonyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)S(=O)(=O)C=2C=CC=CC=2)=N1 BNACUUGAPKFPRZ-UHFFFAOYSA-N 0.000 claims 3
- SRRCAMPLVRPDHC-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C(=O)C(=O)OCC)=CS1 SRRCAMPLVRPDHC-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- VAJCYQHLYBTSHG-UHFFFAOYSA-N ethyl n,n-diethylcarbamate Chemical compound CCOC(=O)N(CC)CC VAJCYQHLYBTSHG-UHFFFAOYSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 150000002366 halogen compounds Chemical class 0.000 claims 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 3
- 125000005368 heteroarylthio group Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- YLUZIQCKIDKLID-UHFFFAOYSA-N methyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound COC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YLUZIQCKIDKLID-UHFFFAOYSA-N 0.000 claims 3
- BTWRJCDJRYLOCZ-UHFFFAOYSA-N methyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C BTWRJCDJRYLOCZ-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- CDVKLSKOQNAVCZ-UHFFFAOYSA-N methyl 2-[2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 CDVKLSKOQNAVCZ-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- KCIZIKWZFCENMB-UHFFFAOYSA-N n,n-di(propan-2-yl)-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CC(C)N(C(C)C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 KCIZIKWZFCENMB-UHFFFAOYSA-N 0.000 claims 3
- KASYRVNOWHARGW-UHFFFAOYSA-N n,n-di(propan-2-yl)-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N(C(C)C)C(C)C)=CS1 KASYRVNOWHARGW-UHFFFAOYSA-N 0.000 claims 3
- FDKSCNNPNTWASM-UHFFFAOYSA-N n,n-diethyl-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CCN(CC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 FDKSCNNPNTWASM-UHFFFAOYSA-N 0.000 claims 3
- VYJPKJQHXPFNGR-UHFFFAOYSA-N n,n-diethyl-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N(CC)CC)=CS1 VYJPKJQHXPFNGR-UHFFFAOYSA-N 0.000 claims 3
- OABDREFMJCKLIU-UHFFFAOYSA-N n-(2-methoxyethyl)-2-[2-[(4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound COCCNC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 OABDREFMJCKLIU-UHFFFAOYSA-N 0.000 claims 3
- PFWDLCWNUMFJJK-UHFFFAOYSA-N n-(furan-2-ylmethyl)-2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]acetamide Chemical compound C=1SC(NS(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=NC=1CC(=O)NCC1=CC=CO1 PFWDLCWNUMFJJK-UHFFFAOYSA-N 0.000 claims 3
- HEOXDBQVGHVNLH-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]-2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]acetamide Chemical compound C1=CC=C2C(CCNC(CC=3N=C(NS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)SC=3)=O)=CNC2=C1 HEOXDBQVGHVNLH-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- 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 claims 3
- 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 claims 3
- 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 claims 3
- KDWZXHHMVXZGSZ-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-2,4-bis(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 KDWZXHHMVXZGSZ-UHFFFAOYSA-N 0.000 claims 3
- OSKLWZDEGFSCDY-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-(pyridin-3-ylmethylamino)benzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1NCC1=CC=CN=C1 OSKLWZDEGFSCDY-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- 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 claims 3
- 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 claims 3
- 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 claims 3
- 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 claims 3
- 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 claims 3
- 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 claims 3
- VIIMYBURVMJFOF-UHFFFAOYSA-N n-benzhydryl-2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=NC(CC(=O)NC(C=2C=CC=CC=2)C=2C=CC=CC=2)=CS1 VIIMYBURVMJFOF-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- ITSYGEVZNPQFOG-UHFFFAOYSA-N n-ethyl-n-methyl-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CCN(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 ITSYGEVZNPQFOG-UHFFFAOYSA-N 0.000 claims 3
- QRGPSAWENJEUME-UHFFFAOYSA-N n-ethyl-n-methyl-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N(C)CC)=CS1 QRGPSAWENJEUME-UHFFFAOYSA-N 0.000 claims 3
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- FGEITWLWOHALNM-UHFFFAOYSA-N propan-2-yl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CC(C)OC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 FGEITWLWOHALNM-UHFFFAOYSA-N 0.000 claims 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 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 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 3
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims 2
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims 2
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- VCPRDRUUVHTPGZ-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 VCPRDRUUVHTPGZ-UHFFFAOYSA-N 0.000 claims 2
- SVQVJVLGGPLRIW-UHFFFAOYSA-N 4-(4-methylpiperidin-1-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1CC(C)CCN1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 SVQVJVLGGPLRIW-UHFFFAOYSA-N 0.000 claims 2
- IDDLDQUYMRMWCT-UHFFFAOYSA-N 4-(4-methylsulfanylphenyl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(SC)=CC=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 IDDLDQUYMRMWCT-UHFFFAOYSA-N 0.000 claims 2
- TZNDCHUGTISBJP-UHFFFAOYSA-N 4-(5-chlorothiophen-2-yl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound S1C(Cl)=CC=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 TZNDCHUGTISBJP-UHFFFAOYSA-N 0.000 claims 2
- NHKHEYOGWVQQDI-UHFFFAOYSA-N 4-bromo-2-methyl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Br)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 NHKHEYOGWVQQDI-UHFFFAOYSA-N 0.000 claims 2
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
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- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- 206010024229 Leprosy Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- IJNMHHJKXLKFJT-UHFFFAOYSA-N ethyl 2-[2-(benzenesulfonamido)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC=CC=2)=N1 IJNMHHJKXLKFJT-UHFFFAOYSA-N 0.000 claims 2
- AYEZJMCEEUOZBO-UHFFFAOYSA-N ethyl 2-[2-[(2,3,4-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C(Cl)=CC=2)Cl)=N1 AYEZJMCEEUOZBO-UHFFFAOYSA-N 0.000 claims 2
- CBVGFYLRKFMWIY-UHFFFAOYSA-N ethyl 2-[2-[(2,3-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=N1 CBVGFYLRKFMWIY-UHFFFAOYSA-N 0.000 claims 2
- DFPIHKZQUYAUSJ-UHFFFAOYSA-N ethyl 2-[2-[(2,4,5-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 DFPIHKZQUYAUSJ-UHFFFAOYSA-N 0.000 claims 2
- XTSPBSIOOVDLFL-UHFFFAOYSA-N ethyl 2-[2-[(2,4,6-trifluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2F)F)=N1 XTSPBSIOOVDLFL-UHFFFAOYSA-N 0.000 claims 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 claims 2
- DOCGWETVZQBVQM-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichloro-5-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=C(C)C=2)Cl)=N1 DOCGWETVZQBVQM-UHFFFAOYSA-N 0.000 claims 2
- RXLDVKZBTUCMEB-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 RXLDVKZBTUCMEB-UHFFFAOYSA-N 0.000 claims 2
- FCKASCFOIWCCQJ-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dimethoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(OC)C=2)OC)=N1 FCKASCFOIWCCQJ-UHFFFAOYSA-N 0.000 claims 2
- FUOFZFZFISSASM-UHFFFAOYSA-N ethyl 2-[2-[(2,6-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 FUOFZFZFISSASM-UHFFFAOYSA-N 0.000 claims 2
- FIUOJUMQXLUVOT-UHFFFAOYSA-N ethyl 2-[2-[(2-chloro-4-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)Cl)=N1 FIUOJUMQXLUVOT-UHFFFAOYSA-N 0.000 claims 2
- ZCNWUMGMIAXUQD-UHFFFAOYSA-N ethyl 2-[2-[(2-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 ZCNWUMGMIAXUQD-UHFFFAOYSA-N 0.000 claims 2
- HLIXWSCWOHFWJI-UHFFFAOYSA-N ethyl 2-[2-[(3,4-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 HLIXWSCWOHFWJI-UHFFFAOYSA-N 0.000 claims 2
- XJVXNSMNVRSDPC-UHFFFAOYSA-N ethyl 2-[2-[(3,5-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=N1 XJVXNSMNVRSDPC-UHFFFAOYSA-N 0.000 claims 2
- GIDZENNFVLMYKK-UHFFFAOYSA-N ethyl 2-[2-[(3-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=N1 GIDZENNFVLMYKK-UHFFFAOYSA-N 0.000 claims 2
- KKXBMETYIBLJLL-UHFFFAOYSA-N ethyl 2-[2-[(4-butoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OCC)=CS1 KKXBMETYIBLJLL-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 2
- UWYFMDJTWUHYCH-UHFFFAOYSA-N ethyl 2-[2-[(4-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=N1 UWYFMDJTWUHYCH-UHFFFAOYSA-N 0.000 claims 2
- YRRUWWOAPIHJJB-UHFFFAOYSA-N ethyl 2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 YRRUWWOAPIHJJB-UHFFFAOYSA-N 0.000 claims 2
- BAWTURGOYHDKPA-UHFFFAOYSA-N ethyl 2-[2-[(5-bromo-2-methoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(Br)C=2)OC)=N1 BAWTURGOYHDKPA-UHFFFAOYSA-N 0.000 claims 2
- LVTJYYCKVHDIKX-UHFFFAOYSA-N ethyl 2-[2-[(5-chloro-1,3-dimethylpyrazol-4-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C2=C(N(C)N=C2C)Cl)=N1 LVTJYYCKVHDIKX-UHFFFAOYSA-N 0.000 claims 2
- SKMXVSXCYNCVLY-UHFFFAOYSA-N ethyl 2-[2-[[2,4-bis(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)C(F)(F)F)=N1 SKMXVSXCYNCVLY-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 2
- LQNOTNMKIUTWJD-UHFFFAOYSA-N ethyl 2-[2-[[4-[[4-(2-ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]sulfamoyl]benzoyl]amino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NC(=O)C=2C=CC(=CC=2)S(=O)(=O)NC=2SC=C(CC(=O)OCC)N=2)=N1 LQNOTNMKIUTWJD-UHFFFAOYSA-N 0.000 claims 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 claims 2
- MZTOQUINLWUTBG-UHFFFAOYSA-N ethyl 2-[2-[[5-(benzamidomethyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(CNC(=O)C=3C=CC=CC=3)=CC=2)=N1 MZTOQUINLWUTBG-UHFFFAOYSA-N 0.000 claims 2
- SSTFTUKNWXIXKH-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 SSTFTUKNWXIXKH-UHFFFAOYSA-N 0.000 claims 2
- IEGXMLXVLNHQQR-UHFFFAOYSA-N ethyl 3-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]propanoate Chemical compound CCOC(=O)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 IEGXMLXVLNHQQR-UHFFFAOYSA-N 0.000 claims 2
- RTBBWCJKGBZVGL-UHFFFAOYSA-N ethyl morpholine-4-carboxylate Chemical compound CCOC(=O)N1CCOCC1 RTBBWCJKGBZVGL-UHFFFAOYSA-N 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 2
- 201000008980 hyperinsulinism Diseases 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 230000004968 inflammatory condition Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 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 claims 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 claims 2
- POQSMNSPMDVTHU-UHFFFAOYSA-N methyl 2-[5-methyl-2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OC)=C(C)S1 POQSMNSPMDVTHU-UHFFFAOYSA-N 0.000 claims 2
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- LSPRNCRLZWVZMS-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-[4-(trifluoromethoxy)phenyl]benzenesulfonamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 LSPRNCRLZWVZMS-UHFFFAOYSA-N 0.000 claims 2
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- CSUYPAKJHXXDPC-UHFFFAOYSA-N phenyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)OC=2C=CC=CC=2)=CS1 CSUYPAKJHXXDPC-UHFFFAOYSA-N 0.000 claims 2
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- AGYLTFIWEUGKRP-UHFFFAOYSA-N 2,4-dichloro-6-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(=CC(Cl)=CC=2C)Cl)=N1 AGYLTFIWEUGKRP-UHFFFAOYSA-N 0.000 claims 1
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- RVGOYEWLPWEFCI-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 RVGOYEWLPWEFCI-UHFFFAOYSA-N 0.000 claims 1
- SQGWOBDUXQBFJO-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)=O)=CS1 SQGWOBDUXQBFJO-UHFFFAOYSA-N 0.000 claims 1
- CFFAUMQTHWNDOK-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl morpholine-4-carboxylate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOC(=O)N2CCOCC2)=CS1 CFFAUMQTHWNDOK-UHFFFAOYSA-N 0.000 claims 1
- NUSJTMYRJVRWGH-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NUSJTMYRJVRWGH-UHFFFAOYSA-N 0.000 claims 1
- VISGQGQJQWSXHJ-UHFFFAOYSA-N 2-[2-[(4-acetamidophenyl)sulfonylamino]-4-thiazolyl]acetic acid ethyl ester Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)=N1 VISGQGQJQWSXHJ-UHFFFAOYSA-N 0.000 claims 1
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- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
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- IKWXQEULPZNLEH-UHFFFAOYSA-N 3-chloro-n-[4-[2-(methanesulfonamido)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNS(C)(=O)=O)=CS1 IKWXQEULPZNLEH-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- KUXWEFJHUYNBNN-TXEJJXNPSA-N 3-chloro-n-[4-[2-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-2-oxoethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 KUXWEFJHUYNBNN-TXEJJXNPSA-N 0.000 claims 1
- VMFMBWQDDIDDNU-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound COC1=CC=C(F)C=C1C1=CC=C(S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)C=C1 VMFMBWQDDIDDNU-UHFFFAOYSA-N 0.000 claims 1
- ISYTZMQFESIBML-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2C=CC(=CC=2)S(=O)(=O)NC=2SC=C(CC(=O)N3CCOCC3)N=2)=C1 ISYTZMQFESIBML-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
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- 238000005917 acylation reaction Methods 0.000 claims 1
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- OWCDMRFUFMERMZ-UHFFFAOYSA-N benzenesulfonamide;hydrochloride Chemical compound Cl.NS(=O)(=O)C1=CC=CC=C1 OWCDMRFUFMERMZ-UHFFFAOYSA-N 0.000 claims 1
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- 230000021235 carbamoylation Effects 0.000 claims 1
- 229940016681 dipropylacetamide Drugs 0.000 claims 1
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- CWRLDLCBUSKDDE-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)C)=N1 CWRLDLCBUSKDDE-UHFFFAOYSA-N 0.000 claims 1
- DVAQZPOPYAJLPP-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2,5-dimethylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=C(C)C=2)C)=N1 DVAQZPOPYAJLPP-UHFFFAOYSA-N 0.000 claims 1
- OAGJLQCJTUZHMJ-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2,6-dimethylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)C)=N1 OAGJLQCJTUZHMJ-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 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 claims 1
- PVWVVNUNHXAKGT-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 PVWVVNUNHXAKGT-UHFFFAOYSA-N 0.000 claims 1
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- PDEPXTWYXQSUAK-UHFFFAOYSA-N methyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=C(C)C=C(Cl)C=C1Cl PDEPXTWYXQSUAK-UHFFFAOYSA-N 0.000 claims 1
- ZSUUCLLIOSUIFH-UHFFFAOYSA-N n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(C)=O ZSUUCLLIOSUIFH-UHFFFAOYSA-N 0.000 claims 1
- YYRBCTCJEIQSTN-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-pyridin-4-ylbenzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=NC=C1 YYRBCTCJEIQSTN-UHFFFAOYSA-N 0.000 claims 1
- YVKCRYGFPBTSGK-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-thiophen-3-ylbenzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1C=1C=CSC=1 YVKCRYGFPBTSGK-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 claims 1
- XXKCHCNCMMOAQP-UHFFFAOYSA-N n-benzhydryl-2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)NC(C=2C=CC=CC=2)C=2C=CC=CC=2)=CS1 XXKCHCNCMMOAQP-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 150000003585 thioureas Chemical class 0.000 claims 1
Classifications
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- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D277/84—Naphthothiazoles
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
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- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| SE0001899A SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | New compounds |
| PCT/SE2001/001155 WO2001090090A1 (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Publications (1)
| Publication Number | Publication Date |
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| DE1283831T1 true DE1283831T1 (de) | 2003-08-14 |
Family
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Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
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| DE1283831T Pending DE1283831T1 (de) | 2000-05-22 | 2001-05-22 | Inhibitoren der 11-beta-hydroxy-steroid-dehydrogenase des typs 1 |
| DE60143293T Expired - Lifetime DE60143293D1 (de) | 2000-05-22 | 2001-05-22 | Inhibitoren der 11-beta-hydroxy-steroid-dehydrogenase des typs 1 |
| DE60139931T Expired - Lifetime DE60139931D1 (de) | 2000-05-22 | 2001-05-22 | Inhibitoren der 11-beta-hydroxy-steroid-dehydrogenase des typs 1 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
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| DE60143293T Expired - Lifetime DE60143293D1 (de) | 2000-05-22 | 2001-05-22 | Inhibitoren der 11-beta-hydroxy-steroid-dehydrogenase des typs 1 |
| DE60139931T Expired - Lifetime DE60139931D1 (de) | 2000-05-22 | 2001-05-22 | Inhibitoren der 11-beta-hydroxy-steroid-dehydrogenase des typs 1 |
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| SE0001899D0 (sv) * | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
| WO2002002797A2 (en) * | 2000-07-05 | 2002-01-10 | 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 |
| AU2007205749B2 (en) * | 2001-11-22 | 2009-04-23 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| EA200400707A1 (ru) * | 2001-11-22 | 2004-10-28 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
| RS44204A (sr) | 2001-11-22 | 2007-06-04 | Biovitrum Ab., | Inhibitori 11-beta- hidroksistereoidne dehidrogenaze tipa 1 |
| EP1461327A1 (en) * | 2001-11-22 | 2004-09-29 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| US20030130279A1 (en) * | 2001-11-22 | 2003-07-10 | Guido Kurz | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| IL161154A0 (en) | 2001-11-22 | 2004-08-31 | 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 |
| WO2003065983A2 (en) | 2002-02-01 | 2003-08-14 | Merck & Co., Inc. | 11-beta-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 |
| US6872826B2 (en) * | 2002-03-29 | 2005-03-29 | Schering Corporation | Stereoselective alkylation of chiral 2-methyl-4-protected piperazines |
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