CA2409697C - Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 - Google Patents
Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 Download PDFInfo
- Publication number
- CA2409697C CA2409697C CA2409697A CA2409697A CA2409697C CA 2409697 C CA2409697 C CA 2409697C CA 2409697 A CA2409697 A CA 2409697A CA 2409697 A CA2409697 A CA 2409697A CA 2409697 C CA2409697 C CA 2409697C
- Authority
- CA
- Canada
- 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.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title description 9
- 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 title 1
- 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 307
- 238000000034 method Methods 0.000 claims abstract description 157
- 238000002360 preparation method Methods 0.000 claims abstract description 23
- 239000003814 drug Substances 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 4
- -1 di-substituted, amide Chemical class 0.000 claims description 581
- 229910052739 hydrogen Inorganic materials 0.000 claims description 141
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 133
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 105
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 81
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 65
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 61
- 150000002431 hydrogen Chemical group 0.000 claims description 50
- 230000008878 coupling Effects 0.000 claims description 48
- 238000010168 coupling process Methods 0.000 claims description 48
- 238000005859 coupling reaction Methods 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 21
- 229940124530 sulfonamide Drugs 0.000 claims description 20
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- 206010012601 diabetes mellitus Diseases 0.000 claims description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 13
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 13
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 13
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 10
- 208000001132 Osteoporosis Diseases 0.000 claims description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
- 235000020824 obesity Nutrition 0.000 claims description 10
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 9
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 208000010412 Glaucoma Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 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 description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- 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 description 6
- 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 description 6
- 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 description 6
- WSKHSWHWEKUKCK-UHFFFAOYSA-N 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 WSKHSWHWEKUKCK-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- JBKXGULGNQEDPS-UHFFFAOYSA-N 2-[2-[(2,4-difluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-ethylacetamide Chemical compound CCNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)F)=N1 JBKXGULGNQEDPS-UHFFFAOYSA-N 0.000 claims description 6
- HEMVPFSRVDOYIS-UHFFFAOYSA-N 2-[2-[(2,5-dichlorothiophen-3-yl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NS(=O)(=O)C2=C(SC(Cl)=C2)Cl)=N1 HEMVPFSRVDOYIS-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- RVGOYEWLPWEFCI-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 RVGOYEWLPWEFCI-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 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 description 6
- HCVDPOLLLJHUPC-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 HCVDPOLLLJHUPC-UHFFFAOYSA-N 0.000 claims description 6
- ZFZSPBPBECULLJ-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-phenylacetamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(=O)NC=2C=CC=CC=2)=CS1 ZFZSPBPBECULLJ-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- SQGWOBDUXQBFJO-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetic acid Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)=O)=CS1 SQGWOBDUXQBFJO-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- VYZWVMVWGHXNGP-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl methanesulfonate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCOS(C)(=O)=O)=CS1 VYZWVMVWGHXNGP-UHFFFAOYSA-N 0.000 claims description 6
- MNYDWIWWEGDUMZ-UHFFFAOYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]ethyl n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)OCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 MNYDWIWWEGDUMZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- HBNANTYKOKNNMC-UHFFFAOYSA-N 3-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]propyl methanesulfonate Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCOS(C)(=O)=O)=CS1 HBNANTYKOKNNMC-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- LRSHRBXCWRJSCQ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(2-oxopentyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCCC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 LRSHRBXCWRJSCQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- XNIJTLZWWZHATQ-UHFFFAOYSA-N 3-chloro-n-[4-(2-chloroethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCCl)=CS1 XNIJTLZWWZHATQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- GDULMDVSHSQBBG-UHFFFAOYSA-N 3-chloro-n-[4-[2-(diethylamino)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.CCN(CC)CCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GDULMDVSHSQBBG-UHFFFAOYSA-N 0.000 claims description 6
- KQXSRJQWBZKFPM-UHFFFAOYSA-N 3-chloro-n-[4-[2-[(3-chloro-2-methylphenyl)sulfonyl-methylamino]ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C=1C=CC(Cl)=C(C)C=1S(=O)(=O)N(C)CCC(N=1)=CSC=1NS(=O)(=O)C1=CC=CC(Cl)=C1C KQXSRJQWBZKFPM-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- MGTBRYKYGJELPX-UHFFFAOYSA-N 4-anilino-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=C1NC1=CC=CC=C1 MGTBRYKYGJELPX-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- NOLMXNHBTMCQLS-UHFFFAOYSA-N 4-chloro-n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound OCCC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 NOLMXNHBTMCQLS-UHFFFAOYSA-N 0.000 claims description 6
- QFDBISKHFLCXAV-UHFFFAOYSA-N 4-morpholin-4-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=C1N1CCOCC1 QFDBISKHFLCXAV-UHFFFAOYSA-N 0.000 claims description 6
- 206010012289 Dementia Diseases 0.000 claims description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 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 description 6
- JVAFXOOYGZUHAM-UHFFFAOYSA-N ethyl 2-[2-(quinolin-8-ylsulfonylamino)-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)=N1 JVAFXOOYGZUHAM-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- XTSPBSIOOVDLFL-UHFFFAOYSA-N ethyl 2-[2-[(2,4,6-trifluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2F)F)=N1 XTSPBSIOOVDLFL-UHFFFAOYSA-N 0.000 claims description 6
- AZFIPTGNCDPGCH-UHFFFAOYSA-N ethyl 2-[2-[(2,4-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)Cl)=N1 AZFIPTGNCDPGCH-UHFFFAOYSA-N 0.000 claims description 6
- KACQGQGBDKICBL-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)=N1 KACQGQGBDKICBL-UHFFFAOYSA-N 0.000 claims description 6
- FCKASCFOIWCCQJ-UHFFFAOYSA-N ethyl 2-[2-[(2,5-dimethoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(OC)C=2)OC)=N1 FCKASCFOIWCCQJ-UHFFFAOYSA-N 0.000 claims description 6
- FUOFZFZFISSASM-UHFFFAOYSA-N ethyl 2-[2-[(2,6-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 FUOFZFZFISSASM-UHFFFAOYSA-N 0.000 claims description 6
- IQHJPEZHJFMMKA-UHFFFAOYSA-N ethyl 2-[2-[(2-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Br)=N1 IQHJPEZHJFMMKA-UHFFFAOYSA-N 0.000 claims description 6
- JDBWRECUZVWGNO-UHFFFAOYSA-N ethyl 2-[2-[(2-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 JDBWRECUZVWGNO-UHFFFAOYSA-N 0.000 claims description 6
- HAGXVJTVTTUNAP-UHFFFAOYSA-N ethyl 2-[2-[(2-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)C#N)=N1 HAGXVJTVTTUNAP-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 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 description 6
- HLIXWSCWOHFWJI-UHFFFAOYSA-N ethyl 2-[2-[(3,4-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 HLIXWSCWOHFWJI-UHFFFAOYSA-N 0.000 claims description 6
- PDEKOPUOMNHLQP-UHFFFAOYSA-N ethyl 2-[2-[(3-bromo-5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C2=C(C=C(Cl)S2)Br)=N1 PDEKOPUOMNHLQP-UHFFFAOYSA-N 0.000 claims description 6
- ZTCSTONMUHDFKJ-UHFFFAOYSA-N ethyl 2-[2-[(3-bromophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Br)C=CC=2)=N1 ZTCSTONMUHDFKJ-UHFFFAOYSA-N 0.000 claims description 6
- ANVGCTSGCSBOTQ-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(C)=CC=2)=N1 ANVGCTSGCSBOTQ-UHFFFAOYSA-N 0.000 claims description 6
- YTRIEVDHWCSHLN-UHFFFAOYSA-N ethyl 2-[2-[(3-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=N1 YTRIEVDHWCSHLN-UHFFFAOYSA-N 0.000 claims description 6
- WDZSIANQAZTVEH-UHFFFAOYSA-N ethyl 2-[2-[(3-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C=CC=2)C#N)=N1 WDZSIANQAZTVEH-UHFFFAOYSA-N 0.000 claims description 6
- BOFWWAXNVWTGKH-UHFFFAOYSA-N ethyl 2-[2-[(3-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(F)C=CC=2)=N1 BOFWWAXNVWTGKH-UHFFFAOYSA-N 0.000 claims description 6
- WZQBUAOAZRGEBW-UHFFFAOYSA-N ethyl 2-[2-[(3-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(C)C=CC=2)=N1 WZQBUAOAZRGEBW-UHFFFAOYSA-N 0.000 claims description 6
- CWRLDLCBUSKDDE-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)C)=N1 CWRLDLCBUSKDDE-UHFFFAOYSA-N 0.000 claims description 6
- GJLYEXVGTDRIDB-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=N1 GJLYEXVGTDRIDB-UHFFFAOYSA-N 0.000 claims description 6
- KKXBMETYIBLJLL-UHFFFAOYSA-N ethyl 2-[2-[(4-butoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OCC)=CS1 KKXBMETYIBLJLL-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- OAGJLQCJTUZHMJ-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2,6-dimethylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)C)=N1 OAGJLQCJTUZHMJ-UHFFFAOYSA-N 0.000 claims description 6
- MSBRGTIONVCFPM-UHFFFAOYSA-N ethyl 2-[2-[(4-cyanophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C#N)=N1 MSBRGTIONVCFPM-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- IUMBUSOAXLMIQO-UHFFFAOYSA-N ethyl 2-[2-[(4-iodophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(I)=CC=2)=N1 IUMBUSOAXLMIQO-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- UWYFMDJTWUHYCH-UHFFFAOYSA-N ethyl 2-[2-[(4-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=N1 UWYFMDJTWUHYCH-UHFFFAOYSA-N 0.000 claims description 6
- JIHXZUUTKHVLNU-UHFFFAOYSA-N ethyl 2-[2-[(4-phenoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 JIHXZUUTKHVLNU-UHFFFAOYSA-N 0.000 claims description 6
- HTGLZCFZWSAEEN-UHFFFAOYSA-N ethyl 2-[2-[(4-propan-2-ylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C(C)C)=N1 HTGLZCFZWSAEEN-UHFFFAOYSA-N 0.000 claims description 6
- LVTJYYCKVHDIKX-UHFFFAOYSA-N ethyl 2-[2-[(5-chloro-1,3-dimethylpyrazol-4-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C2=C(N(C)N=C2C)Cl)=N1 LVTJYYCKVHDIKX-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- HKEFYAKHKFYMMG-UHFFFAOYSA-N ethyl 2-[2-[(5-fluoro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(F)C=2)C)=N1 HKEFYAKHKFYMMG-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- LSUOHCBWXCYLMG-UHFFFAOYSA-N ethyl 2-[2-[[4-(benzenesulfonyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC=C(C=2)S(=O)(=O)C=2C=CC=CC=2)=N1 LSUOHCBWXCYLMG-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- ZODUISOKTTXHTP-UHFFFAOYSA-N ethyl 2-[2-[[4-(trifluoromethyl)phenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)=N1 ZODUISOKTTXHTP-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- IGKYRCNENBYGMB-UHFFFAOYSA-N ethyl 2-[2-[[5-(2-methylsulfanylpyrimidin-4-yl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(=CC=2)C=2N=C(SC)N=CC=2)=N1 IGKYRCNENBYGMB-UHFFFAOYSA-N 0.000 claims description 6
- MZTOQUINLWUTBG-UHFFFAOYSA-N ethyl 2-[2-[[5-(benzamidomethyl)thiophen-2-yl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(CNC(=O)C=3C=CC=CC=3)=CC=2)=N1 MZTOQUINLWUTBG-UHFFFAOYSA-N 0.000 claims description 6
- SSTFTUKNWXIXKH-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 SSTFTUKNWXIXKH-UHFFFAOYSA-N 0.000 claims description 6
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 6
- PDEPXTWYXQSUAK-UHFFFAOYSA-N methyl 2-[2-[(2,4-dichloro-6-methylphenyl)sulfonylamino]-5-methyl-1,3-thiazol-4-yl]acetate Chemical compound S1C(C)=C(CC(=O)OC)N=C1NS(=O)(=O)C1=C(C)C=C(Cl)C=C1Cl PDEPXTWYXQSUAK-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 claims description 6
- 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 description 6
- SICLDSDJIXEPAP-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-pyrrolidin-1-ylbenzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1N1CCCC1 SICLDSDJIXEPAP-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 claims description 6
- 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 description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 5
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
- 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 description 5
- CGPRKKGTHPOISW-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 CGPRKKGTHPOISW-UHFFFAOYSA-N 0.000 claims description 5
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- 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 description 5
- FIUOJUMQXLUVOT-UHFFFAOYSA-N ethyl 2-[2-[(2-chloro-4-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(F)=CC=2)Cl)=N1 FIUOJUMQXLUVOT-UHFFFAOYSA-N 0.000 claims description 5
- PMRYJIFBBGSVKP-UHFFFAOYSA-N ethyl 2-[2-[(2-methoxy-4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(C)=CC=2)OC)=N1 PMRYJIFBBGSVKP-UHFFFAOYSA-N 0.000 claims description 5
- ZCNWUMGMIAXUQD-UHFFFAOYSA-N ethyl 2-[2-[(2-nitrophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 ZCNWUMGMIAXUQD-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- XJVXNSMNVRSDPC-UHFFFAOYSA-N ethyl 2-[2-[(3,5-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=N1 XJVXNSMNVRSDPC-UHFFFAOYSA-N 0.000 claims description 5
- GZLJHVLKSZQICO-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 GZLJHVLKSZQICO-UHFFFAOYSA-N 0.000 claims description 5
- WYLIDXHKCNSRSG-UHFFFAOYSA-N ethyl 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WYLIDXHKCNSRSG-UHFFFAOYSA-N 0.000 claims description 5
- JWPFFPNIEBVQBS-UHFFFAOYSA-N ethyl 2-[2-[(4,5-dichlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=N1 JWPFFPNIEBVQBS-UHFFFAOYSA-N 0.000 claims description 5
- UHAQMGZZUVKJHH-UHFFFAOYSA-N ethyl 2-[2-[(4-acetamido-3-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(NC(C)=O)=CC=2)=N1 UHAQMGZZUVKJHH-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- XQETZYRGNIDJBQ-UHFFFAOYSA-N ethyl 2-[2-[(4-bromo-2-fluorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Br)=CC=2)F)=N1 XQETZYRGNIDJBQ-UHFFFAOYSA-N 0.000 claims description 5
- AAWVIKWDCOANTH-UHFFFAOYSA-N ethyl 2-[2-[(4-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2)C)=N1 AAWVIKWDCOANTH-UHFFFAOYSA-N 0.000 claims description 5
- GGFUIBCPKURKMT-UHFFFAOYSA-N ethyl 2-[2-[(4-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 GGFUIBCPKURKMT-UHFFFAOYSA-N 0.000 claims description 5
- VJZNBJUIDMRTPW-UHFFFAOYSA-N ethyl 2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)OCC)=CS1 VJZNBJUIDMRTPW-UHFFFAOYSA-N 0.000 claims description 5
- BAWTURGOYHDKPA-UHFFFAOYSA-N ethyl 2-[2-[(5-bromo-2-methoxyphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C(=CC=C(Br)C=2)OC)=N1 BAWTURGOYHDKPA-UHFFFAOYSA-N 0.000 claims description 5
- HMGOOODTJVJVDK-CMDGGOBGSA-N ethyl 2-[2-[[(e)-2-phenylethenyl]sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)\C=C\C=2C=CC=CC=2)=N1 HMGOOODTJVJVDK-CMDGGOBGSA-N 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 claims description 5
- SRRCAMPLVRPDHC-UHFFFAOYSA-N ethyl 2-oxo-2-[2-[(4-propylphenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C(=O)C(=O)OCC)=CS1 SRRCAMPLVRPDHC-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 5
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 5
- 201000008980 hyperinsulinism Diseases 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 claims description 5
- AWAACVVVLZSRMV-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-[2-(naphthalen-1-ylsulfonylamino)-1,3-thiazol-4-yl]acetamide Chemical compound C1=C2OCOC2=CC(CNC(CC=2N=C(NS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)SC=2)=O)=C1 AWAACVVVLZSRMV-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 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 claims description 5
- 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 claims description 5
- SNKHZWZVCPVFIJ-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-(thiophen-2-ylmethylamino)benzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1NCC1=CC=CS1 SNKHZWZVCPVFIJ-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 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 description 5
- YLRZGZIHQQPNCD-UHFFFAOYSA-N n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]-4-thiophen-2-ylbenzenesulfonamide Chemical compound C1COCCN1C(=O)CC(N=1)=CSC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CS1 YLRZGZIHQQPNCD-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 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 description 5
- YRZIFGRNSHSHKU-UHFFFAOYSA-N n-[4-[2-(1,1-dioxo-1,4-thiazinan-4-yl)-2-oxoethyl]-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(CC(=O)N2CCS(=O)(=O)CC2)=CS1 YRZIFGRNSHSHKU-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
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- 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 description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
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- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
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- 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 description 5
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- 201000008827 tuberculosis Diseases 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 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 description 4
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- OCKUKOAKTSTSHL-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 OCKUKOAKTSTSHL-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
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- WVSCPCGKOUHZLV-UHFFFAOYSA-N 2,4-dichloro-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=2)Cl)=N1 WVSCPCGKOUHZLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
- 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 description 4
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- CIHVZGFDMUAGRZ-HNNXBMFYSA-N 2-[2-[(3-chloro-2-methylphenyl)sulfonylamino]-1,3-thiazol-4-yl]-n-methyl-n-[(1s)-1-phenylethyl]acetamide Chemical compound CN([C@@H](C)C=1C=CC=CC=1)C(=O)CC(N=1)=CSC=1NS(=O)(=O)C1=CC=CC(Cl)=C1C CIHVZGFDMUAGRZ-HNNXBMFYSA-N 0.000 claims description 4
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- 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 description 4
- 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 description 4
- 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 description 4
- UZWQRKFUNIGEEO-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(trifluoromethylsulfonylamino)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCNS(=O)(=O)C(F)(F)F)=CS1 UZWQRKFUNIGEEO-UHFFFAOYSA-N 0.000 claims description 4
- PMDHDRBKLSNVTO-UHFFFAOYSA-N 3-chloro-n-[4-(2-ethoxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCOCCC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 PMDHDRBKLSNVTO-UHFFFAOYSA-N 0.000 claims description 4
- PSIMSLBVQXNOEQ-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCO)=CS1 PSIMSLBVQXNOEQ-UHFFFAOYSA-N 0.000 claims description 4
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- MUUXKDKJIARHTQ-UHFFFAOYSA-N 4-chloro-2,6-dimethyl-n-[4-(2-morpholin-4-yl-2-oxoethyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(C)=C1S(=O)(=O)NC1=NC(CC(=O)N2CCOCC2)=CS1 MUUXKDKJIARHTQ-UHFFFAOYSA-N 0.000 claims description 4
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- IITATKCUYSUFMF-UHFFFAOYSA-N ethyl 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 IITATKCUYSUFMF-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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- 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 claims description 3
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- 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 description 3
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- 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 description 3
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- FMLPQHJYUZTHQS-MRVPVSSYSA-N tert-butyl (3r)-3-methylpiperazine-1-carboxylate Chemical compound C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1 FMLPQHJYUZTHQS-MRVPVSSYSA-N 0.000 description 1
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- WTQJMIDRBKCOTM-UHFFFAOYSA-N tert-butyl n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=NC(CCO)=CS1 WTQJMIDRBKCOTM-UHFFFAOYSA-N 0.000 description 1
- YVGRETLMYKOXMY-UHFFFAOYSA-N tert-butyl n-[4-[2-(3-oxo-1,4-oxazepan-4-yl)ethyl]-1,3-thiazol-2-yl]carbamate Chemical compound S1C(NC(=O)OC(C)(C)C)=NC(CCN2C(COCCC2)=O)=C1 YVGRETLMYKOXMY-UHFFFAOYSA-N 0.000 description 1
- ASYQEXWZAPBBGC-UHFFFAOYSA-N tert-butyl n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]carbamate Chemical compound S1C(NC(=O)OC(C)(C)C)=NC(CCN2C(COCC2)=O)=C1 ASYQEXWZAPBBGC-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
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- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
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- 230000000699 topical effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- 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
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- 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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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0001899-4 | 2000-05-22 | ||
| SE0001899A SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | New compounds |
| PCT/SE2001/001155 WO2001090090A1 (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2409697A1 CA2409697A1 (en) | 2001-11-29 |
| CA2409697C true CA2409697C (en) | 2010-07-13 |
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Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002408783A Abandoned CA2408783A1 (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| CA002408142A Expired - Fee Related CA2408142C (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| CA2409697A Expired - Fee Related CA2409697C (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| CA002408144A Expired - Fee Related CA2408144C (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002408783A Abandoned CA2408783A1 (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| CA002408142A Expired - Fee Related CA2408142C (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002408144A Expired - Fee Related CA2408144C (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Country Status (23)
| Country | Link |
|---|---|
| US (7) | US7132436B2 (OSRAM) |
| EP (4) | EP1283834B1 (OSRAM) |
| JP (4) | JP2003534339A (OSRAM) |
| KR (4) | KR20030016271A (OSRAM) |
| CN (4) | CN1430614A (OSRAM) |
| AR (1) | AR033534A1 (OSRAM) |
| AT (2) | ATE485283T1 (OSRAM) |
| AU (6) | AU6283101A (OSRAM) |
| BR (1) | BR0111099A (OSRAM) |
| CA (4) | CA2408783A1 (OSRAM) |
| DE (3) | DE1283831T1 (OSRAM) |
| EA (1) | EA005274B1 (OSRAM) |
| ES (1) | ES2333846T3 (OSRAM) |
| HU (1) | HUP0302435A3 (OSRAM) |
| IL (4) | IL152669A0 (OSRAM) |
| MX (1) | MXPA02011632A (OSRAM) |
| NO (4) | NO20025588L (OSRAM) |
| NZ (4) | NZ522591A (OSRAM) |
| PE (1) | PE20020100A1 (OSRAM) |
| PL (1) | PL360137A1 (OSRAM) |
| SE (1) | SE0001899D0 (OSRAM) |
| WO (5) | WO2001090090A1 (OSRAM) |
| ZA (4) | ZA200209359B (OSRAM) |
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- 2001-05-22 AU AU6093201A patent/AU6093201A/xx not_active Withdrawn
- 2001-05-22 CN CNB018099661A patent/CN1188403C/zh not_active Expired - Fee Related
- 2001-05-22 NZ NZ522538A patent/NZ522538A/en unknown
- 2001-05-22 CN CN01811609A patent/CN1437588A/zh active Pending
- 2001-05-22 IL IL15275301A patent/IL152753A0/xx unknown
- 2001-05-22 JP JP2001586278A patent/JP2003534336A/ja not_active Abandoned
- 2001-05-22 NZ NZ522507A patent/NZ522507A/en unknown
- 2001-05-22 IL IL15267001A patent/IL152670A0/xx unknown
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2002
- 2002-11-18 ZA ZA200209359A patent/ZA200209359B/en unknown
- 2002-11-18 ZA ZA200209362A patent/ZA200209362B/en unknown
- 2002-11-18 ZA ZA200209364A patent/ZA200209364B/en unknown
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- 2002-11-21 NO NO20025588A patent/NO20025588L/no not_active Application Discontinuation
- 2002-11-21 NO NO20025585A patent/NO323831B1/no not_active IP Right Cessation
- 2002-11-21 NO NO20025587A patent/NO323779B1/no not_active IP Right Cessation
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2005
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2006
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2009
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