NZ522591A - Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 - Google Patents
Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1Info
- Publication number
- NZ522591A NZ522591A NZ522591A NZ52259101A NZ522591A NZ 522591 A NZ522591 A NZ 522591A NZ 522591 A NZ522591 A NZ 522591A NZ 52259101 A NZ52259101 A NZ 52259101A NZ 522591 A NZ522591 A NZ 522591A
- Authority
- NZ
- New Zealand
- Prior art keywords
- thiazol
- chloro
- phenyl
- benzenesulfonamide
- dichloro
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 9
- 102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 title description 2
- 108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 160
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
- 208000008589 Obesity Diseases 0.000 claims abstract description 13
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 13
- 235000020824 obesity Nutrition 0.000 claims abstract description 13
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 201000010099 disease Diseases 0.000 claims abstract description 6
- 238000010189 synthetic method Methods 0.000 claims description 98
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 86
- -1 chloro, methylsulfonyl Chemical group 0.000 claims description 73
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 61
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 43
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 40
- 229940124530 sulfonamide Drugs 0.000 claims description 38
- 239000004305 biphenyl Substances 0.000 claims description 34
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- LEFGAGRZHLNPLS-UHFFFAOYSA-N 4-propylbenzenesulfonyl chloride Chemical compound CCCC1=CC=C(S(Cl)(=O)=O)C=C1 LEFGAGRZHLNPLS-UHFFFAOYSA-N 0.000 claims description 16
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 12
- ALBQXDHCMLLQMB-UHFFFAOYSA-N 4-phenylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1=CC=CC=C1 ALBQXDHCMLLQMB-UHFFFAOYSA-N 0.000 claims description 11
- 208000001132 Osteoporosis Diseases 0.000 claims description 11
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 8
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 claims description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 150000003456 sulfonamides Chemical class 0.000 claims description 8
- 208000010412 Glaucoma Diseases 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 201000001421 hyperglycemia Diseases 0.000 claims description 4
- 230000002519 immonomodulatory effect Effects 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- JWGBLRGWKGFLNS-UHFFFAOYSA-N n-(4-phenyl-1,3-thiazol-2-yl)-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC=CC=2)=CS1 JWGBLRGWKGFLNS-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 201000008827 tuberculosis Diseases 0.000 claims description 4
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 3
- 201000008980 hyperinsulinism Diseases 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- YGNYHKCTKPHZIG-UHFFFAOYSA-N n-[4-(2-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C=2N=C(NS(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)SC=2)=C1 YGNYHKCTKPHZIG-UHFFFAOYSA-N 0.000 claims description 3
- XMHYLNOKGUOPNR-UHFFFAOYSA-N n-[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2N=C(NS(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)SC=2)=C1 XMHYLNOKGUOPNR-UHFFFAOYSA-N 0.000 claims description 3
- NRIPBFUCPSYOOW-UHFFFAOYSA-N n-[4-[2-[(2,6-dichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 NRIPBFUCPSYOOW-UHFFFAOYSA-N 0.000 claims description 3
- XZCBMBTUYMYVPQ-UHFFFAOYSA-N 2,5-dichloro-n-[4-(3-chlorothiophen-2-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CSC(C=2N=C(NS(=O)(=O)C=3C(=CC=C(Cl)C=3)Cl)SC=2)=C1Cl XZCBMBTUYMYVPQ-UHFFFAOYSA-N 0.000 claims description 2
- 241000236488 Lepra Species 0.000 claims description 2
- 206010024229 Leprosy Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 150000003585 thioureas Chemical class 0.000 claims description 2
- YJNNVTABROTHKU-UHFFFAOYSA-N 2,4,6-trichloro-n-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C=CC=CC=2)=CS1 YJNNVTABROTHKU-UHFFFAOYSA-N 0.000 claims 3
- XWMIRFXHIDTQJJ-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)[N+]([O-])=O)Cl)=CS1 XWMIRFXHIDTQJJ-UHFFFAOYSA-N 0.000 claims 3
- OUIVYFVLHUTHFJ-UHFFFAOYSA-N 4-propyl-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=NC=CC=2)=CS1 OUIVYFVLHUTHFJ-UHFFFAOYSA-N 0.000 claims 3
- GWAQYWSNCVEJMW-UHFFFAOYSA-N 7-nitro-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC([N+](=O)[O-])=CC=C21 GWAQYWSNCVEJMW-UHFFFAOYSA-N 0.000 claims 3
- NPWLGEAARUTBIP-UHFFFAOYSA-N n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)-4-phenylbenzenesulfonamide Chemical compound N=1C(C=2C=CSC=2CC2)=C2SC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 NPWLGEAARUTBIP-UHFFFAOYSA-N 0.000 claims 3
- OYGSUBKAKZFLIY-UHFFFAOYSA-N n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=CC(OC)=CC=C21 OYGSUBKAKZFLIY-UHFFFAOYSA-N 0.000 claims 3
- INOGCCHVCWPGMI-UHFFFAOYSA-N n-(8-nitro-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-4-phenylbenzenesulfonamide Chemical compound N=1C=2C3=CC([N+](=O)[O-])=CC=C3CCC=2SC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 INOGCCHVCWPGMI-UHFFFAOYSA-N 0.000 claims 3
- TXIFSWBQGDCPIK-UHFFFAOYSA-N n-(8-nitro-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=CC=C([N+]([O-])=O)C=C21 TXIFSWBQGDCPIK-UHFFFAOYSA-N 0.000 claims 3
- SDNVLYKBFAOEMD-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 SDNVLYKBFAOEMD-UHFFFAOYSA-N 0.000 claims 3
- ATERRQIYRKISJZ-UHFFFAOYSA-N n-[4-(5-chlorothiophen-2-yl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound S1C(Cl)=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 ATERRQIYRKISJZ-UHFFFAOYSA-N 0.000 claims 3
- DFJRULZVAINKHJ-UHFFFAOYSA-N 2,3,4-trichloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1Cl DFJRULZVAINKHJ-UHFFFAOYSA-N 0.000 claims 2
- HJQRULUFRSMPIA-UHFFFAOYSA-N 2,3,4-trichloro-n-[4-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1OC(C=C1Cl)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C(Cl)=CC=2)Cl)=N1 HJQRULUFRSMPIA-UHFFFAOYSA-N 0.000 claims 2
- GVXOMWVQNODSOD-UHFFFAOYSA-N 2,4,6-trichloro-n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C2C=CS1 GVXOMWVQNODSOD-UHFFFAOYSA-N 0.000 claims 2
- PZWRBNYWPNGEOO-UHFFFAOYSA-N 2,4,6-trichloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl PZWRBNYWPNGEOO-UHFFFAOYSA-N 0.000 claims 2
- YWBBSEJKRWJKJL-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=CC=3Cl)Cl)SC=2)=C1 YWBBSEJKRWJKJL-UHFFFAOYSA-N 0.000 claims 2
- ZJIZQFTYZLTSMM-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C=CC=CC=2)=CS1 ZJIZQFTYZLTSMM-UHFFFAOYSA-N 0.000 claims 2
- AETBUEDTDDAPHZ-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C=NC=CC=2)=CS1 AETBUEDTDDAPHZ-UHFFFAOYSA-N 0.000 claims 2
- OEFLRNMNICOWET-UHFFFAOYSA-N 2,4-dichloro-n-(6-chloro-8-methylsulfonyl-4,5-dihydrothieno[3,4-e][1,3]benzothiazol-2-yl)-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C(Cl)SC(S(C)(=O)=O)=C21 OEFLRNMNICOWET-UHFFFAOYSA-N 0.000 claims 2
- JJWMKRNBYQJEHX-UHFFFAOYSA-N 2,4-dichloro-n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-6-methylbenzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C1=C(C)C=C(Cl)C=C1Cl JJWMKRNBYQJEHX-UHFFFAOYSA-N 0.000 claims 2
- NHHKXWPXAPBQTL-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C=CC=CC=2)=CS1 NHHKXWPXAPBQTL-UHFFFAOYSA-N 0.000 claims 2
- PCFSIJDBQZSHBH-UHFFFAOYSA-N 3-chloro-n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C2C=CS1 PCFSIJDBQZSHBH-UHFFFAOYSA-N 0.000 claims 2
- MGRVIPJHIXBGFN-UHFFFAOYSA-N 4-bromo-5-chloro-n-[4-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1C1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=N1 MGRVIPJHIXBGFN-UHFFFAOYSA-N 0.000 claims 2
- ZSDKYIALVTXWOK-UHFFFAOYSA-N 4-bromo-n-[4-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-thiazol-2-yl]-2,5-difluorobenzenesulfonamide Chemical compound C1=C(Br)C(F)=CC(S(=O)(=O)NC=2SC=C(N=2)C=2C(=CC(OC=3C=CC(Cl)=CC=3)=CC=2)Cl)=C1F ZSDKYIALVTXWOK-UHFFFAOYSA-N 0.000 claims 2
- WGVIRWKBCWZWRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1S(=O)(=O)NC(SC=1)=NC=1C1=CC=CC=C1 WGVIRWKBCWZWRP-UHFFFAOYSA-N 0.000 claims 2
- JVFCCRJSBNUDDU-UHFFFAOYSA-N 4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 JVFCCRJSBNUDDU-UHFFFAOYSA-N 0.000 claims 2
- ZYDKFFBEDBXPRV-UHFFFAOYSA-N ethyl 4-phenyl-2-[(4-phenylphenyl)sulfonylamino]-1,3-thiazole-5-carboxylate Chemical compound N=1C(C=2C=CC=CC=2)=C(C(=O)OCC)SC=1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZYDKFFBEDBXPRV-UHFFFAOYSA-N 0.000 claims 2
- BLTIIVURSXLRMW-UHFFFAOYSA-N n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound N=1C(C=2C=CSC=2CC2)=C2SC=1NS(=O)(=O)C1=CC=CC=C1 BLTIIVURSXLRMW-UHFFFAOYSA-N 0.000 claims 2
- ADWDFMILWAITHK-UHFFFAOYSA-N n-[2-[(3-chloro-2-methylphenyl)sulfonylamino]benzo[e][1,3]benzothiazol-6-yl]acetamide Chemical compound S1C2=CC=C3C(NC(=O)C)=CC=CC3=C2N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C ADWDFMILWAITHK-UHFFFAOYSA-N 0.000 claims 2
- VATOYJIUMWMLLX-UHFFFAOYSA-N n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound ClC1=CC=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 VATOYJIUMWMLLX-UHFFFAOYSA-N 0.000 claims 2
- ARSMOHDWKMRMGC-UHFFFAOYSA-N n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 ARSMOHDWKMRMGC-UHFFFAOYSA-N 0.000 claims 2
- WRZMEKKUQVDTEW-UHFFFAOYSA-N n-[4-[2-[(2,4,6-trichlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 WRZMEKKUQVDTEW-UHFFFAOYSA-N 0.000 claims 2
- DWBWMAAYLWUXQK-UHFFFAOYSA-N 2,3-difluorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(F)=C1F DWBWMAAYLWUXQK-UHFFFAOYSA-N 0.000 claims 1
- DYXBPGZNZNQXCN-UHFFFAOYSA-N 2,4,6-trichloro-n-(7,8-dimethoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)benzenesulfonamide Chemical compound N=1C=2C=3C=C(OC)C(OC)=CC=3CCC=2SC=1NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl DYXBPGZNZNQXCN-UHFFFAOYSA-N 0.000 claims 1
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- JNCDGKHJBKFXGQ-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2Cl)Cl)=N1 JNCDGKHJBKFXGQ-UHFFFAOYSA-N 0.000 claims 1
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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| SE0001899A SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | New compounds |
| PCT/SE2001/001158 WO2001090092A1 (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
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| NZ522591A true NZ522591A (en) | 2004-09-24 |
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| NZ522506A NZ522506A (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1, pharmaceutical use and preparation process thereof |
| NZ522538A NZ522538A (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 their use and preparation |
| NZ522591A NZ522591A (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| NZ522507A NZ522507A (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
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| NZ522506A NZ522506A (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1, pharmaceutical use and preparation process thereof |
| NZ522538A NZ522538A (en) | 2000-05-22 | 2001-05-22 | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 their use and preparation |
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| GB0107383D0 (en) * | 2001-03-23 | 2001-05-16 | Univ Edinburgh | Lipid profile modulation |
| EA200400708A1 (ru) | 2001-11-22 | 2004-10-28 | Биовитрум Аб | Ингибиторы 11-бета-гидроксистероиддегидрогеназы типа 1 |
| AU2007205749B2 (en) * | 2001-11-22 | 2009-04-23 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
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| EP1461327A1 (en) * | 2001-11-22 | 2004-09-29 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
| ES2346961T3 (es) | 2001-11-22 | 2010-10-22 | Biovitrum Ab | Inhibidores de 11-beta-hidroxiesteroide deshidrogenasa de tipo 1. |
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| JO2397B1 (en) | 2002-12-20 | 2007-06-17 | ميرك شارب اند دوم كوربوريشن | Terazol derivatives as beta-hydroxy steroid dihydrogenase-1 inhibitors |
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