NO323831B1 - Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 - Google Patents
Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 Download PDFInfo
- Publication number
- NO323831B1 NO323831B1 NO20025585A NO20025585A NO323831B1 NO 323831 B1 NO323831 B1 NO 323831B1 NO 20025585 A NO20025585 A NO 20025585A NO 20025585 A NO20025585 A NO 20025585A NO 323831 B1 NO323831 B1 NO 323831B1
- Authority
- NO
- Norway
- Prior art keywords
- thiazol
- chloro
- phenyl
- dichloro
- benzenesulfonamide
- Prior art date
Links
- 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 description 148
- 238000000034 method Methods 0.000 claims description 135
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 59
- -1 1-benzothien-3-yl Chemical group 0.000 claims description 50
- 229940124530 sulfonamide Drugs 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 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 25
- 239000000460 chlorine Chemical group 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 23
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 22
- 239000004305 biphenyl Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 13
- JVFCCRJSBNUDDU-UHFFFAOYSA-N 4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 JVFCCRJSBNUDDU-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 9
- 208000008589 Obesity Diseases 0.000 claims description 8
- 208000001132 Osteoporosis Diseases 0.000 claims description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 208000010412 Glaucoma Diseases 0.000 claims description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 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 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 230000002519 immonomodulatory effect Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CLJQXQIYLDQWKS-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC(OC)=CC=2)=CS1 CLJQXQIYLDQWKS-UHFFFAOYSA-N 0.000 claims description 5
- DTFUYISNOGWKOH-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 DTFUYISNOGWKOH-UHFFFAOYSA-N 0.000 claims description 4
- QVLPVUZEELMXSD-UHFFFAOYSA-N 4-bromo-n-[4-(2-chloro-6-fluorophenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=CC(Br)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2F)Cl)=CS1 QVLPVUZEELMXSD-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- HATIXYADQNSJGY-UHFFFAOYSA-N COClNC(C)=O Chemical compound COClNC(C)=O HATIXYADQNSJGY-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- 201000010099 disease Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- ASTPEDWQARSKGA-UHFFFAOYSA-N n-(4,5-dihydrothieno[3,2-e][1,3]benzothiazol-2-yl)-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC(S1)=NC2=C1CCC1=C2C=CS1 ASTPEDWQARSKGA-UHFFFAOYSA-N 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 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 description 3
- UQQMUUNYGNDIPZ-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C(=CC(Cl)=CC=3Cl)Cl)SC=2)=C1 UQQMUUNYGNDIPZ-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 3
- 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 description 3
- HUPOREXJXWSXEX-UHFFFAOYSA-N 4-bromo-5-chloro-n-[4-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound BrC1=C(Cl)SC(S(=O)(=O)NC=2SC=C(N=2)C=2C(=CC(OC=3C=CC(Cl)=CC=3)=CC=2)Cl)=C1 HUPOREXJXWSXEX-UHFFFAOYSA-N 0.000 claims description 3
- YAPWIIYQMOFZIP-UHFFFAOYSA-N 4-bromo-n-[4-[2,6-dichloro-4-(trifluoromethyl)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(=CC=2Cl)C(F)(F)F)Cl)=C1F YAPWIIYQMOFZIP-UHFFFAOYSA-N 0.000 claims description 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 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 3
- 206010024229 Leprosy Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- BCAOCGDSOGDAQA-UHFFFAOYSA-N ethyl 2-[2-[(4-chlorophenyl)sulfonylamino]-1,3-thiazol-4-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 BCAOCGDSOGDAQA-UHFFFAOYSA-N 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
- XFSPRFGBEXCDSK-UHFFFAOYSA-N n-[4-(2-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)[N+]([O-])=O)Cl)=CS1 XFSPRFGBEXCDSK-UHFFFAOYSA-N 0.000 claims description 3
- CJGIFZPKHNHXMK-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-4-phenylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)SC=2)=C1 CJGIFZPKHNHXMK-UHFFFAOYSA-N 0.000 claims description 3
- KSRJVDSZGGXISO-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 KSRJVDSZGGXISO-UHFFFAOYSA-N 0.000 claims description 3
- GRFPSOYNHSFEJZ-UHFFFAOYSA-N n-[4-[2-[(4-bromo-5-chlorothiophen-2-yl)sulfonylamino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Br)C=2)=N1 GRFPSOYNHSFEJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 3
- 201000008827 tuberculosis Diseases 0.000 claims description 3
- 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 description 2
- WJZGIBDJVQHZBI-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 WJZGIBDJVQHZBI-UHFFFAOYSA-N 0.000 claims description 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 description 2
- KSSWUCOOEXHNBU-UHFFFAOYSA-N 2,4,6-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(=CC(Cl)=CC=2Cl)Cl)=N1 KSSWUCOOEXHNBU-UHFFFAOYSA-N 0.000 claims description 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 description 2
- VUQXWOCNCDSVII-UHFFFAOYSA-N 2,4-dichloro-n-[4-(2-chloro-6-fluorophenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2F)Cl)=CS1 VUQXWOCNCDSVII-UHFFFAOYSA-N 0.000 claims description 2
- WGJFORGGQDOUAV-UHFFFAOYSA-N 2,4-dichloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-6-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 WGJFORGGQDOUAV-UHFFFAOYSA-N 0.000 claims description 2
- CMOQLUAPPPUJTM-UHFFFAOYSA-N 3-chloro-2-methyl-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C=NC=CC=2)=CS1 CMOQLUAPPPUJTM-UHFFFAOYSA-N 0.000 claims description 2
- QHMZLUSHIXCCKP-UHFFFAOYSA-N 3-chloro-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)Cl)=CS1 QHMZLUSHIXCCKP-UHFFFAOYSA-N 0.000 claims description 2
- OFGHBOOJNFEGPN-UHFFFAOYSA-N 3-chloro-n-[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2N=C(NS(=O)(=O)C=3C(=C(Cl)C=CC=3)C)SC=2)=C1 OFGHBOOJNFEGPN-UHFFFAOYSA-N 0.000 claims description 2
- LXXRUQRDBHMNOA-UHFFFAOYSA-N 4,5-dichloro-n-[4-(2-chloro-6-fluorophenyl)-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound FC1=CC=CC(Cl)=C1C1=CSC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=N1 LXXRUQRDBHMNOA-UHFFFAOYSA-N 0.000 claims description 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 description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 201000001421 hyperglycemia Diseases 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- OMAMNIZLTOWNOM-UHFFFAOYSA-N n-(7-methoxy-4,5-dihydrobenzo[e][1,3]benzothiazol-2-yl)-4-phenylbenzenesulfonamide Chemical compound S1C=2CCC3=CC(OC)=CC=C3C=2N=C1NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 OMAMNIZLTOWNOM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- QSNHYHIQRJKESU-UHFFFAOYSA-N n-[4-(2-chloro-6-fluorophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2F)Cl)=CS1 QSNHYHIQRJKESU-UHFFFAOYSA-N 0.000 claims description 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 description 2
- GJXCRMNFCPLYHK-UHFFFAOYSA-N n-[4-[2-[(2,4,5-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)=C(Cl)C=2)Cl)=N1 GJXCRMNFCPLYHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 150000003585 thioureas Chemical class 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D491/02—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 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—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
- 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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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20025585D0 NO20025585D0 (no) | 2002-11-21 |
| NO20025585L NO20025585L (no) | 2002-12-23 |
| NO323831B1 true NO323831B1 (no) | 2007-07-09 |
Family
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Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20025585A NO323831B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
| NO20025587A NO323779B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
| NO20025588A NO20025588L (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
| NO20025586A NO323832B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20025587A NO323779B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
| NO20025588A NO20025588L (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
| NO20025586A NO323832B1 (no) | 2000-05-22 | 2002-11-21 | Inhibitorer for 11-beta-hydroxy steroid dehydrogenase type 1 |
Country Status (23)
| Country | Link |
|---|---|
| US (7) | US7030135B2 (enExample) |
| EP (4) | EP1283832B1 (enExample) |
| JP (4) | JP2003534336A (enExample) |
| KR (4) | KR20030011341A (enExample) |
| CN (4) | CN1430614A (enExample) |
| AR (1) | AR033534A1 (enExample) |
| AT (2) | ATE485283T1 (enExample) |
| AU (6) | AU6283101A (enExample) |
| BR (1) | BR0111099A (enExample) |
| CA (4) | CA2409697C (enExample) |
| DE (3) | DE60139931D1 (enExample) |
| EA (1) | EA005274B1 (enExample) |
| ES (1) | ES2333846T3 (enExample) |
| HU (1) | HUP0302435A3 (enExample) |
| IL (4) | IL152670A0 (enExample) |
| MX (1) | MXPA02011632A (enExample) |
| NO (4) | NO323831B1 (enExample) |
| NZ (4) | NZ522506A (enExample) |
| PE (1) | PE20020100A1 (enExample) |
| PL (1) | PL360137A1 (enExample) |
| SE (1) | SE0001899D0 (enExample) |
| WO (5) | WO2001090090A1 (enExample) |
| ZA (4) | ZA200209364B (enExample) |
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- 2001-05-22 AU AU2001262831A patent/AU2001262831B9/en not_active Ceased
- 2001-05-22 AU AU2001262830A patent/AU2001262830A1/en not_active Abandoned
- 2001-05-22 DE DE60143293T patent/DE60143293D1/de not_active Expired - Lifetime
- 2001-05-22 CN CNB018099661A patent/CN1188403C/zh not_active Expired - Fee Related
- 2001-05-22 CN CN01811609A patent/CN1437588A/zh active Pending
- 2001-05-22 AT AT01934782T patent/ATE485283T1/de not_active IP Right Cessation
- 2001-05-22 AT AT01937063T patent/ATE443055T1/de not_active IP Right Cessation
- 2001-05-22 AU AU6093201A patent/AU6093201A/xx not_active Withdrawn
- 2001-05-22 KR KR1020027015743A patent/KR20030016272A/ko not_active Withdrawn
- 2001-05-22 JP JP2001586279A patent/JP2003534337A/ja not_active Abandoned
- 2001-05-22 US US10/276,954 patent/US7125900B2/en not_active Expired - Fee Related
- 2001-05-22 NZ NZ522507A patent/NZ522507A/en unknown
- 2001-05-22 JP JP2001586282A patent/JP2003534339A/ja not_active Abandoned
- 2001-05-22 IL IL15279001A patent/IL152790A0/xx unknown
- 2001-05-22 KR KR1020027015703A patent/KR20030016269A/ko not_active Withdrawn
- 2001-05-22 EP EP01938885A patent/EP1283833A1/en not_active Withdrawn
- 2001-05-22 PL PL36013701A patent/PL360137A1/xx not_active IP Right Cessation
- 2001-05-22 AR ARP010102421A patent/AR033534A1/es not_active Application Discontinuation
- 2001-05-22 JP JP2001586280A patent/JP2003534338A/ja not_active Abandoned
- 2001-05-22 BR BR0111099-3A patent/BR0111099A/pt not_active IP Right Cessation
- 2001-05-22 EP EP01937063A patent/EP1283834B1/en not_active Expired - Lifetime
- 2001-05-22 EP EP01934781A patent/EP1283831A1/en not_active Withdrawn
- 2001-05-22 CA CA002408142A patent/CA2408142C/en not_active Expired - Fee Related
- 2001-05-22 CA CA002408783A patent/CA2408783A1/en not_active Abandoned
- 2001-05-22 CA CA002408144A patent/CA2408144C/en not_active Expired - Fee Related
- 2001-05-22 WO PCT/SE2001/001158 patent/WO2001090092A1/en not_active Ceased
- 2001-05-22 NZ NZ522591A patent/NZ522591A/en unknown
- 2001-05-22 IL IL15266901A patent/IL152669A0/xx unknown
- 2001-05-22 AU AU6093101A patent/AU6093101A/xx not_active Withdrawn
-
2002
- 2002-11-18 ZA ZA200209364A patent/ZA200209364B/en unknown
- 2002-11-18 ZA ZA200209359A patent/ZA200209359B/en unknown
- 2002-11-18 ZA ZA200209362A patent/ZA200209362B/en unknown
- 2002-11-18 ZA ZA200209360A patent/ZA200209360B/en unknown
- 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
- 2002-11-21 NO NO20025588A patent/NO20025588L/no not_active Application Discontinuation
- 2002-11-21 NO NO20025586A patent/NO323832B1/no not_active IP Right Cessation
-
2005
- 2005-11-30 US US11/289,634 patent/US20060160797A1/en not_active Abandoned
-
2006
- 2006-08-29 US US11/511,224 patent/US20060287374A1/en not_active Abandoned
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2009
- 2009-11-16 US US12/619,216 patent/US20100113435A1/en not_active Abandoned
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