BG64212B1 - Нестероидни (хетеро) циклични заместени ациланилиди със смесена гестагенна и андрогенна активност - Google Patents
Нестероидни (хетеро) циклични заместени ациланилиди със смесена гестагенна и андрогенна активност Download PDFInfo
- Publication number
- BG64212B1 BG64212B1 BG103903A BG10390399A BG64212B1 BG 64212 B1 BG64212 B1 BG 64212B1 BG 103903 A BG103903 A BG 103903A BG 10390399 A BG10390399 A BG 10390399A BG 64212 B1 BG64212 B1 BG 64212B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- hydroxy
- methyl
- trifluoromethyl
- phthalide
- valeroylamino
- Prior art date
Links
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 12
- 230000000694 effects Effects 0.000 title abstract description 5
- 125000005842 heteroatom Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- -1 C 15 alkoxy groups Chemical group 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- PMUREGUVCLMOBE-UHFFFAOYSA-N 4-(3-fluoro-4-methoxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C(F)C(OC)=CC=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 PMUREGUVCLMOBE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- WLTUFOLTUJPUBM-UHFFFAOYSA-N 2-hydroxy-n-(1-oxo-3h-2-benzofuran-5-yl)-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 WLTUFOLTUJPUBM-UHFFFAOYSA-N 0.000 claims description 4
- OBBFRGLSKUBWLV-UHFFFAOYSA-N 5-[[2-hydroxy-4-phenyl-2-(trifluoromethyl)pentyl]amino]-3h-2-benzofuran-1-one Chemical compound C=1C=C2C(=O)OCC2=CC=1NCC(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 OBBFRGLSKUBWLV-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- QLUBLXFYVSMPSA-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxy-5-methylphenyl)-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound CC1=CC=C(O)C(C(C)(C)CC(O)(C(=O)NC=2C=C3COC(=O)C3=CC=2)C(F)(F)F)=C1 QLUBLXFYVSMPSA-UHFFFAOYSA-N 0.000 claims description 3
- BPBUAOIZTSGINR-UHFFFAOYSA-N 2-hydroxy-4-(2-methoxyphenyl)-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=CC=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 BPBUAOIZTSGINR-UHFFFAOYSA-N 0.000 claims description 3
- JKXKUNVXIQAJFN-UHFFFAOYSA-N 2-hydroxy-4-methyl-4-(3-methylphenyl)-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound CC1=CC=CC(C(C)(C)CC(O)(C(=O)NC=2C=C3COC(=O)C3=CC=2)C(F)(F)F)=C1 JKXKUNVXIQAJFN-UHFFFAOYSA-N 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000002184 metal Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- PLCAABVVJJBUAK-UHFFFAOYSA-N n-(4-bromo-1-oxo-3h-2-benzofuran-5-yl)-2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=C(Br)C=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 PLCAABVVJJBUAK-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- MIWUNJGJUSWHTO-UHFFFAOYSA-N 2-hydroxy-2,4-dimethyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-4-phenylpentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(C)(O)CC(C)(C)C1=CC=CC=C1 MIWUNJGJUSWHTO-UHFFFAOYSA-N 0.000 claims description 2
- UHWYYRRPRWSREZ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyphenyl)-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1O UHWYYRRPRWSREZ-UHFFFAOYSA-N 0.000 claims description 2
- ARVKBGMQLPESSL-UHFFFAOYSA-N 2-hydroxy-4-(3-methoxyphenyl)-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=CC(C(C)(C)CC(O)(C(=O)NC=2C=C3COC(=O)C3=CC=2)C(F)(F)F)=C1 ARVKBGMQLPESSL-UHFFFAOYSA-N 0.000 claims description 2
- NPPYLQXHYGVYSC-UHFFFAOYSA-N 2-hydroxy-4-(4-methoxyphenyl)-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=CC(OC)=CC=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 NPPYLQXHYGVYSC-UHFFFAOYSA-N 0.000 claims description 2
- ALGMWCHRJYAMPE-UHFFFAOYSA-N 2-hydroxy-4-methyl-4-(4-methylphenyl)-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=CC(C)=CC=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 ALGMWCHRJYAMPE-UHFFFAOYSA-N 0.000 claims description 2
- XQWVCRMHQFWIJK-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(1,1,2,2,2-pentafluoroethyl)-4-phenylpentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)C(F)(F)F)CC(C)(C)C1=CC=CC=C1 XQWVCRMHQFWIJK-UHFFFAOYSA-N 0.000 claims description 2
- RRLLTJYTLKIFIA-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 RRLLTJYTLKIFIA-UHFFFAOYSA-N 0.000 claims description 2
- WXSZIQKPURGKJK-UHFFFAOYSA-N 3,3,3-trifluoro-2-hydroxy-n-(1-oxo-3h-2-benzofuran-5-yl)-2-[(1-phenylcyclobutyl)methyl]propanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(C(F)(F)F)(O)CC1(C=2C=CC=CC=2)CCC1 WXSZIQKPURGKJK-UHFFFAOYSA-N 0.000 claims description 2
- VJRWSVPZGINQNF-UHFFFAOYSA-N 4-(2-fluorophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1F VJRWSVPZGINQNF-UHFFFAOYSA-N 0.000 claims description 2
- IKCMGPLMWGFPCL-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C(C)C(C)=CC=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 IKCMGPLMWGFPCL-UHFFFAOYSA-N 0.000 claims description 2
- XPQDHEURWYQAHH-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound CC1=CC(C)=CC(C(C)(C)CC(O)(C(=O)NC=2C=C3COC(=O)C3=CC=2)C(F)(F)F)=C1 XPQDHEURWYQAHH-UHFFFAOYSA-N 0.000 claims description 2
- HXGXSEYCGYIYJP-UHFFFAOYSA-N 4-(3-fluoro-4-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(O)C(F)=C1 HXGXSEYCGYIYJP-UHFFFAOYSA-N 0.000 claims description 2
- NAMFGOIXJRGBGF-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 NAMFGOIXJRGBGF-UHFFFAOYSA-N 0.000 claims description 2
- OALNIHHIJNCQJK-UHFFFAOYSA-N 4-(4-bromophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(Br)C=C1 OALNIHHIJNCQJK-UHFFFAOYSA-N 0.000 claims description 2
- TXADCVUNZMNKRU-UHFFFAOYSA-N 4-(4-bromophenyl)-n-(4-ethyl-1-oxo-2,3-benzoxazin-6-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(CC)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(Br)C=C1 TXADCVUNZMNKRU-UHFFFAOYSA-N 0.000 claims description 2
- MCHYUIBRKGUBJA-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(Cl)C=C1 MCHYUIBRKGUBJA-UHFFFAOYSA-N 0.000 claims description 2
- NXPOOHHYDLOLJC-UHFFFAOYSA-N 4-(4-cyanophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(C#N)C=C1 NXPOOHHYDLOLJC-UHFFFAOYSA-N 0.000 claims description 2
- PMVUAXQBHPXSJB-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 PMVUAXQBHPXSJB-UHFFFAOYSA-N 0.000 claims description 2
- OOXBRSLQDAMBIS-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(Cl)=CC=C1O OOXBRSLQDAMBIS-UHFFFAOYSA-N 0.000 claims description 2
- UYXURLMCUPZVQR-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=C(Cl)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 UYXURLMCUPZVQR-UHFFFAOYSA-N 0.000 claims description 2
- WUXTURZHMMFRPK-UHFFFAOYSA-N 4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O WUXTURZHMMFRPK-UHFFFAOYSA-N 0.000 claims description 2
- DAYFWNQOWUPASA-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 DAYFWNQOWUPASA-UHFFFAOYSA-N 0.000 claims description 2
- GIBZLWRPPUSMTC-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C2C(=O)ON=C(C)C2=C1 GIBZLWRPPUSMTC-UHFFFAOYSA-N 0.000 claims description 2
- ULPOSDMVRAOCKS-UHFFFAOYSA-N 4-ethyl-6-[[2-hydroxy-4-phenyl-2-(trifluoromethyl)pentyl]amino]-2,3-benzoxazin-1-one Chemical compound C1=C2C(CC)=NOC(=O)C2=CC=C1NCC(O)(C(F)(F)F)CC(C)C1=CC=CC=C1 ULPOSDMVRAOCKS-UHFFFAOYSA-N 0.000 claims description 2
- XBVAUUNBWQQMFT-UHFFFAOYSA-N 5-[[4-(4-fluorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-3h-2-benzofuran-1-one Chemical compound C=1C=C2C(=O)OCC2=CC=1NCC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 XBVAUUNBWQQMFT-UHFFFAOYSA-N 0.000 claims description 2
- QNDBLFHVAMTSHZ-UHFFFAOYSA-N 5-[[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino]-3h-2-benzofuran-1-one Chemical compound C=1C=C2C(=O)OCC2=CC=1NCC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O QNDBLFHVAMTSHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- GGKXKUXDVBOPLP-UHFFFAOYSA-N n-(4-ethyl-1-oxo-2,3-benzoxazin-6-yl)-2-hydroxy-4-(2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(CC)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1OC GGKXKUXDVBOPLP-UHFFFAOYSA-N 0.000 claims description 2
- KGLJRRLKPPYOCC-UHFFFAOYSA-N n-(4-ethyl-1-oxo-2,3-benzoxazin-6-yl)-2-hydroxy-4-methyl-4-(4-methylphenyl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(CC)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(C)C=C1 KGLJRRLKPPYOCC-UHFFFAOYSA-N 0.000 claims description 2
- OJPKVUHBRDJGND-UHFFFAOYSA-N n-(4-ethyl-1-oxo-2,3-benzoxazin-6-yl)-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(CC)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OC OJPKVUHBRDJGND-UHFFFAOYSA-N 0.000 claims description 2
- GNHYCJPMLVTXIS-UHFFFAOYSA-N n-(6-bromo-1-oxo-3h-2-benzofuran-5-yl)-2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=2COC(=O)C=2C=C(Br)C=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 GNHYCJPMLVTXIS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 4
- GDEAUCMWYHCGMG-UHFFFAOYSA-N 1,1,1-trifluoro-2-[[4-nitro-3-(trifluoromethyl)anilino]methyl]-4-phenylpentan-2-ol Chemical compound C=1C=CC=CC=1C(C)CC(O)(C(F)(F)F)CNC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 GDEAUCMWYHCGMG-UHFFFAOYSA-N 0.000 claims 3
- 150000001555 benzenes Chemical class 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- PLVFZQGMURDXFJ-UHFFFAOYSA-N 2-hydroxy-4,4-dimethyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)hex-5-enamide Chemical compound C=CC(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C2C(=O)OCC2=C1 PLVFZQGMURDXFJ-UHFFFAOYSA-N 0.000 claims 1
- RWPQPKDKLPQMOY-UHFFFAOYSA-N 2-hydroxy-4-(2-methoxy-5-methylphenyl)-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=C(C)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 RWPQPKDKLPQMOY-UHFFFAOYSA-N 0.000 claims 1
- BLTQUBIYGAFBBY-UHFFFAOYSA-N 2-hydroxy-4-(2-methoxyphenyl)-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=CC=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C2C(=O)ON=C(C)C2=C1 BLTQUBIYGAFBBY-UHFFFAOYSA-N 0.000 claims 1
- GKOISAITVMDQGW-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-[1-oxo-4-(trifluoromethyl)-2,3-benzoxazin-6-yl]-4-phenyl-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C(C(ON=C2C(F)(F)F)=O)C2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 GKOISAITVMDQGW-UHFFFAOYSA-N 0.000 claims 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 108090000468 progesterone receptors Proteins 0.000 description 1
- 229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009256 replacement therapy Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003515 testosterones Chemical class 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 229940100640 transdermal system Drugs 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/34—Gestagens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/02—1,2-Oxazines; Hydrogenated 1,2-oxazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Materials For Medical Uses (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19723722A DE19723722A1 (de) | 1997-05-30 | 1997-05-30 | Nichtsteroidale Gestagene |
PCT/EP1998/003242 WO1998054159A1 (de) | 1997-05-30 | 1998-06-02 | Nichtsteroidale (hetero)zyklisch-substituierte acylanilide mit gemischter gestagener und androgener wirksamkeit |
Publications (2)
Publication Number | Publication Date |
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BG103903A BG103903A (en) | 2000-04-28 |
BG64212B1 true BG64212B1 (bg) | 2004-05-31 |
Family
ID=7831567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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BG103903A BG64212B1 (bg) | 1997-05-30 | 1999-11-19 | Нестероидни (хетеро) циклични заместени ациланилиди със смесена гестагенна и андрогенна активност |
Country Status (30)
Country | Link |
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EP (1) | EP0986545B1 (cs) |
JP (1) | JP2002502385A (cs) |
KR (1) | KR100536870B1 (cs) |
CN (1) | CN100445272C (cs) |
AR (1) | AR011480A1 (cs) |
AT (1) | ATE286035T1 (cs) |
AU (1) | AU747083C (cs) |
BG (1) | BG64212B1 (cs) |
BR (1) | BR9809703A (cs) |
CA (1) | CA2305458C (cs) |
CZ (1) | CZ296377B6 (cs) |
DE (2) | DE19723722A1 (cs) |
EA (1) | EA004306B1 (cs) |
EE (1) | EE04492B1 (cs) |
ES (1) | ES2234121T3 (cs) |
HR (1) | HRP980289B1 (cs) |
HU (1) | HUP0002126A3 (cs) |
ID (1) | ID23499A (cs) |
IL (2) | IL133195A0 (cs) |
IS (1) | IS2498B (cs) |
NO (1) | NO325076B1 (cs) |
NZ (1) | NZ501359A (cs) |
PL (1) | PL197887B1 (cs) |
PT (1) | PT986545E (cs) |
SK (1) | SK284943B6 (cs) |
TR (1) | TR199902924T2 (cs) |
TW (1) | TW577882B (cs) |
UA (1) | UA64752C2 (cs) |
WO (1) | WO1998054159A1 (cs) |
ZA (1) | ZA984655B (cs) |
Families Citing this family (100)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19856475A1 (de) * | 1998-11-27 | 2000-05-31 | Schering Ag | Nichtsteroidale Entzündungshemmer |
DE10038639A1 (de) | 2000-07-28 | 2002-02-21 | Schering Ag | Nichtsteroidale Entzündungshemmer |
DE10346940B3 (de) * | 2003-10-06 | 2005-06-16 | Schering Ag | Substituierte Pentanole, ihre Verwendung zur Herstellung von Arzneimitteln speziell Entzündungshemmer sowie diese enthaltende pharmazeutische Präparate |
EP1373888A2 (en) * | 2000-12-28 | 2004-01-02 | Schering Aktiengesellschaft | Method for screening for progesterone receptor isoform-specific ligands |
CA2472746A1 (en) * | 2002-01-14 | 2003-07-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof |
DK1482925T3 (da) * | 2002-03-11 | 2007-05-14 | Bayer Schering Pharma Ag | 5- (2-hydroxy-3 -'1 - (3-trifluormethylphenyl) cyclopropylpropionylamino) phtalid og relaterede forbindelser med progesteronreceptormoducerende aktivitet til anvendelse i fertilitetskontrol og hormonerstatningsterapi |
EP1344776A1 (en) * | 2002-03-11 | 2003-09-17 | Schering Aktiengesellschaft | 5- 2-hydroxy-3-[1-(3-trifluoromethylphenyl)-cyclopropyl]-propionylamino -phtalide and 6- 2-hydroxy-3-[1-(3-trifluoromethylphenyl)-cyclopropyl]-propionylamino -4-methyl-2,3-benzoxazin-1-one derivatives with progesterone receptor modulating activity for use in fertility control, hormone replacement therapy and the treatment of gynecological disorders |
US7268152B2 (en) | 2002-03-26 | 2007-09-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
ES2298508T3 (es) | 2002-03-26 | 2008-05-16 | Boehringer Ingelheim Pharmaceuticals Inc. | Mimeticos de glucocorticoides, metodos para prepararlos, composiciones farmaceuticas y sus usos. |
DE10215316C1 (de) * | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
US7186864B2 (en) | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
US7074806B2 (en) | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
WO2004018429A2 (en) | 2002-08-21 | 2004-03-04 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted hihydroquinolines as glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
EA011095B1 (ru) | 2002-08-29 | 2008-12-30 | Бёрингер Ингельхайм Фармасьютиклз, Инк. | Производные 3-(сульфонамидоэтил)индола, предназначенные для использования в качестве миметиков глюкокортикоидов при лечении воспалительных, аллергических и пролиферативных заболеваний |
CA2501867A1 (en) * | 2002-10-15 | 2004-04-29 | James T. Dalton | Heterocyclic selective androgen receptor modulators and methods of use thereof |
DE10261874A1 (de) * | 2002-12-20 | 2004-07-08 | Schering Ag | Nichtsteroidale Entzündungshemmer |
EP1583745A1 (en) | 2003-01-03 | 2005-10-12 | Boehringer Ingelheim Pharmaceuticals Inc. | 1-propanol and 1-propylamine derivatives and their use as glucocorticoid ligands |
US20040224992A1 (en) * | 2003-02-27 | 2004-11-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
WO2005003098A1 (de) * | 2003-07-01 | 2005-01-13 | Schering Aktiengesellschaft | Heterozyklisch substituierte pentanol-derivate, verfahren zu ihrer herstellung und ihre verwendung als entzündungshemmer |
GB0316290D0 (en) | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
UY28526A1 (es) | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
ES2290769T3 (es) | 2003-10-16 | 2008-02-16 | Boehringer Ingelheim Pharmaceuticals Inc. | Sintesis estereoselectiva de ciertos alcoholes substituidos con trifluormetilo. |
US7795272B2 (en) | 2004-03-13 | 2010-09-14 | Boehringer Ingelheim Pharmaceutical, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof |
PE20060272A1 (es) | 2004-05-24 | 2006-05-22 | Glaxo Group Ltd | (2r,3r,4s,5r,2'r,3'r,4's,5's)-2,2'-{trans-1,4-ciclohexanodiilbis-[imino(2-{[2-(1-metil-1h-imidazol-4-il)etil]amino}-9h-purin-6,9-diil)]}bis[5-(2-etil-2h-tetrazol-5-il)tetrahidro-3,4-furanodiol] como agonista a2a |
TWI307630B (en) | 2004-07-01 | 2009-03-21 | Glaxo Group Ltd | Immunoglobulins |
DE102004062182B4 (de) * | 2004-12-20 | 2007-06-06 | Bayer Schering Pharma Ag | Transdermales Pflaster mit Progesteron A-Spezifische Liganden (PRASL) als Wirkstoff |
JP2008525525A (ja) | 2004-12-27 | 2008-07-17 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | グルココルチコイドミメティクス、その製法、医薬組成物及び使用 |
JP5281291B2 (ja) | 2005-01-10 | 2013-09-04 | グラクソ グループ リミテッド | 新規化合物 |
WO2006083030A1 (ja) * | 2005-02-04 | 2006-08-10 | Ajinomoto Co., Inc. | 脂肪酸の製造方法および脂肪酸の塩結晶 |
UY29440A1 (es) | 2005-03-25 | 2006-10-02 | Glaxo Group Ltd | Nuevos compuestos |
AR053450A1 (es) | 2005-03-25 | 2007-05-09 | Glaxo Group Ltd | Derivados de 3,4-dihidro-pirimido(4,5-d)pirimidin-2-(1h)-ona 1,5,7 trisustituidos como inhibidores de la quinasa p38 |
DE102005017326A1 (de) * | 2005-04-14 | 2007-03-29 | Schering Ag | Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
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1997
- 1997-05-30 DE DE19723722A patent/DE19723722A1/de not_active Ceased
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- 1998-02-06 UA UA99127245A patent/UA64752C2/uk unknown
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- 1998-06-02 BR BR9809703-2A patent/BR9809703A/pt not_active IP Right Cessation
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