NO313333B1 - Steroider substituert i posisjon 11, fremgangsmåte for fremstilling av disse, deres anvendelse samt farmasöytiskepreparater inneholdende disse - Google Patents
Steroider substituert i posisjon 11, fremgangsmåte for fremstilling av disse, deres anvendelse samt farmasöytiskepreparater inneholdende disse Download PDFInfo
- Publication number
- NO313333B1 NO313333B1 NO19993125A NO993125A NO313333B1 NO 313333 B1 NO313333 B1 NO 313333B1 NO 19993125 A NO19993125 A NO 19993125A NO 993125 A NO993125 A NO 993125A NO 313333 B1 NO313333 B1 NO 313333B1
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- general formula
- phenyl
- ethoxy
- lip
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 8
- 150000003431 steroids Chemical group 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 150000007513 acids Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- -1 alkyl radical Chemical class 0.000 claims description 18
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 18
- 125000003870 2-(1-piperidinyl)ethoxy group Chemical group [*]OC([H])([H])C([H])([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 208000001132 Osteoporosis Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000009245 menopause Effects 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 230000001076 estrogenic effect Effects 0.000 claims description 7
- 238000005755 formation reaction Methods 0.000 claims description 6
- 210000004291 uterus Anatomy 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000002657 hormone replacement therapy Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 22
- 230000000694 effects Effects 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 210000000988 bone and bone Anatomy 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 229960005309 estradiol Drugs 0.000 description 11
- 229930182833 estradiol Natural products 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000003480 eluent Substances 0.000 description 7
- 229910052814 silicon oxide Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 229940011871 estrogen Drugs 0.000 description 6
- 239000000262 estrogen Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000010261 cell growth Effects 0.000 description 4
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
- 238000009806 oophorectomy Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- LGHBWDKMGOIZKH-CBZIJGRNSA-N 3-Deoxyestrone Chemical compound C1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 LGHBWDKMGOIZKH-CBZIJGRNSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 206010017076 Fracture Diseases 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- 229910017974 NH40H Inorganic materials 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010065687 Bone loss Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 208000029725 Metabolic bone disease Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 206010049088 Osteopenia Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001270 agonistic effect Effects 0.000 description 2
- 230000001833 anti-estrogenic effect Effects 0.000 description 2
- CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 201000006828 endometrial hyperplasia Diseases 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 210000002414 leg Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 210000004216 mammary stem cell Anatomy 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 210000001672 ovary Anatomy 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 238000009256 replacement therapy Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000003200 Adenoma Diseases 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
- 208000033830 Hot Flashes Diseases 0.000 description 1
- 206010060800 Hot flush Diseases 0.000 description 1
- 208000008454 Hyperhidrosis Diseases 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000001395 anti-uterotrophic effect Effects 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000007295 breast benign neoplasm Diseases 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012351 deprotecting agent Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000004821 effect on bone Effects 0.000 description 1
- 230000000431 effect on proliferation Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002357 endometrial effect Effects 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000962 progestomimetic effect Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000004994 reproductive system Anatomy 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000002303 tibia Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 230000001836 utereotrophic effect Effects 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P5/32—Antioestrogens
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9615829A FR2757519B1 (fr) | 1996-12-23 | 1996-12-23 | Steroides substitues en position 11, leur procede de preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant |
| PCT/FR1997/002379 WO1998028324A1 (fr) | 1996-12-23 | 1997-12-22 | Steroides substitues en position 11, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993125D0 NO993125D0 (no) | 1999-06-23 |
| NO993125L NO993125L (no) | 1999-08-20 |
| NO313333B1 true NO313333B1 (no) | 2002-09-16 |
Family
ID=9498983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993125A NO313333B1 (no) | 1996-12-23 | 1999-06-23 | Steroider substituert i posisjon 11, fremgangsmåte for fremstilling av disse, deres anvendelse samt farmasöytiskepreparater inneholdende disse |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US6207657B1 (de) |
| EP (1) | EP0946585B1 (de) |
| JP (1) | JP4376319B2 (de) |
| KR (1) | KR20000062288A (de) |
| CN (1) | CN1247541A (de) |
| AP (1) | AP9901567A0 (de) |
| AR (1) | AR010857A1 (de) |
| AT (1) | ATE216396T1 (de) |
| AU (1) | AU726350B2 (de) |
| BR (1) | BR9714433A (de) |
| CA (1) | CA2275955A1 (de) |
| CZ (1) | CZ227899A3 (de) |
| DE (1) | DE69712095T2 (de) |
| DK (1) | DK0946585T3 (de) |
| EA (1) | EA001868B1 (de) |
| ES (1) | ES2174329T3 (de) |
| FR (1) | FR2757519B1 (de) |
| HR (1) | HRP970711B1 (de) |
| HU (1) | HUP0001447A3 (de) |
| ID (1) | ID22627A (de) |
| IL (1) | IL130509A0 (de) |
| NO (1) | NO313333B1 (de) |
| NZ (1) | NZ336224A (de) |
| PL (1) | PL334124A1 (de) |
| PT (1) | PT946585E (de) |
| SI (1) | SI0946585T1 (de) |
| SK (1) | SK83099A3 (de) |
| TR (1) | TR199901453T2 (de) |
| TW (1) | TW492974B (de) |
| UA (1) | UA54483C2 (de) |
| WO (1) | WO1998028324A1 (de) |
| YU (1) | YU29299A (de) |
| ZA (1) | ZA9711324B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2757519B1 (fr) * | 1996-12-23 | 1999-06-11 | Hoechst Marion Roussel Inc | Steroides substitues en position 11, leur procede de preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant |
| FR2780060B1 (fr) * | 1998-06-23 | 2000-08-04 | Hoechst Marion Roussel Inc | Nouveaux 19-nor steroides 17-halogenes, procede et intermediaires de preparation, application comme medicaments et compositions pharmaceutiques les renfermant |
| DE19929715A1 (de) | 1999-06-24 | 2000-12-28 | Schering Ag | 11ß-langkettig-substituierte Estratriene, Verfahren zur Herstellung , pharmazeutische Präparate, die diese 11ß-langkettig-substituierten Estratriene enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
| FR2826004B1 (fr) * | 2001-06-13 | 2008-03-28 | Aventis Pharma Sa | Procede de preparation de derives estrogenes |
| FR2854402B1 (fr) * | 2003-04-29 | 2008-07-04 | Aventis Pharma Sa | Nouveau procede et intermediaires de preparation de composes 19-nor-steroides |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2640977A2 (en) * | 1982-06-11 | 1990-06-29 | Roussel Uclaf | New position-11 substituted 19-norsteroids and their application as medicinal products. |
| US4859585A (en) * | 1986-04-17 | 1989-08-22 | Trustees Of Tufts College | In-vitro methods for identifying compositions which are agonists and antagonists of estrogens |
| FR2643638B1 (fr) * | 1989-02-24 | 1991-06-14 | Roussel Uclaf | Nouveaux 19-nor steroides ayant en position 11beta une chaine carbonee comportant une fonction amide ou carbamate, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| JP3377856B2 (ja) * | 1993-03-25 | 2003-02-17 | イスクラ産業株式会社 | 骨吸収抑制・骨形成促進化合物 |
| DE4329867C1 (de) * | 1993-09-03 | 1994-09-15 | Siemens Ag | Stromspiegel |
| FR2757519B1 (fr) * | 1996-12-23 | 1999-06-11 | Hoechst Marion Roussel Inc | Steroides substitues en position 11, leur procede de preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant |
| FR2757399B1 (fr) * | 1996-12-23 | 1999-12-17 | Hoechst Marion Roussel Inc | Application de composes steroides substitues en 11 pour la fabrication de medicaments ayant une activite estrogene dissociee |
| FR2761992B1 (fr) * | 1997-04-09 | 1999-06-11 | Hoechst Marion Roussel Inc | Nouveaux steroides 4-halogenes, leur procede et intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| FR2771096B1 (fr) * | 1997-11-17 | 2000-08-11 | Hoechst Marion Roussel Inc | Nouveaux 19-nor steroides, substitues en position 11beta, procede et intermediaires de preparation, application comme medicaments et compositions pharmaceutiques les renfermant |
-
1996
- 1996-12-23 FR FR9615829A patent/FR2757519B1/fr not_active Expired - Fee Related
-
1997
- 1997-12-17 ZA ZA9711324A patent/ZA9711324B/xx unknown
- 1997-12-22 EA EA199900588A patent/EA001868B1/ru not_active IP Right Cessation
- 1997-12-22 SK SK830-99A patent/SK83099A3/sk unknown
- 1997-12-22 PT PT97952972T patent/PT946585E/pt unknown
- 1997-12-22 HU HU0001447A patent/HUP0001447A3/hu unknown
- 1997-12-22 DE DE69712095T patent/DE69712095T2/de not_active Expired - Lifetime
- 1997-12-22 US US09/331,823 patent/US6207657B1/en not_active Expired - Lifetime
- 1997-12-22 YU YU29299A patent/YU29299A/sh unknown
- 1997-12-22 ID IDW990573A patent/ID22627A/id unknown
- 1997-12-22 IL IL13050997A patent/IL130509A0/xx unknown
- 1997-12-22 UA UA99074263A patent/UA54483C2/uk unknown
- 1997-12-22 KR KR1019997005685A patent/KR20000062288A/ko not_active Application Discontinuation
- 1997-12-22 EP EP97952972A patent/EP0946585B1/de not_active Expired - Lifetime
- 1997-12-22 AU AU56678/98A patent/AU726350B2/en not_active Ceased
- 1997-12-22 CA CA002275955A patent/CA2275955A1/fr not_active Abandoned
- 1997-12-22 AP APAP/P/1999/001567A patent/AP9901567A0/en unknown
- 1997-12-22 ES ES97952972T patent/ES2174329T3/es not_active Expired - Lifetime
- 1997-12-22 DK DK97952972T patent/DK0946585T3/da active
- 1997-12-22 BR BR9714433-9A patent/BR9714433A/pt not_active IP Right Cessation
- 1997-12-22 NZ NZ336224A patent/NZ336224A/en unknown
- 1997-12-22 SI SI9730353T patent/SI0946585T1/xx unknown
- 1997-12-22 TR TR1999/01453T patent/TR199901453T2/xx unknown
- 1997-12-22 CZ CZ992278A patent/CZ227899A3/cs unknown
- 1997-12-22 PL PL97334124A patent/PL334124A1/xx unknown
- 1997-12-22 JP JP52847398A patent/JP4376319B2/ja not_active Expired - Fee Related
- 1997-12-22 CN CN97181921A patent/CN1247541A/zh active Pending
- 1997-12-22 AT AT97952972T patent/ATE216396T1/de not_active IP Right Cessation
- 1997-12-22 WO PCT/FR1997/002379 patent/WO1998028324A1/fr not_active Application Discontinuation
- 1997-12-23 AR ARP970106163A patent/AR010857A1/es unknown
- 1997-12-23 HR HR970711A patent/HRP970711B1/xx not_active IP Right Cessation
-
1998
- 1998-02-06 TW TW086119813A patent/TW492974B/zh active
-
1999
- 1999-06-23 NO NO19993125A patent/NO313333B1/no unknown
-
2000
- 2000-06-13 US US09/592,710 patent/US6482813B1/en not_active Expired - Lifetime
-
2002
- 2002-02-14 US US10/075,364 patent/US6541464B2/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO1999033859A9 (en) | Novel anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use | |
| JPH07149790A (ja) | 新規な１１−ベンズアルドキシム−１７β−メトキシ−１７α−メトキシメチル−エストラジエン誘導体、その製法およびその物質を含有する医薬製剤 | |
| NO313333B1 (no) | Steroider substituert i posisjon 11, fremgangsmåte for fremstilling av disse, deres anvendelse samt farmasöytiskepreparater inneholdende disse | |
| US6479476B1 (en) | 19-nor steroids substituted in position 11β, preparation method and intermediates, application as medicines and pharmaceutical compositions containing them | |
| US6239121B1 (en) | 4- Halogenated steroids, preparation method and intermediates, application as medicines and pharmaceutical compositions containing same | |
| JP4263264B2 (ja) | 解離したエストロゲン活性を有する薬剤を製造するための１１位置換ステロイド化合物の用途 | |
| WO1998028324A9 (fr) | Steroides substitues en position 11, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant | |
| NO318381B1 (no) | 17-halogenerte 19-nor-steroidforbindelser og mellomprodukter for disse, fremgangsmate for fremstilling av steroidforbindelsene, medikamenter inneholdende steroidforbindelsene og anvendelse av steroidforbindelsene. | |
| MXPA99005841A (en) | Steroids substituted in position 11, method of preparation, application as medicines and pharmaceutical compositions containing them | |
| MXPA00012483A (en) | Novel 17-halogenated 19-nor steroids, method and intermediates for preparing same, use as medicines and pharmaceutical compositions containing same |