JPH0469639B2 - - Google Patents
Info
- Publication number
- JPH0469639B2 JPH0469639B2 JP59502899A JP50289984A JPH0469639B2 JP H0469639 B2 JPH0469639 B2 JP H0469639B2 JP 59502899 A JP59502899 A JP 59502899A JP 50289984 A JP50289984 A JP 50289984A JP H0469639 B2 JPH0469639 B2 JP H0469639B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- steroid
- group
- ethynyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003431 steroids Chemical class 0.000 description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 38
- 238000000034 method Methods 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- -1 Ethinyl steroids Chemical class 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000000938 luteal effect Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000004043 oxo group Chemical group O=* 0.000 description 7
- 239000003433 contraceptive agent Substances 0.000 description 6
- 239000000186 progesterone Substances 0.000 description 6
- 229960003387 progesterone Drugs 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 210000004246 corpus luteum Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000262 estrogen Substances 0.000 description 4
- 229940011871 estrogen Drugs 0.000 description 4
- 230000003054 hormonal effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000583 progesterone congener Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VTHUYJIXSMGYOQ-KOORYGTMSA-N 17-hydroxyprogesterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 VTHUYJIXSMGYOQ-KOORYGTMSA-N 0.000 description 3
- 206010006187 Breast cancer Diseases 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940124558 contraceptive agent Drugs 0.000 description 3
- 230000002254 contraceptive effect Effects 0.000 description 3
- 230000012173 estrus Effects 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 239000003270 steroid hormone Substances 0.000 description 3
- QUZMIAJIRIZFQN-UHFFFAOYSA-N (e)-diazo(dimethoxyphosphoryl)methane Chemical compound COP(=O)(OC)C=[N+]=[N-] QUZMIAJIRIZFQN-UHFFFAOYSA-N 0.000 description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- 230000002280 anti-androgenic effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 108091008039 hormone receptors Proteins 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 206010020718 hyperplasia Diseases 0.000 description 2
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- HCNXGNNHDVDCAN-UHFFFAOYSA-N (4-methyl-4-oxo-1,3,2,4lambda5-dioxazaphosphetidin-2-ium-2-ylidene)azanide Chemical compound CP1(O[N+](=[N-])O1)=O HCNXGNNHDVDCAN-UHFFFAOYSA-N 0.000 description 1
- BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 241000349731 Afzelia bipindensis Species 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010014733 Endometrial cancer Diseases 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000037093 Menstruation Disturbances Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 102000001307 androgen receptors Human genes 0.000 description 1
- 108010080146 androgen receptors Proteins 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000051 antiandrogen Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- ZMTGVHOZRMCZNY-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine;hydrochloride Chemical compound Cl.O[Cr](O)(=O)=O.C1=CC=NC=C1 ZMTGVHOZRMCZNY-UHFFFAOYSA-L 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000004696 endometrium Anatomy 0.000 description 1
- 229960002568 ethinylestradiol Drugs 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 231100000508 hormonal effect Toxicity 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000029849 luteinization Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960002985 medroxyprogesterone acetate Drugs 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical group C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 231100000544 menstrual irregularity Toxicity 0.000 description 1
- IMSSROKUHAOUJS-MJCUULBUSA-N mestranol Chemical compound C1C[C@]2(C)[C@@](C#C)(O)CC[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 IMSSROKUHAOUJS-MJCUULBUSA-N 0.000 description 1
- 229960001390 mestranol Drugs 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 102000003998 progesterone receptors Human genes 0.000 description 1
- 108090000468 progesterone receptors Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003515 testosterones Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Electroluminescent Light Sources (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/517,457 US4512986A (en) | 1983-07-26 | 1983-07-26 | Progrestationally active steroids |
| US517457 | 1983-07-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60502100A JPS60502100A (ja) | 1985-12-05 |
| JPH0469639B2 true JPH0469639B2 (en, 2012) | 1992-11-06 |
Family
ID=24059873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59502899A Granted JPS60502100A (ja) | 1983-07-26 | 1984-07-26 | 黄体活性を示すステロイド |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4512986A (en, 2012) |
| EP (1) | EP0152429B1 (en, 2012) |
| JP (1) | JPS60502100A (en, 2012) |
| AU (1) | AU583476B2 (en, 2012) |
| DE (1) | DE3480094D1 (en, 2012) |
| WO (1) | WO1985000609A1 (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8517360D0 (en) * | 1985-07-09 | 1985-08-14 | Erba Farmitalia | Substituted androsta-1,4-diene-3,17-diones |
| US4963540A (en) * | 1986-04-16 | 1990-10-16 | Maxson Wayne S | Method for treatment of premenstrual syndrome |
| GB8801697D0 (en) * | 1988-01-26 | 1988-02-24 | Erba Farmitalia | Improvements in synthesis of 6-methylene derivatives of androsta-1 4-diene-3 17-dione |
| FR2679236B1 (fr) * | 1991-07-18 | 1997-01-24 | Theramex | Nouveaux sterouides substitues en position 6, leurs procedes d'obtention et des compositions pharmaceutiques en renfermant. |
| US5661141A (en) * | 1995-03-27 | 1997-08-26 | Petrow; Vladimir | 19-oxygenated steroids as therapeutic agents |
| US6020328A (en) | 1998-03-06 | 2000-02-01 | Research Triangle Institute | 20-keto-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| ATE473759T1 (de) | 1998-05-22 | 2010-07-15 | Univ Leland Stanford Junior | Bifunktionelle moleküle sowie darauf basierende therapien. |
| US6667050B1 (en) | 1999-04-06 | 2003-12-23 | Galen (Chemicals) Limited | Chewable oral contraceptive |
| US7459445B2 (en) * | 2000-03-10 | 2008-12-02 | Duramed Pharmaceuticals, Inc. | Estrogenic compounds and topical pharmaceutical formulations of the same |
| US7989436B2 (en) | 2003-07-23 | 2011-08-02 | Duramed Pharmaceuticals, Inc. | Estrogenic compounds and pharmaceutical formulations comprising the same |
| US6660726B2 (en) | 2000-03-10 | 2003-12-09 | Endeavor Pharmaceuticals | Estrogenic compounds, pharmaceutical compositions thereof, and methods of using same |
| US6855703B1 (en) | 2000-03-10 | 2005-02-15 | Endeavor Pharmaceuticals | Pharmaceutical compositions of conjugated estrogens and methods of analyzing mixtures containing estrogenic compounds |
| AU2003267788A1 (en) * | 2002-10-25 | 2004-05-13 | Pfizer Products Inc. | Novel injectable depot formulations |
| US6992075B2 (en) * | 2003-04-04 | 2006-01-31 | Barr Laboratories, Inc. | C(14) estrogenic compounds |
| US20040259851A1 (en) * | 2003-04-11 | 2004-12-23 | Leonard Thomas W. | Methods of administering estrogens and progestins |
| CA2569738A1 (en) * | 2004-06-07 | 2005-12-22 | Duramed Pharmaceuticals, Inc. | Dispenser for progestin used for acute and maintenance treatment of dub |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| US9062126B2 (en) | 2005-09-16 | 2015-06-23 | Raptor Pharmaceuticals Inc. | Compositions comprising receptor-associated protein (RAP) variants specific for CR-containing proteins and uses thereof |
| DE102007027637A1 (de) | 2007-06-12 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | 17ß-Cyano-19-nor-androst-4-en-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel |
| DE102007027635A1 (de) * | 2007-06-12 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | 17ß-Cyano-19-androst-4-en-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel |
| NZ616673A (en) | 2009-02-20 | 2014-08-29 | To Bbb Holding B V | Glutathione-based drug delivery system |
| MX2011011833A (es) | 2009-05-06 | 2012-01-27 | Lab Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de partículas de fosfato de calcio-agente activo y métodos para utilizar las mismas. |
| RU2649757C1 (ru) * | 2016-12-16 | 2018-04-04 | Общество с ограниченной ответственностью "Научно-производственная компания "СКиФФ" | Пероральная форма бигормональной композиции для регуляции половой охоты у мелких домашних животных (варианты) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB337823I5 (en, 2012) * | 1959-09-25 | 1976-03-23 | ||
| US3361744A (en) * | 1962-07-18 | 1968-01-02 | American Cyanamid Co | Novel 17-hydrocarbon substituted progesterones, intermediates and methods of preparing the same |
| US3846456A (en) * | 1965-04-07 | 1974-11-05 | Upjohn Co | Organic compounds |
| GB1159434A (en) * | 1965-08-16 | 1969-07-23 | Glaxo Lab Ltd | 11beta&;-Fluoro-19-nor-Steroids |
| GB1235285A (en) * | 1967-07-28 | 1971-06-09 | Organon Labor Ltd | Substituted methylene steroids and their preparation |
| US3705179A (en) * | 1971-03-15 | 1972-12-05 | American Home Prod | Antiandrogenic steroids |
| US4239681A (en) * | 1974-04-15 | 1980-12-16 | Richardson-Merrell Inc. | Androst-4-en-19-ols |
| US4139617A (en) * | 1974-05-13 | 1979-02-13 | Richardson-Merrell Inc. | 19-Oxygenated-androst-5-enes for the enhancement of libido |
| GB1527161A (en) * | 1976-02-19 | 1978-10-04 | Leo A | Enol esters of steroids |
| DE2645104C2 (de) * | 1976-10-04 | 1986-04-24 | Schering AG, 1000 Berlin und 4709 Bergkamen | 11β-Hydroxy-1,4,8-pregnatrien-3,20-dion-Derivate und Verfahren zu ihrer Herstellung |
| US4278668A (en) * | 1977-11-25 | 1981-07-14 | Nicolas Gueritee | Pure 17 alpha-ethynyl(5 alpha), androst-2-ene,17 beta-cl, process for its preparation and therapeutical applications of the same |
| US4265815A (en) * | 1980-03-31 | 1981-05-05 | E. R. Squibb & Sons, Inc. | 17-(Substituted thio)androst-4-ene[16,17,-b]-[1,4]benzodioxin-3-ones |
-
1983
- 1983-07-26 US US06/517,457 patent/US4512986A/en not_active Expired - Lifetime
-
1984
- 1984-07-26 WO PCT/US1984/001173 patent/WO1985000609A1/en active IP Right Grant
- 1984-07-26 EP EP84903014A patent/EP0152429B1/en not_active Expired
- 1984-07-26 DE DE8484903014T patent/DE3480094D1/de not_active Expired
- 1984-07-26 JP JP59502899A patent/JPS60502100A/ja active Granted
- 1984-07-26 AU AU31582/84A patent/AU583476B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0152429A1 (en) | 1985-08-28 |
| EP0152429B1 (en) | 1989-10-11 |
| AU3158284A (en) | 1985-03-04 |
| DE3480094D1 (en) | 1989-11-16 |
| US4512986A (en) | 1985-04-23 |
| AU583476B2 (en) | 1989-05-04 |
| EP0152429A4 (en) | 1985-12-05 |
| WO1985000609A1 (en) | 1985-02-14 |
| JPS60502100A (ja) | 1985-12-05 |
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