DD143077A5 - Verfahren zur herstellung von 1,3-dibenzoesaeureestern des 17alpha-ethinyl-7alpha-methyl-1,3,5(10)-oestratrien-1,3,17beta-triols - Google Patents
Verfahren zur herstellung von 1,3-dibenzoesaeureestern des 17alpha-ethinyl-7alpha-methyl-1,3,5(10)-oestratrien-1,3,17beta-triols Download PDFInfo
- Publication number
- DD143077A5 DD143077A5 DD79212298A DD21229879A DD143077A5 DD 143077 A5 DD143077 A5 DD 143077A5 DD 79212298 A DD79212298 A DD 79212298A DD 21229879 A DD21229879 A DD 21229879A DD 143077 A5 DD143077 A5 DD 143077A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methyl
- preparation
- ethinyl
- estratrien
- ethynyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 9
- 150000002148 esters Chemical class 0.000 abstract description 9
- 230000001076 estrogenic effect Effects 0.000 abstract description 2
- -1 diacetic acid ester Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 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 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000262 estrogen Substances 0.000 description 4
- 229940011871 estrogen Drugs 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002674 ointment Substances 0.000 description 3
- 239000000583 progesterone congener Substances 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 description 1
- INJBMNNLSBCVGV-QDWSJHPCSA-N (8r,9r,10s,13r)-13-methyl-2,4,5,6,7,8,9,10,11,12-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C([C@@H]12)CC(=O)CC1CC[C@@H]1[C@@H]2CC[C@@]2(C)C1=CC=C2 INJBMNNLSBCVGV-QDWSJHPCSA-N 0.000 description 1
- MUENRDYXOADTOC-UHFFFAOYSA-N 13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol Chemical compound C1=CC=C2C3CCC(C)(C(CC4)O)C4C3CCC2=C1 MUENRDYXOADTOC-UHFFFAOYSA-N 0.000 description 1
- MUENRDYXOADTOC-ZBRFXRBCSA-N 3-Deoxyestradiol Chemical compound C1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUENRDYXOADTOC-ZBRFXRBCSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class 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 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000112 cooling gas Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002357 endometrial effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 229960004400 levonorgestrel Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic 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
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782818164 DE2818164A1 (de) | 1978-04-21 | 1978-04-21 | 1,3-dibenzoesaeureester des 17alpha- ethinyl-7 alpha -methyl-1,3,5(10)-oestratrien- 1,3,17 beta -triols, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD143077A5 true DD143077A5 (de) | 1980-07-30 |
Family
ID=6037985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79212298A DD143077A5 (de) | 1978-04-21 | 1979-04-18 | Verfahren zur herstellung von 1,3-dibenzoesaeureestern des 17alpha-ethinyl-7alpha-methyl-1,3,5(10)-oestratrien-1,3,17beta-triols |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4259325A (cs) |
| EP (1) | EP0004898B1 (cs) |
| JP (1) | JPS54141756A (cs) |
| AT (1) | AT366065B (cs) |
| AU (1) | AU521011B2 (cs) |
| CA (1) | CA1123426A (cs) |
| CS (1) | CS203036B2 (cs) |
| DD (1) | DD143077A5 (cs) |
| DE (2) | DE2818164A1 (cs) |
| DK (1) | DK153279A (cs) |
| ES (1) | ES479691A1 (cs) |
| GR (1) | GR73572B (cs) |
| HU (1) | HU179069B (cs) |
| IE (1) | IE48133B1 (cs) |
| IL (1) | IL57072A (cs) |
| SU (1) | SU843757A3 (cs) |
| YU (1) | YU78679A (cs) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3022337A1 (de) * | 1980-06-11 | 1982-01-07 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Praeparate zur kontrazeption und zur behandlung gynaekologischer stoerungen |
| US4757062A (en) * | 1985-11-01 | 1988-07-12 | E. I. Du Pont De Nemours And Company | Substituted benzoate ester prodrugs of estrogens |
| US5188835A (en) * | 1986-06-16 | 1993-02-23 | Kabi Pharmacia Ab | Intravaginal devices |
| WO1996015794A1 (en) | 1994-11-22 | 1996-05-30 | Balance Pharmaceuticals, Inc. | Compositions and methods for contraception and for treatment of benign gynecological disorders |
| US7989436B2 (en) | 2003-07-23 | 2011-08-02 | Duramed Pharmaceuticals, Inc. | Estrogenic compounds and pharmaceutical formulations comprising the same |
| US7459445B2 (en) * | 2000-03-10 | 2008-12-02 | Duramed Pharmaceuticals, Inc. | Estrogenic compounds and topical pharmaceutical formulations of the same |
| US6855703B1 (en) | 2000-03-10 | 2005-02-15 | Endeavor Pharmaceuticals | Pharmaceutical compositions of conjugated estrogens and methods of analyzing mixtures containing estrogenic compounds |
| US6660726B2 (en) | 2000-03-10 | 2003-12-09 | Endeavor Pharmaceuticals | Estrogenic compounds, pharmaceutical compositions thereof, and methods of using same |
| US6992075B2 (en) * | 2003-04-04 | 2006-01-31 | Barr Laboratories, Inc. | C(14) estrogenic compounds |
| WO2004091535A2 (en) * | 2003-04-11 | 2004-10-28 | Barr Laboratories, Inc. | Methods of administering estrogens and progestins |
| EP1853272A1 (en) * | 2005-02-03 | 2007-11-14 | Duramed Pharmaceuticals, Inc. | Compositions of unconjugated estrogens and methods for their use |
| JP5357108B2 (ja) * | 2010-06-29 | 2013-12-04 | 大陽日酸株式会社 | バーナの燃焼方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2861086A (en) * | 1957-12-27 | 1958-11-18 | Searle & Co | 17-oxygenated estra-1, 3, 5(10)-triene-1, 3-diols, and the corresponding esters and ethers |
| US3024256A (en) * | 1961-02-20 | 1962-03-06 | Searle & Co | 16-substituted 1, 3-diacyloxyestra-1, 3, 5(10)-trien-17-ones |
| DE1240859B (de) * | 1963-11-09 | 1967-05-24 | Schering Ag | Verfahren zur Herstellung von Androstan-1alpha, 3alpha, 17beta-triol und seinen Estern |
| FR1580268A (cs) * | 1968-06-10 | 1969-09-05 | ||
| US3574197A (en) * | 1968-07-09 | 1971-04-06 | Schering Ag | Process of producing 1-hydroxy-7alpha-methyl-estradiol derivatives |
| US3951959A (en) * | 1973-07-13 | 1976-04-20 | Schering Aktiengesellschaft | 1,3-Oxygenated 8α-estratrienes |
-
1978
- 1978-04-21 DE DE19782818164 patent/DE2818164A1/de not_active Withdrawn
-
1979
- 1979-03-31 EP EP79101000A patent/EP0004898B1/de not_active Expired
- 1979-03-31 DE DE7979101000T patent/DE2962423D1/de not_active Expired
- 1979-04-03 YU YU00786/79A patent/YU78679A/xx unknown
- 1979-04-06 CS CS792363A patent/CS203036B2/cs unknown
- 1979-04-06 SU SU792745050A patent/SU843757A3/ru active
- 1979-04-07 GR GR58834A patent/GR73572B/el unknown
- 1979-04-10 US US06/028,744 patent/US4259325A/en not_active Expired - Lifetime
- 1979-04-11 DK DK153279A patent/DK153279A/da not_active IP Right Cessation
- 1979-04-15 IL IL57072A patent/IL57072A/xx unknown
- 1979-04-18 DD DD79212298A patent/DD143077A5/de unknown
- 1979-04-18 ES ES479691A patent/ES479691A1/es not_active Expired
- 1979-04-19 AT AT0296079A patent/AT366065B/de not_active IP Right Cessation
- 1979-04-20 HU HU79SCHE676A patent/HU179069B/hu unknown
- 1979-04-20 JP JP4811179A patent/JPS54141756A/ja active Pending
- 1979-04-20 CA CA325,941A patent/CA1123426A/en not_active Expired
- 1979-04-23 AU AU46276/79A patent/AU521011B2/en not_active Ceased
- 1979-08-08 IE IE821/79A patent/IE48133B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATA296079A (de) | 1981-07-15 |
| IE48133B1 (en) | 1984-10-03 |
| IL57072A (en) | 1982-07-30 |
| ES479691A1 (es) | 1979-08-01 |
| SU843757A3 (ru) | 1981-06-30 |
| CS203036B2 (en) | 1981-02-27 |
| US4259325A (en) | 1981-03-31 |
| AT366065B (de) | 1982-03-10 |
| EP0004898A1 (de) | 1979-10-31 |
| IL57072A0 (en) | 1979-07-25 |
| YU78679A (en) | 1983-02-28 |
| JPS54141756A (en) | 1979-11-05 |
| CA1123426A (en) | 1982-05-11 |
| HU179069B (en) | 1982-08-28 |
| AU521011B2 (en) | 1982-03-11 |
| AU4627679A (en) | 1979-10-25 |
| DE2962423D1 (en) | 1982-05-19 |
| EP0004898B1 (de) | 1982-04-07 |
| IE790821L (en) | 1979-10-21 |
| DK153279A (da) | 1979-10-22 |
| DE2818164A1 (de) | 1979-10-31 |
| GR73572B (cs) | 1984-03-19 |
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