PL75312B2 - 17alpha-ehtynylestriols[au3982772a] - Google Patents
17alpha-ehtynylestriols[au3982772a] Download PDFInfo
- Publication number
- PL75312B2 PL75312B2 PL15422772A PL15422772A PL75312B2 PL 75312 B2 PL75312 B2 PL 75312B2 PL 15422772 A PL15422772 A PL 15422772A PL 15422772 A PL15422772 A PL 15422772A PL 75312 B2 PL75312 B2 PL 75312B2
- Authority
- PL
- Poland
- Prior art keywords
- ethynyl
- estriol
- ether
- formula
- cycloalkyl
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 15
- BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 4
- -1 alkali metal alkoxide Chemical class 0.000 claims abstract 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- 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 claims description 11
- 229960005309 estradiol Drugs 0.000 claims description 11
- 229930182833 estradiol Natural products 0.000 claims description 10
- 210000004291 uterus Anatomy 0.000 claims description 9
- 210000001215 vagina Anatomy 0.000 claims description 8
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 210000000805 cytoplasm Anatomy 0.000 claims description 4
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000005259 measurement Methods 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000003760 tallow Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 230000001076 estrogenic effect Effects 0.000 abstract description 3
- DZFYOYRNBGNPJW-UHFFFAOYSA-N ethoxythallium Chemical compound [Tl+].CC[O-] DZFYOYRNBGNPJW-UHFFFAOYSA-N 0.000 abstract description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 abstract 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 229960003399 estrone Drugs 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229940011871 estrogen Drugs 0.000 description 9
- 239000000262 estrogen Substances 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VSODIPLKPBLGCC-NADOGSGZSA-N (8r,9s,13s,14s,16r,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,16,17-triol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@]([C@H](O)C4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VSODIPLKPBLGCC-NADOGSGZSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- ODYKCPYPRCJXLY-PZORDLPLSA-N quinestradol Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1C[C@@H](O)[C@@H]4O)C)CC2=CC=3OC1CCCC1 ODYKCPYPRCJXLY-PZORDLPLSA-N 0.000 description 4
- 229960004726 quinestradol Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WPOCIZJTELRQMF-QFXBJFAPSA-N 16alpha-hydroxyestrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C([C@H](O)C4)=O)[C@@H]4[C@@H]3CCC2=C1 WPOCIZJTELRQMF-QFXBJFAPSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000001086 cytosolic effect Effects 0.000 description 3
- 229960001348 estriol Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000009245 menopause Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007788 liquid Substances 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
- LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- PWZUUYSISTUNDW-VAFBSOEGSA-N quinestrol Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@]4(O)C#C)C)CC2=CC=3OC1CCCC1 PWZUUYSISTUNDW-VAFBSOEGSA-N 0.000 description 2
- 229960001424 quinestrol Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 description 1
- WPOCIZJTELRQMF-UHFFFAOYSA-N 16alpha-Hydroxyestrone Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)=O)C4C3CCC2=C1 WPOCIZJTELRQMF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241001640117 Callaeum Species 0.000 description 1
- 101000841393 Candida albicans Probable NADPH dehydrogenase Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108010085330 Estradiol Receptors Proteins 0.000 description 1
- 102100038595 Estrogen receptor Human genes 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- OCDXZFSOHJRGIL-UHFFFAOYSA-N cyclohexyloxycyclohexane Chemical compound C1CCCCC1OC1CCCCC1 OCDXZFSOHJRGIL-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 229960003398 hydroxyestrone diacetate Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12769071A | 1971-03-24 | 1971-03-24 | |
| US127771A US3697558A (en) | 1971-03-24 | Preparation of 17alpha-ethynylestriol | |
| US00134420A US3813419A (en) | 1971-03-24 | 1971-04-15 | Preparation of phenolic ethers |
| US13667171A | 1971-04-23 | 1971-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL75312B2 true PL75312B2 (en) | 1974-12-31 |
Family
ID=27494695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL15422772A PL75312B2 (en) | 1971-03-24 | 1972-03-22 | 17alpha-ehtynylestriols[au3982772a] |
Country Status (14)
| Country | Link |
|---|---|
| AU (1) | AU461293B2 (OSRAM) |
| BE (1) | BE781099A (OSRAM) |
| CA (1) | CA973871A (OSRAM) |
| CS (1) | CS173592B2 (OSRAM) |
| DD (1) | DD95567A5 (OSRAM) |
| DE (1) | DE2213482A1 (OSRAM) |
| FR (1) | FR2130683B1 (OSRAM) |
| GB (1) | GB1336703A (OSRAM) |
| IE (1) | IE36944B1 (OSRAM) |
| IL (1) | IL38952A (OSRAM) |
| NL (1) | NL7204019A (OSRAM) |
| PL (1) | PL75312B2 (OSRAM) |
| SE (1) | SE378427B (OSRAM) |
| ZA (1) | ZA721523B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109721634B (zh) * | 2019-01-24 | 2021-08-03 | 上海新华联制药有限公司 | 一种尼尔雌醇的合成工艺 |
| CN109705182B (zh) * | 2019-01-24 | 2021-08-31 | 上海新华联制药有限公司 | 一种尼尔雌醇的制备方法 |
-
1972
- 1972-03-07 ZA ZA721523A patent/ZA721523B/xx unknown
- 1972-03-08 IE IE295/72A patent/IE36944B1/xx unknown
- 1972-03-09 AU AU39827/72A patent/AU461293B2/en not_active Expired
- 1972-03-10 IL IL38952A patent/IL38952A/en unknown
- 1972-03-15 CA CA137,140A patent/CA973871A/en not_active Expired
- 1972-03-20 DE DE19722213482 patent/DE2213482A1/de active Pending
- 1972-03-21 SE SE7203607A patent/SE378427B/xx unknown
- 1972-03-22 PL PL15422772A patent/PL75312B2/pl unknown
- 1972-03-23 GB GB1352372A patent/GB1336703A/en not_active Expired
- 1972-03-23 BE BE781099A patent/BE781099A/xx unknown
- 1972-03-24 FR FR7210470A patent/FR2130683B1/fr not_active Expired
- 1972-03-24 NL NL7204019A patent/NL7204019A/xx unknown
- 1972-03-24 DD DD161848A patent/DD95567A5/xx unknown
- 1972-03-24 CS CS1983A patent/CS173592B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2213482A1 (de) | 1972-09-28 |
| IL38952A (en) | 1976-04-30 |
| CS173592B2 (OSRAM) | 1977-02-28 |
| NL7204019A (OSRAM) | 1972-09-26 |
| FR2130683A1 (OSRAM) | 1972-11-03 |
| IL38952A0 (en) | 1972-05-30 |
| AU3982772A (en) | 1973-09-13 |
| GB1336703A (en) | 1973-11-07 |
| IE36944L (en) | 1972-09-25 |
| SE378427B (OSRAM) | 1975-09-01 |
| DD95567A5 (OSRAM) | 1973-02-12 |
| IE36944B1 (en) | 1977-03-30 |
| FR2130683B1 (OSRAM) | 1976-04-16 |
| ZA721523B (en) | 1973-10-31 |
| AU461293B2 (en) | 1975-05-22 |
| BE781099A (fr) | 1972-09-25 |
| CA973871A (en) | 1975-09-02 |
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