DE2801417C2 - - Google Patents
Info
- Publication number
- DE2801417C2 DE2801417C2 DE2801417A DE2801417A DE2801417C2 DE 2801417 C2 DE2801417 C2 DE 2801417C2 DE 2801417 A DE2801417 A DE 2801417A DE 2801417 A DE2801417 A DE 2801417A DE 2801417 C2 DE2801417 C2 DE 2801417C2
- Authority
- DE
- Germany
- Prior art keywords
- product
- vinyl
- general formula
- compounds
- preparation
- 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 - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 238000007127 saponification reaction Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000796 flavoring agent Substances 0.000 claims description 5
- 235000013355 food flavoring agent Nutrition 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 239000000047 product Substances 0.000 description 25
- 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 13
- 229930182833 estradiol Natural products 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 229960005309 estradiol Drugs 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 10
- 150000001241 acetals Chemical class 0.000 description 10
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229910052722 tritium Inorganic materials 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 230000001076 estrogenic effect Effects 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
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 3
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 210000004291 uterus Anatomy 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 210000000172 cytosol Anatomy 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- VCPPTNDHEILJHD-UHFFFAOYSA-N lithium;prop-1-ene Chemical compound [Li+].[CH2-]C=C VCPPTNDHEILJHD-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000009245 menopause Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000019255 Menstrual disease Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010033557 Palpitations Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- -1 acetyl halide Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- UWCHSDIUMBNDLT-UHFFFAOYSA-L copper;methylsulfanylmethane;dibromide Chemical compound CSC.Br[Cu]Br UWCHSDIUMBNDLT-UHFFFAOYSA-L 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002159 estradiols Chemical class 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 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
- 239000012530 fluid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
- WMWSRIHFAVOHSW-UHFFFAOYSA-N lithium;ethane-1,2-diamine;ethyne Chemical compound [Li+].[C-]#C.NCCN WMWSRIHFAVOHSW-UHFFFAOYSA-N 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 208000035824 paresthesia Diseases 0.000 description 1
- 238000004634 pharmacological analysis method Methods 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical group [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 230000001836 utereotrophic effect Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7700859A FR2377419A1 (fr) | 1977-01-13 | 1977-01-13 | Nouveaux derives steroides 11b-substitues 1,3,5 (10) trieniques, leur procede de preparation et leur application comme medicament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2801417A1 DE2801417A1 (de) | 1978-07-20 |
| DE2801417C2 true DE2801417C2 (en:Method) | 1992-09-17 |
Family
ID=9185438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782801417 Granted DE2801417A1 (de) | 1977-01-13 | 1978-01-13 | Neue 11beta-substituierte 1,3,5(10)- trienische steroidderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4272530A (en:Method) |
| JP (1) | JPS5390254A (en:Method) |
| BE (1) | BE862870A (en:Method) |
| CA (1) | CA1121339A (en:Method) |
| CH (1) | CH630646A5 (en:Method) |
| DE (1) | DE2801417A1 (en:Method) |
| DK (1) | DK161334C (en:Method) |
| FR (1) | FR2377419A1 (en:Method) |
| GB (1) | GB1595133A (en:Method) |
| HU (1) | HU176154B (en:Method) |
| IE (1) | IE46302B1 (en:Method) |
| LU (1) | LU78859A1 (en:Method) |
| NL (1) | NL7800364A (en:Method) |
| SE (1) | SE435516B (en:Method) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7701384A (nl) * | 1977-02-10 | 1978-08-14 | Akzo Nv | Werkwijze voor het bereiden van nieuwe steroiden van de oestraanreeks. |
| FR2528434B1 (fr) * | 1982-06-11 | 1985-07-19 | Roussel Uclaf | Nouveaux 19-nor steroides substitues en 11b et eventuellement en 2, leur procede de preparation et leur application comme medicament |
| FR2522328B1 (fr) * | 1982-03-01 | 1986-02-14 | Roussel Uclaf | Nouveaux produits derives de la structure 3-ceto 4,9 19-nor steroides, leur procede de preparation et leur application comme medicaments |
| FR2640977A2 (en) * | 1982-06-11 | 1990-06-29 | Roussel Uclaf | New position-11 substituted 19-norsteroids and their application as medicinal products. |
| DE3625315A1 (de) * | 1986-07-25 | 1988-01-28 | Schering Ag | 11ss-(4-isopropenylphenyl)-estra-4,9-diene, deren herstellung und diese enthaltende pharmazeutische praeparate |
| DE3925179C2 (de) * | 1988-08-22 | 1996-07-18 | Volkswagen Ag | Ansaugluftsteuersystem zum Betreiben einer Brennkraftmaschine mit Leerlaufdrehzahlregelung |
| DE4018168A1 (de) * | 1990-06-01 | 1991-12-05 | Schering Ag | Ausgangsverbindungen fuer die herstellung von 10ss-h-steroiden und ein verfahren zur herstellung dieser ausgangsverbindungen |
| DE4132182A1 (de) * | 1991-09-24 | 1993-03-25 | Schering Ag | 11(beta)-substituierte 14, 17-ethanoestratriene, verfahren zur herstellung dieser verbindungen, sowie ihre verwendung zur herstellung von arzneimitteln |
| US5427766A (en) * | 1993-11-15 | 1995-06-27 | The Dow Chemical Company | Radiolabeled steroids for use in radiochemical-guided surgery |
| CN1220696C (zh) | 2000-07-28 | 2005-09-28 | 阿克佐诺贝尔公司 | 16α－甲基或乙基取代的雌激素 |
| FR2826004B1 (fr) | 2001-06-13 | 2008-03-28 | Aventis Pharma Sa | Procede de preparation de derives estrogenes |
| CN100431545C (zh) * | 2003-05-22 | 2008-11-12 | 潘塔希生物科学股份有限公司 | 雌激素成分在制备用于治疗及预防肌与骨疼痛中的组合物中的应用 |
| UA89964C2 (ru) | 2004-09-08 | 2010-03-25 | Н.В. Органон | 15β-ЗАМЕЩЕННЫЕ СТЕРОИДЫ, КОТОРЫЕ ИМЕЮТ СЕЛЕКТИВНУЮ ЭСТРОГЕННУЮ АКТИВНОСТЬ |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337365A (en) * | 1963-03-25 | 1967-08-22 | Ibm | Electrical resistance composition and method of using the same to form a resistor |
| US3299108A (en) * | 1965-10-18 | 1967-01-17 | Searle & Co | 17alpha-alkynyl/alkenyl-13beta-alkyl-11-alkylgona-1, 3, 5 (10)-triene-3, 17beta-diols, ethers and esters thereof and intermediates thereto |
| US3346602A (en) * | 1966-10-12 | 1967-10-10 | Searle & Co | 13beta-alkyl-11-alkylgona-1, 3, 5 (10)-trien-17-ones, ethers and esters thereof |
| US3465010A (en) * | 1966-11-22 | 1969-09-02 | Searle & Co | 17 - (unsaturated hydrocarbon - substituted) 11,13beta - dialkylgon -4 - ene - 3,17beta-diols and esters thereof |
| US3629304A (en) * | 1969-06-16 | 1971-12-21 | Searle & Co | 17alpha-alkynyl - 11beta 13beta - dialkylgona-1 3 5 (10)-triene - 3 17beta-diol 3-cycloalkyl ethers compositions and method |
| GB1255345A (en) * | 1969-08-15 | 1971-12-01 | Searle & Co | 3-(3-OXO-11beta13beta-DIALKYL-17beta-HYDROXYGON-4-EN-17alpha-YL) PROPIONIC ACID gamma-LACTONE |
| US3755301A (en) * | 1972-06-23 | 1973-08-28 | Searle & Co | Manufacture of 11-alkyl steroids |
| US3927046A (en) * | 1972-12-09 | 1975-12-16 | Akzona Inc | Novel 11,11-alkylidene steroids |
| FR2235949B1 (en:Method) * | 1973-06-18 | 1978-03-17 | Roussel Uclaf | |
| NL7317358A (nl) * | 1973-12-19 | 1975-06-23 | Akzo Nv | Nieuwe 11(beta)-alkylsteroiden van de oestraanreeks. |
-
1977
- 1977-01-13 FR FR7700859A patent/FR2377419A1/fr active Granted
- 1977-12-21 SE SE7714614A patent/SE435516B/sv not_active IP Right Cessation
-
1978
- 1978-01-06 US US05/867,486 patent/US4272530A/en not_active Expired - Lifetime
- 1978-01-12 DK DK013978A patent/DK161334C/da not_active IP Right Cessation
- 1978-01-12 CA CA000294815A patent/CA1121339A/fr not_active Expired
- 1978-01-12 NL NL7800364A patent/NL7800364A/xx not_active Application Discontinuation
- 1978-01-12 BE BE184285A patent/BE862870A/xx not_active IP Right Cessation
- 1978-01-12 HU HU78RO955A patent/HU176154B/hu unknown
- 1978-01-12 LU LU78859A patent/LU78859A1/xx unknown
- 1978-01-13 GB GB1377/78A patent/GB1595133A/en not_active Expired
- 1978-01-13 JP JP206778A patent/JPS5390254A/ja active Granted
- 1978-01-13 DE DE19782801417 patent/DE2801417A1/de active Granted
- 1978-01-13 CH CH39178A patent/CH630646A5/fr not_active IP Right Cessation
- 1978-01-13 IE IE79/78A patent/IE46302B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5390254A (en) | 1978-08-08 |
| JPS6257638B2 (en:Method) | 1987-12-02 |
| FR2377419B1 (en:Method) | 1979-04-20 |
| DK161334B (da) | 1991-06-24 |
| SE7714614L (sv) | 1978-07-14 |
| HU176154B (en) | 1980-12-28 |
| CH630646A5 (fr) | 1982-06-30 |
| GB1595133A (en) | 1981-08-05 |
| LU78859A1 (fr) | 1978-09-18 |
| DK13978A (da) | 1978-07-14 |
| DK161334C (da) | 1991-12-09 |
| IE46302B1 (en) | 1983-04-20 |
| CA1121339A (fr) | 1982-04-06 |
| FR2377419A1 (fr) | 1978-08-11 |
| NL7800364A (nl) | 1978-07-17 |
| BE862870A (fr) | 1978-07-12 |
| SE435516B (sv) | 1984-10-01 |
| IE780079L (en) | 1978-07-13 |
| DE2801417A1 (de) | 1978-07-20 |
| US4272530A (en) | 1981-06-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2858797C2 (en:Method) | ||
| DE2801417C2 (en:Method) | ||
| EP0648779B1 (de) | Neue 11-Benzaldoxim-17beta methoxy-17alpha-methoxymethyl-estradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE69910068T2 (de) | 17beta-acyl-17alpha-propynyl-11beta-arylsteroide und ihre derivate mit agonistischen oder antagonistischen hormonalen aktivitäten | |
| DE69013815T2 (de) | Omega-Phenylaminoalkansäuren, die durch ein 19-nor-Steroidrest am Phenylrest substituiert sind, ihre Salze, ein Verfahren zu ihrer Herstellung, sowie Zwischenprodukte dieses Verfahrens, ihre Verwendung als Arzneimittel und pharmazeutische Präparate davon. | |
| DE1801750A1 (de) | Von Prostaglandinen abgeleitete Verbindungen und Verfahren zu ihrer Herstellung | |
| DE10236405A1 (de) | Progesteronrezeptormodulatoren mit erhöhter antigonadotroper Aktivität für die weibliche Fertilitätskontrolle und Hormonersatztherapie | |
| DE2147391C3 (de) | Verfahren zur Herstellung von 13- Äthyl-17 a -äthinyl-17 ß -hydroxy- 16 a -methylgona^-en-S-on | |
| DE2748250C2 (en:Method) | ||
| DE1493042B2 (de) | 17 Tetrahydropyranylather und 3,17 Bis (tetrahydropyranyl)-ather von Östradiol und Ostradioldenvaten, Ver fahren zu deren Herstellung und diese enthaltende Heilmittel | |
| DE1810343A1 (de) | Neue Adamantylidenverbindungen | |
| DE1961433B2 (de) | 8 Alkoxy 4 hydroxy 3 methyl 10 methylen 2,9 dioxatncyclo (4,3,1,0 hoch 3,hoch 7) decane und 8 Alkoxy 4 hydroxy 3,10 dimethyl 2,9 dioxatncyclo (4,3,1,0 hoch 3,hoch 7) decane sowie Verfahren zu ihrer Herstellung | |
| AT269547B (de) | Verfahren zur Herstellung eines konzeptionsverhindernden Mittels für warmblütige Tiere | |
| DE2109305C3 (de) | 20-Hydroxylierte 17 a - Methyl-19-nor-pregna-4,9diene, Verfahren zu deren Herstellung sowie Zwischenprodukte | |
| DE60004007T2 (de) | Ein Verfahren zur Isolierung 2-Deoxyecdysteron aus Zoanthus sp und ihre Verwendung zur Herstellung eines Medikaments zur Geburtseinleitung oder zum Schwangerschaftsabbruch | |
| DE2741771A1 (de) | Neue 2,2-dimethyl-19-nor-steroide, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen | |
| DE1808425C (de) | 3 Oxo 17beta hydroxy 17 alpha (but 2 myl> 13 beta C tief 1 bis C tief 3 alkyl gona 4,9,11 tnene | |
| DE4216003A1 (de) | Dissoziierte kompetitive Progesteronantagonisten | |
| DE1235315B (de) | Verfahren zur Herstellung von 3, 11beta, 17beta-Trihydroxy-17alpha-aethinyl-delta 1,3,5(10)-oestratrien bzw. von 3-Estern oder 3-AEthern desselben | |
| AT251772B (de) | Verfahren zur Herstellung eines neuen Äthinylderivates des 8-iso-Östrons | |
| DE2213482A1 (de) | 17alpha-Äthinylöstriol verbindungen und ihre Herstellung | |
| AT329778B (de) | Verfahren zur herstellung von neuen 17alfa-athinylostriolderivaten | |
| AT240540B (de) | Verfahren zur Herstellung von 4-Chlor-Δ<4>-3-ketosteroidverbindungen | |
| DE1445626A1 (de) | Verfahren zur Gewinnung von Alkaloiden | |
| DE2348197A1 (de) | Noraethindron-o-alkyloxime |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
|
| 8172 | Supplementary division/partition in: |
Ref country code: DE Ref document number: 2858798 Format of ref document f/p: P |
|
| Q171 | Divided out to: |
Ref country code: DE Ref document number: 2858798 |
|
| 8125 | Change of the main classification |
Ipc: A61K 31/19 |
|
| D2 | Grant after examination | ||
| 8380 | Miscellaneous part iii |
Free format text: SEITE 5, ZEILE 49 "ALKYLREST" AENDERN IN "ALLYLREST" |
|
| 8325 | Change of the main classification |
Ipc: C07J 1/00 |
|
| 8380 | Miscellaneous part iii |
Free format text: DIE NEBENKLASSEN LAUTEN RICHTIG: "C07J 17/00 C07J 33/00 A61K 31/575" |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |