IE853169L - Gonanes - Google Patents
GonanesInfo
- Publication number
- IE853169L IE853169L IE853169A IE316985A IE853169L IE 853169 L IE853169 L IE 853169L IE 853169 A IE853169 A IE 853169A IE 316985 A IE316985 A IE 316985A IE 853169 L IE853169 L IE 853169L
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- examples
- hereinbefore described
- general formula
- gonadiene
- Prior art date
Links
- 150000003804 gonanes Chemical class 0.000 title claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- -1 isobutyryl Chemical group 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NOKLXIJSQZUICI-SJXULMIUSA-N OCCCC1C[C@H]2CCC=3[C@@H](CCC4=CC(CCC=34)=O)[C@@H]2C1 Chemical compound OCCCC1C[C@H]2CCC=3[C@@H](CCC4=CC(CCC=34)=O)[C@@H]2C1 NOKLXIJSQZUICI-SJXULMIUSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003418 antiprogestin Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000003152 gestagenic effect Effects 0.000 description 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 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
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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
1. 13 alpha-alkylgonanes of general formula I see diagramm : EP0186834,P6,F4 wherein R represents an acyl radical having up to 10 C atoms and X represents an oxygen atom or the grouping N apprch OH.
Description
58147 - i - I R E L A N D PATENTS ACT, 19 64 ■. i Ife A: A zib &» COMPLETE SPECIFICATION "13a-alky1-173-(3-acyloxypropyl)-gonanes" WPUCATWw Ko wrcmouMQt, snjss ItrlStt Patent Application by SCHERING AKTIENGESELLSCHAFT, a Germany Company of Berlin and Bergkamen, Federal Republic of Germany. 8147 - 2 - The invention relates to new 13o(-alkyl-178-(3-acyloxy-propyl)-gonanes, a process for their manufacture and pharmaceutical preparations containing these compounds. 130C-alkyl-17B- (3-hydroxypropyl)-4,9-gonadiene-3-ones are 5 known from; European Patent Application No. 84730062.1.
These compounds have a strong affinity for gestagen receptors, without themselves having any gestagenic activity. They are competitive antagonists of progesterone (antigestagens) and are suitable for inducing abortions since they displace 10 the progesterore necessary for maintenance of pregnancy from the receptor. The compounds are thus valuable and of interest from the point of view of their use for postcoital (p.c.) control of fertility.
It has now been found that their bio-availability can,sur-15 prisingly, be considerably enhanced by converting these compounds into the 13S-alkyl-178-(3-acyloxypropyl)-gonanes' of general formula I. In comparison to the previously known 13 They can be stored without difficulty for a long period of time at room temperature without decomposing. - 3 - According to one aspect the invention provides a compound of the general formula I where 5 R represents an acyl radical having up to 10 C-atoms and X represents an oxygen atom or the grouping IWOH.
The acyl radical R may contain up to 10 C-atoms. Possible acyl radicals are, for example, the formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 10 glycoloyl, cyclopentylacetyl, mono-, di-, trichcloroacetyl, benzoyl, trifluoromethylbenzoyl and nicotinovl radicals; preferred are the acetyl and benzoyl radicals.
X represents an oxygen atom or the group N*^0H, with the hydroxyimino radical being in the syn or anti position. ch hh (I) 15 In another aspect the invention provides a method of - 4 - preparing a compound of general formula I wherein a compound of the general formula II ch2 - ch2 - ch2-oh (ii) is reacted with an acid chloride or an acid anhydride of 5 general formula III or IV respectively 0 II R-C-Cl (III) 0 II (R-C)20 (IV) where R represents an acyl radical having up to 10 C-atoms, in the 10 presence of bases at a temperature of between 0 and 60°C and, if desired subsequently reacting with hydroxylamine hydrochloride in the presence of tertiary amines at a temperature of between -20 and 4o°C. The preferred bases for esterification are tertiary amines such as 15 pyridine. The preferred tertiary amine - 5 - during conversion for the preparation of oximes is pyridine.
Further suitable tertiary bases are, for example, tri-methylamine, triethylamine, N,N-dimethylamino pyridine, 5 1,5-diazabicyclo [4.3.ojnonene-5 (DBN) and 1.5-diazabicyclo-[5.4.6] undecene-5 (DBU).
The 13a-alkylgonanes of general formula I can be used in the form of pharmaceutical preparations. The preparations are manufactured by the methods generally known in galenics 10 by mixing with organic or inorganic inert carrier material suitable for enteral, percutaneous or parenteral application .
For humans the dosage of the active ingredients in accordance with the invention amounts to approximately 10 to 15 1000 mg per day.
The invention will be more clearly understood from the following examples which, however, are given without limitation to the scope of the invention. - 6 Example 1 A solution of 2.4 g of 11 B-(4-dimethylaminophenyl)-1 7o(- hydroxy-1 3o(-methyl-1 7B (3-hydroxypropyl)-4, 9-gonadiene- 3-one in 7 ml of pyridine and 14 ml of acetanhydride is 5 stirred for 14 hours at 25 °C. This mixture is then poured into warm water (100 ml) at a temperature of approx. 50 °C, stirred for 15 minutes and the cooled emulsion extracted with methylene chloride. The methylene chloride phase is washed neutral with NaHCO, solution, dried over Na-SO. 3 2 4 10 and concentrated. Crystallization of the crude product from ethylacetate/diisopropy 1 ether yields 2.24 g of 17B-(3-acetoxypropyl)-11B- (4-dimethylaminophenyl)-17 -hydroxy-130f-methyl-4 ,9-gonadiene-3-one with a melting point of 162 - 164 °C. 15 [a]^5 + 436.5° (CHCl3, c = 0.515).
Example 2 0.36 ml of benzoyl chloride in 4 ml of methylene chloride are dripped, ice-cooled, into a solution of 700 mg of 11B-(4-dimethylaminophenyl)-17«-hydroxy-1S^-methyl-l7B-(3-hy-20 droxypropyl)-4,9-gonadiene-3-one. The mixture is stirred for 60 minutes at +5 °C, then poured into saturated NaHCO^ solution and extracted with ethyl acetate. Crystallization of the crude product from hexane/diisopropyl ether yields 630 mg of 17B-(3-benzoyloxypropyl)-11B-(4-dimethylamino-25 phenyl)-1 7«-hydroxy-1 32(-inethyl-4 , 9-gonadiene-3-one with a melting point of 114 - 116 °C. - 7 - Example 3 A solution of 630 mg of 178-(3-acetoxypropyl)-116-(4-dimethylaminophenyl) -1 7oc-hydroxy-! 3
Claims (1)
1.CLAIMS 1. 13oC-alkylgonanes of general formula I CH ^ 3 CH N CH2~CH2~CH2"0R (I) 5 3. 10 5. where R represents an acyl radical having up to '10 C-atoms and X represents an oxygen atom or the grouping N OH. A compound as claimed in claim 1 wherein R is acetyl or benzoyl. 17 8-(3-acetoxypropyl)-118-(4-dimethylaminophenyl)-17a-hydroxy-13a-methyl-4,9-gonadiene-3-one. 178-(3-benzoyloxypropyl)-113-(4-dimethylaminophenyl)-17a-hydroxy-13a-methyl-4,9-gonadiene-3-one. 17 8-(3-acetoxypropyl)-118-(4-dimethylaminophenyl)-17cx-hydroxy-13a-methyl-4,9-gonadiene-3-one-anti-oxime. - 9 - 6. A process for the preparation of 13Of-alky 1 gonanes of general formula I where 5 R and X have the meaning given in Claim 1, charac terized in that a compound of the formula ii ch2-ch2-ch2-oh - 10 - is reacted with an acid chloride or an acid anhydride of general formula III or IV respectively 0 II R-C-Cl (III) (R-C)2O (IV) where R has the meaning given in Claim 1, in the presence of bases at a temperature of between 0 and 60°C and, if desired subsequently reacting with hydroxylamine hydrochloride in the presence of tertiary amines at a 10 temperature of between -20 and +40°C. 7. A pharmaceutical preparation comprising a compound as claimed in any of Claims 1 to 5 and a pharmaceutically acceptable carrier. 8. Use of compounds of Claims 1 to 5 for the manufacture of pharmaceuticals. 15 9. A method of medical treatment or prophylaxis comprising the step of administering an effective amount of a compound as claimed in any of Claims 1 to 5 or a composition as claimed in Claim 7. 10. The use of a compound as claimed in any of claims 1 to 9 20 for the manufacture of a pharmaceutical composition for use in a method of medical treatment or prophylaxis. 11. A compound substantially as hereinbefore described with reference to the Examples. - 11 - 12. A process substantially as hereinbefore described with reference to the Examples. 13. A pharmaceutical preparation substantially as hereinbefore described with reference to the Examples. 5 14. A method substantially as hereinbefore described with reference to the Examples. Dated this 16th day of December 1985 CRUICJS&HANK & CO., BV:/1 Executive Agferrt^ for the Applicant Youghal House, 13 Trinity Street, Dublin
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843446661 DE3446661A1 (en) | 1984-12-18 | 1984-12-18 | NEW 13 (ALPHA) -ALKYL-17 (BETA) - (3-ACYLOXYPROPYL) GONANA |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE853169L true IE853169L (en) | 1986-06-18 |
| IE58147B1 IE58147B1 (en) | 1993-07-14 |
Family
ID=6253403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE316985A IE58147B1 (en) | 1984-12-18 | 1985-12-16 | 13 alpha -alkyl-17 beta-(3acyloxypropyl)-gonanes |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0186834B1 (en) |
| JP (1) | JPH0662665B2 (en) |
| AT (1) | ATE45957T1 (en) |
| AU (1) | AU580646B2 (en) |
| CA (1) | CA1262894A (en) |
| DD (1) | DD242231A5 (en) |
| DE (2) | DE3446661A1 (en) |
| DK (1) | DK166502B1 (en) |
| ES (1) | ES8701194A1 (en) |
| FI (1) | FI83089C (en) |
| GR (1) | GR853017B (en) |
| HU (1) | HU193357B (en) |
| IE (1) | IE58147B1 (en) |
| NO (1) | NO163014C (en) |
| NZ (1) | NZ214449A (en) |
| PT (1) | PT81690B (en) |
| ZA (1) | ZA859666B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4434488A1 (en) * | 1994-09-14 | 1996-03-21 | Schering Ag | Steroid esters and amides, processes for their preparation and their pharmaceutical use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA8231B (en) * | 1981-01-09 | 1982-11-24 | Roussel Uclaf | New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained |
| EP0116974B1 (en) * | 1983-02-18 | 1986-10-29 | Schering Aktiengesellschaft | 11-beta-aryl-estradienes, process for their preparation and pharmaceutical compositions containing them |
| ES8502612A1 (en) * | 1983-06-15 | 1985-02-01 | Schering Ag | 13-Alpha-alkyl gonanes, their preparation and pharmaceutical compositions containing them. |
-
1984
- 1984-12-18 DE DE19843446661 patent/DE3446661A1/en not_active Withdrawn
-
1985
- 1985-12-03 FI FI854788A patent/FI83089C/en not_active IP Right Cessation
- 1985-12-05 NZ NZ214449A patent/NZ214449A/en unknown
- 1985-12-13 AT AT85115925T patent/ATE45957T1/en not_active IP Right Cessation
- 1985-12-13 EP EP85115925A patent/EP0186834B1/en not_active Expired
- 1985-12-13 DE DE8585115925T patent/DE3572670D1/en not_active Expired
- 1985-12-16 ES ES549998A patent/ES8701194A1/en not_active Expired
- 1985-12-16 GR GR853017A patent/GR853017B/el unknown
- 1985-12-16 DD DD85284398A patent/DD242231A5/en not_active IP Right Cessation
- 1985-12-16 IE IE316985A patent/IE58147B1/en not_active IP Right Cessation
- 1985-12-17 CA CA000497807A patent/CA1262894A/en not_active Expired
- 1985-12-17 DK DK587585A patent/DK166502B1/en not_active IP Right Cessation
- 1985-12-17 PT PT81690A patent/PT81690B/en not_active IP Right Cessation
- 1985-12-17 NO NO855090A patent/NO163014C/en unknown
- 1985-12-17 JP JP60282175A patent/JPH0662665B2/en not_active Expired - Lifetime
- 1985-12-17 HU HU854813A patent/HU193357B/en not_active IP Right Cessation
- 1985-12-18 ZA ZA859666A patent/ZA859666B/en unknown
- 1985-12-18 AU AU51436/85A patent/AU580646B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU580646B2 (en) | 1989-01-19 |
| NO163014B (en) | 1989-12-11 |
| JPH0662665B2 (en) | 1994-08-17 |
| GR853017B (en) | 1986-04-15 |
| CA1262894A (en) | 1989-11-14 |
| ES549998A0 (en) | 1986-12-01 |
| DK166502B1 (en) | 1993-06-01 |
| PT81690A (en) | 1986-01-01 |
| JPS61145197A (en) | 1986-07-02 |
| IE58147B1 (en) | 1993-07-14 |
| ATE45957T1 (en) | 1989-09-15 |
| ES8701194A1 (en) | 1986-12-01 |
| NZ214449A (en) | 1989-01-06 |
| DE3446661A1 (en) | 1986-06-19 |
| NO163014C (en) | 1990-03-21 |
| FI83089C (en) | 1991-05-27 |
| DK587585A (en) | 1986-06-19 |
| FI854788A0 (en) | 1985-12-03 |
| ZA859666B (en) | 1986-08-27 |
| HU193357B (en) | 1987-09-28 |
| FI854788A (en) | 1986-06-19 |
| DD242231A5 (en) | 1987-01-21 |
| PT81690B (en) | 1988-02-17 |
| EP0186834B1 (en) | 1989-08-30 |
| FI83089B (en) | 1991-02-15 |
| HUT40138A (en) | 1986-11-28 |
| EP0186834A2 (en) | 1986-07-09 |
| EP0186834A3 (en) | 1986-11-26 |
| NO855090L (en) | 1986-06-19 |
| DK587585D0 (en) | 1985-12-17 |
| AU5143685A (en) | 1986-06-26 |
| DE3572670D1 (en) | 1989-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |