EP1658306A1 - Delta 15 -d-homosteroide mit androgener wirkung - Google Patents
Delta 15 -d-homosteroide mit androgener wirkungInfo
- Publication number
- EP1658306A1 EP1658306A1 EP04764445A EP04764445A EP1658306A1 EP 1658306 A1 EP1658306 A1 EP 1658306A1 EP 04764445 A EP04764445 A EP 04764445A EP 04764445 A EP04764445 A EP 04764445A EP 1658306 A1 EP1658306 A1 EP 1658306A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydroxy
- 17ass
- group
- homo
- dien
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Definitions
- the invention relates to ⁇ 15 -D homosteroids of the general
- ⁇ 15 -D homosteroids of the estran and androstane series are not yet known. However, are known from US Pat. No. 4,155,918 and Avery et al., Steroids, 1990, vol. 55, pp. 59-64) ⁇ 16 -D-homosteroids which have androgenic and antigonadotropic activity.
- the object of the present invention is to provide further androgenically active compounds and to provide a technically simple and effective process for their preparation.
- R ⁇ for a hydrogen atom or ad- 6 -alkyl, vinyl, ethynyl or C n F 2n + r group, with n 1, 2, 3 and
- R 4 represents a hydrogen atom
- R 4 for a hydrogen atom or R 2 and R 3 together for an oxygen atom
- R 4 for a hydrogen atom or 2 for a hydroxy group, a group OC (O) -R 20 , OC (O) NH-R Ü 20 u or OR 20 , where R 20 is a C ⁇ _ ⁇ 2 alkyl group, a C 3-8 - Cycloalkyl group, an aryl group or an arylC 1-4 alkyl group, which is optionally substituted, means, and
- R 3 and R 4 together form a double bond
- R 7 is a hydrogen atom, a halogen atom, a hydroxyl group or a C n F 2n + ⁇ -
- X represents an oxygen atom, two hydrogen atoms or a hydroxyimino group
- R 8 represents a hydrogen atom, a methyl or ethyl group
- R 9 represents a hydrogen atom or a halogen atom or together with R 10 represents a double bond
- R 10 represents a hydrogen atom, a hydroxy group, a methyl or ethyl group or together with R 9 stands for a double bond
- R 11 represents a hydrogen atom, a C -4 alkyl group, a nitrile group, a
- R 12 is a hydrogen atom, a or means a nitrile group
- R 13 is a hydrogen atom or together with R 7 is a double bond
- R 16 represents a hydrogen atom or together with R 3 a double bond
- R 15 represents a hydroxyl group
- R 14 and R 15 represent a hydrogen atom or together for a double bond, a [2,3c] oxadiazole ring, a [3,2c] isoxazole ring or one
- R 17 represents a hydrogen atom or a methyl group
- Y stands for an oxygen or nitrogen atom
- the meandering lines on R 4 , R 7 , R 8 , R 11 , R 12 , R 13 , R 14 and R 15 mean that these substituents can be in the ⁇ or ⁇ position , and their pharmaceutically acceptable salts.
- the compounds according to the invention have androgenic activity.
- the C ⁇ -4 alkyl group is a branched or unbranched alkyl radical, which is preferably formed by a methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or tert-butyl group.
- the C 6 alkyl group is a branched or unbranched alkyl radical, which is preferably by a methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or tert-butyl group, n- Pentyl, i-pentyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl group is formed.
- the -CC 2 alkyl group is a branched or unbranched alkyl radical, which is preferably replaced by a methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl, i-pentyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl group, an octyl, nonyl, decyl or Undecyl group is formed.
- the C 3 -s-cycloalkyl group is preferably a mono- or bicyclic group, such as a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group.
- aryl group stands for a substituted or unsubstituted aryl radical having preferably 6 to 15 carbon atoms, such as a phenyl group, a substituted phenyl group, such as a halophenyl group or a nitrophenyl group, or a naphthyl group.
- aryl-C - -alkyl group should preferably be an alkyl radical substituted with an aryl radical, which together preferably have 7 to 15 carbon atoms, the aryl radical and / or alkyl radical being further substituents, such as preferably a halogen atom, a hydroxyl or a methoxy - or can carry nitrile group.
- Particularly preferred aryl radicals are a free or aromatically substituted benzyl group, such as a benzyl group or a halogenobenzyl group.
- halogen atom stands for a fluorine, chlorine, bromine or iodine atom.
- R 7 preferably denotes a hydrogen atom
- a chlorine atom denotes a bromine atom
- R 10 preferably denotes a hydrogen atom, a hydroxyl or a methyl group
- R 9 preferably denotes a hydrogen atom or a fluorine atom
- R 8 is preferably a hydrogen atom or a methyl group, the methyl group being particularly preferred.
- R 7 preferably denotes a hydrogen atom, a chlorine atom, a bromine atom or a hydroxyl group or a trifluoromethyl group and R 8 preferably denotes a hydrogen atom or a methyl group, the methyl group being particularly preferred.
- R 7 preferably denotes a hydrogen atom, a chlorine atom, a bromine atom or a hydroxyl group or a trifluoromethyl group and R 11 , R 12 preferably denotes a hydrogen atom.
- R 11 , R 12 preferably denotes a hydrogen atom.
- a double bond in the 1,2 position is preferred.
- R 17 H or CH 3 is equally preferred.
- R 7 preferably denotes a hydrogen atom, a chlorine atom, a bromine atom or a hydroxy group or a trifluoromethyl group
- R 8 preferably denotes a hydrogen atom or a methyl group, with a methyl group being particularly preferred
- R 13 and R preferably together represent a double bond and Y preferably represents an oxygen atom.
- R 8 preferably denotes a hydrogen atom or a methyl group, with a methyl group being particularly preferred
- R 12 preferably stands for a hydrogen atom
- R 13 and R 16 preferably stand for a hydrogen atom or together for one Double bond
- R 15 preferably each represents a hydroxyl group or R 14 and R 15 preferably together represent a [3,2c] pyrazole ring
- R 11 preferably denotes a C 4 alkyl group or nitrile group.
- R 1 preferably denotes a methyl group or an ethyl group, the methyl group being particularly preferred.
- R 2 preferably denotes a hydroxyl group, a formyloxy group, acetyloxy group, propionyloxy group, butyryloxy group, [(trans-4-butylcyclohexyl) carbonyl] ⁇ oxy group, phenylpropionyloxy group, iso-butyryloxy group, heptanyloxy group, undecanyloxy group or phenylaminocarbonyloxy group, particularly preferably being the hydroxyloxy group,
- R 3 preferably denotes a methyl, a trifluoromethyl, an ethyl, a pentafluoromethyl or an ethynyl group, the methyl, ethyl, trifluoromethyl and pentafluoromethyl group being particularly preferred.
- R 4 preferably represents a hydrogen atom.
- ⁇ 15 -D-homosteroids are listed below: 1) 17ass-hydroxy-D-homo-androstane-4,15-dien-3-one, 2) 17ass, 4-dihydroxy-D-homo-androstane-4, 15-dien-3-one, 3) 17ass-hydroxy-4-chloro-D-homo-androstane-4,15-dien-3-one, 4) 17ass-hydroxy-4-bromo-D-homo-androstane 4,15-dien-3-one, 5) 17ass-hydroxy-4-trifluoromethyl-D-homo-androstane-4,15-dien-3-one, 6) 17ass, 11 ⁇ -dihydroxy-D-homo-androstane-4,15-dien-3-one,
- Another object of the invention is a technically simple and effective process for the preparation of ⁇ 15 -D-homosteroids of the general formula (I).
- R 1 and STEROID which have the meaning given above, in the presence of acids, such as, for example, p-toluenesulfonic acid, with acylating agents, such as, for example, isopropenyl acetate (Hosoda, H. et al., Chem. Phar. Bull., 23, 1975, 3141-3145), acetic anhydride (Rasmusson, GH, Arth, GE, Steroids, 22, 1973, 107-111) or the like to the dienole acetates in a known manner and then using reducing agents, such as NaBH, to give the corresponding 17ass hydroxy-D -homo- ⁇ 1 asteroids reduced.
- acids such as, for example, p-toluenesulfonic acid
- acylating agents such as, for example, isopropenyl acetate (Hosoda, H. et al., Chem. Phar. Bull., 23, 1975, 3
- Known steroid base bodies can be used to prepare the compounds of general formula II with substructures A to F.
- the following steroid base bodies can be used, for example:
- keto groups in the starting materials of substructures A to F can be protected as ketals or thioacetals by methods known to the person skilled in the art.
- the substituents R 7 to R 15 can be introduced into the partial structures A to F either before or after the incorporation of the D-homo- ⁇ 15 cycle by methods known to the person skilled in the art.
- inorganic acids include hydrochloric acid, hydrobromic acid, sulfuric acid and phosphoric acid
- organic acids include acetic acid, propionic acid, maleic acid, fumaric acid, succinic acid, benzoic acid, ascorbic acid, oxalic acid, Salicylic acid, tartaric acid, citric acid, lactic acid, malic acid, mandelic acid, cinnamic acid and methanesulfonic acid.
- the compounds of the invention have androgenic activity, as shown in Table 1 below.
- 17ass-hydroxy-7 ⁇ -methyl-D-homoestra-4,16-dien-3-one is described as an androgen with antigonadotropic properties in Steroids, 1990, 55, 59-64.
- 17ass-hydroxy-7 ⁇ -methyl-D-homoestra-4,16-dien-3-one shows only a small amount
- the androgenic activity of the ⁇ 15 -D-homo-steroids according to the invention is therefore different from that of the 17ass-hydroxy-7-methyl-D-homoestra-4,16-dien-3-one known from the literature (steroids, 1990, 55, 59-64).
- HRT hormone replacement therapy
- the present invention therefore also relates to pharmaceutical compositions which contain at least one ⁇ 15 -D-homosteroid of the general formula (I), optionally together with pharmaceutically acceptable auxiliaries and carriers, and also the use of these compounds, inter alia, for therapy or for preparation of pharmaceutical preparations, inter alia for the therapy of the aforementioned clinical pictures.
- compositions and medicaments can be intended for oral, rectal, vaginal, subcutaneous, percutaneous, intravenous or intramuscular application.
- they contain at least one compound of the general formula I.
- the medicaments of the invention are produced in a known manner with the customary solid or liquid carriers or diluents and the commonly used pharmaceutical-technical auxiliaries in accordance with the desired type of application with a suitable dosage.
- the preferred preparations are in a dosage form which is suitable for oral administration. Dosage forms of this type are, for example, tablets, film-coated tablets, dragees, capsules, pills, powders, solutions or suspensions or even depot forms.
- parenteral preparations such as injection solutions are also suitable.
- Suppositories and agents for vaginal use may also be mentioned as preparations.
- Corresponding tablets can be mixed, for example, by mixing the active ingredient with known auxiliaries, for example inert diluents such as dextrose, sugar, sorbitol, mannitol, polyvinylpyrrolidone, disintegrants such as corn starch or alginic acid, binders such as starch or gelatin, lubricants such as magnesium stearate or talc and / or agents Achieving a depot effect such as carboxyl polymethylene, carboxylmethyl cellulose, cellulose acetate phthalate or polyvinyl acetate can be obtained.
- auxiliaries for example inert diluents such as dextrose, sugar, sorbitol, mannitol, polyvinylpyrrolidone, disintegrants such as corn starch or alginic acid, binders such as starch or gelatin, lubricants such as magnesium stearate or talc and / or agents Achieving a depot effect such
- Coated tablets can accordingly be produced by coating cores produced analogously to the tablets with agents conventionally used in tablet coatings, for example polyvinylpyrrolidone or shellac, gum tarabicum, talc, titanium oxide or sugar.
- the coated tablet can also consist of several layers, wherein the auxiliaries mentioned above for the tablets can be used.
- Solutions or suspensions with the compounds of general formula I according to the invention can additionally taste-improving agents such as saccharin, cyclamate or sugar and z.
- B. contain flavorings such as vanillin or orange extract. They can also contain suspending agents such as sodium carboxymethyl cellulose or preservatives such as p-hydroxybenzoates.
- Capsules containing the compounds of the general formula I can be prepared, for example, by the compound (s) of the general. Formula I mixed with an inert carrier such as milk sugar or sorbitol and encapsulated in gelatin capsules.
- Suitable suppositories can be produced, for example, by mixing them with suitable carriers such as neutral fats or polyethylene glycol or their derivatives.
- 3ß-Hvdroxy-D-homoandrostan-5,15-dien-17ass-tetrahvdropyranylether 5.2 g of 3ß-acetoxy-D-homoandrostane-5,15-dien-17ass-tetrahydropyranylether are dissolved in 175 ml of methanol and 125 ml of THF. 7.5 g of K 2 CO 3 and 2.5 ml of water are added with vigorous stirring. After 3.5 hours, the mixture is concentrated to about 1/6.
- 3-Keto-D-homoandrostane-4, 15-diene-17ass-tetrahydropyranyl ether 4.5 g of 3 ⁇ -hydroxy-D-homoandrostane-5.15-diene-17ass-tetrahydropyranylether are dissolved in 125 ml of toluene under argon. After adding 1.6 g of Al (O-iPr) 3 , the mixture is heated to 110 ° C. for 2.5 hours. At RT, it is washed twice with 250 ml of 1 M K-Na tartrate solution. The aqueous phases are extracted with ethyl acetate. The united org. Phases are with sat. Washed NaCl solution, dried over MgSO 4 , filtered and concentrated in vacuo. 3-Keto-D-homoandrostane-4,15-diene-17ass-tetrahydropyranyl ether is obtained.
- the preparation is carried out analogously to 17ass-hydroxy-4 ⁇ , 5 ⁇ -epoxy-D-homoandrost-15-en-3-one.
- the residue obtained consists of a mixture of 4 ⁇ , 5 - or 4ß, 5ß-epoxides and is used in the next stage without further purification.
- Step 3 3ß-acetoxy-D-homo-5 ⁇ -androst-15-en-17 nd-tetrahydropyranylether
- Step 4 3ß-Hydroxy-D-homo-5 ⁇ -androst-15-en-17 nd-tetrahydropyranylether
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Epidemiology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US49666903P | 2003-08-21 | 2003-08-21 | |
DE10339532A DE10339532A1 (de) | 2003-08-21 | 2003-08-21 | Delta 15-D-Homosteroide mit androgener Wirkung |
PCT/EP2004/009468 WO2005021573A1 (de) | 2003-08-21 | 2004-08-19 | Δ15-d-homosteroide mit androgener wirkung |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1658306A1 true EP1658306A1 (de) | 2006-05-24 |
Family
ID=34276519
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04764445A Withdrawn EP1658306A1 (de) | 2003-08-21 | 2004-08-19 | Delta 15 -d-homosteroide mit androgener wirkung |
Country Status (11)
Country | Link |
---|---|
US (1) | US7388003B2 (de) |
EP (1) | EP1658306A1 (de) |
JP (1) | JP2007502801A (de) |
KR (1) | KR20060091295A (de) |
AU (1) | AU2004268040A1 (de) |
BR (1) | BRPI0413787A (de) |
CA (1) | CA2534831A1 (de) |
EC (1) | ECSP066441A (de) |
IL (1) | IL173608A0 (de) |
MX (1) | MXPA06002034A (de) |
WO (1) | WO2005021573A1 (de) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200745156A (en) * | 2005-06-17 | 2007-12-16 | Organon Nv | Steroids having a mixed androgenic and progestagenic profile |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1054262A (de) * | ||||
NZ182539A (en) * | 1975-11-11 | 1979-07-11 | Hoffmann La Roche | 3-substituted-d-homoan drost-ko-en-17a -ols |
IL51468A (en) * | 1976-02-23 | 1981-01-30 | Sparamedica Ag | 17 -hydroxy- -d-homosteroid derivatives,their preparation and pharmaceutical compositions containing them |
NL7703448A (nl) * | 1976-04-13 | 1977-10-17 | Hoffmann La Roche | Nieuwe d-homosteroiden. |
DE10247399A1 (de) * | 2002-10-08 | 2004-04-29 | Schering Ag | Pharmazeutische Zubereitungen, Verwendung dieser Zubereitung und Verfahren zur Erhöhung der Bioverfügbarkeit von peroral zu applizierenden Arzneistoffen |
-
2004
- 2004-08-19 JP JP2006523619A patent/JP2007502801A/ja active Pending
- 2004-08-19 BR BRPI0413787-6A patent/BRPI0413787A/pt not_active IP Right Cessation
- 2004-08-19 CA CA002534831A patent/CA2534831A1/en not_active Abandoned
- 2004-08-19 MX MXPA06002034A patent/MXPA06002034A/es not_active Application Discontinuation
- 2004-08-19 EP EP04764445A patent/EP1658306A1/de not_active Withdrawn
- 2004-08-19 KR KR1020067003436A patent/KR20060091295A/ko not_active Application Discontinuation
- 2004-08-19 AU AU2004268040A patent/AU2004268040A1/en not_active Abandoned
- 2004-08-19 WO PCT/EP2004/009468 patent/WO2005021573A1/de active Application Filing
- 2004-08-23 US US10/923,080 patent/US7388003B2/en not_active Expired - Fee Related
-
2006
- 2006-02-08 IL IL173608A patent/IL173608A0/en unknown
- 2006-03-20 EC EC2006006441A patent/ECSP066441A/es unknown
Non-Patent Citations (1)
Title |
---|
See references of WO2005021573A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU2004268040A1 (en) | 2005-03-10 |
IL173608A0 (en) | 2006-07-05 |
WO2005021573A1 (de) | 2005-03-10 |
ECSP066441A (es) | 2006-09-18 |
KR20060091295A (ko) | 2006-08-18 |
US7388003B2 (en) | 2008-06-17 |
BRPI0413787A (pt) | 2006-11-07 |
CA2534831A1 (en) | 2005-03-10 |
JP2007502801A (ja) | 2007-02-15 |
MXPA06002034A (es) | 2006-05-17 |
US20050131076A1 (en) | 2005-06-16 |
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