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WO1993013122A1 - 3-methylsulfonylhydrazono- et 3-oxyimino-steroides, leur procede de fabrication, preparations pharmaceutiques renfermant ces steroides et leur utilisation dans la fabrication de medicaments - Google Patents

3-methylsulfonylhydrazono- et 3-oxyimino-steroides, leur procede de fabrication, preparations pharmaceutiques renfermant ces steroides et leur utilisation dans la fabrication de medicaments Download PDF

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Publication number
WO1993013122A1
WO1993013122A1 PCT/EP1992/002983 EP9202983W WO9313122A1 WO 1993013122 A1 WO1993013122 A1 WO 1993013122A1 EP 9202983 W EP9202983 W EP 9202983W WO 9313122 A1 WO9313122 A1 WO 9313122A1
Authority
WO
WIPO (PCT)
Prior art keywords
androst
methyl
dimethyl
hydroxyimino
methylsulfonylhydrazono
Prior art date
Application number
PCT/EP1992/002983
Other languages
German (de)
English (en)
Inventor
Dieter Bittler
Helmut Hofmeister
Thomas Brumby
Jörg Kroll
Hermann Künzer
Gerhard Sauer
Karl-Heinrich Fritzemeier
Horst Michna
Original Assignee
Schering Aktiengesellschaft
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE19914143142 external-priority patent/DE4143142A1/de
Priority claimed from DE19924217235 external-priority patent/DE4217235A1/de
Application filed by Schering Aktiengesellschaft filed Critical Schering Aktiengesellschaft
Publication of WO1993013122A1 publication Critical patent/WO1993013122A1/fr

Links

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
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C07J41/0016—Oximes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton

Definitions

  • the present invention relates to 3-methylsulfonylhydrazono- and 3-oxyimino-steroids of the general formula I.
  • X is an oxygen atom or an NH group
  • C 4 -C 5 is a CC single or CC double bond
  • C 15 -C 16 is a CC single or a CC double bond, a) when X is an oxygen atom
  • R ' is a hydrogen atom or a saturated, straight or branched chain hydrocarbon radical having 1 to 4 or 3 or 4 carbon atoms, or an unsaturated, straight or branched chain hydrocarbon radical having 2 to 4 or 3 or 4
  • R 1 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom or a methyl group, or, if C 4 -C 5 is a CC double bond, also a fluorine, chlorine or bromine atom,
  • R 6 and R 6 ' each represent a hydrogen atom or, if C 4 -C 5 is a CC double bond, also together a 6,6-methylene or ethylene group or R 6 is a hydrogen atom and R 6 'is a methyl group,
  • R 7 and R 7 ' are each a hydrogen atom or, if R 6 and R 6' are each a hydrogen atom and C 4 -C 5 are a CC double bond, R 7 or R 7 'are also a saturated or unsaturated hydrocarbon radical with 1 to 4 or .2 to 4
  • Carbon atoms and the other C7 substituent is a hydrogen atom, or
  • R 7 and R 7 ' together represent an alkylidene group with 1 to 4 carbon atoms
  • R 10 represents a hydrogen atom or a methyl group
  • R 11 is a hydrogen, fluorine or chlorine atom
  • R 11 ' is a hydrogen atom or together with R 11 is a methylene group
  • R 15 and R 1 6 independently of one another are a hydrogen atom or an ⁇ - or ⁇ -hydrocarbon radical having 1 to 4 carbon atoms or, if C 15 -C 16 is a CC single bond, together a 15 ⁇ , 16 ⁇ - or 15 ⁇ , 16 ⁇ -methylene group , and
  • R 17 ' is a hydrogen atom or an acyl group R "-CO-, wherein R" is a saturated or unsaturated hydrocarbon radical having 1 or 2 to 6 carbon atoms or one
  • the compounds of the general formula I are strong antiandrogens with the standard antiandrogen cyproterone acetate (17 ⁇ -acetoxy-6-chloro-1 ⁇ , 2 ⁇ -methylene-4,6-pregnadiene-3,20-dione; Friedmund Neumann, Rudolf Wiechert, Die130 von Cyproteronacetat, Unusual ways in the development of a drug; MPS Medical-Pharmaceutical Study Society eV Mainz, Mainz 1984) comparable antiandrogenic potency.
  • cyproterone acetate In contrast to cyproterone acetate, however, they are peripherally selective. Peripherally selective antiandrogenic activity means that the corresponding compounds have no influence on the hypothalamic-pituitary system, which means that there is no centrally controlled counter-regulation (feedback) and no androgen-active substances are released.
  • the (E) -3-mesyloxyimino-4,17 ⁇ -dimethyl-androst-4-en-17 ⁇ -ol (A) and the (E) -4,17 ⁇ -dimethyl-3-methylsulfonylhydrazono-androst-4- en-17 ⁇ -ol (B) in Anti-androgen test after subcutaneous administration of 10 mg / day / animal to intact rats after seven days of treatment has an almost equally strong anti-androgenic effect as cyproterone acetate. In contrast to this, however, they have peripheral selectivity in the rat, as is evident from the lack of counterregulation (unchanged testosterone level) 24 hours after administration of 5 mg sc of the substance.
  • the present invention also relates to a process for the preparation of the compounds of the general formula I.
  • R 'a is a hydrogen atom or a saturated, straight-chain or branched-chain hydrocarbon radical having 1 to 4 or 3 or 4 carbon atoms or an unsaturated straight or branched-chain hydrocarbon radical having 2 to 4 or 3 or 4 carbon atoms and X is a chlorine or bromine atom,
  • R is a saturated, straight-chain or branched-chain hydrocarbon radical having 1 to 4 or 3 or 4 carbon atoms and Y is a chlorine or bromine atom,
  • reaction of the compounds of the general formula II a) with the hydroxylamine derivative of the general formula III is preferably carried out in pyridine as solvent; oxime formation works best with one
  • Reaction temperature in the range of 0 ° C to 80 ° C; b) with methylsulfonyl hydrazide is preferably alcoholic, in particular
  • reaction takes place at room temperature; if necessary, the reaction mixture can also be heated to the boiling point of the solvent used.
  • the present invention also relates to pharmaceutical preparations which contain at least one compound of the general formula I and a pharmaceutically acceptable carrier.
  • the compounds according to the invention can be used primarily for the production of medicaments which are suitable for the therapy of benign prostatic hyperplasia and androgen-dependent prostate cancer. But they can also be used to treat other androgen-dependent disorders and diseases.
  • the pharmaceutical preparations can be intended for oral, parenteral, transdermal, rectal or vaginal application and can be prepared in solid or liquid dosage form such as capsules, tablets, suppositories, solutions, suspensions or emulsions.
  • a daily dose of 10-1000 mg / day of a compound of the general formula I is administered.
  • the active compounds of the general formula I are processed further using customary inert and pharmaceutically acceptable vehicles (carriers) in accordance with galenical methods.
  • the formulation, production and administration of the pharmaceutical preparations which contain the active compounds according to the invention can be carried out in a manner analogous to that of the standard antiandrogen cyproterone acetate.
  • 15 ⁇ -Hydroxy-4-androsten-3,17-dione 1 (DE-A 3 404 862) is added to the 15 ⁇ -acetate 2 in the
  • Hexane-acetone gradient contains 320 mg of 17 ⁇ -hydroxy-17 ⁇ -methyl-11-methylene-androst-4-en-3-one with a melting point of 155- 1 JC. i) 17 ⁇ -Hydroxy-17 ⁇ -methyl-11-methylene-4- (phenylthiomethyl) -androst-4-en-3-one
  • Tetrahydrofuran added dropwise After 30 min, saturated ammonium chloride solution is added, diluted with ethyl acetate, washed with water, dried and evaporated down i. Vacuum on.
  • the crude product is stirred in 70 ml of tetrahydrofuran with 59 ml of tetrabutylammonium fluoride solution (1 mol in tetrahydrofuran) at room temperature. After 30 min, diluted with ethyl acetate, washed with water, dried and evaporated down i. Vacuum on. After chromatographing the
  • Triethylamine contains, with a methylene chloride (methyl tert-butyl ether) gradient, 230 mg (E) -4,17 ⁇ -dimethyl-3-methylsulfonylhydrazono-androsta-4,15-dien-17 ⁇ -ol are obtained. Melting point: 152-153 ° C.
  • Pentane (methyl tert-butyl ether) gradients become 160 mg

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

On décrit de nouveaux 3-méthylsulfonylhydrazono- et 3-oxyimino-stéroïdes, de la formule générale (I) dans laquelle X désigne un atome d'oxygène ou un groupe NH, C4-C5 est une liaison simple C-C ou une double liaison C-C, et C15-C16 est une liaison simple C-C ou une double liaison C-C, et R' en fonction de X, ainsi que les autres substituants, ont les significations données dans la description. Ces nouveaux composés constituent des antiandrogènes à sélectivité périphérique, à efficacité comparable au cyprotérone-acétate, et conviennent pour la fabrication de médicaments.
PCT/EP1992/002983 1991-12-22 1992-12-22 3-methylsulfonylhydrazono- et 3-oxyimino-steroides, leur procede de fabrication, preparations pharmaceutiques renfermant ces steroides et leur utilisation dans la fabrication de medicaments WO1993013122A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEP4143142.1 1991-12-22
DE19914143142 DE4143142A1 (de) 1991-12-22 1991-12-22 3-methylsulfonylhydrazono-steroide
DEP4217235.7 1992-05-20
DE19924217235 DE4217235A1 (de) 1992-05-20 1992-05-20 3-Oxyimino-steroide

Publications (1)

Publication Number Publication Date
WO1993013122A1 true WO1993013122A1 (fr) 1993-07-08

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/002983 WO1993013122A1 (fr) 1991-12-22 1992-12-22 3-methylsulfonylhydrazono- et 3-oxyimino-steroides, leur procede de fabrication, preparations pharmaceutiques renfermant ces steroides et leur utilisation dans la fabrication de medicaments

Country Status (2)

Country Link
AU (1) AU3257993A (fr)
WO (1) WO1993013122A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995003319A1 (fr) * 1993-07-23 1995-02-02 The Procter & Gamble Company Aceto-thioacetate de cyproterone
WO1995003320A1 (fr) * 1993-07-23 1995-02-02 The Procter & Gamble Company Thiopivalate de cyproterone
US5438134A (en) * 1990-07-09 1995-08-01 Jenapharm Gmbh Process for the production of unsaturated 17 α-cyanomethyl-17 β-h
FR2719588A1 (fr) * 1994-05-03 1995-11-10 Roussel Uclaf Nouveau procédé de préparation de la substance "S" et nouveaux intermédiaires.
WO2000039148A1 (fr) * 1998-12-23 2000-07-06 Schering Aktiengesellschaft Nouveaux derives de testosterone 7-alpha, 17-alpha-bis-alkyles et leur utilisation pour la therapie de longue duree de maladies androgeno-dependantes
US6369047B2 (en) * 1997-11-26 2002-04-09 Research Triangle Institute Androgenic steroid compounds and a method of making and using the same
DE10049736A1 (de) * 2000-09-29 2002-04-18 Jenapharm Gmbh 17alpha-Fluoralkylsteroide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
US6767903B1 (en) 1998-12-23 2004-07-27 Schering Ag New7α, 17α-bis-alkylated testosterone derivatives and their use in long-term therapy of androgen-dependent diseases
DE102007063498A1 (de) 2007-12-29 2009-07-02 Bayer Schering Pharma Aktiengesellschaft 15,16-Methylen-steroid-17,17-Lactol-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel

Citations (12)

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GB996256A (en) * 1964-04-07 1965-06-23 Searle & Co Steroid compounds
US3211756A (en) * 1963-07-23 1965-10-12 Searle & Co 3-hydroxyimino-17alpha-(lower alkyl)-5alpha-androstan-17beta-ols and the optionally substituted 3-acyloxyimino and 3-alkoxyimino derivatives corresponding
US3299107A (en) * 1965-02-12 1967-01-17 Searle & Co 17-(unsaturated hydrocarbon-substituted)-3-hydroxyimino-5alpha-androstan-17beta-ols,alkyl and acyl derivatives thereof
GB1123104A (en) * 1965-10-22 1968-08-14 Ortho Pharma Corp 3-oxime-steroids and method of preparation
DE1493150A1 (de) * 1963-06-28 1969-08-07 Scherico Ltd Verfahren zur Herstellung von tertiaeren Aminoalkyloximinoderivaten der OE?reihe
AU416613B2 (en) * 1967-03-29 1971-08-20 Ortho Pharmaceutical Corporation 3-oxime steroids and method of preparation
AU423149B2 (en) * 1967-06-21 1972-04-11 Ortho Pharmaceutical Corporation 3-oximes and3-oxime esters of 19 nostestosterones
US3780073A (en) * 1966-07-06 1973-12-18 Ortho Pharma Corp 3-oximes of 19-nortestosterone esters
FR2200010A1 (fr) * 1972-09-26 1974-04-19 Warner Lambert Co
FR2219783A1 (fr) * 1973-03-01 1974-09-27 Ortho Pharma Corp
FR2318645A1 (fr) * 1975-07-24 1977-02-18 Ortho Pharma Corp 3-oximes d'esters de d-17a-ethynyl-19-nortestosterone et leur procede de preparation
EP0001029A1 (fr) * 1977-08-31 1979-03-07 Roussel-Uclaf Procédé de préparation d'oximes en 3 de stéroides

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1493150A1 (de) * 1963-06-28 1969-08-07 Scherico Ltd Verfahren zur Herstellung von tertiaeren Aminoalkyloximinoderivaten der OE?reihe
US3211756A (en) * 1963-07-23 1965-10-12 Searle & Co 3-hydroxyimino-17alpha-(lower alkyl)-5alpha-androstan-17beta-ols and the optionally substituted 3-acyloxyimino and 3-alkoxyimino derivatives corresponding
GB996256A (en) * 1964-04-07 1965-06-23 Searle & Co Steroid compounds
US3299107A (en) * 1965-02-12 1967-01-17 Searle & Co 17-(unsaturated hydrocarbon-substituted)-3-hydroxyimino-5alpha-androstan-17beta-ols,alkyl and acyl derivatives thereof
GB1123104A (en) * 1965-10-22 1968-08-14 Ortho Pharma Corp 3-oxime-steroids and method of preparation
US3780073A (en) * 1966-07-06 1973-12-18 Ortho Pharma Corp 3-oximes of 19-nortestosterone esters
AU416613B2 (en) * 1967-03-29 1971-08-20 Ortho Pharmaceutical Corporation 3-oxime steroids and method of preparation
AU423149B2 (en) * 1967-06-21 1972-04-11 Ortho Pharmaceutical Corporation 3-oximes and3-oxime esters of 19 nostestosterones
FR2200010A1 (fr) * 1972-09-26 1974-04-19 Warner Lambert Co
FR2219783A1 (fr) * 1973-03-01 1974-09-27 Ortho Pharma Corp
FR2318645A1 (fr) * 1975-07-24 1977-02-18 Ortho Pharma Corp 3-oximes d'esters de d-17a-ethynyl-19-nortestosterone et leur procede de preparation
EP0001029A1 (fr) * 1977-08-31 1979-03-07 Roussel-Uclaf Procédé de préparation d'oximes en 3 de stéroides

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 115, no. 13, 30. September 1991, Columbus, Ohio, US; abstract no. 136483, YAO, JUN ET AL 'Synthesis and Biological Evaluation of ORF 9371 and Its Derivatives' Seite 1024 ;Spalte 1 ; *
CHEMICAL ABSTRACTS, vol. 67, no. 9, 28. August 1967, Columbus, Ohio, US; abstract no. 44012, SHOJI, HARA ET AL 'Quantitative Resolution of Syn and Anti Isomers of Steroidal alpha,beta-unsaturated Oximes and O-Methyloximes' Seite 4149 ;Spalte 2 ; *
CHEMICAL ABSTRACTS, vol. 69, no. 15, 7. Oktober 1968, Columbus, Ohio, US; abstract no. 59477, OKA, KITARO ET AL 'Nuclear Magnetic Resonance Spectra of Syn and Anti Isomers of Steroidal 3-Ketoximes' Seite 5570 ;Spalte 1 ; *
CHEMICAL ABSTRACTS, vol. 77, no. 17, 23. Oktober 1972, Columbus, Ohio, US; abstract no. 114669, P. CATSOULACOS 'Beckmann Rearrangement of Testosterone Oximes' Seite 473 ;Spalte 1 ; *
CHEMICAL ABSTRACTS, vol. 97, no. 5, 2. August 1982, Columbus, Ohio, US; abstract no. 39219, ZHAO, ZIQING ET AL 'Study on Steroid Oximes. (I). Synthesis and Biological Evaluation of Forty-Three Compounds' Seite 603 ;Spalte 1 ; *
JOURNAL OF CHROMATOGRAPHY Bd. 202, Nr. 2, 1980, Seiten 187 - 194 OKA, KITARO ET AL 'Linear Relationship between the Logarithm of the Equilibrium Constants and the Logarithm of the Liquid Chromatographic Separation Factors for Tautomers Obtained in Different Solvents' *
JOURNAL OF LIQUID CHROMATOGRAPHY Bd. 13, Nr. 17, 1990, Seiten 3455 - 3463 S. A. MATLIN ET AL 'Resolution and Identification of Steroid Oxime Syn and Anti Isomers by HPLC' *
STEROIDS. Bd. 33, Nr. 1, Januar 1979, SAN FRANCISCO US Seiten 65 - 83 S. TANAYAMA ET AL 'Disposition and Metabolism of 16-beta-Ethyl-17-beta-Hydrox y-4-estren-3-one (TSAA-291), A New Antiandrogen, in Rats' *
STEROIDS. Bd. 38, Nr. 3, September 1981, SAN FRANCISCO US Seiten 243 - 262 G. R. CUNNINGHAM ET AL 'Steroid Structural Requirements for High Affinity Binding to Human Sex Steroid Binding Protein (SBP)' *
THYMUS Bd. 3, Nr. 2, 1981, Seiten 105 - 117 A. B. MCCRUDEN ET AL 'Androgen Binding Cytosol Receptors in the Rat Thymus: Physiochemical Properties, Specificity and Localization' *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5438134A (en) * 1990-07-09 1995-08-01 Jenapharm Gmbh Process for the production of unsaturated 17 α-cyanomethyl-17 β-h
WO1995003319A1 (fr) * 1993-07-23 1995-02-02 The Procter & Gamble Company Aceto-thioacetate de cyproterone
WO1995003320A1 (fr) * 1993-07-23 1995-02-02 The Procter & Gamble Company Thiopivalate de cyproterone
US5439901A (en) * 1993-07-23 1995-08-08 The Procter & Gamble Company Cyproterone thiopivalate
FR2719588A1 (fr) * 1994-05-03 1995-11-10 Roussel Uclaf Nouveau procédé de préparation de la substance "S" et nouveaux intermédiaires.
US6369047B2 (en) * 1997-11-26 2002-04-09 Research Triangle Institute Androgenic steroid compounds and a method of making and using the same
US6670352B2 (en) 1997-11-26 2003-12-30 Research Triangle Institute Androgenic steroid compounds and a method of making and using the same
US6864248B2 (en) 1997-11-26 2005-03-08 Research Triangle Institute Androgenic steroid compounds and a method of making and using the same
WO2000039148A1 (fr) * 1998-12-23 2000-07-06 Schering Aktiengesellschaft Nouveaux derives de testosterone 7-alpha, 17-alpha-bis-alkyles et leur utilisation pour la therapie de longue duree de maladies androgeno-dependantes
US6767903B1 (en) 1998-12-23 2004-07-27 Schering Ag New7α, 17α-bis-alkylated testosterone derivatives and their use in long-term therapy of androgen-dependent diseases
DE10049736A1 (de) * 2000-09-29 2002-04-18 Jenapharm Gmbh 17alpha-Fluoralkylsteroide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
WO2002026759A3 (fr) * 2000-09-29 2002-06-20 Jenapharm Gmbh 17α-FLUORALKYLSTEROIDES, LEUR PROCEDE DE PRODUCTION ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CES COMPOSES
CN1305890C (zh) * 2000-09-29 2007-03-21 舍林股份公司 17α－氟烷基甾体、其制备方法以及包含这些化合物的药物组合物
DE102007063498A1 (de) 2007-12-29 2009-07-02 Bayer Schering Pharma Aktiengesellschaft 15,16-Methylen-steroid-17,17-Lactol-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel

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