GB1538227A - 16,16-disubstituted steroids of the androstene series - Google Patents

16,16-disubstituted steroids of the androstene series

Info

Publication number
GB1538227A
GB1538227A GB11819/75A GB1181975A GB1538227A GB 1538227 A GB1538227 A GB 1538227A GB 11819/75 A GB11819/75 A GB 11819/75A GB 1181975 A GB1181975 A GB 1181975A GB 1538227 A GB1538227 A GB 1538227A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
radicals
radical
alkyl radical
group
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
Application number
GB11819/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB11819/75A priority Critical patent/GB1538227A/en
Priority to IE412/76A priority patent/IE42308B1/en
Priority to IL58505A priority patent/IL58505A/en
Priority to IL49132A priority patent/IL49132A/en
Priority to DE2610497A priority patent/DE2610497C2/en
Priority to FR7607328A priority patent/FR2304345A1/en
Priority to AT191376A priority patent/AT357700B/en
Priority to SE7603410A priority patent/SE7603410L/en
Priority to BE165323A priority patent/BE839751A/en
Priority to AU12207/76A priority patent/AU501246B2/en
Priority to CA248,260A priority patent/CA1069498A/en
Priority to DK123476A priority patent/DK143757C/en
Priority to JP51030741A priority patent/JPS51118756A/en
Priority to NLAANVRAGE7602949,A priority patent/NL184111C/en
Priority to CH354376A priority patent/CH621560A5/en
Priority to ZA761324A priority patent/ZA761324B/en
Priority to CA306,343A priority patent/CA1069496A/en
Publication of GB1538227A publication Critical patent/GB1538227A/en
Priority to CH228479A priority patent/CH631996A5/en
Priority to SE7902256A priority patent/SE7902256L/en
Priority to AT398879A priority patent/AT368524B/en
Priority to IL58505A priority patent/IL58505A0/en
Priority to FR8004184A priority patent/FR2445340A1/en
Priority to DK102480A priority patent/DK102480A/en
Priority to JP60291811A priority patent/JPS61178920A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

Pharmaceutically utilisable 3-ketosteroids which are disubstituted in position 16 and have the formula I <IMAGE> in which R3 are alkyl radicals with 1 to 5 carbon atoms, alkenyl or cycloalkyl radicals with 3 to 6 carbon atoms or phenylalkyl radicals with 1 to 3 carbon atoms in the alkyl radical, it being possible for the phenyl radicals to be substituted, R4 is the hydroxyl group or the radical -OR6 where R6 is an acyl radical with 2 to 7 carbon atoms, an alkyl radical with 1 to 4 carbon atoms, or the benzyl group which can be substituted, and R5 is a hydrogen atom or an alkyl radical with 1 to 5 carbon atoms, it also being possible for R4 and R5, together with the carbon atom to which they are bonded, to form the carbonyl group, are obtained by removing the protective group in the compound of the formula I in which the double bond is in the 5,6 position and the 3-carbonyl group is protected by ketal, hemithioketal or thioketal. The double bond rearranges during the elimination and provides the required 4,5 bond in the final product. The prepared compounds are particularly valuable for the treatment of androgen-dependent skin disorders such as acne and seborrhoea and of other androgen-dependent disorders associated with skin and hair glands.
GB11819/75A 1975-03-21 1975-03-21 16,16-disubstituted steroids of the androstene series Expired GB1538227A (en)

Priority Applications (24)

Application Number Priority Date Filing Date Title
GB11819/75A GB1538227A (en) 1975-03-21 1975-03-21 16,16-disubstituted steroids of the androstene series
IE412/76A IE42308B1 (en) 1975-03-21 1976-03-01 16, 16-disubstituted steroids of the androstene series
IL58505A IL58505A (en) 1975-03-21 1976-03-02 16,1l-disubstituted androst-5-ene derivatives and their preparation
IL49132A IL49132A (en) 1975-03-21 1976-03-02 16,1l-disubstituted androst-4-en-3-ones,their preparation and pharmaceutical compositions containing them
DE2610497A DE2610497C2 (en) 1975-03-21 1976-03-12 3-keto steroids disubstituted in the 16-position, process for their preparation and pharmaceuticals containing these compounds
FR7607328A FR2304345A1 (en) 1975-03-21 1976-03-15 DERIVATIVES OF STEROIDS
AT191376A AT357700B (en) 1975-03-21 1976-03-16 METHOD FOR PRODUCING NEW 3-KETOSTEROIDS DISUBSTITUTED IN 16-POSITION
SE7603410A SE7603410L (en) 1975-03-21 1976-03-18 PHARMACEUTICAL ACTIVE ASSOCIATIONS
BE165323A BE839751A (en) 1975-03-21 1976-03-18 STEROID DERIVATIVES
CA248,260A CA1069498A (en) 1975-03-21 1976-03-19 Pharmaceutically active steroids
NLAANVRAGE7602949,A NL184111C (en) 1975-03-21 1976-03-19 PROCESS FOR PREPARING ANDROSTONE AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE.
AU12207/76A AU501246B2 (en) 1975-03-21 1976-03-19 16, 16 disubstituted androstenes
DK123476A DK143757C (en) 1975-03-21 1976-03-19 ANALOGY PROCEDURE FOR THE PREPARATION OF 16,16-DISUBSTITUTED 3-OXOANDROSTEN
JP51030741A JPS51118756A (en) 1975-03-21 1976-03-19 Novel steroids * pharmaceutical composition containing same and preparation thereof
CH354376A CH621560A5 (en) 1975-03-21 1976-03-22 Process for the preparation of 3-ketosteroids disubstituted in position 16
ZA761324A ZA761324B (en) 1975-03-21 1976-04-04 Pharmaceutically active compounds
CA306,343A CA1069496A (en) 1975-03-21 1978-06-28 Intermediates for pharmaceutically active steroids
CH228479A CH631996A5 (en) 1975-03-21 1979-03-09 Process for the preparation of 16-disubstituted steroids
SE7902256A SE7902256L (en) 1975-03-21 1979-03-13 NEW ASSOCIATIONS
AT398879A AT368524B (en) 1975-03-21 1979-05-31 METHOD FOR PRODUCING NEW 3-KETOSTEROIDS DISUBSTITUTED IN 16-POSITION
IL58505A IL58505A0 (en) 1975-03-21 1979-10-19 16,16-disubstituted androst-5-ene derivatives and their preparation
FR8004184A FR2445340A1 (en) 1975-03-21 1980-02-26 INTERMEDIATES FOR THE PREPARATION OF STEROID DERIVATIVES HAVING PHARMACEUTICAL ACTIVITY
DK102480A DK102480A (en) 1975-03-21 1980-03-10 INTERMEDIATES FOR THE PREPARATION OF 16,16 DIALKYL STEROIDS
JP60291811A JPS61178920A (en) 1975-03-21 1985-12-24 Medicinal composition containing 4-ene-16, 16-disubstituted-3-one steroid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB11819/75A GB1538227A (en) 1975-03-21 1975-03-21 16,16-disubstituted steroids of the androstene series

Publications (1)

Publication Number Publication Date
GB1538227A true GB1538227A (en) 1979-01-10

Family

ID=9993275

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11819/75A Expired GB1538227A (en) 1975-03-21 1975-03-21 16,16-disubstituted steroids of the androstene series

Country Status (15)

Country Link
JP (2) JPS51118756A (en)
AT (1) AT357700B (en)
AU (1) AU501246B2 (en)
BE (1) BE839751A (en)
CA (1) CA1069498A (en)
CH (2) CH621560A5 (en)
DE (1) DE2610497C2 (en)
DK (1) DK143757C (en)
FR (2) FR2304345A1 (en)
GB (1) GB1538227A (en)
IE (1) IE42308B1 (en)
IL (2) IL49132A (en)
NL (1) NL184111C (en)
SE (2) SE7603410L (en)
ZA (1) ZA761324B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992005763A1 (en) * 1990-10-04 1992-04-16 Beecham Group Plc Composition containing steroid derivatives
WO1992007586A1 (en) * 1990-10-31 1992-05-14 Beecham Group Plc Topical composition with retinoid penetration enhancer
WO1993017687A1 (en) * 1992-03-10 1993-09-16 Smithkline Beecham Plc Topical compositions containing steroids
WO2003051903A1 (en) * 2001-12-19 2003-06-26 Chugai Seiyaku Kabushiki Kaisha Androstane derivative having substituent in 7- and 17-positions

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1602960A (en) * 1977-05-25 1981-11-18 Beecham Group Ltd Process for preparing 16,16-disubstituted steroids of the androstene series
DE2943778A1 (en) * 1979-10-26 1981-05-07 Schering Ag Berlin Und Bergkamen, 1000 Berlin 17-Alpha:alkyl-4,15-androstadiene-3-one derivs. - topical antiandrogens effective against acne, seborrhoea, alopecia and hirsutism
DE3514272A1 (en) * 1985-04-17 1986-10-23 Schering AG, 1000 Berlin und 4709 Bergkamen DERMATICA
JPS63300153A (en) * 1987-05-29 1988-12-07 日本碍子株式会社 Building enamel panel
CN108558975B (en) * 2018-04-26 2021-03-02 昆明理工大学 12 beta-hydroxy-androstane 4, 14-diene-16-ketone compound and application thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3853926A (en) * 1973-05-29 1974-12-10 Searle & Co 17{62 -hydroxy-16,16-dimethylester-4-en-3-one

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992005763A1 (en) * 1990-10-04 1992-04-16 Beecham Group Plc Composition containing steroid derivatives
WO1992007586A1 (en) * 1990-10-31 1992-05-14 Beecham Group Plc Topical composition with retinoid penetration enhancer
WO1993017687A1 (en) * 1992-03-10 1993-09-16 Smithkline Beecham Plc Topical compositions containing steroids
WO2003051903A1 (en) * 2001-12-19 2003-06-26 Chugai Seiyaku Kabushiki Kaisha Androstane derivative having substituent in 7- and 17-positions

Also Published As

Publication number Publication date
IE42308B1 (en) 1980-07-16
AU501246B2 (en) 1979-06-14
FR2304345A1 (en) 1976-10-15
ZA761324B (en) 1977-02-23
CA1069498A (en) 1980-01-08
DE2610497C2 (en) 1986-10-16
FR2445340B1 (en) 1983-02-11
CH631996A5 (en) 1982-09-15
IL49132A0 (en) 1976-05-31
DK123476A (en) 1976-09-22
ATA191376A (en) 1979-12-15
DK143757B (en) 1981-10-05
IL49132A (en) 1980-05-30
IL58505A0 (en) 1980-01-31
DK143757C (en) 1982-03-22
DE2610497A1 (en) 1976-10-07
NL7602949A (en) 1976-09-23
FR2304345B1 (en) 1980-11-07
JPS625920B2 (en) 1987-02-07
NL184111C (en) 1989-04-17
IE42308L (en) 1976-09-21
JPS6355488B2 (en) 1988-11-02
JPS51118756A (en) 1976-10-18
AT357700B (en) 1980-07-25
FR2445340A1 (en) 1980-07-25
NL184111B (en) 1988-11-16
JPS61178920A (en) 1986-08-11
CH621560A5 (en) 1981-02-13
SE7603410L (en) 1976-09-22
BE839751A (en) 1976-09-20
SE7902256L (en) 1979-03-13
AU1220776A (en) 1977-09-22

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19960226