GB1010053A - 13-alkyl 5,10-ethylenic steroid 3-ketones and their enol ethers - Google Patents

13-alkyl 5,10-ethylenic steroid 3-ketones and their enol ethers

Info

Publication number
GB1010053A
GB1010053A GB32670/60A GB3267060A GB1010053A GB 1010053 A GB1010053 A GB 1010053A GB 32670/60 A GB32670/60 A GB 32670/60A GB 3267060 A GB3267060 A GB 3267060A GB 1010053 A GB1010053 A GB 1010053A
Authority
GB
United Kingdom
Prior art keywords
group
formula
steroids
hydroxymethylene
trans
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
GB32670/60A
Inventor
Gordon Alan Hughes
Herchel Smith
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.)
Individual
Original Assignee
Individual
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 to NL256208D priority Critical patent/NL256208A/xx
Priority to NL111253D priority patent/NL111253C/xx
Application filed by Individual filed Critical Individual
Priority to GB32670/60A priority patent/GB1010053A/en
Priority to DE1793659A priority patent/DE1793659C3/en
Priority to DE19611443124 priority patent/DE1443124A1/en
Priority to CH1768665A priority patent/CH430706A/en
Priority to CH1768765A priority patent/CH427785A/en
Priority to CH1093461A priority patent/CH421096A/en
Priority to FR873827A priority patent/FR1393968A/en
Priority to DK375361AA priority patent/DK121369B/en
Priority to AT242268A priority patent/AT282083B/en
Priority to AT714661A priority patent/AT268544B/en
Priority to IT17245/61A priority patent/IT1061739B/en
Priority to SE16052/70A priority patent/SE354064B/xx
Priority to SE01538/68A priority patent/SE334878B/xx
Priority to SE9422/61A priority patent/SE307787B/xx
Priority to FR882617A priority patent/FR1680M/en
Priority to FR908798A priority patent/FR87651E/en
Priority to US00228384A priority patent/US3850911A/en
Priority to FR917484A priority patent/FR41F/en
Priority to US04/388,820 priority patent/US3959322A/en
Publication of GB1010053A publication Critical patent/GB1010053A/en
Priority to DK283471AA priority patent/DK125991B/en
Expired legal-status Critical Current

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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • 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
    • 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
    • C07J21/008—Ketals at position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (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)

Abstract

The invention comprises steroids of the formulae <FORM:1010053/C2/1> and <FORM:1010053/C2/2> wherein R is an alkyl group, R1 is an alkyl group of at least two carbon atoms, X is a hydroxymethylene, acyloxymethylene, carbonyl or ketalized carbonyl group, and the hydrogen atoms and group R1 at the junctions in ring C are in the trans-anti-trans configuration; the preparation of steroids of formula I, wherein R is more widely defined, as a substituted or unsubstituted aliphatic hydrocarbon group of the kind whose linkage to the oxygen atom is stable to the action of an alkali metal in liquid ammonia, R1 is as defined above and X is a hydroxymethylene or ketalized carbonyl group, by reducing, with an alkali metal in liquid ammonia in the presence of a proton donor a corresponding steroid of the formula <FORM:1010053/C2/3> wherein X is a hydroxymethylene, carbonyl or ketalized carbonyl group, ring C is saturated or contains an ethylenic bond terminating at the 9-position, the C : D ring junction is in the trans-configuration, the hydrogen atom at the 8-position where present is anti to the hydrogen atom at the 14-position, and the hydrogen atom at the 9-position where present is trans to the hydrogen atom at the 8-position; the preparation of the steroids of Formula I, wherein X is a carbonyl group by oxidation of the corresponding steroids, wherein X is a hydroxymethylene group; and the preparation of the 3-ketones of Formula II by mild hydrolysis of the steroids of Formula I. Products of Formula I, wherein X is an acyloxymethylene group are prepared by acylation of the corresponding 17-hydroxy compounds. The above structures include all states of resolution except the resolved 13a -enantiomers. Examples are given. Specification 975,596, 991,594, 1,010,051, 1,010,052 and 1,010,054 are referred to.
GB32670/60A 1960-09-22 1960-09-22 13-alkyl 5,10-ethylenic steroid 3-ketones and their enol ethers Expired GB1010053A (en)

Priority Applications (22)

Application Number Priority Date Filing Date Title
NL256208D NL256208A (en) 1960-09-22
NL111253D NL111253C (en) 1960-09-22
GB32670/60A GB1010053A (en) 1960-09-22 1960-09-22 13-alkyl 5,10-ethylenic steroid 3-ketones and their enol ethers
DE1793659A DE1793659C3 (en) 1960-09-22 1961-09-19 Gonan derivatives
DE19611443124 DE1443124A1 (en) 1960-09-22 1961-09-19 Gonan derivatives and processes for their preparation
CH1768665A CH430706A (en) 1960-09-22 1961-09-20 Method of making steroids
CH1768765A CH427785A (en) 1960-09-22 1961-09-20 Method of making steroids
CH1093461A CH421096A (en) 1960-09-22 1961-09-20 Method of making steroids
AT714661A AT268544B (en) 1960-09-22 1961-09-21 Process for the production of new steroid compounds
DK375361AA DK121369B (en) 1960-09-22 1961-09-21 Process for the preparation of 3-oxo-Δ <4> steroids, 3-oxo-Δ <5 (10)> steroids or enol ethers thereof.
AT242268A AT282083B (en) 1960-09-22 1961-09-21 Process for the production of new steroid compounds
FR873827A FR1393968A (en) 1960-09-22 1961-09-21 Steroid substances derived from 19-nortestosterone and processes for their preparation
SE9422/61A SE307787B (en) 1960-09-22 1961-09-22
SE16052/70A SE354064B (en) 1960-09-22 1961-09-22
SE01538/68A SE334878B (en) 1960-09-22 1961-09-22
IT17245/61A IT1061739B (en) 1960-09-22 1961-09-22 PROCESS FOR PREPARING STEROID SUBSTANCES
FR882617A FR1680M (en) 1960-09-22 1961-12-20 New drugs consisting of steroid compounds related to 19-nortestosterone.
FR908798A FR87651E (en) 1960-09-22 1962-09-06 Steroid substances derived from 19-nortestosterone and processes for their preparation
US00228384A US3850911A (en) 1960-09-22 1962-10-04 Steroid synthesis
FR917484A FR41F (en) 1960-09-22 1962-12-04 New drugs consisting of steroid compounds related to 19-nortestosterone.
US04/388,820 US3959322A (en) 1960-09-22 1964-08-11 Synthesis of 13-alkyl-gon-4-ones
DK283471AA DK125991B (en) 1960-09-22 1971-06-10 Enol ethers of 3-oxo-Δ <4> or 3-oxo-Δ <5 (10)> steroids for use as intermediates in the synthesis of 3-oxo-Δ <4> or 3-oxo-Δ <5 ( 10)> - steroids.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB32670/60A GB1010053A (en) 1960-09-22 1960-09-22 13-alkyl 5,10-ethylenic steroid 3-ketones and their enol ethers

Publications (1)

Publication Number Publication Date
GB1010053A true GB1010053A (en) 1965-11-17

Family

ID=10342246

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32670/60A Expired GB1010053A (en) 1960-09-22 1960-09-22 13-alkyl 5,10-ethylenic steroid 3-ketones and their enol ethers

Country Status (8)

Country Link
AT (2) AT282083B (en)
CH (3) CH421096A (en)
DE (2) DE1443124A1 (en)
DK (2) DK121369B (en)
FR (1) FR1393968A (en)
GB (1) GB1010053A (en)
IT (1) IT1061739B (en)
SE (3) SE307787B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012110947A1 (en) 2011-02-17 2012-08-23 Lupin Limited An improved process for preparation of levonorgestrel

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012110947A1 (en) 2011-02-17 2012-08-23 Lupin Limited An improved process for preparation of levonorgestrel

Also Published As

Publication number Publication date
IT1061739B (en) 1983-04-30
DE1793659B2 (en) 1974-08-15
DK125991B (en) 1973-05-28
AT282083B (en) 1970-06-10
DE1793659A1 (en) 1972-01-13
CH421096A (en) 1966-09-30
SE354064B (en) 1973-02-26
FR1393968A (en) 1965-04-02
DE1443124A1 (en) 1968-10-24
AT268544B (en) 1969-02-10
CH430706A (en) 1967-02-28
DE1793659C3 (en) 1975-03-27
DK121369B (en) 1971-10-11
CH427785A (en) 1967-01-15
SE334878B (en) 1971-05-10
SE307787B (en) 1969-01-20

Similar Documents

Publication Publication Date Title
GB1087828A (en) Steroidal derivatives
GB1242194A (en) A new oestratriol and a process for its manufacture
GB1010053A (en) 13-alkyl 5,10-ethylenic steroid 3-ketones and their enol ethers
GB1075545A (en) Improvements in or relating to steroids and the manufacture thereof
GB1014890A (en) Steroid 17ª‰-yi acetals and process for their preparation
GB1023782A (en) New steroids
GB1010054A (en) 13-alkyl steroids related to 19-nortestosterone
GB1071509A (en) Steroid compounds
GB950899A (en) Improvements in or relating to steroidal alkyl ethers
GB1010051A (en) 13-alkyl steroids related to oestrone
SE312553B (en)
ES338729A1 (en) Medicinal compositions which contain 15,16beta-methylene steroids of the 19 nor-androstane series
GB1242372A (en) A new oestratriol and a process for its manufacture
GB1176802A (en) 07-(Substituted Amino)-delta&lt;4&gt;-3-Keto Steroids
GB1101120A (en) 2-aminocarbonyl-3-amino-í¸-steroids
GB1024912A (en) 9,11-ethylenic steroids having an aromatic ring a
GB956691A (en) 3-unsubstituted-í¸-androstene compounds
GB1100441A (en) 13-alkyl 17-halogenoalkynyl-steroid 3-ketones and their derivatives
GB1010052A (en) 13-alkyl steroids related to oestradiol
GB765509A (en) Improvements in or relating to steroids and the preparation thereof
GB913589A (en) 16-alkenyl and 16-alkynylestratriene-3,16,17-triols and ethers thereof
GB1047790A (en) Improvements in or relating to steroid compounds
GB1082953A (en) Steroid derivatives
GB1065189A (en) 6,6-ethylene pregnenes
GB911428A (en) Steroids