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GB1041279A - 13-alkyl steroid ketones - Google Patents

13-alkyl steroid ketones

Info

Publication number
GB1041279A
GB1041279A GB37618/61A GB3761861A GB1041279A GB 1041279 A GB1041279 A GB 1041279A GB 37618/61 A GB37618/61 A GB 37618/61A GB 3761861 A GB3761861 A GB 3761861A GB 1041279 A GB1041279 A GB 1041279A
Authority
GB
United Kingdom
Prior art keywords
group
steroid
formula
ethylenic bond
general formula
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
GB37618/61A
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
Application filed by Individual filed Critical Individual
Priority to GB37618/61A priority Critical patent/GB1041279A/en
Priority to GB37617/61A priority patent/GB1041278A/en
Priority to SE11026/62A priority patent/SE313809B/xx
Priority to SE11024/62A priority patent/SE312552B/xx
Priority to SE01423/67A priority patent/SE335526B/xx
Priority to SE11025/62A priority patent/SE312553B/xx
Priority to SE11023/62A priority patent/SE312551B/xx
Priority to DK448162AA priority patent/DK113641B/en
Priority to CH1275267A priority patent/CH459195A/en
Priority to CH1562666A priority patent/CH450408A/en
Priority to CH1562566A priority patent/CH455763A/en
Priority to CH1562766A priority patent/CH432509A/en
Priority to CH1217162A priority patent/CH450407A/en
Priority to DE1962S0111837 priority patent/DE1617818B2/en
Priority to FI1879/62A priority patent/FI41027B/fi
Priority to AT822762A priority patent/AT264730B/en
Priority to NO146141A priority patent/NO122644B/no
Priority to DK449762AA priority patent/DK115621B/en
Priority to FI1876/62A priority patent/FI41024B/fi
Priority to NO146143A priority patent/NO122646B/no
Priority to DE19621793595 priority patent/DE1793595C3/en
Priority to NO146142A priority patent/NO122645B/no
Priority to DE19621793608 priority patent/DE1793608B1/en
Priority to NO146140A priority patent/NO122643B/no
Priority to FI1878/62A priority patent/FI41026B/fi
Priority to DE1962S0082099 priority patent/DE1468604C2/en
Priority to DK449662AA priority patent/DK115549B/en
Priority to ES281669A priority patent/ES281669A1/en
Priority to FI1877/62A priority patent/FI41025B/fi
Priority to DK449562AA priority patent/DK121228B/en
Priority to DE19621618855 priority patent/DE1618855B2/en
Priority to AT825862A priority patent/AT256356B/en
Priority to AT825662A priority patent/AT256354B/en
Priority to AT825762A priority patent/AT256355B/en
Priority to FR921556A priority patent/FR2796M/en
Priority to SE05984/66A priority patent/SE340619B/xx
Publication of GB1041279A publication Critical patent/GB1041279A/en
Priority to CY42968A priority patent/CY429A/en
Priority to MY196875A priority patent/MY6800075A/en
Priority to DK227069AA priority patent/DK129652B/en
Priority to DK339670AA priority patent/DK124753B/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/567—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 position 17 alpha, e.g. mestranol, norethandrolone
    • A—HUMAN NECESSITIES
    • A43—FOOTWEAR
    • A43B—CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
    • A43B3/00—Footwear characterised by the shape or the use
    • A43B3/12—Sandals; Strap guides thereon
    • 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
    • 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
    • A61K31/569—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 substituted in position 17 alpha, e.g. ethisterone
    • 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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Woven Fabrics (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Manufacturing Of Printed Wiring (AREA)

Abstract

Novel steroids of the general formula <FORM:1041279/C2/1> wherein R represents an alkyl group of at least 2 carbon atoms, R2 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group (a suitable substituent is methoxy) and ring A contains an ethylenic bond terminating at the 5-position, are prepared by hydrolysing a steroid of the general formula <FORM:1041279/C2/2> wherein X represents an acid-hydrolysable protected 3-oxo group, e.g. an alkoxy group such as the methoxy, ethoxy, methoxymethoxy and dihydroxypropyloxy, an alkylthio group such as alkylthio and benzylthio, an acyloxy group such as acetoxy, a dialkylamino group, an N-pyrrolidyl group, an alkylenedioxy group such as ethylenedioxy, an alkylenedithio group, or an alkylenethiooxy group, which is accompanied by an ethylenic bond terminating at the 5-position; by selectively reducing a steroid of the general formula <FORM:1041279/C2/3> wherein R represents an alkyl group and R1 has the above significance (a) by hydrogenation in solution in a non-protonic solvent using a palladium or Raney nickel catalyst to saturate the 14(15)-ethylenic bond, (b) by a carbonyl-reducing reagent such as sodium borohydride or lithium aluminium hydride, before or after the catalytic hydrogenation step to convert the carbonyl group to a hydroxymethylene group, (c) by the action of alkali metal in liquid ammonia after the catalytic hydrogenation and simultaneously with or after the carbonyl-reducing step, to saturate the 8(9)-ethylenic bond, and (d) by the action of alkali metal in liquid ammonia in the presence of a proton donor that is an alcohol having less than 6 carbon atoms, simultaneously with or after the saturation of the 8(9)-ethylene bond to form a steroid of the formula <FORM:1041279/C2/4> selectively oxidizing this compound to the corresponding 17-keto compound, and reacting this compound with an organo-metallic reagent containing the group R2; by ketalizing a corresponding steroid of the formula <FORM:1041279/C2/5> or <FORM:1041279/C2/6> wherein R represents an alkyl group, with an alkylene glycol to form a steroid of the formula <FORM:1041279/C2/7> wherein X represents an alkylenedioxy group and ring B has an ethylenic bond terminating at the 5-position, oxidizing this steroid to the corresponding 17-keto compound, treating the 17-keto compound with an organo-metal ethynylating agent to form the 17a -R2-17b -hydroxy-grouping and hydrolysing the ketal group at the 3-position to form a 4(5)-ethylenic steroid of the first formula above wherein R1 has the above significance and R2 represents an alkynyl group; by oxidizing a corresponding steroid diol of the formula <FORM:1041279/C2/8> having an ethylenic bond terminating at the 5-position, by isomerizing the corresponding steroids having an ethylenic bond in the 5(10)-position under basic or acidic conditions to form the corresponding 4(5)-unsaturated compounds; and by selectively reducing the steroids of the first general formula above wherein R2 is an unsaturated group to form corresponding steroids in which R2 is more saturated, for example by catalytic hydrogenation. The above formulae include all states of resolution except the resolved 13a -enantiomer. Pharmaceutical compositions which may be administered orally or by injection contain as the active ingredient a steroid of the first general formula above. The compositions may be used as anabolic agents.
GB37618/61A 1961-10-19 1961-10-19 13-alkyl steroid ketones Expired GB1041279A (en)

Priority Applications (40)

Application Number Priority Date Filing Date Title
GB37618/61A GB1041279A (en) 1961-10-19 1961-10-19 13-alkyl steroid ketones
GB37617/61A GB1041278A (en) 1961-10-19 1961-10-19 13-alkyl steroid ketone derivatives
SE11026/62A SE313809B (en) 1961-10-19 1962-10-15
SE11024/62A SE312552B (en) 1961-10-19 1962-10-15
SE01423/67A SE335526B (en) 1961-10-19 1962-10-15
SE11025/62A SE312553B (en) 1961-10-19 1962-10-15
SE11023/62A SE312551B (en) 1961-10-19 1962-10-15
DK448162AA DK113641B (en) 1961-10-19 1962-10-17 Process for the production of steroid ketones.
CH1275267A CH459195A (en) 1961-10-19 1962-10-17 Process for the preparation of 13-alkyl steroid diols
CH1562666A CH450408A (en) 1961-10-19 1962-10-17 Method of making steroid ketones
CH1562566A CH455763A (en) 1961-10-19 1962-10-17 Method of making steroid ketones
CH1562766A CH432509A (en) 1961-10-19 1962-10-17 Method of making steroid ketones
CH1217162A CH450407A (en) 1961-10-19 1962-10-17 Process for the production of 13-homologated steroid ketones
NO146143A NO122646B (en) 1961-10-19 1962-10-18
FI1877/62A FI41025B (en) 1961-10-19 1962-10-18
AT822762A AT264730B (en) 1961-10-19 1962-10-18 Process for the production of new steroid ketones
NO146141A NO122644B (en) 1961-10-19 1962-10-18
DK449762AA DK115621B (en) 1961-10-19 1962-10-18 Process for the production of unsaturated steroid ketones.
FI1876/62A FI41024B (en) 1961-10-19 1962-10-18
DE1962S0111837 DE1617818B2 (en) 1961-10-19 1962-10-18 ORAL OR INJECTABLE ANTI-CONCEPTION AGENTS
DE19621793595 DE1793595C3 (en) 1961-10-19 1962-10-18 Intermediates for the preparation of 17-alpha-alkyl-, -alkenyl- or -alkynyl-13 beta-alkylgon-4- or -5 (10) -en-17 beta-ol-3-ones
NO146142A NO122645B (en) 1961-10-19 1962-10-18
DE19621793608 DE1793608B1 (en) 1961-10-19 1962-10-18 17alpha-alkyl-, -alkenyl- or -alkynyl-13ss-alkylgon-4- or-5 (10) -en-17ss-ol-3-ones
NO146140A NO122643B (en) 1961-10-19 1962-10-18
FI1878/62A FI41026B (en) 1961-10-19 1962-10-18
DE1962S0082099 DE1468604C2 (en) 1961-10-19 1962-10-18 Process for the preparation of 17alpha-alkyl-, -alkenyl- or -alkynyl-13beta-alkylgon-4- or-5 (10) -en-17beta-ol-3-ones
DK449662AA DK115549B (en) 1961-10-19 1962-10-18 Process for the production of unsaturated steroid ketones.
ES281669A ES281669A1 (en) 1961-10-19 1962-10-18 A procedure for preparing a steroid cetone (Machine-translation by Google Translate, not legally binding)
FI1879/62A FI41027B (en) 1961-10-19 1962-10-18
DK449562AA DK121228B (en) 1961-10-19 1962-10-18 Analogous process for the production of unsaturated steroid ketones.
DE19621618855 DE1618855B2 (en) 1961-10-19 1962-10-18 GONANES 3,17 DIOLS AND THE METHOD OF MANUFACTURING THEM
AT825862A AT256356B (en) 1961-10-19 1962-10-19 Process for the production of new 17-alkyl steroid ketones
AT825662A AT256354B (en) 1961-10-19 1962-10-19 Process for the production of new unsaturated steroid ketones
AT825762A AT256355B (en) 1961-10-19 1962-10-19 Process for the preparation of new unsaturated 17-alkyl steroid ketones
FR921556A FR2796M (en) 1961-10-19 1963-01-16 New drugs consisting of ketosteroids related to 19-nortestosterone.
SE05984/66A SE340619B (en) 1961-10-19 1966-05-02
CY42968A CY429A (en) 1961-10-19 1968-01-15 13-Alkyl steroid ketones
MY196875A MY6800075A (en) 1961-10-19 1968-12-31 13-alkyl steroid ketones
DK227069AA DK129652B (en) 1961-10-19 1969-04-24 17-Hydrocarbon-substituted 3,17-dihydroxy-13-alkyl-gonenes for use as intermediates in the preparation of pharmacologically active, corresponding to 17-hydrocarbon-substituted 3-oxo-17-hydroxy-13-alkyl-gon-4 or - 5 (10) -ener.
DK339670AA DK124753B (en) 1961-10-19 1970-06-30 Analogous process for the preparation of 13-alkyl-gonen-3,17-diols.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB37618/61A GB1041279A (en) 1961-10-19 1961-10-19 13-alkyl steroid ketones

Publications (1)

Publication Number Publication Date
GB1041279A true GB1041279A (en) 1966-09-01

Family

ID=10397775

Family Applications (2)

Application Number Title Priority Date Filing Date
GB37618/61A Expired GB1041279A (en) 1961-10-19 1961-10-19 13-alkyl steroid ketones
GB37617/61A Expired GB1041278A (en) 1961-10-19 1961-10-19 13-alkyl steroid ketone derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB37617/61A Expired GB1041278A (en) 1961-10-19 1961-10-19 13-alkyl steroid ketone derivatives

Country Status (12)

Country Link
AT (4) AT264730B (en)
CH (5) CH432509A (en)
CY (1) CY429A (en)
DE (4) DE1468604C2 (en)
DK (6) DK113641B (en)
ES (1) ES281669A1 (en)
FI (4) FI41025B (en)
FR (1) FR2796M (en)
GB (2) GB1041279A (en)
MY (1) MY6800075A (en)
NO (4) NO122645B (en)
SE (6) SE312552B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11617751B2 (en) 2006-07-06 2023-04-04 Bayer Pharma AG Pharmaceutical composition containing a tetrahydrofolic acid

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2636404C2 (en) * 1976-08-12 1983-12-08 Schering AG, 1000 Berlin und 4709 Bergkamen ?? 1?? 5? -17? -Ethynyl steroids of the estran series, processes for their preparation and pharmaceutical preparations containing them
CN104926906B (en) * 2015-06-04 2016-02-10 保定北瑞甾体生物有限公司 A kind of preparation method of 17 Alpha-hydroxy Progesterone

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11617751B2 (en) 2006-07-06 2023-04-04 Bayer Pharma AG Pharmaceutical composition containing a tetrahydrofolic acid

Also Published As

Publication number Publication date
NO122644B (en) 1971-07-26
DE1793595B2 (en) 1975-10-30
DE1793595A1 (en) 1972-02-03
DE1618855A1 (en) 1972-05-18
SE335526B (en) 1971-06-01
DE1793608B1 (en) 1972-05-04
SE312551B (en) 1969-07-21
AT264730B (en) 1968-09-10
SE312552B (en) 1969-07-21
DK124753B (en) 1972-11-20
AT256356B (en) 1967-08-25
AT256354B (en) 1967-08-25
FI41025B (en) 1969-04-30
NO122646B (en) 1971-07-26
DK113641B (en) 1969-04-14
MY6800075A (en) 1968-12-31
DE1617818A1 (en) 1972-05-18
FI41026B (en) 1969-04-30
SE312553B (en) 1969-07-21
DE1617818B2 (en) 1976-12-09
SE340619B (en) 1971-11-29
FI41027B (en) 1969-04-30
DK129652C (en) 1975-04-07
ES281669A1 (en) 1963-03-16
DE1618855B2 (en) 1973-04-05
CH450408A (en) 1968-01-31
CH432509A (en) 1967-03-31
DE1468604C2 (en) 1971-03-04
CY429A (en) 1968-01-15
DE1468604B1 (en) 1970-07-02
CH450407A (en) 1968-01-31
DE1618855C3 (en) 1973-10-25
NO122643B (en) 1971-07-26
DK129652B (en) 1974-11-04
DK115549B (en) 1969-10-20
FI41024B (en) 1969-04-30
GB1041278A (en) 1966-09-01
NO122645B (en) 1971-07-26
CH455763A (en) 1968-05-15
AT256355B (en) 1967-08-25
CH459195A (en) 1968-07-15
DK121228B (en) 1971-09-27
SE313809B (en) 1969-08-25
FR2796M (en) 1964-09-21
DK115621B (en) 1969-10-27

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