SE312553B - - Google Patents

Info

Publication number
SE312553B
SE312553B SE11025/62A SE1102562A SE312553B SE 312553 B SE312553 B SE 312553B SE 11025/62 A SE11025/62 A SE 11025/62A SE 1102562 A SE1102562 A SE 1102562A SE 312553 B SE312553 B SE 312553B
Authority
SE
Sweden
Prior art keywords
group
steroid
formula
ethylenic bond
general formula
Prior art date
Application number
SE11025/62A
Inventor
H Smith
G Hughes
Original Assignee
H Smith
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 H Smith filed Critical H Smith
Publication of SE312553B publication Critical patent/SE312553B/xx

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565Compounds 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
    • A61K31/567Compounds 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
    • AHUMAN NECESSITIES
    • A43FOOTWEAR
    • A43BCHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
    • A43B3/00Footwear characterised by the shape or the use
    • A43B3/12Sandals; Strap guides thereon
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565Compounds 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565Compounds 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
    • A61K31/568Compounds 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
    • A61K31/569Compounds 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J1/00Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J63/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J7/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes 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.
SE11025/62A 1961-10-19 1962-10-15 SE312553B (en)

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
SE312553B true SE312553B (en) 1969-07-21

Family

ID=10397775

Family Applications (6)

Application Number Title Priority Date Filing Date
SE11023/62A SE312551B (en) 1961-10-19 1962-10-15
SE11024/62A SE312552B (en) 1961-10-19 1962-10-15
SE11026/62A SE313809B (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
SE05984/66A SE340619B (en) 1961-10-19 1966-05-02

Family Applications Before (4)

Application Number Title Priority Date Filing Date
SE11023/62A SE312551B (en) 1961-10-19 1962-10-15
SE11024/62A SE312552B (en) 1961-10-19 1962-10-15
SE11026/62A SE313809B (en) 1961-10-19 1962-10-15
SE01423/67A SE335526B (en) 1961-10-19 1962-10-15

Family Applications After (1)

Application Number Title Priority Date Filing Date
SE05984/66A SE340619B (en) 1961-10-19 1966-05-02

Country Status (12)

Country Link
AT (4) AT264730B (en)
CH (5) CH432509A (en)
CY (1) CY429A (en)
DE (4) DE1618855B2 (en)
DK (6) DK113641B (en)
ES (1) ES281669A1 (en)
FI (4) FI41024B (en)
FR (1) FR2796M (en)
GB (2) GB1041278A (en)
MY (1) MY6800075A (en)
NO (4) NO122644B (en)
SE (6) SE312551B (en)

Families Citing this family (3)

* 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
US8617597B2 (en) 2006-07-06 2013-12-31 Bayer Intellectual Property Gmbh Pharmaceutical composition containing a tetrahydrofolic acid
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

Also Published As

Publication number Publication date
DK115621B (en) 1969-10-27
SE340619B (en) 1971-11-29
AT256356B (en) 1967-08-25
NO122644B (en) 1971-07-26
SE312551B (en) 1969-07-21
CY429A (en) 1968-01-15
ES281669A1 (en) 1963-03-16
FI41024B (en) 1969-04-30
SE312552B (en) 1969-07-21
DE1468604B1 (en) 1970-07-02
DE1618855B2 (en) 1973-04-05
GB1041279A (en) 1966-09-01
DK121228B (en) 1971-09-27
SE313809B (en) 1969-08-25
FR2796M (en) 1964-09-21
AT256354B (en) 1967-08-25
NO122643B (en) 1971-07-26
MY6800075A (en) 1968-12-31
DK113641B (en) 1969-04-14
DE1618855C3 (en) 1973-10-25
DE1617818B2 (en) 1976-12-09
DK129652C (en) 1975-04-07
CH432509A (en) 1967-03-31
DE1793595A1 (en) 1972-02-03
DE1468604C2 (en) 1971-03-04
DE1793608B1 (en) 1972-05-04
NO122645B (en) 1971-07-26
AT256355B (en) 1967-08-25
FI41025B (en) 1969-04-30
CH455763A (en) 1968-05-15
SE335526B (en) 1971-06-01
DK124753B (en) 1972-11-20
NO122646B (en) 1971-07-26
CH450408A (en) 1968-01-31
CH459195A (en) 1968-07-15
CH450407A (en) 1968-01-31
AT264730B (en) 1968-09-10
DK129652B (en) 1974-11-04
GB1041278A (en) 1966-09-01
FI41027B (en) 1969-04-30
DE1617818A1 (en) 1972-05-18
DE1793595B2 (en) 1975-10-30
DK115549B (en) 1969-10-20
FI41026B (en) 1969-04-30
DE1618855A1 (en) 1972-05-18

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