GB1361411A - 11beta-methyl-17alpha-propadienyl steroids - Google Patents

11beta-methyl-17alpha-propadienyl steroids

Info

Publication number
GB1361411A
GB1361411A GB1523671A GB1523671A GB1361411A GB 1361411 A GB1361411 A GB 1361411A GB 1523671 A GB1523671 A GB 1523671A GB 1523671 A GB1523671 A GB 1523671A GB 1361411 A GB1361411 A GB 1361411A
Authority
GB
United Kingdom
Prior art keywords
methyl
propadienyl
lialh
compounds
prepared
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
GB1523671A
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.)
Sandoz AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Publication of GB1361411A publication Critical patent/GB1361411A/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
    • 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
    • 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
    • C07J75/00—Processes for the preparation of steroids in general

Abstract

1361411 17α-Propadienyl steroids SANDOZ Ltd 17 May 1971 [21 May 1970] 15236/71 Heading C2U The invention relates to the #<SP>4</SP>- and #<SP>5(10)</SP>- derivatives of steroids of formula (wherein R is Me, Et or Pr<SP>n</SP>; and R 1 is H, Me, C 2-4 alkanoyl, or acetoacetyl), these compounds being claimed per se with the exception of 11#- methyl - 17α - propadienyl - 17# - hydroxyestr- 4 - en - 3 - one (for which see Specification 1,361,412). Compounds I are prepared by acid hydrolysis of the corresponding 3-alkoxy-#<SP>2,5(10)</SP>, 3-alkoxy- #<SP>3,5</SP>, 3,3-dialkoxy-#<SP>5(10)</SP>, 3,3-ethlenedioxy-#<SP>5(10)</SP> or 3,3-trimethylenedioxy-#<SP>5(10)</SP> compounds, and are interconvertible by 17-alkanoylation, 17- acetoacetylation (e.g. with diketen) and isomerization of #<SP>5(10)</SP> to #<SP>4</SP>. 3 - Methoxy - 11# - methyl - 17α - propadienylestra - 2,5(10) - dien - 17# - ol and its 13 - ethyl homologue are prepared from the corresponding 17-ones by organometallation to give 17α-(3- dimethylamino - 1 - propynyl) - 17# - ols followed by quaternation to give 17α-(3-trimethylammonio - 1 - propynyl) - 17# - ols followed by reduction with NaAlH 2 (OCH 2 CH 2 OCH 3 ) 2 , LiAlH 4 , LiBH 4 , LiGaH 4 , Mg(AlH 4 ) 2 , LiAlH(Me)(Bu<SP>i</SP>) 2 , LiAlH(OMe) 3 , AlHEt 2 or B 2 H 6 . 3,17# - Dimethoxy - 11# - methyl - 17α - propadienylestra - 2,5(10) - diene is prepared by methylation of the corresponding 17#-ol. Progestational compositions for oral and parenteral administration comprise a compound I (excluding 11#-methyl-17α-propadienyl-17#- hydroxyestr-4-en-3-one) and a carrier.
GB1523671A 1970-05-21 1971-05-17 11beta-methyl-17alpha-propadienyl steroids Expired GB1361411A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3954670A 1970-05-21 1970-05-21
US5868270A 1970-07-27 1970-07-27

Publications (1)

Publication Number Publication Date
GB1361411A true GB1361411A (en) 1974-07-24

Family

ID=26716242

Family Applications (2)

Application Number Title Priority Date Filing Date
GB5586873A Expired GB1361412A (en) 1970-05-21 1971-05-17 11beta-methyl-17alpha-propadienyl steroid
GB1523671A Expired GB1361411A (en) 1970-05-21 1971-05-17 11beta-methyl-17alpha-propadienyl steroids

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB5586873A Expired GB1361412A (en) 1970-05-21 1971-05-17 11beta-methyl-17alpha-propadienyl steroid

Country Status (10)

Country Link
BE (1) BE767430A (en)
CH (1) CH552579A (en)
DE (1) DE2124950A1 (en)
DK (1) DK126423B (en)
ES (1) ES418711A1 (en)
FI (1) FI49295C (en)
FR (1) FR2100672B1 (en)
GB (2) GB1361412A (en)
NL (1) NL7106566A (en)
SE (1) SE373129B (en)

Also Published As

Publication number Publication date
GB1361412A (en) 1974-07-24
CH552579A (en) 1974-08-15
DE2124950A1 (en) 1971-12-09
SE373129B (en) 1975-01-27
FI49295B (en) 1975-01-31
ES418711A1 (en) 1977-02-01
BE767430A (en) 1971-11-19
FI49295C (en) 1975-05-12
NL7106566A (en) 1971-11-23
FR2100672A1 (en) 1972-03-24
FR2100672B1 (en) 1974-08-23
DK126423B (en) 1973-07-16

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees