GB1353162A - 17alpha-propadienyl steroids - Google Patents

17alpha-propadienyl steroids

Info

Publication number
GB1353162A
GB1353162A GB1523771A GB1523771A GB1353162A GB 1353162 A GB1353162 A GB 1353162A GB 1523771 A GB1523771 A GB 1523771A GB 1523771 A GB1523771 A GB 1523771A GB 1353162 A GB1353162 A GB 1353162A
Authority
GB
United Kingdom
Prior art keywords
methoxy
methyl
ethylenedioxyestra
trien
methylestra
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
GB1523771A
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 GB1353162A publication Critical patent/GB1353162A/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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1353162 17α-Propadienyl steroids SANDOZ Ltd 17 May 1971 [21 May 1970 25 Jan 1971] 15237/71 Heading C2U The invention comprises #<SP>4</SP>-steroids of Formula I and also the #<SP>5(10)</SP>-isomers thereof (wherein R 1 is Me, Et or Pr<SP>2</SP>, and R 2 is H, Me, acetoacetyl or C 2-4 alkanoyl) and their preparation 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-ethylenedioxy-#<SP>5(10)</SP> or 3,3-trimethylenedioxy-#<SP>5(10)</SP> compounds. The inventive compounds are interconvertible by 17-esterification and by isomerization of #<SP>5(10)</SP> to #<SP>4</SP>. 3,17# - Dimethoxy - 9α - methyl - 17α - propadienylestra-2,5(10)-diene (LVII) is prepared from 17,17 - ethylenedioxyestra - 1,3,5(10)- triene-3,11#-diol (L) by the sequence L # 3- methoxy - 17,17 - ethylenedioxyestra - 1,3,5(10)- trien - 11# - ol # 3 - methoxy - 17,17 - ethylenedioxyestra - 1,3,5(10) - trien - 11 - one # 3- methoxy - 9α - methyl - 17,17 - ethylenedioxyestra- 1,3,5(10) - trien - 11 - one (LI) # LI hydrazone # 3 - methoxy - 9α - methyl - 17,17 - ethylenedioxyestra - 1,3,5(10) - triene # 3 - methoxy- 9α - methylestra - 1,3,5(10) - trien - 17 - one (LII) # 3 - methoxy - 9α - methylestra - 2,5(10) - dien- 17# - ol (LIII) # 3 - methoxy - 9α - methylestra- 2,5(10) - dien - 17 - one # 3 - methoxy - 9α- methyl - 17α - (3 - dimethylamino - 1 - propynyl)- estra - 2,5(10) - dien - 17# - ol (LIV) # LIV methiodide (LV) # 3 - methoxy - 9α - methyl- 17α - propadienylestra - 2,5(10) - dien - 17# - ol (LVI) # LVII. In the above sequence, 3-methoxy may be replaced by C 2-4 alkoxy and 13-methyl may be replaced by ethyl or n-propyl. The conversion of LII to LIII may be effected in one step or in two steps via 3 - methoxy - 9α - methylestra - 1,3,5(10)- trien-17#-ol (not exemplified). The conversion of LV to LVI may be effected with NaAlH 2 - (OCH 2 CH 2 OCH 3 ) 2 , LiAlH 4 , LiBH 4 , LiGaH 4 , Mg(AlH 4 ) 2 , LiAlH(Me)(Bui) 2 , LiAlH(OMe) 3 , AlHEt 2 or B 2 H 6 . The #<SP>4</SP>-steroids of Formula I are said to possess progestational activity and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration.
GB1523771A 1970-05-21 1971-05-17 17alpha-propadienyl steroids Expired GB1353162A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3954670A 1970-05-21 1970-05-21
US10961271A 1971-01-25 1971-01-25

Publications (1)

Publication Number Publication Date
GB1353162A true GB1353162A (en) 1974-05-15

Family

ID=26716244

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1523771A Expired GB1353162A (en) 1970-05-21 1971-05-17 17alpha-propadienyl steroids

Country Status (9)

Country Link
BE (1) BE767431A (en)
CH (1) CH548998A (en)
DE (1) DE2124951A1 (en)
DK (1) DK127109B (en)
FI (1) FI49296C (en)
FR (1) FR2100673B1 (en)
GB (1) GB1353162A (en)
NL (1) NL7106568A (en)
SE (1) SE373130B (en)

Also Published As

Publication number Publication date
FR2100673B1 (en) 1974-08-30
CH548998A (en) 1974-05-15
BE767431A (en) 1971-11-19
DK127109B (en) 1973-09-24
NL7106568A (en) 1971-11-23
SE373130B (en) 1975-01-27
FI49296B (en) 1975-01-31
FR2100673A1 (en) 1972-03-24
FI49296C (en) 1975-05-12
DE2124951A1 (en) 1971-12-09

Similar Documents

Publication Publication Date Title
GB1152226A (en) Novel Gona-1,3,5(10)-Trienes, processes for their preparation, and compositions incorporating them
GB1104462A (en) 7ª‡-methyl-steroids of the oestrane series
GB1353162A (en) 17alpha-propadienyl steroids
GB1488995A (en) Compositions containing anti-androgenic compounds
GB1416839A (en) 17beta-hydroxy-16,16-dimethylestr-4-en-3-one
GB1141214A (en) New derivatives of proscillaridin a
ES338729A1 (en) Medicinal compositions which contain 15,16beta-methylene steroids of the 19 nor-androstane series
GB1361411A (en) 11beta-methyl-17alpha-propadienyl steroids
IL43236A (en) 15alpha,16alpha-methylene-19-nor-delta4-pregnene-3,20-diones
GB1324911A (en) Aminoesters of steroids
GB1297964A (en)
GB1167098A (en) Novel 1-Methyl-Oestrene Compounds
GB1268008A (en) ESTERS OF p-BYPHENYLYLACETIC ACID
GB1324612A (en) Epoxy estranes processes for their preparation and compositions incorporating them
GB1193366A (en) Gona-4,9,11-Trienes, Process for their Preparation, and Compositions Incorporating them
GB1348943A (en) 5alpha-halo-6,6-difluoro-20-ketopregnanes
GB1189217A (en) 09-nor-Testosterone Phenoxyacetate and 6-Methyl Derivatives thereof
GB1184400A (en) Novel Androsteno-[3,2-c]-pyrazole Derivatives
GB1366080A (en) 6alpha,15alpha-dihydroxy-steroids
GB1243767A (en) Isoxazolidine derivatives and their method of preparation
GB1139873A (en) A novel 9-ß,10-‡-steroid
GB1183802A (en) Orally Effective Oestrogens
GB1193099A (en) Estratrienes, Processes for their Preparation, and Compositions Incorporating them
GB1504227A (en) Digoxin derivatives
GB1191347A (en) 03-Alkyl-10-Methylgon-4-En-3-Ones and their Derivatives

Legal Events

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