GB1246751A - Improvements in or relating to estrogen steroid ethers - Google Patents

Improvements in or relating to estrogen steroid ethers

Info

Publication number
GB1246751A
GB1246751A GB2510569A GB2510569A GB1246751A GB 1246751 A GB1246751 A GB 1246751A GB 2510569 A GB2510569 A GB 2510569A GB 2510569 A GB2510569 A GB 2510569A GB 1246751 A GB1246751 A GB 1246751A
Authority
GB
United Kingdom
Prior art keywords
ols
ones
prepared
proceeds via
ethers
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
GB2510569A
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.)
Roche Palo Alto LLC
Original Assignee
Roche Palo Alto LLC
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 Roche Palo Alto LLC filed Critical Roche Palo Alto LLC
Publication of GB1246751A publication Critical patent/GB1246751A/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
    • 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
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • 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
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)

Abstract

1,246,751. Ethers of estrogenic steroids. SYNTEX CORP. 16 May, 1969 [22 May, 1968; 9 Oct., 1968], No. 25105/69. Headings C2C and C2U. Novel #<SP>1,3,5(10)</SP>-estratrienes containing at least one 4<SP>1</SP>-(C 1-6 alkoxy)tetrahydropyran-4<SP>1</SP>- yloxy or 5<SP>1</SP>,6<SP>1</SP> - dihydro - 2H - pyran 4<SP>1</SP>- yloxy group attached to the steroid nucleus i.e. positions 1 to 17, and optionally containing other substituents and/or double bonds are prepared by reacting in the presence of a catalyst the corresponding free ols with an excess of a 4<SP>1</SP> - (C 1-6 alkoxy) - 5<SP>1</SP>,6<SP>1</SP> - dihydro - 2H- pyran. Both types of ether are formed, and they are separated by chromatography. In the products, esterified OH groups may be hydrolysed, 17-ones may be converted to 17α-R 1 - 17#-ols (R 1 is H or an aliphatic hydrocarbyl or halohydrocarbyl radical), free OH groups may be esterified or etherified, and a 17α-ethynyl group may be converted to a 17α-(2<SP>11</SP>,2<SP>11</SP>-difluorocyclopropenyl) group. Starting materials of the Formulae (D) and (E) below are prepared from precursors of the formula (C) as indicated, the precursors being prepared from reactants (A) and (B) as indicated wherein R 1 is H, CH 3 , OCH 3 , OH or O acyl, R 2 is H or CH 3 ; and R 6 is CH 3 or C 2 H 5 . The preparation of compounds (C) proceeds via 2-R 6 -2- (1,2,3,4 - tetrahydro - 6 - methoxy - 3 - R 2 - 8 - R 1 - naph - 1 - ylidenethyl) - cyclopenta - 1,3 - diones and 3 - methoxy - 13 - R 6 - 1 - R 1 - 7 - R 2 - estra- 1,3,5(10),8,14 - pentaen - 17 - ones, which lastnamed are catalytically hydrogenated to give the corresponding 1,3,5(10),8 - tetraen - 17 - ones and these reduced to give (C). The process (C) -> (D) proceeds via the estratrien-17#-ols, and the process (C) -> (E) proceeds via the 8,9 - oxido - 1,3,5(10) - trienes, the 8α - hydroxy- 1,3,5(10),9(11) - tetraenes, the 8α - hydroxy- 1,3,5(10) - trienes, 17 - mesylates of the 1,3,5 (10),7 - tetraenes, the corresponding 17 - ols and the corresponding 3,17-diols. The steroid ethers of the invention are stated to possess anti-fertility and estrogenic activity, and they may be made up into pharmaceutical compositions with suitable carriers.
GB2510569A 1968-05-22 1969-05-16 Improvements in or relating to estrogen steroid ethers Expired GB1246751A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US73130168A 1968-05-22 1968-05-22
US76630668A 1968-10-09 1968-10-09

Publications (1)

Publication Number Publication Date
GB1246751A true GB1246751A (en) 1971-09-22

Family

ID=27112205

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2510569A Expired GB1246751A (en) 1968-05-22 1969-05-16 Improvements in or relating to estrogen steroid ethers

Country Status (5)

Country Link
ES (1) ES367520A1 (en)
FR (1) FR2009101A1 (en)
GB (1) GB1246751A (en)
NL (1) NL6907790A (en)
SE (1) SE356510B (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3134771A (en) * 1962-05-12 1964-05-26 Ormonoterapia Richter Spa 3-tetrahydropyranyl ethers of estra-1,3,5(10)-trienes
NL128376C (en) * 1964-04-23

Also Published As

Publication number Publication date
DE1926043B2 (en) 1976-01-22
SE356510B (en) 1973-05-28
NL6907790A (en) 1969-11-25
FR2009101A1 (en) 1970-01-30
ES367520A1 (en) 1971-06-16
DE1926043A1 (en) 1969-11-27

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