GB1017431A - 17ª‰-acetoacetoxy steroids and process for the preparation thereof - Google Patents

17ª‰-acetoacetoxy steroids and process for the preparation thereof

Info

Publication number
GB1017431A
GB1017431A GB4721663A GB4721663A GB1017431A GB 1017431 A GB1017431 A GB 1017431A GB 4721663 A GB4721663 A GB 4721663A GB 4721663 A GB4721663 A GB 4721663A GB 1017431 A GB1017431 A GB 1017431A
Authority
GB
United Kingdom
Prior art keywords
steroids
groups
alkyl
acetoacetoxy
ones
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
GB4721663A
Inventor
Colin Michael Burgess
Peter Feather
Vladimir Petrow
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.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals Ltd
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
Priority to BE656362D priority Critical patent/BE656362A/xx
Application filed by BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB4721663A priority patent/GB1017431A/en
Priority to BR16484264A priority patent/BR6464842D0/en
Priority to CH1536764A priority patent/CH457418A/en
Priority to DEB79533A priority patent/DE1274125B/en
Priority to NL6413823A priority patent/NL6413823A/xx
Publication of GB1017431A publication Critical patent/GB1017431A/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
    • 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
    • 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)
  • 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

The invention comprises 17b -acetoacetoxysteroids having in ring D of the steroid nucleus the structure <FORM:1017431/C2/1> (wherein R is H, a halogen, CF3, C­CH or C1-5 alkyl) and their preparation by reacting the corresponding 17b - hydroxy - steroids with diketene in an anhydrous non-hydroxylic solvent in the presence of an organic base catalyst. The process may be applied to steroids containing a variety of substituents and unsaturated links in rings A, B, and C, e.g. to steroids containing D 1-, D 2-, D 3-, D 4-, D 5-, D 9(11)-, D 11-, D 2,5(10), D 3,5-, D 1,3,5(10)- or D 4,9(10)-double bonds; alkyl, alkenyl or alkynyl groups, particularly 2-, 4- and 6-methyl; free or protected, e.g. as enol ethers, enamines, ketals or thioketals, oxo groups, particularly at positions 3, 4, 6 and 11; acyl groups, particularly at position 3; and protected hydroxy groups, e.g. tetrahydropyranyl-oxy, -ethoxy or -acyloxy groups. Examples are given, D 2,5(10) - 3 - alkoxy products being converted to 19-nor-D 4-3-ones or D 5(10)-3-ones. 3b - acetoxy - 17a - chlorethynyl - androst - 5 - en-17b -ol is prepared by acetylation of the 3b -ol. 17a - butadiynyl - 3 - methoxy - oestra - 1,3,5-(10)-trien-17b -o is prepared from oestrone 3-methyl ether and 1,4-dichloro-but-2-yne with sodium in liquid ammonia. Specifications 915,565 and 961,502 are referred to.ALSO:Pharmaceutical compositions comprise 17b -acetoacetoxy-steroids having in ring D of the steroids nucleus the structure <FORM:1017431/A5-A6/1> (wherein R is H, a halogen, CF3, C ­ CH or C1-5 alkyl) and carriers. They may also contain ethynyloestradiol. Tablets are described, containing 17b -acetoacetoxy-17a -ethynyl-19-norandrost-4-en-3-one. Oily solutions are also mentioned. The steroids have, inter alia, oestrogenic, progestational, claudogenic and ovulation-inhibiting properties.
GB4721663A 1963-11-29 1963-11-29 17ª‰-acetoacetoxy steroids and process for the preparation thereof Expired GB1017431A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE656362D BE656362A (en) 1963-11-29
GB4721663A GB1017431A (en) 1963-11-29 1963-11-29 17ª‰-acetoacetoxy steroids and process for the preparation thereof
BR16484264A BR6464842D0 (en) 1963-11-29 1964-11-26 PROCESS TO PREPARE STEROIDS
CH1536764A CH457418A (en) 1963-11-29 1964-11-27 Process for the preparation of new 17B-acetoacetoxysteroids
DEB79533A DE1274125B (en) 1963-11-29 1964-11-27 Process for the preparation of optionally ring-substituted 17ª ‰ -acetoacetoxysteroids containing ring double bonds
NL6413823A NL6413823A (en) 1963-11-29 1964-11-27

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB4721663A GB1017431A (en) 1963-11-29 1963-11-29 17ª‰-acetoacetoxy steroids and process for the preparation thereof
GB4890863 1963-12-11

Publications (1)

Publication Number Publication Date
GB1017431A true GB1017431A (en) 1966-01-19

Family

ID=26266003

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4721663A Expired GB1017431A (en) 1963-11-29 1963-11-29 17ª‰-acetoacetoxy steroids and process for the preparation thereof

Country Status (6)

Country Link
BE (1) BE656362A (en)
BR (1) BR6464842D0 (en)
CH (1) CH457418A (en)
DE (1) DE1274125B (en)
GB (1) GB1017431A (en)
NL (1) NL6413823A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1364858A (en) * 1970-09-10 1974-08-29 Sandoz Ltd 17alpha-propadienyl-17beta-acetoacetoxy substituted steroids

Also Published As

Publication number Publication date
BR6464842D0 (en) 1973-08-02
DE1274125C2 (en) 1969-03-20
BE656362A (en)
NL6413823A (en) 1965-05-31
CH457418A (en) 1968-06-15
DE1274125B (en) 1968-08-01

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