GB956271A - Improvements in or relating to the preparation of steroid compounds - Google Patents

Improvements in or relating to the preparation of steroid compounds

Info

Publication number
GB956271A
GB956271A GB2489459A GB2489459A GB956271A GB 956271 A GB956271 A GB 956271A GB 2489459 A GB2489459 A GB 2489459A GB 2489459 A GB2489459 A GB 2489459A GB 956271 A GB956271 A GB 956271A
Authority
GB
United Kingdom
Prior art keywords
methyl
hydroxy
acetoxy
keto
pregn
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
GB2489459A
Inventor
Gordon Hanley Phillipps
William Graham
Gordon Ian Gregory
Joseph Elks
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.)
Glaxo Group Ltd
Original Assignee
Glaxo Group 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
Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd
Priority to GB2489459A priority Critical patent/GB956271A/en
Priority to CH158865A priority patent/CH420142A/en
Priority to CH820560A priority patent/CH421097A/en
Priority to CH826560A priority patent/CH388949A/en
Priority to DE19601418855 priority patent/DE1418855A1/en
Priority to BE593214A priority patent/BE593214A/en
Priority to CH826660A priority patent/CH388950A/en
Priority to DE19601793670 priority patent/DE1793670A1/en
Priority to DE19601418857 priority patent/DE1418857C/en
Priority to BE593215A priority patent/BE593215A/en
Priority to BE593213A priority patent/BE593213A/en
Priority to DE19601418856 priority patent/DE1418856A1/en
Priority to SE360564A priority patent/SE314066B/xx
Publication of GB956271A publication Critical patent/GB956271A/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
    • A61K31/57—Compounds 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
    • A61K31/573—Compounds 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 substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • 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
    • A61K31/57—Compounds 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D81/00—Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents
    • B65D81/02—Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents specially adapted to protect contents from mechanical damage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical 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)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 3b -acetoxy -17a -hydroxy -16- methyl -5a - pregna-9(11), 15-dien -20- one, 3b , 17a -dihydroxy -16a - methyl -5a - pregn-9(11)-en -20- one and its 3-acetate, together with a process for the preparation of 16a -methyl -17a - hydroxy -20- keto -5a - steroids by subjecting a 16, 17-epoxy -16b - methyl -20-keto steroid of the 5a -series to rearrangement in a solvent medium in the presence of an acid catalyst to form a 17a -hydroxy -16- methylene-20-keto- or a 17a -hydroxy -16- methyl -D 15-20-keto-steroid, or a mixture thereof, which product is then hydrogenated in the presence of a palladium catalyst. The process is especially applicable to compounds of the general formula: <FORM:0956271/C2/1> in which R is hydrogen or acyl, X is keto, acyloxy, hydroxy or halogen, Y is hydrogen or halogen, or X and Y together signify a carbon-carbon double bond. The acid catalyst is preferably a strong acid, and the rearrangement is preferably effected in an ionising solvent medium, yielding mainly D 15 -16- methyl compounds which are hydrogenated over a palladium catalyst using neutral or basic conditions. Examples detail the conversion of 3b -acetoxy -16- methyl -5a - pregna-9(11): 16-dien -20- one into 3b -acetoxy -17a - hydroxy -16a - methyl -5a - pregn-9 (11)-en -20- one via the 16:17-oxide, the preparation of 3b -acetoxy -17a - hydroxy- -16- methylene -5a - pregnane-11, 20-dione, 3b -acetoxy-9a , 11b -dichloro -16- methylene -17a - hydroxy -5a -pregnan -20- one, and 3b , 17a -dihydroxy -16a -methyl -5a - pregn-9(11)-en -20- one. 16a -Methyl compounds may be freed from their 16b -methyl epimers by crystallisation or by preferential D-homoannulation of the b -epimer. Specifications 805,497, 956,272, 956,273 and 956,274 are referred to.
GB2489459A 1959-07-20 1959-07-20 Improvements in or relating to the preparation of steroid compounds Expired GB956271A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
GB2489459A GB956271A (en) 1959-07-20 1959-07-20 Improvements in or relating to the preparation of steroid compounds
CH158865A CH420142A (en) 1959-07-20 1960-07-19 Process for the preparation of 3B, 20-diacyloxy-9a, 11B-dichloro-17,20-epoxy-16-methyl-5a-pregnanes
CH820560A CH421097A (en) 1959-07-20 1960-07-19 Process for the preparation of 16-methyl steroids
CH826560A CH388949A (en) 1959-07-20 1960-07-20 Process for the preparation of 17a-hydroxy-16a-methyl-20-keto steroids of the 5a series
DE19601418855 DE1418855A1 (en) 1959-07-20 1960-07-20 Method of making steroids
BE593214A BE593214A (en) 1959-07-20 1960-07-20 Improvements in the preparation of steroid compounds
CH826660A CH388950A (en) 1959-07-20 1960-07-20 Process for the preparation of 17a-hydroxy-16-methyl-steroids of the 5a series
DE19601793670 DE1793670A1 (en) 1959-07-20 1960-07-20 Steroids and their method of manufacture
DE19601418857 DE1418857C (en) 1959-07-20 1960-07-20 Process for the production of 3beta-hydroxy- (or-acyloxy) -9alpha, llbeta-dichloro-lobeta-methyl-salphasteroids of the pregnane series
BE593215A BE593215A (en) 1959-07-20 1960-07-20 Improvements in the preparation of steroid compounds
BE593213A BE593213A (en) 1959-07-20 1960-07-20 Improvements in the preparation of steroid compounds
DE19601418856 DE1418856A1 (en) 1959-07-20 1960-07-20 Steroids and their method of manufacture
SE360564A SE314066B (en) 1959-07-20 1964-03-23

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2489459A GB956271A (en) 1959-07-20 1959-07-20 Improvements in or relating to the preparation of steroid compounds

Publications (1)

Publication Number Publication Date
GB956271A true GB956271A (en) 1964-04-22

Family

ID=10218935

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2489459A Expired GB956271A (en) 1959-07-20 1959-07-20 Improvements in or relating to the preparation of steroid compounds

Country Status (4)

Country Link
BE (2) BE593214A (en)
CH (2) CH388950A (en)
DE (3) DE1793670A1 (en)
GB (1) GB956271A (en)

Also Published As

Publication number Publication date
DE1793670A1 (en) 1972-03-16
CH388950A (en) 1965-03-15
DE1418856A1 (en) 1968-10-17
CH388949A (en) 1965-03-15
BE593214A (en) 1960-11-14
BE593215A (en) 1960-11-14
DE1418855A1 (en) 1968-10-03

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