GB1019576A - Synthesis of steroids - Google Patents

Synthesis of steroids

Info

Publication number
GB1019576A
GB1019576A GB29387/62A GB2938762A GB1019576A GB 1019576 A GB1019576 A GB 1019576A GB 29387/62 A GB29387/62 A GB 29387/62A GB 2938762 A GB2938762 A GB 2938762A GB 1019576 A GB1019576 A GB 1019576A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
acyloxy
hydrogen
keto
steroids
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
GB29387/62A
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.)
Olin Corp
Original Assignee
Olin Corp
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 claimed from US183014A external-priority patent/US3153038A/en
Application filed by Olin Corp filed Critical Olin Corp
Publication of GB1019576A publication Critical patent/GB1019576A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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
    • 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
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
    • 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
    • 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 a D 7-, D 7 9(11') or D 8-steriod of the general formula <FORM:1019576/C2/1> whereid Y represents oxo or x-or b -hydroxy or acyloxy, X represents oxo, acyloxy, hydroxy or hydrogen and Z represents hydroxy or acyloxy, X being oxo or hydrogen when Y is oxo, and when Y is hydroxy or acyloxy, X is acyloxy or hydrogen and the preparation thereof by treata steroid of the formula <FORM:1019576/C2/2> wherein X and Y have the above significance and B represents hydrogen or lower alkyl, with lithium aluminium hydride, treating the result ing corresponding D 7,20(22),23 - lanostatriene D 8,20(22)23, - lanostatriene or D 7,9(11),20(22)23, lano-statetraene with ozone, and reducing the result ing ozonide with zinc dust and glacial acetic acid and, if desired, forming an ester and/or oxi dizing a 3-hydroxy group and optionally a 16-hydroxy group to form a 3-keto or 3,16-diketo compound. Pharmaceutical compositions useful in the treatment of Addison's disease contain steroids of the first general formula above and a suitable pharmaceutical carrier. Steroids of the first general formula above, wherein X and Y have the significance indicated and Z represents hydrogen, are prepared by treating compounds of said general formula, wherein Y represents keto or acyloxy and Z represents hydroxy, with an organo-sulphonyl chloride to form the corresponding 21-organo-sulphonate ester, treating these compounds with an alkali metal iodide to form the corresponding 21-iodo compounds, and reducing these com pounds, for example with sodium bisulphite. If a product containing a 3b -hydroxy or acyloxy group is formed, it can be oxidized to the corresponding 3-keto compound after saponi fication of any 3-ester group. Steroids of the second general formula above wherein B, X and Y have the above significance, are prepared by treating the corresponding steroids having at ring D the formula <FORM:1019576/C2/3> wherein the symbols R may be the same or different and are hydrogen or alkyl and the symbols R1 may be the same or different and are hydrogen or hydroxy, such as eburicoic, poly-porenic, tumulosic, pinicolic, elemolic, elemonic, dehydroeburicoic, dehydroelemonic and de hydroelemolic acids (if necessary after acylating any 3-hydroxy group) with ozone and reducing the resulting ozonide to form the corresponding 24 - keto - 21 - carboxylic - compound, for ex ample, of the formula <FORM:1019576/C2/4> wherein R11 represents an acetyl group (which may also be obtained by treating said steroids having the ring D formula with a hydroxylating agent such as osmium tetroxide and then cleaving the glycol, for example of the formula <FORM:1019576/C2/5> wherein R11 represents an acetyl group), lactonizing the above 24-keto-21-carboxylic-lano stane compounds to form a mixture of steroid a - and b -lactones, for example of the general formulae <FORM:1019576/C2/6> wherein R11 has the previous significance, and dehydrogenating these compounds, for ex ample by treatment with palladium on charcoal. A resulting 3-ester may be saponified to 3-hydroxy and then oxidized to 3-keto.
GB29387/62A 1961-08-18 1962-07-31 Synthesis of steroids Expired GB1019576A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13231061A 1961-08-18 1961-08-18
US183014A US3153038A (en) 1962-03-28 1962-03-28 Triterpenoid acid derivatives

Publications (1)

Publication Number Publication Date
GB1019576A true GB1019576A (en) 1966-02-09

Family

ID=26830254

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29387/62A Expired GB1019576A (en) 1961-08-18 1962-07-31 Synthesis of steroids

Country Status (2)

Country Link
FR (1) FR2879M (en)
GB (1) GB1019576A (en)

Also Published As

Publication number Publication date
FR2879M (en) 1964-11-02

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