GB946658A - 18:20-di-oxygenated pregnanes and process for their manufacture - Google Patents

18:20-di-oxygenated pregnanes and process for their manufacture

Info

Publication number
GB946658A
GB946658A GB511160A GB511160A GB946658A GB 946658 A GB946658 A GB 946658A GB 511160 A GB511160 A GB 511160A GB 511160 A GB511160 A GB 511160A GB 946658 A GB946658 A GB 946658A
Authority
GB
United Kingdom
Prior art keywords
pregnane
acid
lactone
keto
acetoxy
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
GB511160A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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
Priority claimed from CH6947559A external-priority patent/CH383953A/en
Priority claimed from CH8178059A external-priority patent/CH407111A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB946658A publication Critical patent/GB946658A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises (1) a process for the preparation of 18, 20-dioxygenated pregnanes, wherein an 18, 20-oxido-pregnane is treated with a strong oxidizing agent and, if desired, the resulting 18, 20-lactone of a 20-keto-pregnane-18-acid and/or 20, 18-lactone of an 18-hydroxyetianic acid is/are reduced with a complex light metal hydride to form an 18, 20-dihydroxy-pregnane and/or -21-nor-pregnane, respectively, or the resulting 18, 20-lactone of a 20-ketopregnane-18-acid is dehydrated to form an 18, 20-lactone of a D 20-20-hydroxy-pregnane-18-acid; and (2) a new classes of steroids, the 18, 20-lactones of saturated or unsaturated 11-unsubstituted 20-keto-pregnane-18-acids and the 18, 20-lactones of D 20-20-hydroxy-pregnene-18-acids unsubstituted in the 11-position or substituted in the 11-position by a free or esterified a -hydroxyl group or a keto group. Chromium trioxide in acetic or propionic acid may be used as oxidizing agent in the present process, the starting materials for which may be 5a - or 5b -pregnanes which may contain further substituents i.e. free, esterified or etherified hydroxyl groups, free or ketalized oxo groups, alkyl groups or halogen atoms or double bonds in the ring system. Free hydroxyl groups are converted to oxo groups during the oxidation process. Products containing no 11-substituent may be converted, preferably after formation of the D 4-3-keto grouping, into 11-oxygenated compounds with the aid of microorganisms. In Examples (1) and (2) 3b -acetoxy-18, 20b -oxido-5a -pregnene is oxidized to the lactone of 3b -acetoxy-18-hydroxy-5a -etianic acid (which on reduction gives 3b , 18, 20b -trihydroxy-5a -21-nor-pregnane) and the 18 20-lactone of 3b -acetoxy-20-keto-5a -pregnane-18-acid (which on reduction gives 3b , 18, 20-trihydroxy-5a -pregnane); and 3, 11-diketo-18, 20-trihydroxy-5b -pregnane is oxidized to the 18, 20-lactone of 3, 11, 20-triketo-5b -pregnane-18-acid, which on dehydration gives the 18, 20-lactone of D 20-3 b -acetoxy-20-hydroxy-5a -pregnene-18-acid. Specifications 946,656, 946,657, 946,659 and 946,660 are referred to.
GB511160A 1959-02-12 1960-02-12 18:20-di-oxygenated pregnanes and process for their manufacture Expired GB946658A (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
CH6947559A CH383953A (en) 1959-02-12 1959-02-12 Process for the preparation of 18,20-oxido-steroids
CH7244359 1959-04-23
CH7375459 1959-05-29
CH8178059A CH407111A (en) 1959-12-11 1959-12-11 Process for the production of new hydroxyaldehydes of the Pregnan range
CH8223159 1959-12-22
CH8223259 1959-12-22
CH8223359 1959-12-22

Publications (1)

Publication Number Publication Date
GB946658A true GB946658A (en) 1964-01-15

Family

ID=31721947

Family Applications (1)

Application Number Title Priority Date Filing Date
GB511160A Expired GB946658A (en) 1959-02-12 1960-02-12 18:20-di-oxygenated pregnanes and process for their manufacture

Country Status (1)

Country Link
GB (1) GB946658A (en)

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