GB1313583A - Process for the manufacture of 21-acyloxy-3beta-17alpha-dihydroxy- 5-pregnen-20-ones - Google Patents

Process for the manufacture of 21-acyloxy-3beta-17alpha-dihydroxy- 5-pregnen-20-ones

Info

Publication number
GB1313583A
GB1313583A GB1919570A GB1919570A GB1313583A GB 1313583 A GB1313583 A GB 1313583A GB 1919570 A GB1919570 A GB 1919570A GB 1919570 A GB1919570 A GB 1919570A GB 1313583 A GB1313583 A GB 1313583A
Authority
GB
United Kingdom
Prior art keywords
treating
dihydroxy
resulting
pregnen
acyloxy
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
GB1919570A
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.)
Novartis AG
Original Assignee
Ciba Geigy 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
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1313583A publication Critical patent/GB1313583A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Abstract

1313583 Preparation of 21-acyloxy-3,17- dihydroxy-5-pregnen-20-ones CIBA-GEIGY AG 22 April 1970 [22 April 1969] 19195/70 Heading C2U A steroid of the formula wherein R 2 is H 2 , alkylidene, H(α-or #-alkyl) or H(α-OR<SP>1</SP>) in which OR<SP>1</SP> is free, esterified or etherified OH; R 3 is OH, or R 2 and R 3 together are α,α-methylenedioxy mono- or di-substituted by optionally substituted hydrocarbon radicals, and R 4 is carboxylic acyl, is prepared by oxidizing with a per-acid a steroid of the formula (wherein R 2 is as above, R 1 is an esterified beta-hydroxyl group and Ac is a C 1-7 alkanoyl radical), treating the reaction product with an alkaline reagent, treating the resulting 3#,17α- dihydroxy-5#,6#-oxido-20-keto-pregnane with a hydrohalic acid and then with bromine, treating the resulting 21-bromo compound with an alkali metal salt of a carboxylic acid, and then treating the resulting 5#,6#-oxido-17α- hydroxy-20-keto-21-acyloxypregnane, if desired after ketalizing any 16α,17α-diol group present, with at least 2 molar equivalents of hydrogen iodide. The treatment with HI is preferably effected at 35‹C. or below in an inert solvent using 6-8 molar equivalents of HI in the form of an aqueous solution of about 55% strength, and after the treatment a reducing agent, e.g. sodium bisulphite, is desirably added to reduce the iodine formed. The process and the preparation of the starting material is illustrated as follows:-
GB1919570A 1969-04-22 1970-04-22 Process for the manufacture of 21-acyloxy-3beta-17alpha-dihydroxy- 5-pregnen-20-ones Expired GB1313583A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US81839269A 1969-04-22 1969-04-22

Publications (1)

Publication Number Publication Date
GB1313583A true GB1313583A (en) 1973-04-11

Family

ID=25225441

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1919570A Expired GB1313583A (en) 1969-04-22 1970-04-22 Process for the manufacture of 21-acyloxy-3beta-17alpha-dihydroxy- 5-pregnen-20-ones

Country Status (8)

Country Link
JP (1) JPS5028954B1 (en)
CH (1) CH555818A (en)
DE (1) DE2018730A1 (en)
FR (1) FR2042356B1 (en)
GB (1) GB1313583A (en)
HU (1) HU163232B (en)
NL (1) NL7005130A (en)
PL (1) PL80620B1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58177689A (en) * 1982-04-13 1983-10-18 松下電器産業株式会社 Electric dryer

Also Published As

Publication number Publication date
CH555818A (en) 1974-11-15
FR2042356B1 (en) 1973-12-21
DE2018730A1 (en) 1970-11-05
HU163232B (en) 1973-07-28
NL7005130A (en) 1970-10-26
PL80620B1 (en) 1975-08-30
JPS5028954B1 (en) 1975-09-19
FR2042356A1 (en) 1971-02-12

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees