GB928226A - Steroid compounds - Google Patents

Steroid compounds

Info

Publication number
GB928226A
GB928226A GB2657159A GB2657159A GB928226A GB 928226 A GB928226 A GB 928226A GB 2657159 A GB2657159 A GB 2657159A GB 2657159 A GB2657159 A GB 2657159A GB 928226 A GB928226 A GB 928226A
Authority
GB
United Kingdom
Prior art keywords
alkyl
dichloro
oxo
acyloxy
reacting
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
GB2657159A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 US759116A external-priority patent/US3068228A/en
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB928226A publication Critical patent/GB928226A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 3b -acyloxy-16a -alkyl-5,6-dichloro- 20-ketopregnanes; 16a -alkyl-5, 6-dichloro- 3b -hydroxy- 20-oxo-pregnane-21-glyoxylic acids and alkyl esters thereof; 3b ,23- diacyloxy- 16a -alkyl- 5,6-dichloro-21-normethyl- 17(20), 22-choladieno-24-(20)-lactones; and 3b ,23-diacyloxy-16a -alkyl-5,6-dichloro- 21-normethyl- 17(20) -oxido- 22-choleno-24(20)-lactones; and processes for the preparation of 3b -acyloxy-16a -alkyl-5,6-dichloro-20-oxo pregnanes by reacting 3b -acyloxy-16a -alkyl-20-oxo-5(6)-pregnenes with chlorine, for the preparation of alkyl esters of 16a -alkyl-5,6-dichloro- 3b -hydroxy-20-oxo-21-glyoxylic acid by reacting 3b -acyloxy-16a -alkyl-5,6-dichloro-20-oxo-pregnanes with dialkyl oxalates, for the preparation of 16a -alkyl- 5,6-dichloro- 3b -hydroxy- 20-oxo- 21-glyoxylic acids by hydrolysing the corresponding alkyl esters with alkali metal hydroxides, for the preparation of 3,23-diacyloxy- 16a -alkyl- 5,6-dichloro- 21-normethyl-17 (20),22-choladieno-24(20)-lactones by reacting 16a -alkyl-5,6-dichloro- 3b -hydroxy-20-oxo-pregnane-21-glyoxylic acids with a strong acid such as 2,4-dinitrobenzenesulphonic or perchloric acid, and acyl anhydride, for the preparation of 3b ,23-diacyloxy-16a -alkyl-5,6-dichloro- 21-normethyl- 17(20) -oxido-22-choleno-24(20)-lactones by reacting 3b ,23-diacyloxy-16a -alkyl- 5,6-dichloro-21-normethyl-17(20), 22-choladieno-24(20)-lactones with percarboxylic acids, and for the preparation of 16a -alkyl-17a -hydroxy- 21-acyloxy-3,20-dioxo-4-pregnenes by reacting 3b ,23-diacyloxy-16a -alkyl-5,6-dichloro- 21-normethyl-17(20) -oxido-22-choleno-24(20)-lactones with a base to form 16a -alkyl-5,6-dichloro-3b ,17a -dihydroxy-20-oxo-pregnanes, brominating these compounds to form 16a -alkyl-5,6-dichloro-3b , 17a -dihydroxy- 20-oxo-21-bromopregnanes, reacting these compounds with a salt of an organic acid to form 16a -alkyl-5,6-dichloro-3b , 17a -dihydroxy- 21-acyloxy- 20-keto-pregnanes, and oxidising these compounds to form 16a -alkyl-5,6-dichloro- 17a -hydroxy-21-acyloxy-3, 20-dioxopregnanes, and reacting these compounds with a chromous halide. 3b -Acyloxy- 16a -alkyl- 20-oxo- 5(6)-pregnenes are prepared by reacting 3b -acyloxy-20-oxo-5(6),16-pregnadienes with alkyl magnesium halides to form 16a -alkyl-3b -hydroxy-20-oxo-5(6)-pregnanes, and acylating these compounds with acyl anhydrides in the presence of pyridine.
GB2657159A 1958-08-11 1959-08-04 Steroid compounds Expired GB928226A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US75418158A 1958-08-11 1958-08-11
US759116A US3068228A (en) 1958-09-05 1958-09-05 16alpha-lower alkyl pregnane and choleno derivatives

Publications (1)

Publication Number Publication Date
GB928226A true GB928226A (en) 1963-06-12

Family

ID=27115884

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2657159A Expired GB928226A (en) 1958-08-11 1959-08-04 Steroid compounds

Country Status (4)

Country Link
BE (1) BE581499A (en)
CH (1) CH389601A (en)
ES (1) ES251602A1 (en)
GB (1) GB928226A (en)

Also Published As

Publication number Publication date
BE581499A (en) 1960-02-08
CH389601A (en) 1965-03-31
ES251602A1 (en) 1960-01-01

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