GB790452A - Steroids and the preparation thereof - Google Patents

Steroids and the preparation thereof

Info

Publication number
GB790452A
GB790452A GB816956A GB816956A GB790452A GB 790452 A GB790452 A GB 790452A GB 816956 A GB816956 A GB 816956A GB 816956 A GB816956 A GB 816956A GB 790452 A GB790452 A GB 790452A
Authority
GB
United Kingdom
Prior art keywords
11a
hydroxy
acetoxy
11b
dione
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
GB816956A
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.)
Upjohn Co
Original Assignee
Upjohn Co
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 to US790452XA priority Critical
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB790452A publication Critical patent/GB790452A/en
Application status is Expired legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes for the preparation of steroids in general

Abstract

A D 9(11)-steroid is obtained by contacting, under anhydrous conditions, a steroid 11-hypohalite having a hydrogen atom at each of carbon atoms 9 and 11 and wherein the halogen is chlorine, bromine or iodine, with anhydrous sulphur dioxide in the presence of a basic organic compound substantially unaffected by the hypohalite and sulphur dioxide. As basic organic compounds there may be used pyridine, picoline, lutidine, collidine, conyrine, parvuline, formamide, methylformamide and dimethylformamide. The 11-hypohalite is prepared by the reaction of an N-haloamide or N-haloimide under anhydrous conditions in the presence of a base with an 11-hydroxy steroid. As N-haloamide or N-haloimide there may be used N-chloracetamide, N-bromacetamide, N-chlorosuccimide, N-bromosuccimide, N-iodosuccinimide, N-bromophthalimide, 3-bromo-5,5-dimethyl hydantoin or 1,3-dibromo-5,5-dimethyl hydantoin. Examples describe the dehydration of hydrocortisone acetate to produce 17a -hydroxy - 21 - acetoxy - 4,9(11) - pregnadiene-3,20-dione using (1) pyridine, N-bromoacetamide and anhydrous sulphur dioxide; (2) 1,3-dibromo-5,5-dimethylhydantoin instead of N-bromoacetamide; (3) N-chloro-succimide instead of N-bromoacetamide; (4) N-iodo succinimide instead of N-bromoacetamide; (5) lutidine instead of pyridine; (6) sodium hyposulphite instead of SO2; (7) exposing the reaction to the light of a tungsten filament lamp; (8) dimethyl formamide instead of pyridine; (9) a reaction solvent comprising pyridine and acetone, ethyl acetate, ethylene dichloride, acetonitrile, benzene or nitrobenzene. Also described are the dehydration of 11a -hydroxyprogesterone, 11b -hydroxyprogesterone, 11a ,17a - dihydroxy - 21-acetoxy - 4 - pregnene - 3,20 - dione, 6b ,11a - dihydroxyprogesterone, 11a - hydroxy - 4-androstene - 3,17 - dione, 11b - hydroxy - 4-androstene - 3,7 - dione, 11b - hydroxy - 17a -acetoxy - 4 - androstene - 3 - one, 3b - acetoxy-11b - hydroxy - 5 - androstene - 17 - one, 3b -acetoxy - 11b - hydroxyandrostane - 17 - one, 11a and b - hydroxypregnane - 3,20 - dione, 3a - acetoxy - 11(a and b ) - hydroxy pregnane-20 - one, 11(a and b ), 17 - dihydroxyprogesterone, 11(a and b ), 21 - dihydroxyprogesterone, 11(a and b ) - hydroxy - 21 - acetoxyprogesterone, 2 - methyl - 11b ,17a - dihydroxy-21 - acetoxyprogesterone, 11b ,17a - dihydroxy-21 - acetoxy - 1,4 - pregnadiene - 3,20 - dione, 11a - hydroxystigmastadienone, 11a - hydroxysitostenone, 11a - hydroxyergosterol, 11a - hydroxycholestenone, 11a -hydroxybisnorcholanic acid, methyl 3 - keto - 11a - hydroxy - 4,17(20)-pregnadiene - 21 - oate and 11a - hydroxyetiocholenic acid.
GB816956A 1955-04-01 1956-03-15 Steroids and the preparation thereof Expired GB790452A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US790452XA true 1955-04-01 1955-04-01

Publications (1)

Publication Number Publication Date
GB790452A true GB790452A (en) 1958-02-12

Family

ID=22148070

Family Applications (1)

Application Number Title Priority Date Filing Date
GB816956A Expired GB790452A (en) 1955-04-01 1956-03-15 Steroids and the preparation thereof

Country Status (1)

Country Link
GB (1) GB790452A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0614463B1 (en) * 1991-11-22 2003-02-12 Alcon Laboratories, Inc. Angiostatic steroids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0614463B1 (en) * 1991-11-22 2003-02-12 Alcon Laboratories, Inc. Angiostatic steroids

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