GB1051613A - - Google Patents
Info
- Publication number
- GB1051613A GB1051613A GB1051613DA GB1051613A GB 1051613 A GB1051613 A GB 1051613A GB 1051613D A GB1051613D A GB 1051613DA GB 1051613 A GB1051613 A GB 1051613A
- Authority
- GB
- United Kingdom
- Prior art keywords
- give
- hydrogen
- compound
- ols
- methyl
- 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.)
- Active
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
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- 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
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- 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
1,051,613. 19-Alkyl-steroids. SYNTEX CORPORATION. July 17, 1963, No. 28279/63. Heading C2U. Novel steroids of the formulµ (wherein X is C 1-8 alkyl ; W is a double bond or a saturated linkage between C-1 and C-2; Z is hydrogen, α- or #-methyl, α- or #-fluorine, or α- or #-chlorine; Q is #-OH or keto ; Y is hydrogen, fluorine or chlorine; R is hydroxyl; T is hydrogen, α-hydroxy or -acyloxy derived from a hydrocarbon carboxylic acid of less than 12 carbon atoms which is optionally substituted, or α- or #-methyl; or R and T together are α, α-di- (C 1-8 alkyl)-methylenedioxy; and R<SP>1</SP> is hydrogen or acyl as above defined) are prepared from the corresponding 11 -unsubstituted-21 -unsubstituted steroids via the 21-iodo compounds and 21-acetates using standard procedures, the formed 11-unsubstituted 21-ols then being incubated with adrenal glands to give the 11#-ols, which on oxidation after esterification of the 21- hydroxy group give the 11-ones. Alternatively the 6-substituents and #<SP>1</SP> and #<SP>6</SP> double bonds may be introduced into the molecule after the 21-hydroxylation but before the 11#-hydroxylation. For example, the 21-acetate is converted to the 3,20-bis-ketal, this is converted to the 5α, 6α-oxido compound and this is reacted with methyl magnesium bromide and then thionyl chloride to give the 6#-methyl compound (which can be epimerized with alkali to the 6α-methyl compound), or with hydrogen chloride to give the 6α-chloro compound, or with hydrogen fluoride and then hydrogen chloride to give the 6α-fluoro compound. Alternatively, the 21- acetate can be converted to the #<SP>3,5</SP>-3-ethyl enol ether and this treated with an N-chloroamide or -imide to give the 6#-chloro compound or with perchloryl fluoride to give the 6#-fluoro compound. The 9-substituent is introduced into the 11#-ols by conversion to the #<SP>9(11)</SP>-compounds, reaction of these with an N-bromoamide or -imide to give the 9α-bromo-11#-ols, conversion of these to the 9#,11#-oxido compounds, and reaction of these with a hydrogen halide, the 21-hydroxy group being esterified throughout. The products may be oxidized to the 11-ones. #<SP>6</SP>- and #<SP>1</SP>-double bonds are introduced into the 21-acylates by standard procedures. 16α, 17α-ketonides may be hydrolysed to the 16α,17α-diols which may be converted to the 16-acylates. 21-Acylates may be saponified and the free 21-ols re-acylated. The steroids of the invention, which are stated to have anti-inflammatory, anti-androgenic, anti-gonadotrophic and anti-estrogenic properties, may be made up into pharmaceutical compositions with suitable carriers.
Publications (1)
Publication Number | Publication Date |
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GB1051613A true GB1051613A (en) |
Family
ID=1756499
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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GB1051613D Active GB1051613A (en) |
Country Status (1)
Country | Link |
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GB (1) | GB1051613A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015063408A2 (en) | 2013-10-28 | 2015-05-07 | Sanofi | Method for preparing steroidal derivatives |
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0
- GB GB1051613D patent/GB1051613A/en active Active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015063408A2 (en) | 2013-10-28 | 2015-05-07 | Sanofi | Method for preparing steroidal derivatives |
US9783569B2 (en) | 2013-10-28 | 2017-10-10 | Sanofi | Method for preparing 6-alkylated steroidal derivatives and corresponding alkylated 5,6,7,8-tetrahydronaphthalene-2(4 alpha.H)-ones |
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