GB843353A - Improvements in or relating to 6-methyl steroid compounds - Google Patents

Improvements in or relating to 6-methyl steroid compounds

Info

Publication number
GB843353A
GB843353A GB2616157A GB2616157A GB843353A GB 843353 A GB843353 A GB 843353A GB 2616157 A GB2616157 A GB 2616157A GB 2616157 A GB2616157 A GB 2616157A GB 843353 A GB843353 A GB 843353A
Authority
GB
United Kingdom
Prior art keywords
methyl
steroids
androstane
acyloxy
tetrol
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
GB2616157A
Inventor
Bernard Ellis
Betty Eunice Hill
Vladimir Petrow
David Morton Williamson
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.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals Ltd
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 NL110449D priority Critical patent/NL110449C/xx
Priority to NL231639D priority patent/NL231639A/xx
Application filed by BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB2616157A priority patent/GB843353A/en
Priority to CH6306458A priority patent/CH367493A/en
Priority to US760094A priority patent/US2965485A/en
Publication of GB843353A publication Critical patent/GB843353A/en
Expired legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/485—Direct positive emulsions
    • G03C1/48515—Direct positive emulsions prefogged
    • G03C1/48523—Direct positive emulsions prefogged characterised by the desensitiser
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups

Abstract

The invention comprises 6-methyl-3-oxo-4,6-dienic steroids of the androstane and pregnane series having apart from any substituent at the 17-position the general formula: <FORM:0843353/IV(b)/1> and the preparation thereof by reacting 3b -hydroxy or 3b -acyloxy-6-oxo-steroids of the androstane and pregnane series having apart from any substituent at the 17-position the general formula: <FORM:0843353/IV(b)/2> wherein R represents hydrogen or an acyl group, with a methyl magnesium halide such as the bromide or iodide, to form 6b -methyl-3b ,5 a ,6-trihydroxy steroids of the androstane and pregnane series having apart from any substituent at the 17-position of the general formula: <FORM:0843353/IV(b)/3> oxidising the 3b , 5 a ,6-trihydroxy-steroids e.g. with chromium trioxide in acetic acid or pyridine, to the corresponding 5 a ,6-dihydroxy-6-methyl-3-oxo-steroids of the androstane and pregnane series having from any substituent at the 17-position the general formula: <FORM:0843353/IV(b)/4> and dehydrating the 5 a ,6-dihydroxy-6-methyl-3-oxo steroids with a source of hydrogen ions e.g. hydrogen chloride. The process may be applied to a 3b -acyloxy-5 a -hydroxyandrostan-6-one which may be additionally substituted at C17 by hydroxyl with or without alkyl, alkenyl or alkynyl groups containing not more than 5 carbon atoms, and 3b -acyloxy-5 a -hydroxypregnan-6-one which may be additionally substituted by an acyloxy or hydroxy group at C20 with or without acyloxy or alkyl groups containing not more than 5 carbon atoms at C17 or C21. In the example the following intermediate and final products are prepared by the above methods:-17 a -ethynyl-6-methylandrostane-3b ,5 a ,6,17b -tetrol, 17 a -ethynyl-6-methyl-androstane-5 a ,6,17b -triol-3-one, and 17 a -ethynyl-17b -hydroxy-6-methylandrosta-4,6-dien-3-one; 6-methylpregnane-3b 5 a ,6,20-tetrol, 6-methylpregnane-5 a ,6-diol-3,20 -dione and 6-methylpregna-4,6-diene-3,20-dione; 6,17 a -dimethylandrostane-3b ,5 a ,6,17b -tetrol, 6,17 a - dimethylandrostane - 5 a ,6,17b - triol - 3 - one, and 6,17 a - dimethyl - 17b - hydroxyandrosta-4,6-dien-3-one; and 6-methylandrostane - 3b ,5 a ,6,17b - tetrol, 5 a ,6 - dihydroxy - 6 - methylandrostane - 3,17 - dione and 6 - methylandrosta-4,6-diene-3,17-dione.
GB2616157A 1957-08-19 1957-08-19 Improvements in or relating to 6-methyl steroid compounds Expired GB843353A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL110449D NL110449C (en) 1957-08-19
NL231639D NL231639A (en) 1957-08-19
GB2616157A GB843353A (en) 1957-08-19 1957-08-19 Improvements in or relating to 6-methyl steroid compounds
CH6306458A CH367493A (en) 1957-08-19 1958-08-19 Process for the preparation of 6-methyl-3-oxo-4,6 steroids
US760094A US2965485A (en) 1957-08-19 1958-09-10 Photographic desensitising compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2616157A GB843353A (en) 1957-08-19 1957-08-19 Improvements in or relating to 6-methyl steroid compounds

Publications (1)

Publication Number Publication Date
GB843353A true GB843353A (en) 1960-08-04

Family

ID=10239320

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2616157A Expired GB843353A (en) 1957-08-19 1957-08-19 Improvements in or relating to 6-methyl steroid compounds

Country Status (1)

Country Link
GB (1) GB843353A (en)

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