GB898291A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Improvements in or relating to steroids and the manufacture thereof

Info

Publication number
GB898291A
GB898291A GB892260A GB892260A GB898291A GB 898291 A GB898291 A GB 898291A GB 892260 A GB892260 A GB 892260A GB 892260 A GB892260 A GB 892260A GB 898291 A GB898291 A GB 898291A
Authority
GB
United Kingdom
Prior art keywords
compound
dimethyl
pregnene
trihydroxy
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
GB892260A
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.)
Pharmacia and 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
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB898291A publication Critical patent/GB898291A/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

Abstract

The invention comprises compounds having the formulae <FORM:0898291/IV (b)/1> wherein R1 is hydrogen or the acyl radical of a hydrocarbon carboxylic acid containing 1-12 carbon atoms, inclusive, Y is b -hydroxymethylene or carbonyl, X11 is hydrogen, fluorine or chlorine, Ac is the acyl radical of a hydrocarbon carboxylic acid containing 1-12 carbon atoms, the dotted line represents an optional 1,2-double bond, X111 represents bromine or iodine, and R11 is an alkyl or aryl radical and processes for the preparation thereof by oxidatively hydroxylating a 21-acylate of 6a , 16b -dimethyl-11b ,21-dihydroxy-4, 17(20)-pregnadien-3-one I, with osmium tetroxide and an oxidising agent to obtain the corresponding 17a -hydroxy-20-keto-21-acyloxy compound II, treating II with a base to obtain 6a ,16b -dimethyl-11b , 17a ,21 - trihydroxy - 4 - pregnene - 3,20 - dione III, which may be oxidised to the corresponding 11-keto compound; or alternatively treating II with a dehydrating agent to obtain the corresponding 9(11)-dehydro compound V, treating-V with hypohalous acid to obtain the corresponding 9a -halo-11b -hydroxy compound VI, treating VI with a base to produce a 9(11)-oxido compound VII, treating VII with HF to obtain a 9a -fluoro compound which is hydrolysed to obtain 9a -fluoro-11b ,17a ,21-trihydroxy-16b -methyl-4-pregnene-3, 20-dione. Starting with 6a , 16b - dimethyl - 11b , 17a , 21 - trihydroxy - 1, 4 - pregnadiene-3,20-dione and using a similar procedure gives 9a -fluoro-11b ,17a ,21-trihydroxy-16b -methyl - 1, 4 - pregnadiene - 3, 20 - dione. Oxidation gives the 11-keto compounds. Treatment of the 21-hydroxy compounds with a sulphonating agent gives the corresponding 21-sulphonate ester which is converted to the corresponding 21-iodo compound with alkali metal iodide. Treating the 21-iodo compound with silver fluoride gives the corresponding 21-fluoro compound. Specifications 771,344, 781,712 and 898,295 are referred to.ALSO:Pharmaceutical compositions comprise 6a , 16b - dimethyl - 11b ,17a ,21 - trihydroxy - 4-pregnene - 3,20 - dione, 6a ,16b - dimethyl-17a ,21 - dihydroxy - 4 - pregnene - 3,11,20-trione, 6a ,16b - dimethyl - 9a - fluoro - 11b , 17a ,21 - trihydroxy - 4 - pregnene - 3,20-dione, 6a ,16b - dimethyl - 9a - fluoro - 17a ,211-dihydroxy - 4 - pregnene - 3,11,20 - trione or the corresponding D 1,4 compounds, and a pharmaceutical diluent. They are employed orally, as tablets, for injection in suspensions, or topically as ointments, with or without coacting antibiotics, e.g. neomycin, tetracycline, chloramphenicol and novobiocin. Specifications 771,344, 781,712 and 898,295 are referred to.
GB892260A 1959-03-18 1960-03-14 Improvements in or relating to steroids and the manufacture thereof Expired GB898291A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US80009159A 1959-03-18 1959-03-18

Publications (1)

Publication Number Publication Date
GB898291A true GB898291A (en) 1962-06-06

Family

ID=25177459

Family Applications (2)

Application Number Title Priority Date Filing Date
GB892260A Expired GB898291A (en) 1959-03-18 1960-03-14 Improvements in or relating to steroids and the manufacture thereof
GB2909561A Expired GB898295A (en) 1959-03-18 1960-03-14 Improvements in or relating to steroids and the manufacture thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2909561A Expired GB898295A (en) 1959-03-18 1960-03-14 Improvements in or relating to steroids and the manufacture thereof

Country Status (2)

Country Link
CH (3) CH396896A (en)
GB (2) GB898291A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3227312A1 (en) * 1982-07-19 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018089373A2 (en) 2016-11-08 2018-05-17 Regeneron Pharmaceuticals, Inc. Steroids and protein-conjugates thereof
MX2019013690A (en) 2017-05-18 2020-01-27 Regeneron Pharma Cyclodextrin protein drug conjugates.
CA3098453A1 (en) 2018-05-09 2019-11-14 Regeneron Pharmaceuticals, Inc. Anti-msr1 antibodies and methods of use thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3227312A1 (en) * 1982-07-19 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE
EP0100874A2 (en) * 1982-07-19 1984-02-22 Schering Aktiengesellschaft 6,16-Dimethyl corticoids, their preparation and their use
EP0100874A3 (en) * 1982-07-19 1985-04-17 Schering Aktiengesellschaft Berlin Und Bergkamen 6,16-dimethyl corticoids, their preparation and their use
US4555507A (en) * 1982-07-19 1985-11-26 Schering Aktiengesellschaft Novel 6, 16-dimethylcorticoids, their preparation and use

Also Published As

Publication number Publication date
CH397665A (en) 1965-08-31
CH396895A (en) 1965-08-15
CH396896A (en) 1965-08-15
GB898295A (en) 1962-06-06

Similar Documents

Publication Publication Date Title
GB902294A (en) Improvements in or relating to steroids and the manufacture thereof
US2865935A (en) 2-methyl steroids and process
GB898291A (en) Improvements in or relating to steroids and the manufacture thereof
GB869511A (en) Improvements in or relating to steroids and the manufacture thereof
GB1060793A (en) Improvements in or relating to steroids and the manufacture thereof
GB907812A (en) Improvements in or relating to steroids and the manufacture thereof
US3177230A (en) 2alpha-fluoro-11-oxygenated-17alpha-hydroxy-4, 6-pregnadiene-3, 20-diones
US2953581A (en) 3-oxygenated-20-keto-21-fluoro-pregnanes
DE1668658A1 (en) Manufacture of new halogen steroids
GB898293A (en) Improvements in or relating to steroids and the manufacture thereof
GB894604A (en) Improvements in or relating to steroids and the manufacture thereof
US3819604A (en) 6,9,21-trihalogenosteroids
GB923944A (en) Improvements in or relating to steroids and the manufacture thereof
GB885092A (en) Improvements in or relating to steroids and the manufacture thereof
GB903049A (en) Steroid compounds, preparation thereof and compositions thereof
GB894642A (en) Improvements in or relating to steroids and the manufacture thereof
GB946577A (en) Improvements in or relating to steroids and the manufacture thereof
GB959794A (en) Improvements in or relating to steroids
US3165543A (en) 2alpha-halo-and 2alpha-halo-6alpha-methyl-17alpha, 21-dihydroxy-4-pregnene-3, 20-diones
GB944716A (en) 10ª -fluoro steroids and their preparation
GB1037772A (en) Improvements in or relating to í¸-steroid compounds
GB923943A (en) Improvements in or relating to steroids and the manufacture thereof
NO132189B (en)
GB946578A (en) Improvements in or relating to steroids and the manufacture thereof
GB872201A (en) Improvements in or relating to steroids and the manufacture thereof