GB931221A - Steroid compounds - Google Patents

Steroid compounds

Info

Publication number
GB931221A
GB931221A GB3271259A GB3271259A GB931221A GB 931221 A GB931221 A GB 931221A GB 3271259 A GB3271259 A GB 3271259A GB 3271259 A GB3271259 A GB 3271259A GB 931221 A GB931221 A GB 931221A
Authority
GB
United Kingdom
Prior art keywords
ester
dimethyl
reacting
preparation
prednisolone
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
GB3271259A
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
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB931221A publication Critical patent/GB931221A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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 steroids of the general formulae <FORM:0931221/IV(a)/1> <FORM:0931221/IV(a)/2> <FORM:0931221/IV(a)/3> wherein X represents a hydrogen or halogen atom, R represents a keto or hydroxy group, R1 represents a hydrogen atom, an acyl group, or an ester group derived from an inorganic acid; a process for the preparation of 6a ,16b -dimethyl-cortisone or -hydrocortisone by reacting 3-ethylenedioxy-6,16b -dimethyl-11-keto (or b -hydroxy) 17(20),20(21)-bismethylenedioxy-5-pregnene, which may optionally be prepared by a process described in Specification 931,224 with p-toluene sulphonic acid followed by acetic acid and, when required, esterifying to produce a corresponding 21-ester; a process for the preparation of a 21-ester of 3,20-diketo-6a ,16b -dimethyl-17a ,21-dihydroxy- 4,9(11) -pregnadiene or -1,4,9(11)-pregnatriene by reacting a 21-ester of 6a ,16b -dimethylhydrocortisone or of 6a ,16b -dimethyl-prednisolone with an alkane sulphonyl halide; a process for the preparation of a 21-ester of 6a ,16b -dimethyl-9a -bromo-hydrocortisone or -prednisolone by reacting a 21-ester of 3,20-diketo-6a ,16b -dimethyl-17a ,21-dihydroxy- 4,9(11) -pregnadiene or -1,4,9(11)-pregnatriene with an N-bromoimide and optionally reacting this compound with sodium or potassium acetate to produce a 21-ester of 3,20-diketo-6a ,16b -dimethyl-9b , 11b -oxido- 17a ,21-dihydroxy- 4-pregnene or -1,4-pregnadiene; the preparation of a 21-ester of a 9a -halo-hydrocortisone or -prednisolone by reacting a 21-ester of 3,20-diketo-6a ,16b -dimethyl-9b ,11b -oxido- 17a , 21-dihydroxy-4-pregnene or -1,4-pregnadiene with a hydrohalic acid and optionally oxidising this compound to the corresponding 11-keto compound; a process for the preparation of a 6a ,16b -dimethyl-prednisolone or -prednisone or a 21-ester thereof by reacting the corresponding 4-pregnene with selenium dioxide; a process for the preparation of 6a ,16b -dimethyl-prednisolone by dehydrogenating a 21-ester of 6a ,16b -dimethyl-hydrocortisone or of 6a ,16b -dimethyl-cortisone with Schizomycetes microrganisms such as of the species Bacillus sphaericus; and a process for the preparation of 9a -halo-6a ,16b -dimethyl-prednisolone or -prednisone or a 21-ester thereof by reacting the corresponding 4-pregnene with selenium dioxide. In all the above processes a product containing a 21-ester group may be hydrolysed to a 21-hydroxy compound, or a product containing a 21-hydroxy group may be esterified to form a 21-ester compound. Specifications 867,786 and 867,787 also are referred to.
GB3271259A 1958-10-01 1959-09-25 Steroid compounds Expired GB931221A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US76452358A 1958-10-01 1958-10-01

Publications (1)

Publication Number Publication Date
GB931221A true GB931221A (en) 1963-07-17

Family

ID=25070956

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3271259A Expired GB931221A (en) 1958-10-01 1959-09-25 Steroid compounds
GB1344363A Expired GB931224A (en) 1958-10-01 1959-09-25 Steroid compounds and their production

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1344363A Expired GB931224A (en) 1958-10-01 1959-09-25 Steroid compounds and their production

Country Status (2)

Country Link
BE (1) BE583146A (en)
GB (2) GB931221A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2679015A (en) * 1951-01-31 1954-05-18 Gen Electric Eddy current brake, clutch, or the like
DE3227312A1 (en) * 1982-07-19 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2679015A (en) * 1951-01-31 1954-05-18 Gen Electric Eddy current brake, clutch, or the like
DE3227312A1 (en) * 1982-07-19 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE
GB2124230A (en) * 1982-07-19 1984-02-15 Schering Ag 616-dimethyl corticoids, their preparation 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
GB931224A (en) 1963-07-17
BE583146A (en) 1960-03-30

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