GB959378A - 21-substituted 17ª‡, 21-dioxy steroids and processes for their preparation - Google Patents

21-substituted 17ª‡, 21-dioxy steroids and processes for their preparation

Info

Publication number
GB959378A
GB959378A GB15754/63A GB1575463A GB959378A GB 959378 A GB959378 A GB 959378A GB 15754/63 A GB15754/63 A GB 15754/63A GB 1575463 A GB1575463 A GB 1575463A GB 959378 A GB959378 A GB 959378A
Authority
GB
United Kingdom
Prior art keywords
group
positions
halogen
dione
acetate
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
GB15754/63A
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.)
Scherico Ltd
Original Assignee
Scherico 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
Application filed by Scherico Ltd filed Critical Scherico Ltd
Publication of GB959378A publication Critical patent/GB959378A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Abstract

The invention comprises 17a , 21-dihydroxysteroids having at the 17-position the general formula: <FORM:0959378/C2/1> wherein R1 represents hydrogen or an acyl group, and either B represents an alkyl or alkanoyl group containing up to 8 carbon atoms or an aralkyl group, or the hydrogen at the 21-position is absent and B then represents an alkylidene group containing up to 8 carbon atoms or an aralkylidene group, and the preparation thereof by acid hydrolysing the corresponding steroids having at the 17-position the general formula: <FORM:0959378/C2/2> wherein B has the above significance and R and R1 represent an aralkyl group or an alkyl group containing up to 8 carbon atoms or together represent a cycloaliphatic ring and when required, acylating the 21-hydroxy group. The steroids having at the 17-position the first formula above may contain oxo groups at the 3- and/or 11-positions, halogen at one or more of the 2-, 4-, 6-, 9-, 11- and 12-positions, alkyl groups at one or more of the 2-, 6- and 16-positions, hydroxy groups at one or more of the 1-, 2-, 3-, 11- and 12-positions, and unsaturation at one or more of the 1-, 4-, 5-, 6-, 7- and 9-positions. Typical compounds are of the general formula: <FORM:0959378/C2/3> and the corresponding 1, 2-dihydro compounds, wherein A represents hydrogen or a methyl group, Z represents halogen or hydrogen, or a methyl group, D represents an alkyl or alkylidene group containing up to 8 carbon atoms, Y represents O, (H,OH), (H,O-Acy) or (H, Halogen) except that when Y represents halogen X also represents halogen, R1 represents hydrogen or an acyl group, and B has the above significance. In the examples 21-methyl-prednisolone and 9a -fluoro-16a , 21-dimethyl-prednisolone and the corresponding 21-acetates are prepared by acid hydrolysing the corresponding 17a , 21-isopropylidenedioxy compounds and acetylating the products to form the 21-acetates; and 9a -chloro -21- methylene-1, 4-pregnadiene-11b , 17a , 21-triol-3, 20-dione 11b -formate and the corresponding 21-acetate are prepared by treating 17a , 21-isopropylidene-dioxy-1, 4, 9 (11)- pregnatriene-3, 20-dione with formaldehyde to form the corresponding 21-methylene compound, acid hydrolysing this compound to form 21-methylene -1, 4, 9 (11)-pregnatriene-17a , 21-diol-3, 20-dione, acetylating this compound to form the corresponding 21-acetate, treating the 21-acetate with N-chlorosuccinimide to form 9a -chloro-21-methylene-1, 4-pregnadiene-11b , 17a , 21-triol-3, 20-dione 11b -formate 21-acetate, and hydrolysing this compound with methanolic perchloric acid to form the corresponding 11b -formate-21-ol. Therapeutic compositions, which may be administered in forms such as creams, unguents, tablets and elixirs for the treatment of inflammatory diseases, contain steroid compounds having at the 17-position the first general formula above.
GB15754/63A 1959-10-12 1960-09-13 21-substituted 17ª‡, 21-dioxy steroids and processes for their preparation Expired GB959378A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US84566159A 1959-10-12 1959-10-12
US84559559A 1959-10-12 1959-10-12
US84559459A 1959-10-12 1959-10-12

Publications (1)

Publication Number Publication Date
GB959378A true GB959378A (en) 1964-06-03

Family

ID=27420319

Family Applications (2)

Application Number Title Priority Date Filing Date
GB15754/63A Expired GB959378A (en) 1959-10-12 1960-09-13 21-substituted 17ª‡, 21-dioxy steroids and processes for their preparation
GB31484/60A Expired GB959377A (en) 1959-10-12 1960-09-13 Dioxy steroids and processes for their preparation

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB31484/60A Expired GB959377A (en) 1959-10-12 1960-09-13 Dioxy steroids and processes for their preparation

Country Status (7)

Country Link
BE (1) BE595971A (en)
CH (1) CH392500A (en)
DE (1) DE1188079B (en)
DK (1) DK108281C (en)
FR (2) FR1428454A (en)
GB (2) GB959378A (en)
NL (1) NL6810178A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8207151B2 (en) 2008-05-28 2012-06-26 Validus Biopharma Inc. Non-hormonal steroid modulators of NF-κB for treatment of disease
US9198921B2 (en) 2010-04-05 2015-12-01 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-κB for treatment of disease
US10799514B2 (en) 2015-06-29 2020-10-13 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-kappa beta for treatment of disease
US11382922B2 (en) 2019-03-07 2022-07-12 Reveragen Biopharma, Inc. Aqueous oral pharmaceutical suspension compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4069322A (en) * 1976-10-12 1978-01-17 Interx Research Corporation Pro-drugs for the improved delivery of certain selected anti-inflammatory steroids

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2866799A (en) * 1957-01-02 1958-12-30 Merck & Co Inc Method for converting a 17-20, 20-21 bismethylenedioxy or a 17-20, 20-21 bis-substituted methylenedioxy steroid of the pregnane series to a 17alpha, 21-dihydroxy-20-ketosteroid of the pregnane series

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10857161B2 (en) 2008-05-28 2020-12-08 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-kB for treatment of disease
US8334279B2 (en) 2008-05-28 2012-12-18 Validus Genetics Non-hormonal steroid modulators of NF-κB for treatment of disease
US8673887B2 (en) 2008-05-28 2014-03-18 Reveragen Biopharma, Inc Non-hormonal steroid modulators of NF-kB for treatment of disease
US8207151B2 (en) 2008-05-28 2012-06-26 Validus Biopharma Inc. Non-hormonal steroid modulators of NF-κB for treatment of disease
US9434758B2 (en) 2008-05-28 2016-09-06 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-κB for treatment of disease
US9649320B2 (en) 2008-05-28 2017-05-16 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-κB for treatment of disease
US11833159B2 (en) 2008-05-28 2023-12-05 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-kB for treatment of disease
US10206933B2 (en) 2008-05-28 2019-02-19 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-kB for treatment of disease
US9198921B2 (en) 2010-04-05 2015-12-01 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-κB for treatment of disease
US10000525B2 (en) 2010-04-05 2018-06-19 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-κB for treatment of disease
US10799514B2 (en) 2015-06-29 2020-10-13 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-kappa beta for treatment of disease
US11690853B2 (en) 2015-06-29 2023-07-04 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-κβ for treatment of disease
US11382922B2 (en) 2019-03-07 2022-07-12 Reveragen Biopharma, Inc. Aqueous oral pharmaceutical suspension compositions
US11471471B2 (en) 2019-03-07 2022-10-18 Reveragen Biopharma, Inc. Aqueous oral pharmaceutical suspension compositions

Also Published As

Publication number Publication date
FR1428454A (en) 1966-02-18
GB959377A (en) 1964-06-03
BE595971A (en) 1961-02-01
CH392500A (en) 1965-05-31
DK108281C (en) 1967-11-06
DE1188079B (en) 1965-03-04
NL6810178A (en) 1968-10-25
FR957M (en) 1961-11-27

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