GB1202001A - 6alpha,9alpha-DIFLUOROPREDNISOLONE 17,21-DIESTERS - Google Patents

6alpha,9alpha-DIFLUOROPREDNISOLONE 17,21-DIESTERS

Info

Publication number
GB1202001A
GB1202001A GB2817668A GB2817668A GB1202001A GB 1202001 A GB1202001 A GB 1202001A GB 2817668 A GB2817668 A GB 2817668A GB 2817668 A GB2817668 A GB 2817668A GB 1202001 A GB1202001 A GB 1202001A
Authority
GB
United Kingdom
Prior art keywords
formula
compounds
difluoroprednisolone
dione
prepared
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
GB2817668A
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.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Pharmaceutical 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 Warner Lambert Pharmaceutical Co filed Critical Warner Lambert Pharmaceutical Co
Publication of GB1202001A publication Critical patent/GB1202001A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cleaning By Liquid Or Steam (AREA)

Abstract

1,202,001. 17,21-Diesters of 6α,9α-difluoroprednisolone. WARNER-LAMBERT PHARMACEUTICAL CO. 13 June, 1968 [16 June, 1967(5)], No. 28176/68. Heading C2U. [Also in Division A5] Novel compounds of formula (wherein R and R<SP>1</SP> are C 1-3 alkyl groups) are prepared (a) from the corresponding 17- monoesters by 21-esterification, and (b) from compounds of formula by treatment with HF (to give a 9α-fluoro-11#- hydroxy grouping) and 1,2-dehydrogenation (in either order). 6α,9α - Difluoroprednisolone 17 - (C 2-4 )- alkanoates are prepared by reacting 6α,9α- difluoroprednisolone with an orthoester of formula RC(OX) 3 (where X is a C 1-3 alkyl group), and hydrolysing the resulting 17α,21- alkyl orthoester. Compounds of Formula III are prepared from compounds of formula by fluorination and acidification to obtain a 6α fluoropregna - 4,9(11) - diene - 17α,21 -diol - 3,20-dione 17,21-diester which is treated with a source of HOBr to give a 6α-fluoro-9α- bromo-pregn - 4 - ene - 11#,17α,21 - triol - 3,20 - dione 17,21-diester, which is epoxidized (e.g. using potassium acetate) to give a compound of Formula III. Compounds of Formula VII are prepared from pregna-4,9(11)-diene-17α,21- diol-3,20-dione (a) by reaction with an orthoester of formula RC(OX) 3 , hydrolysis of the resulting 17α,21-alkyl orthoester and esterification of the thus-obtained pregna-4,9(11)-diene- 17α,21-diol-3,20-dione 17-monoester, or (b) by direct esterification (for a product wherein R = R<SP>1</SP>).
GB2817668A 1967-06-16 1968-06-13 6alpha,9alpha-DIFLUOROPREDNISOLONE 17,21-DIESTERS Expired GB1202001A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IT1727467 1967-06-16
IT1727367 1967-06-16
IT1727667 1967-06-16
IT1727767 1967-06-16
IT1727567 1967-06-16

Publications (1)

Publication Number Publication Date
GB1202001A true GB1202001A (en) 1970-08-12

Family

ID=27517779

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2817668A Expired GB1202001A (en) 1967-06-16 1968-06-13 6alpha,9alpha-DIFLUOROPREDNISOLONE 17,21-DIESTERS

Country Status (8)

Country Link
CH (2) CH551396A (en)
DE (1) DE1768673B1 (en)
DK (1) DK131994C (en)
FI (1) FI45657C (en)
FR (1) FR8195M (en)
GB (1) GB1202001A (en)
NO (1) NO129569B (en)
SE (1) SE339685B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2421914A1 (en) * 1978-04-05 1979-11-02 Prochem Ets 3-ACETOXY-9B-11B-EPOXY-PREGNA-TRIENES AND DIENES AND PROCESS FOR THE PREPARATION OF 6A-HALOGENO-PREGNA-1,4-DIENE-3 ONES AND OF 6A HALOGENO-PREGNA-4-ENE-3-ONES CORRESPONDENTS
EP0030615A1 (en) * 1979-11-16 1981-06-24 STEROSYNT Ltd. 6-Alpha-9-alpha-difluoro-16-beta-methyl-prednisolone-17,21 diesters and pharmaceutical compositions containing them

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2421914A1 (en) * 1978-04-05 1979-11-02 Prochem Ets 3-ACETOXY-9B-11B-EPOXY-PREGNA-TRIENES AND DIENES AND PROCESS FOR THE PREPARATION OF 6A-HALOGENO-PREGNA-1,4-DIENE-3 ONES AND OF 6A HALOGENO-PREGNA-4-ENE-3-ONES CORRESPONDENTS
EP0030615A1 (en) * 1979-11-16 1981-06-24 STEROSYNT Ltd. 6-Alpha-9-alpha-difluoro-16-beta-methyl-prednisolone-17,21 diesters and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
DK131994C (en) 1976-03-01
NO129569B (en) 1974-04-29
FR8195M (en) 1970-09-14
FI45657C (en) 1972-08-10
SE339685B (en) 1971-10-18
DE1768673B1 (en) 1971-10-14
DK131994B (en) 1975-10-06
FI45657B (en) 1972-05-02
CH553760A (en) 1974-09-13
CH551396A (en) 1974-07-15

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years