GB1082573A - Improvements in the preparation of steroid esters - Google Patents

Improvements in the preparation of steroid esters

Info

Publication number
GB1082573A
GB1082573A GB621565A GB621565A GB1082573A GB 1082573 A GB1082573 A GB 1082573A GB 621565 A GB621565 A GB 621565A GB 621565 A GB621565 A GB 621565A GB 1082573 A GB1082573 A GB 1082573A
Authority
GB
United Kingdom
Prior art keywords
methyl
prednisolone
group
chlorine
fluorine
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
GB621565A
Inventor
Peter Oxley
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.)
Boots Pure Drug Co Ltd
Original Assignee
Boots Pure Drug Co 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 Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Priority to GB621565A priority Critical patent/GB1082573A/en
Priority to GB1121067A priority patent/GB1082574A/en
Priority to NO16154566A priority patent/NO127190B/no
Priority to DK69066A priority patent/DK118557B/en
Priority to DE19661568077 priority patent/DE1568077A1/en
Priority to FR49246A priority patent/FR1469675A/en
Priority to CH195666A priority patent/CH452518A/en
Priority to SE01806/66A priority patent/SE326955B/xx
Priority to FR60887A priority patent/FR5457M/fr
Publication of GB1082573A publication Critical patent/GB1082573A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises (a) a process for preparing 17a - acyloxy - 11b - hydroxy steroids by conversion of a 17a ,11b -dihydroxy steroid to its 11-nitrate, converting this to its 17-acylate, and removing the nitrate group by a non-hydrolytic method, followed if desired by 1-dehydrogenation; and (b) compounds of formula <FORM:1082573/C2/1> wherein R8 is a hydrogen atom or a group -COR1, R1 is a C1- 6 alkyl group, R2\h is hydrogen, methyl, fluorine or chlorine, R3 is fluorine, chlorine or an alkanoyloxy, alkanesulphonyloxy or arenesulphonyloxy group, R4 is hydrogen or methyl and A is a vinylidene group or a methylene or a - or b -R5-substituted methylene group wherein R5 is fluorine, chlorine, methyl or acyloxy. 21 - Fluoro - 16a - methyl - hydrocortisone is prepared by converting 16a -methyl-hydrocortisone to its 21-methanesulphonate and treating this with potassium fluoride. 21 - Methyl - 21 - fluoro - prednisolone is prepared by treatment of 21-methyl-prednisolone 17a ,21-acetonide with oxalic acid to form 21-methyl-prednisolone (which may be converted to its 21-acetate), converting this to its 21-methanesulphonate, and treating this with potassium fluoride, there being obtained as a by - product 21 - methyl - prednisolone - 17a ,21-oxide. 1,9(11) - Bis - dehydro - cortexolone - 17a ,21-diacetate is obtained as a by-product from the acetylation of prednisolone - 21 acetate - 11 - nitrate.
GB621565A 1965-02-12 1965-02-12 Improvements in the preparation of steroid esters Expired GB1082573A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB621565A GB1082573A (en) 1965-02-12 1965-02-12 Improvements in the preparation of steroid esters
GB1121067A GB1082574A (en) 1965-02-12 1965-02-12 Steroid esters
NO16154566A NO127190B (en) 1965-02-12 1966-02-02
DK69066A DK118557B (en) 1965-02-12 1966-02-10 Process for the preparation of 17α-acyloxy-11β-hydroxy-Δ <4> -pregnant-3,20-diones.
DE19661568077 DE1568077A1 (en) 1965-02-12 1966-02-11 Process for the production of steroid esters, new steroid esters and their use
FR49246A FR1469675A (en) 1965-02-12 1966-02-11 Process for the preparation of steroid esters and products obtained
CH195666A CH452518A (en) 1965-02-12 1966-02-11 Process for the preparation of 17a-acyloxy-11B-hydroxysteroids
SE01806/66A SE326955B (en) 1965-02-12 1966-02-11
FR60887A FR5457M (en) 1965-02-12 1966-05-10

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB621565A GB1082573A (en) 1965-02-12 1965-02-12 Improvements in the preparation of steroid esters

Publications (1)

Publication Number Publication Date
GB1082573A true GB1082573A (en) 1967-09-06

Family

ID=9810513

Family Applications (2)

Application Number Title Priority Date Filing Date
GB621565A Expired GB1082573A (en) 1965-02-12 1965-02-12 Improvements in the preparation of steroid esters
GB1121067A Expired GB1082574A (en) 1965-02-12 1965-02-12 Steroid esters

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1121067A Expired GB1082574A (en) 1965-02-12 1965-02-12 Steroid esters

Country Status (7)

Country Link
CH (1) CH452518A (en)
DE (1) DE1568077A1 (en)
DK (1) DK118557B (en)
FR (1) FR5457M (en)
GB (2) GB1082573A (en)
NO (1) NO127190B (en)
SE (1) SE326955B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997040836A1 (en) * 1996-05-02 1997-11-06 G.D. Searle & Co. Novel pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs
US5707984A (en) * 1995-12-08 1998-01-13 G. D. Searle & Co. Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs
US5792758A (en) * 1995-12-08 1998-08-11 G. D. Searle & Co. Steroid nitrite ester derivatives useful as anti-inflammatory drugs
US5824669A (en) * 1996-03-22 1998-10-20 Nitromed, Inc. Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders
US5837698A (en) * 1996-05-02 1998-11-17 G. D. Searle & Co. Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5707984A (en) * 1995-12-08 1998-01-13 G. D. Searle & Co. Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs
US5792758A (en) * 1995-12-08 1998-08-11 G. D. Searle & Co. Steroid nitrite ester derivatives useful as anti-inflammatory drugs
US5824669A (en) * 1996-03-22 1998-10-20 Nitromed, Inc. Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders
US6197762B1 (en) 1996-03-22 2001-03-06 Nitromed, Inc. Nitrosated and nitrosylated steroids compositions, and methods for treating respiratory disorders
USRE37116E1 (en) * 1996-03-22 2001-03-27 Nitromed, Inc. Nitrosated and nitrosylated compounds, and compositions and their use for treating respiratory disorders
US6579863B1 (en) 1996-03-22 2003-06-17 Nitromed, Inc. Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders
US7160920B2 (en) 1996-03-22 2007-01-09 Nitromed, Inc. Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders
US7345037B2 (en) 1996-03-22 2008-03-18 Nitromed, Inc. Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders
WO1997040836A1 (en) * 1996-05-02 1997-11-06 G.D. Searle & Co. Novel pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs
US5837698A (en) * 1996-05-02 1998-11-17 G. D. Searle & Co. Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs
US5985862A (en) * 1996-05-02 1999-11-16 G.D. Searle & Co. Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs

Also Published As

Publication number Publication date
GB1082574A (en) 1967-09-06
DE1568077A1 (en) 1970-03-12
SE326955B (en) 1970-08-10
CH452518A (en) 1968-03-15
FR5457M (en) 1967-10-16
DK118557B (en) 1970-09-07
NO127190B (en) 1973-05-21

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