GB970482A - New 17-desoxy corticosteroids and processes for their preparation - Google Patents

New 17-desoxy corticosteroids and processes for their preparation

Info

Publication number
GB970482A
GB970482A GB1731261A GB1731261A GB970482A GB 970482 A GB970482 A GB 970482A GB 1731261 A GB1731261 A GB 1731261A GB 1731261 A GB1731261 A GB 1731261A GB 970482 A GB970482 A GB 970482A
Authority
GB
United Kingdom
Prior art keywords
methyl
pregnane
acyloxy
dione
effected
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
GB1731261A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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
Priority claimed from FR827205A external-priority patent/FR1363860A/en
Priority claimed from FR827304A external-priority patent/FR83203E/en
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB970482A publication Critical patent/GB970482A/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)

Abstract

The invention comprises compounds having the general formula: <FORM:0970482/C1/1> in which R1 is the oxygen atom of a ketone group or an 11b -hydroxyl group and R2 is hydrogen or an acyl radical derived from an organic acid and which may also contain substituents in the A and B rings, and processes for the preparation thereof by subjecting 3a -hydroxy-16a -methyl-5b -pregnane-11, 20-dione to selective halogenation to yield the corresponding 21-halogeno derivative having the general formula: <FORM:0970482/C1/2> wherein X and Y are both iodine atoms or wherein X is a halogen atom and Y is a hydrogen atom, reacting this compound with an acylating agent to yield a 3a -hydroxy-16a -methyl-21-acyloxy-5b -pregnane-11, 20-dione, oxidizing the 3a -hydroxy-16a -methyl-21-acyloxy-5b -pregnane-11, 20-dione to the corresponding 16a -methyl-21-acyloxy-5b -pregnane-3, 11, 20-trione, which is dibrominated to produce the corresponding 2a , 4b -dibromo-16a -methyl-21-acyloxy-5b -pregnane 3, 11, 20-trione and dehydrobrominated so as to introduce thereinto 1- and 4-double bonds yielding the corresponding 16a -methyl-21-acyl-17-desoxyprednisone. Selective halogenation may be effected with bromine in the presence of acetyl chloride or with iodine in the presence of calcium oxide and calcium chloride. Dibromination may be effected with bromine in ethyl acetate and dehydrobromination by a lithium bromide-lithium carbonate couple. Esterification may be effected at 21-position, 16a -methyl-17-desoxyprednisone or a 21-ester thereof may be reduced e.g. with potassium borohydride to the corresponding prednisolones after protecting the ketone groups at 3 and 20-positions with semi-carbazone. Specifications 970,481 and 970,487 are referred to.
GB1731261A 1960-05-14 1961-05-11 New 17-desoxy corticosteroids and processes for their preparation Expired GB970482A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR827205A FR1363860A (en) 1960-05-14 1960-05-14 New corticosteroids and their preparation process
FR827304A FR83203E (en) 1960-05-16 1960-05-16 New corticosteroids and their preparation process

Publications (1)

Publication Number Publication Date
GB970482A true GB970482A (en) 1964-09-23

Family

ID=26186033

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1731261A Expired GB970482A (en) 1960-05-14 1961-05-11 New 17-desoxy corticosteroids and processes for their preparation
GB109863A Expired GB970487A (en) 1960-05-14 1961-05-11 Novel steroids compounds and processes for the preparation thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB109863A Expired GB970487A (en) 1960-05-14 1961-05-11 Novel steroids compounds and processes for the preparation thereof

Country Status (3)

Country Link
BE (1) BE603711A (en)
CH (1) CH404661A (en)
GB (2) GB970482A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101397322B (en) * 2007-09-29 2011-05-04 天津药业研究院有限公司 Preparation of desoximetasone

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101397322B (en) * 2007-09-29 2011-05-04 天津药业研究院有限公司 Preparation of desoximetasone

Also Published As

Publication number Publication date
CH404661A (en) 1965-12-31
BE603711A (en) 1961-11-13
GB970487A (en) 1964-09-23

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