GB2001990A - Preparation of 16 alpha -methyl- prednisolone and derivatives thereof via 17 alpha -hydroperoxy analogues - Google Patents

Preparation of 16 alpha -methyl- prednisolone and derivatives thereof via 17 alpha -hydroperoxy analogues

Info

Publication number
GB2001990A
GB2001990A GB7830072A GB7830072A GB2001990A GB 2001990 A GB2001990 A GB 2001990A GB 7830072 A GB7830072 A GB 7830072A GB 7830072 A GB7830072 A GB 7830072A GB 2001990 A GB2001990 A GB 2001990A
Authority
GB
United Kingdom
Prior art keywords
compound
alpha
formula
image
hydroperoxy
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.)
Granted
Application number
GB7830072A
Other versions
GB2001990B (en
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.)
Lark SpA
Original Assignee
Lark SpA
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 Lark SpA filed Critical Lark SpA
Priority to GB7830072A priority Critical patent/GB2001990B/en
Publication of GB2001990A publication Critical patent/GB2001990A/en
Application granted granted Critical
Publication of GB2001990B publication Critical patent/GB2001990B/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
    • C07J5/0046—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 substituted in position 17 alfa
    • C07J5/0061—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 substituted in position 17 alfa substituted in position 16
    • C07J5/0069—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C07J5/0076—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

Compounds of formula (I): <IMAGE> wherein each X is hydrogen or fluorine and Ac is acetyl, are prepared by starting from a compound of formula (II): <IMAGE> which is subjected to a standard Grignard reagent under a nitrogen atmosphere to form a compound of formula (III): <IMAGE> which compound is treated with an aqueous solution of ammonium chloride in the presence of ethyl ether to form a compound of formula (IV): <IMAGE> which compound is reduced either with zinc dust in acetic acid or with an alkali metal iodide in an aliphatic ketone, to form the desired compound.
GB7830072A 1977-07-16 1978-07-17 Process for the preparation of prednisolone derivatives Expired GB2001990B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB7830072A GB2001990B (en) 1977-07-16 1978-07-17 Process for the preparation of prednisolone derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2998877 1977-07-16
GB7830072A GB2001990B (en) 1977-07-16 1978-07-17 Process for the preparation of prednisolone derivatives

Publications (2)

Publication Number Publication Date
GB2001990A true GB2001990A (en) 1979-02-14
GB2001990B GB2001990B (en) 1982-01-13

Family

ID=26260193

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7830072A Expired GB2001990B (en) 1977-07-16 1978-07-17 Process for the preparation of prednisolone derivatives

Country Status (1)

Country Link
GB (1) GB2001990B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0165037A2 (en) * 1984-06-11 1985-12-18 The Upjohn Company 16 alpha-methyl steroids and their preparation
WO1987007612A1 (en) * 1986-06-04 1987-12-17 The Upjohn Company 16alpha-METHYLATION PROCESS
US4891426A (en) * 1984-06-11 1990-01-02 The Upjohn Company 16α-methyl-17α 20-epoxysteroid and process
US4929395A (en) * 1984-06-11 1990-05-29 The Upjohn Company 16α-methylation process
EP0574318A1 (en) * 1992-06-11 1993-12-15 Roussel Uclaf New process for the preparation of 16-alpha-methyl-steroids
CN109096355A (en) * 2018-10-23 2018-12-28 山东泰华生物科技股份有限公司 A kind of preparation method of dexamethasone acetate

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0165037A2 (en) * 1984-06-11 1985-12-18 The Upjohn Company 16 alpha-methyl steroids and their preparation
EP0165037A3 (en) * 1984-06-11 1987-01-21 The Upjohn Company 16 alpha-methyl steroids and their preparation
US4704455A (en) * 1984-06-11 1987-11-03 The Upjohn Company 16α-methylatedΔ17(20)-corticoids
EP0278319A1 (en) * 1984-06-11 1988-08-17 The Upjohn Company 9,11-Epoxy-21-hydroxypregnane derivatives
US4891426A (en) * 1984-06-11 1990-01-02 The Upjohn Company 16α-methyl-17α 20-epoxysteroid and process
US4929395A (en) * 1984-06-11 1990-05-29 The Upjohn Company 16α-methylation process
US4990612A (en) * 1984-06-11 1991-02-05 The Upjohn Company 16α-methylation process
WO1987007612A1 (en) * 1986-06-04 1987-12-17 The Upjohn Company 16alpha-METHYLATION PROCESS
EP0574318A1 (en) * 1992-06-11 1993-12-15 Roussel Uclaf New process for the preparation of 16-alpha-methyl-steroids
FR2692266A1 (en) * 1992-06-11 1993-12-17 Roussel Uclaf New process for the preparation of alpha-methylated steroids
US6194565B1 (en) * 1992-06-11 2001-02-27 Hoechst Marion Roussel Process for preparing 16 α-methyl-steroids
CN109096355A (en) * 2018-10-23 2018-12-28 山东泰华生物科技股份有限公司 A kind of preparation method of dexamethasone acetate

Also Published As

Publication number Publication date
GB2001990B (en) 1982-01-13

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee