GB939349A - Steroids - Google Patents

Steroids

Info

Publication number
GB939349A
GB939349A GB576161A GB576161A GB939349A GB 939349 A GB939349 A GB 939349A GB 576161 A GB576161 A GB 576161A GB 576161 A GB576161 A GB 576161A GB 939349 A GB939349 A GB 939349A
Authority
GB
United Kingdom
Prior art keywords
compound
methyl
pregnane
dione
diol
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
GB576161A
Inventor
Giangiacomo Nathansohn
Emilio Testa
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.)
Gruppo Lepetit SpA
Original Assignee
Lepetit 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 Lepetit SpA filed Critical Lepetit SpA
Priority to GB576161A priority Critical patent/GB939349A/en
Priority to DK31062A priority patent/DK128606B/en
Priority to DE19621468171 priority patent/DE1468171C3/en
Priority to CH143862A priority patent/CH420144A/en
Publication of GB939349A publication Critical patent/GB939349A/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 16b -methyl-5a -pregnane-3b ,17a -diol-11,20-dione and 16b -methyl-5a -pregnane- 17a ,21-diol-3,11,20-trione 12-acetate, and the preparation thereof by epoxidising 16-methyl-5a -preg-16-ene-3b -ol-11,20-dione 3b -acetate, for example, with hydrogen peroxide, heating the resulting 16b -methyl-16a ,17a - epoxy-5a -pregnane- 3b -ol-11, 20-dione, for example, with p-toluenesulphonic acid in an anhydrous inert solvent, to form 16-methylene-5a -pregnane-3b ,17a -diol-11,20-dione, and subjecting this compound to hydrogenation, to form the first compound above, and by acetyloxylating 16b -methyl-5a -pregnane- 3b ,17a -diol- 11,20-dione (which may be prepared by the previous process) to form 16b -methyl-5a -pregnane-3b , 17a ,21-triol-11,20-dione 21-acetate and oxidising this compound to form the second compound above. The latter process may be extended by brominating the 16b -methyl-17a , 21-diol-3,11,20-trione 21 acetate product to form the corresponding 2,4-dibromo compound and dehydrobrominating the dibromo compound to form 16b -methyl-prednisone 21-acetate and, if required, hydrolysing this compound to the corresponding 21-hydroxy compound. The acetyloxylating process referred to above may be carried out by adding bromine to a solution of the 16b -methyl-5a -pregnane-3b ,17a -diol-11,20-dione in an inert solvent to form the corresponding 21-bromo compound, and refluxing this compound with potassium acetate in aqueous actone.
GB576161A 1961-02-16 1961-02-16 Steroids Expired GB939349A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB576161A GB939349A (en) 1961-02-16 1961-02-16 Steroids
DK31062A DK128606B (en) 1961-02-16 1962-01-23 Process for the preparation of 16β-methylprednisone or its 21-acetate.
DE19621468171 DE1468171C3 (en) 1961-02-16 1962-01-31 Process for the production of 16 beta -methylprednisone and its 21-acetate
CH143862A CH420144A (en) 1961-02-16 1962-02-06 Process for the preparation of the therapeutically active 16B-methyl-prednisone-21-acetate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB576161A GB939349A (en) 1961-02-16 1961-02-16 Steroids

Publications (1)

Publication Number Publication Date
GB939349A true GB939349A (en) 1963-10-16

Family

ID=9802158

Family Applications (1)

Application Number Title Priority Date Filing Date
GB576161A Expired GB939349A (en) 1961-02-16 1961-02-16 Steroids

Country Status (4)

Country Link
CH (1) CH420144A (en)
DE (1) DE1468171C3 (en)
DK (1) DK128606B (en)
GB (1) GB939349A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4361558A (en) * 1980-04-29 1982-11-30 Ciba-Geigy Corporation Halogenated steroids

Also Published As

Publication number Publication date
DK128606B (en) 1974-06-04
DE1468171B2 (en) 1975-01-23
DE1468171A1 (en) 1974-08-01
CH420144A (en) 1966-09-15
DE1468171C3 (en) 1975-09-11

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