GB945158A - New steroid compounds and processes for their formation - Google Patents

New steroid compounds and processes for their formation

Info

Publication number
GB945158A
GB945158A GB4595962A GB4595962A GB945158A GB 945158 A GB945158 A GB 945158A GB 4595962 A GB4595962 A GB 4595962A GB 4595962 A GB4595962 A GB 4595962A GB 945158 A GB945158 A GB 945158A
Authority
GB
United Kingdom
Prior art keywords
group
ketal
oxygen atom
positions
methyl
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
GB4595962A
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
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB945158A publication Critical patent/GB945158A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises pregna-3,20-dione compounds having the formula: <FORM:0945158/C2/1> wherein R and R1 both represent cyclic ketal groupings, R2 represents a hydroxyl group in the a -orientation and a hydrogen atom, the oxygen atom =O of a keto group or a hydroxy group and a methyl group, or alternatively R1 is the oxygen atom =O of a keto group and R and R2 remain as before or alternatively both R and R1 represent the oxygen atom =O of a keto group and R2 is as before; when R represents the cyclic ketal group then a double bond exists between the 5- and 6-positions but when R represents the oxygen atom =O then the double bond lies between the 4- and 5-positions; and processes for the preparation thereof by ketalising 12a -hydroxy-progesterone at the 3- and 20-positions, oxidising the ketal thus obtained to produce the corresponding 3,20-dicyclic ketal of pregn-5-en-12-one, reacting this compound with a Grignard reagent to form the corresponding 3,20-dicyclic ketal of 12 #x-hydroxy12 #x-methyl-pregn-5-ene, which compound may be hydrolysed to liberate one or both of the protected ketone groups by acid hydrolysis. Ketalisation may be effected with ethylene glycol in the presence of p-toluene-sulphonic acid, oxidation with chromic acid and the Grignard reaction with methyl magnesium bromide.
GB4595962A 1959-06-18 1960-06-16 New steroid compounds and processes for their formation Expired GB945158A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR797893A FR1357602A (en) 1959-06-18 1959-06-18 Process for the preparation of steroids substituted in position 12 and products thereof

Publications (1)

Publication Number Publication Date
GB945158A true GB945158A (en) 1963-12-23

Family

ID=8716205

Family Applications (2)

Application Number Title Priority Date Filing Date
GB4595962A Expired GB945158A (en) 1959-06-18 1960-06-16 New steroid compounds and processes for their formation
GB2121460A Expired GB945157A (en) 1959-06-18 1960-06-16 Improvements in or relating to processes for the production of steroid compounds and the compounds thus produced

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2121460A Expired GB945157A (en) 1959-06-18 1960-06-16 Improvements in or relating to processes for the production of steroid compounds and the compounds thus produced

Country Status (5)

Country Link
BE (1) BE592005A (en)
CH (1) CH395074A (en)
ES (1) ES259017A1 (en)
FR (1) FR1357602A (en)
GB (2) GB945158A (en)

Also Published As

Publication number Publication date
BE592005A (en) 1960-12-19
GB945157A (en) 1963-12-23
CH395074A (en) 1965-07-15
ES259017A1 (en) 1960-09-16
FR1357602A (en) 1964-04-10

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