GB984839A - Steroid compounds - Google Patents

Steroid compounds

Info

Publication number
GB984839A
GB984839A GB4296162A GB4296162A GB984839A GB 984839 A GB984839 A GB 984839A GB 4296162 A GB4296162 A GB 4296162A GB 4296162 A GB4296162 A GB 4296162A GB 984839 A GB984839 A GB 984839A
Authority
GB
United Kingdom
Prior art keywords
methyl
halo
progesterone
group
compound
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
GB4296162A
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.)
Wyeth Canada Inc
Original Assignee
Ayerst Mckenna and Harrison Inc
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 Ayerst Mckenna and Harrison Inc filed Critical Ayerst Mckenna and Harrison Inc
Publication of GB984839A publication Critical patent/GB984839A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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 6a -halo-17a -methyl-progesterone and the corresponding D 1,4-pregnadiene and steroids of the general formula <FORM:0984839/C2/1> wherein R1 represents an acyloxy, hydroxy or ketonic group, R2 represents an a -hydroxy group, and R3 represents a b -halogen atom or R2 and R3 together represent an a -oxido group when R1 represents an acyloxy group, and a process for the preparation of 6a -halo-17a -methyl-progesterone and the corresponding D 1,4-pregnadiene by epoxidizing a steroid of the formula <FORM:0984839/C2/2> wherein Ac represents an acyl group, treating the resulting 3b -acyloxy-5a ,6a -oxido-17a -methyl - pregnan - 20 - one with anhydrous hydrogen halide to form 6b -halo-3b ,5a -dihydroxy-17a - methyl - pregnan - 20 - one 3 - acylate, hydrolysing this compound to the corresponding free 3b ,5a -dihydroxy compound, oxidizing this compound to form 5a -hydroxy-6b -halo-17a - methyl - pregnane - 3,20 - dione, treating this compound with a dehydrating agent i.e. an alkali metal hydroxide or a strong acid, to remove the elements of water from positions 4 and 5 with concomitant inversion a carbon atom 6 to form the desired progesterone and, when required, dehydrogenating with 2,3-dichloro-5,6 - dicyano - quinone to form the corresponding D 1,4-pregnadiene. Therapeutic compositions having progestational activity comprise 6a -halo-17a -methyl-progesterone or 1-dehydro-6a -halo-17a -methyl-progesterone and a pharmaceutical acceptable carrier such as an orally ingestible pharmaceutically acceptable carrier, an injectable liquid or a percutaneous pharmaceutical carrier.
GB4296162A 1961-11-17 1962-11-13 Steroid compounds Expired GB984839A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US15320361A 1961-11-17 1961-11-17

Publications (1)

Publication Number Publication Date
GB984839A true GB984839A (en) 1965-03-03

Family

ID=22546202

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4296162A Expired GB984839A (en) 1961-11-17 1962-11-13 Steroid compounds

Country Status (2)

Country Link
CH (1) CH414617A (en)
GB (1) GB984839A (en)

Also Published As

Publication number Publication date
CH414617A (en) 1966-06-15

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