GB737957A - Steroid ketals - Google Patents

Steroid ketals

Info

Publication number
GB737957A
GB737957A GB21285/53A GB2128553A GB737957A GB 737957 A GB737957 A GB 737957A GB 21285/53 A GB21285/53 A GB 21285/53A GB 2128553 A GB2128553 A GB 2128553A GB 737957 A GB737957 A GB 737957A
Authority
GB
United Kingdom
Prior art keywords
diketal
dione
diol
chloro
acid
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
GB21285/53A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB737957A publication Critical patent/GB737957A/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
    • 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 a 3,20-cyclic diketal of a 4-chloro- or 4-bromo-pregnane-3,20-dione and the preparation thereof by mixing together an alkane-1,2-diol or an alkane-1,3-diol and a steroid 4-halo-3,20-dione having a pregnane carbon skeleton in the presence of an acid catalyst, e.g. m- and p-toluene sulphonic acids, naphthalene sulphonic acid, benzenesulphonic acid, ortho-chlorobenzenesulphonic acid, hydrochloric acid and sulphuric acid, at a temperature between about 20 DEG and 200 DEG C., to cause conversion of the 3- and 20-ketone groups to ketal groups. Examples disclose the production of 4 - chloro - 17a - hydroxypregnane - 3,11,20-trione 3,20-ethylene glycol diketal, 4-chloro-11b , 17a - dihydroxypregnane - 3,20 - dione 3,20-ethylene glycol diketal, 4-chloropregnane-3,20-dione 3,20-ethylene glycol diketal, 4-chloro-17a -hydroxypregnane-3,11,20-trione 3,20-propane-1,2 and 1,3-diol diketal, 4-bromo-17a -hydroxypregnane-3,11,20-trione 3,20-propane-1,2-diol diketal, 4 - bromo - 11b ,17a - dihydroxypregnane - 3,20 - dione - 3,20 - propane - 1,2 - diol diketal, 4 - bromopregnane - 3,11,20 - trione 3,20 - (3 - methyl - pentane - 1,2 - diol) - diketal, 4 - bromo - 12 - hydroxypregnane - 3,20 - dione 3,20 - propane - 1,3 - diol diketal and 4-chloro-11a ,17a - dihydroxypregnane - 3,20 - dione 3,20-ethylene glycol diketal.
GB21285/53A 1952-08-16 1953-07-31 Steroid ketals Expired GB737957A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US737957XA 1952-08-16 1952-08-16

Publications (1)

Publication Number Publication Date
GB737957A true GB737957A (en) 1955-10-05

Family

ID=22115847

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21285/53A Expired GB737957A (en) 1952-08-16 1953-07-31 Steroid ketals

Country Status (1)

Country Link
GB (1) GB737957A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3052696A (en) * 1960-03-16 1962-09-04 Roussel Uclaf Novel 16alpha-methyl-delta4, 9(11)-pregnadienes and preparation thereof
US3079382A (en) * 1958-04-16 1963-02-26 Farmaceutici Italia Process for the synthesis of 4-methyl-17-alpha-hydroxyprogesterone and its esters
US3088945A (en) * 1958-08-07 1963-05-07 Merck & Co Inc Process for the preparation of 12alpha-alkyl steroids

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3079382A (en) * 1958-04-16 1963-02-26 Farmaceutici Italia Process for the synthesis of 4-methyl-17-alpha-hydroxyprogesterone and its esters
US3088945A (en) * 1958-08-07 1963-05-07 Merck & Co Inc Process for the preparation of 12alpha-alkyl steroids
US3052696A (en) * 1960-03-16 1962-09-04 Roussel Uclaf Novel 16alpha-methyl-delta4, 9(11)-pregnadienes and preparation thereof

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