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ES251876A1 - New compounds useful in steroid synthesis and processes for the preparation thereof - Google Patents

New compounds useful in steroid synthesis and processes for the preparation thereof

Info

Publication number
ES251876A1
ES251876A1 ES0251876A ES251876A ES251876A1 ES 251876 A1 ES251876 A1 ES 251876A1 ES 0251876 A ES0251876 A ES 0251876A ES 251876 A ES251876 A ES 251876A ES 251876 A1 ES251876 A1 ES 251876A1
Authority
ES
Spain
Prior art keywords
formula
acid
diacyloxy
seco
hydroxy
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
ES0251876A
Other languages
Spanish (es)
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.)
Laboratoires Francais de Chimiotherapie SA
Laboratoires Francaise de Chimiotherapie
Original Assignee
Laboratoires Francais de Chimiotherapie SA
Laboratoires Francaise de Chimiotherapie
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 Laboratoires Francais de Chimiotherapie SA, Laboratoires Francaise de Chimiotherapie filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of ES251876A1 publication Critical patent/ES251876A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • 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 the 18,11-lactones of 11b -hydroxy-13,17-secoetiocholan-17,18-dioic acids of the general formula <FORM:0922315/IV(a)/1> wherein R represents =O, or b -OH, a -H, the methyl ester of 3a -hydroxy-11-keto-13,17-seco-etiochol-12-en-17-oic acid of the formula <FORM:0922315/IV(a)/2> the 17,18-lactone of 3a ,11b -diacyloxy-18-hydroxy-13,17-seco-13a -etiocholan-17-oic acid of the formula <FORM:0922315/IV(a)/3> and 3a ,11b - diacyloxy-13,17- seco-etiocholan-17,18-dioic acid of the formula <FORM:0922315/IV(a)/4> and the preparation of a compound of the first formula wherein R represents b -OH, a -H (1) by treating 3a , 11b -dihydroxy-17-keto-17ahydroxymethylene- 18-nor-D-homo-13a -etiocholane of the formula <FORM:0922315/IV(a)/5> with alkaline hydrogen peroxide, and (2) by treating 3a ,11b -diacyloxy-17 -keto-18-nor-D-homo-13a -etiocholane of the formula <FORM:0922315/IV(a)/6> (which may be prepared by acylating the corresponding free 3a ,11b -dihydroxy compound) with an organic per-acid to form the 17,18-lactone of 3a ,11b -diacyloxy-18-hydroxy-13,17-seco-13a -etiocholan-17-oic acid of the third formula above, oxidising this lactone with a mixture of chromic and sulphuric acids to form 3a ,11b -diacyloxy-13,17-seco-etiocholan-17,18-dioic acid of the fourth formula above, and treating this compound with warm alkali and then acidifying, wherein in the above processes (1) and (2) the initial reactant is prepared from 3a -hydroxy-11-keto-13,17-secoetiochol-12-en-17-oic acid or the methyl ester thereof obtainable by esterifying the acid, e.g. by reacting the acid with a mixture of sulphuric acid and methanol and which has the second formula above, by a process described in Specification 922,316.
ES0251876A 1958-10-15 1959-09-03 New compounds useful in steroid synthesis and processes for the preparation thereof Expired ES251876A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR776718 1958-10-15

Publications (1)

Publication Number Publication Date
ES251876A1 true ES251876A1 (en) 1960-01-01

Family

ID=8707738

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0251876A Expired ES251876A1 (en) 1958-10-15 1959-09-03 New compounds useful in steroid synthesis and processes for the preparation thereof

Country Status (5)

Country Link
BE (1) BE583615A (en)
CH (2) CH406199A (en)
ES (1) ES251876A1 (en)
GB (2) GB922316A (en)
SE (1) SE302300B (en)

Also Published As

Publication number Publication date
CH417581A (en) 1966-07-31
GB922316A (en) 1963-03-27
CH406199A (en) 1966-01-31
SE302300B (en) 1968-07-15
GB922315A (en) 1963-03-27
BE583615A (en) 1969-04-14

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