GB945503A - New pregnane derivatives and processes for their preparation - Google Patents

New pregnane derivatives and processes for their preparation

Info

Publication number
GB945503A
GB945503A GB485761A GB485761A GB945503A GB 945503 A GB945503 A GB 945503A GB 485761 A GB485761 A GB 485761A GB 485761 A GB485761 A GB 485761A GB 945503 A GB945503 A GB 945503A
Authority
GB
United Kingdom
Prior art keywords
bis
hydroxymethylene
dione
double bond
acyloxymethylene
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
GB485761A
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
Priority claimed from FR819007A external-priority patent/FR1363108A/en
Priority claimed from FR824171A external-priority patent/FR1363111A/en
Priority claimed from FR829006A external-priority patent/FR1363864A/en
Priority claimed from FR830527A external-priority patent/FR83002E/en
Priority claimed from FR830528A external-priority patent/FR83204E/en
Priority claimed from FR832083A external-priority patent/FR1365256A/en
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB945503A publication Critical patent/GB945503A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises compounds having the formula: <FORM:0945503/C2/1> where R1 represents =O or =OAC(H); R2 represents =O or -H(OH); Y represents two hydrogen atoms or provided that R1 represents =O, it may represent a double bond; X represents two hydrogen atoms or provided that Y is a double bond, it may represent a double bond, and -AC represents either a hydrogen atom or an acyl radical derived either from an organic carboxylic acid having 1-18 carbon atoms or from a mineral acid and processes for the preparation thereof by subjecting 3a -hydroxy-20-bis-(hydroxymethylene) -5b -pregnane -11- one (a) to reduction e.g. with LiALH4; (b) to acylation, (c) to protection of the 20-bis (hydroxymethylene) grouping e.g. with an aldehyde or ketone, followed by acylation of the 3-OH group and subsequent saponification of the protected 20-bis (hydroxymethylene) grouping to form 3a -acyloxy -20- bis (hydroxymethylene 5b -pregnan -11- one. This compound may be acylated to form a 3a -acyloxy -20- bis (acyloxymethylene) -11- one. Alternatively the 20-protected intermediate from (c) is oxidised at 3-position and saponified to obtain 20-bis-(hydroxymethylene) -5b - pregnane -3,11-dione. This compound may be acylated to form a 20-bis (acyloxymethylene) - pregnane -3,11 - dione, or a 1,2-double bond or 1,2 and 2,4-double bonds may be introduced e.g. by bromination and dehydrobromination to obtain 20-bis-(hydroxy-methylene)-pregn -4- ene -3,11-dione and 20-bis-(hydroxymethylene) - pregn -1,4 - dien -3,11-dione respectively. These compounds may subsequently be acylated to form the corresponding 20-bis (acyloxymethylene) derivatives. Specifications 832,244 and 945,501 are referred to.
GB485761A 1960-02-19 1961-02-09 New pregnane derivatives and processes for their preparation Expired GB945503A (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
FR819007A FR1363108A (en) 1960-02-19 1960-02-19 Bis-hydroxymethylene pregnane derivative and method of preparation
FR824171A FR1363111A (en) 1960-04-12 1960-04-12 Bis-hydroxymethylene pregnane derivatives and method of preparation
FR829006A FR1363864A (en) 1960-06-03 1960-06-03 Bis-hydroxymethylene pregnane derivatives and method of preparation
FR830527A FR83002E (en) 1960-06-20 1960-06-20 Bis-hydroxymethylene pregnane and process for obtaining it
FR830528A FR83204E (en) 1960-06-20 1960-06-20 Bis-hydroxymethylene pregnane derivatives and method of preparation
FR832083A FR1365256A (en) 1960-07-05 1960-07-05 Bis-hydroxymethylene pregnane derivatives and method of manufacture

Publications (1)

Publication Number Publication Date
GB945503A true GB945503A (en) 1964-01-02

Family

ID=27546150

Family Applications (1)

Application Number Title Priority Date Filing Date
GB485761A Expired GB945503A (en) 1960-02-19 1961-02-09 New pregnane derivatives and processes for their preparation

Country Status (1)

Country Link
GB (1) GB945503A (en)

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