GB991593A - Cis-syn-trans steroid and d-homo-steroid compounds having an aromatic ring a - Google Patents

Cis-syn-trans steroid and d-homo-steroid compounds having an aromatic ring a

Info

Publication number
GB991593A
GB991593A GB702960A GB702960A GB991593A GB 991593 A GB991593 A GB 991593A GB 702960 A GB702960 A GB 702960A GB 702960 A GB702960 A GB 702960A GB 991593 A GB991593 A GB 991593A
Authority
GB
United Kingdom
Prior art keywords
trans
compound
syn
steroid
choh
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
GB702960A
Inventor
Gordon Alan Hughes
Herchel Smith
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB702960A priority Critical patent/GB991593A/en
Priority to CH185361A priority patent/CH398586A/en
Priority to DES72617A priority patent/DE1214679B/en
Priority to SE206361A priority patent/SE307946B/xx
Priority to AT156261A priority patent/AT256350B/en
Priority to DK89061A priority patent/DK105529C/en
Publication of GB991593A publication Critical patent/GB991593A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J1/00Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J63/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008Expansion of ring D by one atom, e.g. D homo steroids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises cis-syn-trans steroid compounds of formula <FORM:0991593/C2/1> wherein R is H, alkyl or acyl, R1 is C2- 20-alkyl, Y is C = O (optionally ketalized) or CHOH and the atoms H are trans. to R1 and specifically those wherein (1) R is CH3, Y is C = O and R1 is ethyl (a), isopropyl or cetyl; (2) R is CH3, Y is CHOH(a) or ethylenedioxymethylene (b) and R1 is ethyl; (3) R is H, Y is C = O and R1 is ethyl; the compound in which Y is CHOH and R = R1 = CH3 is also claimed. These compounds are prepared by a process for preparing generally a cis-syn-trans compound of formula <FORM:0991593/C2/2> by catalytic hydrogenation of a compound of formula <FORM:0991593/C2/3> wherein R is H, alkyl or acyl, R1 is alkyl, Y is C = O, CHOH or a derivative group convertible by hydrolysis thereto, Q is CH2 or CH2CH2 and T is an ethylenic linkage or a saturated C-C bond with an H atom at the 14-position trans to R1. Compound (3) is made alternatively by splitting the ether group in (1) (a), and the latter by reacting 2 (b) with HCl. The process of the invention is also exemplified for the case in which (first formula) R is acetyl, Y is C = O and R1 is CH3; the product is hydrolysed to the corresponding compound (R = H). No examples are given for the D-homosteroids.
GB702960A 1960-02-29 1960-02-29 Cis-syn-trans steroid and d-homo-steroid compounds having an aromatic ring a Expired GB991593A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB702960A GB991593A (en) 1960-02-29 1960-02-29 Cis-syn-trans steroid and d-homo-steroid compounds having an aromatic ring a
CH185361A CH398586A (en) 1960-02-29 1961-02-16 Process for the production of estrone derivatives
DES72617A DE1214679B (en) 1960-02-29 1961-02-18 Process for the preparation of 13-alkyl-8-isogonane compounds or of their D-homoanalogues
SE206361A SE307946B (en) 1960-02-29 1961-02-27
AT156261A AT256350B (en) 1960-02-29 1961-02-27 Process for the production of 8-iso-19-norsteroids, as well as of new compounds of this group
DK89061A DK105529C (en) 1960-02-29 1961-02-28 Process for the preparation of 3-hydroxy-, 3-alkoxy- or 3-acyloxy-Δ <1,3,5 (10)> steroid or D-homosteroid compounds.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB702960A GB991593A (en) 1960-02-29 1960-02-29 Cis-syn-trans steroid and d-homo-steroid compounds having an aromatic ring a

Publications (1)

Publication Number Publication Date
GB991593A true GB991593A (en) 1965-05-12

Family

ID=9825282

Family Applications (1)

Application Number Title Priority Date Filing Date
GB702960A Expired GB991593A (en) 1960-02-29 1960-02-29 Cis-syn-trans steroid and d-homo-steroid compounds having an aromatic ring a

Country Status (6)

Country Link
AT (1) AT256350B (en)
CH (1) CH398586A (en)
DE (1) DE1214679B (en)
DK (1) DK105529C (en)
GB (1) GB991593A (en)
SE (1) SE307946B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3549673A (en) * 1967-03-09 1970-12-22 Takeda Chemical Industries Ltd Total synthesis of 13beta-substituted gonapolyen-17alpha-ols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3549673A (en) * 1967-03-09 1970-12-22 Takeda Chemical Industries Ltd Total synthesis of 13beta-substituted gonapolyen-17alpha-ols

Also Published As

Publication number Publication date
DE1214679B (en) 1966-04-21
SE307946B (en) 1969-01-27
AT256350B (en) 1967-08-10
CH398586A (en) 1966-03-15
DK105529C (en) 1966-10-10

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