GB930975A - New fused polycyclic hydrocarbon derivatives and processes for their preparation - Google Patents

New fused polycyclic hydrocarbon derivatives and processes for their preparation

Info

Publication number
GB930975A
GB930975A GB925/62A GB92562A GB930975A GB 930975 A GB930975 A GB 930975A GB 925/62 A GB925/62 A GB 925/62A GB 92562 A GB92562 A GB 92562A GB 930975 A GB930975 A GB 930975A
Authority
GB
United Kingdom
Prior art keywords
acyloxy
des
estr
ketal
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
GB925/62A
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
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB930975A publication Critical patent/GB930975A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Landscapes

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

Abstract

The invention comprises 17b -acyloxy-des-A-estr-9-ene-5-one derivatives of the general formula: <FORM:0930975/IV(a)/1> where R indicates =O or (a -H)OH and Ac represents an acyl radical derived from an organic carboxylic acid, preferably a benzoyl radical. The 5-cyclic-ketals of 17b -acyloxy-des-A-estr-9(II)-en-5-ones and of 17b -acyloxy - 9a ,11a -epoxy-des-A-estran-5-ones are also novel compounds. The 17b -acyloxy-des-A-estr-9-en-5-one derivatives are made reacting a 17b -acyloxy-des-A-estr-9-en-5-one with a ketalizing agent, e.g. ethylene glycol in the presence of p-toluene sulphonic acid, to form the 5-cyclic ketal which is reacted with an epoxidizing agent, e.g., perphthalic acid, to yield the corresponding epoxy compound, and the latter is treated with an acid reagent, e.g. a mixture of acetic acid, ethyl acetate and water, to open the epoxide bridge and hydrolyse the ketal yielding the 11-hydroxy-17b -acyloxy-des-A-estr-9-en-5-one of the above general formula where R is (a -H)OH. This product may be treated with an oxidising agent, such as manganese dioxide, to yield the 17b -acyloxy-des-A-estr-9-ene-5,11-dione having the above general formula where R is =O. Detailed examples are given in which the benzyloxy derivatives are formed and the ketal is the ethylene ketal. Other acyloxy substituents mentioned are acetoxy, trimethylacetoxy, propionyloxy, b - cyclopentylpropionyloxy phenylpropionyloxy, 4,4 - dimethylpentanoyloxy, 10-undecanonyloxy and hexahydrobenzoyloxy. The propylene ketal is also mentioned.
GB925/62A 1961-01-13 1962-01-10 New fused polycyclic hydrocarbon derivatives and processes for their preparation Expired GB930975A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR849597A FR1304009A (en) 1961-01-13 1961-01-13 New tricyclic compounds and method of preparation

Publications (1)

Publication Number Publication Date
GB930975A true GB930975A (en) 1963-07-10

Family

ID=8746661

Family Applications (1)

Application Number Title Priority Date Filing Date
GB925/62A Expired GB930975A (en) 1961-01-13 1962-01-10 New fused polycyclic hydrocarbon derivatives and processes for their preparation

Country Status (7)

Country Link
BE (1) BE612588A (en)
CH (1) CH407106A (en)
DE (2) DE1286029B (en)
DK (1) DK114827B (en)
ES (1) ES273575A1 (en)
FR (1) FR1304009A (en)
GB (1) GB930975A (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1247966A (en) * 1959-10-13 1960-12-09 Chimiotherapie Lab Franc epoxy-derivatives of cyclopentanonaphthalene and process for their preparation

Also Published As

Publication number Publication date
DE1287070C2 (en) 1969-09-04
DE1286029B (en) 1969-01-02
ES273575A1 (en) 1962-03-16
DE1287070B (en) 1969-01-16
CH407106A (en) 1966-02-15
DK114827B (en) 1969-08-11
BE612588A (en) 1962-07-12
FR1304009A (en) 1962-09-21

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