GB680952A - Improvements in new morphine derivatives and production thereof - Google Patents

Improvements in new morphine derivatives and production thereof

Info

Publication number
GB680952A
GB680952A GB19751/50A GB1975150A GB680952A GB 680952 A GB680952 A GB 680952A GB 19751/50 A GB19751/50 A GB 19751/50A GB 1975150 A GB1975150 A GB 1975150A GB 680952 A GB680952 A GB 680952A
Authority
GB
United Kingdom
Prior art keywords
ether
production
dibromomethylate
ethers
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
GB19751/50A
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.)
LAB DAUSSE
Original Assignee
LAB DAUSSE
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 LAB DAUSSE filed Critical LAB DAUSSE
Publication of GB680952A publication Critical patent/GB680952A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
    • C07D489/08—Oxygen atom

Abstract

The invention comprises morphine ethers of the formula <FORM:0680952/IV (b)/1> where R1 and R2 are C1-C3 alkyl groups or form a ring with the nitrogen atom; also acid and diquaternary ammonium salts thereof. These are prepared by reacting morphine with a halide R1R2N-CH2-CH2-Hal or hydrohalide salt thereof in the presence of alkali sufficient to neutralize all the hydrogen halide split off. The basic ether may then be reacted with an acid, followed if desired by double decomposition in alcoholic solution, or with an alkylating agent in a solvent. The reactions are preferably carried out in the absence of oxygen. Examples show the production of the dimethylamino-ethyl ether, the diethylaminoethyl ether and its dibromomethylate, the morpholylethyl ether and its dibromomethylate and di-iodomethylate, and the piperidylethyl ether. The hydrochloride, phosphate and phenylacetate of the last two ethers are described.
GB19751/50A 1949-08-30 1950-08-08 Improvements in new morphine derivatives and production thereof Expired GB680952A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR680952X 1949-08-30

Publications (1)

Publication Number Publication Date
GB680952A true GB680952A (en) 1952-10-15

Family

ID=9022556

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19751/50A Expired GB680952A (en) 1949-08-30 1950-08-08 Improvements in new morphine derivatives and production thereof

Country Status (1)

Country Link
GB (1) GB680952A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1017618B (en) * 1953-10-15 1957-10-17 Dausse Sa Lab Process for the preparation of the morpholylaethyl ether of morphine and its salts
DE1172267B (en) * 1961-09-19 1964-06-18 Dausse S A Lab Process for the preparation of the bis-guaiacol-sulfonic acid salt of morphine-ª ‰ -morpholyl-ethyl-ether
US3888864A (en) * 1973-06-29 1975-06-10 Hoffmann La Roche Amino lower alkyl ether derivatives of opium alkaloids
CN109336895A (en) * 2018-11-08 2019-02-15 宜昌人福药业有限责任公司 A kind of synthetic method of pholcodine

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1017618B (en) * 1953-10-15 1957-10-17 Dausse Sa Lab Process for the preparation of the morpholylaethyl ether of morphine and its salts
DE1172267B (en) * 1961-09-19 1964-06-18 Dausse S A Lab Process for the preparation of the bis-guaiacol-sulfonic acid salt of morphine-ª ‰ -morpholyl-ethyl-ether
US3888864A (en) * 1973-06-29 1975-06-10 Hoffmann La Roche Amino lower alkyl ether derivatives of opium alkaloids
CN109336895A (en) * 2018-11-08 2019-02-15 宜昌人福药业有限责任公司 A kind of synthetic method of pholcodine

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