GB1397035A - Process for the manufacture of isomorphinans - Google Patents

Process for the manufacture of isomorphinans

Info

Publication number
GB1397035A
GB1397035A GB3221073A GB3221073A GB1397035A GB 1397035 A GB1397035 A GB 1397035A GB 3221073 A GB3221073 A GB 3221073A GB 3221073 A GB3221073 A GB 3221073A GB 1397035 A GB1397035 A GB 1397035A
Authority
GB
United Kingdom
Prior art keywords
alkyl
proton
alkanoyl
carbamoyl
cycloalkyl
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
GB3221073A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1397035A publication Critical patent/GB1397035A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/28—Morphinans

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1397035 Isomorphinan manufacture F HOFFMANN-LA ROCHE & CO AG 6 July 1973 [7 July 1972] 32210/73 Heading C2C Isomorphinans and salts thereof, are obtained by cyclizing an optionally substituted 1-benzyl 1,2,3,4,5,6,7,8-octahydro-isoquinoline, 1-benzyl- 1,2,3,4,6,7,8,9-octahydro-isoquinoline or 1- benzyl-decahydro-4a-isoquinolol in liquid phase with a mixture of boron trifluoride and a proton/ hydronium ion donor, and in optional sequence, isolating the isomorphina form from the morphinan form if desired, cleaving off or introducing a substituent if desired, resolving a racemate obtained into the optical antipodes if desired and, also if desired, converting a product obtained into a salt. In particular isomorphans of the general formula (I) wherein R 1 is C 1-8 alkyl, C 3-8 cycloalkyl, C 4-8 cycloalkyl-alkyl, C 2-8 alkenyl, C 2-8 alkynyl or C 1-8 alkanoyl and R 2 is C 1-8 alkyl, C 3-8 cycloalkyl, C 4-8 cycloalkylalkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 1-8 alkanoyl, benzoyl, phenyl-C 1-8 alkanoyl, C 1-8 -alkoxycarbonyl, phenoxycarbonyl, phenyl-C 1-8 alkoxycarbonyl, carbamoyl, C 1-8 alkyl-carbamoyl, or di-(C 1-8 alkyl) carbamoyl, and salts thereof, is obtained as above by cyclization of a starting material of the formula The term "proton/hydronium ion donor)" means the reagent acts either as a proton donor or as a proton and hydronium ion donor, and includes mineral acids, C 1-4 alkanols, C 1-4 alkanecarboxylic acids and C 1-4 nitroalkanes. Water can also be used, optionally with a hydrogen halide. The products have analgesic activity or are useful as intermediates for compounds having pharmacological activity. Reference has been directed by the Comptroller to Specification 1,233,193.
GB3221073A 1972-07-07 1973-07-06 Process for the manufacture of isomorphinans Expired GB1397035A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1020272 1972-07-07

Publications (1)

Publication Number Publication Date
GB1397035A true GB1397035A (en) 1975-06-11

Family

ID=4360534

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3221073A Expired GB1397035A (en) 1972-07-07 1973-07-06 Process for the manufacture of isomorphinans

Country Status (6)

Country Link
JP (1) JPS4942679A (en)
BE (1) BE801984A (en)
DE (1) DE2327737A1 (en)
FR (1) FR2192103B1 (en)
GB (1) GB1397035A (en)
NL (1) NL7308437A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2631145C2 (en) * 1976-07-10 1981-09-24 Bayer Ag, 5090 Leverkusen Method and device for applying a layer of a liquid, foamable reaction mixture to a continuously conveyed support

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH543514A (en) * 1967-08-25 1973-10-31 Hoffmann La Roche Process for the preparation of morphinane derivatives

Also Published As

Publication number Publication date
NL7308437A (en) 1974-01-09
FR2192103A1 (en) 1974-02-08
DE2327737A1 (en) 1974-01-24
FR2192103B1 (en) 1976-05-07
BE801984A (en) 1974-01-07
JPS4942679A (en) 1974-04-22

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Legal Events

Date Code Title Description
CSNS Application of which complete specification have been accepted and published, but patent is not sealed