GB1233193A - - Google Patents

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Publication number
GB1233193A
GB1233193A GB1233193DA GB1233193A GB 1233193 A GB1233193 A GB 1233193A GB 1233193D A GB1233193D A GB 1233193DA GB 1233193 A GB1233193 A GB 1233193A
Authority
GB
United Kingdom
Prior art keywords
isoquinoline
derivatives
ethyl
octahydro
methoxybenzyl
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
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 filed Critical
Publication of GB1233193A publication Critical patent/GB1233193A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18—Aralkyl radicals
    • C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1,233,193. Morphinan derivatives. F. HOFFMANN-LA ROCHE & CO. A.G. 22 Aug., 1968 [25 Aug., 1967], No. 40125/68. Heading C2C. Morphinan derivatives of the formula in which R represents a C 1-8 alkyl, C 1-6 alkanoyl or optionally substituted benzoyl or naphthoyl group and R<SP>1</SP> represents a cyano, nitro, nitroso, C 1-8 alkylsulphonyl, an arylsulphonyl or the group -CO-[H or R<SP>2</SP>], where R<SP>2</SP> is C 1-8 alkyl, aryl, C 1-8 alkoxy, aryloxy, amino, C 1-8 alkylamino, arylamino, di - (C 1-8 alkyl)amino, diarylamino or N - C 1-8 alkyl - N - arylamino, or compounds in which R 1 is replaced by methyl or ethyl groups, are prepared by treating isoquinoline derivatives of the formulµ where R 1 is other than methyl or ethyl, with an acidic cyclising agent and, if desired, converting the resultant morphinan into a compound in which R 1 is methyl or ethyl by hydrolysis and subsequent methylation or ethylation or by reduction of the compounds in which R 1 is formyl or acetyl. Specified cyclising agents include organic and inorganic acids of which H 3 PO 4 , polyphosphoric acid and mixtures of H 3 PO 4 and H 2 SO 4 are preferred. Hydrolysis to obtain compounds in which R 1 is hydrogen may be effected with an acid or a base, e.g. NaOH, and the product methylated by reaction with formaldehyde and hydrogen over Raney Ni. Reduction of the N-formyl and N-acetyl derivatives can be achieved using LiAlH 4 . Optically active morphinans can be obtained by resolution of a racemic product or by using an optically active isoquinoline reactant. Examples relate to the preparation of N-formyl, N- methyl, N - acetyl, N - ethyl, N - ethoxycarbonyl, N - carbamoyl and N - benzoyl derivatives of 3-methoxy morphinan. 1 - (p - Methoxybenzyl) - 2 - acetyl - 1,2,3,4,5, 6,7,8 - octahydro - isoquinoline is prepared by N-acetylation using acetic anhydride. 1-(p- Methoxybenzyl) - 2 - ethoxycarbonyl - 1,2,3,4,5,6, 7,8 - octahydro - isoquinoline is obtained from the corresponding compound and ethyl chloroformate. 1-(p-Methoxybenzyl) - 2 - carbamoyl - 1,2,3,4,5,6,7,8 - octahydro-isoquinoline is obtained from the corresponding compound and urea. 1-(p-Methoxybenzyl)-2- benzoyl - 1,2,3,4,5,6,7,8 - octahydro - isoquinoline is prepared by acylation using benzoyl chloride.
GB1233193D 1967-08-25 1968-08-22 Expired GB1233193A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US66321067A 1967-08-25 1967-08-25

Publications (1)

Publication Number Publication Date
GB1233193A true GB1233193A (en) 1971-05-26

Family

ID=24660890

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1233194D Expired GB1233194A (en) 1967-08-25 1968-08-22
GB1233193D Expired GB1233193A (en) 1967-08-25 1968-08-22

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1233194D Expired GB1233194A (en) 1967-08-25 1968-08-22

Country Status (8)

Country Link
BE (1) BE719788A (en)
CH (2) CH560194A5 (en)
DE (1) DE1795193C2 (en)
DK (1) DK129238B (en)
FR (1) FR1584396A (en)
GB (2) GB1233194A (en)
NL (1) NL158791B (en)
SE (1) SE364511B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5260286A (en) * 1992-10-16 1993-11-09 Japan Tobacco, Inc. 2-piperidinecarboxylic acid derivatives useful as NMDA receptor antagonists

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2327737A1 (en) * 1972-07-07 1974-01-24 Hoffmann La Roche PROCESS FOR PRODUCING ISOMORPHINANS
US4003903A (en) * 1975-02-12 1977-01-18 Florida Board Of Regents N-acyl-N-norsalutaridines and process for making them
FI773636A (en) * 1976-12-06 1978-06-07 Hoffmann La Roche NYA FENYLDERIVAT
US4194044A (en) 1976-12-06 1980-03-18 Hoffmann-La Roche Inc. Process for preparing 3-phenoxy morphinans
US4668685A (en) * 1984-07-05 1987-05-26 E.I. Du Pont De Nemours And Company Substituted benzoate ester prodrug derivatives of 3-hydroxymorphinans, which are analgesics or narcotic antagonists
CH657007GA3 (en) * 1984-08-23 1986-08-15 Tissot Sa
CH684619B5 (en) * 1992-07-17 1995-05-15 Longines Montres Comp D Timepiece universal time display.
US5905153A (en) * 1996-10-02 1999-05-18 Roche Vitamins Inc. Process for preparing (9α,13α,14α)-1-(3-methoxy-morphinan-17-yl)alkanones
EP0834506B1 (en) * 1996-10-02 2004-01-14 F. Hoffmann-La Roche Ag Process for the preparation of (9alpha, 13alpha, 14alpha)-1-(3-Methoxymorphinan-17-yl)alkanones
EP3712714B1 (en) 2019-03-19 2022-11-30 Omega SA Dial for a universal watch

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5260286A (en) * 1992-10-16 1993-11-09 Japan Tobacco, Inc. 2-piperidinecarboxylic acid derivatives useful as NMDA receptor antagonists

Also Published As

Publication number Publication date
NL6811979A (en) 1969-02-27
FR1584396A (en) 1969-12-19
SE364511B (en) 1974-02-25
DK129238C (en) 1975-02-03
GB1233194A (en) 1971-05-26
CH560194A5 (en) 1975-03-27
BE719788A (en) 1969-02-24
NL158791B (en) 1978-12-15
DK129238B (en) 1974-09-16
DE1795193C2 (en) 1984-08-23
DE1795193A1 (en) 1971-12-30
CH543514A (en) 1973-10-31

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years