GB1118688A - Novel benzazepines and process for making same - Google Patents

Novel benzazepines and process for making same

Info

Publication number
GB1118688A
GB1118688A GB763267A GB763267A GB1118688A GB 1118688 A GB1118688 A GB 1118688A GB 763267 A GB763267 A GB 763267A GB 763267 A GB763267 A GB 763267A GB 1118688 A GB1118688 A GB 1118688A
Authority
GB
United Kingdom
Prior art keywords
phenyl
benzazepine
tetrahydro
prepared
ethyl
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
GB763267A
Inventor
Lewis A Walter
Wei K Chang
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.)
Scherico Ltd
Original Assignee
Scherico Ltd
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 Scherico Ltd filed Critical Scherico Ltd
Priority to GB763267A priority Critical patent/GB1118688A/en
Publication of GB1118688A publication Critical patent/GB1118688A/en
Priority to CY63872A priority patent/CY638A/en
Priority to MY7300021A priority patent/MY7300021A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Novel 1 - phenyl - 2,3,4,5 - tetrahydro - 1H, 3-benzazepine derivatives having hydrogen, alkyl, hydroxyalkyl containing two or more carbon atoms, alkenyl or benzyl attached to the nitrogen atom (radical R below), especially compounds of the general formula <FORM:1118688/C2/1> wherein each of X and Y is H, hydroxy, alkyl, alkoxy or halogen or, taken together, alkylene dioxy, A is phenyl or substituted phenyl, R is as above defined and each of R1 and R2 is H or alkyl; and the pharmaceutically acceptable acid addition and quaternary ammonium salts thereof are prepared by (a) cyclizing a suitable phenethylaminomethylbenzyl derivative or an o-benzyl derivative of a phenethylamide compound, (b) reducing a suitable 2-oxo-benzazepine or (c) alkylation etc. at the 3-position. N - [(b - Hydoxy - b - phenyl)ethyl] - 2-phenylethylamine, N - [(b - hydroxy - b - phenyl)ethyl] - 2 - (3141 - dimethoxy) - phenylethylamine and N - [(b - hydroxy - b - phenyl)ethyl] - 2 - phenylisopropylamine are prepared from styrene oxide and phenethylamine, homoveratrylamine and d-amphetamine respectively, and a -methyl-a -phenethylaminomethyl benzyl alcohol from a -methylstyrene and phenethylamine. N - (b - p - Methoxyphenethyl)mandelamide is prepared from b -p-methoxyphenethylamine and mandelic acid and then treated with polyphosphoric acid to give 1-phenyl-2-oxo-7-methoxy - 2,3,4,5 - tetrahydro - 1H,3 - benzazepine. N - (3,4 - Dimethoxy - 6 - phenylacetic acidethyl ester - phenethyl)acetamide is prepared from N-(3,4-dimethoxyphenethyl)acetamide and ethyl mandelate and heated to give 1-phenyl-7,8-dimethoxy - 2 - ox - 2,3,4,5 - tetrahydro - 1H,3-benzazepine. A racemic mixture of 1-phenyl-2,3,4,5-tetrahydro-1H,3-benzazepine is resolved with phenylsuccinic acid. Pharmaceutical compositions comprise, as active ingredient a novel compound of the above general formula or an acid addition or a quaternary ammonium salt thereof and a carrier. The compositions are stated to have anti - depressant, analgesic and hypotensive activity.
GB763267A 1967-02-17 1967-02-17 Novel benzazepines and process for making same Expired GB1118688A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB763267A GB1118688A (en) 1967-02-17 1967-02-17 Novel benzazepines and process for making same
CY63872A CY638A (en) 1967-02-17 1972-05-02 Novel benzazepines and process for making same
MY7300021A MY7300021A (en) 1967-02-17 1973-12-30 Novel benzazepines and process for making same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB763267A GB1118688A (en) 1967-02-17 1967-02-17 Novel benzazepines and process for making same

Publications (1)

Publication Number Publication Date
GB1118688A true GB1118688A (en) 1968-07-03

Family

ID=9836840

Family Applications (1)

Application Number Title Priority Date Filing Date
GB763267A Expired GB1118688A (en) 1967-02-17 1967-02-17 Novel benzazepines and process for making same

Country Status (3)

Country Link
CY (1) CY638A (en)
GB (1) GB1118688A (en)
MY (1) MY7300021A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4881882A (en) * 1972-02-01 1973-11-01
FR2315934A1 (en) * 1975-07-02 1977-01-28 Smithkline Corp PHARMACEUTICAL COMPOSITIONS BASED ON DIAZEPINE DERIVATIVES
DE2751258A1 (en) * 1976-11-17 1978-06-01 Smithkline Corp TRISUBSTITUTED 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE AND THE SALTS THEREOF, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
US4108989A (en) 1977-04-01 1978-08-22 Smithkline Corporation 2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones
EP0005300A1 (en) * 1978-05-08 1979-11-14 Technobiotic Ltd. Substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines, process for the preparation thereof, and pharmaceutical compositions containing them
US4541954A (en) * 1984-09-05 1985-09-17 Smithkline Beckman Corporation Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
EP0230270A2 (en) 1986-01-16 1987-07-29 Schering Corporation Fused benzazepines
WO1990000853A2 (en) 1988-07-18 1990-02-08 Schering Corporation Method of treating neurological disorders
US5015639A (en) * 1987-03-27 1991-05-14 Schering Corporation Substituted benzazepines, their preparation and pharmaceutical compositions containing them
US5302716A (en) * 1986-01-16 1994-04-12 Schering Corporation Fused benzazepines
US5362728A (en) * 1990-02-02 1994-11-08 Schering Corporation 4,5-bridged-2,3,4,5-tetrahydro-1H-3-benzazepine-7-ols and derivatives and compositions and methods employing such compounds

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4881882A (en) * 1972-02-01 1973-11-01
FR2315934A1 (en) * 1975-07-02 1977-01-28 Smithkline Corp PHARMACEUTICAL COMPOSITIONS BASED ON DIAZEPINE DERIVATIVES
DE2751258A1 (en) * 1976-11-17 1978-06-01 Smithkline Corp TRISUBSTITUTED 1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE AND THE SALTS THEREOF, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
US4160765A (en) * 1976-11-17 1979-07-10 Smithkline Corporation Method for 6-bromination of 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds
US4108989A (en) 1977-04-01 1978-08-22 Smithkline Corporation 2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones
EP0005300A1 (en) * 1978-05-08 1979-11-14 Technobiotic Ltd. Substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines, process for the preparation thereof, and pharmaceutical compositions containing them
US4541954A (en) * 1984-09-05 1985-09-17 Smithkline Beckman Corporation Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
EP0230270A2 (en) 1986-01-16 1987-07-29 Schering Corporation Fused benzazepines
US4973586A (en) * 1986-01-16 1990-11-27 Schering Corporation Fused benzazepines, compositions of, and medical use thereof
US5302716A (en) * 1986-01-16 1994-04-12 Schering Corporation Fused benzazepines
US5015639A (en) * 1987-03-27 1991-05-14 Schering Corporation Substituted benzazepines, their preparation and pharmaceutical compositions containing them
WO1990000853A2 (en) 1988-07-18 1990-02-08 Schering Corporation Method of treating neurological disorders
US5362728A (en) * 1990-02-02 1994-11-08 Schering Corporation 4,5-bridged-2,3,4,5-tetrahydro-1H-3-benzazepine-7-ols and derivatives and compositions and methods employing such compounds

Also Published As

Publication number Publication date
MY7300021A (en) 1973-12-31
CY638A (en) 1972-05-02

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