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GB1140049A - N-substituted tetrahydrobenzazepines - Google Patents

N-substituted tetrahydrobenzazepines

Info

Publication number
GB1140049A
GB1140049A GB1467466A GB1467466A GB1140049A GB 1140049 A GB1140049 A GB 1140049A GB 1467466 A GB1467466 A GB 1467466A GB 1467466 A GB1467466 A GB 1467466A GB 1140049 A GB1140049 A GB 1140049A
Authority
GB
United Kingdom
Prior art keywords
reaction
compound
benzazepine
alkyl
give
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
GB1467466A
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.)
Alphachimie S A
Original Assignee
Alphachimie S A
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
Priority claimed from FR11779A external-priority patent/FR1472930A/en
Priority claimed from FR11778A external-priority patent/FR1473839A/en
Priority claimed from FR11780A external-priority patent/FR1473840A/en
Application filed by Alphachimie S A filed Critical Alphachimie S A
Publication of GB1140049A publication Critical patent/GB1140049A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1,140,049. Benzazepine derivatives. ALPHACHIMIE S.A. 1 April, 1966 [2 April, 1965 (3)], No. 14674/66. Heading C2C. The invention comprises compounds of formulµ wherein X is hydroben, chlorine, bromine, nitro, amino, C 1-4 alkyl or C 1-4 alkoxy and A is allyl, hydroxyalkyl, chloroalkyl, bromoalkyl, mono-lower alkylamino-alkyl, di-lower alkylammo-alkyl. pyrrolidinoalkyl. piperidinoalkyl, homopiperidinoalkyl, morpholinoalkyl, thiamorpholinoalkyl, piperazinoalkyl, N - lower alkylpiperazinoalkyl, amidoximoalkyl, guanidinoalkyl, monoalkylcarbemyl or amidino, the lower alkyl groups containing up to 3 carbon atoms and the other alkyl groups up to 6 carbon atoms, with the proviso that when A is guanidinoalkyl the alkyl group contains 1,4,5 or 6 carbon atoms when X is hydrogen, halogen or alkyl, acid addition salts thereof and their preparation by (a) reaction of an N-unsubstituted benzazepine, or an alkali metal salt thereof, with a halide, sulphate, or sulphonate derivative of a group A, (b) reaction of an N-unsubstituted benzazepine with an S-methyl-isothiouronium salt to give an N-amidino-compound, (c) reaction of an N-alkylcarbamyl compound, (d) cyclization by reaction of a halomethyl-ohalopropyl benzene or an o-di-haloethyl benzene with an amino derivative of a group A, (e) reaction of an N-aminoalkyl-benzazepine with an S-alkyl-isothiouronium salt, cyanamide or dicyanamide, a salt of 1-amidino-3,5-dimethyl-pyrazole or a cyanogen halide and ammonia to give an N-guanidinoalkyl compound, (f) reaction of a cyanoalkyl compound with a hydroxylamine salt in the presence of a base to give an amidoximealkyl compound, (g) a reaction of an N-hydroxyalkyl-benzazepine with a hydrogen halide to give an N- haloalkyl compound, or (b) reaction of an N-halo-benzazepine with a heterocyclic amine to give an N-heterocyclylalkyl compound. N-Cyanoethyl-benzazepines are prepared by reaction of an N-unsubstituted benzazepine with acrylonitrile. The compounds of the invention have central nervous system regulating activity and may be used in pharmaceutical compositions in combination with a carrier, for example in forms suitable for oral, parenteral or topical administration.
GB1467466A 1965-04-02 1966-04-01 N-substituted tetrahydrobenzazepines Expired GB1140049A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR11779A FR1472930A (en) 1965-04-02 1965-04-02 New 2, 3, 4, 5-tetrahydro- (1eta) -2-benzazepine derivatives and their manufacturing processes
FR11778A FR1473839A (en) 1965-04-02 1965-04-02 New derivatives of 2, 3, 4, 5-tetrahydro- (1h) -1-benzazepine and their manufacturing processes
FR11780A FR1473840A (en) 1965-04-02 1965-04-02 New derivatives of 2, 3, 4, 5-tetrahydro- (1h) -3-benzazepine and their manufacturing processes

Publications (1)

Publication Number Publication Date
GB1140049A true GB1140049A (en) 1969-01-15

Family

ID=27242042

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1467466A Expired GB1140049A (en) 1965-04-02 1966-04-01 N-substituted tetrahydrobenzazepines

Country Status (1)

Country Link
GB (1) GB1140049A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4701534A (en) * 1984-06-19 1987-10-20 Shell Oil Company Azetidine derivative
US5096900A (en) * 1988-07-12 1992-03-17 Synthelabo (4-piperidyl)methyl-2,3-dihydro-1h-isoindole and -2,3,4,5-tetrahydro-1h-benzazepine derivatives, their preparation and their application in therapy
FR2943667A1 (en) * 2009-03-31 2010-10-01 Servier Lab NEW PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4701534A (en) * 1984-06-19 1987-10-20 Shell Oil Company Azetidine derivative
US5096900A (en) * 1988-07-12 1992-03-17 Synthelabo (4-piperidyl)methyl-2,3-dihydro-1h-isoindole and -2,3,4,5-tetrahydro-1h-benzazepine derivatives, their preparation and their application in therapy
FR2943667A1 (en) * 2009-03-31 2010-10-01 Servier Lab NEW PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS SALTS OF ADDITION TO A PHARMACEUTICALLY ACCEPTABLE ACID
CN101851205A (en) * 2009-03-31 2010-10-06 瑟维尔实验室 S 16257-2 and with the novel synthesis of the additive salt of pharmaceutically acceptable acid
WO2010112704A1 (en) * 2009-03-31 2010-10-07 Les Laboratoires Servier Novel method for the synthesis of ivabradine and the addition salts thereof with a pharmaceutically acceptable acid
EP2241554A1 (en) * 2009-03-31 2010-10-20 Les Laboratoires Servier Process for the synthesis of ivabradine and its pharmaceutically acceptable acid addition salts
US8101747B2 (en) 2009-03-31 2012-01-24 Les Laboratoires Servier Process for the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
CN102603634A (en) * 2009-03-31 2012-07-25 瑟维尔实验室 Process for the synthesis of ivabradine and its pharmaceutically acceptable acid addition salts
CN101851205B (en) * 2009-03-31 2013-02-13 瑟维尔实验室 New process for the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
CN102603634B (en) * 2009-03-31 2014-04-16 瑟维尔实验室 Process for the synthesis of ivabradine and its pharmaceutically acceptable acid addition salts

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