GB1138754A - 6-oxo-diazepine derivatives - Google Patents

6-oxo-diazepine derivatives

Info

Publication number
GB1138754A
GB1138754A GB1511366A GB1511366A GB1138754A GB 1138754 A GB1138754 A GB 1138754A GB 1511366 A GB1511366 A GB 1511366A GB 1511366 A GB1511366 A GB 1511366A GB 1138754 A GB1138754 A GB 1138754A
Authority
GB
United Kingdom
Prior art keywords
chloro
phenyl
compound
tetrahydro
methylamino
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
GB1511366A
Inventor
Hans Ott
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB1138754A publication Critical patent/GB1138754A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals

Landscapes

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

Abstract

1,138,754. 6-Oxo-diazepine derivatives. SANDOZ Ltd. 5 April, 1966 [12 April, 1965], No. 15113/66. Heading C2C. Novel compounds of formula and their acid addition salts, are prepared by oxidation in manner known per se of compounds of formula wherein R is H or C 1-4 alkyl, followed by optional salt formation. A multi-step synthesis of the starting compounds is given, and is exemplified by the following:- (A) N - (# - Phenethyl) - 2 - methylamino - 5 - chloro-benzamide is prepared by reaction of 5-chloro-N-methyl-isatoic anhydride and #- phenethylamine; its amino group is protected with a p-toluenesulphonyl group and it is subjected to ring-closure with P 2 O 5 giving 1-(2- methylamino - 5 - chloro - phenyl) - 3,4 - dihydroisoquinoline, which is in turn reduced to the 1,2,3,4-tetrahydro derivative*. Subsequent treatment with ethylbromoacetate yields 1-(2- methylamino - 5 - chloro - phenyl) - 2 - carboxymethyl - 1,2,3,4 - tetrahydro - isoquinoline which is heated to effect ring-closure, giving 2-chloro- 5 - methyl - 5,6,7,9,10,14b - hexahydro - isoquinolo- [2,1-d]benzo[1,4]diazepin - 6 - one#. The compound * is a racemate, and may be resolved using d-( + ) and l-( - ) tartaric acids before subjection to the further reactions given. (B) N - (# - Phenethyl) - 2 - nitro - 5 - chlorobenzamide is prepared by reaction of 2-nitro-5- chloro-benzoyl chloride and #-phenethylamine, and is subjected to ring-closure with P 2 O 5 giving 1 - (2 - nitro - 5 - chloro - phenyl) - 3,4 - dihydroisoquinoline, which is in turn reduced to the corresponding 1,2,3,4 - tetrahydro derivative. This product is converted to 1-(2-amino-5- chloro - phenyl) - 2 - carboxymethyl - 1,2,3,4 - tetrahydro isoquinoline with ethylbromoacetate, and this in turn is heated to give the compound # above. Pharmaceutical compositions having sedative, anticonvulsant, amphetamine antagonistic or potentiation of barbiturate narcosis activity comprise a compound of the first formula given above, together with a physiologically acceptable carrier. The composition is suitably a tablet, dragÚe, syrup or injectable solution. Doses of 100-350 mg. of active agent per day are specified. A specific composition comprises the 8-N-oxide of compound # above, together with tragacanth, lactose, starch, talcum, magnesium stearate, denatured alcohol and water.
GB1511366A 1965-04-12 1966-04-05 6-oxo-diazepine derivatives Expired GB1138754A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US44752265A 1965-04-12 1965-04-12

Publications (1)

Publication Number Publication Date
GB1138754A true GB1138754A (en) 1969-01-01

Family

ID=23776703

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1511366A Expired GB1138754A (en) 1965-04-12 1966-04-05 6-oxo-diazepine derivatives

Country Status (3)

Country Link
ES (1) ES325366A1 (en)
FR (1) FR5542M (en)
GB (1) GB1138754A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000044725A1 (en) * 1999-01-28 2000-08-03 Boehringer Ingelheim Pharma Kg Fused dihydropyridines and use of fused dihydropyridines in the preparation of agents for the treatment of epilepsy

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000044725A1 (en) * 1999-01-28 2000-08-03 Boehringer Ingelheim Pharma Kg Fused dihydropyridines and use of fused dihydropyridines in the preparation of agents for the treatment of epilepsy

Also Published As

Publication number Publication date
ES325366A1 (en) 1967-04-01
FR5542M (en) 1967-11-13

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