GB1477950A - Heterocyclic fused triazolo benzodiazepines - Google Patents

Heterocyclic fused triazolo benzodiazepines

Info

Publication number
GB1477950A
GB1477950A GB3843975A GB3843975A GB1477950A GB 1477950 A GB1477950 A GB 1477950A GB 3843975 A GB3843975 A GB 3843975A GB 3843975 A GB3843975 A GB 3843975A GB 1477950 A GB1477950 A GB 1477950A
Authority
GB
United Kingdom
Prior art keywords
formula
group
pyridyl
alkyl
triazolobenzodiazepines
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
GB3843975A
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.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries 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 Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of GB1477950A publication Critical patent/GB1477950A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Anesthesiology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

1477950 Triazolobenzodiazepines and their pharmaceutical compositions TAKEDAYAKUHIN KOGYO KK 18 Sept 1975 [19 Sept 1974] 38439/75 Heading C2C The invention comprises compounds of Formula I wherein R<SP>1</SP> represents a hydrogen atom or an alkyl or aralkyl group; R<SP>2</SP> represents a hydrogen atom or a C 1-4 alkyl group; Y represents an ethylene or trimethylene group which may be substituted by one or more alkyl groups; Z represents an oxygen or sulphur atom or -NH- group; Ar represents a phenyl group which may have one or more substituents, or a pyridyl group and ring A is optionally substituted by a halogen atom or a nitro, alkyl, trifluoromethyl or alkoxy group which may be prepared by reaction of a compound of Formula II wherein X is a halogen atom or an active ester of a hydroxy group with a compound of formula HZ-Y-NH 2 . 2 - Amino - 5 - (2 - pyridyl) - 3,H - 1,4 - benzodiazepine 4N - oxide and the corresponding 7- bromo analogue are prepared by reacting 2- chloromethyl - 4 - (2 - pyridyl)quinazoline 3N-oxide and its 6-bromo analogue with saturated ammoniacal ethanol and these products are reacted with an alkyl ortho ester of Formula R<SP>1</SP>-C(OR<SP>1</SP>) 3 to obtain the 2-(1-ethoxyethylideneamino) - 5 - (2 - pyridyl) - 3H, - 1,4 - benzodiazepine 4N-oxides of Formula (d) wherein R<SP>1</SP> is CH 3 or C 2 H 5 , R<SP>2</SP> is H, Ar is 2- pyridyl and ring A is unsubstituted or subsituted by bromine which are reacted with ammonia in ethanol to obtain the corresponding amino alkylidene compounds of Formula (e) which are in turn cyclized by treatment with sodium hypochlorite to obtain the corresponding triazolobenzodiazepines of Formula (f) 1 - (2 - Benzoyl - 4 - chlorophenyl) - 3 - methyl- 5 - chloromethyl - 1H - 1,2,4 - triazole and 1 - [4 - bromo - 2- (2 - pyridinecarbonyl)phenyl]- 5 - chloromethyl - 3 - ethyl - 1H - 1,2,4 - triazole are prepared by reaction of the corresponding triazolobenzodiazepines of Formula (f) (above) with sodium nitrite and hydrochloric acid. Pharmaceutical compositions having muscle relaxant, anticonvulsant, sedative, antianxiety, tranquillizing and sleep inducing effects for oral or parenteral administration comprise a compound of Formula I together with a pharmaceutically acceptable carrier or diluent.
GB3843975A 1974-09-19 1975-09-18 Heterocyclic fused triazolo benzodiazepines Expired GB1477950A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP49108502A JPS5136499A (en) 1974-09-19 1974-09-19 Ikokankagobutsu no seizoho

Publications (1)

Publication Number Publication Date
GB1477950A true GB1477950A (en) 1977-06-29

Family

ID=14486389

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3843975A Expired GB1477950A (en) 1974-09-19 1975-09-18 Heterocyclic fused triazolo benzodiazepines

Country Status (4)

Country Link
JP (1) JPS5136499A (en)
DE (1) DE2541959A1 (en)
FR (1) FR2285136A1 (en)
GB (1) GB1477950A (en)

Also Published As

Publication number Publication date
FR2285136B1 (en) 1980-05-16
JPS5136499A (en) 1976-03-27
JPS5751397B2 (en) 1982-11-01
FR2285136A1 (en) 1976-04-16
DE2541959A1 (en) 1976-04-01

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee