GB956592A - Improvements in or relating to trifluoromethyl-1,4-benzodiazepine derivatives - Google Patents

Improvements in or relating to trifluoromethyl-1,4-benzodiazepine derivatives

Info

Publication number
GB956592A
GB956592A GB1301161A GB1301161A GB956592A GB 956592 A GB956592 A GB 956592A GB 1301161 A GB1301161 A GB 1301161A GB 1301161 A GB1301161 A GB 1301161A GB 956592 A GB956592 A GB 956592A
Authority
GB
United Kingdom
Prior art keywords
trifluoromethyl
alkyl
general formula
acid addition
halogen atom
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
GB1301161A
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories 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 Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB956592A publication Critical patent/GB956592A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/20—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0956592/C2/1> (wherein R1 is a hydrogen atom or a C1-4 alkyl, C2-4 alkenyl, hydroxy-C1-4 alkyl, C1-4 alkoxy-C1-4 alkyl, benzyl or phenethyl group, R2 is a hydrogen atom or a C1-4 alkyl group, and R3 is a hydrogen or halogen atom or a trifluoromethyl, methyl or methoxy group) and pharmaceutically-acceptable acid addition salts thereof, and their preparation by reacting a trifluoromethylquinazoline of the general formula <FORM:0956592/C2/2> (wherein X is a halogen atom) with R1NH2, optionally followed by acid addition salt formation. The processes of the examples are summarized in the following reaction scheme: The compounds of the invention have central nervous system activity and are useful as ataractic, antidepressant and tranquilizing agents; they also have anticonvulsant and muscle relaxant activity. <FORM:0956592/C2/3> The trifluoromethyl-substituted o-aminobenzophenone starting materials are prepared (a) from the corresponding trifluoromethyl-o-nitroaniline via the trifluoromethyl-o-nitrobenzonitrile and trifluoromethyl-o-aminobenzonitrile, or (b) by the following process: <FORM:0956592/C2/4>
GB1301161A 1960-04-20 1961-04-11 Improvements in or relating to trifluoromethyl-1,4-benzodiazepine derivatives Expired GB956592A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US2338660A 1960-04-20 1960-04-20

Publications (1)

Publication Number Publication Date
GB956592A true GB956592A (en) 1964-04-29

Family

ID=21814782

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1301161A Expired GB956592A (en) 1960-04-20 1961-04-11 Improvements in or relating to trifluoromethyl-1,4-benzodiazepine derivatives

Country Status (2)

Country Link
DE (1) DE1445134A1 (en)
GB (1) GB956592A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2034577A1 (en) * 1969-02-28 1970-12-11 Upjohn Co
US3649617A (en) * 1970-07-20 1972-03-14 Upjohn Co 2-substituted amino-5-phenyl-3h-1 4-benzodiazepines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2034577A1 (en) * 1969-02-28 1970-12-11 Upjohn Co
US3649617A (en) * 1970-07-20 1972-03-14 Upjohn Co 2-substituted amino-5-phenyl-3h-1 4-benzodiazepines

Also Published As

Publication number Publication date
DE1445134A1 (en) 1968-10-24

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