GB1383220A - Triazole derivatives and the manufacture thereof - Google Patents

Triazole derivatives and the manufacture thereof

Info

Publication number
GB1383220A
GB1383220A GB3358972A GB3358972A GB1383220A GB 1383220 A GB1383220 A GB 1383220A GB 3358972 A GB3358972 A GB 3358972A GB 3358972 A GB3358972 A GB 3358972A GB 1383220 A GB1383220 A GB 1383220A
Authority
GB
United Kingdom
Prior art keywords
triazoles
aminomethyl
benzoylphenyl
benzylphenyl
triazole
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
GB3358972A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB1383220A publication Critical patent/GB1383220A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/116—Heterocyclic compounds
    • 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
    • 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
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • 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
    • 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
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biomedical Technology (AREA)
  • Veterinary Medicine (AREA)
  • Neurosurgery (AREA)
  • Polymers & Plastics (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Pain & Pain Management (AREA)
  • Food Science & Technology (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

1383220 3 - Aminomethyl - 4 - (o - benzyl- and benzoyl - phenyl) - 4H - 1,2,4 - triazoles UPJOHN CO 18 July 1972 [18 Aug 1971] 33589/72 Heading C2C 3 - Aminomethyl - 4 - (o - benzoylphenyl)- 4H-1,2,4-triazoles and novel 3-aminomethyl-4- (o-benzylphenyl)-4H-1,2,4-triazoles of the respective general formulae wherein R 1 is a hydrogen atom or a C 1-3 alkyl, C 3-8 cycloalkyl, phenyl, benzyl or -COOR<SP>1</SP> group (R<SP>1</SP> is a C 1-3 alkyl group) or a heterocyclic aromatic group of 5 or 6 ring atoms, 1-4 of which are selected from O, N and S, each of R<SP>11</SP> and R<SP>111</SP> is a C 1-3 alkyl group or R<SP>11</SP> R<SP>111</SP>N is a pyrrolidino, piperidino or morpholino group, and each of R 2 , R 3 , R 4 and R 5 is a hydrogen or halogen atom or a C 1-3 alkyl, nitro, cyano, trifluoromethyl, C 1-3 alkoxy, C 1-3 alkylthio, C 1-3 alkylsulphinyl, C 1-3 alkylsulphonyl, amino, C 1-3 alkanoylamino or di-C 1-3 alkylamine group, and pharmacologically acceptable acid addition salts thereof are prepared by heating in an organic solvent a 4-(o-benzoylphenyl)-4H-1,2,4-triazole or 4 - (o - benzylphenyl) - 4H - 1,2,4 - triazole of the respective general formulae with formaldehyde, paraformaldehyde and water or formalin and either hydrochloric acid and an amine of the general formula R<SP>11</SP> R<SP>111</SP>NH or the hydrochloride of the said amine, followed optionally by salification of the product. The 3 - aminomethyl - 4 - (o - benzoylphenyl)- 4H-1,2,4-triazoles may also be obtained by oxidizing the 3 - aminomethyl - 4 - (o - benzylphenyl) - 4H - 1,2,4 - triazoles with Jones' reagent. 4 - (o - Benzoylphenyl) - 4H - 1,2,4 - triazoles of the third general formula above are prepared (a) by treatment of the corresponding triazole-3- carboxaldehyde methanol solvate with silver oxide in aqueous methanol and (b) by treatment of an appropriate 2-chloro-4-phenyl-quinoline with hydrazine hydrate, reaction of the resulting 2 - hydrazino - 4 - phenylquinoline with an appropriate triethyl ortho-carboxylate and oxidation of the resulting 5-phenyl-s-triazolo- [4,3-a]-quinoline at a low temperature with sodium periodate and ruthenium dioxide. 2<SP>1</SP>-Benzoyl-4<SP>1</SP>-chloroacetanilide is prepared by reaction of 2-amino-5-chlorobenzophenone with acetyl chloride. Pharmaceutical compositions having sedative, tranquillizing, hypnotic, muscle-relaxant and anticonvulsant activity comprise, as active ingredient, a 3-aminomethyl-4-(o-benzylphenyl)- 4H-1,2,4-triazole of the second general formula above or a pharmacologically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier.
GB3358972A 1971-08-18 1972-07-18 Triazole derivatives and the manufacture thereof Expired GB1383220A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US17292071A 1971-08-18 1971-08-18

Publications (1)

Publication Number Publication Date
GB1383220A true GB1383220A (en) 1975-02-05

Family

ID=22629749

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3358972A Expired GB1383220A (en) 1971-08-18 1972-07-18 Triazole derivatives and the manufacture thereof

Country Status (7)

Country Link
JP (1) JPS5635668B2 (en)
BE (1) BE787732A (en)
CH (1) CH572475A5 (en)
DE (1) DE2240043A1 (en)
FR (1) FR2150789B1 (en)
GB (1) GB1383220A (en)
NL (2) NL167161C (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5439468A (en) * 1977-09-02 1979-03-26 Shiyouzou Satake Method of molding foamed polystyrene mold case which enables to improve destruction strength
JPH03129992U (en) * 1990-04-12 1991-12-26

Also Published As

Publication number Publication date
JPS4829775A (en) 1973-04-19
DE2240043A1 (en) 1973-03-01
NL8005732A (en) 1981-01-30
FR2150789A1 (en) 1973-04-13
FR2150789B1 (en) 1976-04-16
NL167161B (en) 1981-06-16
JPS5635668B2 (en) 1981-08-19
CH572475A5 (en) 1976-02-13
BE787732A (en) 1973-02-19
NL7211152A (en) 1973-02-20
NL167161C (en) 1981-11-16

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Legal Events

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