AU574075B2 - Trisazolo(2,3-c)(1,3)benzodiazepines - Google Patents

Trisazolo(2,3-c)(1,3)benzodiazepines

Info

Publication number
AU574075B2
AU574075B2 AU29106/84A AU2910684A AU574075B2 AU 574075 B2 AU574075 B2 AU 574075B2 AU 29106/84 A AU29106/84 A AU 29106/84A AU 2910684 A AU2910684 A AU 2910684A AU 574075 B2 AU574075 B2 AU 574075B2
Authority
AU
Australia
Prior art keywords
alkyl
carbamoyl
alkoxy
sulfamoyl
hydroxy
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.)
Ceased
Application number
AU29106/84A
Other versions
AU2910684A (en
Inventor
Isidoros Vlattas
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.)
Novartis AG
Original Assignee
Ciba Geigy 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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of AU2910684A publication Critical patent/AU2910684A/en
Application granted granted Critical
Publication of AU574075B2 publication Critical patent/AU574075B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • 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
    • 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
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • C07D487/02—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 two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Psychiatry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

1. Claims for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE Compounds of the formula see diagramm : EP0129509,P18,F1 wherein R1 is hydrogen, C1 -C4 alkylthio, amino, (C1 -C4 alkanoyl-, C1 -C4 alkoxycarbonyl-, carbamoyl-, sulfamoyl-, C1 -C4 monoalkyl-, or di-C1 -C4 alkyl-carbamoyl- or -sulfamoyl-, halosulfonyl-, phenyl-C1 -C2 alkoxy-carbonyl-, C1 -C4 alkyl- or di-C1 -C4 alkyl-)amino, C1 -C4 alkoxy, (C1 -C4 alkanoyl-, C1 -C4 alkoxycarbonyl-, carbamoyl-, sulfamoyl-, mono-C1 -C4 alkyl- or di-C1 -C4 alkyl-carbamoyl- or -sulfamoyl-, halosulfonyl- or phenyl-C1 -C2 alkoxycarbonyl-) oxy, C1 -C4 alkyl, acetyl, propionyl, hydroxy, halogen, trifluoromethyl, cyano, carboxy, methoxy- or ethoxy-carbonyl, carbamoyl, mono- or di-methyl- or -ethyl-carbamoyl, hydroxy-C1 -C4 alkyl or di-C1 -C4 alkylamino-C1 -C4 alkyl ; Cn H2n is C2 -C4 alkylene separating the two nitrogen atoms by 2 or 3 carbon atoms ; R2 is hydrogen, C1 -C7 alkyl, allyl, propargyl, acetyl, propionyl, phenyl-C1 -C3 alkyl which can be substituted at the phenyl ring by halogen, C1 -C4 alkoxy or by C1 -C4 alkyl, methoxy- or ethoxy-carbonyl, phenylmethoxycarbonyl, phenylethoxycarbonyl, 2-hydroxy-(ethyl or propyl), 3-hydroxy-(propyl or butyl), 4-hydroxybutyl, C2 -C4 alkanoyl-oxy-C2 -C4 alkyl, phenoxy-C2 -C4 alkyl which can be substituted at the phenyl ring by halogen, C1 -C4 alkoxy or by C1 -C4 alkyl, or C1 -C4 alkoxy-C2 -C4 alkyl ; R3 and R4 independently represent hydrogen, C1 -C7 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, halogen, trifluoromethyl, hydroxy, acetoxy, propionyloxy, sulfamoyl, mono- or di-C1 -C4 alkylsulfamoyl, and R5 and R6 represent hydrogen or C1 -C4 alkyl ; and N-oxides and salts thereof. 1. Claims for the Contracting State : AT A process for the manufacture of compounds of the formula see diagramm : EP0129509,P20,F2 wherein R1 is hydrogen, C1 -C4 alkylthio, amino, (C1 -C4 alkanoyl-, C1 -C4 alkoxycarbonyl-, carbamoyl-, sulfamoyl-, C1 -C4 monoalkyl-, or di-C1 -C4 alkyl-carbamoyl- or -sulfamoyl-, halosulfonyl-, phenyl-C1 -C2 alkoxy-carbonyl-, C1 -C4 alkyl- or di-C1 -C4 alkyl-)amino, C1 -C4 alkoxy, (C1 -C4 alkanoyl-, C1 -C4 alkoxycarbonyl-, carbamoyl-, sulfamoyl-, mono-C1 -C4 alkyl- or di- C1 -C4 alkyl-carbamoyl-or -sulfamoyl-, halosulfonyl- or phenyl-C1 -C2 alkoxycarbonyl-)oxy, acyloxy, C1 -C4 alkyl, acetyl, propionyl, hydroxy, halogen, trifluoromethyl, cyano, carboxy, methoxy- or ethoxy-carbonyl, carbamoyl, mono- or di-methyl- or -ethyl-carbamoyl, hydroxy- C1 -C4 alkyl or di-C1 -C4 alkylamino-C1 -C4 alkyl ; Cn H2n is C2 -C4 alkylene separating the two nitrogen atoms by 2 or 3 carbon atoms ; R2 is hydrogen, C1 -C7 alkyl, allyl, propargyl, acetyl, propionyl, phenyl-C1 -C3 alkyl which can be substituted at the phenyl ring by halogen, C1 -C4 alkoxy or by C1 -C4 alkyl, methoxy- or ethoxy-carbonyl, phenylmethoxycarbonyl, phenylethoxycarbonyl, 2-hydroxy-(ethyl or propyl), 3-hydroxy-(propyl or butyl), 4-hydroxybutyl, C2 -C4 alkanoyloxy-C2 -C4 alkyl, phenoxy-C2 -C4 alkyl which can be substituted at the phenyl ring by halogen, C1 -C4 alkoxy or by C1 -C4 alkyl, or C1 -C4 alkoxy-C2 -C4 alkyl ; R3 and R4 independently represent hydrogen, C1 -C7 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, halogen, trifluoromethyl, hydroxy, acetoxy, propionyloxy, sulfamoyl, mono- or di- C1 -C4 alkylsulfamoyl, and R5 and R6 represent hydrogen or C1 -C4 alkyl ; and N-oxides and salts thereof, characterized in that a) a compound of the formula III see diagramm : EP0129509,P20,F3 wherein X is a group detachable together with hydrogen or with an alkali metal, and the other symbols are as defined under the formula I, is condensed with a compound of formula IV see diagramm : EP0129509,P21,F1 or with an alkali metal derivative thereof in which R2 is as defined under the formula I, or b) a compound of the formula VI see diagramm : EP0129509,P21,F2 wherein Z is oxygen, sulfur or NH, and the other symbols are as defined above, is cyclized under dehydrating, dehydrosulfurating or deaminating conditions, and, if desired, a resulting free compound is converted into a salt or a resulting salt is converted into the free compound or into another salt, and/or, if desired, a resulting mixture of isomers or racemates is resolved into the single isomers or racemates, and/or, if desired, resulting racemates are resolved into the optical antipodes.
AU29106/84A 1983-06-06 1984-06-05 Trisazolo(2,3-c)(1,3)benzodiazepines Ceased AU574075B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US50132883A 1983-06-06 1983-06-06
US501328 1983-06-06

Publications (2)

Publication Number Publication Date
AU2910684A AU2910684A (en) 1984-12-13
AU574075B2 true AU574075B2 (en) 1988-06-30

Family

ID=23993078

Family Applications (1)

Application Number Title Priority Date Filing Date
AU29106/84A Ceased AU574075B2 (en) 1983-06-06 1984-06-05 Trisazolo(2,3-c)(1,3)benzodiazepines

Country Status (17)

Country Link
EP (1) EP0129509B1 (en)
JP (1) JPS606689A (en)
AT (1) ATE45740T1 (en)
AU (1) AU574075B2 (en)
CA (1) CA1215044A (en)
DD (1) DD220310A5 (en)
DE (1) DE3479499D1 (en)
DK (1) DK276484A (en)
ES (1) ES8506713A1 (en)
FI (1) FI78098C (en)
GR (1) GR82058B (en)
HU (1) HU190930B (en)
IL (1) IL72015A (en)
NO (1) NO162070C (en)
NZ (1) NZ208373A (en)
PT (1) PT78687A (en)
ZA (1) ZA844186B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL84093A (en) * 1986-10-09 1992-09-06 Ciba Geigy Ag Aralkyl-4h-1,2,4-triazole derivatives,their preparation and pharmaceutical compositions containing them
DE19824673A1 (en) * 1998-05-26 1999-12-02 Schering Ag New 2,3-benzodiazepine derivatives are AMPA receptor inhibitors useful in treatment of neurological and psychiatric disorders

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3539573A (en) * 1967-03-22 1970-11-10 Jean Schmutz 11-basic substituted dibenzodiazepines and dibenzothiazepines
US4192803A (en) * 1978-09-15 1980-03-11 American Cyanamid Company 5H-Pyrrolo[2,1-c][1,4]benzodiazepine derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4076823A (en) * 1977-08-18 1978-02-28 E. R. Squibb & Sons, Inc. Triazolo-2,4-benzodiazepines
FI824170L (en) * 1981-12-07 1983-06-08 Ciba Geigy Ag IMMEDAZOBENSODIAZEPINER, FOERFARANDE FOER DERAS FRAMSTAELLNING, DESSA FOERENINGAR INNEHAOLLANDE PHARMACEUTICAL PREPARATION OCH DERAS ANVAENDNING

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3539573A (en) * 1967-03-22 1970-11-10 Jean Schmutz 11-basic substituted dibenzodiazepines and dibenzothiazepines
US4192803A (en) * 1978-09-15 1980-03-11 American Cyanamid Company 5H-Pyrrolo[2,1-c][1,4]benzodiazepine derivatives

Also Published As

Publication number Publication date
ATE45740T1 (en) 1989-09-15
IL72015A0 (en) 1984-10-31
NO162070C (en) 1989-11-01
DK276484A (en) 1984-12-07
ES533135A0 (en) 1985-08-01
GR82058B (en) 1984-12-13
DD220310A5 (en) 1985-03-27
EP0129509A3 (en) 1985-09-11
NZ208373A (en) 1987-02-20
DE3479499D1 (en) 1989-09-28
DK276484D0 (en) 1984-06-04
FI842228A0 (en) 1984-06-04
HUT34488A (en) 1985-03-28
NO842254L (en) 1984-12-07
IL72015A (en) 1987-12-31
ES8506713A1 (en) 1985-08-01
FI78098B (en) 1989-02-28
ZA844186B (en) 1985-02-27
PT78687A (en) 1984-07-01
FI78098C (en) 1989-06-12
HU190930B (en) 1986-12-28
AU2910684A (en) 1984-12-13
JPH0354669B2 (en) 1991-08-20
FI842228A (en) 1984-12-07
CA1215044A (en) 1986-12-09
EP0129509B1 (en) 1989-08-23
NO162070B (en) 1989-07-24
JPS606689A (en) 1985-01-14
EP0129509A2 (en) 1984-12-27

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