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YU45654B - PROCESS FOR PREPARATION OF DIHYDROaryloxyalkylamino-1,2,4-TRIAZOLE DERIVATIVES - Google Patents

PROCESS FOR PREPARATION OF DIHYDROaryloxyalkylamino-1,2,4-TRIAZOLE DERIVATIVES

Info

Publication number
YU45654B
YU45654B YU154784A YU154784A YU45654B YU 45654 B YU45654 B YU 45654B YU 154784 A YU154784 A YU 154784A YU 154784 A YU154784 A YU 154784A YU 45654 B YU45654 B YU 45654B
Authority
YU
Yugoslavia
Prior art keywords
general formula
given above
temperature
meanings given
benzene
Prior art date
Application number
YU154784A
Other languages
Serbo-Croatian (sh)
Other versions
YU154784A (en
Inventor
J. Reiter
P. Krajcsi
Original Assignee
Egyt Gyogyszervegyeszeti Gyar
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 Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar
Publication of YU154784A publication Critical patent/YU154784A/en
Publication of YU45654B publication Critical patent/YU45654B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • C07D249/14—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

POSTUPAK ZA DOBIVANJE DERIVATA DIHIDROARILOKSIALKILAMINO-1,2,4-TRIAZOLA, prema opštoj formuli I: u kojoj R1 i R2 zajedno sa atomom azota grade piperidinski ili pirolidinski prsten, ili njihovih farmaceutski podesnih adicionih soli kiselina, koji obuhvata redukciju ariloksialkilamina sa natrijumom u tečnom amonijaku u prisustvu alkohola, naznačen time, što se ariloksiamin prema opštoj formuli II: u kojoj R1 i R2 imaju gore navedena značenja, redukuje sa ekvivalentnim količinama metalnog natrijuma, u tečnom amonijaku, pri temperaturi od -85 C do -33 C, pri tom se dobijeni dihidroariloksialkilamin prema opštoj formuli III: u kojoj R1 i R2 imaju gore navedena značenja, oslobodi od inaktivnog izomera destilovanjem i potom tretira sa dimetil estrom N-cijanoiminoditiokarbaminske kiseline pri temperaturi od 20 do 120 C u rastvaraču kao što je izopropil alkohol, di-n-propil etar, hloroform, benzol, acetonitril, dimetilformamid, pri tom se dobijeno jedinjenje prema opštoj formuli IV: u kojoj R1 i R2 imaju gore navedena značenja, kristalizacijom oslobadja ostataka neaktivnog izomera i tretira se sa 1 do 1,5-strukim viškom metilhidrazina u prisustvu rastvarača, kao što su n-butanol, di-n-propiletar i benzol, pri temperaturi od 20 do 117 C i pri tome se dobijeno krajnje jedinjenje I u datom slučaju tretiranjem sa odgovarajućom kiselinom prevodi adicionu so kiseline.A process for the preparation of dihydroaryloxyalkylamino-1,2,4-triazole derivatives according to general formula I: in which R 1 and R 2 together with the nitrogen atom form a piperidine or pyrrolidine ring, or their pharmaceutically acceptable acid addition salts, which comprises reduction with aryloxyalkyl of ammonia in the presence of an alcohol, characterized in that the aryloxyamine according to the general formula II: in which R1 and R2 have the meanings given above, is reduced with equivalent amounts of metallic sodium, in liquid ammonia, at a temperature of -85 C to -33 C, the resulting dihydroaryloxyalkylamine according to general formula III: in which R1 and R2 have the meanings given above, is freed from the inactive isomer by distillation and then treated with N-cyanoiminodithiocarbamic acid dimethyl ester at a temperature of 20 to 120 C in a solvent such as isopropyl alcohol, di- n-propyl ether, chloroform, benzene, acetonitrile, dimethylformamide, the compound of general formula IV being obtained: in which R1 and R2 have the meanings given above, by crystallizing the release of residues of the inactive isomer and treating with 1 to 1.5 times the excess methylhydrazine in the presence of solvents such as n-butanol, di-n-propyl ether and benzene, at a temperature of from 20 to 117 C and the resulting final compound I is optionally converted to the acid addition salt by treatment with an appropriate acid.

YU154784A 1983-09-09 1984-09-07 PROCESS FOR PREPARATION OF DIHYDROaryloxyalkylamino-1,2,4-TRIAZOLE DERIVATIVES YU45654B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU833145A HU191095B (en) 1983-09-09 1983-09-09 Process for the production of 3,5 diamino-1,2,4-triazole-derivatives

Publications (2)

Publication Number Publication Date
YU154784A YU154784A (en) 1986-12-31
YU45654B true YU45654B (en) 1992-07-20

Family

ID=10962781

Family Applications (1)

Application Number Title Priority Date Filing Date
YU154784A YU45654B (en) 1983-09-09 1984-09-07 PROCESS FOR PREPARATION OF DIHYDROaryloxyalkylamino-1,2,4-TRIAZOLE DERIVATIVES

Country Status (13)

Country Link
JP (1) JPS60100543A (en)
AT (1) AT389109B (en)
CS (1) CS244830B2 (en)
DD (1) DD219767A5 (en)
DE (1) DE3433143A1 (en)
ES (1) ES8600258A1 (en)
FI (1) FI80685C (en)
FR (1) FR2551752B1 (en)
GB (1) GB2146331B (en)
HU (1) HU191095B (en)
IT (1) IT1180224B (en)
SU (1) SU1480767A3 (en)
YU (1) YU45654B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19848649C5 (en) 1998-10-22 2008-11-27 Peter Greiner Carbon piston for an internal combustion engine
EP4196793A1 (en) 2020-08-11 2023-06-21 Université de Strasbourg H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3067564D1 (en) * 1979-10-22 1984-05-24 Glaxo Group Ltd 1,2,4-triazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing them
DK558181A (en) * 1981-01-30 1982-07-31 Smithkline Corp METHOD OF PREPARING 3,5-DIAMINO-1,2,4-TRIAZOLES

Also Published As

Publication number Publication date
FR2551752B1 (en) 1987-04-24
ES535998A0 (en) 1985-10-16
IT8422568A0 (en) 1984-09-07
ES8600258A1 (en) 1985-10-16
HUT34963A (en) 1985-05-28
FI80685B (en) 1990-03-30
JPS60100543A (en) 1985-06-04
GB2146331B (en) 1987-05-13
YU154784A (en) 1986-12-31
FI843527A0 (en) 1984-09-07
CS244830B2 (en) 1986-08-14
DD219767A5 (en) 1985-03-13
FI843527L (en) 1985-03-10
FI80685C (en) 1990-07-10
GB8422620D0 (en) 1984-10-10
ATA287084A (en) 1989-03-15
DE3433143A1 (en) 1985-03-28
AT389109B (en) 1989-10-25
FR2551752A1 (en) 1985-03-15
IT1180224B (en) 1987-09-23
HU191095B (en) 1987-01-28
SU1480767A3 (en) 1989-05-15
GB2146331A (en) 1985-04-17

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