NEUE BIGUANID-DERIVATE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE ANWENDUNGSMOEGLICHKEITEN

• Main Author: ARON-SAMUEL, JAN MARCEL DIDIER.MED., SURESNES, HAUTS DE SEINE (FRANKREICH)
• Format: Patent
• Language: German
• Published: 01.03.1973
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

1351025 Oxadiazol - 5 - yl - biguanides J M D ARON-SAMUEL 18 Aug 1972 [20 Aug 1971] 39234/71 Heading C2C Novel compounds (I) their quaternary ammonium derivatives and acid addition salts in which R 1 , R 2 , R 3 , R 4 , R 5 are selected from hydrogen, halo, alkyl, alkoxy, monohalo or polyhalo-alkyl or two adjacent groups may form an alkylene-dioxy bridge and R is (a) NR 6 R 7 in which R 6 , R 7 are hydrogen, alkyl, allyl or a heterooyclic group optionally substituted by an alkyl group or together with the N atom form a 5- or 6-membered heterocycle which may contain another heteroatom and may be substituted by at least one group selected from alkyl, hydroxy, alkoxy phenyl, alkylphenyl and haloalkylphenyl or (b) n which R 8 is hydrogen or alkyl, A is straight or branched chain alkylene and R 9 and R 10 are alkyl or together with the N atom form a 5-7 membered heterocycle which may be substituted by at least one alkyl group and may contain another heteroatom, are prepared by reaction of a biguanide (II) with an oxadiazole derivative in which X is halogen or tri-halomethyl. Preferred compounds include 1 - (3 - dibutylaminopropyl) - 5 - (3 - phenyl - 5 - oxadiazolyl)- biguanide, 1 - morpholino - 5 - (3 - phenyl - 5- oxadiazolyl) - biguanide, 1 - (5 - diethylamino- 2 - pentyl) - 5 - (3 - phenyl - 5 - oxadiazolyl)- biguanide, 1 - (3 - dibutylaminopropyl)- 5 - (3- m - chlorophenyl - 5 - oxadiazolyl) - biguanide and 1 - [(4 - hydroxy - 4 - p - chlorophenyl)- piperidino] - 5 - (3 - phenyl - 5 - oxadiazolyl)- biguanide. Compounds (I) have anti-spasmodic properties, analgesic, anti-inflammatory and antimalarial action and form with a carrier a pharmaceutical preparation which may be administered orally, parenterally or rectally.