GB1074578A - Alicyclic diamines - Google Patents

Abstract

1,074,578. Alicyclic diamines. AYERST, McKENNA & HARRISON Ltd. Dec. 20, 1963 [Dec. 21, 1962(2); Feb. 5, 1963; Feb. 12, 1963; June 4, 1963; July 30, 1963; Aug. 2, 1963 (3); Dec. 6, 1963], No 50497/63. Heading C2C. New compounds of formula where Q is one of the radicals of formulµ and when K is methylene and Q has Formula II then R is one of radicals (VIII) to (XVII) with the proviso that alkyl radicals (X) have at least three carbon atoms; and when K is a valency bond and Q has Formula II then R is one of radicals (VI) to (IX) and (XII); and when K is a methylene group and Q is represented by III, IV or V then R is one of radicals (VI) to (XVII): benzyl (VI), halo or trihalomethyl substituted benzyl (VII), trihalomethyl substituted benzyl (VIII), indanyl (IX), alkyl (X), cycloalkyl (XI), cycloalkylalkyl (XII), alkenyl (XIII), cycloalkenylalkyl (XIV), bicycloalkyl (XV), bicycloalkenylalkyl (XVI) and bicycloalkylalkyl (XVII), the radicals (IX), (XI), (XII) and (XIV) to (XVII) optionally carrying substituents selected from halogen, alkyl, and hydroxy on the ring; and pharmaceutically acceptable acid addition salts, and isomers (geometrical and optical), are prepared by the following processes: (a) for compounds I where Q is II, K is CH2 and R is (VIII) to (XVII), by reacting H2NCH2- II-CH2NH2 with R<1>- CO-R<2>, where R<1> is hydrogen or halogen and R<2> is appropriate to the desired product or R<1>-CO-R<2> is an indanone, cycloalkanone or bioycloalkanone, and reducing the amide or Schiff base; (b) for compounds I where Q is II, K is a valency bond and R is (VI), (VII), (IX) or (XII), by reacting H2N-II-NH2 with R<1>-CO-R<3>, where R<3> is appropriate to the product or R<1>-CO-R<3> is an indanone, and reducing the intermediate formed; (c) for compounds I where Q is III, IV, or V, K is CH2 and R is (VI) to (XVII), by reacting H2NCH2-QCH2NH2 with R<1>-CO-R<4> where R<4> is appropriate to the product or R<1>-CO-R<4> is an indanone, cycloalkanone is bicycloalkanone, and reducing the intermediate; (d) for compounds I where Q is II, K is a valency bond and R is (VI), (VII), (IX) or (XII), by reacting cyclohexane-1,4-dione with R<5>-NH2, where R<5> is as appropriate, and reducing the intermediate; (e) for compounds I where Q is II to V, K is CH2 and R is as defined, by reacting Hal-CO-Q-CO-Hal, Hal being halogen, with R<6>-NH2, R<6> being as appropriate, and reducing the intermediate. Intermediates which are amides or Schiff's bases are prepared in the course of processes (a)-(e). Additional starting materials prepared are: 1 - cyclohexene - 1,4 - dicarbonyl chloride, the 1,4-dicarboxamide and the 1,4- bis-(aminomethyl) compounds; 1,4-bis-(amino methyl) - bicyclo[2,2,2]octane; traps-1,4-eyclohexanedicarbonyl chloride. Pharmaceutical compositions comprise new compounds I, and their salts, with carriers, oral, topical and parenteral preparations which affect lipid and cholesterol metabolism and are antimicrobial being mentioned.