N-alkyl-1,4-dihydropyridines and their production

Abstract

Abstract N-ALKYL-1,4-DIHYDROPYRIDINES OF THE FORMULA: 1-R,2,6-DI(R''-),3,5-DI(R"-OOC-),4-X-1,4-DIHYDROPYRIDINE WHEREIN ARE PRODUCED BY REACTING AN ALDEHYDE OF THE FORMULA: X-CHO WHEREIN X IS AN ABOVE DEFINED WITH A B-KETOCARBOXYLIC ACID ESTER OF THE FORMULA: R''-CO-CH2-COOR" WHEREIN R'' AND R" ARE AS ABOVE DEFINED WITH A SALT OF AN ALKYLAMINE OF THE FORMULA: R-NH2 WHEREIN R IS ABOVE DEFINED, IN THE PRESENCE OF AN ACID ACCEPTOR. HOWEVER WHEN ONE OF THE REACTANTS ALREADY HAS ACID-BINDING PROPERTIES, THE ACID ACCEPTOR IS NOT ESSENTIAL. THESE N-ALKYL-1,4-DIHYDROPYRIDINES ARE USEFUL FOR THEIR CORONARY DIALATING EFFECT AND ARE ALSO USEFUL AS BLOOD PRESSURE DEPRESSING AGENTS. R IS A SATURATED OR UNSATURATED STRAIGHT OR BRANCHED CHAIN ALIPHATIC MOIETY, A STATURATED OR UNSATURATED CYCLO ALIPHATIC MOIETY, SAID CYCLOALIPHATIC MOIETY HAVING AN N, S OR O HETEROATOM, SAID CYCLOALIPHATIC MOIETY OR SAID CYCLALIPHATIC MOIETY HAVING AN N, S, OR O HETEROATOM SUBSTITUTED BY CARBOXY, CARBALKOXY, ALKOXY, ESPECIALLY LOWER ALKOXY, ALKYLMERCAPTO, ESPECIALLY LOWER ALKYLMERCAPTO, ALKYLAMINO, ESPECIALLY LOWER ALKYLAMINO, OR DIALKYLAMINO, ESPECIALLY DI-LOWER ALKYLAMINO, AN ARALIPHATIC MOIETY OR AN ARALIPHATIC MOIETY SUBSTITUTED BY ALKYL, ESPECIALLY LOWER ALKYL, ALKOXY, ESPECIALLY LOWER ALKOXY, NITRO OR HALOGEN, R'' IS HYDROGEN OR STRAIGHT OR BRANCHED CHAIN ALKYL OF 1 TO 4 CARBON ATOMS, ARYL, ARYL SUBSTITUTED BY ALKYL, ESPECIALLY LOWER ALKYL, NITRO OR HALOGEN, OR A HETEROCYCLE, R" IS A SATURATED OR UNSATURATED, STRAIGHT OR BRANCHED CHAIN ALIPHATIC MOIETY OF 1 TO 6 CARBON ATOMS, A SATURATED OR UNSATURATED CYCLOALIPHATIC MOIETY OR SAID CYCLOALIPHATIC MOIETY HAVING AN N, S OR O HETEROATOM, AND X IS SATURATED OR UNSATURATED, STRAIGHT OR BRANCHED CHAIN ALIPHATIC OR ISOCYCLIC MOIETY, A HETEROCYCLE, ARYL, ARYL SUBSTITUTED BY ALKYL, ESPECIALLY LOWER ALKYL, ALKOXY, ESPECIALLY LOER ALKOXY, CARBALKOXY, ESPECIALLY CARBLOWER ALKOXY, ALKYMERCAPTO, ESPECIALLY LOWER ALKYLMERCAPTO, TRIFLUOROMETHYL, NITRILE, NITRO OR HALOGEN, ARALKYL, ARALKYLENE OR ARALKYL OR ARALKYLENE SUBSTITUTED BY ALKYL, ESPECIALLY LOWER ALKYL, ALKOXY, ESPECIALLY LOWER ALKOXY, CARBALKOXY, ESPECIALLY CARB-LOWER ALKOXY, ALKYLMERCAPTO, ESPECIALLY LOWER ALKYMERCAPTO, TRIFLUOROMETHYL, NITRILE, NITRO OR HALOGEN,

Inventors

• 👤 F Bossert

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