IE34268B1 - Hydrazines and hydrazones of pyrazolopyridine carboxylic acids and esters - Google Patents

Abstract

1317797 Pyrazolo-pyridines E R SQUIBB & SONS Inc 10 June 1970 [16 June 1969] 28164/70 Heading C2C Novel compounds of Formulµ I and II: (in which R 1 is H, alkyl or phenyl-C 1-7 alkyl, R 2 is C 1-7 alkyl, phenyl, phenyl-C 1-7 alkyl, R 6 and/or R 7 -substituted phenyl-C 1-7 alkyl or cycloalkyl-C 1-7 alkyl, R 3 is H, C 1-7 alkyl, phenyl or R 6 and/or R 7 -substituted phenyl, R 4 is H, C 1-7 alkyl, C 1-7 alkanoyl or phenyl, R 5 is H, alkyl or C 1-7 alkanoyl, each of R 6 and R 7 is halogen, C 1-7 alkyl or C 1-7 alkoxy, X is H, C 1-7 alkyl, C 1-7 hydroxyalkyl, phenyl, R 6 - and/or R 7 - substituted phenyl, phenyl-C 1-7 alkyl or R 6 and/or R 7 -substituted phenyl-C 1-7 alkyl, Y is C 1-7 alkyl, C 1-7 hydroxyalkyl, phenyl, R 6 and/or R 7 -substituted phenyl, phenyl-C 1-7 alkyl or R 6 and/or R 7 -substituted phenyl-C 1-7 alkyl or X and Y together with the adjacent carbon atom represent cycloalkylidene or 5-nitro-2- furylidene) and acid addition salts thereof, are prepared by reacting a compound of Formula III: (in which R<SP>1</SP> is Cl, OH, C 1-7 alkoxy or phenyl- C 1-7 alkoxy) with a hydrazine of formula H 2 N.NR 4 R 5 , or a salt thereof, to form a product of Formula I, and, if desired, when R 4 and R 5 in the product are both H, reacting the product with a carbonyl compound of formula XYC = O to form a product of Formula II, and optionally converting either of said products to an acid addition salt thereof. Compounds I in which R 4 is H and R 5 is C 2-7 alkyl may also be prepared by reduction of appropriately substituted compounds II. Compounds of Formula III are prepared by reacting a compound of Formula IV: with a compound of Formula V: (in which R 1 is C 1-7 alkyl or phenyl-C 1-7 alkyl) to give a compound of Formula VI: cyclizing this to give a compound III in which R<SP>1</SP> is OH and R 1 is C 1-7 alkyl or phenyl-C 1-7 alkyl, and, if desired, hydrolysing the ester group to the free acid group and/or converting the OH group to a chlorine atom or an alkoxy group. Pharmaceutical and disinfectant compositions comprise one of the above novel compounds together with a carrier. The pharmaceutical compositions may be used as antibacterial agents, as tranquillizers and in the relief of asthma, and may be in a form suitable for oral, topical or parenteral administration. The compositions may be in the form of a soap or detergent. [GB1317797A]