IL29944A - 3-pyrazolidinone derivatives and processes for their preparation - Google Patents

Description

derivatives and processes their preparation The present invention relates de their pr n a process fo general fo in or di or wherein an ted acid of general II COOH or a lower alkyl ester thereof is reacted with a hydrazine derivative of general formula III The according to the invention preferably performed by at the temperature of an if or in and evaporating the to An inert in connection with the present invention an organic solvent which inert towards the the final A The iixture of of and can be conveniently by use of an e wherein the of general which tendency are retained on thq and nds of general formula which have starting the compounds of formulae I Another for the of derivatives of general and the preparation of to a general formula IVa or IVa XVb in which and have the meaning as above and to said in an solvent or in the preeenoe of an The of general IVa and or be re ared as described a of general pyraaolidi pf genernl N in which end have above to a reac a formula which above and stands halogen preferably in an inert in of an It haa been found that of formulae and and of o of also be utilised photographic d rats the hot plate and the clip testa the at of 200 be analgesics comparable to and The therapeutic waa found tp favourable than 3 The derivatives of general formulae and are all new with the exception of those compounds of formula in and Rostand both for and The present invention thus consists also in these new The derivatives of general formulae and lb and their hydrochlorides may be prescribed in the form of tinctures or said compositions being prepared in a conventional by the additional of suitable solvents other suitable therapeutic invention will be illustrated by the following Examples without being limited by All temperatures are indicated herein in degrees All melting points are Method A of the Appropriate acid of general formula II was added gradually cooling to a solution of mole of a hydrazine derivative of general formula in 60 of resulting fluxed for hours and pyridine distilled off in The residue vas dissolved in in if and the solution was filtered and passed through an The coluoin was washed with water and the effluent was to thus obtained was either or The crude base was alternatively into a a hydrochloride by dissolving it in an equal weight of and the with an excess of isopropanolic The resin was with excess of a aqueous acetic acid The eluate was evaporated to dryness to give the zolidinono which as also alternatively converted into the Some o compounds prepared by this method are 1 The analysis was calculated for Calculateds Ct Ns 2 analysis calculated Ci 0s Cs Cls Cs a The analysis was calculated for Cs Ns Founds Ht Ns Founds Cs Hs analysis calculated Cs Ht Cls Pounds Cs Hs Ht Cls Cs Ht The analysis calculated for Calculatedt Nt Ct Nt Clt Nt The analysis vas culated for Hs Nt Founds Ht t Foundί Nt Example 7 The analysis was calculated for Cc Ht Ct Nt Ct Hs analysis s calculated for Nt Clt sup e analysis was calculated for Ci Nt Founds Ci fls Nt Nt Cls Examp 10 The analysis vat calculated Nt Clt Hi Ns Clt Ci Ni Clt β was culated for Cs Hi Ns Ns Example 12 The analysis was calculated for Us Ns Cls Founds Ct Hs Hs Cls hydrochloride Founds Hs Ns Example 13 The analysis was calculated for Cs Hs Ns Founds Cs Hs Ns Founds Cs Hs Ns Cls 14 analysis was calculated for Calculateds Cs Founds Ci Ns 15 The analysis vas culated for Calculateds Ms Founds Ns Founds Hs Method Bole of an appropriate halide of general formula VI vas added gradually vith cooling to a solution of of a compound of general formula V in 10 of resulting mixture vas refluxed for and the pyridine was distilled off at reduced The residue puri by or or by dissolving in va er and passing the solution through a 20 10 After washing the column to it vaa eluted with a ammonia solution and the was evaporated to dryness to give a which converted into th of by this method are given Example 16 The compound was identica with that obtained in The compound was identical with that obtained in 9 Example The compound was identical with that obtained in Example 19 The coapound was identical with that ObMned in C An excess of isopropanolic hydrochloride was to a suspensio of mole of appropriate acid of general formulae o in ml of The resulting mixture w s refluxed for 1 hour and then cooled to precipitated hydrochloride was collected on the washed with some iaopropanol and The compound prepared by this oil 20 compound was identical vith that obtained in Method 0 mole lover ester of an acid of general formula II added gradually vith to mole of a hydrazine derivative of general formula The resulting mixture for reaction mixture vae dissolved in water in if vater the solution vae filtered and passed an column was washed vith vater and effluent w s evaporated to affording tho purified and converted to a salt The resin vas eluted vith an excess of a aqueous acetic acid The eluate vas evaporated to dryness to give the vhich vas also converted to the The following compounds prepared by this 31 The vas vith that obtained in Example The compound vas identical vith that obtained in Example insufficientOCRQuality

Claims (1)

1. Claims - 12 - 299 /3 *

1. Process for the preparation of 3-pyrazolidinone derivatives of general formulae la and lbs ' in which and Rg stand each for hydrogen, or the same or different lower alkyl or phenyl and B