公开(公告)号：DE2525024A1

公开(公告)日：1976-12-30

申请号：DE2525024

申请日：1975-06-05

Applicant: BASF AG

Inventor： REIS HERMANN DIPL CHEM DR ,  VILHUBER HEINZ GEORG DIPL CHEM ,  SCHULZ LOTHAR ,  LENKE DIETER PROF DR

IPC: C07D231/12 ,  C07D401/12 ,  C07D403/12

Abstract: Pyrazole derivs. of formula (I) and their acceptable salts are new: (R1 = 6-membered aromatic heterocyclyl with 1 or 2 N atoms opt. substd. by 1-3 halo and/or one 1-4 C alkyl). Prepn. comprises reacting corresp. 4-aminophenyl cpd. with X. CO. R1 (X = OH, halo or alkoxy) under usual conditions, then opt. converting to a salt. (I) have antiphlogistic activity and very low toxicity. The ED33 for inhibition of carragheenin (0.1 ml; 10 mg/ml) induced oedema in the rat paw is 10.9 mg/kg for 1-phenyl-5-(4-nicotinoylaminophenyl)pyrazole (Ia) c.f. 9.5 mg/kg for phenylbutazone. However, phenylbutazone has LD50 (p.o., mouse) 815 mg/kg, whereas (Ia) caused no deaths at 4640 mg/kg. The specifically claimed (Ia) was prepd. in 76% yield by reacting nicotinoyl chloride with 1-phenyl-5-(4-aminophenyl)pyrazole in presence of Et3N in toluene.