Substituted 1-phenyl-3-pyrazolecarboxamides active on neurotensin receptors, their preparation and pharmaceutical compositions containing them

Compound of formula:

• ##STR123## in which:
• --R.sub.1 represents a group chosen from:
• --T--CN;
• --C(NH.sub.2).dbd.NOH;
• --C(.dbd.NOH)NH(CH.sub.2).sub.r NR.sub.5 R.sub.6 ;
• --T--C(NR.sub.12 R.sub.13).dbd.NR.sub.14 ;
• --C(NH.sub.2).dbd.NO(CH.sub.2).sub.r NR.sub.5 R.sub.6 ;
• --T--CONR.sub.a R.sub.b ;
• --T--CONR.sub.7 R.sub.c ;
• --Y--CO.sub.2 R.sub.7 ;
• --OR.sub.d ;
• --T--NR.sub.5 R.sub.6, on condition that R.sub.5 and R.sub.6 do not simultaneously represent hydrogen when T represents a direct bond;
• --T--N(R.sub.7)COR.sub.e ;
• --SO.sub.2 NR.sub.a R.sub.b ;
• --T--N(R.sub.7)SO.sub.2 R'.sub.7 ;
• --T--NR.sub.27 R.sub.28 ;
• --NR.sub.a R.sub.b represents a group chosen from:
• --NR.sub.5 R.sub.6 ;
• --NR.sub.9 (CH.sub.2).sub.s CR.sub.7 R.sub.8 (CH.sub.2).sub.t NR.sub.5 R.sub.6 ;
• --NR.sub.21 (CH.sub.2).sub.s CR.sub.7 R.sub.8 (CH.sub.2).sub.t R.sub.22 R.sub.23 R.sub.24 Q.sup..crclbar.
• --NR.sub.7 (CH.sub.2).sub.q CN;
• --NR.sub.7 (CH.sub.2).sub.q C(NR.sub.12 R.sub.13).dbd.NR.sub.14 ;
• --NR.sub.7 (CH.sub.2).sub.q CONH.sub.2 :--NR.sub.7 (CH.sub.2).sub.q CO.sub.2 R.sub.7 ;
• --NR.sub.21 (CH.sub.2).sub.s CR.sub.7 R.sub.8 (CH.sub.2).sub.t NR.sub.25 R.sub.26 ;
• --R.sub.c represents a group chosen from:
• --X--OR.sub.7 ;
• --CHR.sub.20 CO.sub.2 R.sub.7 ;
• --(CH.sub.2).sub.4 CH(NH.sub.2)CO.sub.2 R.sub.7 ;
• --R.sub.d represents a group chosen from:
• --X--NR.sub.5 R.sub.6 ;
• --Y--CONR.sub.5 R.sub.6 ;
• --Y--CO.sub.2 R.sub.7 ;
• --Y--SO.sub.2 NR.sub.5 R.sub.6 ;
• --R.sub.e represents a group chosen from:
• --R.sub.16 ;
• --Y--NR.sub.5 R.sub.6, --Y--NHCOR.sub.16 ;
• --CH(R.sub.17)NR.sub.5 R.sub.6 ;
• --Y--R.sub.22 R.sub.23 R.sub.24 Q.sup..crclbar. ;
• --(CH.sub.2).sub.q CN;
• --(CH.sub.2).sub.q C(NR.sub.12 R.sub.13).dbd.NR.sub.14 ;
• --NR.sub.18 R.sub.19 ;
• --R.sub.2 and R.sub.3 each independently represent hydrogen, a (C.sub.1 -C.sub.6)alkyl, a (C.sub.3 -C.sub.8)cycloalkylmethyl, a (C.sub.3 -C.sub.8)cycloalkyl, a halogen, a nitro, a trifluoromethyl, a group --OR.sub.4, a group --NR.sub.5 R.sub.6, a cyano, a carbamoyl;
• --or R.sub.2 and R.sub.3 together constitute a trimethylene, tetramethylene or pentamethylene group;
• --R.sub.4 represents hydrogen;
• a (C.sub.1 -C.sub.6)alkyl;
• a (C.sub.3 C.sub.4)alkenyl;
• a (C.sub.3 C.sub.8)cycloalkylene;
• a (C.sub.3 C.sub.8)cycloalkylmethyl;
• a (C.sub.1 -C.sub.4)alkoxy(C.sub.1 -C.sub.4)alkylene;
• a benzyl;
• R.sub.5 and R.sub.6 each independently represent a hydrogen, a (C.sub.1 -C.sub.6)alkyl;
• a (C.sub.3 -C.sub.8)alkenyl;
• a (C.sub.3 -C.sub.8)cycloalkylmethyl;
• --R'.sub.5 and R'.sub.6 each independently represent a hydrogen or a (C.sub.1 -C.sub.6)alkyl;
• --R'.sub.7 represents a (C.sub.1 -C.sub.4)alkyl;
• a phenyl which is unsubstituted or substituted one or more times with a (C.sub.1 -C.sub.4)alkyl;
• a group --X--NR.sub.5 R.sub.6 ;
• --R.sub.7 represents a hydrogen, a (C.sub.1 -C.sub.4)alkyl or a benzyl;
• R.sub.8 represents a hydrogen, a (C.sub.1 -C.sub.4)alkyl, a hydroxyl, or R.sub.7 and R.sub.8, together with the carbon atom to which they are attached, constitute a (C.sub.3 -C.sub.5)cycloalkane;
• --R.sub.9 represents hydrogen, a (C.sub.1 -C.sub.4)alkyl, a benzyl, a group --X--OH or a group --X--NR'.sub.5 R'.sub.6, a (C.sub.3 -C.sub.8)alkenyl;
• --R.sub.12 and R.sub.13 each independently represent a hydrogen or a (C.sub.1 -C.sub.4)alkyl;
• --R.sub.14 represents hydrogen. R.sub.14 may, in addition, represent a (C.sub.1 -C.sub.4)alkyl when R.sub.12 represents hydrogen and R.sub.13 represents a (C.sub.1 -C.sub.4)alkyl;
• --R.sub.16 represents hydrogen, a (C.sub.1 -C.sub.8)alkyl, a (C.sub.3 -C.sub.8)cycloalkyl, a phenyl
• --R.sub.17 represents a (C.sub.1 -C.sub.6)alkyl, a phenyl, a benzyl, a hydroxy(C.sub.1 -C.sub.4)alkyl, an amino(C.sub.1 -C.sub.4)alkyl;
• --R.sub.18 and R.sub.19 each independently represent a hydrogen, a (C.sub.1 -C.sub.4)alkyl;
• R.sub.18 may, in addition, represent a group --(CH.sub.2).sub.q -NR.sub.5 R.sub.6 ;
• --R.sub.20 represents hydrogen, a (C.sub.1 -C.sub.4)alkyl, a benzyl, a hydroxyphenylmethyl, a hydroxy(C.sub.1 -C.sub.4)alkyl, a mercapto(C.sub.1 -C.sub.4)alkyl;
• a --(CH.sub.2).sub.3 -NH--C(.dbd.NH)NH.sub.2 group, a --(CH.sub.2).sub.4 NH.sub.2 g
• --R.sub.21 represents a (C.sub.1 -C.sub.4)alkyl, an allyl or a benzyl;
• --R.sub.22 and R.sub.23 each independently represent a (C.sub.1 -C.sub.6)alkyl;
• --R.sub.24 represents a (C.sub.1 -C.sub.4)alkyl, a benzyl, an allyl, a hydroxy(C.sub.1 -C.sub.4)alkyl, a (C.sub.1 -C.sub.4)alkoxy(C.sub.1 -C.sub.4)alkyl;
• Q.sup..crclbar. represents an anion;
• --R.sub.25 represents hydrogen or a (C.sub.1 -C.sub.6)alkyl;
• --R.sub.26 represents a (C.sub.1 -C.sub.4)alkylcarbonyl, a benzyloxycarbonyl;
• a (C.sub.1 -C.sub.4)alkylcarbonyl;
• --R.sub.27 represents a hydrogen;
• a (C.sub.1 -C.sub.4)alkyl, a (C.sub.1 -C.sub.4)alkylcarbonyl;
• a group --CO--(CH.sub.2).sub.r -OH;
• a group SO.sub.2 R'.sub.7 ;
• --R.sub.28 represents a group --X--NR.sub.5 R.sub.6 ;
• --s=0 to 3;
• --t=0 to 3, on the condition that (s+t), in a same group, is greater than or equal to 1;
• --r=2to 5;
• --q=1 to 5;
• --T represents a direct bond or (C.sub.1 -C.sub.7)alkylene;
• --X represents a (C.sub.2 -C.sub.7)alkylene;
• --Y represents a (C.sub.1 -C.sub.7)alkylene:
• --Z represents a (C.sub.2 -C.sub.6)alkylene:
• --the group --NH--AA(OH) represents the residue of an amino acid:
• ##STR124## where X.sub.a is hydrogen and X'.sub.a is hydrogen, a (C.sub.1 -C.sub.5)alkyl or a non-aromatic C.sub.3 -C.sub.15 carbocyclic radical;
• or alternatively, X.sub.a and X'.sub.a, together with the carbon atom to which they are attached, form a non-aromatic C.sub.3 -C.sub.15 carbocycle;
• its salts and its quaternary ammonium salts formed with acyclic or cyclic tertiary amines and its solvates.