Novel substituted pyrazolo[4,3-e]diazepines, pharmaceutical compositions containing them, use as medicinal products and processes for preparing them

Compound of formula I below:

• 21
• in which:
• R1 is chosen from the following groups:
• hydrogen;
• linear or branched alkyl containing from 1 to 6 carbon atoms;
• cycloalkyl containing from 3 to 6 carbon atoms;
• alkylcycloalkyl comprising an alkyl group containing from 1 to 6 carbon atoms and a cycloalkyl group containing from 3 to 6 carbon atoms;
• aryl containing from 5 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• arylalkyl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• alkylaryl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• linear or branched alkenyl containing from 2 to 6 carbon atoms;
• the groups (CH2)nORB, (CH2)nCF3, (CH2)nC(O)RB, (CH2)nCOORB, (CH2)nOC(O)RA, (CH2)nSRB, (CH2)nC(S)RB, (CH2)nC(S)ORB, (CH2)nC(S)SRB, (CH2)nNRBRC, (CH2)nC(O)NRBRC, (CH2)nNRCC(O)RB, (CH2)nNRDC(O)NRDRB or (CH2)nZ, in which,
• RA is chosen from linear or branched alkyl containing from 1 to 6 carbon atoms;
• cycloalkyl containing from 3 to 6 carbon atoms;
• alkylcycloalkyl comprising an alkyl group containing from 1 to 6 carbon atoms and a cycloalkyl group containing from 3 to 6 carbon atoms;
• aryl containing from 5 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• arylalkyl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• alkylaryl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• linear or branched alkenyl containing from 2 to 6 carbon atoms;
• RB and RC, which may be identical or different, are chosen from:
• hydrogen;
• linear or branched alkyl containing from 1 to 6 carbon atoms;
• cycloalkyl containing from 3 to 6 carbon atoms;
• alkylcycloalkyl comprising an alkyl group containing from 1 to 6 carbon atoms and a cycloalkyl group containing from 3 to 6 carbon atoms;
• aryl containing from 5 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• arylalkyl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• alkylaryl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• linear or branched alkenyl containing from 2 to 6 carbon atoms;
• it being possible for RB and RC to form a ring containing from 5 to 7 atoms which can include one or more hetero atoms chosen from S, N and O;
• RD is hydrogen or linear or branched alkyl containing from 1 to 6 carbon atoms;
• Z is a halogen;
• and
• n is an integer from 0 to 4 inclusive;
• R2 is chosen from the following groups:
• linear or branched alkyl containing from 1 to 6 carbon atoms;
• alkylcycloalkyl comprising an alkyl group containing from 1 to 6 carbon atoms and a cycloalkyl group containing from 3 to 6 carbon atoms;
• cycloalkyl containing from 3 to 6 carbon atoms;
• aryl containing from 5 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• alkylaryl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• linear or branched alkenyl containing from 2 to 6 carbon atoms;
• the groups (CH2)mORB, (CH2)nCF3, (CH2)mC(O)RB, (CH2)mCOORB, (CH2)mOC(O)RA, (CH2)mSRB, (CH2)mC(S)RB, (CH2)mC(S)ORB, (CH2)mC(S)SRB, (CH2)mNRBRC, (CH2)mC(O)NRBRC, (CH2)mNRCC(O)RB, (CH2)mNRDC(O)NRDRB or (CH2)mZ, in which,
• RA, RB, RC RD and Z are as defined above, and
• m is an integer from 1 to 4 inclusive;
• n is an integer from 0 to 4 inclusive;
• R3 is chosen from the following groups:
• hydrogen;
• linear or branched alkyl containing from 1 to 6 carbon atoms;
• cycloalkyl containing from 3 to 6 carbon atoms;
• alkylcycloalkyl comprising an alkyl group containing from 1 to 6 carbon atoms and a cycloalkyl group containing from 3 to 6 carbon atoms;
• aryl containing from 5 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• arylalkyl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• alkylaryl containing from 6 to 10 carbon atoms, optionally interrupted with a hetero atom chosen from nitrogen, oxygen and sulphur;
• linear or branched alkenyl containing from 2 to 6 carbon atoms;
• the groups (CH2)nORB, (CH2)nCF3, (CH2)nC(O)RB, (CH2)nCOORB, (CH2)nOC(O)RA, (CH2)nSRB, (CH2)nC(S)RB, (CH2)nC(S)ORB, (CH2)nC(S)SRB, (CH2)nNRBRC, (CH2)nC(O)NRBRC, (CH2)nNRCC(O)RB, (CH2)nNRDC(O)NRDRB or (CH2)nZ, in which,
• RA, RB, RC RD and n are as defined above;
• the aryl, arylalkyl and alkylaryl groups defined above being unsubstituted or substituted on the aryl group with 1, 2 or 3 groups chosen from:
• halogen, hydroxyl, NO, NO2, CN, alkoxy containing from 1 to 4 carbon atoms, (CH2)nORB, (CH2)nNRBRC, (CH2)nNC(O)RB, (CH2)nHNSO2RB, (CH2)nN(SO2RB)2, CO2RB, CF3 and
• 22
• in which RB, RC and n are as defined above;
• and
• the dotted line present in formula I indicates that the bond between W and the carbon in position 5 may be:
• a single bond, in which case W represents a nitrogen atom substituted with a hydrogen atom,
• a double bond, and in this case W represents an unsubstituted nitrogen atom;
• X is S, O, N—CN or N—RB in which RB is as defined above;
• as well as the oxides, the tautomeric forms and the corresponding opticals isomers or the pharmaceutically acceptable derivatives of the compounds of formula I, with the proviso that when
• R1 represents a methyl group, R2 an ethyl group, W is N, X is an oxygen atom and the bond between W and the carbon in position 5 is a double bond, then
• R3 is neither an unsubstituted phenyl group nor a phenyl group bearing a fluorine atom in an ortho position as sole substituent.