Substituted pyrazoles, compositions containing these, method of production and use
View Patent ↗The disclosure relates to a compound of formula (I): and salts thereof; wherein Ar, L, A, X, R 1 , R 2 , R 3 , R 4 a, R 4 b, and R 5 are as defined in the disclosure; compositions comprising said compounds, methods for their preparation, intermediates thereto, and the use thereof, particularly as drugs.
1. A compound of formula (VIII):
wherein:
Ar is selected from the group consisting of: aryl and substituted aryl
R 4a is selected from the group consisting of: H and (C1-C4)alkyl;
R 4b is selected from the group consisting of: H and (C1-C4)alkyl;
R 5 is selected from the group consisting of: H, halogen, R 10 , CN, O(R 10 ), OC(O)(R 10 ), OS(O 2 )(R 10 ), N(R 10 )(R 11 ), N═C(R 10 )(R 11 ), N(R 10 )C(O)O(R 11 ), N(R 12 )C(O)N(R 10 )(R 11 ), N(R 12 )C(S)N(R 10 )(R 11 ), N(R 10 )S(O 2 )(R 11 ), C(O)(R 10 ), C(O)O(R 10 ), C(O)N(R 10 )(R 11 ), C(═N(R 11 ))(R 10 ), C(═N(OR 11 ))(R 10 ), S(R 10 ), S(O)(R 10 ), S(O 2 )(R 10 ), S(O 2 )O(R 10 ), S(O 2 )N(R 10 )(R 11 ); in which each R 10 , R 11 , R 12 is independently selected from the group consisting of H, alkyl, alkylene, alkynyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, substituted alkyl, substituted alkylene, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl and substituted heterocyclyl;
R 1 is selected from the group consisting of: H, R 6 , COR 6 , SO 2 R 6 , in which R 6 is chosen from H, OR 7 , NR 8 R 9 , alkyl, cycloalkyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, in which R 7 is chosen from H, phenyl and alkyl, and in which R 8 and R 9 are independently selected from the group consisting of H, alkyl, cycloalkyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, or alternatively R 8 and R 9 are linked together to form a saturated 5- to 8-membered ring containing from 0 to 3 heteroatoms chosen from O, S and N;
X is selected from the group consisting of: O and NH;
R′ 3 is R 3 or a precursor of R 3 ; and
R 3 is selected from the group consisting of: H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl.
2. The compound according to claim 1 , wherein R 4a and R 4b are H.
3. The compound according to claim 1 , wherein R 4a is H and R 4b is (C1-C4)alkyl.
4. The compound according to claim 1 , wherein R 4a is (C1-C4)alkyl and R 4b is H.
5. The compound according to claim 1 , wherein R 1 is H.
6. The compound according to claim 1 , wherein R 3 is H and X is NH.
7. The compound according to claim 1 , wherein R 3 is methyl and X is O.
8. The compound according to claim 1 , wherein R 5 is H.
9. The compound according to claim 1 , wherein Ar—NH 2 is:
In which each X1, X2, X3 and X4 is independently chosen from C—R′ 5 , in which R′ 5 has the same definition as R 5 , wherein R 5 is H.