5,6-diaryl pyridines substituted in the 2- and 3-position, preparation thereof and therapeutic use thereof
View Patent ↗The invention relates to compounds corresponding to formula (I): In which Ar 1 , Ar 2 , Q, Y, Z, Alk′, k and m are as defined herein. The invention further relates to their preparations, intermediates therefor and their therapeutic uses.
1. A compound of formula (I):
in which:
Q represents an oxygen atom, a sulfur atom or a radical —NR 1 — in which R 1 represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
Z represents a group —N(R 3 )XR 4 , —N(R 3 )COOR 5 or —OCON(R 3 )R 5 , wherein
X represents a group —CO—, —SO 2 —, —CON(R 6 )— or —CSN(R 6 )—;
R 3 represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
R 4 represents:
a non-aromatic (C 3 -C 12 ) carbocyclic radical, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a group (C 1 -C 4 )alkyl, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio and cyano;
a saturated or unsaturated, oxygen-bearing, sulfur-bearing or nitrogen-bearing heterocyclic radical of 3 to 8 atoms, which is unsubstituted or substituted with one or more identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano, nitro and an oxo group;
an indolyl which is unsubstituted or substituted with a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, hydroxyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano or nitro;
a tetrahydronaphthyl; a naphthyl;
a benzothiophenyl or a benzofuryl;
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
a benzodioxyl;
a phenoxymethylene or a 1-phenoxyethylene, the phenyl groups being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ; the methylene or ethylene groups being unsubstituted or substituted one or more times with identical or different substituents chosen from a group (C 1 -C 4 )alkyl or with a (C 3 -C 7 )cycloalkyl;
a phenylcyclopropyl, the phenyl group being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
a (C 1 -C 2 )alkylene substituted with one or two identical or different substituents chosen from:
(i) a C 3 -C 12 non-aromatic carbocyclic radical which is unsubstituted or substituted one or more times with a group (C 1 -C 4 )alkyl, which may be identical or different;
(ii) a phenyl which is unsubstituted or substituted with one or more substituents, which may be identical or different, chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkanoyl, cyano, nitro, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
(iii) a saturated or unsaturated, oxygen-bearing, sulfur-bearing or nitrogen-bearing heterocyclic radical of 3 to 8 atoms, which is unsubstituted or substituted with one or more substituents, which may be identical or different, chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano or nitro;
with the proviso that, when X represents a group —CON(R 6 )— or —CSN(R 6 )—, R 4 is a group (C 1 -C 6 )alkanoyl or a benzoyl or benzylcarbonyl group, the phenyl group of the said groups being unsubstituted or substituted with one or more identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
R 5 represents a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom or a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, cyano, nitro, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
R 6 represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
or R 4 and R 6 , together with the nitrogen atom to which they are attached, constitute a heterocyclic radical of 3 to 8 atoms, optionally containing a second heteroatom chosen from an oxygen, sulfur or nitrogen atom, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a group (C 1 -C 4 )alkyl; a group (C 1 -C 4 )alkanoyl; a group NR 7 R 8 or CONR 7 R 8 , a phenyl group; the said phenyl group being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy or trifluoromethyl, (C 1 -C 4 )alkylthio, trifluoromethoxy, trifluoromethylthio or a group OS(O) n Alk, S(O) n Alk or NR 7 R 8 ;
R 7 and R 8 represent, independently of each other, a hydrogen atom, a group (C 1 -C 4 )alkyl or R 7 and R 8 , together with the nitrogen atom to which they are attached, constitute a saturated heterocyclic radical of 4 to 8 atoms possibly containing another heteroatom chosen from a nitrogen, oxygen or sulfur atom;
Ar 1 and Ar 2 represent, independently of each other, a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, cyano, nitro, a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
Y represents a group —R 1′ , —OR 5′ , —N(R 3′ )X′R 4′ , —N(R 3′ )COOR 5′ , —NR 7′ R 8′ , —CON(R 3′ )R 5′ , —CSN(R 3′ R 5′ , —C(O)R 2′ , —C(O)—O—R 2′ , —SO 2 R 2′ , —SO 2 N(R 3′ )R 5 or —OCON(R 3′ )R 5′ ;
R 1′ represents a radical —CN or a saturated or unsaturated, oxygen-bearing, sulfur-bearing or nitrogen-bearing heterocyclic radical of 3 to 8 atoms, possibly containing a second heteroatom chosen from nitrogen, oxygen and sulfur, which is unsubstituted or substituted with one or more identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano, nitro or with an oxo group;
X′ represents a group —CO—, —SO 2 —, —CON(R 6′ )— or —CSN(R 6′ )—;
R 2′ represents:
a group (C 1 -C 10 )alkyl, which is unsubstituted or substituted with a substituent chosen from CF 3 , (C 1 -C 4 )alkoxy and hydroxyl;
a non-aromatic (C 3 -C 12 ) carbocyclic radical, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy,
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, cyano, nitro, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, S(O) n Alk or OS(O) n Alk;
a benzyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, cyano, nitro, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, S(O) n Alk or OS(O) n Alk;
R 3′ represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
R 4′ represents:
a group (C 1 -C 10 )alkyl, which is unsubstituted or substituted with a group CF 3 ;
a non-aromatic (C 3 -C 12 ) carbocyclic radical, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a group (C 1 -C 4 )alkyl, hydroxyl, a halogen atom, a trifluoromethyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio or cyano;
a saturated or unsaturated, oxygen-bearing, sulfur-bearing or nitrogen-bearing heterocyclic radical of 3 to 8 atoms, which is unsubstituted or substituted with one or more identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano, nitro and an oxo group;
an indolyl which is unsubstituted or substituted with a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, hydroxyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano or nitro;
a tetrahydronaphthyl; a naphthyl;
a benzothiophenyl or a benzofuryl;
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
a benzodioxyl;
a phenoxymethylene or a 1-phenoxyethylene, the phenyl groups being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ; the methylene or ethylene groups being unsubstituted or substituted one or more times with a group (C 1 -C 4 )alkyl or with a (C 3 -C 7 )cycloalkyl;
a phenylcyclopropyl, the phenyl group being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7′ R 8′ ;
a (C 1 -C 2 )alkylene substituted with one or two identical or different substituents chosen from:
(i) a C 3 -C 12 non-aromatic carbocyclic radical which is unsubstituted or substituted one or more times with a group (C 1 -C 4 )alkyl;
(ii) a phenyl which is unsubstituted or substituted with one or more substituents, which may be identical or different, chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkanoyl, cyano, nitro, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7′ R 8′ ;
(iii) a saturated or unsaturated, oxygen-bearing, sulfur-bearing or nitrogen-bearing heterocyclic radical of 3 to 8 atoms, which is unsubstituted or substituted with one or more substituents, which may be identical or different, chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano or nitro;
with the proviso that, when X′ represents a group —CON(R 6′ — or —CSN(R 6′ )—, R 4′ is a group (C 1 -C 6 )alkanoyl or a benzoyl or benzylcarbonyl group, the phenyl group of the said groups being unsubstituted or substituted with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7′ R 8′ ;
R 5′ represents:
a hydrogen atom;
a group (C 1 -C 10 )alkyl, which is unsubstituted or substituted with a group CF 3 ;
a non-aromatic (C 3 -C 12 ) carbocyclic radical, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl or (C 1 -C 4 )alkoxy;
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, cyano, nitro, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, S(O) n Alk, OS(O) n Alk or NR 7′ R 8′ ,
or R 3′ and R 5′ together with the nitrogen atom to which they are attached, constitute a heterocyclic radical of 3 to 8 atoms, optionally containing a second heteroatom chosen from an oxygen, sulfur or nitrogen atom, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a trifluoromethyl, a group (C 1 -C 4 )alkyl, a phenyl group or a group NR 7′ R 8′ a group CONR 7′ R 8′ ; the said group (C 1 -C 4 )alkyl being unsubstituted or substituted with a trifluoromethyl group; and the said phenyl group being unsubstituted or substituted one or more times with a halogen atom, a group (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, trifluoromethyl, (C 1 -C 4 )alkylthio, trifluoromethoxy, trifluoromethylthio, OS(O) n Alk or S(O) n Alk;
R 6′ represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
or R 4′ and R 6′ together with the nitrogen atom to which they are attached, constitute a heterocyclic radical of 3 to 8 atoms, optionally containing a second heteroatom chosen from an oxygen, sulfur or nitrogen atom, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a group (C 1 -C 4 )alkyl, a phenyl group, a halogen atom, a hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, an oxo group, (C 1 -C 4 )alkanoyl, NR 7′ R 8′ or CONR 7′ R 8′ ; the said group (C 1 -C 4 )alkyl being unsubstituted or substituted with a trifluoromethyl group; and the said phenyl group being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, trifluoromethyl, (C 1 -C 4 )alkylthio, trifluoromethoxy, trifluoromethylthio, OS(O) n Alk or S(O) n Alk;
R 7′ and R 8′ represent, independently of each other, a hydrogen atom, a group (C 1 -C 4 )alkyl or R 7′ and R 8′ , together with the nitrogen atom to which they are attached, constitute a saturated heterocyclic radical of 4 to 8 atoms possibly containing another heteroatom chosen from a nitrogen, oxygen or sulfur atom;
Alk represents a linear or branched (C 1 -C 7 )alkyl group;
Alk′ represents a linear or branched (C 1 -C 5 )alkyl group;
n represents 0, 1 or 2;
k represents 1; and
m represents 0 or 1;
or a salt thereof.
2. The compound of formula (I) according to claim 1 , wherein:
Y represents a group —C(O)R 2′ —SO 2 R 2′ ; —CON(R 3′ )R 5′ —CSNR 3′ R 5′ , —C(O)—O—R 2′ —NR 7′ R 8′ , —OR 5′ or —R 1′ ;
k represents 1;
Q represents the radical NR 1 wherein R 1 is a hydrogen atom or a methyl group; and
Alk′ represents a linear (C 2 -C 4 )alkyl group;
or a salt thereof.
3. The compound according to claim 2 , wherein:
R 2′ represents:
a group (C 1 -C 10 )alkyl, which is unsubstituted or substituted with a substituent chosen from CF 3 , (C 1 -C 4 )alkoxy and hydroxyl;
a non-aromatic (C 3 -C 12 ) carbocyclic radical, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, hydroxyl and trifluoromethyl;
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio and trifluoromethylthio;
a benzyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio and trifluoromethylthio;
R 3′ represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
R 5′ represents:
a hydrogen atom;
a group (C 1 -C 10 )alkyl, which is unsubstituted or substituted with a group CF 3 ;
a non-aromatic (C 3 -C 12 ) carbocyclic radical, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy;
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio or trifluoromethylthio;
R 3′ and R 5′ , together with the nitrogen atom to which they are attached, constitute a heterocyclic radical of 3 to 8 atoms, possibly containing a second heteroatom chosen from an oxygen, sulfur or nitrogen atom, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a trifluoromethyl or a group (C 1 -C 4 )alkyl, which is unsubstituted or substituted with a trifluoromethyl; and
R 7′ and R 8′ represent, independently of each other, a hydrogen atom or a group (C 1 -C 4 )alkyl, or R 7′ and R 8′ , together with the nitrogen atom to which they are attached, constitute a saturated heterocyclic radical of 4 to 8 atoms possibly containing another heteroatom chosen from a nitrogen, oxygen or sulfur atom;
or a salt thereof.
4. The compound of formula (I) according to claim 1 , wherein:
Y represents —C(O)R 2′ , —SO 2 R 2′ , or —CONHR 5′ ;
or a salt thereof.
5. The compound of formula (I) according to claim 1 , wherein:
Y representing a group —SO 2 R 2′ , —CON(R 3′ )R 5′ , —NR 7′ R 8′ ,
—OR 5′ , or —SO 2 N(R 3′ )R 5′ ;
k represents 1;
Q represents an oxygen atom; and
Alk′ represents a linear (C 2 -C 4 )alkyl group;
or a salt thereof.
6. The compound according to claim 5 , wherein:
R 2′ represents:
a group (C 1 -C 10 )alkyl, which is unsubstituted or substituted with a substituent chosen from CF 3 , (C 1 -C 4 )alkoxy and hydroxyl;
a (C 3 -C 12 ) non-aromatic carbocyclic group, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy;
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio and trifluoromethylthio;
R 3′ represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
R 5′ represents:
a hydrogen atom;
a group (C 1 -C 10 )alkyl, which is unsubstituted or substituted with a group CF 3 ;
a non-aromatic (C 3 -C 12 ) carbocyclic radical, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl or (C 1 -C 4 )alkoxy;
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio and trifluoromethylthio;
R 3′ and R 5′ , together with the nitrogen atom to which they are attached, constitute a heterocyclic radical of 3 to 8 atoms, possibly containing a second heteroatom chosen from an oxygen, sulfur or nitrogen atom, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a trifluoromethyl or a group (C 1 -C 4 )alkyl, which is unsubstituted or substituted with a trifluoromethyl; and
R 7′ and R 8′ represent, independently of each other, a hydrogen atom, a group (C 1 -C 4 )alkyl or R 7′ and R 8′ , together with the nitrogen atom to which they are attached, constitute a saturated heterocyclic radical of 4 to 8 atoms possibly containing another heteroatom chosen from a nitrogen, oxygen or sulfur atom;
or a salt thereof.
7. The compound of formula (I) according to claim 1 , wherein:
Z represents —N(R 3 )COR 4 , —N(R 3 )SO 2 R 4 , or —N(R 3 )CON(R 6 )R 4 ;
or a salt thereof.
8. The compound of formula (I) according to claim 1 , which is selected from the group consisting of:
N-{[6-(4-bromophenyl)-5-(2,4-dichlorophenyl)-2-{[(hydroxyacetyl)amino]methyl}pyrid-3-yl]methyl}-4-[(trifluoromethyl)thio]benzamide;
N-{[6-(4-bromophenyl)-5-(2,4-dichlorophenyl)-2-{[(2-hydroxyethyl)(methyl)amino]methyl}pyrid-3-yl]methyl}-4-(trifluoromethyl)benzamide;
N-{[2-{[(2-amino-2-oxoethyl)(methyl)amino]methyl}-6-(4-bromophenyl)-5-(2,4-dichlorophenyl)pyrid-3-yl]methyl}-4-(trifluoromethyl)benzamide;
N-{[6-(4-bromophenyl)-5-(2,4-dichlorophenyl)-2-({methyl [2-(methylsulfonyl)-ethyl]amino}methyl)pyrid-3-yl]methyl}-4-(trifluoromethyl)benzamide;
N-{[6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-2-{[(hydroxyacetyl)amino]methyl}pyrid-3-yl]methyl}-4-[(trifluoromethyl)thio]benzamide;
N-{[6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-3-({[(2-fluorobenzyl)carbamoyl]-amino}methyl)pyrid-2-yl]methyl}-2-hydroxyacetamide;
N-{[6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-2-{[(hydroxyacetyl)amino]methyl}pyrid-3-yl]methyl}-4-(trifluoromethyl)benzamide; and
N-{[6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-2-{[(3-hydroxypropanoyl)amino]-methyl}pyrid-3-yl]methyl}-4-(trifluoromethyl)benzamide;
or a salt thereof.
9. The compound of formula (I) according to claim 8 , which is selected from the group consisting of:
N-{[6-(4-bromophenyl)-5-(2,4-dichlorophenyl)-2-{[(hydroxyacetyl)amino]methyl}pyrid-3-yl]methyl}-4-[(trifluoromethyl)thio]benzamide;
N-{[6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-2-{[(hydroxyacetyl)amino]methyl}pyrid-3-yl]methyl}-4-[(trifluoromethyl)thio]benzamide;
N-{[6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-3-({[(2-fluorobenzyl)carbamoyl]-amino}methyl)pyrid-2-yl]methyl}-2-hydroxyacetamide; and
N-{[6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-2-{[(hydroxyacetyl)amino]methyl}pyrid-3-yl]methyl}-4-(trifluoromethyl)benzamide;
or a salt thereof.
10. A compound of formula (XX):
in which
Z represents a group —N(R 3 )XR 4 , —N(R 3 )COOR 5 or —OCON(R 3 )R 5 , wherein
X represents a group —CO—, —SO 2 —, —CON(R 6 )— or —CSN(R 6 )—;
R 3 represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
R 4 represents:
a non-aromatic (C 3 -C 12 ) carbocyclic radical, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a group (C 1 -C 4 )alkyl, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio and cyano;
a saturated or unsaturated, oxygen-bearing, sulfur-bearing or nitrogen-bearing heterocyclic radical of 3 to 8 atoms, which is unsubstituted or substituted with one or more identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano, nitro and an oxo group;
an indolyl which is unsubstituted or substituted with a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, hydroxyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano or nitro;
a tetrahydronaphthyl; a naphthyl;
a benzothiophenyl or a benzofuryl;
a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
a benzodioxyl;
a phenoxymethylene or a 1-phenoxyethylene, the phenyl groups being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ; the methylene or ethylene groups being unsubstituted or substituted one or more times with identical or different substituents chosen from a group (C 1 -C 4 )alkyl or with a (C 3 -C 7 )cycloalkyl;
a phenylcyclopropyl, the phenyl group being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
a (C 1 -C 2 )alkylene substituted with one or two identical or different substituents chosen from:
(i) a C 3 -C 12 non-aromatic carbocyclic radical which is unsubstituted or substituted one or more times with a group (C 1 -C 4 )alkyl, which may be identical or different;
(ii) a phenyl which is unsubstituted or substituted with one or more substituents, which may be identical or different, chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkanoyl, cyano, nitro, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
(iii) a saturated or unsaturated, oxygen-bearing, sulfur-bearing or nitrogen-bearing heterocyclic radical of 3 to 8 atoms, which is unsubstituted or substituted with one or more substituents, which may be identical or different, chosen from a halogen atom, a group (C 1 -C 4 )alkyl, hydroxyl, trifluoromethyl, (C 1 -C 4 )alkoxy, trifluoromethoxy, trifluoromethylthio, (C 1 -C 4 )alkylthio, cyano or nitro;
with the proviso that, when X represents a group —CON(R 6 )— or —CSN(R 6 )—, R 4 is a group (C 1 -C 6 )alkanoyl or a benzoyl or benzylcarbonyl group, the phenyl group of the said groups being unsubstituted or substituted with one or more identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, cyano, nitro, (C 1 -C 4 )alkanoyl, phenyl or a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
R 5 represents a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom or a group (C 1 -C 4 )alkyl, trifluoromethyl, trifluoromethoxy, cyano, nitro, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, trifluoromethylthio, a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
R 6 represents a hydrogen atom or a group (C 1 -C 4 )alkyl;
or R 4 and R 6 , together with the nitrogen atom to which they are attached, constitute a heterocyclic radical of 3 to 8 atoms, optionally containing a second heteroatom chosen from an oxygen, sulfur or nitrogen atom, which is unsubstituted or substituted one or more times with identical or different substituents chosen from a group (C 1 -C 4 )alkyl; a group (C 1 -C 4 )alkanoyl; a group NR 7 R 9 or CONR 7 R 8 , a phenyl group; the said phenyl group being unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy or trifluoromethyl, (C 1 -C 4 )alkylthio, trifluoromethoxy, trifluoromethylthio or a group OS(O) n Alk, S(O) n Alk or NR 7 R 8 ;
R 7 and R 8 represent, independently of each other, a hydrogen atom, a group (C 1 -C 4 )alkyl or R 7 and R 8 , together with the nitrogen atom to which they are attached, constitute a saturated heterocyclic radical of 4 to 8 atoms possibly containing another heteroatom chosen from a nitrogen, oxygen or sulfur atom;
Ar 1 and Ar 2 represent, independently of each other, a phenyl which is unsubstituted or substituted one or more times with identical or different substituents chosen from a halogen atom, a group (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, cyano, nitro, a group S(O) n Alk, OS(O) n Alk or NR 7 R 8 ;
Alk represents a linear or branched (C 1 -C 7 )alkyl group; and
n represents 0, 1 or 2.
11. The compound according to claim 10 , wherein Z represents —NH—SO 2 —R 4 , —NH—COR 4 , —NH—CO—NHR 4 or —NH—CS—NHR 4 .
12. A pharmaceutical composition comprising a compound of formula (I) according to claim 1 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.
13. A pharmaceutical composition comprising a compound of formula (I) according to claim 3 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.
14. A pharmaceutical composition comprising a compound of formula (I) according to claim 8 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.
15. A pharmaceutical composition comprising a compound of formula (I) according to claim 9 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient.