Phenylacetamides suitable as protein kinase inhibitors

1. A compound of the formula I,

wherein

each of R1 and R2, independently of the other, is selected from the group consisting of hydrogen, halo and C 1 -C 7 -alkyl;

R3 is absent if Z is nitrogen or, if Z is C, then R3 is hydrogen, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl;

X is N (nitrogen) or CH (hydrogen-substituted carbon),

Y is CH or N,

Z is C or N, and

Q is a moiety of the formula (A)

wherein

R4 is hydrogen, halo, unsubstituted or substituted amino, unsubstituted or substituted aryl, unsubstituted or substituted heterocyclyl bound via a ring atom other than nitrogen, unsubstituted or substituted cycloalkyl, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl or unsubstituted or substituted alkynyl;

R5 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted amino, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl; and

R6 is hydrogen, unsubstituted or substituted cycloalkyl or unsubstituted or substituted alkyl;

or a moiety of the formula (B)

wherein

R7 is unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl and

R8 is alkyl or cycloalkyl;

where the asterisk * in formulae (A) and (B) marks the bond through which the moiety is bound to the NH of the amide group in formula I; and

(a) each of R9 and R10, independently of the other, is selected from the group consisting of hydrogen, hydroxyl and C 1 -C 7 -alkyl; or

(b) R9 and R10 together represent oxo; or

R1 and R9 together form a group —C(O)—CH2—or —CH2—CH2—, R2 is selected from the group consisting of hydrogen, halo and C 1 -C 7 -alkyl, and R10 represents hydrogen;

or a pharmaceutically acceptable salt thereof.

2. A compound of the formula I according to claim wherein each of R1 and R2, independently of the other, is selected from the group consisting of hydrogen, halo and C1-C7-alkyl;

R3 is absent if Z is nitrogen or, if Z is C, then R3 is hydrogen, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl;

R9 and R10 both represent hydrogen; and

X is N or CH,

Y is CH or N,

Z is C or N,

and

Q is a moiety of the formula (A) wherein

R4 is hydrogen, halo, unsubstituted or substituted amino, unsubstituted or substituted aryl, unsubstituted or substituted heterocyclyl bound via a ring atom other than nitrogen, unsubstituted or substituted cycloalkyl, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl or unsubstituted or substituted alkynyl;

R5 is hydrogen, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl; and

R6 is unsubstituted or substituted cycloalkyl or unsubstituted or substituted alkyl;

or a moiety of the formula (B) wherein

R7 is unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl and

R8 is alkyl or cycloalkyl;

where the asterisk * in formulae (A) and (B) marks the bond through which the moiety is bound to the NH of the amide group in formula I;

or a pharmaceutically acceptable salt thereof.

3. A compound of the formula I according to claim 2 wherein each of R1 and R2, independently of the other, is selected from the group consisting of hydrogen, halo and C 1 -C 7 -alkyl;

R3 is absent if Z is nitrogen or, if Z is C, then R3 is hydrogen or unsubstituted or substituted aryl;

R9 and R10 both represent hydrogen;

X is N or CH,

Y is CH;

Z is C or N

and

Q is a moiety of the formula (A)

wherein R4 is hydrogen, halo, unsubstituted or substituted amino, unsubstituted or substituted aryl, unsubstituted or substituted alkyl or unsubstituted or substituted alkynyl;

R5 is hydrogen or unsubstituted or substituted aryl; and

R6 is unsubstituted or substituted alkyl;

or a moiety of the formula (B)

wherein

R7 is unsubstituted or substituted aryl and

R8 is alkyl;

or a pharmaceutically acceptable salt thereof.

4. A compound of the formula I according to claim 2 , wherein

R1 is hydrogen, chloro, or C 1 -C 7 alkyl,

R2 is hydrogen, chloro, or C 1 -C 7 alkyl,

R3 is absent if Z is nitrogen or, if Z is C, then R3 is hydrogen, phenyl that is unsubstituted or substituted by one or more moieties independently selected from C 1 -C 7 alkyl, halo, hydroxy, C 1 -C 7 -alkoxy and cyano,

R 9 and RIO both represent hydrogen,

X is N or CH,

Y is CH,

Z is C or N,

Q is a moiety of the formula (A) wherein

R4 is hydrogen, iodo, phenyl that is unsubstituted or substituted by one or more moieties independently selected from C 1 -C 7 -alkyl, halo, hydroxy, C 1 -C 7 -alkoxy and cyano; N,N-di-(C 1 -C 7 -alkyl)-amino-C 1 -C 7 alkyl, N-[(N-mono- or N,N-di-(C 1 -C 7 -alkyl)-amino)-C 1 -C 7 -alkyl]-N—C 1 -C 7 -alkylamino, pyrrolidino, piperidino, piperazino, 4-C 1 -C 7 -alkylpiperazino 1-C 1 -C 7 -alkylpiperidin-4-yl, morpholino, thiomorpholino, pyrrolidino-C 1 -C 7 -alkyl, piperidino-C 1 -C 7 -alkyl, piperazino-C 1 -C 7 -alkyl, 4-C 1 -C 7 -alkylpiperazino-C 1 -C 7 -alkyl, morpholino-C1-C7-alkyl, thiomorpholino-C1-C 7 -alkyl, N-piperidin-(2, 3 or 4)-yl-amino, N—C 1 -C 7 -alkyl-N-piperidin-ylamino wherein piperi-dinyl is bound via a ring carbon and is unsubstituted or substituted by lower alkyl, or N,N-di-(lower alkyl, phenyl and/ or phenyl lower alkyl)-C 3 -C 7 -alkynyl;

R5 is hydrogen or phenyl that is unsubstituted or substituted by one or more moieties independently selected from C 1 -C 7 -alkyl, halo, hydroxy, C 1 -C 7 -alkoxy and cyano; and

R6 is C 1 -C 7 -alkyl, C 3 -C 8 -cycloalkyl or halo-C 1 -C 7 -alkyl, trifluoromethyl, or a moiety of the formula (B) wherein

R7 is phenyl that is unsubstituted or substituted by one or more moieties independently selected from C 1 -C 7 -alkyl, halo, hydroxy, C 1 -C 7 -alkoxy and cyano; and

R8 is C 3 -C 8 cycloalkyl or C 1 -C 7 -alkyl;

or a pharmaceutically acceptable salt thereof.

5. A compound of the formula I according to claims 2 , wherein

R1 is hydrogen,

R2 is hydrogen or chloro,

R3 is absent if Z is nitrogen or, if Z is C, then R3 is hydrogen, phenyl that is unsubstituted or substituted by C 1 -C 7 -alkoxy,

R9 and R10 both represent hydrogen,

X is N or CH,

Y is CH,

Z is C or N,

Q is a moiety of the formula (A) wherein

R4 is hydrogen, iodo, phenyl that is unsubstituted or substituted by-chloro, bromo, cyano;

N—[(N-mono- or N,N-di-(C 1 -C 7 -alkyl)-amino)—C 1 -C 7 -alkyl]-N—C 1 -C 7 -alkylamino, N- 2 -[N—(N,N -dimethylamino)-ethyl-N-methyl-amino or N—(N,N-dimethylamino)-methyl-N-methyl-amino, pyrrolidino -C 1 -C 7 -alkyl, piperazino-C 1 -C 7 -alkyl, 4-C 1 -C 7 -alkylpiperazino-C 1 -C 7 -alkyl, N—C 1 -C 7 -alkyl-N-piperidin-ylamino wherein piperidinyl is bound via a ring carbon and is unsubstituted or substituted by lower alkyl, or N,N-di-(lower alkyl, phenyl and/ or phenyl lower alkyl)-C 3 -C 7 -alkynyl;

R5 is hydrogen or phenyl that is unsubstituted or substituted by C 1 -C 7 -alkoxy, and

R6 is halo-C 1 -C 7 -alkyl,

or a moiety of the formula (B) wherein

R7 is phenyl that is unsubstituted or substituted by C 1 -C 7 -alkyl; and

R8 is C 1 -C 7 -alkyl;

or a pharmaceutically acceptable salt thereof.

6. A compound of the formula I according to claim 1 wherein each of R1 and R2, independently of the other, is selected from the group consisting of hydrogen, halo and C1-C7-alkyl;

R3 is absent if Z is nitrogen or, if Z is C, then R3 is hydrogen or unsubstituted or substituted aryl;

X is N or CH,

Y is CH,

Z is C or N, and

Q is a moiety of the formula (A) wherein

R4 is hydrogen, halo, unsubstituted or substituted amino, unsubstituted or substituted aryl, unsubstituted or substituted heterocyclyl bound via a ring atom other than nitrogen, unsubstituted or substituted cycloalkyl, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl or unsubstituted or substituted alkynyl;

R5 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted amino, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl; and

R6 is hydrogen, unsubstituted or substituted cycloalkyl or unsubstituted or substituted alkyl;

or a moiety of the formula (B) wherein

R7 is unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl and

R8 is alkyl or cycloalkyl;

where the asterisk * in formulae (A) and (B) marks the bond through which the moiety is bound to the NH of the amide group in formula I; and

(a) each of R9 and R10, independently of the other, is selected from the group consisting of hydrogen, hydroxyl and C 1 -C 7 -alkyl; or

(b) R9 and R10 together represent oxo; or

R1 and R9 together form a group —C(O)—CH2—or —CH2—CH2—, R2 is selected from the group consisting of hydrogen, halo and C 1 -C 7 -alkyl, and R10 represents hydrogen;

or a pharmaceutically acceptable salt thereof.

7. A compound of the formula I according to claim 1 wherein each of R1 and R2, independently of the other, is selected from the group consisting of hydrogen, halo and C 1 -C 7 -alkyl;

R3 is absent if Z is nitrogen or, if Z is C, the R3 is hydrogen or unsubstituted or substituted aryl;

X is N or CH,

Y is CH,

Z is C or N, and

Q is a moiety of the formula (A) wherein

R4 is hydrogen, halo, unsubstituted or substituted amino, unsubstituted or substituted aryl, unsubstituted or substituted heterocyclyl bound via a ring atom other than nitrogen, unsubstituted or substituted alkyl or unsubstituted or substituted alkynyl;

R5 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted amino, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl; and

R6 is hydrogen or substituted alkyl;

or a moiety of the formula (B) wherein

R7 is unsubstituted or substituted aryl and

R8 is alkyl or cycloalkyl;

where the asterisk * in formulae (A) and (B) marks the bond through which the moiety is bound to the NH of the amide group in formula I; and

(a) each of R9 and R10, independently of the other, is selected from the group consisting of hydrogen, hydroxyl and C 1 -C 7 -alkyl; or

(b) R9 and R10 together represent oxo; or

R1 and R9 together form a group —C(O)—CH2—or —CH2—CH2—, R2 is selected from the group consisting of hydrogen, halo and C 1 -C 7 -alkyl, and R10 represents hydrogen;

or a pharmaceutically acceptable salt thereof.

8. A compound of the formula I according to claim 1 wherein each of R1 and R2, independently of the other, is selected from the group consisting of hydrogen, halo and C 1 -C 7 alkyl;

R3 is absent if Z is nitrogen or, if Z is C, then R3 is hydrogen or unsubstituted or substituted aryl;

X is N or CH,

Y is CH,

Z is C or N, and

Q is a moiety of the formula (A) wherein

R4 is hydrogen, halo, unsubstituted or substituted amino, unsubstituted or substituted aryl, unsubstituted or substituted heterocyclyl bound via a ring atom other than nitrogen, unsubstituted or substituted alkyl or unsubstituted or substituted alkynyl;

R5 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted amino, unsubstituted or substituted aryl or unsubstituted or substituted heterocyclyl; and

R6 is hydrogen or substituted alkyl;

or a moiety of the formula (B) wherein

R7 is unsubstituted or substituted aryl and

R8 is alkyl or cycloalkyl;

where the asterisk * in formulae (A) and (B) marks the bond through which the moiety is bound to the NH of the amide group in formula I; and

(a) each of R9 and R10, independently of the other, is selected from the group consisting of hydrogen, hydroxyl and C 1 -C 7 alkyl; or

(b) R9 and R10 together represent oxo; or

R1 and R9 together form a group —C(O)—CH2—or —CH2—CH2—, R2 is selected from the group consisting of hydrogen, halo and C 1 -C 7 -alkyl, and R10 represents hydrogen;

or a pharmaceutically acceptable salt thereof.

9. A compound of the formula I, selected from the group of compounds consisting of

2-(4-iminidazo[4,5-c]pyridin-1-yl-phenyl)-N-(3-trifluoromethyl-phenyl]-acetamide;

2-(4-imidazo[4,5-c]pyridin-1-yl-phenyl)-N-[4-(4-methyl-piperazin-1-ylmethyl)-3-trfluoromethyl-phenyl ]-acetamide;

N-(3′-chloro-2-trifluoromethyl-biphen-4-yl)-2-(4-imidazo[4,5-c]pyridin-1-yl-phenyl)-acetamide;

N-(3′-bromo-2-trffluoromethyl-biphen-4-yl)-2-(4-imidazo[4,5-c]pyridin-1-yl-phenyl)-acetamide;

N-{4-[(3-dimethylamino-propyl)-methyl-amino]-3-trffluoromethyl-phenyl}-2-(4-imidazo[4,5-c ]pyridin-1-yl-phenyl)-acetamide;

N-{4-[(2-dimethylamino-ethyl)-methyl-amino]-3-trifluoromethyl-phenyl}-2-(4-imidazo[4,5-c ]pyridin-1-yl-phenyl)-acetamide;

N-(3′-bromo-2-trfluoromethyl-biphen-4-yl)-2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-acetamide;

2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl -acetamide;

N[4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl) -acetamide;

2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N[4-(4-isopropyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl -acetamide;

N-{4-[(3-dimethylamino-propyl)-methyl-amino]-3-trfluoromethyl-phenyl}-2-(4-imidazo[4,5-b ]pyridin-3-yl-phenyl)-acetamide;

2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N-(4-iodo-3-trifluoromethyl-phenyl)-acetamide;

N-(4′-cyano-2-trifluoromethyl-biphen-4-yl)-2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)- acetamide;

2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N-(4′-methoxy-5-trifluoromethyl-biphen-3-yl)-acetamide;

2-(4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N-{4-[methyl-(1-methyl-piperidin-4-yl)-amino]-3-trifluoromethyl -phenyl}-acetamide;

2-(2-chloro-4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N[4-(4-isopropyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl-acetamide;

2-(2-chloro-4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N[4-(4-methyll-piperazin-1-ylmethyl)-3-trifluoromethyl -phenyl-acetamide;

2-(2-chloro-4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N-[4-(4-ethyll-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl-acetamide;

2-(2-chloro-4-imidazo[4,5-b]pyridin-3-yl-phenyl)-N-{4-[(3-dimethylamino-propyl)-methyl-amino]-3-trifluoromethyl-phenyl}-acetamide;

2-(4-benzoimidazol-1-yl-phenyl)-N-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-acetamide;

2-(4-benzoimidazol-1-yl-phenyl)-N-{4-[methyl-(1-methyl-piperidin-4-yl)-amino]-3-trifluoromethyl-phenyl }-acetamide;

2-(4-benzoimidazol-1-yl-phenyl)-N-{4-[(3-dimethylamino-propyl)-methyl-amino]-3-trifluoromethyl-phenyl }-acetamide;

2-(4-benzoimidazol-1-yl-phenyl)-N-{4-[(2-dimethylamino-ethyl)-methyl-amino]-3-trifluoromethyl-phenyl }-acetamide;

2-(4-benzoimidazol-1-yl-phenyl)-N-(4′-cyano-2-trifluoromethyl-biphen-4-yl)- acetamide;

2-{4-[5-(4-methoxy-phenyl)-benzoim idazol-1-yl]-phenyl}-N-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl-acetamide;

N-[4-(3-dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenyl]-2-(4-imidazo[4,5-b]pyridin-3-yl -phenyl)-acetamide and

N-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-2-(4-imidazo[4,5-b]pyridine-3-yl-phenyl)-acetamide, or a pharmaceutically acceptable salt thereof

10. A pharmaceutical preparation comprising at least a compound of the formula I, or a pharmaceutically acceptable salt thereof, according to claim 1 and a pharmaceutically acceptable carrier material.