Chemical compounds
First Claim
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1. A compound of formula (I):
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wherein;
R1 is phenyl which is optionally substituted by halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, nitro or cyano;
R2, R3 and R4 are, independently, hydrogen or C1-4 alkyl;
R5 is C1-6 alkyl, aryl, heteroaryl, aryl(C1-4)alkyl, heteroaryl(C1-4)alkyl or C3-8 cycloalkyl;
wherein the aryl and heteroaryl moieties of R5 are optionally substituted by halogen, C1-6 alkyl (optionally substituted by halogen, C1-6 alkoxy or phenyl (itself optionally substituted by halogen, C1-4 alkyl, C1-4 alkoxy or CF3)), OR6, S(O)mR7, S(O)2NR8R9, NR10S(O)2R11, C(O)R12, C(O)NR13R14, NR15C(O)R16, NR17R18, NR19C(O)NR20R21, methylenedioxy, nitro or cyano;
X is (CH2)n, where n is 1, 2, 3 or 4;
Y is a 2,4-, 2,5- or 3,5-linking 5-membered heteroaryl ring having 2 or 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulphur, wherein Y is optionally substituted by C1-4 alkyl;
R6, R8, R9, R10, R13, R14, R15, R16, R17, R18, R19, R20 and R21 are independently, hydrogen or C1-6 alkyl (optionally substituted by C1-6 alkoxy (provided no acetal or aminal is formed) or phenyl (itself optionally substituted by halogen, C1-4 alkyl, C1-4 alkoxy or CF3));
R7 and R11 are, independently, C1-6 alkyl (optionally substituted by C1-6 alkoxy (provided no thioacetal is formed) or phenyl (itself optionally substituted by halogen, C1-4 alkyl, —
C1-4 alkoxy or CF3));
R12 is hydrogen, C1-6 alkyl (optionally substituted by C1-6 alkoxy (provided no acetal is formed) or phenyl (itself optionally substituted by halogen, C1-4 alkyl, C1-4 alkoxy or CF3)) or C1-6 alkoxy (unsubstituted or mono-substituted by C1-6 alkoxy or phenyl (itself optionally substituted by halogen, C1-4 alkyl, C1-4 alkoxy or CF3));
or a pharmaceutically acceptable salt thereof.
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Abstract
The invention provides a compound of formula (I): wherein R1, R2, R3, R4, R5, N, X and Y are as defined in the specification, processes, for their preparation, pharmaceutical compositions containing them, and their use in therapy, especially for the treatment of chemokine receptor related diseases and conditions.
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Citations
8 Claims
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1. A compound of formula (I):
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wherein; R1 is phenyl which is optionally substituted by halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, nitro or cyano;
R2, R3 and R4 are, independently, hydrogen or C1-4 alkyl;
R5 is C1-6 alkyl, aryl, heteroaryl, aryl(C1-4)alkyl, heteroaryl(C1-4)alkyl or C3-8 cycloalkyl;
wherein the aryl and heteroaryl moieties of R5 are optionally substituted by halogen, C1-6 alkyl (optionally substituted by halogen, C1-6 alkoxy or phenyl (itself optionally substituted by halogen, C1-4 alkyl, C1-4 alkoxy or CF3)), OR6, S(O)mR7, S(O)2NR8R9, NR10S(O)2R11, C(O)R12, C(O)NR13R14, NR15C(O)R16, NR17R18, NR19C(O)NR20R21, methylenedioxy, nitro or cyano;
X is (CH2)n, where n is 1, 2, 3 or 4;
Y is a 2,4-, 2,5- or 3,5-linking 5-membered heteroaryl ring having 2 or 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulphur, wherein Y is optionally substituted by C1-4 alkyl;
R6, R8, R9, R10, R13, R14, R15, R16, R17, R18, R19, R20 and R21 are independently, hydrogen or C1-6 alkyl (optionally substituted by C1-6 alkoxy (provided no acetal or aminal is formed) or phenyl (itself optionally substituted by halogen, C1-4 alkyl, C1-4 alkoxy or CF3));
R7 and R11 are, independently, C1-6 alkyl (optionally substituted by C1-6 alkoxy (provided no thioacetal is formed) or phenyl (itself optionally substituted by halogen, C1-4 alkyl, —
C1-4 alkoxy or CF3));
R12 is hydrogen, C1-6 alkyl (optionally substituted by C1-6 alkoxy (provided no acetal is formed) or phenyl (itself optionally substituted by halogen, C1-4 alkyl, C1-4 alkoxy or CF3)) or C1-6 alkoxy (unsubstituted or mono-substituted by C1-6 alkoxy or phenyl (itself optionally substituted by halogen, C1-4 alkyl, C1-4 alkoxy or CF3));
or a pharmaceutically acceptable salt thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8)
with a compound of formula (III);
in a suitable solvent, in the presence of a suitable coupling agent and at a temperature in the range 0-50°
C.;
or,B. where R2 is hydrogen, reacting a compound of formula (IV);
with an aldehyde of formula R1CHO in a suitable solvent and in the presence of a suitable acid; and
reducing the product so formed;
or,C. where Y is 1,3,4-oxadiazolyl and R4 is hydrogen, heating a compound of formula (V);
at a suitable temperature, in a suitable solvent and in the presence of a suitable ring-closure chemical.
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Specification