Pharmaceutically active compounds

A compound of formula IB,

• wherein
• X represents CH;
• R1 represents H, —CN, —C(O)N(R4)R5, —C(O)R4, —C(O)OR4, —N(R4)R6, —OR7, a six- to ten-membered carbocyclic aromatic group, Het2 or C1-12 alkyl optionally interrupted by one or more of —O—, —S— or —N(R4)— and/or substituted by one or more substituents selected from the group consisting of halo, —CN, —NO2, C1-12alkyl, —C(O)N(R4)R5, —C(O)R4, —C(O)OR4, —N(R4)R6, —OR7, —S(O)nR4, —S(O)nN(R4R5, a six- to ten-membered carbocyclic aromatic group, and Het2;
• R6 represents R5, —S(O)2R8, —S(O)2N(R4)R5, —C(O)R4, —C(O)OR8 or —C(O)N(R4)R5;
• R7 represents R4 or —C(O)R4;
• R3, R4, R5 and R8 independently represent, at each occurrence, C1-12alkyl optionally substituted by one or more substituents selected from the group consisting of C1-12 alkyl, a six- to ten-membered carbocyclic aromatic groups Het3, halo, —CN, —NO2, —OR9a, —C(O)R9b, —C(O)OR9c, —C(O)N(R9d)R9e, —S(O)2R10a, —S(O)2N(R9f)R9g, —OC(O)R9h and —N(R11)R9i;
• R3, R4 and R5 may also, at each occurrence, independently represent H;
• R4, R5 and R8 may also, at each occurrence, independently represent a six- to ten-membered carbocyclic aromatic group;
• R2 represents H, a six- to ten-membered carbocyclic aromatic group, Het4 or C1-12 alkyl optionally substituted by one or more substituents selected from the group consisting of C1-12 alkyl optionally substituted by one or more substituents selected from —OH and halo, a six- to ten-membered carbocyclic aromatic group, Het5, halo, —CN, —NO2, —OR9a, —C(O)R9b, —C(O)OR9c, —C(O)N(R9d)R9e, —S(O)2R10a, —S(O)2N(R9f)R9g, —OC(O)R9h and —N(R11)R9i;
• R11 represents, at each occurrence, H, a six- to ten-membered carbocyclic aromatic group, C1-12 alkyl optionally substituted by one or more substituents selected from the group consisting of a six- to ten-membered carbocyclic aromatic group and halo, —C(O)R9j, —C(O)N(R9k)R9m or —S(O)2R10b;
• R9a to R9m independently represent, at each occurrence, H, a six- to ten-membered carbocyclic aromatic group or C1-12 alkyl optionally substituted by one or more substituents selected from the group consisting of a six- to ten-membered carbocyclic aromatic group and halo;
• R10a and R10b represent, at each occurrence, a six- to ten-membered carbocyclic aromatic group or C1-12alkyl optionally substituted by one or more substituents selected from the group consisting of a six- to ten-membered carbocyclic aromatic group and halo;
• Het1 represents an optionally substituted four- to twelve-membered heterocyclic group, which group contains at least one nitrogen atom by which the Het1 group is attached to the compound and, optionally, one or more further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
• Het2 to Het5 independently represent optionally substituted four- to twelve-membered heterocyclic groups, which groups contain one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
• each a six- to ten-membered carbocyclic aromatic group is optionally substituted with one or more substituents selected from the group consisting of halo, C1-12alkyl optionally substituted by one or more substituents selected from the group consisting of —CN, —NO2, —OR9a, —C(O)R9b, —C(O)OR9c, —C(O)N(R9d)R9e, —S(O)2N(R9f)R9g, —S(O)nR10a, —OC(O)R9h and —N(R11)R9i), —CN, —NO2, —OR9a, —C(O)R9b, —C(O)OR9c, —C(O)N(R9d)R9e, —S(O)nR10a, —S(O)2N(R9f)R9g, OC(O)R9h and —N(R11)R9i;
• Het1, Het2, Het3, Het4 and Het5 are each optionally substituted with one or more substituents selected from the group consisting of C1-12 alkyl optionally substituted by one or more substituents selected from the group consisting of C1-12 alkyl, a six- to ten-membered carbocyclic aromatic group, Het2, halo, —CN, —NO2, —OR9a, —C(O)R9b, —C(O)OR9c, —C(O)N(R9d)R9e, —S(O)nR10a, —S(O)2N(R9f)R9g, —OC(O) R9h, —N(R11)R9i), a six- to ten-membered carbocyclic aromatic group, Het2, halo, —CN, —NO2, —OR9a, —C(O)R9b, —C(O)OR9c, —C(O)N(R9d)R9e, —S(O)nR10a, —S(O)2N(R9f)R9g, —OC(O)R9h and —N(R11)R9i,
• n represents, at each occurrence, 0, 1 or 2;
• or a pharmaceutically or veterinarily acceptable salt, solvate or pro-drug thereof;
• provided that when
• R1 represents H;
• R3 represents C1-8 alkyl;
• and Het1 represents a 5- or 6-membered saturated heterocyclic ring, which ring is optionally substituted via a free ring N-atom by C1-6 alkyl optionally substituted by —OH;
• then R2 does not represent:
• (a) C3-11 alkyl substituted by one of the following:
• (i) in the C1-11 position (relative to the purinone N-atom), by C1-11 alkyl or —C(O)R9b, wherein R9b represents H or C1-4 alkyl;
• (ii) in the C-2 position (relative to the purinone N-atom) by one group selected from the group consisting of —OR9a, wherein R9a represents H, C1-6 alkyl or benzyl, —OC(O)R9h, wherein R9h represents H, C1-6 alkyl or phenyl, and —N(R11)R9i, wherein R9i represents H or C1-6 alkyl and R11 represents H, C1-6 alkyl, —C(O)R9i, where R9i represents H, C1-4 alkyl or phenyl, or —S(O)2R10b where R10b represents C1-4 alkyl or phenyl, and optionally, at the same C-2 position, by a further C1-4 alkyl group;
• and which C3-11 alkyl group is optionally substituted:
• (I) in the C-2 to C-11 positions (relative to the purinone N-atom), by phenyl optionally substituted by halo, —CN, —NO2, C1-6 alkyl or —S(O)2N(R9f)R9g, in which latter groups R9f and R9g independently represent H, phenyl or C1-12alkyl;
• and/or
• (II) in the C-1 position (relative to the purinone N-atom), by C1-3 alkyl;
• (b) C3-9 alkyl substituted in the C-2 to C-9 positions (relative to the purinone N-atom) by —N(R11)R9i wherein R11 and R9i each independently represent H or C1-5 alkyl optionally substituted by phenyl, which latter group is substituted by —S(O)2N(R9f)R9g in which R9f and R9g independently represent H, phenyl or C1-12 alkyl and optionally substituted in the C-1 position (relative to the purinone N-atom) by:
• (i) C1-5 alkyl optionally substituted by —OH;
• and/or
• (ii) C1-3 alkyl;
• or
• (c) C1-4 alkyl or C10-16 n-alkyl;
• wherein, in the above proviso, unless otherwise indicated, alkyl, phenyl and benzyl groups are unsubstituted.