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US 6,586,439 B2Granted
Pharmaceutically active compounds
AssigneePfizer Inc.
InventorsGraham Nigel Maw, David James Rawson
Life of this patent
Estimating the term…
Abstract
There is provided compounds of formula IA and of formula IB, wherein R1, R2, R3, Het1 and X have meanings given in the description, which are useful in the curative and prophylactic treatment of medical conditions for which inhibition of a cyclic guanosine 3′,5′-monophosphate phosphodiesterase (e.g. cGMP PDE5) is desired.
Claims19
A compound of formula IB,
- wherein
- X represents N;
- R1 represents H, —CN, —C(O)N(R4)R5, —C(O)R4, —C(O)OR4, —N(R4)R6, —OR7, aryl, Het2 or lower alkyl optionally interrupted by one or more of —O—, —S— or —N(R4)— and/or substituted and/or terminated by one or more substituents selected from the group consisting of halo, —CN, —NO2, lower alkyl, —C(O)N(R4)R5, —C(O)R4, —C(O)OR4, —N(R4)R6, —OR7, —S(O)nR4, —S(O)nN(R4)R5, aryl 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, lower alkyl optionally substituted and/or terminated by one or more substituents selected from the group consisting of lower alkyl, aryl, 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 aryl;
- R2 represents H, aryl, Het4 or lower alkyl optionally substituted by one or more substituents selected from the group consisting of lower alkyl optionally substituted by one or more substituents selected from —OH or halo, aryl, 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, aryl, lower alkyl optionally substituted by one or more substituents selected from the group consisting of aryl and halo, —C(O)R9j, —C(O)N(R9k)R9m or —S(O)2R10b;
- R9a to R9m independently represent, at each occurrence, H, aryl or lower alkyl optionally substituted by one or more substituents selected from the group consisting of aryl and halo;
- R10a and R10b represent, at each occurrence, aryl or lower alkyl optionally substituted by one or more substituents selected from the group consisting of aryl 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 aryl group is optionally substituted with one or more substituents selected from the group consisting of halo, lower alkyl optionally substituted by one or more substituents selected from —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 or —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 lower alkyl optionally substituted by one or more substituents selected from lower alkyl, aryl, 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 or —N(R11)R9i), aryl, 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;
- and
- n represents, at each occurrence, 0, 1 or 2;
- or a pharmaceutically or veterinarily acceptable salt, solvate or prodrug thereof.
16 more elements
Dependencies are inferred from the claim text.