Pharmaceutically active compounds
First Claim
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1. A compound of formula I, whereinR1 and R2 independently represent phenyl (optionally substituted by one or more substituents selected from halo, —
- CN, —
CF3, —
OCF3, C1-4 alkoxy or C1-4 alkyl (which latter two groups are optionally substituted by C1-4 haloalkyl or C1-4 haloalkoxy)) or C1-6 alkyl optionally interrupted by —
O—
, —
S— and
/or —
N(R4)— and
/or optionally substituted and/or terminated by Het2, a N-linked heterocyclic group (selected from piperidinyl and morpholinyl) or phenyl (which latter group is optionally substituted by one or more substituents selected from halo, —
CN, —
CF3, —
OCF3, C1-4 alkoxy or C1-4 alkyl (which latter two groups are optionally substituted by C1-4 haloalkyl or C1-4 haloalkoxy));
R4 represents H or C1-4 alkyl;
R3 represents OR5 or N(R6)R7;
R5 represents C3-6 cycloalkyl, —
(C1-4 alkylene)-1-piperidinyl, tetrahydrofuranyl, tetrahydropyranyl or C1-6 alkyl, which latter group is optionally substituted and/or terminated by one or two substituents selected from C3-5 cycloalkyl, —
OR8, —
N(R6)R7, phenyl, furanyl and pyridinyl, and which C1-6 alkyl group is optionally terminated by a C1-4 haloalkyl group;
R6 and R7 independently represent, at each occurrence, H, C1-4 alkyl (optionally substituted by C3-5 cycloalkyl or C1-4 alkoxy), or R6 and R7, together with the nitrogen atom to which they are attached, form an azetidinyl, pyrrolidinyl, piperidinyl or morpholinyl group;
R8 represents H, C1-4 alkyl (which C1-4 alkyl group is optionally terminated by a C1-4 haloalkyl group) or benzyl;
Het1 represents a 4-R9-1-piperazinyl group optionally substituted with one or two C1-4 alkyl groups and optionally in the form of its 4-N-oxide;
R9 represents H, pyridinyl, pyrimidinyl, C3-6 alkenyl or C1-4 alkyl optionally substituted by one or two substituents selected from —
OH, —
N(R6)R7, —
C(O)N(R6)R7, benzodioxolyl, benzodioxanyl or phenyl (which latter group is optionally substituted by C1-4 alkoxy);
Het2 represents a C-linked 6-membered heterocyclic group containing one or two nitrogen atoms, optionally in the form of its mono-N-oxide, or a C-linked 5-membered heterocyclic group containing two or three nitrogen atoms, wherein either of said heterocyclic groups is optionally substituted with C1-4 alkyl, C1-4 alkoxy or N(H)R10; and
R10 represents H, C1-4 alkyl or C1-4 alkanoyl;
or a pharmaceutically, or a veterinarily, acceptable derivative thereof.
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Abstract
There is provided compounds of formula I,
wherein R1, R2, R3 and Het1 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.
79 Citations
16 Claims
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1. A compound of formula I,
wherein R1 and R2 independently represent phenyl (optionally substituted by one or more substituents selected from halo, — - CN, —
CF3, —
OCF3, C1-4 alkoxy or C1-4 alkyl (which latter two groups are optionally substituted by C1-4 haloalkyl or C1-4 haloalkoxy)) or C1-6 alkyl optionally interrupted by —
O—
, —
S— and
/or —
N(R4)— and
/or optionally substituted and/or terminated by Het2, a N-linked heterocyclic group (selected from piperidinyl and morpholinyl) or phenyl (which latter group is optionally substituted by one or more substituents selected from halo, —
CN, —
CF3, —
OCF3, C1-4 alkoxy or C1-4 alkyl (which latter two groups are optionally substituted by C1-4 haloalkyl or C1-4 haloalkoxy));
R4 represents H or C1-4 alkyl;
R3 represents OR5 or N(R6)R7;
R5 represents C3-6 cycloalkyl, —
(C1-4 alkylene)-1-piperidinyl, tetrahydrofuranyl, tetrahydropyranyl or C1-6 alkyl, which latter group is optionally substituted and/or terminated by one or two substituents selected from C3-5 cycloalkyl, —
OR8, —
N(R6)R7, phenyl, furanyl and pyridinyl, and which C1-6 alkyl group is optionally terminated by a C1-4 haloalkyl group;
R6 and R7 independently represent, at each occurrence, H, C1-4 alkyl (optionally substituted by C3-5 cycloalkyl or C1-4 alkoxy), or R6 and R7, together with the nitrogen atom to which they are attached, form an azetidinyl, pyrrolidinyl, piperidinyl or morpholinyl group;
R8 represents H, C1-4 alkyl (which C1-4 alkyl group is optionally terminated by a C1-4 haloalkyl group) or benzyl;
Het1 represents a 4-R9-1-piperazinyl group optionally substituted with one or two C1-4 alkyl groups and optionally in the form of its 4-N-oxide;
R9 represents H, pyridinyl, pyrimidinyl, C3-6 alkenyl or C1-4 alkyl optionally substituted by one or two substituents selected from —
OH, —
N(R6)R7, —
C(O)N(R6)R7, benzodioxolyl, benzodioxanyl or phenyl (which latter group is optionally substituted by C1-4 alkoxy);
Het2 represents a C-linked 6-membered heterocyclic group containing one or two nitrogen atoms, optionally in the form of its mono-N-oxide, or a C-linked 5-membered heterocyclic group containing two or three nitrogen atoms, wherein either of said heterocyclic groups is optionally substituted with C1-4 alkyl, C1-4 alkoxy or N(H)R10; and
R10 represents H, C1-4 alkyl or C1-4 alkanoyl;
or a pharmaceutically, or a veterinarily, acceptable derivative thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)
(a) reaction of a compound of formula II, wherein L1 represents a leaving group, and R1, R2 and R3 are as defined in claim 1, with a compound of formula III,
- CN, —
-
14. A compound of formula II, as defined in claim 13.
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15. A compound of formula XXI, as defined in claim 13.
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16. A method as claimed in claim 11, wherein the condition is male erectile dysfunction (MED).
Specification