Phthalazinone derivatives
View Patent ↗Compounds of the formula (I): wherein A and B together represent an optionally substituted, fused aromatic ring; X can be NR X or CR X R Y ; if X═NR X then n is 1 or 2 and if X═CR X R Y then n is 1; R X is selected from the group consisting of H, optionally substituted C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, amido, thioamido, ester, acyl, and sulfonyl groups; R Y is selected from H, hydroxy, amino; or R X and R Y may together form a spiro-C 3-7 cycloalkyl or heterocyclyl group; R C1 and R C2 are both hydrogen, or when X is CR X R Y , R C1 , R C2 , R X and R Y , together with the carbon atoms to which they are attached, may form an optionally substituted fused aromatic ring; and R 1 is selected from H and halo.
1. A compound of the formula (Ib):
or an isomer or salt thereof, or a mixture of any thereof, wherein:
A and B together represent a fused aromatic ring, optionally substituted with one or more substituent groups selected from halo, nitro, hydroxyl, ether, thiol, thioether, amino, C 1-7 alkyl, C 3-20 heterocyclyl and C 5-20 aryl;
R x is selected from H, C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, amido, thioamido, ester, acyl, and sulfonyl groups, wherein the acyl, C 1-20 alkyl, C 5-20 aryl or C 3-20 heterocyclyl group is optionally substituted with one or more substituent groups selected from C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, halo, hydroxyl, ether, nitro, cyano, acyl, carboxy, ester, amido, amino, acylamido, ureido, acyloxy, thiol, thioether, sulfoxide, sulfonyl, thioamido and sulfonamido;
R C1 and R C2 are both hydrogen; and
R 1 is selected from H and halo.
2. The compound, or isomer or salt, or mixture thereof according to claim 1 , wherein the fused aromatic ring represented by A and B together is benzene.
3. The compound, or isomer or salt, or mixture thereof according to claim 1 , wherein R 1 is selected from H, Cl, and F.
4. The compound, or isomer or salt, or mixture thereof according to claim 1 , wherein R x is selected from H, C 1-20 alkyl, C 5-20 aryl, acyl, sulfonyl, amido, and thioamido groups, wherein the acyl, C 1-20 alkyl or C 5-20 aryl group is optionally substituted with one or more substituent groups selected from C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, halo, hydroxyl, ether, nitro, cyano, acyl, carboxy, ester, amido, amino, acylamido, ureido, acyloxy, thiol, thioether, sulfoxide, sulfonyl, thioamido and sulfonamido.
5. The compound, or isomer or salt, or mixture thereof according to claim 1 , which is of formula (II):
wherein:
R C3 is selected from C 1-7 alkyl, C 5-20 aryl, and C 3-20 heterocyclyl, wherein the C 1-7 alkyl, C 5-20 aryl or C 3-20 heterocyclyl group is optionally substituted with one or more substituent groups selected from C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, halo, hydroxyl, ether, nitro, cyano, acyl, carboxy, ester, amido, amino, acylamido, ureido, acyloxy, thiol, thioether, sulfoxide, sulfonyl, thioamido and sulfonamido.
6. The compound, or isomer or salt, or mixture thereof according to claim 1 , which is of formula (III):
wherein R is selected from:
7. A composition comprising two or more entities chosen from a compound of formula (IV),
and salts of a compound of formula (IV).
8. A pharmaceutical composition comprising a compound of formula (Ib):
or an isomer or salt thereof, or a mixture thereof, wherein:
A and B together represent a fused aromatic ring, optionally substituted with one or more substituent groups selected from halo, nitro, hydroxyl, ether, thiol, thioether, amino, C 1-7 alkyl, C 3-20 heterocyclyl and C 5-20 aryl;
R x is selected from H, C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, amido, thioamido, ester, acyl, and sulfonyl groups, wherein the acyl, C 1-20 alkyl, C 5-20 aryl or C 3-20 heterocyclyl group is optionally substituted with one or more substituent groups selected from C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, halo, hydroxyl, ether, nitro, cyano, acyl, carboxy, ester, amido, amino, acylamido, ureido, acyloxy, thiol, thioether, sulfoxide, sulfonyl, thioamido and sulfonamido;
R C1 and R C2 are both hydrogen; and
R 1 is selected from H and halo; and
one or more pharmaceutically acceptable entities chosen from carriers, excipients, buffers, adjuvants, and stabilizers.
9. The pharmaceutical composition of claim 8 , wherein the compound is of formula (II):
or an isomer or salt, or mixture thereof, wherein:
R C3 is selected from C 1-7 alkyl, C 5-20 aryl, and C 3-20 heterocyclyl, wherein the C 1-7 alkyl, C 5-20 aryl or C 3-20 heterocyclyl group is optionally substituted with one or more substituent groups selected from C 1-20 alkyl, C 5-20 aryl, C 3-20 heterocyclyl, halo, hydroxyl, ether, nitro, cyano, acyl, carboxy, ester, amido, amino, acylamido, ureido, acyloxy, thiol, thioether, sulfoxide, sulfonyl, thioamido and sulfonamido.