Abstract
Compounds of the formula: (I) or solvate thereof, wherein: R2 is an optionally substituted C5-20 aryl group; R6 and R9 are independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR', nitro, Me3Sn and halo; where R and R' are independently selected from optionally substituted C1-12 alkyl, C3-20 heterocyclyl and C5-20 aryl groups; R7 is selected from H, R, OH, OR, SH, SR, NH2, NHR, NHRR', nitro, Me3Sn and halo; R'' is a C3-12 alkylene group, which chain may be interrupted by one or more heteroatoms and/or aromatic rings; X is selected from O, S, or NH; z is 2 or 3; M is a monovalent pharmaceutically acceptable cation; R2', R6', R7', R9', X' and M' are selected from the same groups as R2, R6, R7, R9, X and M respectively, or M and M' may together represent a divalent pharmaceutically acceptable cation.
Claims
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A compound of the formula I:
wherein:
R2 is an optionally substituted aryl or heteroaryl group having 5 to 20 ring atoms, the heteroaryl groups having one or more heteroatoms independently selected from the group consisting of N, O and S, wherein the optional substituents are independently selected from C1-C12 alkyl, heterocyclyl groups having 3 to 20 ring atoms of which 1 to 10 are heteroatoms independently selected from the group consisting of N, O and S, aryl groups having 5 to 20 ring atoms, halo, hydroxy, alkoxy, acetal, hemiacetal, ketal, hemiketal, oxo, thione, imino, formyl, acyl, carboxy, thiocarboxy, thiolcarboxy, imidic acid, hydroxamic acid, ester, acyloxy, oxycaroyloxy, amino, amido, thioamido, acylamido, aminocaronyloxy, ureido, guanidino, tetrazolyl, imino, amidino, nitro, nitroso, azido, cyano, isocyano, cyanato, isocyanato, thiocyano, isothiocyano, sulfhydryl, thioether, disulfide, sulfine, sulfone, sulfinic acid, sulfonic acid, sulfinate, sulfonate, sulfinyloxy, sulfonyloxy, sulfate, sulfamyl, sulfonamido, sulfamino, sulfinamino, phosphino, phospho, phosphinyl, phosphonic acid, phosphonate, phosphoric acid, phosphate, phosphorous acid, phosphite, phosphoramidite, phosphoramidate or bisoxyalkylene;
R6 and R9 are independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR′, nitro, Me3Sn and halo;
where R and R′ are independently selected from optionally substituted C1-12 alkyl, heterocyclyl groups having 3 to 20 ring atoms of which 1 to 10 are heteroatoms independently selected from the group consisting of N, O and S and aryl groups having 5 to 20 ring atoms wherein the optional substituents are independently selected from C1-C12 alkyl, heterocyclyl groups having 3 to 20 ring atoms of which 1 to 10 are heteroatoms independently selected from the group consisting of N, O and S, aryl groups having 5 to 20 ring atoms, halo, hydroxy, alkoxy, acetal, hemiacetal, ketal, hemiketal, oxo, thione, imino, formyl, acyl, carboxy, thiocarboxy, thiolcarboxy, imidic acid, hydroxamic acid, ester, acyloxy, oxycaroyloxy, amino, amido, thioamido, acylamido, aminocaronyloxy, ureido, guanidino, tetrazolyl, imino, amidino, nitro, nitroso, azido, cyano, isocyano, cyanato, isocyanato, thiocyano, isothiocyano, sulfhydryl, thioether, disulfide, sulfine, sulfone, sulfinic acid, sulfonic acid, sulfinate, sulfonate, sulfinyloxy, sulfonyloxy, sulfate, sulfamyl, sulfonamido, sulfamino, sulfinamino, phosphino, phospho, phosphinyl, phosphonic acid, phosphonate, phosphoric acid, phosphate, phosphorous acid, phosphite, phosphoramidite, phosphoramidate or bisoxyalkylene;
R7 is selected from H, R, OH, OR, SH, SR, NH2, NHR, NHRR′, nitro, Me3Sn and halo;
R″ is a C3-12 alkylene group, which chain may be interrupted by one or more heteroatoms and/or aromatic rings;
X is selected from O, S, or NH;
z is 2 or 3;
M is a monovalent pharmaceutically acceptable cation;
R2′, R6′, R7′, R9′, X′ and M′ are selected from the same groups as R2, R6, R7, R9, X and M respectively, or M and M′ may together represent a divalent pharmaceutically acceptable cation.
- A compound according to claim 1, wherein X is O.
- A compound according to claim 1, wherein R″ represents a linear saturated C3-12 alkylene group.
- A compound according to claim 1, wherein R9 is H.
- A compound according to claim 1, wherein R6 is H.
- A compound according to claim 1, wherein R7 is selected from H, OH and OR, where R is selected from optionally substituted C1-7 alkyl, heterocyclyl groups having 3 to 10 ring atoms of which 1 to 5 are heteroatoms independently selected from the group consisting of N, O and S, or aryl groups having 5 to 10 ring atoms.
- A compound according to claim 6, wherein R7 is OMe or OCH2Ph.
- A compound according to claim 1, wherein R2 is an optionally substituted aryl group having 5 to 7 ring atoms.
- A compound according to claim 8, wherein R2 is an optionally substituted phenyl group.
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A compound according to claim 1, wherein R2 is the same as R2′;
R6 is the same as R6′;
R7 is the same as R7′;
R9 is the same as R9′;
M is the same as M′; and
X is the same as X′.
- A compound according to claim 1, wherein M and M40 are monovalent pharmaceutically acceptable cations.
- A compound according to claim 11, wherein M and M′ are Na+.
- A compound according to claim 1 wherein z is 3.
- A pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutical excipient.
- A compound according to claim 1, wherein the optional substituents on R2 are independently selected from C1-C12 alkyl, aryl groups having 5 to 20 ring atoms, halo, hydroxy, alkoxy, formyl, amino, acylamido, nitro, cyano, sulfhydryl, thioether or bisoxyalkylene.
- A compound according to claim 15, wherein the optional substituents on R2 are independently selected from halo, C1-C7 alkoxy, C1-C7 alkyl or bis-oxy-alkylene.
- A compound according to claim 1, wherein R and R′ are unsubstituted.
Owners (US)
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Medimmune Limited
(Oct 13 2014)
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Spirogen Sarl
(Nov 05 2012)
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Spirogen Limited
(Sep 13 2006)
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Applicants
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Spirogen Ltd
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Inventors
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Gregson Stephen John
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Howard Philip Wilson
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Chen Zhizhi
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IPC Classifications
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C07D519/00
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A61K31/5517
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A61P35/00
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Document Preview
- Publication: Nov 3, 2009
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Application:
Apr 21, 2006
US 91189006 A
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Priority:
Apr 21, 2006
GB 2006001456 W
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Priority:
Nov 7, 2005
GB 0522746 A
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Priority:
Apr 21, 2005
GB 0508084 A