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US 8,980,932 B2Granted
Cancer targeting using carbonic anhydrase isoform IX inhibitors
AssigneesStichting Maastricht Radiation Oncology “Maastro-Clinic”, Universite Montpellier 2 Sciences Et Techniques, Claudiu Supuran
InventorsPhilippe Lambin, Jean-Yves Winum, Claudiu Supuran
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Abstract
The present invention concerns novel carbonic anhydrase IX inhibitors comprising a nitroimidazole moiety and their use in therapy of hypoxic conditions, in particular cancer treatment, especially chemotherapy and radiotherapy. The compounds of the invention have an increased specificity for the carbonic anhydrase IX enzyme compared to the art. The present invention relates to novel nitroimidazole derivates represented by formula (1).
Claims13
A compound of formula (1),
- wherein Z is Z1 with formula (2a):
- or Z is Z2 with formula (2b):
- (CH2)nCH2X, where X=sulfamate or sulfamide;
- or
- or Z2 is of the formula:
- (CH2)nCH2—SO2NH2;
- or Z is Z3 with formula (2c):
- wherein R1 and R2 are, each independently, H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, cyano or halogen atom;
- R3, R4, R6 and R7 are, each independently H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, halogen atom, cyano, alkoxy, sulfonamide, sulfamate or sulfamide;
- R5 is sulfonamide, sulfamate or sulfamide;
- Y=O or S;
- and
- n=0, 1, 2, 3, 4 or 5 and where if n=0, R2=2-CH3, Z=Z1, R3=R4=R6=R7=H and R5=SO2NH2, then the NO2 is not on position 4,
- or a pharmaceutically acceptable salt thereof.
11 more elements
A compound of formula (1),
- wherein the compound is a compound of formula (3a)
- a compound of formula (3b)
- wherein X=sulfamate or sulfamide;
- or X is —SO2NH2;
- or a compound of formula (3c)
- wherein R1 and R2 are, each independently, H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, cyano or halogen atom;
- R3, R4, R6 and R7 are, each independently H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, halogen atom, cyano, alkoxy, sulfonamide, sulfamate or sulfamide;
- R5 is sulfonamide, sulfamate or sulfamide;
- Y=O or S;
- and
- n=0, 1, 2, 3, 4 or 5, or a pharmaceutically acceptable salt thereof.
8 more elements
Dependencies are inferred from the claim text.