Prodrug forms of ribonucleotide reductase inhibitors 3-ap...

Details Prodrug forms of ribonucleotide reductase inhibitors 3-ap... Prodrug forms of ribonucleotide reductase inhibitors 3-ap...

C - Chemistry, Metallurgy

07

D

C07D 213/75 (2006.01) A61K 31/44 (2006.01) A61P 35/00 (2006.01)

Patent

CA 2290617

The present invention relates to novel prodrug forms of ribonucleoside diphosphate reductase inhibitors 3-aminopyri-dine-2-carboxaldehyde thiosemicarbazone (3-AP) and 3-amino-4- methylpyridine-2-carboxaldehyde thiosemicarbazone (3-AMP) which have increased water solubility, bioavailability and resistance to in vivo acetylation of their amino functions. Novel compounds according to the present invention relate to those of formula (1), where R4 is H or CH3 and R5 is CHR, benzyl or ortho or para substituted benzyl; R is H, CH3, CH2CH3, CH2CH2CH3 or (a); R' is a free acid phosphate, phosphate salt or an -S-S-R" group; R" is CH2CH2NHR6, CH2CH2OH, CH2COOR7, an ortho or para substituted alkylphenyl and ortho or para substituted nitro-phenyl; R6 is H, C1-C4 acyl group, trifluoroacetyl, benzoyl or substituted benzoyl group, and R7 is H, C1-C4 alkyl or a benzyl or substituted benzyl.

La présente invention concerne de nouvelles formes précurseurs de médicaments d'inhibiteurs 3-aminopyridine-2-carboxaldéhyde thiosemicarbazone (3-AP) et 3-amino-4-méthylpyridine-2-carboxaldéhyde thiosemicarbazone (3-AMP) de la réductase ribonucléoside-diphosphate présentant une solubilité dans l'eau et une biodisponibilité accrues et une meilleure résistance à l'acétylation in vivo de leurs fonctions amine. Les nouveaux composés de la présente invention sont représentés par la formule (1), dans laquelle R<4> est H ou CH3, R<5> est CHR, un benzyle ou un benzyle ortho ou para substitué; R est H, CH3, CH2CH3, CH2CH2CH3, ou (a); R' est un phosphate acide libre, un sel de phosphate ou un groupe -S-S-R''; R'' est CH2CH2NHR<6>, CH2CH2OH, CH2COOR<7>, un alkyphényle ortho ou para substitué et un nitrophényle ortho ou para substitué; R<6> est H, un groupe acyle en C1-C4, un trifluoroacétyle, un groupe benzoyle ou un groupe benzoyle substitué, et R<7> est H, un alkyle en C1-C4 ou un benzyle ou un benzyle substitué.

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