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US 8,044,067 B2Granted
Isoquinolines as IGF-1R inhibitors
AssigneeAnalytecon SA
InventorsJan Gunzinger, Kurt Leander
Life of this patent
Estimating the term…
Abstract
Compounds of the formula (I): were synthesized. In at least one embodiment, they were found to down-regulate or inhibit the expression or function of the IGF-1 receptor.
Claims24
A compound of the following formula (I):
- wherein,
- R1 designates hydrogen;
- OH;
- CN;
- trifluoromethyl;
- NH2;
- NHCN;
- NHCOCH3;
- NHCOCH2CH3;
- NHCHO;
- NHCOOCH3;
- amino(C1-C6)alkyl;
- amino(C1-C3)dialkyl;
- (C1-C6)alkoxy;
- (C1-C6)alkyl;
- carbonyl-R9 wherein R9 designates hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy;
- (C1-C6) alkyl-R10;
- (C1-C6)alkoxy-R10;
- amino(C1-C6)alkyl-R10 and amino(C1-C3)dialkyl-R10 whereby R10 designates at least one OMe, OEt, OPr, OIsopropyl, OH, CN, NH2, ester groups with (C1-C3)alkyl, carbonate groups with (C1-C3)alkyl;
- R2 designates (when R3, R4 forms a carbonyl group) hydrogen;
- (C1-C6)alkyl;
- CH2CH2N(CH3)2;
- NH2;
- NHCH3;
- N(CH3)2;
- NHCN;
- NHCOCH3;
- NHCOCH2CH3;
- NHCHO;
- NHCOOCH3;
- R2 designates (when R3═R4═H) hydrogen;
- (C1-C6)alkyl;
- CN;
- CHO;
- COOCH3;
- COOCH2CH3;
- COCH3;
- R3 and R4 designate hydrogen, or R3 and R4 taken together form a carbonyl group;
- R6 designates hydrogen, or R6 and R7 taken together form a methylenedioxy group or an ethylenedioxy group;
- R7 designates Me;
- (C1-C4)alkoxy;
- (C1-C2)alkoxy partly or fully fluorinated, OCF3;
- trifluoromethyl;
- SMe;
- SEt or R7 and R8 taken together form a methylenedioxy group or an ethylenedioxy group;
- R8 designates hydrogen;
- (C1-C4)alkyl;
- OH;
- (C1-C4)alkoxy;
- (C1-C2)alkoxy partly or fully fluorinated;
- OCF3;
- trifluoromethyl;
- halogen or OX;
- R3′ and R5′ each independently designate OH;
- Me;
- Et;
- OMe;
- OMe partly or fully fluorinated;
- OCF3;
- trifluoromethyl or halogen;
- U designates N or CR2′, whereby R2′ denotes hydrogen, (C1-C4)alkyl;
- (C1-C4)alkoxy;
- trifluoromethyl or halogen;
- V designates N or CR4′, whereby R4′ denotes hydrogen;
- (C1-C6)alkoxy;
- (C1-C4)alkoxy partly or fully fluorinated;
- (C1-C6)alkyl;
- OH;
- trifluoromethyl;
- halogen or OX;
- W designates N or CR6′, whereby R6′ denotes hydrogen;
- (C1-C4)alkyl;
- (C1-C4)alkoxy;
- trifluoromethyl or halogen;
- wherein OX designates a group capable of conferring a prodrug property, said group being selected among phosphate derivatives, ester derivatives, carbonate derivatives and/or linked poly(ethylene glycols) derivatives;
- or pharmaceutically acceptable salt thereof,
- provided that when:
- R1 is H, R2 and R7 are Me, R8 and R4′ are H, R5′ must be different from F or Cl;
- or
- R1, R2 and R7 are Me, R8 and R4′ are H, R5′ must be different from F;
- or
- R1 is H, R2 and R7 are Me, R8 is H and R4′ is F, R5′ must be different from F.
79 more elements
Dependencies are inferred from the claim text.