Patent EA-004925-B1 (EA)
Title: 2-(1h-indol-3-yl)-2-oxo-acetamides with antitumor activity
Inventor: MENTA ERNESTO
IPC: C07D409/12
Filed: 2000-12-21
Abstract: 1. Compounds of formula I wherein: R1, R2 and R5 are independently hydrogen or a C1-C6 alkyl group; R3 is hydrogen, C1-C4 alkyl, aralkyl, optionally substituted phenyl; R4 is hydrogen, straight or branched C1-C8 alkyl, C5-C6 cycloalkyl; aralkyl; heteroaralkyl; X is one or more groups, at most four, independently selected from hydrogen; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 hydroxyalkyl; C1-C6-aminoalkyl; C1-C6-alkoxy-C1-C6-alkyl; C1-C18-acyloxy-C1-C6-alkyl; hydroxy; C1-C4 alkoxy; C1-C3 haloalkoxy; phenoxy; aralkoxy; C1-C3 acyloxy; amino; C1-C3 alkylamino; C1-C3-acylamino; C1-C3-alkylsulfonylamino; aroylamino; halogen; nitro; cyano; trifluoromethyl; carboxy; C1-C6 alkoxycarbonyl; a RaRbN(CH2)nC(-O)- group wherein Ra and Rb are independently hydrogen, C1-C3-alkyl or Ra and Rb together with the nitrogen atom they are linked to form a pyrrolidino, piperidino, piperazino or morpholino ring and n=0 or an integer from 1 to 4; a RaRcN(CH2)nC(-O)- group wherein Ra and n are as above defined and Rc is a C1-C4-alkoxycarbonyl group; a R1C(-O)- group wherein R1 is as above defined; sulfonyl; mercapto; C1-C4-alkylthio; C1-C4-alkylsulfinyl; C1-C4-alkylsulfonyl; aminosulfonyl; C1-C3-alkylaminosulfonyl; a group -P(-O)(OR1)(OR2) being R1 and R2 as above defined; a group (E)- or (Z)-C(R1)-C(R2)-C(-O)R6 wherein R6 is hydroxy, C1-C6-alkoxy, NRaRb or a group of formula RaRbN(CH2)mNR1-, being m an integer from 2 to 4 and R1, R2, Ra, and Rb as above defined; Y is an oxygen or sulfur atom, the isomers, enantiomers and mixtures thereof, and the pharmaceutically acceptable salts thereof. 2. Compounds as claimed in claim 1 wherein Y is an oxygen atom. 3. Compounds as claimed in claim 1 wherein Y is a sulfur atom. 4. Compounds as claimed in claim 1, 2 or 3 wherein R1, R2 and R3 are hydrogen or methyl. 5. Compounds as claimed in any one of claims 1 to 4 wherein R4 is hydrogen; methyl; benzyl substituted on the benzene ring with one or more groups selected from methyl, t-butyl, fluorine, chlorine, bromine, hydroxy, acetoxy, methoxy, trifluoromethoxy, benzyloxy, trifluoromethyl, cyano, nitro, amino, acetylamino, methylsulfonylamino, methylmercapto, methylsulfinyl, methylsulfonyl, phenyl, ethoxycarbonyl, carboxy, carboxymethyl, (ethoxycarbonyl)methyl, (tert-butoxycarbonyl)methyl, (benzyloxycarbonyl)methyl, (dimethylcarbamoyl)methyl; [alpha]-naphthyl, [beta]-naphthyl; 4-pyridyl; 4-pyridyl-N oxide. 6. Compounds as claimed in any one of the above claims wherein X is methyl, ethyl, fluorine, chlorine, bromine, hydroxy, acetoxy, methoxy, phenoxy, trifluoromethoxy, trifluoromethyl, cyano, nitro, amino, acetylamino, methylsulfonylamino, methylmercapto, methylsulfinyl, methylsulfonyl, carboxy, methoxycarbonyl, tert-butoxycarbonyl, diethylcarbamoyl, (2-aminoethyl)carbamoyl, (2-dimethylaminoethyl)carbamoyl, (E)- and (Z)-2-carboxyethen-1-yl, (E)- and (Z)-(2-tert-butoxycarbonyl)ethen-1-yl, (E)- and (Z)-(ethoxycarbonyl)ethenyl, hydroxymethyl, and allyloxymethyl. 7. Pharmaceutical compositions containing a compound of claims 1-6 in mixture with an acceptable carrier. 8. The use of the compounds of claims 1-6 for the preparation of medicaments for the treatment of tumors.