EP 2139860 A2 20100106 - DERIVATIVES OF THE AMINATED HYDROXYQUINOLINE CLASS FOR TREATING CANCERS
Title (en)
DERIVATIVES OF THE AMINATED HYDROXYQUINOLINE CLASS FOR TREATING CANCERS
Title (de)
DERIVATE DER AMINIERTEN HYDROXYCHINOLINKLASSE ZUR KREBSBEHANDLUNG
Title (fr)
DÉRIVÉS DE LA CLASSE DES HYDROXYQUINOLÉINES AMINÉES POUR LE TRAITEMENT DE CANCERS.
Publication
Application
Priority
- FR 2008000399 W 20080325
- FR 0702154 A 20070323
Abstract (en)
[origin: FR2913976A1] Hydroxy quinoline amino compounds (I) and their enantiomers are new. Hydroxy quinoline amino compounds of formula (I) and their enantiomers are new. R 1, R 2H, 1-10C alkyl, halo group comprising F, Br, Cl or a group -O-R, one of R 1 and R 2 is phenyl compounds of formula (a) having asymmetric carbon; R : 1-10C alkyl, 4-8C cycloalkyl, 1-10C alcohol, 4-8C heterocycloalkyl which contains heteroatoms of N, O or S, 2-10C alkenyl or alkynyl, (hetero)aryl, alkylphenyl or 1-10C alkyl, or alkanoyl phenyl having 1-3 C atoms of alkonyl, phenyl optionally substituted with 1-2 halo atoms of F, Br, I or Cl or -CF 3, R-NO 2 (where R is 1-10C alkyl or 5-methylene-8-hydroxyquinole); R 3-R 7H, 1-10C alkyl, 4-8C cycloalkyl, 2-10C alkenyl, 2-10C alkynyl, -CF 3, -O-R (where R is 5-methylene-8-hydroxyquinole); X, Y 1H, 1-10C alkyl, aryl, -OH, Cl, Br, I, F, -CF 3, R-NH 2, -CN, R-NO 2, R-COOH or -COOR, where R is 1-10C alkyl, either in the case one of R 1 and R 2 is Y 1-N-Y 1 or Y 1 is a -(CH 2) n-, aryl optionally substituted with 1 or 2 atoms of halo comprising F, Br, Cl, or 1-10C alkyl, 4-8C heterocycloalkyl, and where Y 1 is 5-methylene-8-hydroxyquinole, the other atoms is H, or in the case one of R 1 and R 2 is -(CH 2) n-naphthalene, where the naphthalene is optionally substituted with 1-10C alkyl, 4-8C cycloalkyl, 2-10C alkenyl, 2-10C alkynyl, 1-10C alkanoyl, -CF 3 or -O-R, where R is 1-10C alkyl, ant the other is H, 5-methylene-8-hydroxyquinole or t-butyloxycarbonyl, or R 1 and R 2 form a 4-8C cyclic aliphatic ring optionally substituted with 1-6C alkyl or -O-R, where R is 1-10C alkyl, or aryl, possibly H, 1-6C alkyl optionally substituted with F, Br or Cl, or one of R 1 and R 2 form 5-6 membered cyclic polyamine or unsubstituted piperazine or which one of the carbon atom in the cycle is substituted with 1-6C alkyl and/or in which one of the N atom is not a part in the group -CH 2-NR 1R 2 or substituted by 5-methylene-8-hydroxyquinole, or R 1 and R 2 form a polyazamacrocycle (cyclam) comprising 1,4,8,12-tetraazacyclopentadecan or 1,4,8,11-tetraazacyclotetradecane (both are unsubstituted), where at least one of the N of the cycle in position 1, 4 and 8 is replaced with t-butoxycarbonyl, 5-methylene-8-hydroxyquinole or -(CH 2) n-phenyl-(CH 2) n-Z; n : 1-10; and Z : one of N of a 1,4,8,12-tetraazacyclopentadecane or a 1,4,8,11- tetraazacyclotetradecane in which the other atoms N of the cycle in position 1,4 and 8 are optionally substituted with t-butoxycarbonyl. [Image] [Image] ACTIVITY : Cytostatic. MECHANISM OF ACTION : None given. (I) were tested for cytotoxic effect in KB cell line. The medium inhibitory concentration value of 5,5'-(benzylazanediyl)bis(methylene)diquinolein-8-ol was 0.0015/0.005 mu M.
IPC 8 full level
C07D 215/20 (2006.01)
CPC (source: EP US)
A61K 31/47 (2013.01 - US); A61K 31/4709 (2013.01 - US); A61P 35/00 (2017.12 - EP); A61P 35/04 (2017.12 - EP); C07D 215/20 (2013.01 - EP US); C07D 401/06 (2013.01 - EP US)
Citation (search report)
See references of WO 2008135671A2
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR
DOCDB simple family (publication)
FR 2913976 A1 20080926; FR 2913976 B1 20130426; AU 2008248475 A1 20081113; AU 2008248475 B2 20131003; CA 2680803 A1 20081113; CN 101641332 A 20100203; CN 101641332 B 20140312; EP 2139860 A2 20100106; JP 2010522147 A 20100701; JP 5555494 B2 20140723; US 2010120856 A1 20100513; US 2013102630 A1 20130425; US 8324243 B2 20121204; US 8614230 B2 20131224; WO 2008135671 A2 20081113; WO 2008135671 A3 20090522
DOCDB simple family (application)
FR 0702154 A 20070323; AU 2008248475 A 20080325; CA 2680803 A 20080325; CN 200880007473 A 20080325; EP 08787845 A 20080325; FR 2008000399 W 20080325; JP 2009554065 A 20080325; US 201213690137 A 20121130; US 53269508 A 20080325