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1. (WO1997018215) ANALOGUES OF N-ACETYLARDEEMIN, METHOD OF PREPARATION AND USES THEREOF
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1997/018215 International Application No.: PCT/US1996/019086
Publication Date: 22.05.1997 International Filing Date: 15.11.1996
IPC:
C07D 487/22 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
487
Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/-C07D477/183
22
in which the condensed system contains four or more hetero rings
Applicants:
SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH [US/US]; 1275 York Avenue New York, NY 10021, US (AllExceptUS)
THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF [US/US]; NEW YORK W. 116th Street & Broadway New York, NY 10027, US (AllExceptUS)
DANISHEFSKY, Samuel [US/US]; US (UsOnly)
DEPEW, Kristopher [US/US]; US (UsOnly)
MARSDEN, Stephen, P. [GB/GB]; GB (UsOnly)
BORNMANN, William [US/US]; US (UsOnly)
WOO, Jonathan, C., G. [US/US]; US (UsOnly)
CHOU, Ting-Chao [US/US]; US (UsOnly)
SCHKERYANTZ, Jeffrey [US/US]; US (UsOnly)
ZATORSKI, Andrej [US/US]; US (UsOnly)
Inventors:
DANISHEFSKY, Samuel; US
DEPEW, Kristopher; US
MARSDEN, Stephen, P.; GB
BORNMANN, William; US
WOO, Jonathan, C., G.; US
CHOU, Ting-Chao; US
SCHKERYANTZ, Jeffrey; US
ZATORSKI, Andrej; US
Agent:
JORAN, A. David ; Darby & Darby P.C. 805 Third Avenue New York, NY 10022, US
Priority Data:
60/006,75015.11.1995US
Title (EN) ANALOGUES OF N-ACETYLARDEEMIN, METHOD OF PREPARATION AND USES THEREOF
(FR) ANALOGUES DE LA N-ACETYLARDEEMINE, PROCEDES DE PREPARATION ET UTILISATION DESDITS ANALOGUES
Abstract:
(EN) The present invention provides a compound having structure (I) wherein R1, R6 and R7 are independently hydrogen, OH, NH2, SH, halogen, C1-C9 linear or branched chain alkyl, alkylmercapto, alkylamino, dialkylamino, alkoxy, phenyl, etc; wherein R0 and R2 are independently hydrogen, OH, linear or branched chain alkyl, -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, wherein R3 and R4 are independently hydrogen, halogen, C1-C9 linear or branched chain alkyl, phenyl, etc; wherein R5 is hydrogen, C1-C9 linear or branched chain alkyl, phenyl, etc; an wherein R8 is hydrogen, C1-C9 linear or branched chain acyl, benzoyl, etc; with the proviso that (a) when R2 is -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, then R0 is hydrogen; (b) when R0 is -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 or -CR3R3-CH=CHR4, then R2 is OH; and (c) when (i) R0 or R2 is -CR3R3-CH=CHR4, (ii) R3 and R5 are CH3 and (iii) R4 is hydrogen, then R1, R6 and R7 are not all hydrogen. Also provided are related compounds and compositions, and methods of inhibiting the growth of multidrug resistant cells by means of MDR reversal, collateral sensitivity and quantitative synergism.
(FR) L'invention concerne un composé ayant la structure (1). Dans cette formule, R1, R6 et R7 représentent indépendamment l'un de l'autre, un hydrogène, OH, NH2, SH, halogène, C1-C9 alkyle linéaire ou ramifié, alkylmercapto, alkylamino, dialkylamino, alcoxy, phényle, etc; R0 et R2 représentent indépendamment l'un de l'autre, un hydrogène, OH, alkyle linéaire ou ramifié, -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 ou -CR3R3-CH=CHR4; R3 et R4 représentent indépendamment l'un de l'autre, un hydrogène, halogène, C1-C9 alkyle linéaire ou ramifié, phényle, etc; R5 est un hydrogène, C1-C9 alkyle linéaire ou ramifié, phényle, etc; R8 est un hydrogène, un C1-C9 acyle linéaire ou ramifié, benzoyle, etc; à condition que (a) quand R2 est -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 ou -CR3R3-CH=CHR4, R0 soit un hydrogène; (b) quand R0 est -CR3R3-CH(O)CH2, -CR3R3-CH2CH3, -CR3R3-CH2CH2OH, -CR3R3-CH(OH)R4 ou -CR3R3-CH=CHR4, R2 soit OH; et (c) quand (i) R0 ou R2 est -CR3R3-CH=CHR4, (ii) R3 et R5 sont CH3 et (iii) R4 est un hydrogène, R1, R6 et R7 ne soient pas tous des hydrogènes. L'invention concerne également des composés dérivés et des compositions les contenant, ainsi que des méthodes pour inhiber la croisance de cellules présentant une résistance multiple aux médicaments, par une diminution de cette résistance, une augmentation de la sensibilité collatérale et par un effet de synergie.
Designated States: AU, CA, JP, MX, RU, US
European Patent Office (AT, BE, CH, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
EP0815111JPH10512899CA2209775AU1997011425