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1. WO2014060366 - N-SUBSTITUTED 3,4-BIS (CATECHOL) PYRROLE COMPOUNDS, AND THE PREPARATION AND USE THEREOF IN THE TREATMENT OF CANCER

Publication Number WO/2014/060366
Publication Date 24.04.2014
International Application No. PCT/EP2013/071445
International Filing Date 14.10.2013
IPC
C07D 207/333 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
207Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
02with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
30having two double bonds between ring members or between ring members and non-ring members
32with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
33with substituted hydrocarbon radicals, directly attached to ring carbon atoms
333Radicals substituted by oxygen or sulfur atoms
A61K 31/40 2006.01
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
40having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
A61P 35/00 2006.01
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
CPC
A61P 35/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
A61P 35/02
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
02specific for leukemia
C07D 207/333
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
207Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
02with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
30having two double bonds between ring members or between ring members and non-ring members
32with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
33with substituted hydrocarbon radicals, directly attached to ring carbon atoms
333Radicals substituted by oxygen or sulfur atoms
C07D 403/06
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
403Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
02containing two hetero rings
06linked by a carbon chain containing only aliphatic carbon atoms
Applicants
  • CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS) [FR]/[FR]
Inventors
  • COLLIN, Pascal
  • EGOROV, Maxim
  • DELPECH, Bernard
  • BAKALA, Joanna
  • ACHAB, Maria
  • BIGNON, Jérôme
  • THOISON, Odile
  • BENECHIE, Michel
Agents
  • REGIMBEAU
Priority Data
125986816.10.2012FR
Publication Language French (FR)
Filing Language French (FR)
Designated States
Title
(EN) N-SUBSTITUTED 3,4-BIS (CATECHOL) PYRROLE COMPOUNDS, AND THE PREPARATION AND USE THEREOF IN THE TREATMENT OF CANCER
(FR) COMPOSES 3,4-BIS(CATECHOL)PYRROLE-N-SUBSTITUES, LEUR PREPARATION ET UTILISATION DANS LE TRAITEMENT DU CANCER
Abstract
(EN)
The present invention relates to a compound of formula (I) in which: - m is an integer from 0 to 3, preferably from 0 to 2; n is an integer from 0 to 3, preferably from 0 to 2; m + n ≥ 1; EAG is an electro-attractive group chosen independently from among a halogen atom, an NO2, CF3, CCI3, CN, CO2H, (C=O)NR2, CH=NR, (C=S)OR, (C=O)SR, CS2R, SO2R, SO2NR2, SO3R, P(O)(OR)2, P(O)(R)2, B(OR)2 group where R is a (C1 — C6) alkyl radical, a phenyl group or a hydrogen atom; A is a saturated or unsaturated, linear or branched hydrocarbon chain including 1 to 10 atoms of carbon; and R1 and R2 each represent independently from one another a hydrogen atom, a CO-(Ci - C6)-alkyl, (C1 — C6) alkyl, phenyl or phenyl-(C1 — C6)-alkyl group, in which R1 and R2 form, together with the nitrogen atom they carry, a 5- to 15-member heterocycle, optionally substituted by a (C1 — C6) alkyl group; including its stereoisomers and the mixtures thereof, or a pharmaceutically acceptable salt of same.
(FR)
La présente invention concerne un composé de formule (I) dans laquelle : - m est un entier de 0 à 3, de préférence de 0 à 2; - n est un entier de 0 à 3, de préférence de 0 à 2; - m + n ≥ 1; - EAG représente un groupe électroattracteur indépendamment choisi parmi un atome d'halogène, un groupe NO2, CF3, CCI3, CN, CO2H, (C=O)NR2, CH=NR, (C=S)OR, (C=O)SR, CS2R, SO2R, SO2NR2, SO3R, P(O)(OR)2, P(O)(R)2, B(OR)2, où R est un radical (C1 — C6) alkyle, un groupe phényle ou un atome d'hydrogène; - A représente une chaîne hydrocarbonée, saturée ou insaturée, linéaire ou ramifiée, comprenant de 1 à 10 atomes de carbone; et - R1 et R2 représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène, un groupe CO-(Ci - C6)-alkyle, (C1 — C6) alkyle, phényle ou phényle- (C1 — C6)-alkyle, où R1 et R2 forment ensemble, avec l'atome d'azote qui les porte, un hétérocycle à 5 à 15 chaînons, éventuellement substitué par un groupe (C1 — C6) alkyle; y compris ses stéréoisomères et leurs mélanges, ou un sel d'acide pharmaceutiquement acceptable de celui-ci.
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