| US 7,482,352 B2 | ||
| Chemical derivatives and their application as antitelomerase agents | ||
| Patrick Mailliet, Fontenay Sous Bois (France); Abdelazize Laoui, Bridgewater, N.J. (US); Jean-Francois Riou, Reims (France); Gilles Doerflinger, Les Ulis (France); Jean-Louis Mergny, Villejuif (France); Francois Hamy, Illzach (France); and Thomas Caulfield, Paris (France) | ||
| Assigned to Aventis Pharma S.A., Antony (France) | ||
| Filed on Nov. 19, 2004, as Appl. No. 10/993,637. | ||
| Application 10/993637 is a division of application No. 10/103883, filed on Mar. 25, 2002, granted, now 6,887,873. | ||
| Claims priority of provisional application 60/332009, filed on Nov. 23, 2001. | ||
| Claims priority of application No. 01 03916 (FR), filed on Mar. 23, 2001; and application No. 01 10370 (FR), filed on Aug. 02, 2001. | ||
| Prior Publication US 2005/0070571 A1, Mar. 31, 2005 | ||
| Int. Cl. C07D 401/10 (2006.01); C07D 401/14 (2006.01); C07D 403/10 (2006.01); C07D 403/14 (2006.01); A61K 31/4427 (2006.01); A61K 31/4709 (2006.01); A61K 31/4725 (2006.01); A61K 31/517 (2006.01); A61P 35/00 (2006.01); A61P 35/02 (2006.01) | ||
| U.S. Cl. 514—258.1 [544/283; 544/284] | 12 Claims |
| 1. A compound which binds a G-quadruplex structure of DNA or RNA, wherein the compound corresponds to the following formula:
nitrogen-containing aromatic ring-NR3-distribution agent-NR′3-aromatic ring
in which:
the nitrogen-containing aromatic ring represents:
a quinolinyl or isoquinolinyl radical optionally substituted with one or more radicals chosen from among:
N(Ra)(Rb), wherein Ra and Rb are identical or different and represent hydrogen or C1-C4 alkyl radical, and
a short-chain C1-C4 alkoxy or alkyl group,
a quinolinyl or isoquinolinyl radical possessing a nitrogen atom in quaternary form,
or
a pyridinyl radical;
or wherein the nitrogen-containing aromatic ring is replaced by a benzimidinyl radical;
the aromatic ring represents:
a quinolinyl radical optionally substituted with one or more radicals chosen from among:
N(Ra)(Rb), wherein Ra and Rb are identical or different and represent hydrogen or C1-C4 alkyl radical, and
a short-chain C1-C4 alkoxy or alkyl group,
a quinolinyl radical possessing a nitrogen atom in quaternary form,
a benzamidinyl radical,
a pyridinyl radical,
a phenyl ring optionally substituted with a halogen group, C1-C4 alkoxy group, cyano group, carbonylamino group optionally
substituted with one or more C1-C4 alkyl groups, guanyl group, C1-C4 alkylthio group, amino group, C1-C4 alkylamino group,
C1-C4 dialkylamino group for each alkyl, C1-C4 dialkylamino group for each alkyl in which the alkyl portions together form
a C3-C8 ring, nitro group, C1-C4 alkyleneamino group, or C2-C4 alkenyleneamino group, or
a mono- or bi- or tricyclic heterocyclic ring comprising 0 to 2 heteroatoms per ring wherein at least one heteroatom is present
in at least one ring that is optionally substituted with one or more C1-C4 alkyl groups, C1-C4 alkylene groups, or C2-C4 alkenylene
groups;
R3 and R′3 are identical or different and represent, independently of one another, hydrogen or C1-C4 alkyl radical;
the distribution agent represents:
a diazine group selected from a quinazoline;
wherein the diazine group is optionally substituted with:
an aromatic ring as defined above, or
a radical XR1(R2), where X represents a nitrogen to form NR1R2, a linear or branched C1-C6 alkyl radical to form alkR1R2,
an oxygen to form OR1, or a sulfur to form SR1,
wherein R1 and R2, which are identical or different, are chosen from among hydrogen; a C1-C8 alkyl radical optionally substituted
with one or more radicals which are identical or different; an aromatic ring as defined above; a quinuclidine radical; a pyrrolidinyl
radical which is optionally substituted with an alkyl or phenylalkyl radical where alkyl is C1-C4 alkyl; a piperazinyl radical
which is optionally substituted with an alkyl, cycloalkyl or phenylalkyl radical; a morpholinyl radical; a pyridyl radical
or a piperidyl radical which are optionally substituted with one or more alkyl or phenylalkyl radicals where alkyl is C1-C4
alkyl; an indazolyl radical; a naphthyl radical; a benzotriazole radical; a pyrimidinyl radical optionally substituted with
one or more C1-C4 alkyls; and an acenaphthene radical; or
a radical where X represents N or alkyl, R1 and R2 are as defined above, and R1, R2 and X form a saturated or unsaturated
3- to 6-membered monocyclic or 8- to 10-membered bicyclic radical optionally containing one or two identical or different
heteroatoms chosen from N, O or S;
or any salts, isomeric forms, racemates, enantiomers and diastereoisomers thereof.
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