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AssigneeLes Laboratoires Servier
InventorsJean-Claude Ortuno, Alexis Cordi, Jean-Michel Lacoste, Vincent Lacoste, Pauline Lacoste, Imre Fejes, Michael Burbridge, John Hickman, Alain Pierre
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Compounds of formula (I): wherein: m and n represent 1 or 2, A represents a pyrrolyl group, X represents a C(O), S(O) or SO2 group, R1 and R2 represent an alkyl group or, together with the nitrogen atom carrying them, form a heterocyclic group, R3 and R4, together with the atoms carrying them, form a heterocyclic group, R5 represents a hydrogen atom or an alkyl group, R6 represents a hydrogen atom or a halogen atom. Medicinal products containing the same which are useful in treating cancer.
1- A compound selected from those of formula (I):
2- compound of claim 1, wherein n represents 1.
3- compound of claim 1, wherein m represents 1.
4- compound of claim 1, wherein R1 and R2 represent an alkyl group.
5- compound of claim 1, wherein R1 and R2, together with the nitrogen atom carrying them, form a 5- or 6-membered monocyclic group.
6- compound of claim 1, wherein R1 and R2, together with the nitrogen atom carrying them, form a morpholinyl group.
7- compound of claim 1, wherein R3 and R4, together with the X group and the nitrogen atom carrying them, form a thiazolidinedionyl group.
8- compound of claim 1, wherein R5 represents a hydrogen atom.
9- compound of claim 1, wherein R6 represents a hydrogen atom.
10- compound of claim 1, wherein X represents a C═O group.
11- compound of claim 1, wherein A represents a 1H-pyrrol-2,4-yl group.
12- compound of claim 1, wherein R1 and R2, together with the nitrogen atom carrying them, form a morpholinyl group, m and n have the value 1, R5 and R6 represent a hydrogen atom and A represents a 1H-pyrrol-2,4-yl group.
13- compound of claim 1, which is selected from 3-[(3-{[4-(4-morpholinylmethyl)-1H-pyrrol-2-yl]methylene}-2-oxo-2,3-dihydro-1H-indol-5-yl)methyl]-1,3-thiazolidine-2,4-dione, its geometric isomers, and addition salts thereof with a pharmaceutically acceptable acid or base.
14- compound of claim 1, which is selected from 3-[((3Z)-3-{[4-(4-morpholinylmethyl)-1H-pyrrol-2-yl]methylene}-2-oxo-2,3-dihydro-1H-indol-5-yl)methyl]-1,3-thiazolidine-2,4-dione, and addition salts thereof with a pharmaceutically acceptable acid or base.
15- A pharmaceutical composition comprising at least one compound of claim 1, or an addition salt thereof with a pharmaceutically acceptable acid or base, in combination with one or more pharmaceutically acceptable excipients.
16- A method of inhibiting the migration of cancerous cells in a subject in need thereof comprising administration of an effective amount of a compound of claim 1.
17- A method of treating metastatic cancers in a subject in need thereof comprising administration of an effective amount of a compound of claim 1.
18- A method of treating a condition selected from cancers of the colon, breast, liver, kidneys, brain, oesophagus, melanomas, myelomas, cancers of the ovary, non-small cell lung cancers, small cell lung cancers, cancers of the prostate and pancreas, and sarcomas in a subject in need thereof comprising administration of an effective amount of a compound of claim 1.
19- A composition comprising a compound of claim 1 and an anticancer agent selected from genotoxic agents, mitotic poisons, antimetabolites, proteasome inhibitors and kinase inhibitors.
20- A method of treating cancer in a subject in need thereof comprising administration of an effective amount of a composition of claim 19.
21- A method of treating cancer in a subject in need thereof comprising administration of an effective amount of a compound of claim 1 in combination with radiotherapy.