Imidazolidine-2,4-dione derivatives, and use thereof as a cancer drug
AssigneeIpsen Pharma S.A.S.
InventorsGrégorie Prevost, Serge Auvin, Christophe Lanco, Anne-Marie Liberatore, Olivier Lavergne
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Abstract
The present application relates to novel imidazolidine-2,4-dione derivatives of the general formula (I), where R1, R2, R3, R4, X, and Y are variables. Said materials have an antiproliferative activity. They are particularly useful for treating pathological conditions and diseases, such as cancer, that are linked to abnormal cell proliferation. The invention also relates to pharmaceutical compositions containing said materials and to the use thereof for preparing a drug.
Claims21
A compound formula (I)
- in racemic or enantiomeric form or any combination thereof, wherein
- R1 and R2 represent independently a halogen atom, or an alkyl, haloalkyl, alkoxy, cyano, nitro, amino, alkylamino, dialkylamino, —NR8—CO—R5, —NR8—SO2—R5, —NR8—CO—(CH2)n—NR6, R7, —NR8—SO2—(CH2)n—NR6R7, or —CO—NH2 radical;
- n represents an integer chosen from 0, 1, 2, 3, 4, 5, or 6;
- R5 represents an alkyl, aryl, or heteroaryl radical;
- R6 and R7 represent independently a hydrogen atom, an alkyl, or an alkyloxycarbonyl radical;
- R8 represents a hydrogen atom or an alkyl radical;
- R3 represents an alkyl radical or a hydrogen atom;
- or the two R3 radicals form together with the carbon atom to which they are attached a cycloalkyl radical comprising 3 to 6 members;
- R4 represents a haloalkyl radical with 2 to 10 carbon atoms;
- Y represents a linear or branched alkylene chain with 2 to 14 carbon atoms, wherein the chain is saturated or unsaturated, and optionally comprising one or more additional —O-members;
- X represents —S—, —SO—, —SO2—, —S═N(R9)— or —S(O)═N(R9)—;
- R9 represents a hydrogen atom or a haloalkylcarbonyl radical,
- or a pharmaceutically acceptable salt thereof.
A method of preparing a compound of formula (I.3)
- comprising oxidizing the compound of formula (I.2) of claim
- to obtain a sulphone of formula (I.3).
An intermediate compound selected from:
- 1-(5-iodopentyl)-5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione;
- 1-(8-iodooctyl)-5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione;
- 1-(9-bromononyl)-5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione;
- 4-[3-(9-bromononyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile;
- 5,5-dimethyl-3-(3-methyl-4-nitrophenyl)imidazolidine-2,4-dione;
- or
- 1-(9-bromononyl)-5,5-dimethyl-3-(3-methyl-4-nitrophenyl)imidazolidine-2,4-dione.
Dependencies are inferred from the claim text.