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1. A process for the separation of enantiomers of compounds of formula (I) below: wherein: R1, R2, R3 and R4 are chosen independently from the group consisting of the following groups:
H;(C1-C20) alkyl optionally substituted by halogen, (C1-C5) alkyl, (C1-C5) alkoxy or (C3-C8) cycloalkyl;(C2-C20) alkylene optionally substituted by halogen, (C1-C5) alkyl or (C1-C5) alkoxy;(C2-C20) alkyne optionally substituted by halogen, (C1-C5) alkyl or (C1-C5) alkoxy;(C3-C8) cycloalkyl optionally substituted by (C1-C5) alkyl or (C1-C5) alkoxy;(C3-C8) heterocycloalkyl bearing one or more hetero atoms chosen from N, O and S and optionally substituted by (C1-C5) alkyl or (C1-C5) alkoxy;(C6-C14) arylalkyl (C1-C20) optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl;(C6-C14) aryl optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl; or(C5-C13) heteroaryl bearing one or more hetero atoms chosen from N, O and S and optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl; R1 and R2, on the one hand, and R3 and R4, on the other hand, possibly forming with the nitrogen atom to which they are linked an n-membered ring (n between 3 and 8) optionally comprising one or more hetero atoms chosen from N, O and S and possibly being substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl; R5 is chosen from the group consisting of the following groups:
(C1-C20) alkyl optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl;(C2-C20) alkylene optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl;(C2-C20) alkyne optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl;(C3-C8) cycloalkyl optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl;(C3-C8) heterocycloalkyl bearing one or more hetero atoms chosen from N, O and S and optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl;(C6-C14) aryl optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl;(C5-C13) heteroaryl bearing one or more hetero atoms chosen from N, O and S and optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl;(C6-C14) arylalkyl(C1-C5) optionally substituted by amino, hydroxyl, thio, halogen, (C1-C5) alkyl, (C1-C5) alkoxy, (C1-C5) alkylthio, (C1-C5) alkylamino, (C6-C14) aryloxy, (C6-C14) arylalkoxy (C1-C5), cyano, trifluoromethyl, carboxyl, carboxymethyl or carboxyethyl, or a salt thereof, comprising the following steps:
step 1: formation of a diastereoisomeric tartrate salt of the triazine derivative with a single enantiomer of tartaric acid by reaction of a salt of the compound of formula (I) with a single enantiomer of tartaric acid,step 2: separation of both diastereoisomers of the tartrate salt,step 3: transformation of at least one isolated diastereoisomer of the tartrate salt into another salt, andstep 4: recovery of the triazine salt obtained in step 3.
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