Thiazolobenzoheterocycles, their preparation and medicaments containing them

A compound of formula (II):

• in which:
• —R3—R4—R5— is a chain having the formula —CH2—CH2—N(R10)— or —CH2—CO—N(R10)—;
• R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
• and
• R10 is a hydrogen atom or an alkyl radical;
• wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms;
• with the proviso that the following compounds are excluded:
• 6-trifluoromethyl-1,2,3,4-tetrahydroquinoxaline and 2-oxo-7-trifluoromethyl-3,4-dihydroquinoxaline.

A pharmaceutical composition, said composition comprising a pharmaceutically effective amount of a compound of formula (I):

• or a racemate, an enantiomer, a diastereoisomer or an inorganic or organic acid salt thereof,
• in which:
• R1 is a sulphur;
• R2 is a hydrogen atom or an alkyl radical;
• —R3—R4—R5— is a chain having the formula —CH2—CH2—N(R10)— or —CH2—CO—N(R10)—;
• R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
• and
• R10 is a hydrogen atom or an alkyl radical;
• wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms;
• and
• a pharmaceutically compatible diluent.

A process for the preparation of a compound of formula (I):

• or a racemate, an enantiomer, a diastereomer or an inorganic or organic acid salt thereof,
• wherein:
• R1 is a sulphur;
• R2 is a hydrogen atom;
• —R3—R4—R5— is a chain having the formula —CH2—CH2—N(R10)— or —CH2—CO—N(R10)—;
• R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
• and
• R10 is a hydrogen atom or an alkyl radical;
• wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms;
• said process comprising:
• reacting an alkali metal thiocyanate with a compound of formula (II):
• wherein:
• —R3—R4—R5— is a chain having the formula —CH2—CH2—N(R10)— or —CH2—CO—N(R10)—;
• R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
• and
• R10 is a hydrogen atom or an alkyl radical;
• wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms.

A process for the preparation of a compound of formula (I):

• or a racemate, an enantiomer, a diastereoisomer or an inorganic or organic acid salt thereof,
• wherein:
• R1 is a sulphur;
• R2 is an alkyl radical;
• —R3—R4—R5— is a chain having the formula —CH2—CH2—N(R10)— or —CH2—CO—N(R10)—;
• R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
• and
• R10 is a hydrogen atom or an alkyl radical;
• wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms;
• said process comprising:
• alkylating a compound of formula (I)
• wherein:
• R1 is a sulphur;
• R2 is a hydrogen atom;
• —R3—R4—R5— is a chain having the formula —CH2—CH2—N(R10)— or —CH2—CO—N(R10)—;
• R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
• and
• R10 is a hydrogen atom or an alkyl radical;
• wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms.

A method for making a pharmaceutical composition, said method comprising including, with a pharmaceutically compatible diluent, a pharmaceutically effective amount of a compound of formula (I):

• or a racemate, an enantiomer, a diastereoisomer or an inorganic or organic acid salt thereof,
• in which:
• R1 is a sulphur;
• R2 is a hydrogen atom or an alkyl radical;
• —R3—R4—R5— is a chain having the formula —CH2—CH2—N(R10)— or —CH2—CO—N(R10)—;
• R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
• and
• R10 is a hydrogen atom or an alkyl radical;
• wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms.