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US 6,448,241 B1Granted
Thiazolobenzoheterocycles, their preparation and medicaments containing them
AssigneeAventis Pharma S.A.
InventorsJean-Claude Hardy, Jean Bouquerel, Patrick Nemecek, Jean-Claude Aloup, Serge Mignani, Jean-François Peyronel
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I): their racemates, enantiomers, diastereoisomers and inorganic acid salts and organic acid salts thereof, processes for preparing them and the medicaments containing them are discussed.
Claims17
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 atom;
- R2 is a hydrogen atom or an alkyl radical;
- —R3—R4—R5— is a chain having formula —CH2—CH2—S—, —CH2—CH2—SO—, —CH2—CH2—SO2—, —CH2—CH2—Se—, —CH2—CH2—O—, —CH2—CH(R13)—S—, —CH2—CH(R13)—SO— or —CH2—CH(R13)—SO2—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
- R13 is an alkyl or —CH2OH radical;
- and
- wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms.
6 more elements
A compound of formula (II):
- in which:
- —R3—R4—R5— is a chain having the formula —CH2—CH2—S—, —CH2—CH2—Se—, —CH2—CH2—O—, or —CH2—CH(R13)—S—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy, or polyfluoroalkylthio radical;
- R13 is an alkyl or —CH2OH radical;
- and
- wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms.
3 more elements
A process for the preparation of a compound of formula (I):
- or a racemate, an enantiomer, or diastereoisomer or an inorganic or organic acid salt thereof,
- wherein:
- R1 is a sulphur atom;
- R2 is a hydrogen atom;
- —R3—R4—R5— is a chain having formula —CH2—CH2—S—, —CH2—CH2—Se—, —CH2—CH2—O— or —CH2—CH(R13)—S—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
- and
- R13 is an alkyl or —CH2OH radical;
- and
- 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 or an alkali metal selenocyanate with a compound of formula (II):
- wherein:
- —R3—R4—R5— is a chain having formula —CH2—CH2—S—, —CH2—CH2—Se—, —CH2—CH2—O— or —CH2—CH(R13)—S—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
- R13 is an alkyl or —CH2OH radical;
- and
- wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms.
15 more elements
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 atom;
- R2 is an alkyl radical;
- —R3—R4—R5— is a chain having formula —CH2—CH2—S—, —CH2—CH2—SO—, —CH2—CH2—SO2—, —CH2—CH2—Se—, —CH2—CH2—O—, —CH2—CH(R13)—S—, —CH2—CH(R13)—SO— or —CH2—CH(R13)—SO2—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
- R13 is an alkyl or —CH2OH radical;
- and
- 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) or a racemate, an enantiomer, a diastereoisomer or an inorganic or organic acid salt thereof,
- wherein:
- R1 is a sulphur atom;
- R2 is a hydrogen atom;
- —R3—R4—R5— is a chain having formula —CH2—CH2—S—, —CH2—CH2'SO—, —CH2—CH2—SO2—, —CH2—CH2—Se—, —CH2—CH2—O—, —CH2—CH(R13)—S—, —CH2—CH(R13)—SO— or —CH2—CH(R13)—SO2—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
- R13 is an alkyl or —CH2OH radical;
- and
- wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms.
16 more elements
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 atom;
- R2 is a hydrogen atom or an alkyl radical;
- —R3—R4—R5— is a chain having formula —CH2—CH2—SO—, —CH2—CH2—SO2—, —CH2—CH(R13)—SO— or —CH2—CH(R13)—SO2—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
- R13 is an alkyl or —CH2OH radical;
- and
- 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:
- oxidizing a compound of general formula (I) or a racemate, an enantiomer, a diastereoisomer or an inorganic or organic acid salt thereof, in which
- R1 is a sulphur atom;
- R2 is a hydrogen atom or an alkyl radical;
- —R3—R4—R5— is a chain having formula —CH2—CH2—S—, or —CH2—CH(R13)—S—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
- R13 is an alkyl or —CH2OH radical;
- and
- wherein, unless otherwise indicated, said alkyl and alkoxy radicals and portions thereof have from 1 to 6 straight- or branched-chain carbon atoms.
15 more elements
A pharmaceutical composition, said composition comprising a pharmaceutically effective amount of a compound of formula (I):
- or a racemate, an enantiomer, a diastereomer or an inorganic or organic acid salt thereof,
- in which:
- R1 is a sulphur atom;
- R2 is a hydrogen atom or an alkyl radical;
- —R3—R4—R5— is a chain having formula —CH2—CH2—S—, —CH2—CH2—SO—, —CH2—CH2—SO2—, —CH2—CH2—Se—, —CH2—CH2—O—, —CH2—CH(R13)—S—, —CH2—CH(R13)—SO— or —CH2—CH(R13)—SO2—;
- R6 is a polyfluoroalkyl, polyfluoroalkoxy or polyfluoroalkylthio radical;
- R13 is an alkyl or —CH2OH radical;
- and
- 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.
8 more elements
Dependencies are inferred from the claim text.