Patent Application

App. No. 13/973,987

Abstract

Claims (53)

1 . A process for preparing a chirally purified substituted 4,5,6,7,-tetrahydro-benzothaizole diamine comprising:

heating a solution comprising entantiomerically enriched 4,5,6,7-tetrahydro-benzothiazole diamine of general formula (I):

wherein:

R 1 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl or alkynyl group each having 3 to 6 carbon atoms, an alkanoyl group having 1 to 6 carbon atoms, a phenyl alkyl or phenyl alkanoyl group having 1 to 3 carbon atoms in the alkyl part, whilst the above-mentioned phenyl nuclei may be substituted by 1 or 2 halogen atoms;

R 2 represents a hydrogen atom or an alkyl group with 1 to 4 carbon atoms;

R 3 represents a hydrogen atom, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, an alkanoyl group having 1 to 7 carbon atoms, a phenyl alkyl or phenyl alkanoyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms,

R 4 represents a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms; and

at least one or R 1 , R 2 , R 3 or R 4 is a hydrogen in an organic solvent; and

an alkyl sulfonate or an alkyl halide in a solvent to form a reaction mixture;

reacting the reaction mixture; and

recovering a chirally purified substituted 4,5,6,7-tetrahydro-benzothiazole diamine.

2 - 28 . (canceled)

29 . Chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole prepared by a process comprising:

heating a solution comprising entantiomerically enriched 2,6 diamino-4,5,6,7-tetrahydro-benzothiazole and a propyl halide or a propyl sulfonate to form a reaction mixture;

reacting the reaction mixture; and

recovering the chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole.

30 - 52 . (canceled)

53 . A process for preparing a chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole comprising:

heating a solution comprising 2,6 diamino-4,5,6,7-tetrahydro-benzothiazole in an organic solvent;

adding to the heated solution propyl sulfonate or a propyl halide to form a reaction mixture; and

reacting the reaction mixture for up to about 12 hours.

54 - 79 . (canceled)

80 . A process for preparing chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole comprising:

heating a solution comprising 2,6 diamino-4,5,6,7-tetrahydro-benzothiazole;

adding a propyl halide or a propyl sulfonate to the heated solution slowly over from about 0.5 hours to about 2 hours to form a reaction mixture;

reacting the reaction mixture; and

recovering the chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole.

81 - 101 . (canceled)

102 . Chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole prepared by a process comprising:

heating a solution comprising 2,6 diamino-4,5,6,7-tetrahydro-benzothiazole;

adding a propyl halide or a propyl sulfonate to the heated solution slowly over from about 0.5 hours to about 2 hours to form a reaction mixture;

reacting the reaction mixture; and

recovering the chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole.

103 - 125 . (canceled)

126 . A process for preparing chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole comprising:

dissolving entantiomerically enriched 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole in an organic solvent to form a solution;

heating the solution to from about 50° C. to about 125° C.;

adding an acid to the solution to form a reaction mixture; and

recovering the chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole.

127 - 128 . (canceled)

129 . A chirally pure 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole prepared by a process of claim 126 .

130 . A process for preparing chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole comprising:

dissolving entantiomerically enriched 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole in an organic solvent to form a solution;

heating the solution to from about 50° C. to about 125° C.;

adding an achiral salt to the solution to form a reaction mixture; and

recovering the chirally purified 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole.

131 - 132 . (canceled)

133 . A chirally pure 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole prepared by a process of claim 130 .

134 . A process for preparing a 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride comprising:

dissolving a 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole salt in an organic solvent to form a solution;

cooling the solution to a temperature of from about 0° C. to about 5° C.;

adding concentrated HCl and an organic solvent to the cooled solution; and

stirring the solution at a temperature of about 0° C. to about 5° C.

Assignments (8)