CRYSTALLINE SUBSTITUTED 5-FLUORO-1H-PYRAZOLOPYRIDINES AND PROCESS FOR PREPARING

Abstract

The present application relates to a novel and efficient process for preparing novel substituted 5-fluoro-1H-pyrazolopyridines of the formula (VI)

##STR00001##

which are suitable as an intermediate for production of medicaments and for production of medicaments for treatment and/or prophylaxis of cardiovascular disorders. More particularly, the 5-fluoro-1H-pyrazolopyridines of the formula (VI) are suitable for preparation of the compound of the formula (I)

##STR00002##

which serves for production of medicaments, for production of medicaments for treatment and/or prophylaxis of cardiovascular disorders.

Claims

1-4. (canceled)

5. A process for preparing a compound of formula (IIIa) ##STR00085## comprising reacting the trifluoromethanesulphonic anhydride of the formula (X) ##STR00086## with 2,2,3,3-tetrafluoro-1-propanol of the formula XI, ##STR00087## without solvent, and reacting the resulting 2,2,3,3-tetrafluoropropyl trifluoromethanesulphonate of the formula XII ##STR00088## with morpholine to give a compound of the formula (XIII) ##STR00089## and reacting the compound of formula (XIII) with methyl methanesulphonate to give a compound of the formula (XIV) ##STR00090## and with sodium hydroxide to give a compound of the formula (XV) ##STR00091## and finally adding morpholine to the compound of formula (XV) to give the compound of the formula (IIIa).

6-16. (canceled)

17. A crystalline substance compound of the formula (I) in the form of the di-dimethyl sulphoxide solvate, ##STR00092##

18. The crystalline substance compound of claim 17, wherein the x-ray diffractogram of the compound exhibits peak maxima of the 2 theta angle at 18.8, 20.3, 21.7.

19. The crystalline substance compound of claim 18, wherein the x-ray diffractogram of the compound exhibits peak maxima of the 2 theta angle at 12.0, 16.6, 17.8, 18.8, 20.3, 21.7.

20. The crystalline substance compound of claim 17, wherein the IR spectrum of the compound exhibits band maxima at 1720, 1628, 1481 cm.sup.1.

21. The crystalline substance compound of claim 20, characterized in that the IR spectrum of the compound exhibits band maxima at 1720, 1628, 1481, 1234, 1041, 1017 cm.sup.1.

22. A process for preparing the crystalline substance compound of claim 17, comprising: stirring a solution of compounds of formula (I), wherein the compounds of formula (I) are present in one or more polymorphs or as a solvate in dimethyl disulphoxide or a mixture of dimethyl sulphoxide and an inert solvent at a temperature of 20 C.-120 C., and isolating the di-dimethyl sulphoxide solvate.

23-24. (canceled)

25. A compound of the formula (XIV) ##STR00093## or salts, solvates and solvates of the salts thereof.

26. A compound of the formula (XV) ##STR00094## or salts, solvates and solvates of the salts thereof.

Description

FIGURES

[0329] FIG. 1: IR spectrum of the compound of the formula (I) in polymorphs I, II and III

[0330] FIG. 2: IR spectrum of the compound of the formula (I) in polymorphs IV, V and as the triacetic acid solvate

[0331] FIG. 3: IR spectrum of the compound of the formula (I) as the di-DMSO solvate,

[0332] DMF/water solvate and monohydrate

[0333] FIG. 4: IR spectrum of the compound of the formula (I) as the dihydrate

[0334] FIG. 5: X-ray diffractogram of the compound of the formula (I) in polymorph I

[0335] FIG. 6: X-ray diffractogram of the compound of the formula (I) in polymorph II

[0336] FIG. 7: X-ray diffractogram of the compound of the formula (I) in polymorph III

[0337] FIG. 8: X-ray diffractogram of the compound of the formula (I) in polymorph IV

[0338] FIG. 9: X-ray diffractogram of the compound of the formula (I) in polymorph V

[0339] FIG. 10: X-ray diffractogram of the compound of the formula (I) as the triacetic acid solvate

[0340] FIG. 11: X-ray diffractogram of the compound of the formula (I) as the di-DMSO solvate

[0341] FIG. 12: X-ray diffractogram of the compound of the formula (I) as the DMF-water solvate

[0342] FIG. 13: X-ray diffractogram of the compound of the formula (I) as the monohydrate

[0343] FIG. 14: X-ray diffractogram of the compound of the formula (I) as the dihydrate