Salt forms of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine
The present invention relates to the stereospecific synthesis of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine, its salt forms, and novel polymorphic forms of these salts.
1. A composition comprising a mono-orotate salt of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine, wherein the composition is substantially free of (S)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine.
2. The composition of claim 1 , wherein the salt is in crystalline form.
3. The composition of claim 2 , wherein the crystalline form is characterized by a powder x-ray diffraction pattern comprising at least one of the following peaks:
2θ
2.55 ± 0.1°
6.54 ± 0.1°
8.66 ± 0.1°
13.26 ± 0.1°
14.56 ± 0.1°
15.98 ± 0.1°
17.47 ± 0.1°
18.53 ± 0.1°
19.30 ± 0.1°
20.26 ± 0.1°
21.05 ± 0.1°
22.02 ± 0.1°
23.14 ± 0.1°
24.32 ± 0.1°
25.56 ± 0.1°
26.87 ± 0.1°
27.84 ± 0.1°
28.76 ± 0.1°
29.53 ± 0.1°.
4. The composition of claim 2 , wherein the crystalline form is characterized by an XRPD pattern that substantially corresponds to that shown in FIG. 6 .
5. A pharmaceutical composition comprising the composition of claim 1 and at least one pharmaceutically acceptable carrier, diluent, or excipient.
6. A method of treating pain in a patient in need thereof comprising administration of an effective amount of the composition of claim 1 to the patient in need thereof.
7. A composition comprising a mono-maleate salt of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine, wherein the composition is substantially free of (S)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine.
8. The composition of claim 7 , wherein the salt is in crystalline form.
9. The composition of claim 8 , wherein the crystalline form is characterized by a powder x-ray diffraction pattern comprising at least one of the following peaks:
2θ
12.81 ± 0.1°
16.09 ± 0.1°
18.00 ± 0.1°
19.07 ± 0.1°
24.49 ± 0.1°
26.40 ± 0.1°
26.04 ± 0.1°
27.88 ± 0.1°.
10. The composition of claim 8 , wherein the crystalline form is characterized by an XRPD pattern that substantially corresponds to that shown in FIG. 7 .
11. The composition of claim 8 , wherein the crystalline form is characterized by a powder x-ray diffraction pattern comprising at least one of the following peaks:
2θ
4.31 ± 0.1°
16.56 ± 0.1°
18.29 ± 0.1°
18.78 ± 0.1°
19.64 ± 0.1°
20.27 ± 0.1°
21.02 ± 0.1°
21.46 ± 0.1°
21.90 ± 0.1°
22.43 ± 0.1°
22.86 ± 0.1°
25.40 ± 0.1°
25.73 ± 0.1°
26.15 ± 0.1°
26.56 ± 0.1°
27.40 ± 0.1°
28.59 ± 0.1°
29.57 ± 0.1°.
12. The composition of claim 8 , wherein the crystalline form is characterized by an XRPD pattern that substantially corresponds to that shown in FIG. 8 .
13. A pharmaceutical composition comprising the composition of claim 7 and at least one pharmaceutically acceptable carrier, diluent, or excipient.
14. A method of treating pain in a patient in need thereof comprising administration of an effective amount of the composition of claim 7 to the patient in need thereof.