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Claims for Patent: 7,919,598

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Claims for Patent: 7,919,598

Title:Crystal structures of SGLT2 inhibitors and processes for preparing same
Abstract: The present invention relates to physical crystal structures of a compound of the formula I: ##STR00001## wherein R.sup.1, R.sup.2, R.sup.2a, R.sup.3 and R.sup.4 are as defined herein, especially ##STR00002## pharmaceutical compositions containing structures of compound I or II, processes for preparing same, intermediates used in preparing same, and methods of treating diseases such as diabetes using such structures.
Inventor(s): Gougoutas; Jack Z. (Princeton, NJ), Lobinger; Hildegard (Regensburg, DE), Ramakrishnan; Srividya (Milltown, NJ), Deshpande; Prashant P. (Princeton, NJ), Bien; Jeffrey T. (Princeton, NJ), Lai; Chiajen (Kendall Park, NJ), Wang; Chenchi (Somerset, NJ), Riebel; Peter (Ruhstorf a.d. Rott, DE), Grosso; John Anthony (Princeton Junction, NJ), Nirschl; Alexandra A. (Yardley, PA), Singh; Janak (Lawrenceville, NJ), DiMarco; John D. (East Brunswick, NJ)
Assignee: Bristol-Myers Squibb Company (Princeton, NJ)
Application Number:11/765,481
Patent Claims: 1. A crystalline (S)-propylene glycol ((S)-PG) solvate compound Ia (form SC-3) ##STR00066##

2. The crystalline (S)-PG compound Ia (form SC-3) according to claim 1 characterized by unit cell parameters substantially equal to the following: Cell dimensions: a=11.2688(8) .ANG. b=4.8093(3) .ANG. c=46.723(3) .ANG. .alpha.=90 degrees .beta.=90 degrees .gamma.=90 degrees Space group=P2.sub.12.sub.12.sub.1 Molecules/asymmetric unit=1 wherein measurement of said crystalline structure is at room temperature and characterized by fractional atomic coordinates substantially as listed in Table 4.

3. The crystalline compound of claim 1 wherein said compound is in substantially pure form.

4. The crystalline (S)-PG compound Ia (form SC-3) according to claim 1 characterized by peaks in the powder x-ray diffraction pattern at 2.theta. values of 3.8.+-.0.1, 7.6.+-.0.1, 8.1.+-.0.1, 8.7.+-.0.1, 15.2.+-.0.1, 15.7.+-.0.1, 17.1.+-.0.1, 18.9.+-.0.1 and 20.1.+-.0.1.

5. The crystalline (S)-PG compound Ia (form SC-3) according to claim 1 characterized by a solid state .sup.13C NMR spectrum having substantially similar peak positions at 16.2, 17.6, 39.3, 60.9, 63.3, 69.8, 76.9, 78.7, 79.4, 113.8, 123.6, 129.3, 130.5, 132.0, 135.7, 139.1 and 158.0 ppm.

6. The crystalline (S)-PG compound Ia (form SC-3) according to claim 1 characterized by a differential scanning calorimetry thermogram having an endotherm in the range of about 50.degree. C. to about 78.degree. C. or as shown in FIG. 7.

7. The crystalline (S)-PG compound Ia (form SC-3) according to claim 1 characterized by a thermal gravimetric analysis curve with about 18.7% weight loss from about room temperature up to about 240.degree. C. or as shown in FIG. 5.

8. A process of preparing crystalline compound Ia (form SC-3) ##STR00067## comprising: treating compound A ##STR00068## in an organic solvent with base and (S)-propylene glycol, optionally adding seeds of (S)-PG crystalline compound Ia (form SC-3), to provide (S)-PG crystalline compound Ia (form SC-3).

9. The process according to claim 8 wherein seeds of (S)-PG crystalline compound Ia (form SC-3) are added to the reaction mixture.

10. A process for preparing a crystalline compound Ia (form SC-3), which comprises treating compound B ##STR00069## with a reducing agent in the presence of an activating group to provide compound I ##STR00070## treating compound I with (S)-propylene glycol, optionally adding seeds of crystalline compound Ia (form SC-3) to the reaction mixture, in the presence of an organic solvent to provide crystalline compound Ia (form SC-3) ##STR00071##

11. The process according to claim 10 wherein the reducing agent is an alkylsilyl hydride and the activating group is a Lewis acid.

12. The process according to claim 10 wherein the reducing agent is triethylsilane and the activating group is BF.sub.3OEt.sub.2 or BF.sub.3.2CH.sub.3COOH.

13. A process of preparing crystalline compound Ia (form SC-3) ##STR00072## which comprises treating compound If ##STR00073## with acetic anhydride in the presence of dimethylaminopyridine CH.sub.3CN to provide compound B' ##STR00074## treating compound B' with a reducing agent in the presence of an activating group and CH.sub.3CN to provide intermediate A ##STR00075## treating intermediate A with a base and then with (S)-propylene glycol, optionally adding seeds of crystalline compound Ia (form SC-3) to the reaction mixture, in the presence of an organic solvent to provide crystalline compound Ia (form SC-3) ##STR00076##

14. The process according to claim 13 wherein the reducing agent is an alkylsilyl hydride and the activating group is a Lewis acid.

15. The process according to claim 13 wherein the reducing agent is triethylsilane and the activating group is BF.sub.3OEt.sub.2 or BF.sub.3.2CH.sub.3COOH.
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