IP Library Granted Patent US 10,087,193
Granted Patent B2
US 10,087,193 · App. 15/114,991 · Granted Oct 2, 2018

Crystalline forms of dolutegravir sodium

Inventors: Ramakoteswara Rao Jetti (Maharashtra, IN); Satish Beeravelly (Maharashtra, IN); Madhu Murthy Nadella (Maharashtra, IN); Haribabu Nandipati (Maharashtra, IN)
Assignee: Mylan Laboratories Limited
C07D498/14C07B2200/13
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Quick Facts
Patent No.
US 10,087,193
App. No.
15/114,991
Granted
Oct 2, 2018
Kind
B2
Abstract

The present disclosure relates to novel crystalline dolutegravir sodium Form-M2, Form-M3, Form-M4 and process for the preparation thereof.

Claims (18)

1. A crystalline dolutegravir sodium Form-M2, which has a powder X-ray diffraction pattern having 2Θ angle of significant peaks at about 6.23, 7.87, 19.54, 21.34 and 23.84 ±0.2°.

2. The crystalline dolutegravir sodium Form-M2 according to claim 1 which has a powder X-ray diffraction pattern having 2Θ angle of significant peaks at about 6.23, 7.87, 9.80, 12.46, 12.69, 12.88, 15.15, 16.28, 16.94, 17.91, 18.42, 18.74, 19.06, 19.54, 19.75, 20.25, 21.34, 21.82, 23.84, 24.36, 24.81, 25.02, 25.32, 25.51, 26.17, 27.17, 28.14, 28.82, 29.31, 29.75, 31.25, 31.52, 32.05 and 32.82±0.2°.

3. A crystalline dolutegravir sodium Form-M2, which has a powder X-ray diffraction pattern as shown in FIG. 1 .

4. A process for the preparation of crystalline dolutegravir sodium Form-M2 comprising the steps of:

a. dissolving dolutegravir in an organic solvent at elevated temperature;

b. adding alcoholic sodium hydroxide solution; and

c. isolating crystalline dolutegravir sodium Form-M2.

5. The process of claim 4 , wherein organic solvent is a polar protic solvent.

6. The process of claim 5 , wherein the polar protic solvent is selected from the group consisting of methanol, ethanol, isopropanol, 1-butanol, 2-butanol, isoamyl alcohol, isobutyl alcohol, 1-pentanol, 1-propanol, 2-prapanol and mixtures thereof and alcoholic sodium hydroxide is selected from methanolic sodium hydroxide, ethanolic sodium hydroxide, isopropanol sodium hydroxide and mixtures thereof.

7. A crystalline dolutegravir sodium Form-M3, which has a powder X-ray diffraction pattern having 2Θ angle of significant peaks at about 5.91, 13.98, 17.51, 19.63 and 22.31 ±0.2°.

8. A crystalline dolutegravir sodium Form-M3, according to claim 7 which has a powder X-ray diffraction pattern having 2Θ angle of significant peaks at about 5.91, 8.38, 9.32, 13.06, 13.98, 15.02, 16.42, 17.51, 18.03, 18.75, 19.63, 20.73, 21.70, 22.31, 23.52, 25.06, 25.45, 26.19, 26.72, 27.51, 29.45, 31.69, 34.28, 38.36 and 45.56±0.2°.

9. A crystalline dolutegravir sodium Form-M3, which has a powder X-ray diffraction pattern as shown in FIG. 2 .

10. A process for the preparation of crystalline dolutegravir sodium Form-M3 comprising the step of drying dolutegravir sodium Form-M2 under reduced pressure at a temperature of 75-85° C. for 12-15 hours.

11. A crystalline dolutegravir sodium Form-M4, which has a powder X-ray diffraction pattern having 2Θ angle of significant peaks at about 8.10, 18.40, 19.19, 21.23, 21.72 and 24.02 ±0.2°.

12. A crystalline dolutegravir sodium Form-M4, according to claim 11 which has a powder X-ray diffraction pattern having 2Θ angle of significant peaks at about 6.34, 8.10, 11.82, 12.93, 14.43, 15.63, 16.52, 17.46, 18.40, 19.19, 19.41, 20.09, 21.23, 21.72, 22.27, 24.02, 24.90, 25.65, 27.59, 28.44, 29.70, 30.81, 34.11, 35.54, 38.36 and 46.35±0.2°.

13. A crystalline dolutegravir sodium Form-M4, which has a powder X-ray diffraction pattern as shown in FIG. 3 .

14. A process for the preparation of crystalline dolutegravir sodium Form-M4 comprising the step of drying dolutegravir sodium Form-M3 or Form-M2 under reduced pressure at a temperature of 70-140° C. for 15-48 hours.

15. A process for the preparation of crystalline dolutegravir sodium Form-M4 comprising the step of drying dolutegravir sodium Form-M3 or Form-M2 at a temperature of 190-210° C. for 15-20 minutes.

Assignments (3)
CHANGE OF NAME Recorded Jan 12, 2026
From: TIANISH LABORATORIES PRIVATE LIMITED
To: MATRIX PHARMACORP PRIVATE LIMITED
Reel/Frame 074322/0525 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2024
From: MYLAN LABORATORIES LIMITED
To: TIANISH LABORATORIES PRIVATE LIMITED
Reel/Frame 068861/0150 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 17, 2017
From: JETTI, RAMAKOTESWARA RAO; BEERAVELLY, SATISH; NADELLA, MADHU MURTHY; NANDIPATI, HARIBABU
To: MYLAN LABORATORIES LIMITED
Reel/Frame 041284/0341 →
Priority Claims (1)
IN 455/MUM/2014 · Feb 7, 2014 · national
Continuity (1)
Related Publication 20160347766A1 · Dec 1, 2016