IP Library Granted Patent US 9,757,406
Granted Patent B2
US 9,757,406 · App. 15/282,128 · Granted Sep 12, 2017

Combination formulation of two antiviral compounds

Inventors: Eric Gorman (Foster City, CA); Erik Mogalian (Foster City, CA); Reza Oliyai (Foster City, CA); Dimitrios Stefanidis (Mountain View, CA); Lauren Wiser (San Francisco, CA); Vahid Zia (Palo Alto, CA)
Assignee: Gilead Pharmasset LLC
A61K31/7072A61K31/4188
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Quick Facts
Patent No.
US 9,757,406
App. No.
15/282,128
Granted
Sep 12, 2017
Kind
B2
Abstract

Disclosed are pharmaceutical compositions comprising Compound I, having the formula: and an effective amount of sofosbuvir wherein the sofosbuvir is substantially crystalline. Also disclosed are methods of use for the pharmaceutical composition.

Claims (31)

1. A pharmaceutical composition comprising:

a) from about 1% to about 25% w/w of a solid dispersion comprising Compound I dispersed within a polymer matrix formed by copovidone, wherein the weight ratio of Compound I to copovidone in the solid dispersion is about 1:1 and wherein Compound I is substantially amorphous having the formula:

b) from about 35% to about 45% w/w of substantially crystalline sofosbuvir having the formula:

c) from about 30% to about 40% w/w of microcrystalline cellulose;

d) from about 1% to about 5% w/w of croscarmellose sodium; and

e) from about 0.5% to about 2.5% w/w of magnesium stearate.

2. The pharmaceutical composition of claim 1 , wherein the crystalline sofosbuvir has XRPD 2θ-reflections at about: 6.1 and 12.7 °2θ±0.2.

3. The pharmaceutical composition of claim 1 , wherein the crystalline sofosbuvir has XRPD 2θ-reflections at about: 6.1, 20.1, and 20.8 °2θ±0.2.

4. The pharmaceutical composition of claim 1 , comprising about 40% w/w of sofosbuvir.

5. The pharmaceutical composition of claim 1 , comprising about 20% w/w of the solid dispersion.

6. The pharmaceutical composition of claim 1 , comprising about 35.5% w/w of microcrystalline cellulose.

7. The pharmaceutical composition of claim 1 , comprising about 3% w/w of croscarmellose sodium.

8. The pharmaceutical composition of claim 1 , comprising about 1.5% w/w of magnesium stearate.

9. A pharmaceutical composition comprising:

a) about 20% w/w of a solid dispersion comprising Compound I dispersed within a polymer matrix formed by copovidone, wherein the weight ratio of Compound I to copovidone in the solid dispersion is about 1:1 and wherein Compound I is substantially amorphous having the formula:

b) about 40% w/w of substantially crystalline sofosbuvir having the formula:

c) about 35.5% w/w of microcrystalline cellulose;

d) about 3% w/w of croscarmellose sodium; and

e) about 1.5% w/w of magnesium stearate.

10. The pharmaceutical composition of claim 9 , wherein the crystalline sofosbuvir has XRPD 2θ-reflections at about: 6.1 and 12.7 °2θ±0.2.

11. The pharmaceutical composition of claim 9 , wherein the crystalline sofosbuvir has XRPD 2θ-reflections at about: 6.1, 20.1, and 20.8 °2θ±0.2.

12. A pharmaceutical composition comprising:

a) about 200 mg of a solid dispersion comprising Compound I dispersed within a polymer matrix formed by copovidone, wherein the weight ratio of Compound I to copovidone in the solid dispersion is about 1:1 and wherein Compound I is substantially amorphous having the formula:

b) about 400 mg of substantially crystalline sofosbuvir having the formula:

c) about 355 mg of microcrystalline cellulose;

d) about 30 mg of croscarmellose sodium; and

e) about 15 mg of magnesium stearate.

13. The pharmaceutical composition of claim 12 which is in the form of a tablet comprising a film coating.

14. The tablet of claim 13 , wherein the film coating is a polyvinylalcohol-based coating.

15. The pharmaceutical composition of claim 12 , wherein the crystalline sofosbuvir has XRPD 2θ-reflections at about: 6.1 and 12.7 °2θ±0.2.

16. The pharmaceutical composition of claim 12 , wherein the crystalline sofosbuvir has XRPD 2θ-reflections at about: 6.1, 20.1, and 20.8 °2θ±0.2.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 30, 2022
From: GILEAD PHARMASSET LLC
To: GILEAD SCIENCES, INC.
Reel/Frame 060219/0085 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2017
From: GORMAN, ERIC; MOGALIAN, ERIK; OLIYAI, REZA; STEFANIDIS, DIMITRIOS; WISER, LAUREN; ZIA, VAHID
To: GILEAD PHARMASSET LLC
Reel/Frame 041987/0225 →
Continuity (5)
Continuation 14168340 · Jan 30, 2014
Provisional Application 61870712 · Aug 27, 2013
Provisional Application 61898690 · Nov 1, 2013
Provisional Application 61907308 · Nov 21, 2013
Related Publication 20170095499A1 · Apr 6, 2017