IP Library Granted Patent US 9,241,924
Granted Patent B2
US 9,241,924 · App. 13/165,651 · Granted Jan 26, 2016

Compositions of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine

Inventors: Charles A. McWherter (Hayward, CA); Robert Louis Martin (Hayward, CA); David B. Karpf (Monte Sereno, CA); Brian K. Roberts (Hayward, CA); Douglas Alan Lorenz (Bend, OR); Rodney James Ketner (Bend, OR)
Assignee: CYMABAY THERAPEUTICS, INC.
A61K31/397A61K9/1652A61K9/2054A61K31/506A61K9/1635A61K9/1641A61K9/2018
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Quick Facts
Patent No.
US 9,241,924
App. No.
13/165,651
Granted
Jan 26, 2016
Kind
B2
Abstract

This invention relates to the field of pharmaceutical chemistry and, more specifically, to pharmaceutical formulations as well as to intermediates used to prepare such formulations and to methods for manufacturing such formulations.

Claims (13)

1. A solid dispersion consisting of from about 10% to about 50% by weight of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine free base and a water soluble, biologically compatible polymer, wherein from about 25% to about 100% by weight of the 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine is non-crystalline, and wherein the water soluble, biologically compatible polymer is cellulose acetate phthalate.

2. The solid dispersion of claim 1 , wherein from about 50% to about 100% by weight of the 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine is non-crystalline.

3. The solid dispersion of claim 2 , wherein from about 75% to about 100% by weight of the 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine is non-crystalline.

4. The solid dispersion of claim 3 , wherein about 95% by weight of the 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine is non-crystalline.

5. The solid dispersion of claim 1 , wherein the smallest diameter of the solid dispersion is from about 1 to about 100 micrometers.

6. The solid dispersion of claim 1 , consisting of from about 20% to about 30% by weight 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine.

7. A solid dispersion, comprising about 25% by weight 5-ethyl-2-{4-[4-(4-tetrazol-1yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine free base and about 75% by weight of cellulose acetate phthalate, wherein from about 25% to about 100% by weight of the 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]piperidin-1-yl}pyrimidine is non-crystalline.

8. The solid dispersion of claim 1 , which is a spray-dried dispersion or a hot-melt extrudate.

9. A pharmaceutical formulation comprising a pharmaceutically inert carrier and a solid dispersion,

the solid dispersion consisting of from about 10% to about 50% by weight of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine free base, and a water soluble, biologically compatible polymer,

wherein from about 25% to about 100% by weight of the 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine is non-crystalline and wherein the water soluble biologically compatible polymer is cellulose acetate phthalate.

10. The pharmaceutical formulation of claim 9 , wherein the solid dispersion, consists of from about 20% to about 30% by weight 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine.

11. A pharmaceutical formulation comprising a pharmaceutically inert carrier and a solid dispersion, wherein the solid dispersion comprises about 25% by weight 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine and about 75% by weight of cellulose acetate phthalate, wherein from about 25% to about 100% by weight of the 5-ethyl-2-{4-[4-(4-tetrazol-1yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine is non-crystalline.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Aug 7, 2015
From: SILICON VALLEY BANK; OXFORD FINANCE LLC
To: CYMABAY THERAPEUTICS, INC.
Reel/Frame 036307/0406 →
SECURITY AGREEMENT Recorded Nov 22, 2013
From: CYMABAY THERAPEUTICS, INC.
To: SILICON VALLEY BANK; OXFORD FINANCE LLC
Reel/Frame 031710/0508 →
CHANGE OF NAME Recorded Oct 22, 2013
From: METABOLEX, INC.
To: CYMABAY THERAPEUTICS, INC.
Reel/Frame 031475/0472 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 7, 2011
From: MCWHERTER, CHARLES A.; MARTIN, ROBERT LOUIS; KARPF, DAVID B.; ROBERTS, BRIAN K.
To: METABOLEX, INC.
Reel/Frame 026868/0988 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 7, 2011
From: LORENZ, DOUGLAS ALAN; KETNER, RODNEY JAMES
To: BEND RESEARCH, INC.
Reel/Frame 026868/0996 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 7, 2011
From: BEND RESEARCH, INC.
To: METABOLEX, INC.
Reel/Frame 026869/0003 →
Continuity (2)
Provisional Application 61357981 · Jun 23, 2010
Related Publication 20110318418A1 · Dec 29, 2011