IP Library › Granted Patent US 9,802,926
Granted Patent B2
US 9,802,926 · App. 14/916,373 · Granted Oct 31, 2017

Anhydrous crystalline free base form of 6-{2-[1 -(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy}-3-ethoxy-1,2-benzisoxazole

Inventors: Edward Lee (Alpharetta, GA); David McAllister (Notting Hill, AU); Andrew Trigwell (Notting Hill, AU); Robert Vincent Tuohy, III (Norristown, PA); Peter Snyder, Jr. (Norristown, PA); Christa Leisa Frassetto (Norristown, PA)
Assignee: AVIRAGEN THERAPEUTICS, INC.
C07D413/14A61K9/0095A61K9/10A61K9/1617A61K9/1641A61K9/1652A61K9/20A61K9/2013A61K9/2018A61K9/2054A61K9/2059A61K9/284A61K9/4858A61K31/501A61K47/10A61K47/12A61K47/14A61K47/26A61K47/36A61K47/38
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Quick Facts
Patent No.
US 9,802,926
App. No.
14/916,373
Granted
Oct 31, 2017
Kind
B2
Abstract

A crystalline form of 6-{2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy}-3-ethoxy-1,2-benzoxazole is provided which is useful in the treatment of infections caused by Picornaviridae such as human rhinovirus (HRV), and in particular the crystal form is an anhydrous crystalline free base form of 6-{2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy}-3-ethoxy-1,2-benzoxazole. In addition, a method of manufacturing the free base crystalline form is also provided, including a step of micronizing the compound particles, optionally using a wetting agent, as well as pharmaceutical compositions incorporating the free base crystalline form such as tablets or suspensions, and methods of therapeutic treatments using this form and pharmaceutical compositions thereof.

Claims (7)

1. A compound comprising an anhydrous crystalline free base form of 6-{2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy}-3-ethoxy-1,2-benzoxazole, wherein the crystalline free base form has a needle-like crystal habit.

2. The compound of claim 1 , wherein the crystalline form has XRPD peaks (d-space, A) selected from the group consisting of approximately the following values: 19.5, 8.0, 6.5, 4.4, 4.3, 4.0, 3.8, 3.6, and 3.5.

3. The compound of claim 1 , wherein the crystalline form XRPD peaks (2θ) selected from the group consisting of the following approximate values: 4.5, 11.0, 13.6, 20.3, 20.6, 22.1, 23.1, 24.5, and 25.7.

4. The compound of claim 1 , wherein the crystalline form has XRPD peaks (d-space, Å) selected from the group consisting of approximately the following values: 19.2, 8.5, 8.0, 6.5, 5.5, 5.3, 5.0, 4.35, 4.27, 4.12, 4.03, 3.99, 3.96, 3.80 and 3.60.

5. The compound of claim 1 , wherein the crystalline form XRPD peaks (2θ) selected from the group consisting of the following approximate values: 4.6, 11.1, 13.7, 16.1, 20.4, 20.8, 22.3, and 24.8.

6. The compound of claim 1 , wherein the crystalline form has XRPD peaks (2θ) selected from the group consisting of the following approximate values: 4.6, 10.4, 11.1, 13.7, 16.1, 16.7, 17.8, 20.4, 20.8, 21.6, 22.1, 22.3, 22.4, 23.4, and 24.8.

7. The compound of claim 1 , wherein the crystalline form has the XRPD pattern shown in FIG. 1A, 1B, 2A, 2B or 3 .

Assignments (2)
CHANGE OF NAME Recorded Apr 30, 2018
From: AVIRAGEN THERAPEUTICS, INC.
To: VAXART, INC.
Reel/Frame 045673/0079 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2017
From: LEE, EDWARD; MCALLISTER, DAVID; TRIGWELL, ANDREW; TUOHY III, ROBERT VINCENT; SNYDER, JR., PETER; FRASSETTO, CHRISTA LEISA
To: AVIRAGEN THERAPEUTICS, INC.
Reel/Frame 043104/0803 →
Continuity (2)
Provisional Application 62015126 · Jun 20, 2014
Related Publication 20160194310A1 · Jul 7, 2016