IP Library Granted Patent US 10,000,465
Granted Patent B2
US 10,000,465 · App. 15/126,412 · Granted Jun 19, 2018

Antifungal compound process

Inventors: William J. Hoekstra (Durham, NC); Christopher M. Yates (Raleigh, NC); Mark Behnke (Poolesville, MD); Asaf Alimardanov (North Bethesda, MD); Scott A. David (Huntsburg, OH); Douglas Franklin Fry (Euclid, OH)
Assignees: Mycovia Pharmaceuticals, Inc.; U.S. Department of Health and Human Services
C07D401/06C07B57/00C07D213/57C07F7/1856C07B2200/07
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Quick Facts
Patent No.
US 10,000,465
App. No.
15/126,412
Granted
Jun 19, 2018
Kind
B2
Abstract

The present invention relates to a process for preparing compound 1 that is useful as an antifungal agent. In particular, the invention seeks to provide new methodology for preparing compound 1 and substituted derivatives thereof.

Claims (14)

1. A process to prepare amino-alcohol 1-6 or 1-7,

or a mixture thereof, the method comprising:

(i) forming the trimethylsilyl-cyanohydrin of aryl-pyridine 1-4,

 to provide trimethylsilyl-cyanohydrin 1-5 or 1-5a,

 or a mixture thereof; and

(ii) reducing trimethylsilyl-cyanohydrin 1-5 or 1-5a,

 or a mixture thereof, to provide amino-alcohol 1-6 or 1-7,

 or a mixture thereof;

wherein forming the trimethylsilyl-cyanohydrin is performed in the presence of a chiral catalyst.

2. The process of claim 1 , further comprising enriching the enantiomeric purity of amino-alcohol 1-6 or 1-7, the process comprising:

(i) crystallizing amino-alcohol 1-6 or 1-7 with a chiral acid in a suitable solvent or solvent mixture, wherein:

the suitable solvent or solvent mixture is selected from acetonitrile, isopropanol, ethanol, water, methanol, or combinations thereof;

(ii) isolating the enantio-enriched 1-6 or 1-7; and

(iii) free-basing the enantio-enriched chiral salt mixture to afford enantio-enriched amino-alcohol 1-6* or 1-7*,

Assignments (6)
CHANGE OF NAME Recorded Mar 28, 2018
From: VIAMET PHARMACEUTICALS (NC), INC.
To: MYCOVIA PHARMACEUTICALS, INC.
Reel/Frame 045759/0728 →
CHANGE OF NAME Recorded Jan 2, 2018
From: VIAMET PHARMACEUTICALS, INC.
To: VIAMET PHARMACEUTICALS (NC), INC.
Reel/Frame 044978/0893 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2017
From: HOEKSTRA, WILLIAM J.; YATES, CHRISTOPHER M.
To: VIAMET PHARMACEUTICALS, INC.
Reel/Frame 040871/0877 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2017
From: RICERA BIOSCIENCES, LLC
To: UNITED STATES DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 040861/0900 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2017
From: FRY, DOUGLAS F.; DAVID, SCOTT A.
To: RICERA BIOSCIENCES, LLC
Reel/Frame 041268/0072 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2017
From: ALIMARDANOV, ASAF R.; BEHNKE, MARK L.
To: UNITED STATES DEPARTMENT OF HEALTH AND HUMAN SERVICES
Reel/Frame 041268/0155 →
Continuity (2)
Provisional Application 61955633 · Mar 19, 2014
Related Publication 20170088540A1 · Mar 30, 2017