IP Library Granted Patent US 10,407,392
Granted Patent B2
US 10,407,392 · App. 16/280,527 · Granted Sep 10, 2019

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.; The United States of America, as represented by the Secretary, Department of Health and Human Services
C07D213/50C07D213/30C07D213/38C07D401/06C07D405/06
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Quick Facts
Patent No.
US 10,407,392
App. No.
16/280,527
Granted
Sep 10, 2019
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 (20)

1. A compound of formula XI:

each R 4 is independently H or halo;

o is 1, 2, or 3

each R 5 is independently H or fluoro;

each R 6 is independently H or fluoro;

each R 11 is independently halo or

and

each R 12 is independently H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, or optionally substituted hetrocyclyl.

2. The compound of claim 1 , wherein the compound has the following formula:

wherein each R 1 is independently, halo or

3. A process to prepare compound 2-5,

comprising:

(i) reacting ester 6,

with morpholine to provide morpholine amide 7:

(ii) reacting morpholine amide 7:

to provide ketone 3,

(iii) performing olefination of ketone 3,

to provide olefin 2-5,

wherein M is Mg or MgX; and X is halogen; and

each R 1 is independently, halo or

Continuity (3)
Division 15126392
Provisional Application 61955599 · Mar 19, 2014
Related Publication 20190185429A1 · Jun 20, 2019