IP Library › Granted Patent US 10,745,378
Granted Patent B2
US 10,745,378 · App. 16/253,909 · Granted Aug 18, 2020

Antifungal compound process

Inventors: William J. Hoekstra (Durham, NC); Christopher M. Yates (Raleigh, NC)
Assignee: Mycovia Pharmaceuticals, Inc.
C07D401/06A61K31/4439A61K45/06C07D213/30C07D213/50C07D257/04C07D403/06
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Quick Facts
Patent No.
US 10,745,378
App. No.
16/253,909
Granted
Aug 18, 2020
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 (59)

1. A process for preparing compound 1 or 1a, or a mixture thereof:

comprising:

i. arylating a compound of formula 15,

to provide ketone 16,

ii. forming the cyanohydrin of ketone 16,

to provide nitrile 24 or 24a,

or a mixture thereof;

iii. reducing nitrile 24 or 24a,

or a mixture thereof, to provide amino-alcohol 20 or 20a,

or a mixture thereof; and

iv. forming the tetrazole of amino-alcohol 20 or 20a,

or a mixture thereof, to provide compound 1 or 1a,

or a mixture thereof;

wherein R is halo; and R′ is H or TMS.

2. A process for preparing compound 1 or 1a, or a mixture thereof:

comprising:

i. cyanating a compound of formula 15,

to provide a compound of formula 23 or 23a,

or a mixture thereof;

ii. arylating a compound of formula 23 or 23a,

or a mixture thereof, to provide nitrile 24 or 24a,

or a mixture thereof;

iii. reducing nitrile 24 or 24a,

or a mixture thereof, to provide amino-alcohol 20 or 20a,

or a mixture thereof;

iv. forming the tetrazole of amino-alcohol 20 or 20a,

or a mixture thereof, to provide compound 1 or 1a,

or a mixture thereof;

wherein R is halo; and R′ is H or TMS.

3. A process for preparing compound 1 or 1a, or a mixture thereof:

comprising:

i. cyanating a compound of formula 15,

to provide a compound of formula 23 or 23a,

or a mixture thereof;

ii. reducing a compound of formula 23 or 23a,

or a mixture thereof, to provide a compound of formula 19 or 19a,

or a mixture thereof;

iii. arylating a compound of formula 19 or 19a,

or a mixture thereof, to provide amino-alcohol 20 or 20a,

or a mixture thereof;

iv. forming the tetrazole of amino-alcohol 20 or 20a,

or a mixture thereof, to provide compound 1 or 1a,

or a mixture thereof;

wherein R is halo; and R′ is H or TMS.

4. A process for preparing compound 1 or 1a, or a mixture thereof:

comprising:

i. cyanating a compound of formula 15,

to provide a compound of formula 23 or 23a,

or a mixture thereof;

ii. reducing a compound of formula 23 or 23a,

or a mixture thereof, to provide a compound of formula 19 or 19a,

or a mixture thereof;

iii forming the tetrazole of a compound of formula 19 or 19a,

or a mixture thereof, to provide a compound of formula 9 or 9a,

or a mixture thereof;

iv. arylating the tetrazole of a compound of formula 9 or 9a,

or a mixture thereof, to provide compound 1 or 1a,

or a mixture thereof;

wherein R is halo; and R′ is H or TMS.

Continuity (3)
Division 15126336
Provisional Application 61955565 · Mar 19, 2014
Related Publication 20190161470A1 · May 30, 2019