# US 10,370,353 B2 · Antifungal compounds and processes for making

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- Number: US 10,370,353 B2
- Document ID: US10370353B2
- Status: Granted
- Kind: B2
- Application number: 15/835,991
- Filed: 2017-12-08
- Published: 2018-11-08
- Granted: 2019-08-06
- Earliest claimed: 2015-03-19
- Assignees: Mycovia Pharmaceuticals, Inc.
- Applicants: Mycovia Pharmaceuticals, Inc.
- Inventors: William J. Hoekstra; David Dale Wirth; Tracy Ehiwe; Thierry Bonnaud
- Web page: https://patentgrep.com/patent/US10370353B2

## CPC

- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 31/10: Antimycotics
- C07B 63/04: Use of additives {(anti-oxidant compositions or compositions inhibiting chemical change in general C09K15/00)}
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention relates to polymorphic forms of compound 1 or 1a and processes for preparing compound 1 and 1a polymorphs, which are useful as antifungal agents. In particular, the invention seeks to provide a new methodology for preparing polymorphs of compound 1 and substituted derivatives thereof.

## Claims

### Claim 1

A 1.5 hydrate polymorph of a compound of formula 1,
characterized by at least one of:
(i) a powdered X-ray diffraction pattern having two or more peaks expressed in degrees 2-theta±0.2° and selected from peaks delineated in the pattern of FIG. 5; or
(ii) a DSC thermogram showing an endotherm at about 85° C.

### Claim 2

A process to prepare a 1.5 hydrate polymorph of compound 1:
comprising suspending a compound of formula 1 in a solvent and isolating any solid material.

### Claim 3 (depends on 1)

The compound of claim 1, characterized by a powdered X-ray diffraction pattern having peaks expressed in degrees 2-theta±0.2° at each of about 7.9, 8.9, 16.2, 22.6, 24.2, 26.6, 28.0.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound is essentially solvent free.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound has 0.1-0.5% weight solvent.

### Claim 6 (depends on 2)

The process of claim 2, wherein the compound suspended in the solvent is in one of an amorphous, solvate, or hydrate form.

### Claim 7 (depends on 2)

The process of claim 2, wherein the solvent is an organic solvent.

### Claim 8 (depends on 2)

The process of claim 2, wherein the solvent is a C3-C10 alcohol.

### Claim 9 (depends on 2)

The process of claim 2, comprising two or more solvents.

### Claim 10 (depends on 2)

The process of claim 2, wherein one solvent is a C3-C10 alcohol and one solvent is water.

### Claim 11 (depends on 2)

The process of claim 2, wherein the isolated solid material is dried at a temperature of 30-60° C.