# US 10,308,632 B2 · Antifungal compounds and processes for making

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- Number: US 10,308,632 B2
- Document ID: US10308632B2
- Status: Granted
- Kind: B2
- Application number: 15/760,917
- Filed: 2016-09-16
- Published: 2018-09-20
- Granted: 2019-06-04
- Earliest claimed: 2015-09-18
- Assignees: VPS-3, Inc.
- Applicants: VPS-3, Inc.
- Inventors: David Dale Wirth; Christopher M. Yates
- Web page: https://patentgrep.com/patent/US10308632B2

## CPC

- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- A01N 43/713: having rings with four or more nitrogen atoms as the only ring hetero atoms
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 13/00: Drugs for disorders of the urinary system
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/10: Antimycotics
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- B01J 31/0244: {with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine}
- C07B 53/00: Asymmetric syntheses
- C07B 57/00: Separation of optically-active compounds
- C07B 63/02: by treatment giving rise to a chemical modification
- C07C 303/44: Separation; Purification
- C07C 309/30: of six-membered aromatic rings substituted by alkyl groups
- C07D 213/30: Oxygen atoms
- C07D 453/02: containing not further condensed quinuclidine ring systems
- B01J 2231/341: 1,2-additions, e.g. aldol or Knoevenagel condensations
- C07B 2200/07: Optical isomers
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Provided are polymorphic forms of compound 5 or 5*, or mixtures thereof, and polymorph forms of compound 14 or 14*, or mixtures thereof. Also provided are methods of preparing compound 5 or 5*, or mixtures thereof, and methods of preparing compound of 14 or 14*, or mixtures thereof, which are useful as antifungal agents. In particular, provided is new methodology for preparing polymorphs of the compounds described and substituted derivatives thereof.

## Claims

### Claim 1

A polymorph of a compound of formula 5,
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. 8;
or
(ii) a DSC thermogram showing an endotherm at about 65-85° C.

### Claim 2 (depends on 1)

The polymorph of claim 1, characterized by a powdered X-ray diffraction pattern having peaks expressed in degrees 2-theta±0.2° at each of about 10.9, 14.0, 15.9, 19.7, and 23.2.

### Claim 3 (depends on 1)

The polymorph of claim 1, wherein the polymorph has less than 1.0% water therein.