# US 12,594,266 B2 · Triterpenoid antifungals for the treatment or prevention of Pneumocystis spp. pneumonia

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- Number: US 12,594,266 B2
- Document ID: US12594266B2
- Status: Granted
- Kind: B2
- Application number: 17/432,926
- Filed: 2020-02-25
- Published: 2023-05-18
- Granted: 2026-04-07
- Earliest claimed: 2019-02-27
- Assignees: Scynexis, Inc.
- Applicants: Scynexis, Inc.
- Inventors: David A. Angulo Gonzalez; Stephen Andrew Barat
- Web page: https://patentgrep.com/patent/US12594266B2

## CPC

- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 31/10: Antimycotics
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Eufumafungin derivative triterpenoid antifungal compounds are used to treat and/or prevent Pneumocystis pneumonia (PCP) due to their unexpected efficacy against Pneumocystis spp. including their ability to reduce the lung burden of cyst and trophic forms of this fungi. The enfumafungin derivative triterpenoids (or pharmaceutically acceptable salts or hydrates thereof) are inhibitors of (1,3)-β-D-glucan synthesis and are useful in the treatment and/or prevention of PCP since they demonstrate potent activity against Pneumocystis spp. in in vivo models, exhibit adequate tissue penetration into lungs, and are well tolerated.

## Claims

### Claim 1

A method of treating Pneumocystis pneumonia in a subject in need thereof, the method comprising administering to the subject a compound of Formula (II):
which is (1S,4aR,6aS,7R,8R, 10aR, 10bR, 12aR, 14R, 15R)-15-[[2-amino-2,3,3-trimethylbutyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-14-[5-(4-pyridinyl)-1H-1,2,4-triazol-1-yl]-1,6,6a,7,8,9,10,10a, 10b, 11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-4H-1,4a-propano-2H-phenanthro [1,2-c]pyran-7-carboxylic acid,
or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the Pneumocystis pneumonia is caused by Pneumocystis jirovecii.

### Claim 3 (depends on 2)

The method according to claim 2, wherein cyst burden and trophic burden of Pneumocystis jirovecii are reduced.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the compound or the pharmaceutically acceptable salt or hydrate thereof is administered orally.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the compound or the pharmaceutically acceptable salt or hydrate thereof is administered intravenously.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the subject is human.

### Claim 7

A method of treating Pneumocystis jirovecii pneumonia in a human in need thereof, the method comprising administering to the human a compound of Formula (IIa):
which is (1S,4aR,6aS,7R,8R, 10aR, 10bR, 12aR, 14R, 15R)-15-[[(2R)-2-amino-2,3,3-trimethylbutyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-14-[5-(4-pyridinyl)-1H-1,2,4-triazol-1-yl]-1,6,6a,7,8,9,10,10a, 10b, 11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-4H-1,4a-propano-2H-phenanthro [1,2-c]pyran-7-carboxylic acid,
or a pharmaceutically acceptable salt or hydrate thereof.

### Claim 8 (depends on 7)

The method according to claim 7, wherein cyst burden and trophic burden of Pneumocystis jirovecii are reduced.

### Claim 9 (depends on 7)

The method according to claim 7, wherein the compound or the pharmaceutically acceptable salt or hydrate thereof is administered orally.

### Claim 10 (depends on 7)

The method according to claim 7, wherein the compound or the pharmaceutically acceptable salt or hydrate thereof is administered intravenously.

### Claim 11 (depends on 7)

The method according to claim 7, wherein the citrate salt of the compound of Formula (IIa) is administered.

### Claim 12 (depends on 7)

The method according to claim 7, wherein the pharmaceutically acceptable salt of the compound of Formula (IIa) is administered orally in a tablet.

### Claim 13 (depends on 7)

The method according to claim 7, wherein the compound or the pharmaceutically acceptable salt or hydrate thereof is administered orally and provides a total daily dose of from 250 mg to 1000 mg of the compound.

### Claim 14 (depends on 13)

The method according to claim 13, wherein the compound or the pharmaceutically acceptable salt or hydrate thereof is administered for 2 to 6 weeks.

### Claim 15

A method of treating Pneumocystis jirovecii pneumonia in a human in need thereof, the method comprising administering to the human a pharmaceutically acceptable salt of the compound of Formula (IIa):
which is (1S,4aR,6aS,7R,8R,10aR, 10bR, 12aR,14R, 15R)-15-[[(2R)-2-amino-2,3,3-trimethylbutyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-14-[5-(4-pyridinyl)-1H-1,2,4-triazol-1-yl]-1,6,6a,7,8,9,10,10a, 10b, 11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-4H-1,4a-propano-2H-phenanthro [1,2-c]pyran-7-carboxylic acid.

### Claim 16 (depends on 15)

The method according to claim 15, wherein the citrate salt of the compound of formula (IIa) is administered.