# US 7,608,604 B2 · Antiparasitic agents

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- Number: US 7,608,604 B2
- Document ID: US7608604B2
- Status: Granted
- Kind: B2
- Application number: 12/028,192
- Filed: 2008-02-08
- Published: 2008-08-14
- Granted: 2009-10-27
- Earliest claimed: 2007-02-09
- Assignees: Pfizer Inc.
- Inventors: Stuart Nicholas Comlay; Joanne Clare Hannam; William Howson; Christelle Lauret; Yogesh Anil Sabnis
- Web page: https://patentgrep.com/patent/US7608604B2

## CPC

- C07C 381/00: Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- A01N 41/12: not containing sulfur-to-oxygen bonds, e.g. polysulfides
- A61P 33/00: Antiparasitic agents
- A61P 33/10: Anthelmintics
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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

## Abstract

The present invention relates to compounds of the formula (I) or a tautomer or prodrug thereof, or a pharmaceutically acceptable salt of said compound, tautomer or prodrug, wherein: R1, R2, R3, R4 and R5 are each independently selected from H, halo, CN, CF3 and CONH2; compositions containing such compounds and the uses of such compounds as antiparasitic agents.

## Claims

### Claim 1

A compound of the formula
or a pharmaceutically acceptable salt of said compound, wherein:
R1, R2, R3, R4 and R5 are each independently selected from H, halo, CN, CF3 and CONH2.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein R1, R2, R3, R4 and R5 are each independently selected from H, F, Cl, Br, CN and CF3.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein at least one of R1, R2, R3, R4 and R5 is CN and at least two of R1, R2, R3, R4 and R5 are H.

### Claim 4 (depends on 2)

A compound according to claim 2 wherein R1 and R4 are H, one of R2 and R3 is H and the other is CN, and R5 is selected from F, Cl, Br and CF3.

### Claim 5 (depends on 4)

A compound according to claim 4 wherein R3 is CN and R5 is CF3.

### Claim 6 (depends on 1)

A compound according to claim 1 selected from:
N-{1-cyano-2-[5-cyano-2-(trifluoromethyl)phenoxy]-1-methylethyl}-4-pentafluorothiobenzamide,
N-{(1R)-1-cyano-2-[5-cyano-2-(trifluoromethyl)phenoxy]-1-methylethyl}-4-pentafluorothiobenzamide,
N-{(1S)-cyano-2-[5-cyano-2-(trifluoromethyl)phenoxy]-1-methylethyl}-4-pentafluorothiobenzamide,
N-[2-(2-chloro-5-cyanophenoxy)-1-cyano-1-methylethyl]-4-pentafluorothiobenzamide,
N-[2-(2-chloro-5-cyanophenoxy)-(1R)-1-cyano-1-methylethyl]-4-pentafiuorothiobenzamide,
N-[2-(2-chloro-5-cyanophenoxy)-(1S)-1-cyano-1-methylethyl]-4-penrafluorothiobenzamide,
N-{1-cyano-2-[4-cyano-2-(trifluoromethyl)phenoxy]-1-methyl ethyl}-4-pentafluorothiobenzamide,
N-{(1R)1-cyano-2-[4-cyano-2-(trifluoromethyl)phenoxy]-1-methylethyl}-4-pentafluorothiobenzamide,
N-{(1S)1-cyano-2-[4-cyano-2-(trifluoromethyl)phenoxy]-1-methylethyl}-4-pentafluorothiobenzamide,
N-{2-[2-chloro-5-cyano-3-(trifluoromethyl)phenoxy]-1-cyano-1-methylethyl}-4-pentafluorothiobenzamide,
N-{2-[2-chloro-5-cyano-3-(trifluoromethyl)phenoxy]-(1R)-1-cyano-1-methylethyl}-4-pentafluorothiobenzamide,
N-{2-[2-chloro-5-cyano-3-(trifluoromethyl)phenoxy]-(1S)-1-cyano-1-methylethyl}-4-pentafluorothiobenzamide,
N-[2-(2-chloro-4,5-dicyanophenoxy)-1-cyano-1-methylethyl]-4-pentafluorothiobenzamide,
N-[2-(2-chloro-4,5-dicyanophenoxy)-(1R)-1-cyano-1-methylethyl]-4-pentafluorothiobenzamide,
N-[2-(2-chloro-4,5-dicyanophenoxy)-(1S)-1-cyano-1-methylethyl]-4-pentafluorothiobenzamide,
N-{(1-cyano-2-[4-cyano-2-(trifluoromethyl)phenoxy]-1-methylethyl }-4-pentafluorothiobenzamide,
N-{(1R)-1-cyano-2-[4-cyano-2-(trifluoromethyl)phenoxy]-1-methylethyl}-4-pentafluorothiobenzamide, and
N-{(1S)-1-cyano-2-[4-cyano-2-(trifluoromethyl)phenoxy]-1-methylethyl}-4-pentafluorothiobenzamide,
or a pharmaceutically acceptable salt thereof

### Claim 7 (depends on 1)

A pharmaceutical composition comprising a compound of formula (I) of claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

### Claim 8 (depends on 7)

The pharmaceutical composition according to claim 7 further comprising a second therapeutic agent.

### Claim 9 (depends on 8)

The pharmaceutical composition according to claim 8 wherein the second therapeutic agent is selected from ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin, milbemycin oxime, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, closantel, triclabendazole, clorsulon, rafoxanide, niclosamide, praziquantel, epsiprantel, 2-desoxoparaherquamide, tipronil, pyriprole, pyrafluprole, lufenuron, spiromesifen, tebufenozide, spinosad, spinetoram, imidacloprid, dinotefuran, metaflumizone, thibendiamide, chlorantraniliprole, indoxacarb, pyridalyl, pyrimidifen and pyrifluquinazon.

### Claim 10 (depends on 1)

A method of treatment of a parasitic infestation in a host animal, comprising treating said host animal with an effective amount of a compound of formula (I), or with a pharmaceutically acceptable salt or composition thereof, as defined in claim 1.

### Claim 11 (depends on 10)

The method according to claim 10 wherein the host animal is a non-human animal.

### Claim 12 (depends on 10)

The method according to claim 10 wherein the parasite is a nematode.