IP Library › Granted Patent US 7,608,604
Granted Patent B2
US 7,608,604 · App. 12/028,192 · Granted Oct 27, 2009

Antiparasitic agents

Assignee: Pfizer Limited
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Quick Facts
Patent No.
US 7,608,604
App. No.
12/028,192
Granted
Oct 27, 2009
Kind
B2
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: R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from H, halo, CN, CF 3 and CONH 2 ; compositions containing such compounds and the uses of such compounds as antiparasitic agents.

Claims (33)

1. A compound of the formula

or a pharmaceutically acceptable salt of said compound, wherein:

R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from H, halo, CN, CF 3 and CONH 2 .

2. A compound according to claim 1 wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from H, F, Cl, Br, CN and CF 3 .

3. A compound according to claim 2 wherein at least one of R 1 , R 2 , R 3 , R 4 and R 5 is CN and at least two of R 1 , R 2 , R 3 , R 4 and R 5 are H.

4. A compound according to claim 2 wherein R 1 and R 4 are H, one of R 2 and R 3 is H and the other is CN, and R 5 is selected from F, Cl, Br and CF 3 .

5. A compound according to claim 4 wherein R 3 is CN and R 5 is CF 3 .

6. 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

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

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

9. 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.

10. 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 .

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

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2014
From: PFIZER LIMITED
To: PFIZER ANIMAL HEALTH UK 1 LIMITED
Reel/Frame 032948/0351 →
Continuity (3)
Provisional Application 6094682000 · Jun 28, 2007
Provisional Application 6088904100 · Feb 9, 2007
Related Publication 20080194694A1 · Aug 14, 2008