IP Library Granted Patent US 9,321,724
Granted Patent B2
US 9,321,724 · App. 14/386,954 · Granted Apr 26, 2016

Heteroaryl compounds with A-cyclic bridging unit

Inventors: Michael Berger (Wiesbaden, DE); Marko Eck (Wiesbaden, DE); Christopher Kern (Edenkoben, DE)
Assignee: Intervet Inc.
C07D213/40C07D207/34C07D213/74C07D213/85C07D215/38C07D217/22C07D241/20C07D249/14C07D271/07C07D277/42C07D277/56C07D401/12C07D405/12C07D409/12C07D413/04C07D471/10C07D487/04
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Quick Facts
Patent No.
US 9,321,724
App. No.
14/386,954
Granted
Apr 26, 2016
Kind
B2
Abstract

This invention relates to certain heteroaryl compounds which may be used as medicaments, more specifically as medicaments for treating animals. The medicament can be used for the treatment of parasitic infections such as helminth infections and the treatment of parasitosis caused by such infections. This invention also relates to uses of the compounds to make medicaments and treatments comprising the administration of the compounds to animals in need of the treatments. This invention also relates to pharmaceutical compositions and kits comprising the compounds.

Claims (27)

1. A compound of the formula (IV) or a pharmaceutically acceptable solvate, N-oxide, or salt thereof,

wherein R 1 is C1-C4 alkyl, wherein each carbon containing radical is optionally substituted by one or more halogen atoms,

R 6 is hydrogen, alkyl, phenyl or benzyl,

R 7 is hydrogen, alkyl, phenyl or benzyl,

n is 1-3,

B and D are N and,

A is a heteroaryl, chosen from the group consisting of a 6 membered aromate according to formula II and a 5 membered heteroaromate according to formula III,

Formula II Formula III in formula II:

Y 1 , Y 2 ,Y 4 and Y 5 may be N or CR 9 , wherein at least one and at most three of Y 1 , Y 2 , Y 4 and Y 5 is N,

Y 3 is CR 10 ,

R 9 is hydrogen, alkyl, alkoxy, alkylthio, halogen, nitrilo, nitro, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, amino, dialkylamino, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, alkylcarbonylamino, phenyl wherein each of the carbon-containing radicals optionally is substituted by one or more halogen atoms,

R 10 is hydrogen, alkyl, alkoxy, alkylthio, halogen, nitrilo, nitro, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, N-piperidinyl, N-morpholinyl, alkylcarbonylamino, phenyl wherein each of the carbon-containing radicals optionally is substituted by one or two halogen atoms,

Y 1 and Y 2 may form a ring system or Y 2 and Y 3 may form a ring system or Y 3 and Y 4 may form a ring system or Y 4 and Y 5 may form a ring system,

and in formula III:

Y 6 is N or C,

Y 7 , Y 8 , Y 9 and Y 10 is CR 11 , NR 12 , O or S, wherein at least one and at maximum three of Y 7 , Y 8 , Y 9 and Y 10 is NR 12 , O or S,

R 11 is hydrogen, alkyl, alkylthio, nitrilo, alkoxycarbonyl, aminocarbonyl, alkylsulfonyl, aminosulfonyl, alkylamino, dialkylamino, N-piperidinyl, N-morpholinyl, phenyl, wherein each of the carbon-containing radicals optionally is substituted by one or more halogen atoms,

R 12 is hydrogen, alkyl or missing,

Y 7 and Y 8 may form a ring system or Y 8 and Y 9 may form a ring system.

2. The compound of claim 1 , wherein the compound is

3. A method of treating a parasitic infection in an animal comprising administering to the animal, a compound according to claim 1 ,

for use in the treatment of a parasitic infection of an animal.

4. The method of claim 3 , wherein the parasitic infection is a helminth infection.

5. A method of treating a parasitic infection in an animal comprising administering to the animal, a compound according to claim 2 .

6. The method of claim 5 , wherein the parasitic infection is a helminth infection.

7. An antiparasitic composition comprising one or more compounds of claim 1 and one or more pharmaceutically acceptable excipients.

8. An antiparasitic composition comprising the compound of claim 2 and one or more pharmaceutically acceptable excipients.

Assignments (2)
CHANGE OF ADDRESS Recorded Sep 26, 2023
From: INTERVET INC.
To: INTERVET INC.
Reel/Frame 065028/0818 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2014
From: BERGER, MICHAEL; ECK, MARKO; KERN, CHRISTOPHER
To: INTERVET INC.
Reel/Frame 033788/0368 →
Priority Claims (1)
EP 12161718 · Mar 28, 2012 · regional
Continuity (1)
Related Publication 20150057279A1 · Feb 26, 2015