Anthelmintic compounds

• US 10,463,661 B2
• Filed: 08/03/2018
• Issued: 11/05/2019
• Est. Priority Date: 05/19/2014
• Status: Active Grant

• Current Assignee: Boehringer Ingelheim Animal Health USA, Inc. (C.H. Boehringer Sohn AG & Co. KG)
• Original Assignee: Boehringer Ingelheim Animal Health USA, Inc. (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: Long, Alan, Gurrala, Srinivas Reddy
• Primary Examiner(s): Pagano, Alexander R
• Application Number:
  US16/054,101
• Publication Number:
  US 20180338972A1
• Time in Patent Office: 459 Days
• CPC Class Codes: A61K 31/06 the aromatic ring being substituted by nitro groups
• CPC Class Codes: A61K 31/423 condensed with carbocyclic rings
• CPC Class Codes: A61K 31/4468 having a nitrogen directly attached in position 4, e.g. clebopride, fentanyl
• CPC Class Codes: A61K 31/454 containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
• CPC Class Codes: A61K 31/495 having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazinesA61K31/48 takes precedence ; with three nitrogen atoms A61K31/53
• CPC Class Codes: A61K 31/496 Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: A61P 33/10 Anthelmintics
• CPC Class Codes: A61P 33/14 Ectoparasiticides, e.g. scabicides
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C07D 487/06 Peri-condensed systems
• CPC Class Codes: H05B 41/06 thermal only

Abstract

The present invention relates to novel anthelmintic compounds of formula (I) below:

wherein

• • Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group, or one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl, and variables X₁, X₆, X₈, Q₁, Q₂, Q₃, Q₄, Q₅, Q₆, Ring A, Ring B, W, W′, R₂, R₃, R, R′, m, n and q are as defined herein. The invention also provides for veterinary compositions comprising the anthelmintic compounds of the invention, and their uses for the treatment and prevention of parasitic infections in animals.

Claims

1. An anthelmintic compound of formula (IA-1):

2. The anthelmintic compound of claim 1, wherein Y is optionally substituted benzoxazolyl or benzothiazolyl.

3. The anthelmintic compound of claim 1, wherein Z is phenyl substituted by halogen, cyano or CF₃.

4. The anthelmintic compound of claim 1, wherein X₁ is a bond.

5. The anthelmintic compound of claim 1, wherein X₈ is a bond.

6. The anthelmintic compound of claim 1, wherein X₁ and X₈ are each bonds.

7. The anthelmintic compound of claim 1, wherein X₆ is —

O—

or —

NH—

.

8. The anthelmintic compound of claim 1, wherein Y is optionally substituted benzoxazolyl or benzothiazolyl;

and Z is phenyl substituted by halogen, cyano or CF₃.

9. The anthelmintic compound of claim 1, wherein Ring A is L1.

10. The anthelmintic compound of claim 1, wherein:

Y is optionally substituted benzoxazolyl or benzothiazolyl;

Z is phenyl substituted by halogen, cyano or CF₃; and

Ring A is L1.

11. The anthelmintic compound of claim 10, wherein X₁ is a bond.

12. The anthelmintic compound of claim 10, wherein X₈ is a bond.

13. The anthelmintic compound of claim 10, wherein X₆ is —

O—

.

14. The anthelmintic compound of claim 10, wherein:

X₁ and X₈ are each bonds;

X₆ is —

O—

; and

n is 1.

15. The anthelmintic compound of claim 14, wherein Y is benzoxazolyl or benzothiazolyl substituted by CF₃, SCF₃ or OCF₃.

16. The anthelmintic compound of claim 15, wherein Z is phenyl substituted by cyano, CF₃ or fluoro.

17. The anthelmintic compound of claim 1, wherein the compound has the structure

18. A composition for the treatment and prevention of a parasitic infection or infestation in an animal, comprising an effective amount of at least one anthelmintic compound of claim 1 in combination with a pharmaceutically acceptable carrier.

19. The composition of claim 18, wherein the composition comprises an additional parasiticidal active agent.

20. A method for the treatment and prevention of a parasitic infection or infestation in an animal, comprising administering an effective amount of the compound of claim 1 to the animal.