IP Library › Granted Patent US 12,286,455

Granted Patent B2

US 12,286,455 · App. 16/943,114 · Granted Apr 29, 2025

Anthelmintic depsipeptide compounds

Inventors: Loic Le Hir de Fallois (Hopewell, NJ); Greg Pacofsky (Raleigh, NC); Alan Long (Flowery Branch, GA); Charles Meng (Grayson, GA); Hyoung Ik Lee (Alpharetta, GA); Cyprian O. Ogbu (Durham, NC)

Assignee: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

C07K11/02 A01N43/72 A61K38/12 A61K38/15 C07D273/00 A61K38/00

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Quick Facts

Patent No.: US 12,286,455
App. No.: 16/943,114
Granted: Apr 29, 2025
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

The present invention provides cyclic depsipeptide compounds of formula (I) and compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

Claims (1306)

1. An anthelmintic cyclic depsipeptide compound of formula (I), or a pharmaceutically acceptable salt thereof:

wherein:

R′, R″, R″′ and R″″ are each methyl; and

R a , R b , R 1 , R 2 , R 3 , R 4 , Cy 1 and Cy 2 are shown in the table below:

R a /R b

R 1

R 2

R 3

R 4

Cy 1 /Cy 2

2-15

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Ph/Ph,

2-16

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Ph/Ph,

2-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Ph/Ph,

2-20

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Ph/Ph,

3-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-F-Ph/

p-F-Ph,

3-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-F-Ph/

p-F-Ph,

3-20

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-F-Ph/

p-F-Ph,

3-26

CH 3 /CH 3

CH 2 CMe 2 F

p-F-Ph/

p-F-Ph,

3-31

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

p-F-Ph/

p-F-Ph,

4-6

CH 3 /CH 3

CH 2 —iPr

CH 2 —tBu

CH 2 —iPr

CH 2 —tBu

p-CF 3 -Ph/

p-CF 3 -Ph,

4-7

CH 3 /CH 3

CH 2 —tBu

CH 2 —iPr

CH 2 —tBu

CH 2 —iPr

p-CF 3 -Ph/

p-CF 3 -Ph,

4-8

CH 3 /CH 3

CH 2 —iPr

CH 2 —tBu

CH 2 —iPr

p-CF 3 -Ph/

p-CF 3 -Ph,

4-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CF 3 -Ph/

p-CF 3 -Ph,

4-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-CF 3 -Ph/

p-CF 3 -Ph,

4-20

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CF 3 -Ph/

p-CF 3 -Ph,

4-26

CH 3 /CH 3

CH 2 CMe 2 F

p-CF 3 -Ph/

p-CF 3 -Ph,

4-31

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

p-CF 3 -Ph/

p-CF 3 -Ph,

4-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —-tBu

p-CF 3 -Ph/

p-CF 3 -Ph,

5-6

CH 3 /CH 3

CH 2 —iPr

CH 2 —tBu

CH 2 —iPr

CH 2 —tBu

p-OCF 3 -Ph/

p-OCF 3 -Ph,

5-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-OCF 3 -Ph/

p-OCF 3 -Ph,

6-16

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-mor-Ph/

p-mor-Ph,

6-20

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-24

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-mor-Ph/

p-mor-Ph,

6-26

CH 3 /CH 3

CH 2 CMe 2 F

p-mor-Ph/

p-mor-Ph,

6-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-mor-Ph/

p-mor-Ph,

6-33

CH 3 /CH 3

CH 2 CF 2 Me

CH 2 —iPr

CH2CF 2 Me

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-34

CH 3 /CH 3

CH 2 CF 3

CH 2 —iPr

CH 2 CF 3

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-35

CH 3 /CH 3

CH 2 CH—

CH 2 —iPr

CH 2 CH—

CH 2 —iPr

p-mor-Ph/

(CF 3 ) 2

p-mor-Ph,

6-36

CH 2 F/CH 2 F

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-37

H/H

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-38

Et/Et

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-39

CH 2 F/CH 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-42

H/H

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-mor-Ph/

p-mor-Ph,

6-43

CH 3 /CH 3

CH 2 CMe 2 F

iPr

CH 2 CMe 2 F

iPr

p-mor-Ph/

p-mor-Ph,

6-44

CH 3 /CH 3

CH 2 CMe 2 F

nPr

p-mor-Ph/

p-mor-Ph,

6-45

CH 3 /CH 3

CH 2 CMe 2 F

sBu

CH 2 CMe 2 F

sBu

p-mor-Ph/

p-mor-Ph,

6-46

CH 3 /CH 3

CH 2 CMe 2 F

tBu

CH 2 CMe 2 F

tBu

p-mor-Ph/

p-mor-Ph,

6-49

CH 3 /CH 3

CH 2 CMe 2 F

CH 3

CH 2 CMe 2 F

CH 3

p-mor-Ph/

p-mor-Ph,

7-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-THP-Ph/

p-THP-Ph,

7-31

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH2CMe2F

p-THP-Ph/

p-THP-Ph,

7-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-THP-Ph/

p-THP-Ph,

7-34

CH 3 /CH 3

CH 2 CF 3

CH 2 —iPr

CH 2 CF 3

CH 2 —iPr

p-THP-Ph/

p-THP-Ph,

7-37

H/H

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-THP-Ph/

p-THP-Ph,

7-38

Et/Et

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-THP-Ph/

p-THP-Ph,

7-42

H/H

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-THP-Ph/

p-THP-Ph,

7-44

CH 3 /CH 3

CH 2 CMe 2 F

nPr

CH 2 CMe 2 F

nPr

p-THP-Ph/

p-THP-Ph,

7-45

CH 3 /CH 3

CH 2 CMe 2 F

sBu

CH 2 CMe 2 F

sBu

p-THP-Ph/

p-THP-Ph,

7-46

CH 3 /CH 3

CH 2 CMe 2 F

tBu

CH 2 CMe 2 F

tBu

p-THP-Ph/

p-THP-Ph,

7-47

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 -p-

CH 2 CMe 2 F

CH 2 -p-

p-THP-Ph/

biphenyl

p-THP-Ph,

7-48

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 -p-

CH 2 CMe 2 F

CH 2 -p-

p-THP-Ph/

tBuPh

p-THP-Ph,

7-49

CH 3 /CH 3

CH 2 CMe 2 F

CH 3

CH 2 CMe 2 F

CH 3

p-THP-Ph/

p-THP-Ph,

7-50

H/H

CH 2 CMe 2 F

iPr

CH 2 CMe 2 F

iPr

p-THP-Ph/

p-THP-Ph,

7-51

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 CH 2 C—

CH 2 CMe 2 F

CH 2 CH 2 C

p-THP-Ph/

Me 3

p-THP-Ph,

7-52

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 CH 2 —

CH 2 CMe 2 F

CH 2 CH 2 —

p-THP-Ph/

iPr

p-THP-Ph,

9-6

CH 3 /CH 3

CH 2 —iPr

CH2-tBu

CH 2 —iPr

CH 2 —tBu

p-mor-3-pyr/

p-mor-3-pyr,

9-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-3-pyr/

p-mor-3-pyr,

9-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-mor-3-pyr/

p-mor-3-pyr,

10-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CF 3 -2-pyr/

p-CF 3 -2-pyr,

11-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CF 3 -3-pyr/

p-CF 3 -3-pyr,

13-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-THP-3-pyr/

p-THP-3-pyr,

18-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-tBu-Ph/

p-tBu-Ph,

18-19

CH 3 /CH 3

CH 2 —iPr

CH2CMe2F

CH 2 —iPr

CH 2 CMe 2 F

p-tBu-Ph/

p-tBu-Ph,

18-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-tBu-Ph/

p-tBu-Ph,

19-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-19/

Cy-19,

24-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CN-Ph/

p-CN-Ph,

29-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-29/

Cy-29,

30-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-30/

Cy-30,

30-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

Cy-30/

Cy-30,

31-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-31/

Cy-31,

32-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-32/

Cy-32,

32 27

CH 3 /CH 3

CH 2 —iPr

Cy-32/

Cy 32,

32-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

Cy-32/

Cy-32,

33-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-33/

Cy-33,

34-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-34/

Cy-34,

35-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-35/

Cy-35,

35-32

CH 3 /CH 3

CH 2 CMe 2 F

CCH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

Cy-35/

Cy-35,

36-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-36/

Cy-36,

37-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-37/

Cy-37; or

38-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-38/

Cy-38;

wherein:

CH 2 -iPr is —CH 2 CH(CH 3 ) 2 ;

CH 2 -tBu is —CH 2 C(CH 3 ) 3 ;

CH 2 CMe 2 F is —CH 2 C(CH 3 ) 2 F;

Et is ethyl;

nPr is n-propyl;

sBu is sec-butyl;

tBu is tert-butyl;

Ph is phenyl;

p-F-Ph is para-fluorophenyl;

p-CF 3 -Ph is para-trifluoromethylphenyl;

p-OCF 3 -Ph is para-trifluoromethoxyphenyl;

p-tBu-Ph is para-tert-butylphenyl;

p-mor-Ph is the group

p-THP-Ph is the group

p-mor-3-pyr is the group

p-CF 3 -2-pyr is the group

p-CF 3 -3-pyr is the group

p-THP-3-pyr is the group

Cy-19 is the group

Cy-29 is the group

Cy-30 is the group

Cy-31 is the group

Cy-32 is the group

Cy-33 is the group

Cy-34 is the group

Cy-35 is the group

Cy-36 is the group

Cy-37 is the group

and

Cy-38 is the group

2. The anthelmintic cyclic depsipeptide of claim 1 , wherein the cyclic depsipeptide is

3. The anthelmintic cyclic depsipeptide compound of claim 1 , wherein R a , R b , R 1 , R 2 , R 3 , R 4 , Cy 1 and Cy 2 are shown in the table below:

R a /R b

R 1

R 2

R 3

R 4

Cy 1 /Cy 2

2-15

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Ph/Ph,

2-16

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Ph/Ph,

2-18

CH 3 /CH 3

CH 2 CMe 2 F

CCH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Ph/Ph,

2-20

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Ph/Ph,

3-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-F-Ph/

p-F-Ph,

3-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-F-Ph/

p-F-Ph,

3-20

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-F-Ph/

p-F-Ph,

3-26

CH 3 /CH 3

CH 2 CMe 2 F

p-F-Ph/

p-F-Ph,

3-31

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

p-F-Ph/

p-F-Ph,

4-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CF 3 -Ph/

p-CF 3 -Ph,

4-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —Pr

CH 2 CMe 2 F

p-CF 3 -Ph/

p-CF 3 -Ph,

4-20

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CF 3 -Ph/

p-CF 3 -Ph,

4-26

CH 3 /CH 3

CH 2 CMe 2 F

p-CF 3 -Ph/

p-CF 3 -Ph,

4-31

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

p-CF 3 -Ph/

p-CF 3 -Ph,

4-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-CF 3 -Ph/

p-CF 3 -Ph,

5-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-OCF 3 -Ph/

p-OCF 3 -Ph,

6-16

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-mor-Ph/

p-mor-Ph,

6-20

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH2CMe2F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-24

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-mor-Ph/

p-mor-Ph,

6-26

CH 3 /CH 3

CH 2 CMe 2 F

p-mor-Ph/

p-mor-Ph,

6-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-mor-Ph/

p-mor-Ph,

6-33

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CF 2 Me

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-34

CH 3 /CH 3

CH 2 CF 3

CH 2 —iPr

CH 2 CF 3

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-35

CH 3 /CH 3

CH 2 CH—

CH 2 —iPr

CH 2 CH—

CH 2 —iPr

p-mor-Ph/

(CF 3 ) 2

p-mor-Ph,

6-36

CH 2 F/CH 2 F

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-37

H/H

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-38

Et/Et

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-Ph/

p-mor-Ph,

6-42

H/H

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-mor-Ph/

p-mor-Ph,

6-43

CH 3 /CH 3

CH 2 CMe 2 F

iPr

CH 2 CMe 2 F

iPr

p-mor-Ph/

p-mor-Ph,

6-44

CH 3 /CH 3

CH 2 CMe 2 F

nPr

CH 2 CMe 2 F

nPr

p-mor-Ph/

p-mor-Ph,

6-45

CH 3 /CH 3

CH 2 CMe 2 F

sBu

CH 2 CMe 2 F

sBu

p-mor-Ph/

p-mor-Ph,

6-46

CH 3 /CH 3

CH 2 CMe 2 F

tBu

CH 2 CMe 2 F

p-mor-Ph/

p-mor-Ph,

6-49

CH 3 /CH 3

CH 2 CMe 2 F

CH 3

CH 2 CMe 2 F

CH 3

p-mor-Ph/

p-mor-Ph,

7-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-THP-Ph/

p-THP-Ph,

7-31

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

p-THP-Ph/

p-THP-Ph,

7-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-THP-Ph/

p-THP-Ph,

7-34

CH 3 /CH 3

CH 2 CF 3

CH 2 —iPr

CH 2 CF 3

CH 2 —iPr

p-THP-Ph/

p-THP-Ph,

7-37

H/H

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-THP-Ph/

p-THP-Ph,

7-38

Et/Et

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-THP-Ph/

p-THP-Ph,

7-42

H/H

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-THP-Ph/

p-THP-Ph,

7-44

CH 3 /CH 3

CH 2 CMe 2 F

nPr

CH 2 CMe 2 F

nPr

p-THP-Ph/

p-THP-Ph,

7-45

CH 3 /CH 3

CH 2 CMe 2 F

sBu

CH 2 CMe 2 F

sBu

p-THP-Ph/

p-THP-Ph,

7-46

CH 3 /CH 3

CH 2 CMe 2 F

tBu

CH 2 CMe 2 F

tBu

p-THP-Ph/

p-THP-Ph,

7-47

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 -p-

CH 2 CMe 2 F

CH 2 -p-

p-THP-Ph/

biphenyl

p-THP-Ph,

7-48

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 -p-

CH 2 CMe 2 F

CH 2 -p-

p-THP-Ph/

tBuPh

p-THP-Ph,

7-49

CH 3 /CH 3

CH 2 CMe 2 F

CH 3

CH 2 CMe 2 F

CH 3

p-THP-Ph/

p-THP-Ph,

7-50

H/H

CH 2 CMe 2 F

iPr

CH 2 CMe 2 F

iPr

p-THP-Ph/

p-THP-Ph,

7-51

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 CH 2 C—

CH 2 CMe 2 F

CH 2 CH 2 C

p-THP-Ph/

Me 3

p-THP-Ph,

7-52

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 CH 2 —

CH 2 CMe 2 F

CH 2 CH 2 —

p-THP-Ph/

iPr

p-THP-Ph,

9-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-mor-3-pyr/

p-mor-3-pyr,

9-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-mor-3-pyr/

p-mor-3-pyr,

10-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CF 3 -2-pyr/

p-CF 3 -2-pyr,

11-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CF 3 -3-pyr/

p-CF 3 -3-pyr,

13-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-THP-3-pyr/

p-THP-3-pyr,

18-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-tBu-Ph/

p-tBu-Ph,

18-19

CH 3 /CH 3

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

p-tBu-Ph/

p-tBu-Ph,

18-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

p-tBu-Ph/

p-tBu-Ph,

19-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-19/

Cy-19,

24-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

p-CN-Ph/

p-CN-Ph,

29-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-29/

Cy-29,

30-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-30/

Cy-30,

30-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

Cy-30/

Cy-30,

31-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-31/

Cy-31,

32-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-32/

Cy-32,

32-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

Cy-32/

Cy-32,

33-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-33/

Cy-33,

34-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-34/

Cy-34,

35-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-35/

Cy-35,

35-32

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —tBu

CH 2 CMe 2 F

CH 2 —tBu

Cy-35/

Cy-35,

36-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-36/

Cy-36,

37-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-37/

Cy-37; or

38-18

CH 3 /CH 3

CH 2 CMe 2 F

CH 2 —iPr

CH 2 CMe 2 F

CH 2 —iPr

Cy-38/

Cy-38;

4. An anthelmintic veterinary composition comprising the anthelmintic cyclic depsipeptide of claim 1 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

5. An anthelmintic veterinary composition comprising the anthelmintic cyclic depsipeptide of claim 2 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

6. An anthelmintic veterinary composition comprising the anthelmintic cyclic depsipeptide of claim 3 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2023

From: MERIAL, INC.

To: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

Reel/Frame 063507/0094 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2023

From: LE HIR DE FALLOIS, LOIC; PACOFSKY, GREG; LONG, ALAN; MENG, CHARLES; LEE, HYOUNG IK; OGBU, CYPRIAN O.

To: MERIAL INC.

Reel/Frame 063477/0346 →

Continuity (4)

Continuation 16111027 · Aug 23, 2018

Division 15160577 · May 20, 2016

Provisional Application 62163997 · May 20, 2015

Related Publication 20200354408A1 · Nov 12, 2020

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