Small molecule compounds for the control of nematodes

Patent metadata

Field	Value
Publication number	US-9445596-B2
Application number	US-201214237774-A
Country	US
Kind code	B2
Filing date	Aug 8, 2012
Priority date	Aug 8, 2011
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

The present invention relates to compounds involved in nematode signaling.

First claim

What is claimed:

1. A method of modifying behavior of a nematode, comprising:
providing a composition comprising a compound of Formula I, or a salt thereof; and
administering an effective dosage of the composition to the nematode:

wherein:
each R 1 is independently H, —C(R) 3 , —OR, —N(R) 2 , halogen, an alkyl, a haloalkyl, an alkenyl, or a haloalkenyl; wherein each R is independently H, halogen, an alkyl, or an alkenyl;
R 1′ is absent, H, —C(R) 3 , —OR, —N(R) 2 , halogen, an alkyl, a haloalkyl, an alkenyl, or a haloalkenyl; wherein each R is independently H, halogen, an alkyl, or an alkenyl;
R 2 is a moiety of formula:

R 5′ is selected from H, —OH, —OR 6 , —OCR 6 R 7 R 8 , —CR 6 R 7 R 8 , —NH 2 , —NHR 6 , —NR 6 R 7 , —CR 6 R 7 C(O)NHR 8 , halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, aryl, heteroaryl, arylalkyl, heterocyclyl, cycloalkyl, cycloalkenyl, acyl, amino acid, nucleoside, monosaccharide having 5 or 6 carbon atoms, a bond connecting to R 3 or R 4 of another unit of Formula I,

each R 5 is independently H, —OH, —OR 6 , —OCR 6 R 7 R 8 , —CR 6 R 7 R 8 , —NH 2 , —NHR 6 , —NR 6 R 7 , —CR 6 R 7 C(O)NHR 8 , halogen, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, an arylalkyl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, an acyl, an amino acid, a nucleoside, a monosaccharide having 5 or 6 carbon atoms, or a bond connecting to R 3 or R 4 of another unit of Formula I;
R 6 and R 7 are each independently H, —CR 3 , —OR, —N(R) 2 , halogen, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, or a cycloalkenyl, wherein the alkyl, alkenyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, or cycloalkenyl is optionally substituted with one or more substituents independently selected from the group consisting of —OR 8 , —C(O)R 8 , —NHC(O)R 8 , an alkyl, a haloalkyl, an aryl, a heteroaryl, a heterocyclyl, and a cycloalkyl;
each R is independently H, halogen, an alkyl, or an alkenyl;
each R 8 is H, —C(R) 3 , —[C(R) 2 ] n4 NHC(O)R 9 , —[C(R) 2 ] n4 C(O)(NH)R 9 , —OR, —N(R) 2 , halogen, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, a purine, a pyrimidine, or a monosaccharide having 5 or 6 carbon atoms, wherein the alkyl, alkenyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, purine, pyrimidine, or monosaccharide is optionally substituted with one or more substituents independently selected from the group consisting of —C(R) 3 , —OR 9 , —C(O)R 9 , —NHC(O)R 9 , halogen, an alkyl, a haloalkyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, and a monosaccharide having 5 or 6 carbon atoms;
each R 9 is H, —C(R) 3 , —OR, —N(R) 2 , halogen, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, a purine, a pyrimidine, or a monosaccharide having 5 or 6 carbon atoms, wherein the alkyl, alkenyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkenyl, purine, pyrimidine, or monosaccharide is optionally substituted with one or more substituents independently selected from the group consisting of —C(R) 3 , —OR, —C(O)R, halogen, an alkyl, a haloalkyl, an aryl, a heteroaryl, a heterocyclyl, and a cycloalkyl; wherein each R is independently H, halogen, an alkyl, or an alkenyl; and
n 1 , n 2 , and n 3 are each independently an integer of 0 to 30;
n 4 is an integer of 1 to 30;
the sum of n 1 , each n 2 , and each n 3 is 1 to 30; and

R 3 and R 4 are each independently H, —CR 6 R 7 R 8 , —C(O)R 8 , an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, an acyl, an amino acid, a nucleoside, a monosaccharide having 5 or 6 carbon atoms, or a bond connecting to R 5 of another unit of Formula I;

wherein either:
A) R 5′ is selected from

or
B) R 3 is C(O)alkyl, substituted with a monosaccharide having 5 or 6 carbon atoms, and
R 4 is C(O)alkyl substituted with —NHC(O)NH 2 .

2. The method according to claim 1 , wherein R 5′ is selected from

3. The method according to claim 2 , wherein the compound is a compound of formula:

wherein m 1 is an integer of 1 to 3.

4. The method according to claim 1 , wherein the compound is a compound of Formula IE, IE′, IF, or IF′:

wherein:
R 2a and R 2b are each independently a moiety of formula

5. The method of claim 1 , wherein:
R 3 is C(O)alkyl substituted with a monosaccharide having 5 or 6 carbon atoms, and
R 4 is C(O)alkyl substituted with —NHC(O)NH 2 .

6. The method of claim 1 , wherein the nematode behavior is selected from reproduction, development, dauer formation, aggregation, attraction, repulsion, dispersal, deterrence, feeding, host finding, and host invasion.

7. A method of modifying behavior of a nematode, comprising:
providing a composition comprising a compound selected from:

and administering an effective dosage of the composition to the nematode.

Assignees

• Schroeder Frank C
• Von Reuss Stephan H
• Choe Andrea
• Sternberg Paul W
• California Inst Of Techn
• Boyce Thompson Inst For Plant Res

Inventors

• Schroeder Frank C
• Von Reuss Stephan H
• Choe Andrea
• Sternberg Paul W

Classifications

• A61P33/10

  Anthelmintics · CPC title

• C07H19/16

  Purine radicals · CPC title

• A01N63/10

  Animals; Substances produced thereby or obtained therefrom · CPC title

• C07H15/04

  attached to an oxygen atom of the saccharide radical · CPC title

• A61K31/7076

  containing purines, e.g. adenosine, adenylic acid · CPC title