3′-alkynyl abscisic acid derivatives as ABA antagonists

Patent metadata

Field	Value
Publication number	US-12063929-B2
Application number	US-201917309256-A
Country	US
Kind code	B2
Filing date	Nov 19, 2019
Priority date	Nov 19, 2018
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

The present application relates to novel 3′-unsaturated abscisic acid (ABA) derivatives of Formula (I) as ABA antagonists. For example, the present application relates to methods of using compounds of Formula (I) for reducing adverse effects of an ABA response in plants such as lentil and promoting germination. (I) The present application also relates to methods of using 3′-phenyl abscisic acid (ABA) derivatives of Formula (II) as ABA antagonists, for example, for reducing adverse effects of an ABA response in plants such as lentil and promoting germination. (II)

First claim

The invention claimed is:

1. A compound of Formula (I) or an enantiomer, salt, and/or solvate thereof:

wherein
L is —C═C— or —C≡C—;
R 1 is C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, or (CH 2 ) 0-2 heteroaryl, each being optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), OC 1-6 alkyl, OC 2-6 alkenyl, OC 2-6 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, (CH 2 ) 0-2 heteroaryl, O(CH 2 ) 0-2 C 3-10 cycloalkyl, O(CH 2 ) 0-2 aryl, O(CH 2 ) 0-2 heterocycloalkyl, or O(CH 2 ) 0-2 heteroaryl, the latter 16 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl; and
R 2 is H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, cycloalkyl, aryl, heterocycloalkyl or heteroaryl, the latter 7 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl,
wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.

2. The compound of claim 1 , wherein R 1 is (CH 2 ) 0-2 aryl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), OC 1-6 alkyl, OC 2-6 alkenyl, OC 2-6 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, (CH 2 ) 0-2 heteroaryl, O(CH 2 ) 0-2 C 3-10 cycloalkyl, O(CH 2 ) 0-2 aryl, O(CH 2 ) 0-2 heterocycloalkyl or O(CH 2 ) 0-2 heteroaryl, the latter 16 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.

3. The compound of claim 1 , wherein R 1 is aryl optionally substituted with one or more of OH, halo, C 1-10 alkyl, OC 1-6 alkyl, or O(CH 2 ) 0-2 aryl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.

4. The compound of claim 1 , wherein R 1 is C 1-10 alkyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), OC 1-6 alkyl, OC 2-6 alkenyl, OC 2-6 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, (CH 2 ) 0-2 heteroaryl, O(CH 2 ) 0-2 C 3-10 cycloalkyl, O(CH 2 ) 0-2 aryl, O(CH 2 ) 0-2 heterocycloalkyl, or O(CH 2 ) 0-2 heteroaryl, the latter 16 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.

5. The compound of claim 4 , wherein R 1 is C 1-10 alkyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, or C 2-10 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.

6. The compound of claim 1 , wherein R 1 is C 2-10 alkenyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, or C 2-10 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.

7. The compound of claim 1 , wherein R 1 is (CH 2 ) 0-2 C 3-10 cycloalkyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, NH(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), OC 1-6 alkyl, OC 2-6 alkenyl, OC 2-6 alkynyl, (CH 2 ) 0-2 C 3-10 cycloalkyl, (CH 2 ) 0-2 aryl, (CH 2 ) 0-2 heterocycloalkyl, (CH 2 ) 0-2 heteroaryl, O(CH 2 ) 0-2 C 3-10 cycloalkyl, O(CH 2 ) 0-2 aryl, O(CH 2 ) 0-2 heterocycloalkyl, or O(CH 2 ) 0-2 heteroaryl, the latter 16 groups being optionally substituted with one or more of halo, OH, NH 2 , C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, OC 1-16 alkyl, OC 2-6 alkenyl, or OC 2-6 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.

8. The compound of claim 7 , wherein R 1 is C 3-10 cycloalkyl optionally substituted with one or more of halo, CN, OH, NH 2 , C 1-10 alkyl, C 2-10 alkenyl, or C 2-10 alkynyl, wherein each alkyl, alkenyl, and alkynyl are optionally fluorosubstituted.

9. The compound of claim 1 , wherein R 2 is H or C 1-10 alkyl.

10. The compound of claim 1 , wherein L is —C═C—.

11. The compound of claim 1 , wherein L is —C≡C—.

12. The compound of Formula (I) or a salt, and/or solvate thereof of claim 1 , wherein the compound has the following stereochemistry:

13. The compound of Formula (I) of claim 1 selected from the compounds listed below:

Compound I.D
Structures

1018

1019

1021

1022

1023

1024

1025

1059

Assignees

• Univ Saskatchewan

Inventors

• Abrams Suzanne R
• Lai Leon
• Diddi Naveen

Classifications

• C07C69/738 Primary

  Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} · CPC title

• C07C59/90

  containing singly bound oxygen-containing groups · CPC title

• A01P21/00

  Plant growth regulators · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title