Pyrazolopyrans having herbicidal and pharmaceutical properties

Patent metadata

Field	Value
Publication number	US-9480259-B2
Application number	US-201314405942-A
Country	US
Kind code	B2
Filing date	May 29, 2013
Priority date	Jun 6, 2012
Publication date	Nov 1, 2016
Grant date	Nov 1, 2016

Abstract

The present invention relates to a pyrazolopyran of the general formula I wherein the variables are defined according to the description, including a tautomer, salt, cleavable prodrug, or mixtures thereof, in particular to said pyrazolopyran for use as a medicament and/or an inhibitor of the enzyme serinehydroxymethyltransferase (SHMT). The invention also relates to a process the preparation of a pyrazolopyran of the formula I, to compositions comprising said compound and processes for the preparation of these compositions. Further it relates to use of the pyrazolopyran of formula I as an herbicide as well as to a method of controlling undesired vegetation.

First claim

The invention claimed is:

1. A compound of formula I

wherein
R 1 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -halocyclo-alkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, hydroxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, or cyano,
R 2 is C 2 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -halocycloalkenyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -hydroxyhaloalkyl, C 1 -C 6 -hydroxycycloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -cyanoalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, or 3-7-membered heterocyclyl, 3-7-membered haloheterocyclyl,
wherein each heterocyclyl has one to three nitrogen atoms and/or one or two oxygen and/or sulfur atoms,

R 3 is phenyl substituted by 1-3 substituents selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, phenyl, phenyloxy, wherein each of the phenyl groups may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of cyano, C 1 -C 6 -alkyl, C 1 -C 6 haloalkyl, and C 1 -C 6 -alkoxy
or a tautomer, salt, or mixtures thereof.

2. The pyrazolopyran of claim 1 in form of an agriculturally useful salt.

3. The pyrazolopyran of claim 1 in form of a pharmaceutically acceptable salt.

4. The compound of claim 1 , wherein R 1 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, and C 2 -C 6 -haloalkynyl.

5. The compound of claim 4 , wherein R 1 is hydrogen, C 1 -C 6 alkyl, or C 3 -C 6 -cycloalkyl.

6. The compound of claim 5 , wherein R 1 is C 1 -C 6 -alkyl.

7. The compound of claim 1 , wherein R 2 is C 2 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, 3-7-membered heterocyclyl, or 3-7-membered haloheterocyclyl.

8. The compound of claim 7 , wherein R 2 is C 2 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, 4-6-membered heterocyclyl, or 4-6-membered haloheterocyclyl.

9. The compound of claim 8 , wherein R 2 is C 2 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, or 4-6-membered heterocyclyl.

10. The compound of claim 9 , wherein R 2 is ethyl, i-propyl, cyclobutyl, oxetanyl, cyclopropyl or cyclopentenyl.

11. A herbicidal composition comprising a herbicidal active amount of a pyrazolopyran as defined in claim 1 and auxiliaries customary for formulating crop protection agents.

12. A pharmaceutical composition comprising a pharmaceutically effective amount of a pyrazolopyran as defined in claim 1 and auxiliaries customary for formulating pharmaceuticals.

13. A process for the preparation of a pyrazolopyran of formula I as defined in claim 1 , wherein a vinyl-1,1-dinitrile of formula II

is cyclized with an hydroxypyrazole of formula III,

to give the pyrazolopyran of formula I,

14. A process for the preparation of a herbicidal composition, which comprises mixing a herbicidal active amount of a pyrazolopyran as defined in claim 1 and auxiliaries customary for formulating crop protection agents.

15. A process for the preparation of a pharmaceutical composition, which comprises mixing a pharmaceutically effective amount of a pyrazolopyran as defined in claim 1 and auxiliaries customary for formulating pharmaceuticals.

16. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of a compound of claim 1 to act on plants, their environment or on seed, provided that treating of human or animal body is excluded.

17. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of a compound of claim 4 to act on plants, their environment or on seed.

18. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of a compound of claim 5 to act on plants, their environment or on seed.

19. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of a compound of claim 6 to act on plants, their environment or on seed.

20. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of a compound of claim 7 to act on plants, their environment or on seed.

21. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of a compound of claim 8 to act on plants, their environment or on seed.

22. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of a compound of claim 9 to act on plants, their environment or on seed.

23. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of a compound of claim 10 to act on plants, their environment or on seed.

Assignees

• Basf Se

Inventors

• Witschel Matthias
• Stelzer Frank
• Hutzler Johannes
• Qu Tao
• Mietzner Thomas
• Kreuz Klaus
• Grossmann Klaus
• Aponte Raphael
• Hoeffken Hans Wolfgang
• Calo Frederick
• Ehrhardt Thomas
• Simon Anja
• Parra Rapado Liliana

Classifications

• C07D491/052

  the oxygen-containing ring being six-membered · CPC title

• C07D311/94

  condensed with rings other than six-membered or with ring systems containing such rings · CPC title

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A01N47/20

  N-Aryl derivatives thereof · CPC title