Azetidine-substituted pyridine and pyrazine compounds as inhibitors of cannabinoid receptor 2
US-12180196-B2 · Dec 31, 2024 · US
US11064697B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11064697-B2 |
| Application number | US-201615746866-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jul 18, 2016 |
| Priority date | Jul 24, 2015 |
| Publication date | Jul 20, 2021 |
| Grant date | Jul 20, 2021 |
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The present invention relates to compounds I wherein the variables are defined as given in the description and claims. The invention further relates to uses, processes and intermediates for compounds I.
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The invention claimed is: 1. A compound of the formula I wherein R 1 is in each case independently selected from hydrogen, halogen, CN, C 1 -C 6 -alkyl, wherein the aliphatic moieties of R 1 are unsubstituted or substituted with identical or different groups R 1a which independently of one another are selected from: R 1a halogen; R 2 is in each case independently selected from the substituents as defined for R 1 ; R 3 , R 4 are C 1 -C 6 -alkyl; R 5 is halogen; R 6 is selected from H and halogen; R 9 , R 10 are independently selected from H, halogen, CN, N(R 9 )(R 92 ), S(R 93 ), S(O) z94 (R 94 ), O(R 95 ), C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, cycloalkyl, CO—(R 96 ); R 91 , R 92 are independently selected from H, alkyl; R 93 is alkyl; R 94 is alkyl; z 94 is 1 or 2; R 95 is alkyl; R 96 is independently selected from alkyl, N(R 962 )(R 963 ); R 962 , R 963 are independently selected from H, alkyl; wherein the aliphatic moieties of R 9 , R 10 are unsubstituted or substituted by identical or different groups of R 9a , wherein R 9a independently of one another are selected from: halogen, CN; or R 7 and R 8 together with the carbon atoms to which they are bound form a ring A, wherein the ring A is phenyl, and wherein the ring A is substituent by (R 78 ), wherein o is 0, 1, 2; and R 78 are independently selected from halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenalkoxy; and wherein the aliphatic moieties of R 78 are not further substituted or carry 1, 2, 3 or up to the maximum possible number of identical or different groups R 78a which independently of one another are selected from: R 78a halogen; and an N-oxide and an agriculturally acceptable salt thereof. 2. The compound of claim 1 , wherein R 3 and R 4 are independently selected from C 1 -C 4 -alkyl. 3. The compound of claim 1 , wherein R 5 and R 6 independently are selected from the group consisting of F, Cl, and Br. 4. The compound of claim 1 , wherein R 9 and R 10 independently are selected from the group consisting of H and C 1 -C 4 -alkyl. 5. The compound of claim 1 , wherein R 9 and R 10 independently are selected from the group consisting of CN and halogen. 6. The compound of claim 1 , wherein R 9 and R 10 independently are selected from the group consisting of CO—NH 2 , CO—NH(C 1 -C 4 -alkyl) and CO—N(C 1 -C 4 -alkyl) 2 . 7. The compound of claim 1 , wherein R 9 and R 10 independently are selected from the group consisting of S—(C 1 -C 4 -alkyl), SO—(C 1 -C 4 -alkyl) and SO 2 —(C 1 -C 4 -alkyl). 8. The compound of claim 1 , wherein R 9 and R 10 independently are selected from the group consisting of H, CN, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, CO—NH 2 , CO—NH(C 1 -C 4 -alkyl), CO—N(C 1 -C 4 -alkyl) 2 , S—(C 1 -C 4 -alkyl), SO—(C 1 -C 4 -alkyl) and SO 2 —(C 1 -C 4 -alkyl). 9. A composition comprising one compound of formula I, as defined in claim 1 , an N-oxide or an agriculturally acceptable salt thereof. 10. A method for combating phytopathogenic fungi comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I, as defined in claim 1 . 11. A seed coated with at least one compound of the formula I, as defined in claim 1 or an agriculturally acceptable salt thereof, in an amount of from 0.1 to 10 kg per 100 kg of seed. 12. A method for combating phytopathogenic fungi comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with the composition of claim 9 . 13. A seed coated with the composition of claim 9 in an amount of from 0.1 to 10 kg per 100 kg of seed.
directly linked by a ring-member-to-ring-member bond · CPC title
condensed with carbocyclic rings · CPC title
six-membered rings · CPC title
containing three or more hetero rings · CPC title
containing three or more hetero rings · CPC title
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