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US 12,454,523 B2Granted
Pyrazole derivatives
AssigneeSyngenta Crop Protection AG
InventorsSally Elizabeth Russell, James Alan Morris
Life of this patent
Estimating the term…
Abstract
The present invention relates to pyrazole derivatives of formula (X) wherein ring A is a pyrazole and substituents RB1, RB2, n, RQ1, RQ2, RQ3, and RQ4 are as defined in claim 1, their manufacture, and their use in the manufacture of agrochemicals and pharmaceuticals.
Claims9
A method, comprising:
- reacting a compound of formula (X)
- wherein ring A is a di- or tri-substituted pyrazole, substituted on one ring nitrogen by RB2 and substituted on at least one ring carbon by RB3;
- RB2 is C1-C3 alkyl or C1-C3fluoroalkyl;
- n is an integer of 1 or 2,
- each RB3 is independently halogen, C1-C3haloalkoxy, C1-C3haloalkyl, C1-C3alkoxy, or C1-C3alkyl;
- RQ1 and RQ4 are each hydrogen;
- and
- RQ2 and RQ3 together with the carbon atoms to which they are joined form ring Q, which is an optionally substituted 5-membered thio-lactam ring;
- to produce a pharmaceutical or agrochemical having a pyrazolo-pyrrolidone motif.
6 more elements
A compound of formula (E)
- wherein:
- ring A as is a di- or tri-substituted pyrazole, substituted on one ring nitrogen by RB2 and substituted on at least one ring carbon by RB3;
- RB2 is C1-C3 alkyl or C1-C3fluoroalkyl;
- n is an integer of 1 or 2,
- each RB3 is independently halogen, C1-C3fluoroalkyl, C1-C3haloalkoxy, C1-C3alkoxy, C1-C3haloalkyl, or C1-C3alkyl;
- and
- R1 is C1-C6 alkyl, C2-C6alkenyl, C3-C6cyloalkyl, C3-C6cylcoalkenyl, optionally substituted phenyl, optionally substituted C5-C6 heteroaryl, —CR12R13, or —(O)R12;
- R12 is hydrogen, OH, C1-C3 alkoxy, or C1-C4 alkyl;
- and R13 is —C(O) NH2;
- or
- a compound of formula (H)
- wherein:
- ring A as is a di- or tri-substituted pyrazole, substituted on one ring nitrogen by RB2 and substituted on at least one ring carbon by RB3;
- RB2 is C1-C3 alkyl or C1-C3fluoroalkyl;
- n is an integer of 1 or 2,
- each RB3 is independently halogen, C1-C3fluoroalkyl, C1-C3haloalkoxy, C1-C3alkoxy, C1-C3haloalkyl, or C1-C3alkyl;
- and
- R1 is C1-C6 alkyl, C2-C6alkenyl, C3-C6cyloalkyl, C3-C6cylcoalkenyl, optionally substituted phenyl, optionally substituted C5-C6 heteroaryl, —CR12R13, or —C(O)R12,
- R12 is hydrogen, OH, C1-C3 alkoxy, or C1-C4 alkyl;
- and R13 is —C(O) NH2;
- R2 is hydrogen, C1-C6alkyl, —CralkoxyCsalkyl, C1-C6haloalkyl, —CralkoxyCshaloalkyl, C2-C6alkenyl, C2-C6alkynyl, or —(CR21R22)tR20,
- wherein each R20 is independently —C(O)OR23, —OC(O)R23, —C3-C6cycloalkyl, or an -aryl, -aryloxy, -heteroaryl, -heteroaryloxy or -heterocyclyl ring, wherein said ring is optionally substituted by 1 to 3 independent R25;
- r is an integer of 1, 2, 3, 4, or 5, s is an integer of 1, 2, 3, 4, or 5, and the sum of r+s is less than or equal to 6;
- t is an integer of 0, 1, 2, 3, 4, 5 or 6, each R21 is independently hydrogen or C1-C2 alkyl;
- each R22 is independently hydrogen or C1-C2 alkyl;
- R23 is hydrogen or C1-C4alkyl;
- and each R25 is independently halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, cyano, nitro, C1-C6alkylthio, C1-C6alkylsulphinyl, or C1-C6alkylsulphonyl;
- or
- a compound of formula (J)
- wherein:
- ring A as is a di- or tri-substituted pyrazole, substituted on one ring nitrogen by RB2 and substituted on at least one ring carbon by RB3;
- RB2 is C1-C3 alkyl or C1-C3fluoroalkyl;
- n is an integer of 1 or 2,
- each RB3 is independently halogen, C1-C3fluoroalkyl, C1-C3haloalkoxy, C1-C3alkoxy, C1-C3haloalkyl, or C1-C3alkyl;
- and
- R1 is C1-C6 alkyl, C2-C6alkenyl, C3-C6cyloalkyl, C3-C6cylcoalkenyl, optionally substituted phenyl, optionally substituted C5-C6 heteroaryl, —CR12R13, or —C(O)R12;
- R12 is hydrogen, OH, C1-C3 alkoxy, or C1-C4 alkyl;
- and R13 is —C(O) NH2,
- wherein the compound of formula (J) is not
- or
- a compound of formula (D)
- wherein:
- ring A as is a di- or tri-substituted pyrazole, substituted on one ring nitrogen by RB2 and substituted on at least one ring carbon by RB3;
- RB2 is C1-C3 alkyl or C1-C3fluoroalkyl;
- n is an integer of 1 or 2,
- each RB3 is independently halogen, C1-C3fluoroalkyl, C1-C3haloalkoxy, C1-C3alkoxy, C1-C3haloalkyl, or C1-C3alkyl;
- and
- R1 is C1-C6 alkyl, C2-C6alkenyl, C3-C6cyloalkyl, C3-C6cylcoalkenyl, optionally substituted phenyl, optionally substituted C5-C6 heteroaryl, —CR12R13, or —C(O)R12;
- R12 is hydrogen, OH, C1-C3 alkoxy, or C1-C4 alkyl;
- and R13 is —C(O) NH2.
47 more elements
A compound of formula (J)
Dependencies are inferred from the claim text.