Process for preparing a tetrazole-substituted anthranilic acid diamide derivative

Patent metadata

Field	Value
Publication number	US-12545661-B2
Application number	US-202118024722-A
Country	US
Kind code	B2
Filing date	Sep 2, 2021
Priority date	Sep 4, 2020
Publication date	Feb 10, 2026
Grant date	Feb 10, 2026

Abstract

The present invention relates to a process for preparing a tetrazole-substituted anthranilic acid diamide derivative according to formula (I)

in crystalline form via solvate crystals in high purity and high yield. The present invention also further relates to the provision of novel solvate crystals which are distinguished by improved filtration properties compared to a tetrazole-substituted anthranilic acid diamide derivative according to the abovementioned formula (I) in crystalline form.

First claim

The invention claimed is:

1 . A large-scale industrial production process for preparing a compound of formula (I):

in crystalline form, comprising:
dissolving a compound of formula (I) in at least one amide solvent, wherein the at least one amide solvent is selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methyl-2-pyrrolidone, N-methylcaprolactam and hexamethylphosphoramide;
crystallizing the compound to give a solvate in the presence of at least one antisolvent and at a decreased temperature, wherein the at least one antisolvent is selected from the group consisting of acetonitrile, C 1 -C 6 alcohols, toluene, xylene, esters of formic acid with C 1 -C 4 alcohols and esters of acetic acid with C 1 -C 4 alcohols; and
subsequently filtering and drying the compound.

2 . The process of claim 1 , wherein the weight ratio of the at least one amide solvent to the at least one antisolvent is between 10:1 and 1:1.

3 . The process of claim 1 , wherein the solvate crystallization is carried out at temperatures of −20 to +30° C.

4 . The process of claim 1 , wherein the compound of formula (I) is prepared in an amide solvent by:
reacting a compound of formula (II):

with a compound of formula (III):

in the presence of an amide solvent.

5 . The process of claim 4 , wherein the compound of formula (II) is prepared by:
reacting a compound of formula (IV):

with an acid halide former selected from the group consisting of phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride and thionyl chloride in the presence of an inert organic solvent.

6 . A crystalline N,N-dimethylacetamide solvate of a compound of formula (I):

which has at least the following reflections in the X-ray powder diffractogram at a temperature of 25° C. using Cu Kα radiation: 8.3, 8.9, 14.6 (specified as ° 2 theta value±0.2°).

7 . The crystalline N,N-dimethylacetamide solvate of a compound of formula (I) according to claim 6 , wherein the Raman spectrum thereof has at least the following bands: 3126, 1685, 1340 (specified as band [cm −1 ]; in each case±2° cm −1 ).

8 . A crystalline N-methyl-2-pyrrolidone solvate of a compound of formula (I):

which has at least the following reflections in the X-ray powder diffractogram at a temperature of 25° C. using Cu Kα radiation: 8.3, 8.9, 14.6 (specified as ° 2 theta value±0.2°).

9 . The crystalline N-methyl-2-pyrrolidone solvate of a compound of formula (I) according to claim 8 , wherein the Raman spectrum thereof has at least the following bands: 3125, 1684, 1342 (specified as band [cm −1 ]; in each case±2° cm −1 ).

10 . A process for preparing a compound of formula (I):

in crystalline form, comprising:
obtaining the compound of formula (I) in crystalline form from
a) a crystalline N,N-dimethylacetamide solvate of a compound of formula (I) which has at least the following reflections in the X-ray powder diffractogram at a temperature of 25° C. using Cu Kα radiation: 8.3, 8.9, 14.6 (specified as ° 2 theta value±0.2°); and/or

a crystalline N-methyl-2-pyrrolidone solvate of a compound of formula (I) which has at least the following reflections in the X-ray powder diffractogram at a temperature of 25° C. using Cu Kα radiation: 8.3, 8.9, 14.6 (specified as ° 2 theta value±0.2°).

11 . The process of claim 1 , wherein the crystalline form of the compound of formula (I) has an X-ray powder diffractogram at a temperature of 25° C. and using Cu Kα radiation having at least the following reflections (2 theta): 5.8°, 6.4°, 11.6°, 17.5°, 19.8°, 20.8°, 23.5° and 24.2° (in each case±0.2°).

12 . The process of claim 1 , wherein the crystalline form of the compound of formula (I) has a Raman spectrum having at least the following bands [cm −1 ]: 2928, 1663, 1386, 1334, 1022, 638 (in each case±2° cm −1 ).

13 . The process of claim 1 , wherein the crystalline form of the compound of formula (I) has an IR spectrum having at least the following bands [cm −1 ]: 3286, 1662, 1219, 1181, 1154, 1055 (in each case±2° cm −1 ).

14 . The process of claim 10 , wherein the crystalline form of the compound of formula (I) has an X-ray powder diffractogram at a temperature of 25° C. and using Cu Ka radiation having at least the following reflections (2 theta): 5.8°, 6.4°, 11.6°, 17.5°, 19.8°, 20.8°, 23.5° and 24.2° (in each case±0.2°).

15 . The process of claim 10 , wherein the crystalline form of the compound of formula (I) has a Raman spectrum having at least the following bands [cm −1 ]: 2928, 1663, 1386, 1334, 1022, 638 (in each case±2° cm −1 ).

16 . The process of claim 10 , wherein the crystalline form of the compound of formula (I) has an IR spectrum having at least the following bands [cm −1 ]: 3286, 1662, 1219, 1181, 1154, 1055 (in each case±2° cm −1 ).

17 . The process of claim 10 , wherein
the crystalline N,N-dimethylacetamide solvate of a compound of formula (I) has at least the following bands in the Raman spectrum thereof: 3126, 1685, 1340 (specified as band [cm −1 ]; in each case±2° cm −1 ); and/or the crystalline N-methyl-2-pyrrolidone solvate of a compound of formula (I), has at least the following bands in the Raman spectrum thereof: 3125, 1684, 1342 (specified as band [cm −1 ]; in each case±2° cm −1 ).

Assignees

• Bayer Ag

Inventors

• Gallenkamp Daniel
• Beckmann Edith
• Elias Ute
• Havekost Dirk
• Sowa Michal
• Olenik Britta

Classifications

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title