Crystal form of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3) pyridazine-3-carboxamide

Patent metadata

Field	Value
Publication number	US-12545665-B2
Application number	US-202117400100-A
Country	US
Kind code	B2
Filing date	Aug 11, 2021
Priority date	Mar 30, 2017
Publication date	Feb 10, 2026
Grant date	Feb 10, 2026

Abstract

Disclosed is crystalline Form A of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl) amino)-N-(methyl-d 3 )pyridazine-3-carboxamide. Form A is a neat crystalline form. Characterization data for Form A are disclosed.

First claim

What is claimed is:

1 . A method of preparing crystalline Form A of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl) amino)-N-(methyl-d 3 )pyridazine-3-carboxamide, comprising:
(a) mixing 10 grams of Compound (I), which is 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl) amino)-N-(methyl-d 3 )pyridazine-3-carboxamide, into 55 mL of NMP, thereby forming a slurry; (b) heating the slurry to obtain a solution of the Compound (I) in the NMP; (c) polish filtering the solution to obtain a filtrate; (d) heating the filtrate; (e) adding 30 mL of IPA to the heated filtrate; (f) allowing the temperature of the result of (e) to cool, and then adding seeds of Compound (I) in an amount of 1 wt %; (g) aging the result of (f); (h) adding 60 mL of IPA to the result of (g); (i) cooling the result of (h) to obtain a cold slurry; (j) aging the cold slurry; (k) filtering the aged cold slurry to obtain crystalline solids; (l) washing the crystalline solids twice with 40 mL of IPA each time, to obtain a wet cake; and (m) drying the wet cake to obtain crystalline Form A of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl) amino)-N-(methyl-d 3 )pyridazine-3-carboxamide.

2 . The method according to claim 1 , wherein in (b), the slurry is heated to 70° C.

3 . The method according to claim 2 , wherein in (c), the polish filtering is performed at a temperature in the range of 62.5° C. to 85° C.

4 . The method according to claim 3 , wherein in (d), the filtrate is heated to 70° C., and wherein in (f), the temperature of the result of (e) is allowed to cool to 70° C.

5 . The method according to claim 4 , wherein in (g), the result of (f) is aged for 1 hour at 70° C.

6 . The method according to claim 5 , wherein in (h), the IPA is added over one hour.

7 . The method according to claim 6 , wherein in (i), the result of (h) is cooled to −10° C. over 3.5 hours, and wherein in (j), the cold slurry is aged at −10° C. for 12 hours.

8 . The method according to claim 7 , wherein in (m), the drying is performed in a vacuum oven at a temperature of from 50° C. to 100° C.

Assignees

• Bristol Myers Squibb Co

Inventors

• Zhang Yanlei
• Galella Michael A

Classifications

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07D249/08 Primary

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C07D237/24

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• C07C211/09

  Diamines · CPC title

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title