US 12,291,517 B2
Crystalline 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
Daniel Richard Roberts, Robbinsville, NJ (US)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Filed by Bristol-Myers Squibb Company, Princeton, NJ (US)
Filed on Jan. 29, 2023, as Appl. No. 18/102,761.
Application 18/102,761 is a continuation of application No. 17/058,698, granted, now 11,613,529, previously published as PCT/US2019/034534, filed on May 30, 2019.
Claims priority of provisional application 62/678,451, filed on May 31, 2018.
Prior Publication US 2023/0242515 A1, Aug. 3, 2023
Int. Cl. C07D 403/12 (2006.01)
CPC C07D 403/12 (2013.01) [C07B 2200/05 (2013.01); C07B 2200/13 (2013.01)] 18 Claims
 
1. A method of treating a disease in a human subject, the method comprising administering to the human 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl) phenyl) amino)-N-(methyl-d3) pyridazine-3-carboxamide,
wherein the disease is selected from psoriasis, psoriatic arthritis, lupus, lupus nephritis, Sjögren's syndrome, inflammatory bowel disease, Crohn's disease, and ankylosing spondylitis, and
wherein the 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl) phenyl) amino)-N-(methyl-d3) pyridazine-3-carboxamide comprises crystalline Form B of 6-(cyclopropanecarboxamido)-4-((2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl) phenyl) amino)-N-(methyl-d3) pyridazine-3-carboxamide, wherein the crystalline Form B is characterized by at least one of the following:
(i) a powder x-ray diffraction (PXRD) pattern comprising 2θ values in degrees (CuKα) at 8.1±0.2 and 12.8±0.2; and three or more 2θ values in degrees (CuKα) selected from: 8.9±0.2; 10.4±0.2; 14.9±0.2; 16.4±0.2 and 18.4±0.2; wherein the PXRD pattern of crystalline Form B is measured at a temperature of about 25° C.;
(ii) a powder x-ray diffraction (PXRD) pattern comprising four or more 2θ values in degrees (CuKα) selected from: 8.1±0.2; 8.9±0.2; 10.4±0.2; 12.8±0.2; 14.9±0.2; 16.4±0.2 and 18.4±0.2, wherein the PXRD pattern of crystalline Form B is measured at a temperature of about 25° C.;
(iii) an observed powder x-ray diffraction pattern substantially as shown in FIG. 1;
(iv) a powder x-ray diffraction pattern comprising 2θ values in degrees (CuKα) at 8.1±0.2 and 112.8±0.2, measured at a temperature of about 25° C.; and a 13C ssNMR spectrum comprising five or more chemical shift values in ppm (a11±0.2) selected from: 175.0; 167.6; 156.3; 150.9; 147.2; 144.4; 142.7; 138.2; 136.3; 125.0; 121.6; 117.5; 98.3; 59.8; 40.6; 26.9; 15.6; 10.3 and 7.2; wherein the spectrum of crystalline Form B is measured at a temperature of about 280° K;
(v) unit cell parameters substantially equal to the following:
a=8.55+0.05 Å
b=11.60+0.05 Å
c=12.00±0.05 Å
a=114.3±0.5°
β=94.1±0.5°
γ=93.31±0.5°
Space group: P-1
Molecules per unit cell (Z): 2
wherein the unit cell parameters of crystalline Form B are measured at a temperature of about 25° C.