Salt of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate and crystal form thereof
AssigneeDong-A St Co., Ltd.
InventorsWoo Young Kwak, Chang-Yong Shin, Punna Reddy Ullapu, Sun-Ho Choi, Min-Jung Lee, Ji-Su Kim
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Abstract
The present invention relates to a novel salt of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate and a crystal form thereof. Also, the novel salt of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate and the crystal form thereof according to examples of the present invention have remarkably excellent stability, hygroscopicity and solubility.
Claims32
An (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate represented by a following formula 1:
A form I of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate, wherein an X-ray powder diffraction (XRPD) pattern comprises at least three diffraction peaks selected from the group consisting of diffraction angles 2θ of 13.402±0.2°, 14.300±0.2°, 18.519±0.2°, 19.577±0.2° and 21.499±0.2°.
A form II of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate, wherein the XRPD pattern comprises at least three diffraction peaks selected from the group consisting of diffraction angles 2θ of 13.439±0.2°, 14.481±0.2°, 18.501±0.2°, 21.779±0.2° and 23.358±0.2°.
A form III of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate, wherein the XRPD pattern comprises at least three diffraction peaks selected from the group consisting of diffraction angles 2θ of 10.720±0.2°, 11.018±0.2°, 14.239±0.2°, 17.880±0.2° and 21.440±0.2°.
A form IV of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate, wherein the XRPD pattern comprises at least three diffraction peaks selected from the group consisting of diffraction angles 2θ of 16.642±0.2°, 17.839±0.2°, 20.981±0.2°, 21.580±0.2° and 22.701±0.2°.
A form V of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate, wherein the XRPD pattern comprises at least three diffraction peaks selected from the group consisting of diffraction angles 2θ of 10.925±0.2°, 14.200±0.2°, 20.559±0.2° and 21.396±0.2°.
A form VI of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate, wherein the XRPD pattern comprises at least three diffraction peaks selected from the group consisting of diffraction angles 2θ of 10.127±0.2°, 10.893±0.2°, 11.751±0.2° and 17.978±0.2°.
A form VII of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate, wherein the XRPD pattern comprises at least three diffraction peaks selected from the group consisting of diffraction angles 2θ of 8.169±0.2°, 8.847±0.2°, 11.071±0.2° and 13.156±0.2°.
A form VIII of (R)-(1-methylpyrrolidine-3-yl)methyl(3′-chloro-4′-fluoro-[1,1′-biphenyl]-2-yl)carbamate oxalate, wherein the XRPD pattern comprises at least three diffraction peaks selected from the group consisting of diffraction angles 2θ of 8.903±0.2°, 13.090±0.2°, 14.347±0.2° and 15.871±0.2°.
Dependencies are inferred from the claim text.