Crystalline D-isoglutamyl-D-tryptophan and the mono ammonium salt of D-isoglutamyl-D-tryptophan
AssigneeApotex Technologies Inc.
InventorsTim Fat Tam, Blaise N'Zemba, Regis Leung-Toung, Yingsheng Wang, Yanqing Zhao, Lily Yu
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Abstract
A process for making pure crystalline D-isoglutamyl-D-tryptophan is provided which includes the step of deprotecting essentially pure N-tert-butoxycarbonyl-D-isoglutamyl-D-tryptophan or its diester to yield essentially pure D-isoglutamyl-D-tryptophan. A process is also provided for the preparation of pure mono ammonium salt of D-isoglutamyl-D-tryptophan from essentially pure N-tert-butoxycarbonyl-D-isoglutamyl-D-tryptophan. D-isoglutamyl-D-tryptophan, ammonium salt (1:1) is a stable pharmaceutical solid.
Claims24
Crystalline H-D-iGlu-D-Trp-OH, ammonium salt (1:1) characterized by the x-ray powder diffraction pattern as illustrated in FIG. 2.
Crystalline H-D-iGlu-D-Trp-OH, ammonium salt (1:1) characterized by the following X-ray powder diffraction pattern expressed in terms of inter-planar distances d, Bragg's angle 2 theta, and relative intensity (expressed as a percentage with respect to the most intense ray):
- Angle [°2 theta]
- d-value [Å]
- Rel. Int [%]
- 9.29
- 9.517
- 4.1
- 12.19
- 7.258
- 4.5
- 13.93
- 6.354
- 76.2
- 15.17
- 5.837
- 27.4
- 16.49
- 5.371
- 9.8
- 17.18
- 5.157
- 3
- 18.56
- 4.778
- 31.6
- 18.88
- 4.696
- 10.5
- 20.02
- 4.431
- 100
- 22.28
- 3.986
- 3
- 23.31
- 3.814
- 4.6
- 23.66
- 3.757
- 9.8
- 24.03
- 3.7
- 52.9
- 24.37
- 3.649
- 26.3
- 25.07
- 3.549
- 11.4
- 25.61
- 3.475
- 5.6
- 25.96
- 3.43
- 5
- 27.62
- 3.227
- 29.7
- 28.12
- 3.17
- 55.7
- 28.49
- 3.131
- 12.2
- 29.52
- 3.023
- 23.1
- 30.27
- 2.951
- 3.7
- 30.64
- 2.915
- 7.9
- 31.31
- 2.854
- 11.8
- 31.7
- 2.821
- 29.6
- 32.16
- 2.781
- 19.2
- 32.81
- 2.728
- 16
- 33.78
- 2.652
- 7.4
- 34.14
- 2.625
- 5.1
- 35.76
- 2.509
- 16
- 36.94
- 2.431
- 11.6
- 37.58
- 2.391
- 25.6
- 38.03
- 2.364
- 12.5
- 39.22
- 2.295
- 1.9.
Crystalline H-D-iGlu-D-Trp-OH, ammonium salt (1:1) having an X-ray powder diffraction pattern comprising peaks at 2θ angles of approximately 13.93, 20.02, 24.03 and 28.12 degrees.
Crystalline H-D-iGlu-D-Trp-OH, ammonium salt (1:1) having an X-ray powder diffraction pattern comprising peaks at approximately 9.29, 12.19, 13.93, 15.17, 16.49, 17.18, 18.56, 18.88, 20.02, 22.28, 23.31, 23.66, 24.03, 24.37, 25.07, 25.61, 25.96, 27.62, 28.12, 28.49, 29,52, 30.27, 30.64, 31.31, 31.70, 32.16, 32.81, 33.78, 34.14, 35.76, 36.94, 37.58, 38.03 and 39.22 degrees 2θ.
Crystalline H-D-iGlu-D-Trp-OH, ammonium salt (1:1) characterized by the infrared absorption spectrum as illustrated in FIG. 4.
Dependencies are inferred from the claim text.