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X-ray powder diffraction data for alogliptin benzoate, C18H21N5O2·C7H6O2

Published online by Cambridge University Press:  15 December 2016

Xia Zeng ,
Qing Wang ,
Xin Nuo Xiong ,
Qiao Hong Du  and
Hui Li
Xia Zeng
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Qing Wang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Xin Nuo Xiong
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Qiao Hong Du
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Hui Li*
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
*
a) Author to whom correspondence should be addressed. Electronic mail: lihuilab@sina.com

Abstract

X-ray powder diffraction data, unit-cell parameters, and space group for alogliptin benzoate, C18H21N5O2·C7H6O2, are reported [a = 28.8260(8) Å, b = 9.9654(4) Å, c = 8.1477(8) Å, α = 90, β = 90, γ = 90°, unit-cell volume V = 2340.57 Å3, Z = 4, ρ cal = 1.3097 g cm−3, and space group P212121]. All measured lines were indexed and are consistent with the P212121 space group, No detectable impurities were observed.

Keywords

X-ray powder diffractionalogliptin benzoate

Information

Type
Data Reports
Information
Powder Diffraction , Volume 32 , Issue 1 , March 2017 , pp. 49 - 52
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Copyright
Copyright © International Centre for Diffraction Data 2016 

I. INTRODUCTION

Alogliptin benzoate (Nesina®) (Figure 1), systematic name 2-[6-[3(R)-Aminopiperidin-1-yl]-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl]benzonitrile benzoate, is a newly developed DPP-4 inhibitor (Saisho, Reference Saisho2015). The efficacy of the compound as a highly selective dipeptidyl peptidase-4 (DPP-4) inhibitor has been demonstrated (Feng et al., Reference Feng, Zhang and Wallace2007). DPP-4 inhibitors (McIntosh et al., Reference McIntosh, Demuth, Pospisilik and Pederson2005) metabolize the insulin-increasing hormones glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic peptide. Therefore, alogliptin benzoate has become one of the most promising type-2 diabetes mellitus drugs.

Figure 1.

Structural formula of alogliptin benzoate.

The single crystallographic data of alogliptin benzoate was reported by Gelbrich et al. (Reference Gelbrich, Griesser and Kahlenberg2013), the values of cell parameters were a = 28.4593(6) Å, b = 9.8727(2) Å, c = 8.0666(2) Å, α = 90, β = 90, γ = 90°, unit-cell volume V = 2266.47(9) Å3, Z = 4, ρ cal = 1.353 g cm−3, and space group P212121. Presently, the detailed X-ray powder diffraction data for alogliptin benzoate have not been reported.

II. EXPERIMENTAL

A. Sample preparation

The title compound alogliptin benzoate, with purity of more than 99%, was from Wuhan E-ternity Technologies Co., Ltd. (Shanghai, China). It was recrystallized in methanol and dried. The sample melting point and measured density of the title compound are 183–184 °C and 1.353 g cm−3, respectively. Moreover, the sample was then ground into powder and mounted on a flat zero background plate.

B. Diffraction data collection and reduction

X-ray powder diffraction measurement was performed at room temperature using an X'Pert PRO diffractometer (PANalytical Co., Ltd., Netherlands) with a PIXcel one-dimensional (1D) detector and CuKα radiation (generator setting: 40 kV and 40 mA). The diffraction data were collected over the angular range from 4° to 50°2θ with a step size of 0.013 13°2θ and a counting time of 50 ms step−1. Figure 2 shows the Powder X-ray diffraction pattern of the compound.

Figure 2.

Powder X-ray diffraction pattern of alogliptin benzoate, using CuKα1 radiation (λ = 1.540 56 Å).

The software package Material Studio 8.0 (Accelrys Co., Ltd., CA, USA) was used to process the data in the Analytical & Testing Center (Sichuan University, Chengdu, China). The X-ray powder diffraction pattern was pre-treated by subtracting the background, smoothing, and stripping off the Kα 2 component (Li et al., Reference Li, Wu, Pan, Cheng and Li2014). Automatic indexing results were obtained by the DICVOL91 method (Boultif and Louër, Reference Boultif and Louër1991). Then the indexing result was refined using the Pawley method (Wang et al., Reference Wang, Sun, Li, Guo and Li2015). Pawley refinement converged to R wp = 6.46%.

III. RESULTS

The figure-of-merit was achieved: F 24 = 44.7 (0.0080, 76) (Smith and Snyder, Reference Smith and Snyder1979) and M 24 = 16.8 (de Wolff, Reference de Wolff1968). Pawley refinement results confirmed that the title compound is orthorhombic with space group P212121 and unit-cell parameters: a = 28.8260(8) Å, b = 9.9654(4) Å, c = 8.1477(8) Å, α = 90, β = 90, γ = 90°, unit-cell volume V = 2340.57 Å3, Z = 4, and ρ cal = 1.3097 g cm−3. The values of 2θ obs, d obs, I obs, h, k, l, 2θ cal, d cal, I cal, and Δ2θ are listed in Table I.

Table I.

X-ray powder diffraction data for the alogliptin benzoate, C18H21N5O2·C7H6O2. a = 28.8260(8) Å, b = 9.9654(4) Å, c = 8.1477(8) Å, α = 90°, β = 90°, γ = 90°, unit-cell volume V = 2340.57 Å3, Z = 4, ρ cal = 1.3097 g cm−3, and space group P212121. The d-values were calculated using CuKα 1 radiation (λ = 1.54056 Å).

The comparison of this pattern with the calculated pattern of single-crystal data is shown in online Figure S1. The results showed that both single-crystal and powder diffraction methods can get similar structure data.

SUPPLEMENTARY MATERIAL

The supplementary material for this article can be found at https://doi.org/10.1017/S0885715616000592.

ACKNOWLEDGEMENTS

This work was supported by the National Development and Reform Commission and Education of China (Grant no. 2014BW011) and the Large-scale Science Instrument Shareable Platform Construction of Sichuan Province (Grant no. 2015JCPT0005-15010102).

References

Boultif, A. and Louër, D. (1991). “Indexing of powder diffraction patterns for low-symmetry lattices by the successive dichotomy method,” J. Appl. Crystallogr. 24, 987–993.CrossRefGoogle Scholar
de Wolff, P. M. (1968). “A simplified criterion for the reliability of a powder pattern,” J. Appl. Crystallogr. 1, 108–113.CrossRefGoogle Scholar
Feng, J., Zhang, Z., and Wallace, M. B. (Eds) (2007). “Discovery of alogliptin: a potent, selective, bioavailable, and efficacious inhibitor of dipeptidyl peptidase IV”, J. Med. Chem. 50, 2297–2300.CrossRefGoogle ScholarPubMed
Gelbrich, T., Griesser, U. J., and Kahlenberg, V. (2013). “Alogliptin and its benzoate salt,” J. Acta Crystallogr. 69, 674–678.Google ScholarPubMed
Li, S. S., Wu, X. Q., Pan, Q. Q., Cheng, Q., and Li, H. (2014). “Comparison of the accuracy of powder and single crystal X-ray diffraction techniques in determining organic crystal structure,” Chin. Sci. Bull. 59, 497–501.CrossRefGoogle Scholar
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Saisho, Y. (2015). “Alogliptin benzoate for management of type 2 diabetes”, J. Vasc. Health Risk Manage. 11, 229–243.CrossRefGoogle ScholarPubMed
Smith, G. S. and Snyder, R. L. (1979). “FN: a criterion for rating powder diffraction patterns and evaluating the reliability of powder indexing,” J. Appl. Crystallogr. 12, 60–65.CrossRefGoogle Scholar
Wang, Q., Sun, Q. M., Li, S. S., Guo, L. Q., and Li, H. (2015). “X-ray powder diffraction data for drospirenone, C24H30O3 ,” Powder Diffr. 31(1), 63–65.CrossRefGoogle Scholar
Figure 0

Figure 1. Structural formula of alogliptin benzoate.

Figure 1

Figure 2. Powder X-ray diffraction pattern of alogliptin benzoate, using CuKα1 radiation (λ = 1.540 56 Å).

Figure 2

Table I. X-ray powder diffraction data for the alogliptin benzoate, C18H21N5O2·C7H6O2. a = 28.8260(8) Å, b = 9.9654(4) Å, c = 8.1477(8) Å, α = 90°, β = 90°, γ = 90°, unit-cell volume V = 2340.57 Å3, Z = 4, ρcal = 1.3097 g cm−3, and space group P212121. The d-values were calculated using CuKα1 radiation (λ = 1.54056 Å).

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