Crystalline form of sofpironium bromide and preparation method thereof
AssigneesKaken Pharmaceutical Co., Ltd., Brickell Biotech, Inc.
InventorsKazuyoshi MARUBAYASHI, Masahito WATANABE, Herbert R. BRINKMAN
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Abstract
A cocrystal containing the 1′R-diastereomer and the 1′S-diastereomer of sofpironium bromide at a ratio of 1:3 (Form CO), a crystal mixture (for example, Form B) containing Form CO and a crystalline form of the 1′R-diastereomer (Form MN), and a method for preparing sofpironium bromide, which is suitable for manufacture of the crystal mixture are provided. Form CO and a crystalline form of sofpironium bromide containing Form CO (for example, Form B) have superior stability without hygroscopic property, and accordingly they can be preferably used as a raw material of medicaments.
Claims26
A stable co-crystal Form CO of sofpironium bromide, said co-crystal Form CO comprising in a 1:3 ratio:
- a) a compound shown as formula I-a
- and
- b) a compound shown as formula I-b
A stable crystal Form MN of a compound shown as formula I-a
- characterized by showing peaks at 7.1±0.1, 21.4±0.1, 22.3±0.1, and 24.5±0.1 as diffraction angles 2θ in a powder X-ray diffraction spectrum.
A crystal Form B being a mixture of crystal Form CO and crystal From MN, and characterized by showing peaks at 5.9±0.2, 7.2±0.2, 7.7±0.2, 11.1±0.2, 22.3±0.2, and 24.6±0.2 as diffraction angles 2θ in a powder X-ray diffraction spectrum.
A stable topical pharmaceutical composition which is made by mixing:
- a pharmaceutically effective amount of at least one crystal form of sofpironium bromide as an active pharmaceutical agent, said crystal form selected from the group consisting of Form CO, Form MN, and Form B, and
- a pharmaceutically acceptable carrier;
- wherein Form CO is a stable co-crystal form comprising in a 1:3 ratio:
- a) a compound shown as formula I-a
- and
- b) a compound shown as formula I-b
- wherein Form MN is a compound according to formula I-a
- characterized by showing peaks at 7.1±0.1, 21.4±0.1, 22.3±0.1, and 24.5±0.1 as diffraction angles 2θ in a powder X-ray diffraction spectrum;
- and
- wherein Form B is the mixture of Form CO and Form MN.
Dependencies are inferred from the claim text.