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US 2017/0320852 A1Published application
Maleate salts of (e)-n--4-(dimethylamino)-2-butenamide and crystalline forms thereof
AssigneeWyeth
InventorsQuinhong Lu, Mannching Sherry Ku, Warren Chew, Gloria Cheal, Anthony F. Hadfield, Mahmoud Mirmehrabi
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Abstract
The present invention relates to maleate salt forms of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinollnyl}-4-(dimethylamino)-2-butenamide, methods of preparing crystalline maleate salt forms, the associated compounds, and pharmaceutical compositions containing the same. The maleate salts are useful in treating cancers, particularly those affected by kinases of the epidermal growth factor receptor family.
Claims25
1-35. (canceled)
A method of treating cancer, comprising:
- administering to a patient in need thereof neratinib formulated as a crystalline form of anhydrous (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide maleate;
- wherein:
- i) the crystalline form of anhydrous (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide maleate is characterized by X-ray diffraction peaks at the following angles)(±0.20°) of 2Theta in its X-ray diffraction pattern comprising 6.16, 7.38, 8.75, 12.61, 14.65, and 15.75;
- and
- ii) when administered to a patient, the formulation of the crystalline form of anhydrous (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide maleate produces at least a two-fold greater area under the curve, relative to neratinib in a free base formulation.
2 more elements
A method of treating cancer, comprising:
- administering to a patient in need thereof neratinib formulated as a crystalline form of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide maleate, monohydrate;
- wherein:
- i) the crystalline form of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide maleate, monohydrate, is characterized by X-ray diffraction peaks at the following angles)(±0.20°) of 2Theta in its X-ray diffraction pattern comprising 6.53, 8.43, 12.19, 12.47, 13.01, 16.76, and 21.11;
- and
- ii) when administered to a patient, the formulation of the crystalline form of anhydrous (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide maleate produces at least a two-fold greater area under the curve, relative to neratinib in a free base formulation.
2 more elements
Dependencies are inferred from the claim text.