Crystalline form of a benzimidazole-carboxamide medicinal...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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07622587

ABSTRACT:
The invention provides crystalline forms of the novel benzimidazole-carboxamide 5-HT4receptor agonist compound, 4-(4-{[(2-isopropyl-1H-benzoimidazole-4-carbonyl)amino]methyl}-piperidin-1-ylmethyl)piperidine-1-carboxylic acid methyl ester. The invention also provides pharmaceutical compositions comprising the crystalline compound, methods of using the compound to treat diseases associated with 5-HT4receptor activity, and processes useful for preparing crystalline forms of the compound.

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Lopez-Rodriguez et al., “3-D-QSAR/CoMFA and Recognition Models of Benzimidazole Derivatives at the 5-HT4Receptor”, Bioorganic & Medicinal Chemistry Letters, 11, pp. 2807-2811(2001).
Lopez-Rodriguez et al., “Benzimidazole Derivates. Part 1: Synthesis and Structure-Activity Relationships of New Benzimidazole-4-carboxamides and Carboxylates as Potent and Selective 5-HT4Receptor Antagonists”, Bioorganic & Medicinal Chemistry, 7, pp. 2271-2281 (1999).
Lopez-Rodriguez et al., “Benzimidazole Derivatives. 3. 3D-QSAR/CoMFA Model and Computational Simulation for the Recognition of 5-HT4Receptor Antagonists”, J. Med. Chem., 45, pp. 4806-4815 (2000).
Lopez-Rodriguez et al., “Benzimidazone derivatives 4. The recognition of the voluminous substituent attached to the basic amino group of 5-HT4receptor antagonists”, Journal of Computer-Aided Molecular Design, 17, pp. 515-524 (2003).
Lopez-Rodriguez et al., “Design and Synthesis of New Benzimidazole-Arylpiperazine Derivatives Acting as Mixed 5-HT1A/5-HT3Ligands”, Bioorganic & Medicinal Chemistry Letters, 13, pp. 3177-3180 (2003).
Lopez-Rodriguez et al., “Study of the bioactive conformation of novel 5-HT4receptor ligands: influence of an intramolecular hydrogen bond”, Tetrahedron, 57, pp. 6745-6749 (2001).
Harada et al., “NovelN-[1-(1-Substituted 4-Piperidinylmethyl)-4-piperidinyl]benzamides as Potent Colonic Prokinetic Agents”, Bioorganic & Medicinal Chemistry Letters 12, pp. 967-970 (2002).

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