Process for the preparation of delmopinol and derivatives...

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent

Reexamination Certificate

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Reexamination Certificate

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07910730

ABSTRACT:
A process for the preparation of delmopinol (3-(4-propylheptyl)-4-morpholinethanol) or a derivative or a pharmaceutically acceptable salt, or a solvate thereof, including a hydrate, comprises reacting oxazolidin [2,3-c] morpholine and a Grignard reagent, and optionally converting the delmopinol (or derivative) free base into a pharmaceutically acceptable salt. The oxazolidin [2,3-c] morpholine and the Grignard reagent are useful as intermediates in the production process.

REFERENCES:
patent: 4595751 (1986-06-01), Blanc
patent: 5155220 (1992-10-01), Hernestam et al.
patent: 0 038 785 (1981-10-01), None
patent: WO 90/14342 (1990-11-01), None
Mealy N., et al. “Delmopinol hydrochloride. Dental plaque formation inhibitor, treatment of gingivitis”Drugs of the Future, Aug. 1996, pp. 787-791, vol. 21, No. 8.
Poerwono H., et al. “Stereocontrolled Preparation of cis- and trans-2,6-Dialkylpiperidines via Diastereoselective Reaction of 1-Aza-4-oxabicyclo[4.3.0] nonane Derivatives with Grignard Reagents”Tetrahedron, Nov. 12, 1998, pp. 13955-13970, vol. 54, No. 46.

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