11—[ (Z) -3- (dimethylamino) propylidene]—6,...

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

Reexamination Certificate

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C514S450000

Reexamination Certificate

active

07612219

ABSTRACT:
Process for the preparation of olopatadine (I), which comprises reacting a compound of formula (V) in the presence of a palladium catalyst to provide a compound of formula (VI), wherein the acid protecting group is removed to provide the compound of formula (I) and if desired, transformation into its salts.

REFERENCES:
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patent: 6638977 (2003-10-01), Madison et al.
Etsuo, Otaki et. al. “Synthesis and antiallergic activity of 11-(aminoalkylidene)-6,11-dihydrodibenz[b,e]oxepin derivatives.” Journal of Medicinal Chemistry, 1992 35(11), 2074-84.
Soederberg, Bjoern et. al. “Synthesis of fused indoles by sequential palladium-catalyzed Heck reaction and N-heteroannulation.” Tetrahedron, 2005, 61(15), 3637-3649.
Denieul, Marie-Pierre et. al. “Synthesis of the Benzophenone Fragment of Balanol via an Intramolecular Cyclization Event.” Journal of Organic Chemistry, 2000, 65(19), 6052-6060.
Finch, Harry, et al., “The Synthesis of a Conformationally Restrained, Combined Thromboxane Antagonist/Synthase Inhibitor Using an Intramolecular ‘Stille’-or ‘Grigg’-Palladium-Catalysed Cyclisation Strategy,” Tetrahedron Letters, 34(51): 8353-8356 (1993).
Chaudhuri, Gopeswar et al., “A highly regio- and stereoselective synthesis of (Z)-3-arylidene-2,3-dihydro-5H-1,4- benzodioxepin-5-ones and (Z)-3-arylidene-1,2,3,5-tetrahydro-4,1-benzoxazepin-5-ones through palladium-copper catalysis,” J. Chem. Soc. Perkin Trans. 1: 775-779 (2000).

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