Formoterol process

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...

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Details

516 1, 516 77, 516104, 564443, 562585, A61K 3116, C07C23303

Patent

active

060403446

ABSTRACT:
A method is disclosed for the preparation of optically pure isomers of formoterol by the reaction of an optically pure 4-benzyloxy-3-formamidostyrene oxide with an optically pure 4-methoxy-.alpha.-methyl-N-(phenylmethyl)benzeneethanamine followed by debenzylation. Useful intermediates in the process are also disclosed, as are the novel L-tartrate salt of R,R-formoterol and pharmaceutical compositions thereof.

REFERENCES:
patent: 3994974 (1976-11-01), Murakami et al.
Hett et al. "Large Scale Synthesis of Enantio-and Diastereomerically Pure (R,R)--Formoterol" Organic Proc. Res. & Dev. 2, 96-99 (1998).
Hett et al. "Conformational Toolbox of Oxazaborolidine Catalysts in the Enantioselective . . . " Tet. Lett. 39, 1705-1708 (1998).
Hett et al. "Enantio-and Diastereoselective Synthesis of all Four Stereoisomers of Formoterol" Tet. Lett. 38, 1125-1128 (1997).
Murase et al. "New .beta.-Adrenoreceptor Stimulants. Studies on 3-Acylamino-4-hydroxy-. . . " Chem. Pharm. Bull. 25(6), 1368-1377 (1977).
Murase et al. "Absolute Configurations of Four Isomers of 3-Formamido-4-hydroxy-. . . " Chem. Pharm. Bull. 26(4), 1123-1129 (1978).
Trofast et al. "Steric Aspects of Agonism and Antagonism at .beta.-Adrenoceptors: Synthesis . . . " Chirality 3, 443-450 (1991).

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