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|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.|
|Inventor(s):||Gao; Yun (Southborough, MA), Hett; Robert (Aarau, CH), Fang; Kevin Q. (Wellesley, MA), Wald; Stephen A. (Sudbury, MA), Redmon; Martin P. (Marlborough, MA), Senanayake; Chris Hugh (Shrewsbury, MA)|
|Assignee:||Sepracor Inc. (Marlborough, MA)|
1. Crystalline R,R-formoterol L-(+)-tartrate.
2. Solid R,R-formoterol L-(+)-tartrate having a melting point greater than 179.degree. C.
3. A polymorph of R,R-formoterol L-(+)-tartrate having a transition point in differential scanning calorimetry of about 193.degree. C. and a solubility in water at 25.degree. C. of about 15 mg/mL.
4. A polymorph of R,R-formoterol L-(+)-tartrate having a transition point in differential scanning calorimetry of about 180.degree. C. and a solubility in water at 25.degree. C. of greater than 25 mg/mL.
5. A pharmaceutical composition comprising R,R-formoterol L-(+)-tartrate and a pharmaceutically acceptable carrier.
6. A pharmaceutical composition according to claim 5 wherein said pharmaceutically acceptable carrier is substantially lactose-free.
7. An aerosol pharmaceutical composition according to claim 5.
8. An oral pharmaceutical composition according to claim 5.
9. An oral pharmaceutical composition according to claim 8 in the form of a tablet, capsule or syrup.
10. A dry powder pharmaceutical composition for inhalation according to claim 5 comprising R,R-formoterol L-(+)-tartrate and a dry, solid carrier having a mean particle size between 1 .mu.m and 100 .mu.m.
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