NNC 45-0781
| Molecular Formula | C27H29NO3 |
| Molecular Weight | 415.5241 |
CAS 207277-66-5
- 2H-1-Benzopyran-7-ol, 3,4-dihydro-3-phenyl-4-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, cis-(-)-
- (3S,4R)-3,4-Dihydro-3-phenyl-4-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-2H-1-benzopyran-7-ol
2H-1-Benzopyran-7-ol, 3,4-dihydro-3-phenyl-4-(4-(2-(1-pyrrolidinyl)ethoxy)phenyl)-, (3S,4R)-
- OriginatorNovo Nordisk
- ClassOsteoporosis therapies; Pyrrolidines; Small molecules
- Mechanism of ActionSelective estrogen receptor modulators
PATENT
WO 9818776
WO 9818771
WO 2003063859
A quantitative structure activity relationship study on cis-3,4-diaryl hydroxy chromones as high affinity partial agonists for the estrogen receptor
Chemistry: An Indian Journal (2003), 1, (3), 207-214
SYN 1
EP 0937057; WO 9818771, EP 0937060; WO 9818776
http://www.drugfuture.com/synth/syndata.aspx?ID=268276
Coumarin (III) was prepared by condensation of benzophenone (I) with phenylacetic acid (II) in the presence of Ac2O and Et3N. Reduction of the lactone function of (III) with LiAlH4, followed by acidic treatment furnished diaryl chromene (IV). Subsequent hydrogenation of (IV) over Pd/C gave rise to the racemic cis chromane (V), which was O-alkylated with 1-(2-chloroethyl) pyrrolidine (VI) producing the corresponding (pyrrolidinyl)ethoxy derivative. Resolution by means of active ditoluoyl tartaric acid yielded the desired (-)-enantiomer (VII). Finally…
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