Synthesis of a Potent hNK-1 Receptor Antagonist via an SN2 Reaction of an Enantiomerically Pure α-Alkoxy Sulfonate

2005 ◽  
Vol 7 (1) ◽  
pp. 55-58 ◽  
Author(s):  
Todd D. Nelson ◽  
Jonathan D. Rosen ◽  
Jacqueline H. Smitrovich ◽  
Joseph Payack ◽  
Bridgette Craig ◽  
...  
Keyword(s):  
Receptor Antagonist ◽  
Enantiomerically Pure ◽  
Sn2 Reaction

Synthesis of a Potent hNK-1 Receptor Antagonist (I) via an SN2 Reaction of an Enantiomerically Pure ?-Alkoxy Sulfonate.

ChemInform ◽  
2005 ◽  
Vol 36 (17) ◽  
Author(s):  
Todd D. Nelson ◽  
Jonathan D. Rosen ◽  
Jacqueline H. Smitrovich ◽  
Joseph Payack ◽  
Bridgette Craig ◽  
...  
Keyword(s):  
Receptor Antagonist ◽  
Enantiomerically Pure ◽  
Sn2 Reaction

Enantioselective Synthesis of a 2,2-Disubstituted Tetrahydro-3- benzazepine as Novel NMDA Receptor Antagonist

2010 ◽  
Vol 65 (2) ◽  
pp. 191-196 ◽  
Author(s):  
Syed Masood Husain ◽  
Roland Fröhlich ◽  
Dirk Schepmann ◽  
Bernhard Wünsch
Keyword(s):  
Crystal Structure ◽  
Nmda Receptor ◽  
Receptor Antagonist ◽  
Binding Site ◽  
Nmda Receptor Antagonist ◽  
Crystal Structure Analysis ◽  
Enantioselective Synthesis ◽  
Enantiomerically Pure ◽  
X Ray ◽  
Stereogenic Center

The tricyclic oxazolidines trans-4 and cis-4 were interconverted upon treatment with allyltrimethylsilane/ TiCl4. The oxazolidine trans-4 was diastereoselectively reacted with PhMgBr to yield the 4,4-disubstituted 3-benzazepinone 6, along with two side products. An X-ray crystal structure analysis of 6 proved the (R)-configuration of the stereogenic center C-4 and thus the retention of configuration. Reduction of 6 with AlCl3/LiAlH4 (1/3) followed by hydrogenolysis with H2, Pd/C resulted in the formation of enantiomerically pure 2-methyl-2-phenyl-tetrahydro-3-benzazepine 11 which has a moderate affinity (Ki = 496 nM) to the PCP binding site of the NMDA receptor.

An efficient synthesis of enantiomerically pure 2-[(2R)-arylmorpholin-2-yl]ethanols, key intermediates of tachykinin receptor antagonist

1998 ◽  
Vol 9 (18) ◽  
pp. 3251-3262 ◽  
Author(s):  
Takahide Nishi ◽  
Koki Ishibashi ◽  
Katsuyoshi Nakajima ◽  
Yukiko Iio ◽  
Tetsuya Fukazawa
Keyword(s):  
Receptor Antagonist ◽  
Efficient Synthesis ◽  
Enantiomerically Pure ◽  
Tachykinin Receptor

ChemInform Abstract: An Efficient Synthesis of Enantiomerically Pure 2-[(2R)-Arylmorpholin-2-yl]ethanols, Key Intermediates of Tachykinin Receptor Antagonist.

ChemInform ◽  
2010 ◽  
Vol 30 (10) ◽  
pp. no-no
Author(s):  
Takahide Nishi ◽  
Koki Ishibashi ◽  
Katsuyoshi Nakajima ◽  
Yukiko Iio ◽  
Tetsuya Fukazawa
Keyword(s):  
Receptor Antagonist ◽  
Efficient Synthesis ◽  
Enantiomerically Pure ◽  
Tachykinin Receptor

Colonic effects of TAK-637: A novel NK, receptor antagonist

2001 ◽  
Vol 120 (5) ◽  
pp. A331-A331
Author(s):  
K VENKOVA ◽  
K TYLER ◽  
D SUTKOWSKIMARKMANN
Keyword(s):  
Receptor Antagonist ◽  
Nk Receptor
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