- 2-(Dimethylaminomethyl)-tetrahydroisoxazolopyridobenzazepine derivatives. Synthesis of a new 5-HT(2C) antagonist with potential anxiolytic properties.
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Following the program started at Johnson & Johnson Pharmaceutical Research & Development searching for 5-HT(2A/2C) antagonists, we now report on the synthesis of 2-(dimethylaminomethyl)-2,3,3a,8-tetrahydroisoxazolo[3,2-a]pyrido[3,4-c]-[2]benzazepine and 2-(dimethylaminomethyl)-2,3,3a,8-tetrahydroisoxazolo[3,2-a]pyrido[3,2-c]-[2]benzazepine. A new method for the synthesis of pyridobenzazepines is described as well. The affinities for several receptors as well as the mCPP antagonistic activity of the compounds synthesised are described.
- Andres, J Ignacio,Alonso, Jose M,Fernandez, Javier,Iturrino, Laura,Martinez, Pedro,Meert, Theo F,Sipido, Victor K
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p. 3573 - 3577
(2007/10/03)
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- Synthesis of 5H-pyrido[2,3-c]-2-benzazepines
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The title compounds can be obtained by two different ways: Ring closure of 2-benzazepine enaminonitrile 1 and the C2-building blocks 2, 7 and 8 gives rise to the title compounds 6, 9 and 10. - The second way starts with Wolff-Kishner-reduction of the 2-amino-3-benzoylpyridines 16a,b to the 2-amino-3-benzylpyridines 18a,b. Benzoylation of 18a,b leads to the dibenzoylated compounds 20 and 21, respectively, which can be transformed to the monobenzoylated pyridines 22 resp. 23. Applying the Bischler-Napieralski-reaction on 22a,b and 23a,b leads to the 5H-pyrido[2,3-c]-2-benzazepines 24a,b and 25a,b. By means of 1H-, 13C- and 15N-NMR-data it is demonstrated that ethyl benzoylcyanacetimidate (12a) exists as benzoylketene-O,N-acetal 12a AE.
- Troschutz,Grun
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p. 225 - 231
(2007/10/02)
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- Bisubstrate reaction templates. Examination of the consequences of identical versus different binding sites
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A reaction template (1≈9) possessing two binding sites is described. The template was designed to use hydrogen bonding to simultaneously (but transiently) bind two substrates, giving rise to a ternary complex (2≈12), which positions the substrates in an o
- Ross Kelly,Bridger, Gary J.,Zhao, Chen
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p. 8024 - 8034
(2007/10/02)
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