- NOVEL METHOD FOR PRODUCING OPTICALLY ACTIVE PYRROLIDINE COMPOUND
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[Object] A novel method for producing an optically active pyrrolidine compound, which is useful as a production intermediate of a pharmaceutical, and a production intermediate thereof, is provided. [Means for Solution] According to the production method o
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- A practical and efficient synthesis of (3R,4S)-1-benzyl-4- phenylpyrrolidine-3- carboxylic acid via an aziridinium ion intermediate
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A practical and efficient synthesis of (3R,4S)-1-benzyl4-phenylpyr- rolidine-3-carboxylic acid (1), a key chiral building block for synthesis of biologically active compounds was established by utilizing a stereospecific and regioselective chlorination of in situ generated aziridinium ion, followed by a nitrile anion cyclization. Starting from commercially available (R)-styrene oxide and 3-(benzylamino)propionitrile, the four-step synthesis features a through process without purification of intermediates until isolation of crystalline 1. The robust, chromatography-free and reproducible synthesis of 1 achieved an 84% overall yield from (R)-styrene oxide. This highly efficient process was successfully demonstrated at pilot scale with 17 kg output of 1.
- Ohigashi, Atsushi,Kikuchi, Takashi,Goto, Shunsuke
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experimental part
p. 127 - 132
(2010/04/29)
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- NOVEL SPIROTROPANE COMPOUNDS AND METHODS FOR THE MODULATION OF CHEMOKINE RECEPTOR ACTIVITY
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Compounds according to formula (I): wherein the radical R2 represents a hydrogen atom or one of the following structures: R, and R7_9are as herein defined, and wherein ring A represents a 5 or 6 membered heteroring involvi
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Page/Page column 77-78
(2008/06/13)
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- Spirohydantoin compounds and methods for the modulation of chemokine receptor activity
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Novel compounds represented by formula (I): wherein R1, R2, R3 and R4 are as defined herein, and pharmaceutically acceptable salts, hydrates and solvates thereof, are useful for the modulation of CCR5 chemokine
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Page/Page column 14
(2010/02/15)
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- SPIRO COMPOUNDS AND METHODS FOR THE MODULATION OF CHEMOKINE RECEPTOR ACTIVITY
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Compounds of formula I insert formula I from claim 1 wherein X, Y, Z, W, R1 and R2 as defined herein, or pharmaceutically acceptable salts, hydrates or solvates thereof, are useful for the modulation of CCR5 chemokine receptor activity.
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Page/Page column 105-106
(2010/02/11)
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- 1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 1: Discovery of the pyrrolidine scaffold and determination of its stereochemical requirements
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A series of 1,3,4-trisubstituted pyrrolidines was discovered to have the ability to displace [125I]-MIP-1α from the CCR5 receptor expressed on Chinese hamster ovary (CHO) cell membranes. CCR5 activity was found to be dependent on the regiochemi
- Hale, Jeffrey J.,Budhu, Richard J.,Mills, Sander G.,MacCoss, Malcolm,Malkowitz, Lorraine,Siciliano, Salvatore,Gould, Sandra L.,DeMartino, Julie A.,Springer, Martin S.
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p. 1437 - 1440
(2007/10/03)
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