191673-56-0Relevant academic research and scientific papers
Asymmetric synthesis of an antagonist of neurokinin receptors: SSR 241586
Metro, Thomas-Xavier,Cochi, Anne,Gomez Pardo, Domingo,Cossy, Janine
scheme or table, p. 2594 - 2602 (2011/06/20)
SSR 241586 is a 2,2-disubstituted morpholine, developed by Sanofi-Aventis, which is active in the treatment of schizophrenia and irritable bowel syndrome (IBS). Different strategies have been studied to synthesize this molecule and among the strategies an
Enantioselective synthesis of SSR 241586 by using an organo-catalyzed Henry reaction
Cochi, Anne,Metro, Thomas-Xavier,Pardo, Domingo Gomez,Cossy, Janine
supporting information; experimental part, p. 3693 - 3695 (2010/10/20)
An organo-catalyzed Henry reaction, applied to an α-keto ester, has allowed the enantioselective synthesis of SSR 241586, a 2,2-disubstituted morpholine active in the treatment of schizophrenia and irritable bowel syndrome (IBS).
Efficient synthesis of a key intermediate of neurokinin receptor antagonists using a bifunctional asymmetric catalyst
Takamura, Makoto,Yabu, Kazuo,Nishi, Takahide,Yanagisawa, Hiroaki,Kanai, Motomu,Shibasaki, Masakatsu
, p. 353 - 356 (2007/10/03)
We report herein an efficient synthetic method for the preparation of 2-[(2R)-arylmorpholin-2-yl]ethanol, a key intermediate of neurokinin receptor antagonists. Catalytic asymmetric cyanosilylation of ketone 3 using titanium complex 4 was employed to introduce the required stereochemistry.
Acylated hetero-alicyclic derivatives
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, (2008/06/13)
A compound of formula (I), a pharmaceutically acceptable salt or ester or other derivative thereof: R1is optionally substituted cycloalkyl or optionally substituted saturated heterocyclic group. R2is optionally substituted aryl or op
Combined tachykinin receptor antagonist: Synthesis and stereochemical structure-activity relationships of novel morpholine analogues
Nishi, Takahide,Ishibashi, Koki,Takemoto, Toshiyasu,Nakajima, Katsuyoshi,Fukazawa, Tetsuya,Iio, Yukiko,Itoh, Kazuhiro,Mukaiyama, Osamu,Yamaguchi, Takeshi
, p. 1665 - 1668 (2007/10/03)
We report herein the synthesis and stereochemical structure-activity relationships of novel morpholine analogues 12 and 13 with regards to NK1, NK2 and NK3 tachykinin receptor binding affinity. An essential requirement for more potent binding affinities was controlled by absolute configuration. (S,R)-12 and (S,R)-13 exhibited high binding affinities for NK1, NK2 and NK3 receptors. (C) 2000 Elsevier Science Ltd. All rights reserved.
Heterocyclic compounds having tachykinin receptor antagonist activity their preparation and their use
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, (2008/06/13)
Compounds of the formula and quaternary ammonium ions thereof, wherein R1 and R2 are the same or different and are carbocyclic aryl or aromatic heterocyclic; A is methylene, carbonyl or sulfonyl; B is a single bond, C1-C4 alkylene or C2-C4, alkenylene; D is oxygen; E is C2 alkylene; G is C1-C4 alkylene or C2-C4 alkenylene; and L is -C(R4)(R5), wherein R4 and R5 together with the carbon atom to which they are attached represent a C5-C10 cycloalkyl or a C5-C10 heterocyclic. Especially preferred are compounds wherein L represents wherein J is a C1-C6 alkylene; Ar is a ring carbocyclic or aromatic heterocyclic and S*->O is a sulfoxide in which the sulfur atom is in the 5-configuration. The compounds have tachykinin receptor antagonist activity and exhibit an activity against both the NK1 and NK2 receptors.
A versatile method for the preparation of 2,2-disubstituted morpholine analogues
Takemoto, Toshiyasu,Iio, Yukiko,Nishi, Takahide
, p. 1785 - 1788 (2007/10/03)
We describe a versatile synthetic method for the preparation of 2,2- disubstituted morpholine analogues. Iodo-etherification of 1,1-disubstituted olefin with N-Boc-aminoethanol using NIS proceeded smoothly in a regioselective manner and the following cyclization was accomplished in good yield. We successfully applied this method for the preparation of the key intermediate 2 of tachykinin receptor antagonist. (C) 2000 Elsevier Science Ltd.
An efficient synthesis of enantiomerically pure 2-[(2R)-arylmorpholin- 2-yl]ethanols, key intermediates of tachykinin receptor antagonist
Nishi, Takahide,Ishibashi, Koki,Nakajima, Katsuyoshi,Iio, Yukiko,Fukazawa, Tetsuya
, p. 3251 - 3262 (2007/10/03)
We report herein an efficient and practical synthetic method for the preparation of enantiomerically pure 2[(2R)-arylmorpholin-2-yl]ethanols 1a- d, key intermediates of tachykinin receptor antagonist. Sharpless catalytic asymmetric dihydroxylation of 4a-d was employed to introduce the required absolute stereochemistry, and cyclization of 7a-d was accomplished by the Mitsunobu reaction.
