- Asymmetric Hydrogenation of β-Secondary Amino Ketones Catalyzed by a Ruthenocenyl Phosphino-oxazoline-ruthenium Complex (RuPHOX-Ru): The Synthesis of γ-Secondary Amino Alcohols
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A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX-Ru) was applied successfully to the asymmetric hydrogenation of β-secondary amino ketones, directly affording the corresponding chiral γ-secondary amino alcohols in up to 99% yield and with 99% ee. Reaction with β-(benzylamino)-1-phenylpropan-1-one could be performed on a gram-scale with a relatively low catalyst loading (up to 2000 S/C). The resulting hydrogenated product could be used for the synthesis of synthetically useful compounds.
- Wang, Jianxia,Wang, Yanzhao,Liu, Delong,Zhang, Wanbin
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p. 3262 - 3272
(2015/11/03)
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- SUBSTITUTED 3-PHENYLPROPYLAMINE DERIVATIVES FOR THE TREATMENT OF OPHTHALMIC DISEASES AND DISORDERS
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The present invention relates generally to compositions and methods for treating neurodegenerative diseases and disorders, particularly ophthalmic diseases and disorders. Provided herein are substituted 3-phenylpropylamine derivative compounds and pharmaceutical compositions comprising said compounds. The subject compositions are useful for treating and preventing ophthalmic diseases and disorders, including age-related macular degeneration (AMD) and Stargardt's Disease.
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Paragraph 0423; 0425; 0413
(2014/09/29)
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- Synthesis and catalytic properties of 4-aryl-2,3-dihydro-4 H -pyrimido[2,3- b ]benzothiazoles for asymmetric acyl or carboxyl group transfer reactions
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4-Aryl-2,3-dihydro-4H-pyrimido[2,3-b]benzothiazoles (4-Ar-DHPBs) were synthesized and their catalytic activity and selectivity in kinetic resolution of a secondary alcohol as well as in the Steglich rearrangement and related reactions were evaluated. 4-Aryl-DHPBs showed low enantioselectivity in the acylative kinetic resolution of 1-phenylethanol. Conversely, they catalyzed the Steglich rearrangement with moderate to excellent enantioselectivity, demonstrating the possibility for remote stereocontrol by introduction of a substituent at the 4-position of DHPB.
- Viswambharan, Baby,Okimura, Tatsuya,Suzuki, Satoko,Okamoto, Sentaro
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experimental part
p. 6678 - 6685
(2011/10/09)
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- TREATMENT OF METABOLIC SYNDROME WITH NOVEL AMIDES
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The present invention relates to the treatment of metabolic syndrome or disorders associated with metabolic syndrome comprising administering a compound of the invention.
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Page/Page column 83-84
(2009/07/17)
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- ALKYNYL PHENYL DERIVATIVE COMPOUNDS FOR TREATING OPHTHALMIC DISEASES AND DISORDERS
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Provided are alkynyl phenyl derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.
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Page/Page column 177-178
(2009/03/07)
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- Lewis acid-mediated highly regioselective SN2-type ring-opening of 2-Aryl-N-tosylazetidines and aziridines by alcohols
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(Chemical Equation Presented) Lewis acid-mediated highly regioselective SN2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols to afford various 1,3-amino ethers in excellent yields with good enantiomeric excess is described. Similar S
- Ghorai, Manas K.,Das, Kalpataru,Shukla, Dipti
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p. 5859 - 5862
(2008/02/09)
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- Novel phosphorus-containing prodrug
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Novel cyclic phosphoramidate prodrugs of parent drugs MH of formula I their use in delivery of drugs to the liver, their use in enhancing oral bioavailability, and their method of preparation are described.
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Page/Page column 63
(2010/11/08)
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- Polymer-supported chiral sulfonamide catalyzed one-pot reduction of β-keto nitriles: A practical synthesis of (R)-fluoxetine and (R)-duloxetine
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Enantioselective reduction of β-keto nitriles to optically active 1,3-amino alcohols has been carried out in one step using an excess of borane-dimethyl sulfide complex as a reductant and a polymer-supported chiral sulfonamide as a catalyst with moderate to high enantioselectivity. The facile and enantioselective method to prepare optically active 1,3-amino alcohols to be converted into 3-aryloxy-3-arylpropylamine-type antidepressant drugs (R)-fluoxetine, and (R)-duloxetine is also reported.
- Wang, Guangyin,Liu, Xingshun,Zhao, Gang
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p. 1873 - 1879
(2007/10/03)
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- Efficient Heterogeneous Asymmetric Transfer Hydrogenation of Ketones Using Highly Recyclable and Accessible Silica-Immobilized Ru-TsDPEN Catalysts
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(Matrix presented) Chiral Ru-TsDPEN [N-(p-toluenesulfonyl)-1,2- diphenylethylenediamine]-derived catalysts were first successfully immobilized onto amorphous silica gel and mesoporous silicas of MCM-41 and SBA-15 by an easily accessible approach. The catalyst immobilized on silica gel demonstrated remarkably high catalytic activities and excellent enantioselectivities (up to >99% ee) for the heterogeneous asymmetric transfer hydrogenation of various ketones. Particularly, the catalyst could be readily recovered and reused in multiple consecutive catalytic runs (up to 10 uses) with the completely maintained enantioselectivity.
- Liu, Pei Nian,Gu, Pei Ming,Wang, Fei,Tu, Yong Qiang
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p. 169 - 172
(2007/10/03)
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- Asymmetric dihydroxylation route to (R)-isoprenaline, (R)-norfluoxetine and (R)-fluoxetine
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An efficient asymmetric synthesis of enantiomerically pure (R)-isoprenaline, (R)-norfluoxetine and (R)-fluoxetine is described using Sharpless asymmetric dihydroxylation as the key step.
- Kumar, Pradeep,Upadhyay, Rajesh Kumar,Pandey, Rajesh Kumar
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p. 3955 - 3959
(2007/10/03)
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- Process for the preparation of enantiomerically pure 3-phenyl-3-hydroxypropylamine
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The present invention relates to an improved process for the synthesis of enantiomerically pure 3-phenyl-3-hydroxypropylamine of formula I; more particularly the present invention relates to the said process using styrene; the synthetic strategy features a Sharpless asymmetric dihydroxylation (SAD) route to the target compound, using styrene, a readily accessible starting material gives the optically pure dihydroxy compound (ee >97%; the selective monotosylation of primary alcohol, nucleophilic displacement by cyano and subsequent reduction to amino group furnishes the desired 3-phenyl-3-hydroxypropylamine in enatiomerically pure form, a key intermediate in the synthesis of variety of oxetine related anti-depressant drugs.
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- Prodrugs for liver specific drug delivery
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The present invention is directed towards novel cyclic phosph(oramid)ate prodrugs of alcohol, amine-, and thiol-containing drugs, their preparation, their synthetic intermediates, and their uses. Another aspect of the invention is the use of the prodrugs
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- [3H]-(R)-NPTS, a radioligand for the type 1 glycine transporter.
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The synthesis of NPTS, 6, a potent inhibitor of the type 1 glycine transporter (GlyT1) is described, as well as preparation of 6 in optically active and tritiated form for use as a radioligand for affinity displacement assay of GlyT1.
- Lowe 3rd., John A,Drozda, Susan E,Fisher, Katherine,Strick, Christine,Lebel, Lorraine,Schmidt, Christopher,Hiller, Donna,Zandi, Kathleen S
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p. 1291 - 1292
(2007/10/03)
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- Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: Lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles
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A facile preparation of (±)-3-hydroxy-3-phenylpropanenitrile has been carried out by ring-opening of styrene oxide with NaCN in aqueous ethanol. Subsequent kinetic resolution of this material via lipase-mediated transesterification gave the S-alcohol and R-acetate in excellent yields and high enantioselectivities, particularly with lipase PS-C 'Amano' II. The effect of solvents and immobilization of the lipase has also been investigated. It is interesting to note that the use of immobilized lipase for this transesterification process in hydrophobic solvents (diisopropyl ether, toluene and hexane) enhanced the reaction rate drastically and gave optimal yields with high enantioselectivity (>99%). Moreover, enantiopure 3-hydroxy-3-phenylpropanenitrile products have been converted via enantioconvergent routes into the (R)- and (S)-enantiomers of the important anti-depressants fluoxetine, tomoxetine, nisoxetine and norfluoxetine.
- Kamal, Ahmed,Khanna,Ramu
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p. 2039 - 2051
(2007/10/03)
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- An asymmetric dihydroxylation route to enantiomerically pure norfluoxetine and fluoxetine
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An efficient, practical asymmetric synthesis of (R)-norfluoxetine 1 and (R)-fluoxetine 2 has been achieved. The synthetic strategy features a Sharpless asymmetric dihydroxylation (SAD) route to the common building block 1,3-amino alcohol 9, from which (R)-norfluoxetine, (R)-fluoxetine and other related analogs can be synthesized.
- Pandey, Rajesh Kumar,Fernandes, Rodney A.,Kumar, Pradeep
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p. 4425 - 4426
(2007/10/03)
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- A practical asymmetric synthesis of (R)-fluoxetine and its major metabolite (R)-norfluoxetine
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A convenient and chromatography-free synthesis for the enantiomers of fluoxetine and norfluoxetine is described. The synthesis relied on the use of the CBS reduction, and Hofman rearrangement to establish the key common intermediate 5, and enrichment of optical purity of the final product by crystallization as the tartrate salt.
- Hilborn, James W.,Lu, Zhi-Hui,Jurgens, Alex R.,Fang,Byers, Paul,Wald, Stephen A.,Senanayake, Chris H.
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p. 8919 - 8921
(2007/10/03)
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- A convenient method for preparing enantiomerically pure norfluoxetine, fluoxetine and tomoxetine
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A convenient synthesis for enantiomers of norfluoxetine, fluoxetine and tomoxetine is described. All final products were derived from a common intermediate, 3-phenyl-3-hydroxypropylamine.
- Koenig, Thomas M.,Mitchell, David
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p. 1339 - 1342
(2007/10/02)
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- (R)-NORFLUOXETINE IN METHOD FOR OCCUPYING SEROTONIN 1C RECEPTORS
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The present invention provides (R)-norfluoxetine and pharmaceutically acceptable salts thereof capable of selectively occupying 5HT 1c receptors.
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