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Wednesday 11 February 2015

Ixazomib; MLN-9708.

CAS#:  1201902-80-8
Synonym:   Ixazomib; MLN-9708.
IUPAC/Chemical name: 
4-(carboxymethyl)-2-((R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutyl)-6-oxo-1,3,2-dioxaborinane-4-carboxylic acid
synthesis..........http://newdrugapprovals.org/2013/05/24/takeda-begins-phase-iii-trial-of-ixazomib-multiple-myeloma-drug/

Example 1: Synthesis of 4-(/?,S)-(carboxymethyl)-2-( (R)-I -(2-(2,5- dichlorobenzamido)acetamido)-3-methylbutyl)-6-oxo-l,3,2-dioxaborinane-4- carboxylic acid (1-1)
Figure imgf000062_0001


Form 1 as a crystalline solid (6.65 g, 88 %). 

1H NMR (500 MHz, DMSOd6, δ 110 0C): 
10.08 (s, IH), 8.69 (s, IH), 
7.61 (s, IH), 
7.52 (d, J = 1.3 Hz, 2H), 
4.26 (d, J = 5.5 Hz, 2H), 
2.70 (q, J = 14.5 Hz, 4H), 
2.70 (bs, IH), 
1.72 (sept, J – 6.5 Hz, IH), 
1.42 (ddd, J = 5.2 Hz, J = 8.6 Hz, J = 13.9 Hz, IH), 
1.28 (ddd, J = 5.3, J = 9.4 Hz, J = 14.3 Hz, IH), 
0.91 (dd, J = 3.3 Hz, J = 6.6 Hz, 6H). 

MS (m/z) in CH3CN: [M+Na] calculated for C20H23BCl2N2NaO9, 539.1; found, 539.1.




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DHAKA BANGLADESH

.
Steamers and ferries in Sadarghat Port
Kawran Bazar
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Dry fish sellers at the Karwan Dry Fish Market (Bazar), Dhaka, Bangladesh.

Friday 6 February 2015

The diastereomeric ratio (dr) of the allylation products is determined by 1H and19F NMR spectroscopy,

Figure



Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, Shanghai 200433, China
J. Chem. Educ., Article ASAP
DOI: 10.1021/ed500292q
Publication Date (Web): January 23, 2015
Copyright © 2015 The American Chemical Society and Division of Chemical Education, Inc.

Diastereoselective Allylation of N-tert-Butanesulfinyl Imines: An Asymmetric Synthesis Experiment for the Undergraduate Organic Laboratory

An asymmetric synthetic experiment that encompasses both diastereoselectivity and enantioselectivity is described. In this experiment, Zn-mediated allylation of an (R)-N-tert-butanesulfinyl imine is first performed to obtain either diastereomer using two different solvent systems, followed by oxidation of the homoallylic N-tert-butanesulfinyl amines, which gives either enantiomer of the corresponding products. Purification by flash column chromatography is required at the final step and the desired products are isolated in good overall yields. The diastereomeric ratio (dr) of the allylation products is determined by 1H and19F NMR spectroscopy, while the enantiomeric excess (ee) of the final products is measured by chiral HPLC. Overall, this experiment can be carried out with readily accessible reagents under mild conditions. Moreover, it enables students to learn the differences between enantiomers and diastereomers, the determination of ee and dr regarding optical compounds using HPLC and NMR spectroscopy, and how a reversal of stereochemical outcome is realized simply by tuning the reaction solvent.


Figure

NMR analyses of the homoallylic N-tert-butanesulfinyl amines obtained from the THF system (left) and the DMF system (right).



化学系

www.chemistry.fudan.edu.cn/











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Tuesday 3 February 2015

EDIVOXETINE

Edivoxetine structure.png
EDIVOXETINE, LY 2216684
(1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol
UNII-3W9N3F4JOO, 1194508-25-2, Edivoxetine [USAN], Edivoxetine (USAN/INN), Edivoxetine [USAN:INN], 3W9N3F4JOO
Molecular Formula:C18H26FNO4
Molecular Weight:339.401743 g/mol
Edivoxetine (INNLY-2216684) is a drug which acts as a selective norepinephrine reuptake inhibitor and is currently under development by Eli Lilly for attention-deficit hyperactivity disorder (ADHD) and as an antidepressant treatment.[1][2] It was in phase IIIclinical trials, in 2012, for major depressive disorder, but failed to get approval.[1][3]

Effectiveness

In a study published in 2010, edivoxetine failed to prove superiority over placebo, as measured by Hamilton Depression Rating Scale. However, effectiveness could be observed using the Self-Rated Quick Inventory of Depressive Symptomatology.[4]
In a study published in 2011, using the Montgomery-Åsberg Depression Rating Scale and the Sheehan Disability Scale, edivoxetine showed superiority over placebo, with higher response and remission rates.[5]
In December 2013, Eli Lilly announced that the clinical development of edivoxetine will be stopped due to lack of efficacy compared to SSRI alone in three separate clinical trials.[6]

Side effects

Side effects significantly associated with edivoxetine are headache, nausea, constipation, dry mouth and insomnia.[4]
The above mention studies report increases of the cardiac rhythm, and one also increases of diastolic and systolic blood pressures.[4][5]
Figure
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/op5003825
There is a growing trend in Ireland toward greater collaboration between academia and the pharmaceutical industry. This is an activity encouraged at a national policy level as a means of providing researchers from academic institutions the opportunity to gain important first-hand experience in a commercial research environment, while also providing industry access to expertise and resources to develop new and improved processes for timely medicines. The participating company benefits in terms of its growth, the evolution of its strategic research and development, and the creation of new knowledge that it can use to generate commercial advantage. The research institute benefits in terms of developing skill sets, intellectual property, and publications, in addition to access to identified current industry challenges. A case study is provided describing the collaborative partnership between a synthetic chemistry research team at University College Cork (UCC) and Eli Lilly and Company.
Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre,University College Cork, Cork, Ireland
E-mail: a.maguire@ucc.ie.

University College Cork

SYSTEMATIC (IUPAC) NAME
(1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(tetrahydro-2H-pyran-4-yl)ethanol
CLINICAL DATA
LEGAL STATUS
?
IDENTIFIERS
CAS NUMBER1194508-25-2
1194374-05-4 (hydrochloride)
ATC CODENone
PUBCHEMCID 11186829
CHEMSPIDER9361913
CHEMICAL DATA
FORMULAC18H26FNO4 
MOLECULAR MASS339.402 g/mol

References

  1.  Jun Yan (March 2012). “Pipeline for new antidepressants flowing slowly”Psychiatric News (American Psychiatric Association) 47 (5): 1b-29. Retrieved 2012-04-27.
  2.  “Statement on a nonproprietary name adopted by the USAN council – Edivoxetine”(Press release). American Medical Association. 2012. Retrieved 2012-04-12.
  3.  Chancellor D (November 2011). “The depression market”Nature Reviews. Drug Discovery 10 (11): 809–10. doi:10.1038/nrd3585PMID 22037032.
  4.  Dubé S, Dellva MA, Jones M, Kielbasa W, Padich R, Saha A, Rao P (April 2010). “A study of the effects of LY2216684, a selective norepinephrine reuptake inhibitor, in the treatment of major depression”Journal of Psychiatric Research 44 (6): 356–363.doi:10.1016/j.jpsychires.2009.09.013PMID 19909980.
  5.  Pangallo P, Dellva MA, D’Souza DN, Essink B, Russell J, Goldberger C (June 2011).“A randomized, double-blind study comparing LY2216684 and placebo in the treatment of major depressive disorder”Journal of Psychiatric Research 45 (6): 748–755. doi:10.1016/j.jpsychires.2011.03.014PMID 21511276.
  6.  https://investor.lilly.com/releasedetail.cfm?ReleaseID=811751
H-NMR spectral analysis
(1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol NMR spectra analysis, Chemical CAS NO. 1194508-25-2 NMR spectral analysis, (1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol H-NMR spectrum
CAS NO. 1194508-25-2, (1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol H-NMR spectral analysis
C-NMR spectral analysis
(1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol NMR spectra analysis, Chemical CAS NO. 1194508-25-2 NMR spectral analysis, (1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol C-NMR spectrum
CAS NO. 1194508-25-2, (1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol C-NMR spectral analysis