Big Chemical Encyclopedia

Chemical substances, components, reactions, process design ...

Articles Figures Tables About

Pharmaceutical products chirality

A study was conducted to measure the concentration of D-fenfluramine HCl (desired product) and L-fenfluramine HCl (enantiomeric impurity) in the final pharmaceutical product, in the possible presence of its isomeric variants (57). Sensitivity, stabiUty, and specificity were enhanced by derivatizing the analyte with 3,5-dinitrophenylisocyanate using a Pirkle chiral recognition approach. Analysis of the caUbration curve data and quaUty assurance samples showed an overall assay precision of 1.78 and 2.52%, for D-fenfluramine HCl and L-fenfluramine, with an overall intra-assay precision of 4.75 and 3.67%, respectively. The minimum quantitation limit was 50 ng/mL, having a minimum signal-to-noise ratio of 10, with relative standard deviations of 2.39 and 3.62% for D-fenfluramine and L-fenfluramine. [Pg.245]

Following these announcements, the first wave of publications addressing the use of SMB for the manufacture of pharmaceutical products of interest was published. The separation of a chiral hetrazepine [26], WEB 2170 6-(2-chlorophenyl)-8-9-di-hydro-l-methyl-8-[(morpholinyl)-carbonyl]-4H,7H-cyclopenta[4,5]-thieno[3,2-f][l,2,4]triazolo[4,3-a][l,4]diazepine. WEB 2170 is a chiral hetrazepine from Boehringer-Ingelheim. The enantioseparation of WEB 2170 was performed using cellulose triacetate (CTA) from Merck (Darmstadt) as the CSP and with pure methanol as eluent. [Pg.268]

Enantiometrically pure alcohols are important and valuable intermediates in the synthesis of pharmaceuticals and other fine chemicals. A variety of synthetic methods have been developed to obtain optically pure alcohols. Among these methods, a straightforward approach is the reduction of prochiral ketones to chiral alcohols. In this context, varieties of chiral metal complexes have been developed as catalysts in asymmetric ketone reductions [ 1-3]. However, in many cases, difficulties remain in the process operation, and in obtaining sufficient enantiomeric purity and productivity [2,3]. In addition, residual metal in the products originating from the metal catalyst presents another challenge because of the ever more stringent regulatory restrictions on the level of metals allowed in pharmaceutical products [4]. An alternative to the chemical asymmetric reduction processes is biocatalytic transformation, which offers... [Pg.136]

Nuclear magnetic resonance (NMR) spectroscopy in pharmaceutical research has been used primarily in a classical, organic chemistry framework. Typical studies have included (1) the structure elucidation of compounds [1,2], (2) investigating chirality of drug substances [3,4], (3) the determination of cellular metabolism [5,6], and (4) protein studies [7-9], to name but a few. From the development perspective, NMR is traditionally used again for structure elucidation, but also for analytical applications [10]. In each case, solution-phase NMR has been utilized. It seems ironic that although —90% of the pharmaceutical products on the market exist in the solid form, solid state NMR is in its infancy as applied to pharmaceutical problem solving and methods development. [Pg.94]

Enantioselective organic synthesis using modified skeletal catalysts has wide application in areas such as pharmaceutical production for example, synthesis of chiral alcohols from ketones [90], which is described in detail elsewhere in this book. [Pg.153]

Chiral sulfoxides have emerged as versatile building blocks and chiral auxiliaries in the asymmetric synthesis of pharmaceutical products. The asymmetric oxidation of prochiral sulfides with chiral metal complexes has become one of the most effective routes to obtain these chiral sulfoxides.We have recently developed a new heterogeneous catalytic system (WO3-30% H2O2) which efficiently catalyzes both the asymmetric oxidation of a variety of thioethers (1) and the kinetic resolution of racemic sulfoxides (3), when used in the presence of cinchona alkaloids such as hydroquinidine 2,5-diphenyl-4,6-pyrimidinediyl diether [(DHQD)2-PYR], Optically active sulfoxides (2) are produced in high yields and with good enantioselectivities (Figure 9.3). ... [Pg.288]

Many pharmaceutical products are chiral molecules, either as single isomers or more commonly as racemic mixtures. In addition, many formulated products are mixtures of active compounds together with a number of additives such as excipients. For chiral molecules, the pressure to develop single isomer forms as... [Pg.62]

L-Aspartic acid (12) is an industrially important, large volume, chiral compound. The primary use of aspartic acid in the fine chemical arena is in the production of aspartame, a high potency sweetener (Chapter 31). Other uses of L-aspartate include dietary supplements, pharmaceuticals, production of alanine (by decarboxylation), antibacterial agents, and lubricating compounds. There have been a number of reviews on L-aspartate production.53 56... [Pg.24]

Besides the production of (R)-l-phenylethanol as a fragrance,198 various pharmaceutically important chiral compounds have been produced at various lab scales by asymmetric hydrogenation with JST catalysts. These compounds include a P1-receptor antagonist denopamine hydrochloride (149),191 antidepressant fluoxetine hydrochloride (150),191 antipsychotic BMS 181100 (151),191 serotonin and norepinephrine inhibitor duloxetine (129),164 antihistaminic and anticholinergic orphenadrine (152),192 and antihistaminic neobenodine (153).192... [Pg.227]

The production of single enantiomers of drug intermediates is increasingly important in the pharmaceutical industry. Biocatalysis provides organic chemists an alternate opportunity to prepare pharmaceutically important chiral compounds. The advantages of biocatalysis over chemical catalysis are that enzyme-catalyzed reactions are stereoselective and regioselective, and can be carried out at ambient temperature and atmospheric pressure providing an environmentally friendly system. The selective examples presented in this... [Pg.343]

The development of a novel production system for D-pantoyl lactone (which is a lactone compound carrying a chiral hydroxy group and a chiral intermediate for the commercial production of D-pantothenate) by microbial asymmetric reduction has been undertaken. D-pantothenate is mainly used in various pharmaceutical products and as an animal feed additive, the current world production of calcium pantothenate being about 6,000 tons per year. Conventional commercial production of D-pantoyl lactone has depended exclusively on chemical synthesis involving optical resolution of a chemically synthesized racemic pantoyl lactone, which is the most troublesome step of the pantothenate synthesis process. [Pg.357]

Another example of how catalysis plays a key role in enabling our lives is in the synthesis of pharmaceuticals. Knowles s development, at Monsanto in the early 1970s, of the enantioselective hydrogenation of the enamide precursor to L-DOPA (used to treat Parkinson s disease), using a Rh-chiral phosphine catalyst (Section 3.5), led to a share in the Nobel prize. His colaureates, Noyori and Sharpless, have done much to inspire new methods in chiral synthesis based on metal catalysis. Indeed, the dramatic rise in the demand for chiral pharmaceutical products also fuelled an intense interest in alternative methodologies, which led to a new one-pot, enzymatic route to L-DOPA, using a tyrosine phenol lyase, that has been commercialized by Ajinomoto. [Pg.3]

K. Barry Sharpless (bom 1941) received his PhD in 1968 at Stanford University. Since 1990 he is W. M. Keck Professor of Chemistry at the Scripps Research Institute in La Jolla, USA. Among several other important discoveries. Sharpless developed catalysts for asymmetric oxidations. In 1980 he achieved the catalytic asymmetirc oxidation of allylic alcohols to chiral epoxides by utilizing titanium complexes with chiral ligands (e. g. Section 3.3.2). One of the many applications of chiral epoxides is the use of the epoxide (R)-glycidol for pharmaceutical production of beta-blockers. Sharpless received the Nobel prize for chemistry in 2001 together with Knowles and Noyori. [Pg.25]

More than 90% of biomolecules exhibit chirality. Many pharmaceutical products contain different chiral forms of drugs, some of which are harmful or ineffective. For example, one form of the drug naproxen has 28 times the anti-inflammatory activity of its enantiomer. In the synthetic form of dopamine used to treat Parkinson s disease one isomer acts on the nerve cells to control the patient s tremors whilst the other enantiomer is toxic. [Pg.8]

Abstract In this paper we address two aspects of ionic liquids (ILs) that to date have either no or limited studies. They are (1) exploitation of unique features of ILs to develop novel spectroscopic methods which otherwise is not possible and (2) development of novel spectroscopic methods for the sensitive and accurate determination of thermal physical properties of ILs. In the first category, we have successfully developed a novel, highly sensitive and accurate method for the determination of enantiomeric compositions of chiral compounds with different sizes, shape and functional groups including pharmaceutical products. This method is based on the use of a chiral IL which serves both as a solvent and also as a chiral selector. We have also demonstrated that ILs can be used to substantially enhance the sensitivity of thermal lens measurements. In the second category, we have demonstrated that transient grating technique and thermal lens technique can be used for the sensitive, accurate, nondestructive determination of thermal physical properties of ILs. [Pg.79]

CHIRAL IONIC LIQUID THAT FUNCTIONS AS BOTH SOLVENT AND CHIRAL SELECTOR FOR THE DETERMINATION OF ENANTIOMERIC COMPOSITIONS OF PHARMACEUTICAL PRODUCTS... [Pg.80]


See other pages where Pharmaceutical products chirality is mentioned: [Pg.106]    [Pg.257]    [Pg.290]    [Pg.115]    [Pg.249]    [Pg.122]    [Pg.425]    [Pg.567]    [Pg.518]    [Pg.283]    [Pg.47]    [Pg.59]    [Pg.511]    [Pg.113]    [Pg.667]    [Pg.113]    [Pg.1]    [Pg.2]    [Pg.166]    [Pg.7]    [Pg.34]    [Pg.227]    [Pg.4]    [Pg.38]    [Pg.81]    [Pg.88]    [Pg.102]    [Pg.9]    [Pg.194]    [Pg.586]    [Pg.688]    [Pg.194]   
See also in sourсe #XX -- [ Pg.255 ]




SEARCH



Chiral product

Chirality pharmaceuticals

Pharmaceutical production

Pharmaceutical productivity

Pharmaceutical products

© 2024 chempedia.info