19291-02-2Relevant academic research and scientific papers
Asymmetric Transformation of (RS)-Cysteine via Formation of (RS)-4-Thiazolidinecarboxylic Acids
Shiraiwa, Tadashi,Kataoka, Kazuo,Sakata, Shinji,Kurokawa, Hidemoto
, p. 109 - 113 (1989)
Either (R)- or (S)-cysteine ((R)- or (S)-Cys) was efficiently obtained from (RS)-Cys by the asymmetric transformation via formation of (RS)-thiazolidinecarboxylic acid ((RS)-THC) or (RS)-2,2-dimethyl-4-thiazolidinecarboxylic acid ((RS)-DMZ) and by using (2R,3R)- or (2S,3S)-tartaric acid ((R)- or (S)-TA), as a resolving agent, in acetic acid.The asymmetric transformation was carried out by combination of crystallization of less soluble salt of (S)-THC or -DMT with (R)-TA (or salt of (R)-THC or -DMT with (S)-TA) and epimerization of soluble diastereomeric salt.The (R)- and (S)-THCs from the less soluble salts gave approximately optically pure (R)- and (S)-Cys's, respectively, in 64percent yield.The asymmetric transformation via formation of (RS)-DMT was more succeefully achieved by adding 0.1 molar equivalent of salicylaldehyde; that is, hydrolysis of the obtained less soluble salt gave optically pure (R)- and (S)-Cys's, respectively, in 80percent yield based on the (RS)-Cys used as the starting material.
Optical Resolution by Replacing Crystallization of (RS)-4-Thiazolidinecarboxylic Acid with L-Amino Acids as Cosolute
Shiraiwa, Tadashi,Yamauchi, Masahiro,Tatsumi, Takeshi,Kurokawa, Hidemoto
, p. 267 - 273 (1992)
The optical resolution by replacing crystallization of (RS)-4-thiazolidinecarboxylic acid was carried out with coexisting eight L-amino acids and the effect of the latter was examined.L-Isoleucine and L-cysteine as the cosolute led to preferential crystallization of (R)-THC from an aqueous solution of (RS)-THC, whereas the other L-amino acids gave (S)-THC.L-Cys, L-threonine, L-4-hydroxyproline , and L-serine as the cosolute seemed to give better selectivity for crystallization of one enantiomer than L-Ile, L-valine, L-proline, and L-alanine.The optical resolution with L-Hyp was successfully achieved and suggested a possibility of successive optical resolution to give both (R)- and (S)-THC.
Asymmetric Transformation of DL-4-Thiazolidinecarboxylic Acid
Shiraiwa, Tadashi,Kataoka, Kazuo,Kurokawa, Hidemoto
, p. 2041 - 2042 (1987)
A mixture of DL-4-thiazolidinecarboxylic acid (DL-THC), (+)- or (-)-tartaric acid ((+)- or (-)-TA), and salicylaldehyde in acetic acid was stirred at 80 deg C to give a salt composed of equimolar amounts of L-THC and (-)-TA or that of D-THC and (+)-TA.D- and L-THC with optical purity of 97-99percent were obtained from these salts in 68-78percent yield.
Optical Resolution by Preferential Crystallization of DL-Thiazolidine-4-carboxylic Acid
Shiraiwa, Tadashi,Sado, Yujin,Komure, Masamitsu,Kurokawa, Hidemoto
, p. 3277 - 3284 (1987)
Infrared spectrum, solubility, and ternary solubility diagram indicated that DL-thiazolidine-4-carboxylic acid (DL-THC) is a conglomerate at room temperature.The free energy of critical nucleation in supersaturated solutions for the crystallization of D- and L-THC was examined to resolve DL-THC efficiently by preferential crystallization.Successive preferential crystallization of DL-THC was experimented at 20 deg C for an aqueous racemic solution with a supersaturation of 150percent, and D- and L-THC with optical purity 96-100percent were obtained in the range of resolution of 58-76percent.The optical resolution was more succesfully done in 1 mol dm-3 aqueous glycine to give D- and L-THC with optical purity of 93-99percent in the degree of resolution of 77-87percent.Recrystallization of D- and L-THC obtained with a succeeding treatment with hydroxylamine hydrochloride gave D- and L-cysteine with 100percent optical purity.
PROCESS FOR PURIFYING (METH)ACRYLIC ACID
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Page/Page column 7-8, (2014/10/03)
A process for producing a grade of (meth)acrylic acid having residual formaldehyde levels of under 100 parts per million.
Synthesis and biological activity of novel L-amino acid based analgesic compounds
Pan, Junzhu,Wang, Qianqian,He, Gu,Ouyang, Liang,Guo, Li
scheme or table, p. 359 - 364 (2011/10/31)
Synthesis and analgesic activity studies of a series of L-amino acid based compounds were described. These compounds were designed as potential N-type Calcium Channel Blockers and their structures were confirmed by 1H NMR and ESI-MS spectra. Some of the compounds exhibited significant analgesic activity in Mouse Hot-Plate tests. According to the data of pharmacological experiments, we carried out preliminary structure-activity studies and the results indicated that this kind of compounds was useful for the development of new analgesic drugs.
EFFICIENT SYNTHESIS OF CHELATORS FOR NUCLEAR IMAGING AND RADIOTHERAPY: COMPOSITIONS AND APPLICATIONS
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Page/Page column 95-96, (2008/06/13)
Novel methods of synthesis of chelator-targeting ligand conjugates, compositions comprising such conjugates, and therapeutic and diagnostic applications of such conjugates are disclosed. The compositions include chelator-targeting ligand conjugates optionally chelated to one or more metal ions. Methods of synthesizing these compositions in high purity are also presented. Also disclosed are methods of imaging, treating and diagnosing disease in a subject using these novel compositions, such as methods of imaging a tumor within a subject and methods of diagnosing myocardial ischemia.
HETEROCYCLIC CARBOXYLIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITION FOR INHIBITING LIPID ACCUMULATION CONTAINING SAME
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Page/Page column 54, (2008/12/04)
The present invention relates to a novel heterocyclic carboxylic acid derivative, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same as an active ingredient for inhibiting the accumulation of lipids in the body.
NOVEL DIPEPTIDYL PEPTIDASE IV INHIBITORS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND PROCESS FOR THEIR PREPARATION
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Page/Page column 45, (2008/06/13)
The present invention relates to novel compounds useful as dipeptidyl peptidase IV (DPP-IV) inhibitors of the formula: (I) wherein Y is -S(O)m, -CH2-, CHF, or -CF2; m is 0, 1, or 2; X is a bond, C1-C5 alkyl (e.g., -CH2-), or -C(=0)-; the dotted line [----] in the carbocyclic ring represents an optional double bond; R1 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heterocyclylalkyl, substituted or unsubstituted heteroarylalkyl, CN, -COOR3, CONR3R4, -OR3, -NR3R4, or NR3COR3; R2 is hydrogen, cyano, COOH, or an isostere of a carboxylic acid (such as SO3H, CONOH, B(OH)2, PO3R3R4, SO2NR3R4, tetrazole, -COOR3, -CONR3R4, NR3COR4, or -COOCOR3).
NEW ADAMANTANE DERIVATIVES AS DIPEPTIDYL, PEPTIDASE IV INHIBITORS, PROCESSES FOR THEIR PREPARATION, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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Page/Page column 30, (2008/06/13)
The present invention relates to dipeptidyl peptidase IV (DPP-IV) inhibitors of the formula (A): wherein R1, R2, Y, and n are as defined herein, pharmaceutical compositions containing the same, processes for their preparation, and methods for treating disorders mediated by DPP-IV inhibition, such as diabetes, especially Type II diabetes, with them.
