- Modified Kagan's amide: Synthesis and application as a chiral solvating agent for hydrogen-bonding based chiral discrimination in NMR
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A modified Kagan's amide, N-((S)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl)-3,5-dinitrobenzamide [(S)-2] has been designed, synthesized and screened as a Chiral Solvating Agent (CSA) for discrimination of optically active substrates. The proposed mode of action for recognition of chiral isomers of analytes by CSA is based on hydrogen-bonding. The 1H NMR signals of the two isomers of chiral amides, sulfoxides, α-substituted acids, α-hydroxy ketone, epoxy ketone and N-protected amino acids with (S)-2 were well resolved for practical applications of determination of optical purity. The CSA was also screened for detection of separation of signals in 19F NMR. This journal is
- Jain, Nilesh,Patel, Ravi B.,Bedekar, Ashutosh V.
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- AGENT FOR INHIBITING EXPRESSION OF NPC1L1 AND/OR LIPG MRNA AND AGENT FOR PREVENTING AND/OR TREATING OBESITY
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Provided is an agent for treating and/or preventing obesity. An agent for suppressing expression of NPC1L1 (Niemann-Pick disease, type C1, gene-like 1) and/or LIPG (Lipase, endothelial) mRNA, and an agent for preventing and/or treating obesity, each comprising, as an active ingredient, a compound having CETP inhibitory activity, or a salt thereof, or a solvate thereof.
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Paragraph 0086-0090
(2014/10/16)
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- AGENT FOR INHIBITING EXPRESSION OF LIPID METABOLISM RELATED MRNA
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The present invention is intended to provide a pharmaceutical product for inhibiting expression of at least one lipid metabolism related mRNA selected from the group consisting of Angptl4 mRNA, SCD-1 mRNA, and SREBP1c mRNA, the present invention is also intended to provide a preventive and/or therapeutic agent for various diseases based on inhibition of expression of at least one lipid metabolism related mRNA selected from the group consisting of Angptl4 mRNA, SCD-1 mRNA, and SREBP1c mRNA, and the present invention relates to an agent for inhibiting expression of at least one lipid metabolism related mRNA selected from the group consisting of Angptl4 mRNA, SCD-1 mRNA, and SREBP1c mRNA, and relates also to a preventive and/or therapeutic agent for various diseases based on the inhibition of the expression of at least one lipid metabolism related mRNA selected from the group consisting of Angptl4 mRNA, SCD-1 mRNA, and SREBP1c mRNA, the agent comprising a compound represented by Formula (I), its salt, or a solvate of any of them as an active ingredient: wherein the symbols are the same as those given in the description..
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- Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: Applications toward the synthesis of calcimimetic agents
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Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst. Two convenient and facile approaches to the synthesis of new and known calcimimetic analogues employing enantiopure (1-naphthalen-1-yl)ethylamine as chiral precursor are described.
- Ou, Wenhua,Espinosa, Sandraliz,Meléndez, Héctor J.,Farré, Silvia M.,Alvarez, Jaime L.,Torres, Valerie,Martínez, Ileanne,Santiago, Kiara M.,Ortiz-Marciales, Margarita
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p. 5314 - 5327
(2013/07/25)
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- METHOD FOR PRODUCING OPTICALLY ACTIVE 1-BROMO-1-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]ETHANE
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A method for preparing optically active 1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane having a high optical purity, which comprises the step of brominating optically active 1-[3,5-bis(trifluoromethyl)phenyl]ethanol by using, as a brominating agent, (a) a combination of a phosphorus halide and hydrogen bromide, (b) a combination of 1,2-dibromo-1,1,2,2-tetrachloroethane and an organic phosphorous compound represented by the general formula (I): P(R1)(R2)(R3) (in the formula, R1, R2, and R3 independently represent a C6-10 aryl group, a C6-10 aryloxy group, a C1-10 alkyl group, a C1-10 alkoxyl group, a C3-6 cycloalkyl group, or a C3-6 cycloalkoxy group), or (c) a combination ofN-bromosuccinimide and a dialkyl sulfide.
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- OPTICALLY ACTIVE DIBENZYLAMINE DERIVATIVE, AND MANUFACTURING METHOD FOR SAME
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Substantially optically pure (S)-trans-{4-[({2-[({1-[3,5-bis(trifluoromethyl)phenyl]ethyl}{5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-yl}amino)methyl]-4-(trifluoromethyl)phenyl}(ethyl)amino)methyl]cyclohexyl}acetic acid, or a salt thereof, or a solvate thereof, which has actions of reducing amount of PCSK9 protein and increasing amount of LDL receptor.
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Paragraph 0116; 0117; 0118; 0119
(2013/04/23)
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- Indanyl-piperazine compounds
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A compound selected from those of formula (I): wherein: R3 represents a hydrogen atom, and R1 and R2 together with the carbon atoms carrying them form a benzene, naphthalene or quinoline ring structure, each of the ring structures being optionally substituted, ?or R1 represents a hydrogen atom, and R2 and R3 together with the carbon atoms carrying them form a benzene, naphthalene or quinoline ring structure, each of the ring structures being optionally substituted, n represents 1 or 2, —X— represents a group selected from —(CH2)m—O-Ak-, —(CH2)m—NR4-Ak-, —(CO)—NR4-Ak- and —(CH2)m—NR4-(CO)—, ?m represents an integer between 1 and 6 inclusive, Ak represents an optionally substituted alkylene chain, and R4 represents a hydrogen atom or an alkyl group, Ar represents an aryl or heteroaryl group, its enantiomers, diasteroisomers, and addition salts thereof with a pharmaceutically acceptable acid. Medical products containing the same which are useful in the treatment of conditions requiring a serotonin reuptake inhibitor and/or NK1 antagonist.
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Page/Page column 21-22
(2010/11/24)
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- Process for producing optically active 1-(fluoro- or trifluoromethyl-substituted phenyl) ethylamine and process for purifying same
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An optically active 1-(fluoro- or trifluoromethyl-substituted phenyl)ethylamine is produced with high optical purity and in an industrially simple and efficient manner by asymmetrically reducing an optically active imine, obtained by dehydration and conde
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Page column 33-34
(2008/06/13)
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- Thiourea inhibitors of herpes viruses. Part 2: N-Benzyl-N′- arylthiourea inhibitors of CMV
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A series of highly potent thiourea inhibitors of cytomegalovirus (CMV) with improved stability properties was prepared and evaluated. Compound 29 inhibited the virus in cultured HFF cells with IC50 of 0.2nM.
- Bloom, Jonathan D.,Dushin, Russell G.,Curran, Kevin J.,Donahue, Fran,Norton, Emily B.,Terefenko, Eugene,Jones, Thomas R.,Ross, Adma A.,Feld, Boris,Lang, Stanley A.,DiGrandi, Martin J.
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p. 3401 - 3406
(2007/10/03)
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- Highly regioselective hydrogenolysis of bis(α-methylbenzyl)amine derivatives affected by the trifluoromethyl substituent on the aromatic ring
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(Matrix presented) The highly regioselective hydrogenolysis of bis(α-methylbenzyl)amine derivatives proceeded with influence not from the electronic effect but from the steric effect of the trifluoromethyl substituent on the aromatic ring to provide a practical asymmetric synthesis of trifluoromethyl-substituted α-phenylethylamines.
- Kanai, Masatomi,Yasumoto, Manabu,Kuriyama, Yokusu,Inomiya, Kenjin,Katsuhara, Yutaka,Higashiyama, Kimio,Ishii, Akihiro
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p. 1007 - 1010
(2007/10/03)
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- Optically active amines. 34.1 Application of the benzene chirality rule to ring-substituted phenylcarbinamines and carbinols
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The negative sign of the 1Lb, Cotton effects (CEs) from about 250 to 270 nm in the circular dichroism (CD) spectra of (R)-α-phenylethylamine and (R)-α-phenylethyl alcohol and other phenylalkylcarbinamines and carbinols is determined by vibronic borrowing from allowed transitions at shorter wavelength. On ring substitution, bond transition moments are induced in the benzene ring bonds adjacent to the attachment bond of the chiral group, resulting in enhanced coupling of the 1Lb transition with the chiral group. A sign reversal for the 1Lb, CEs on para substitution with an atom or group with a positive spectroscopic moment (C1, CH3) can be viewed as the overshadowing of the vibronic contribution by an induced contribution of opposite sign On para substitution with a group with a negative spectroscopic moment (CF3, CN), the sign of the 1Lb CEs is unchanged since the vibronic and induced contributions have the same sign. Meta substitution by an atom or group will result in bond moments in an opposite sense from that caused by the same atom or group in the para position. Thus on meta substitution by a group with a positive spectroscopic moment (C1, CH3), both the vibronic and induced contributions have the same sign, and the sign of the 1Lb CEs is the same as that of the unsubstituted parent. For meta substitution by a group with a negative spectroscopic moment (CF3, CN), the sign of the induced contribution is opposite to that of the vibronic contribution. In the case of CF3 and CN groups, the latter is more important than the former, and the sign of the 1Lb CEs is the same as that of the unsubstituted parent. Ortho substitution again reverses the sense of the induced bond transition moments from that induced by the same meta substituents. Thus, provided the position of the substituent and its spectroscopic moment are taken into account the absolute configuration of substituted phenylmethylcarbinamines and carbinols can often be assigned.
- Pickard, Simeon T.,Smith, Howard E.
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p. 5741 - 5747
(2007/10/02)
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