91004-48-7Relevant academic research and scientific papers
Aminobenzoic acid derivative and preparation method and application thereof
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Paragraph 0105-0106, (2020/12/30)
The invention relates to an aminobenzoic acid derivative and a preparation method and application thereof, and belongs to the field of medicinal chemistry, and the structural formula of the aminobenzoic acid derivative is shown in the specification, R is alkyl, substituted phenyl, heteroaromatic ring group or substituted styryl; R is alkyl; R is alkyl, substituted phenyl or benzyl; R is alkyl; R is guanidyl; and R is alkyl. The preparation method is simple and high in yield. Most compounds of the invention have good influenza virus neuraminidase inhibition activity.
Preparation method of 3-hydroxy-4-methoxy-2-nitrobenzoic acid
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Paragraph 0064-0068, (2020/07/12)
The invention discloses a preparation method of 3-hydroxy-4-methoxy-2-nitrobenzoic acid, and belongs to the field of synthesis of medical intermediates. The preparation method comprises the followingsteps: starting from 3-alkoxy-4-acetoxybenzaldehyde (1), carrying out a nitration reaction process to obtain an intermediate (2), removing acetyl from the intermediate (2) to obtain an intermediate (3), methylating to obtain an intermediate (4), oxidizing the intermediate (4) to obtain an intermediate (5), deprotecting the intermediate (5), and recrystallizing to remove the isomer, thereby obtaining the 3-hydroxy-4-methoxy-2-nitrobenzoic acid (6). The method is simple, convenient and stable to operate, high in yield, environment-friendly, low in production cost and suitable for industrial large-scale production, and products in all steps are easy to separate.
DERIVATIVES OF PHENYLMETHANONE AS FTO INHIBITORS
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Paragraph 0088; 0089, (2019/07/17)
Disclosed herein is a phenyl methanone derivative as an FTO inhibitor. Also disclosed herein is a pharmaceutical composition comprising the same, and a method for reducing food intake or appetite, inhibiting weight gain, promote weight loss, reducing bloo
PROCESS FOR THE PREPARATION OF OPICAPONE AND INTERMEDIATES THEREOF
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Page/Page column 17, (2019/07/13)
The present invention i s relates to a process for the preparation of opicapone and a process to prepare intermediates to be used therein.
Discovery of a long-acting, peripherally selective inhibitor of catechol- O -methyltransferase
Kiss, László E.,Ferreira, Humberto S.,Torr?o, Leonel,Bonifácio, Maria Jo?o,Palma, P. Nuno,Soares-Da-Silva, Patrício,Learmonth, David A.
experimental part, p. 3396 - 3411 (2010/09/05)
Novel nitrocatechol-substituted heterocycles were designed and evaluated for their ability to inhibit catechol-O-methyltransferase (COMT). Replacement of the pyrazole core of the initial hit 4 with a 1,2,4-oxadiazole ring resulted in a series of compounds endowed with longer duration of COMT inhibition. Incorporation of a pyridine N-oxide residue at position 3 of the 1,2,4-oxadiazole ring led to analogue 37f, which was found to possess activity comparable to entacapone and lower toxicity in comparison to tolcapone. Lead structure 37f was systematically modified in order to improve selectivity and duration of COMT inhibition as well as to minimize toxicity. Oxadiazole 37d (2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4, 6-dimethylpyridine 1-oxide (BIA 9-1067)) was identified as a long-acting, purely peripheral inhibitor, which is currently under clinical evaluation as an adjunct to l-Dopa therapy of Parkinson's disease.
Process for the preparation of entacapone and intermediates thereof
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Page/Page column 7; 8, (2008/12/08)
New preparation process for the preparation of entacapone which comprises converting the 3,4-dimethoxy-5-nitrobenzoic acid into an activated derivative which is reacted with 2-cyano-N,N-diethylacetamide in the presence of a base to give 2-cyano-3-(3,4-dimethoxy-5-nitrophenyl)-N,N-diethyl-3-hydroxyacrylamide; reacting the resulting compound with MHB(OCOR)3 where R is (C1-C4)-alkyl, phenyl, or CF3; and M is a sodium, potassium or ((C1-C4)-alkyl)4N, in the presence of an appropriate solvent to give E-2-cyano-3-3,4-dimethoxy-5-nitrophenyl)-N,N-diethylacrylamide; and finally submitting the compound obtained to a demethylation reaction to yield entacapone. Both 2-cyano-3-(3,4-dimethoxy-5-nitrophenyl)-N,N-diethyl-3-hydroxyacrylamide and E-2-cyano-3-3,4-dimethoxy-5-nitrophenyl)-N,N-diethylacrylamide are new. Entacapone has industrial applicability as antiparkinson's agent.
Synthesis and evaluation of bifunctional nitrocatechol inhibitors of pig liver catechol-O-methyltransferase
Bailey, Karl,Tan, Eng Wui
, p. 5740 - 5749 (2007/10/03)
Bifunctional compounds were tested in vitro as potential inhibitors of pig liver catechol-O-methyltransferase (COMT) with respect to the catechol substrate 4-[(3,4-dihydroxyphenyl)azo]benzenesulfonate. The bifunctional compounds were a composite of either two nitrocatechols or one nitrocatechol and one phenol, linked by amide bonds to a spacer unit comprising two to five methylene groups. The unsymmetrical compounds N-[2-(4-hydroxybenzoylamine)ethyl]-3,4-dihydroxy-5- nitrobenzamide], N-[3-(4-hydroxybenzoyl-amine)propyl]-3,4-dihydroxy-5- nitrobenzamide] and N-[5-(4-hydroxybenzoylamine)pentyl]-3,4-dihydroxy-5- nitrobenzamide] demonstrated strong inhibitory action against COMT with K i values in the 100 nM range. In comparison, the monofunctional nitrocatechol analogues of these compounds had Ki values that were significantly higher.
