- A novel synthesis method of antioxidant 565
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The present invention proposes a novel synthesis method of antioxidant 565, the steps comprising: S1, the 2,6-di-tert-butylphenol dissolved in an organic solvent, add nitric acid dropwise, after the end of the reaction, the reaction liquid is steamed, petroleum ether washed, washed, vacuum dried to obtain 4-nitro-2,6-di-tert-butylphenol crystallization; S2, the dried 4-nitro-2,6-di-tert-butylphenol crystal dissolved in an organic solvent,N2 protection, and then added to the precious metal catalyst supported by a molecular sieve, filled with H 2,the reduction reaction was carried out to give 4-amino-2,6-di-tert-butylphenol; S3, the 4-amino-2,6-di-tert-butylphenol, melamine chloride, n-octylthiol and NaOH were added to the condensation tank, and the condensation reaction was carried out under the conditions ofN2 protection and 40-70 °C, and after the reaction, the reaction liquid was filtered and steamed to obtain the finished product. The present invention has the advantages of reaction safety, catalyst is not affected by halogens, product quality and high yield, is conducive to factory production.
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Paragraph 0026; 0029; 0032; 0035; 0038; 0041; 0044; ...
(2022/01/12)
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- SUBSTITUTED TRIAZINE COMPOUNDS AND USES THEREOF
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The present invention relates to compounds of formula (I) : including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of, for example, hypercholesterolemia.
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Page/Page column 25-26; 27; 36; 37
(2021/07/17)
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- Phenolic amine compound and preparation method and application thereof
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The invention relates to a phenolic amine compound as well as a preparation method and an application thereof. The phenolic amine compound has a structure as shown in a formula V, and not only has excellent oxidation resistance, but also has very good lubricating property.
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Paragraph 0099-0101; 0103; 0119-0121; 0123; 0139-0141; 0143
(2020/07/21)
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- Synthetic method of antioxidant 565
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The invention discloses a synthetic method of an antioxidant 565. The antioxidant 565 refers to 4-[4, 6-dioctyl-1, 3, 5-triazine-2-group] amino]-2, 6-di-tert-butylphenol; acid, 2, 6-di-tert-butylphenol and sodium nitrite are added into an organic solvent for nitrification reaction, and 2,6-ditert-butyl-4-nitrosophenol; sodium hydroxide and a reductant are added, and 2,6-ditert-butyl-4-nitrosophenol has a reduction reaction to generate 2,6-di-tert-butyl-4-aminophenol; n-octyl mercaptan reacts with cyanuric chloride under action of a catalyst to generate a 2,4-dioctyl thiol-6-chlorine-1,3,5-triazine compound; 2,6-ditert-butyl-4-nitrosophenol reacts with the 2,4-dioctyl thiol-6-chlorine-1,3,5-triazine compound to generate 4-[4, 6-dioctyl-1, 3, 5-triazine-2-amino]-2, 6-di-tert-butylphenol. Thesynthesis method avoids the use of an expensive hydrogenation catalyst and dangerous high pressure. The reaction condition is mild, operation is simple, the yield is high, the quality of intermediateproducts is good, and the yield and quality of the prepared 4-[4,6-dioctylthio-1,3,5-triazine-2-group] amino] 2,6-di-tert-butylphenol are higher.
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Paragraph 0046; 0051; 0052; 0055; 0060; 0061; 0064; 0069
(2019/04/29)
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- Discovery and SAR study of 3-(tert-butyl)-4-hydroxyphenyl benzoate and benzamide derivatives as novel farnesoid X receptor (FXR) antagonists
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3-(tert-Butyl)-4-hydroxyphenyl 2,4-dichlorobenzoate (1) was discovered in our in-house high throughput screening as a moderate FXR antagonist. To improve the potency and the stability of the hit 1, forty derivatives were synthesized and SAR was systematically explored. The results turn out that replacing the 2,4-dichlorophenyl with 2,6-dichloro-4-amidophenyl shows great improvement in potency, replacing the benzoate with benzamide shows improvement in stability and slight declining of potency and 3-(tert-butyl)-4-hydroxyphenyl unit is essential in obtaining the FXR antagonistic activity.
- Song, Kebiao,Xu, Xing,Liu, Peng,Chen, Lili,Shen, Xu,Liu, Junhua,Hu, Lihong
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p. 6427 - 6436
(2015/10/05)
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- Synthesis and crystal structure determination of 2,6-di-tert-butyl-4-(2,4, 6-triphenylpyridinium-1-yl)phenolate and its corresponding perchlorate salt
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2,6-Di-tert-butyl-4-(2,4,6-triphenylpyridinium-1-yl)phenolate belongs to the class of negatively solvatochromic dyes commonly used for the empirical determination of solvent polarities. By way of exception, it crystallizes without any solvent of crystallization due to the presence of two bulky tert-butyl groups in the phenolate moiety. The synthesis of this hydrophobic betaine dye has been improved and an X-ray crystal structure analysis of this solventless zwitterionic dye and its protonated form (as a perchlorate salt) has been carried out.
- Shekhovtsov, Sergey V.,Omelchenko, Irina V.,Dyakonenko, Viktoriya V.,Shishkin, Oleg V.,Allmann, Rudolf,Libor, Thomas,Reichardt, Christian,McHedlov-Petrossyan, Nikolay O.
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experimental part
p. 1394 - 1399
(2012/03/27)
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- DPPH radical scavenging activity of paracetamol analogues
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Biochemical studies suggest a direct relationship between the radical scavenging activity of paracetamol (I) and its antipyretic and analgesic action. To evaluate the effect of chemical modifications on the radical scavenging activity of compounds of type I, analogues 1-14 were prepared and submitted to a stable free radical (DPPH; 1,1-diphenyl-2-picryl-hydrazyl) assay. All paracetamol derivatives showed a significant higher efficiency than the parent compound. This study showed that radical scavenging activity can be increased by decreasing the phenolic ortho substituents steric hindrance or by introducing substituents on the acyl moiety like an indazole ring or the ionic N-methyl morpholinium group. A significant activating effect was also observed by replacing the 1,4-acylamidophenol with a 1,4-acylamidonaphthol system.
- Alisi, Maria Alessandra,Brufani, Mario,Cazzolla, Nicola,Ceccacci, Francesca,Dragone, Patrizia,Felici, Marco,Furlotti, Guido,Garofalo, Barbara,La Bella, Angela,Lanzalunga, Osvaldo,Leonelli, Francesca,Marini Bettolo, Rinaldo,Maugeri, Caterina,Migneco, Luisa Maria,Russo, Vincenzo
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p. 10180 - 10187
(2013/01/15)
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- TETRAHYDROISOQUINOLINE COMPOUND AND MEDICINAL USE THEREOF
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The present invention provide a tetrahydroisoquinoline compound having a superior ACAT-inhibitory activity and/or anti-oxidation action, particularly, novel compound represented by the formula (I) (wherein each symbol is as described in the specification) and a pharmaceutically acceptable salt thereof.
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Page/Page column 32
(2010/11/28)
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- Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
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The invention relates to new derivatives of 2-(iminomethyl)amino-phenyl which are NO synthase inhibitors and can trap reactive oxygen species. These compounds can notably be used for the treatment of stroke, of neurodegenerative diseases and of ischemic or hemorragic cardiac or cerebral infarctions. These compounds include: N-{4-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-{3-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-(4-{[{[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}(methyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-(3-{[(3,5-di-tert-butyl-4-hydroxybenzyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-[3-({[3-(4-hydroxy-3,5-diisopropylphenyl)propyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-(3-{[(4-hydroxy-3,5-diisopropylbenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(4-hydroxy-3,5-diisopropylphenyl)ethyl]amino}methyl)phenyl]thiophene-2-carboximidamide; N-2-(3,5-di-tert-butyl-4-hydroxybenzoyl)-N-1-(4-{[imino(thien-2-yl)methyl]amino}phenyl)-L-leucinamide; and pharmaceutically acceptable salts thereof.
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- Derivatives of 2-aminopyridines, their use as medicaments and pharmaceutical compositions containing them
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A compound of the formula wherein the substituents are defined as in the specification and their pharmaceutically acceptable salts having NOS and ROS activity.
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Page column 19
(2010/02/06)
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- Amidine derivatives, their preparation and application as medicines and pharmaceutical compositions containing same
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Amidine compounds of the formula wherein the substituents are defined as in the application useful as NO-synthase enzyme inhibitors.
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Page/Page column 45
(2008/06/13)
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- New derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
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The invention relates to new derivatives of 2-(iminomethyl)amino-phenyl which are NO synthase inhibitors and can trap reactive oxygen species. These compounds can notably be used for the treatment of stroke, of neurodegenerative diseases and of ischemic or hemorragic cardiac or cerebral infarctions. These compounds include: N-{4-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-{3-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-(4-{[{[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}(methyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-(3-{[(3,5-di-tert-butyl-4-hydroxybenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-[3-({[3-(4-hydroxy-3,5-diisopropylphenyl)propyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-(3-{[(4-hydroxy-3,5-diisopropylbenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(4-hydroxy-3,5-diisopropylphenyl)ethyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-2-(3,5-di-tert-butyl-4-hydroxybenzoyl)-N-1-(4-{[imino(thien-2-yl)methyl]amino}phenyl)-L-leucinamide; and pharmaceutically acceptable salts thereof.
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- Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
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A compound selected from the group consisting of a compound of the formula wherein A is selected from the group consisting of and the other substituents are defined in the specification having an inhibitory activity of NO-synthase enzymes producing nitrogen mono-oxide and/or an activity which traps the reactive oxygen species.
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Page column 72
(2008/06/13)
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- 2-(iminomethyl) amino-phenyl derivatives, preparation, application as medicines and pharmaceutical compositions containing same
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A compound of the formula wherein the substituents are defined as in the specification and their pharmaceutically acceptable salts having NOS and ROS activity.
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Page column 33
(2008/06/13)
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- NMR Study of Topomerization of N-Aroyl-p-Benzoquinonemonoimines
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The N-aroyl-p-benzoquinonemonoimines are studied by the 1H and 13C NMR spectroscopy.The barriers of degenerate Z,E-isomerization are measured.A considerable decrease in the barriers compared to other types of benzoquinone imines is due to interaction between the orbital of the unshared electron pair of nitrogen and ?* orbital of the C=O bond.Proceeding from the analysis of chemical shifts in the 13C NMR spectra and quantum-chemical calculations the lack of conjugation between the ?-electronic systems of p-benzoquinonimine and aryl fragments and the noncoplanar structure of the studied compounds are deduced.
- Pirozhenko, V. V.,Avdeenko, A. P.
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p. 1514 - 1519
(2007/10/03)
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- Phosphazene antioxidants
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Novel substituted phosphazene compounds are disclosed having the formula STR1 wherein w, x, y and z are integers the sum of which is from 3 to 6 with the proviso that w is at least 1 but equal to or less than (w+x+y+z)-1, x is from 1 to 5, y and z are from 0 to 2; R1 and R2 are the same or different and are C1 to C6 linear or branched alkyl; R3 is an unsubstituted or substituted aryl and n is 0 or an integer from 2 to 6; Q is --O--, STR2 --NR-- or --S--; Ar is STR3 R' and R are the same or different and are C1 to C6 linear or branched alkyl, with the proviso that R can also be hydrogen, wherein R1 and R2 are the same or different C1 to C4 linear or branched alkyl group and n is 0 or an integer from 2 to 6. These compounds display good solubilities in both organic and aqueous systems. Accordingly, they act as antioxidants in adhesive, sealant and coating compositions.
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- Solvent Bandwidth Dependence and Band Asymmetry Features of Charge-Transfer Transitions in N-Pyridinium Phenolates
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We have investigated the shape of the solvatochromic absorption band for "Betaine-26" 2,4,6-triphenyl-N-(di-tert-butyl-4-hydroxyphenyl)pyridinium ion in a range of polar, apolar, protic, and aprotic solvents.Multiphonon band theory, including both molecular modes and a vibrationally dispersive solvent, indicates that the solvents fall in three categories: (1) The bandshape for polar, aprotic solvents is well reproduced by that for a structureless continuous dielectric and a single high-frequency molecular mode.Solvent broadening correlates with εo-1 - εs-1, εo being the optical and εs the static dielectric constant.The molecular frequency, ωc, and displacement, Δc, are not very solvent dependent, emphasizing their molecular character, and the value ωc ca. 1600 cm-1 suggests that C-O, C-N, and C-C stretching is involved. (2) Bands for apolar, aprotic solvents correspond to the same model, ωc and Δc are again not very solvent dependent and coincide with the values for polar aprotic solvents.The solvent broadening is solvent independent, and wider than that for a structureless dielectric.This points to multipolar, dispersive, pressure, or pseudopotential forces as coupling mechanisms. (3) The bandshape for normal alcohols can only be reproduced by a model resting on two molecular modes and a vibrational high-frequency solvent "tail".Broadening, asymmetry, molecular frequencies, and deuterium isotope effects trace the protic solvent spectral entanglement to coupling between betaine-26 and a local mode group with features of both O-H stretching and bending and librational solvent motion.
- Kjaer, A. M.,Ulstrup, J.
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p. 1934 - 1942
(2007/10/02)
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