- Quinoxalines useful as cytoprotective agents
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Provided herein are compounds of Formula I, pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of a neurological disease, neurodegenerative disorder, or diabetes.
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Page/Page column 34
(2020/08/16)
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- Synthetic method of quinoxaline-5-sulfonyl chloride
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The invention discloses a synthetic method of quinoxaline-5-sulfonyl chloride. The synthetic method is characterized by comprising the following steps that S1, a condensation reaction is carried out on 1,2-diamino-3-nitrobenzene with glyoxal for obtaining 5-nitroquinoxaline; S2, the 5-nitroquinoxaline reacts with a reducing agent for generating 5-aminoquinoxaline; and S3, diazotization reaction and Sandermeyer reaction are carried out on the 5-aminoquinoxaline for obtaining the quinoxaline-5-sulfonyl chloride. According to the process, a novel Sandermeyer reaction strategy is adopted for introducing sulfonyl chloride groups, the yield is greater than 70%, and the characteristics of novel process route, relatively mild reaction conditions and the like are achieved.
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Paragraph 0019; 0020; 0021
(2018/05/01)
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- Preparation method of benzopyridazine derivative
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The invention discloses a preparation method of a benzopyridazine derivative 5-bromobenzopyridazine; 1,2-diamino-3-nitrobenzene as a starting raw material is subjected to cyclization, reduction and Sandmeryer reaction to obtain the target product; the compound is an important pharmaceutical intermediate.
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Paragraph 0021; 0022
(2018/03/25)
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- ANTI-HCMV COMPOSITIONS AND METHODS
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This document relates to compounds useful as agents for preventing or treating human cytomegalovirus (HCMV) infections.
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Page/Page column 68;69
(2016/06/06)
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- 6,6-Fused heterocyclic ureas as highly potent TRPV1 antagonists
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A series of N-[{2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)-pyridin-3-yl}methyl] N′-(6,6-fused heterocyclic) ureas have been investigated as hTRPV1 antagonists. Among them, compound 15 showed highly potent TRPV1 antagonism to capsaicin, with Ki(ant) = 0.2 nM, as well as antagonism to other activators, and it was efficacious in a pain model. A docking study of 15 with our hTRPV1 homology model indicates that there is crucial hydrogen bonding between the ring nitrogen and the receptor, contributing to its potency.
- Sun, Wei,Kim, Hyo-Shin,Lee, Sunho,Jung, Aeran,Kim, Sung-Eun,Ann, Jihyae,Yoon, Suyoung,Choi, Sun,Lee, Jin Hee,Blumberg, Peter M.,Frank-Foltyn, Robert,Bahrenberg, Gregor,Schiene, Klaus,Stockhausen, Hannelore,Christoph, Thomas,Frormann, Sven,Lee, Jeewoo
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p. 803 - 806
(2015/02/19)
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- PERHYDROQUINOXALINE DERIVATIVES USEFUL AS ANALGESICS
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The present invention relates to perhydroquinoxaline compounds according to the general formula (1), their use as a medicament, in particular as analgesic, antipruritic and antiinflammatory agents, and their preparation.
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Page/Page column 26; 63
(2014/12/12)
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- Studies toward the discovery of the next generation of antidepressants. Part 6: Dual 5-HT1A receptor and serotonin transporter affinity within a class of arylpiperazinyl-cyclohexyl indole derivatives
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Based on the previously reported discovery lead, 3-(cis-4-(4-(1H-indol-4-yl)piperazin-1-yl)cyclohexyl)-5-fluoro-1H-indole (2), a series of related arylpiperazin-4-yl-cyclohexyl indole analogs were synthesized then evaluated as 5-HT transporter inhibitors
- Zhou, Dahui,Zhou, Ping,Evrard, Deborah A.,Meagher, Kristin,Webb, Michael,Harrison, Boyd L.,Huryn, Donna M.,Golembieski, Jeannette,Hornby, Geoffrey A.,Schechter, Lee E.,Smith, Deborah L.,Andree, Terrance H.,Mewshaw, Richard E.
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p. 6707 - 6723
(2008/12/21)
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- Furazan ring opening upon treatment of benzofurazan with ethanolamine to yield quinoxalines
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Heating of benzofurazans with ethanolamine in the presence of catalytic amount of p-toluenesulfonic acid leads to quinoxalines.
- Samsonov
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experimental part
p. 2510 - 2512
(2009/02/05)
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- PYRAZOLE COMPOUNDS USEFUL IN THE TREATMENT OF INFLAMMATION
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There is provided compounds of formula (I), wherein R1, R2, Ra and Rb have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a lipoxygenase (e.g. 15-lipoxygenase) is desired and/or required, and particularly in the treatment of inflammation.
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Page/Page column 50
(2010/10/20)
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- Novel transient receptor potential vanilloid 1 receptor antagonists for the treatment of pain; Structure-activity relationships for ureas with quinoline, isoquinoline, quinazoline, phthalazine, quinoxaliue, and cinnoline moieties
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Novel transient receptor potential vanilloid 1 (TRPV1) receptor antagonists with various bicyclic heteroaromatic pharmacophores were synthesized, and their in vitro activity in blocking capsaicin activation of TRPV1 was assessed. On the basis of the contribution of these pharmacophores to the in vitro potency, they were ranked in the order of 5-isoquinoline > 8-quinoline = 8-quinazoline > 8-isoquinoline ≥ cinnoline ≈ phthalazine ≈ quinoxaline ≈ 5-quinoline. The 5-isoquinoline-containing compound 14a (hTRPV1 IC50 = 4 nM) exhibited 46% oral bioavailability and in vivo activity in animal models of visceral and inflammatory pain. Pharmacokinetic and pharmacological properties of 14a are substantial improvements over the profile of the high-throughput screening hit 1 (hTRPV1 IC50 = 22 nM), which was not efficacious in animal pain models and was not orally bioavailable.
- Gomtsyan, Arthur,Bayburt, Erol K.,Schmidt, Robert G.,Guo, Zhu Zheng,Perner, Richard J.,Didomenico, Stanley,Koenig, John R.,Turner, Sean,Jinkerson, Tammie,Drizin, Irene,Hannick, Steven M.,Macri, Bryan S.,McDonald, Heath A.,Honore, Prisca,Wismer, Carol T.,Marsh, Kennan C.,Wetter, Jill,Stewart, Kent D.,Oie, Tetsuro,Jarvis, Michael F.,Surowy, Carol S.,Faltynek, Connie R.,Lee, Chih-Hung
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p. 744 - 752
(2007/10/03)
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- ARYLPIPERAZINYL-CYCLOHEXYL INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION
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Compounds are provided which are useful for the treatment of serotonin-affected neurological disorders which comprise (I) wherein: Ra, R1, R2 and R3 are each, independently, hydrogen, or a substituent selected from halogen, CF3, alkyl, alkoxy, MeSO2, amino or aminocarbonyl (each optionally substituted by one or two groups selected from alkyl and benzyl) carboxy, or alkoxycarbonyl; or two adjacent of Ra and R1-4 together can form a 5-7 membered carbocyclic or heterocyclic ring which is optionally substituted by a substituent defined above; R4 is hydrogen, halogen, or alkyl; R5 is hydrogen, alkyl, arylalkyl, or aryl; R6 is hydrogen, halogen, CF3, CN, carbamide, alkoxy or benzyloxy; X1, X2 and X3 are each carbon or one of X1, X2 or X3 may be nitrogen; Y is CH or nitrogen; and Z is carbon or nitrogen; or pharmaceutically acceptable salts thereof.
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- The Gould-Jacobs reaction of 5-aminoquinoxaline
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Reaction of 5-aminoquinoxaline with alkoxymethylene derivatives affords the corresponding quinoxalinoaminoethylenes. These undergo a thermal cyclization to yield angularly annelated 10H-pyrido[2,3-f]quinoxalines. The structures of all products were deduced from their IR, UV, mass, 1H, and 13C NMR spectra.
- Salon, Jozef,Milata, Viktor,Pronayova, Nadezda,Lesko, Jan
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p. 293 - 299
(2007/10/03)
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- Carbon-13 NMR Studies on some 5-Substituted Quinoxalines
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Eleven 5-substituted quinoxalines (NO2, NH2, COOH, OCH3, CH3, OH, F, Cl, Br, I, CN, the latter five not reported previously) have been synthesized by standard methods.Their 13C NMR spectra have been measured in DMSO-d6 and assigned on the basis of substituent parameters, by line widths and by intensities.The chemical shifts compare favorably with those calculated using benzene substituent parameters, and are very close to those of corresponding carbons in 1-substituted phenazines.The correlation with the chemical shifts of the corresponding positions in 1-substituted naphthalenes is also close except for those of carbons 4a and 8a in the quinoxalines which, due to their proximity to nitrogen, are downfield (in some cases 12 ppm) of the signals of the corresponding carbons in naphthalene. 5-Fluoroquinoxaline was also measured in CDCl3, CD3COCD3, CD3CN, CD3OD, C6D6 and CD3COOD.In all solvents an abnormally low 2J(CF) (ca. 12 Hz) was found for C-4a and no C-F spin-spin splitting could be detected for the three-bond coupling of C-8a.Similar abnormalities were found in 2-fluoroaniline and 2-fluoroacetanilide.There are linear relationships between the Q parameter of the substituent and the chemical shift of carbons 4a, 5 and 6.A linear relationship also exists between the chemical shift of C-8 ('para' position) and the Hammett ?p parameter of the substituent.
- Hollstein, Ulrich,Krisov, Galen E.
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p. 300 - 304
(2007/10/02)
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