Quinoxaline derivatives: a patent review (2006 – present)

Bibliography

• Bird CW. Heteroaromaticity. 5. A unified aromaticity index. Tetrahedron 1992;48:335-440
   Web of Science ®Google Scholar
• Gumus S. The aromaticity of substituted diazanaphthalenes. Comput Theor Chem 2011;963:263-7
   Web of Science ®Google Scholar
• Lumbroso H, Cure J, Konakahara T, A dipole-moment study of substituted pyrazines and quinoxalines. J Mol Struct 1980;68:293-305
   Web of Science ®Google Scholar
• McClellan AL. Tables of experimental dipole moments. Volume 1 W. H. Freeman; San Francisco: 1963. Volume 2 Rahara Enterprises; El Cerrito, CA: 1974
   Google Scholar
• Markgraf JH, Katt RJ. Strained heterocyclic systems. VI. Basicities of some quinoxalines. J Org Chem 1972;37:717-18
   Web of Science ®Google Scholar
• Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2912 ACD/Labs). Available from: https://scifinder.cas.org
   Google Scholar
• Carta A, Piras S, Loriga G, Chemistry, biological properties and SAR analysis of quinoxalinones. Mini Rev Med Chem 2006;6:1179-200
   PubMed Web of Science ®Google Scholar
• Carta A, Corona P, Loriga M. Quinoxaline 1,4-dioxide: a versatile scaffold endowed with manifold activities. Curr Med Chem 2005;12:2259-72
   PubMed Web of Science ®Google Scholar
• Zhou M, Huang J, Xu E, Conjugated polymer containing dithienopyrrole-quinoxaline, preparation method and uses thereof. WO2011143825A1; 2011
   Google Scholar
• Zhou M, Huang J, Xu E, Cyclopentadienedithiophene-quinoxaline conjugated polymer and preparation method and uses thereof. WO2011113194A1; 2011
   Google Scholar
• Fadhel O, Limmert M, Rothe C, Quinoxaline compounds and semiconductor materials. KR20110091547A; 2011
   Google Scholar
• Shitagaki T, Tokuda A, Abe H, Quinoxaline derivatives, and organic semiconductor devices, electroluminescent devices made by using the derivatives. KR20120034765A; 2012
   Google Scholar
• Sung C-J, Kim H-K, Shin J-K, Organic light emitting diode and method of fabricating the same. GB2485050A; 2012
   Google Scholar
• Funayama T, Shoji S, Otaka T. Vulcanized rubber laminate. US20100297452A1; 2010
   Google Scholar
• Ohnuki K, Yasuda Y, Ozaki T. Composition for semiconductive rubber, crosslinked rubber product, and semiconductive parts. WO2011046175A1; 2011
   Google Scholar
• Available from: http://ep.espacenet.com/
   Google Scholar
• Gil C, Campillo NE, Perez DI, Phosphodiesterase 7 (PDE7) inhibitors as new drugs for neurological and inflammatory disorders. Expert Opin Ther Pat 2008;18:1127-39
   Web of Science ®Google Scholar
• Levy I, Horvath A, Azevedo M, Phosphodiesterase function and endocrine cells: links to human disease and roles in tumor development and treatment. Curr Opin Pharmacol 2011;11:689-97
   PubMed Web of Science ®Google Scholar
• Keravis T, Lugnier C. Cyclic nucleotide phosphodiesterase (PDE) isozymes as targets of the intracellular signalling network: benefits of PDE inhibitors in various diseases and perspectives for future therapeutic developments. Br J Pharmacol 2012;165:1288-305
   PubMed Web of Science ®Google Scholar
• Malamas MS, Ni Y, Erdei JJ, Aryl and heteroaryl fused imidazo[1,5-a]pyrazines as inhibitors of phosphodiesterase 10. US2009143367A1; 2009
   Google Scholar
• Malamas MS, Ni Y, Erdei JJ, Substituted imidazo[1,5-a]quinoxalines as inhibitors of phosphodiesterase 10. TW201111383A; 2011
   Google Scholar
• Azami H, Kaizawa H, Kamijo K, Quinoxaline compounds. MX2011009314A; 2011
   Google Scholar
• Kaizawa H, Sugita M, Yamamoto H, Quinoxaline compound. WO2012033101A1; 2012
   Google Scholar
• Miller TW, Rexer BN, Garrett JT, Mutations in the phosphatidylinositol 3-kinase pathway: role in tumor progression and therapeutic implications in breast cancer. Breast Cancer Res 2011;13:224
   PubMed Web of Science ®Google Scholar
• Tamura N. Recent findings on phosphoinositide-3 kinase in rheumatic diseases. Nihon Rinsho Meneki Gakkai Kaishi 2012;35:8-13
   PubMedGoogle Scholar
• Gaillard P, Pomel V, Jeanclaude-etter I, Quinoxaline compounds and use thereof. WO2008101979A1; 2008
   Google Scholar
• Klein M, Emde U, Buchstaller H-P, Quinoxaline derivates. WO2012052102A1; 2012
   Google Scholar
• Lamb P, Matthews D. Combination therapies comprising quinoxaline inhibitors of PI3K-alpha for use in the treatment of cancer. MX2009010929A; 2009. or US2011123434A1; 2011
   Google Scholar
• Yongzhou H, Peng W, Lei Z, Benzenesulfonyl quinoxaline compound and preparation method and application thereof. CN101602737A; 2009
   Google Scholar
• Yongzhou H, Peng W, Yi S, Substituted quinoxalinamine compounds, and preparation method and application thereof. CN102250022A; 2011
   Google Scholar
• Chaudhari A, Dhanak D, Donatelli CA, Quinoxaline derivatives as PI3 kinase inhibitors. WO2008141065A1; 2008
   Google Scholar
• Knight SD, Parish CA, Ridgers LH, Quinoxaline derivatives as PI3 kinase inhibitors. WO20090211083A1; 2009
   Google Scholar
• Chaudhari A, Dhanak D, Donatelli CA, Quinoxaline derivatives as PI3 kinase inhibitors. TW200902008A; 2009
   Google Scholar
• Chen Y, Cushing TD, Hao X, Heterocyclic compounds and their uses. WO2008118454A2; 2008
   Google Scholar
• Chen Y, Cushing TD. Hao X, et al. delta3-Substituted quinoline or quinoxaline derivatives and their use as phosphatidylinositol 3-kinase (PI3K) inhibitors. WO2008118455A1; 2008. or MX2009010050A; 2009
   Google Scholar
• Chen Y, Cushing TD, Duquette JA, Heterocyclic compounds and their uses. WO2008118468A1; 2008
   Google Scholar
• Allen DR, Buckley GM, Burli R. Quinoxaline and quinoline derivatives as kinase inhibitors. WO2009081105A2; 2009
   Google Scholar
• Burli R, Haughan AF, Mack SR. Fused pyrazine derivatives as kinase inhibitors. WO2010052448A2; 2010
   Google Scholar
• Burli R, Haughan AF, Matteucci M, Quinoline and quinoxaline derivatives as kinase inhibitors. WO2011058110A1; 2011
   Google Scholar
• Allen DR, Brown JA, Burli R, Fused pyridine and pyrazine derivatives as kinase inhibitors. US2012077815A1; 2012
   Google Scholar
• Parton AH, Ali MH, Brookings DC, Quinoline and quinoxaline derivatives as kinase inhibitors. WO2012032334A1; 2012
   Google Scholar
• Roring M, Brummer T. Aberrant B-Raf signaling in human cancer - 10 years from bench to bedside. Crit Rev Oncog 2012;17:97-121
   PubMedGoogle Scholar
• Santarpia L, Lippman SM, El-Naggar AK. Targeting the MAPK-RAS-RAF signaling pathway in cancer therapy. Expert Opin Ther Targets 2012;16:103-19
   PubMed Web of Science ®Google Scholar
• Ramurthy S, Renhowe PA, Subramanian S. 2,6-Disubstituted quinazolines, quinoxalines, quinolines and isoquinolines as inhibitors of Raf kinase for treatment of cancer. WO2005037285A1; 2005. or MXPA06003607A; 2006
   Google Scholar
• Bemis GW, Duffy JP. Quinoxaline useful as inhibitor of protein kinase. JP2008069178A; 2008
   Google Scholar
• Efremov DG, Laurenti L. The Syk kinase as a therapeutic target in leukemia and lymphoma. Expert Opin Investig Drugs 2011;20:623-36
   PubMed Web of Science ®Google Scholar
• Pamuk ON, Tsokos GC. Spleen tyrosine kinase inhibition in the treatment of autoimmune, allergic and autoinflammatory diseases. Arthritis Res Ther 2010;12:222
   PubMed Web of Science ®Google Scholar
• Amar S, Belmaker RH, Agam G. The possible involvement of glycogen synthase kinase-3 (GSK-3) in diabetes, cancer and central nervous system diseases. Curr Pharm Des 2011;17:2264-77
   PubMed Web of Science ®Google Scholar
• Wu W, Sun XH. Janus kinase 3: the controller and the controlled. Acta Biochim Biophys Sin (Shanghai) 2012;44:187-96
   PubMed Web of Science ®Google Scholar
• Gerspacher M, Furet P, Vangrevelinghe E, Quinoxaline derivatives as inhibitors of the tyrosine kinase activity of janus kinases. WO2008148867A2; 2008.TW200904814A; 2009. or MX 2009013218A; 2009; between others
   Google Scholar
• Furet P, Graus Porta D, Guagnano V, Derivatives of quinolines and quinoxalines as protein tyrosine kinase inhibitors. WO2009141386A1; 2009. or NZ588511A; 2012; between others
   Google Scholar
• Foldynova-Trantirkova S, Wilcox WR, Krejci P. Sixteen years and counting: the current understanding of fibroblast growth factor receptor 3 (FGFR3) signaling in skeletal dysplasias. Hum Mutat 2012;33:29-41
   PubMed Web of Science ®Google Scholar
• Saxty G, Murray CW, Berdini V, Pyrazolyl quinazoline kinase inhibitors. WO2011135376A1; 2011
   Google Scholar
• Saxty G, Murray CW, Berdini V, Substituted benzopyrazin derivatives as FGFR kinase inhibitors for the treatment of cancer diseases. WO2012073017A1; 2012
   Google Scholar
• Choi WS, Kim YM. Composition for preventing and treating of allergic diseases comprising 4-chlorotetrazolo[1,5-a]quinoxaline and derivatives. KR20110136960A; 2011
   Google Scholar
• Rivera J, Olivera A. A current understanding of Fc epsilon RI-dependent mast cell activation. Curr Allergy Asthma Rep 2008;8:14-20
   PubMed Web of Science ®Google Scholar
• Crassous PA, Denis C, Paris H, Senard JM. Interest of alpha2-adrenergic agonists and antagonists in clinical practice: background, facts and perspectives. Curr Top Med Chem 2007;7:187-94
   PubMed Web of Science ®Google Scholar
• Wheeler LA, Woldemussie E, Lai RK. Methods for treating retinal diseases. US2006089361A1; 2006. or JP2007291129A; 2007
   Google Scholar
• Olejnik O, Kerslake E. Composition containing alpha-2-adrenergic agonist component. JP2008231122A; 2008
   Google Scholar
• Benedini F, Impagnatiello F, Biondi S, Derivatives of alpha2-adrenergic receptor agonist. US2008318965A1; 2008
   Google Scholar
• Gresele P, Momi S. Pharmacologic profile and therapeutic potential of NCX 4016, a nitric oxide-releasing aspirin, for cardiovascular disorders. Cardiovasc Drug Rev 2006;24:148-68
   PubMed Web of Science ®Google Scholar
• McCormich KD, Shih N-Y, Fevrier S, 3,4-dihydro-1,4-benzoxazine, 3,4-dihydro-1,4-benzothiazine and 1,2,3,4-tetrahydro-quinoxaline derivatives as alpha2C adrenoreceptor agonists. WO2008100463A1; 2008.KR20090111345A; 2009. or ZA200906127A; 2010; between others
   Google Scholar
• Zhou HY, Hu GX, Lian QQ, The metabolism of steroids, toxins and drugs by 11beta-hydroxysteroid dehydrogenase 1. Toxicology 2012;292:1-12
   PubMed Web of Science ®Google Scholar
• Braun AJ, Gussregen S, Mougenot PR, New N-(pyrrolidino- or piperidino-carbonyl)-tetrahydro-benzazines, are 11 beta-hydroxysteroid dehydrogenase type 1 modulators useful e.g. for treating obesity, diabetes or hypertension. FR2902790A1; 2007
   Google Scholar
• Aletru M, Braun AJ, Gussregen S, New N-(tropanyl-carbonyl)-tetrahydro-benzazines, are 11 beta-hydroxysteroid dehydrogenase type 1 modulators useful e.g. for treating obesity, diabetes or hypertension. FR2902791A1; 2007
   Google Scholar
• Braun A, Crespin O, Namane C, New tetrahydroquinoxaline urea derivatives are 11 beta-hydroxysteroid dehydrogenase type 1 modulators useful to treat/prevent e.g. obesity, diabetes, insulin resistance, metabolic syndrome, glaucoma, Cushing's syndrome and hypertension. FR2926817A1; 2009
   Google Scholar
• Braun A, Crespin O, Namane C, New tetrahydroquinoxaline urea derivatives are 11 beta-hydroxysteroid dehydrogenase type 1 modulators useful to treat/prevent e.g. obesity, diabetes, insulin resistance, metabolic syndrome, glaucoma, Cushing's syndrome and hypertension. FR2934858A1; 2010
   Google Scholar
• Stone TW, Ceruti S, Abbracchio MP. Adenosine receptors and neurological disease: neuroprotection and neurodegeneration. Handb Exp Pharmacol 2009;193:535-87
   PubMedGoogle Scholar
• Koscso B, Csoka B, Pacher P, Investigational A3 adenosine receptor targeting agents. Expert Opin Investig Drugs 2011;20:757-68
   PubMed Web of Science ®Google Scholar
• Schann S, Mayer S, Gardan S, Pyrrolo[1,2-a]quinoxaline derivatives as adenosine A3 receptor modulators and uses thereof. US2009093476A1; 2009
   Google Scholar
• Harris JM, Neustadt BR, Liu H, Amino-quinoxaline and amino-quinoline compounds for use as adenosine A2A receptor antagonists. US20110105513A1; 2011
   Google Scholar
• Qaisi AMA, Al-Hiari YMA, Zahra JAY, Quinoline and pyridoquinoxaline derivatives useful as anticancer and/or antibacterial agents. GB2442951A; 2008
   Google Scholar
• Boese R, El-Abadelah MM, Zahra JA, Indolo[2,3-b]-, Indeno[1,2-b]- and Indeno[2,1-b]pyrido[2,3-f] quinoxaline-3-carboxylic acids and esters, processes for their preparation and their use as antiviral, antibiotic and antitumor agents. EP2128160A1; 2009
   Google Scholar
• Cirrincione G, Diana P. Isoindolo-quinoxaline derivatives having antitumor activity, process for their production and their use. WO2008041264A1; 2008
   Google Scholar
• Deleuze-Masquefa C, Moarbess G, Bonnet P-A, Imidazol[1,2-alpha]quinoxalines and derivatives for the treatment of cancers. US20100249142A1; 2010
   Google Scholar
• Liping D. Pyrazolo N-substituted dehydronorcantharidin imide derivative as well as synthesis method, activity test method and application thereof. CN101812066A; 2010
   Google Scholar
• Li W, Xie L, Chen Z, Cantharidin, a potent and selective PP2A inhibitor, induces an oxidative stress-independent growth inhibition of pancreatic cancer cells through G2/M cell-cycle arrest and apoptosis. Cancer Sci 2010;101:1226-33
   PubMed Web of Science ®Google Scholar
• Claus E, Czech M, Gerlach M, Chinoxalin derivatives and use thereof for treating malignant and benign tumour illnesses. EP2241557A1; 2010. or MX2011010329A; 2011
   Google Scholar
• Natarajan A, Chen Q, Bryant V, Quinoxaline compounds and uses thereof. WO2012071414A2; 2012
   Google Scholar
• Ramesh B, Bharani S, Ramakrishma D, Metal complexes with anticancer activity. US20100209537A1; 2010
   Google Scholar
• Gust R, Ott I, Sheldrick WS, Octahedral metal (III) polypyridyl complexes and their use in prevention and treatment of cancer. EP2072521A1; 2009
   Google Scholar
• Oohara N, Nakatsui K, Mayama D, Antitumor agent. WO2011129365A1; 2011
   Google Scholar
• Venable JD. Quinoxaline compounds. MXPA06003578AA; 2006
   Google Scholar
• Gong Y-D, Cho H, Jeon M-K, Novel 3-chloro-5-substituted-quinoxaline-2-amine derivatives and pharmaceutically acceptable salt thereof, method for preparation, therapeutic agent for inflammatory disease induced by SPC activity containing 3-chloro-5-substituted-quinoxaline-2-amine derivatives as an effective ingredient. WO2009041789A2; 2009
   Google Scholar
• Goehring RR, Matsumura A, Shao B, Substituted-quinoxaline-type-piperidine compounds and the uses thereof. EP2433937A1; 2012
   Google Scholar
• Fioravanti B, Vanderah TW. The ORL-1 receptor system: are there opportunities for antagonists in pain therapy? Curr Top Med Chem 2008;8:1442-51
   PubMed Web of Science ®Google Scholar
• Tadesse D, Tafesse L, Zhou X, Phosphorus-substituted quinoxaline-type piperidine compounds and uses thereof. WO2012085648A1; 2012
   Google Scholar
• Qaisi AMA, Al-Hiari YMA, Zahra JAY, Quinoline and pyridoquinoxaline derivatives as antibacterial agents. EP1721898A1; 2006
   Google Scholar
• Daines RA, Price AT. Antibacterial agents. WO2007016610A2; 2007
   Google Scholar
• Miller WH, Seefeld MA. Antibacterial Agents. US2007244091A1; 2007
   Google Scholar
• Sugiyama T, Kato A. Quinoxaline-based compound or salt thereof, and industrial microbicide composition. JP2010173957A; 2010
   Google Scholar
• Sugiyama T, Kato A, Ishikawa H, Quinoxaline compound or salt thereof and industrial bactericidal composition. JP2011037776A; 2011
   Google Scholar
• Antonik LM, Khabibulina AFG, Fadeeva TJV, Complex of polyvinylpyrrolidone and 2,3-bis-(hydroxymethyl)quinoxaline 1,4-di-N-oxide (dioxydinum) and it using as antibacterial complex with prolonged effect. RU2304589C1; 2007
   Google Scholar
• Saveliiev YV, Markovska LA, Saveliieva OO, Bactericide foam-polyurethane dressing “SMS-PUR-DERM” for medical purposes. UA20282U; 2007
   Google Scholar
• Saveliier YV, Markovska LA, Saveliieva OO, Process for the preparation of foamed polyurethanes possessing biocompatibility and bactericidal activity. UA81077C2; 2007
   Google Scholar
• Gai Y, Or YS, Wang Z, Quinoxaline-containing compounds as hepatitis C virus inhibitors. TW200938550A; 2009
   Google Scholar
• Harper S, Summa V, Liverton N, Macrocyclic quinoxaline compounds as HCV NS3 protease inhibitors. CA2731177A1; 2010. or MX2011000826A; 2011
   Google Scholar
• Chang G, Didiuk MT, Finneman J, 1,2,4-Substituted 1,2,3,4-tetrahydro- and 1,2-dihydro-quinoline and 1,2,3,4-tetrahydro-quinoxaline derivatives as CETP inhibitors for the treatment of atherosclerosis and obesity. BRPI0408897A; 2006
   Google Scholar
• Gybock H, Johansson M, Minidis A, Saturated quinoxaline derivatives and their use as metabotropic glutamate receptor ligands. BRPI0406810A; 2005
   Google Scholar
• Koehler MFT, Goldsmith R, Sutherlin DP, Quinoxaline inhibitors of the Hedgehog signalling pathway. KR20070005736A; 2007
   Google Scholar
• Bladh H, Larsson J. Quinoxaline derivatives as neutrophil elastase inhibitors and their use. HK1089163A1; 2008
   Google Scholar
• Boyle RG, Travers S. Quinoline and quinoxaline N-oxides as CHK-1 inhibitors. WO2008015423A1; 2008
   Google Scholar
• Mohr P, Bleicher K, Christ AD, 1-(1-Benzylpiperidin-4-yl)benzimidazole-5-carboxylic acid derivatives for the treatment of diabetes mellitus. MX2009010731A; 2009
   Google Scholar
• Gong YD, Jeon MK, Lee TH, Quinoxaline derivatives and pharmaceutically acceptable salt thereof having MCH1R inhibitory activity, process for preparation and use thereof for treating obesity. KR20090090792A; 2009
   Google Scholar
• Habashita S, Hirai S-I, Ohashi Y, Preventive or remedy for posterior eye disease containing quinazolinone derivative or quinoxaline derivative as the active ingredient. WO2009041566A1; 2009
   Google Scholar
• Kireshita S, Hirai S. Prophylactic or therapeutic agent for keratoconjuctival disorder comprising quinazolinone derivative or quinoxaline derivative as active ingredient. JP2009096804A; 2009
   Google Scholar
• Gavish M, Veenman JA, Shterenberg A, Heterocyclic derivatives, pharmaceutical compositions and methods of use thereof. US20100029658A1; 2010
   Google Scholar
• Ishizuka N, Sakai K, Hayashi K. New utilities of tricyclic compounds. EP2168576A2; 2010
   Google Scholar
• Hu B, Wrobel JE, Jetter JW, Quinoxaline-based LXR modulators. WO2010054229A1; 2010
   Google Scholar
• Moon H-S, Yang J-S, Kim M-K, Novel quinoxaline derivatives. WO2011122815A2; 2011
   Google Scholar
• Jeon MK, Lee TH, Hwang SH, 2-Substituted 6-(biphenyl-4-carboxamido)quinoxaline derivatives and pharmaceutically acceptable salt thereof having MCH1R inhibitory activity, process for preparation and use thereof for treating obesity. KR20110094573A; 2011
   Google Scholar
• Choi DK, Lee HS, Kim IS, 8-Phenyl-6a,7,8,9,9a,10-hexahydro-6H-isoindolo[5,6-g]quinoxaline-7,9-dione(PHID) with neuronal cell death inhibitory activity and the pharmaceutical composition comprising the same for prevention and treatment of neurodegenerative disease. KR20110059939A; 2011
   Google Scholar
• Choi SU, Ahn JH, Kim KR, Novel quinoxaline derivatives and composition for inducing differentiation of stem cells into neural cells comprising same. KR20110028932A; 2011
   Google Scholar
• Colon M, Fitch DM, Prolyl hydroxylase inhibitors. CN101983384A; 2011
   Google Scholar
• Nishiyama T. Indolo[2,3-b]quinoxaline compound having erythropoietin production-promoting effect. JP2011105659A; 2011
   Google Scholar