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Review

Pyrazine derivatives: a patent review (June 2012 – present)

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Bibliography

  • Barlin GB. Chemistry of heterocyclic compounds. John Wiley and Sons; New York: 1982
  • Bird CW. Heteroaromaticity, 5, a unified aromaticity index. Tetrahedron 1992;48:335-40
  • Awwadi FF, Landee CP, Turnbull MM, et al. Low-dimensional quantum magnetic systems: synthesis, structure and magnetic behavior of (2,5-dimethylpyrazine)copper(ii) chloride and synthesis and magnetic behavior of bis(2,6-dimethylpyrazine)copper(ii) chloride. Polyhedron 2005;24:2153-9
  • Joule JA, Mills K. Heterocyclic Chemistry. Wiley-Blackwell; Chichester: 2010
  • Brown CJIII, Knaust JM. 2,5-Dimethylpyrazine 1,4-dioxide. Acta Cryst Sect E Struct Rep Online 2009;65:o3052
  • Rajini RS, Aparna P, Sasikala C, Ramana CV. Microbial metabolism of pyrazines. Crit Rev Microbiol 2011;37:99-112
  • Woolfson A, Rothschild M. Speculating about pyrazines. Proc Royal Soc 1990;242:113-19
  • Maga JA. Pyrazine update. Food Rev Int 1992;8:479-558
  • Wagner R, Czerny M, Bielohradsky J, Grosch W. Structure-odour-activity relationships of alkylpyrazines. Z Lebensm Unters Forsch A 1999;208:308-16
  • Kikugawa K. Organochemical studies on the formation and the reduction of mutagenic and/or carcinogenic and the DNA damaging components in foods. Environ Mutagen Res 2004;26:23-31
  • Dolezal M. Biological active pyrazines of natural and synthetic origin. Chem Listy 2006;100:959-66
  • Dolezal M, Zitko J, Jampilek J. Pyrazinecarboxylic acid derivatives with antimycobacterial activity. In: Cardona PJ, Understanding tuberculosis - new approaches to fighting against drug resistance. InTech; Rijeka: 2012
  • Muller R, Rappert S. Pyrazines: occurrence, formation and biodegradation. Appl Microbiol Biotechnol 2010;85:1315-20
  • Yamaguchi T. The relationship between the chemical structures of dihydropyrazine derivatives and DNA strand-breakage activity. Chem Pharm Bull(Tokyo) 2007;55:532-6
  • Miniyar PB, Murumkar PR, Patil PS, et al. Unequivocal role of pyrazine ring in medicinally important compounds: a review. Mini Rev Med Chem 2013;13:1607-25
  • Achelle S, Baudequin C, Plé N. Luminescent materials incorporating pyrazine or quinoxaline moieties. Dyes Pigments 2013;98:575-600
  • Ferreira SB, Kaiser CR. Pyrazine derivatives: a patent review (2008 - present). Exp Opin Ther Pat 2012;22:1033-51
  • Hara T, Norimatsu N, Kurushima H, Kono T. Method for producing dichloropyrazine derivative. US024832; 2014
  • Wang Y, Wang L, Zhang Q. Synthesis method of pyrazine methylamine derivative. CN103214424; 2013
  • Chuanbao W. Chiral synthesis of eszopiclone. CN102675318; 2012
  • Chuanbao W. Method for preparing dexzopiclone. CN102675319; 2012
  • Yisi F, Fengfeng Z, Zhongqiu X, et al. Synthetic method of bortezomib. CN102659919; 2012
  • Pi J, Ding Y, Yin D, et al. Novel synthesis route of glipizide. CN102993106; 2013
  • Mantegazza S, Attolino E, Allegrini P. Process for the preparation of a viral protease inhibitor telaprevir and its intermediates. WO131978; 2013
  • Nandi S, Sivakumaran M. An improved process for the preparation of telaprevir. IN2012CH04278; 2014
  • Lehmann F, Bremberg U, Soelver E, et al. Process for manufacturing of kinase inhibitors. WO089636; 2013
  • Jenmalm JA, Lehmann F, Nilsson BM, et al. Pyrazine derivatives and their use as protein kinase inhbitors. WO095399A2; 2009
  • Kushner S, Dalalian H, Sanjurjo JL, et al. Experimental chemotherapy of tuberculosis. 2. The synthesis of pyrazinamides and related compounds. J Am Chem Soc 1952;74:3617-21
  • Singh SB, Tomassini JE. Synthesis of natural flutimide and analogous fully substituted pyrazine-2,6-diones, endonuclease inhibitors of Influenza virus. J Org Chem 2001;66:5504-16
  • Furuta Y, Takahashi K, Shirakib K, et al. T-705 (favipiravir) and related compounds: novel broad-spectrum inhibitors of RNA viral infections. Antiviral Res 2009;82:95-102
  • Edelman MJ, Meyers FJ, Grennan T, et al. Phase II trial of pyrazine diazohydroxide in androgen-independent prostate cancer. Invest New Drugs 1998;16:179-82
  • Ambrogi V, Cozzi P, Sanjust P, et al. Anti-lipolytic activity of a series of pyrazine-N-oxides. Eur J Med Chem 1980;15:157-63
  • Roblin RO, Williams JH, Winnek PS, English JP. Chemotherapy: II. Some sulfanilamide heterocycles. J Am Chem Soc 1940;62:2002-5
  • Ambrogi V, Bloch K, Parenti MA, et al. Synthesis of pyrazine derivatives as potential hypoglycemic agents. J Pharm Sci 1972;61:1483-9
  • Adams J, Ma YT, Stein R, et al. Boronic ester and acid compounds. US5780454; 1996
  • France CP, Winger G, Medzihradsky F, et al. Mirfentanil: pharmacological profile of a novel fentanyl derivative with opioid and nonopioid effects. J Pharmacol Exp Ther 1991;258:502-10
  • Coe JW, Brooks PR, Vetelino MG, et al. Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation. J Med Chem 2005;48:3474-7
  • Zeuzem S, Andreone P, Pol S, et al. Telaprevir for retreatment of HCV. infection. N Engl J Med 2011;25:2417-28
  • Cragoe EJ. (3-Amino-5,6-disubstituted-pyrazinoyl)guanidines. BE639386; 1964
  • Foreman MM, Hanania T, Stratton SC, et al. In vivo pharmacological effects of JZP-4, a novel anticonvulsant, in models for anticonvulsant, antimania and antidepressant activity. Pharmacol Biochem Behav 2008;89:523-34
  • Cotrel C, Jeanmart C, Messer MN. Pyrrolo(3,4-b)pyrazine derivatives. DE2300491; 1973
  • Clapper ML. Chemopreventive activity of oltipraz. Pharmacol Ther 1998;78:17-27
  • Gluchowski C. 2-Imidazolin-2-ylamino)tetrahydroquinoxalines and methods for using same. EP 0422878; 1991
  • Pollard JR, Reaper PM, Asmal M. Compounds useful as inhibitors of ATR kinase and combinations thereof for treatment of various diseases such as cancer. WO152298; 2013
  • Charrier JD, Young SC, Davis CJ, et al. Preparation of pyrazineamine derivatives useful as inhibitors of ATR kinase in the treatment of cancer. WO049719; 2013
  • Charrier JD, Storck PH, Studley J, et al. Preparation of pyrazineamine derivatives useful as inhibitors of ATR kinase in the treatment of cancer. WO049720; 2013
  • Charrier JD, Storck PH, Studley J, et al. Preparation of pyrazineamine derivatives useful as inhibitors of ATR kinase in the treatment of cancer. WO049722; 2013
  • Charrier JD, Studley J, Pierard FYTM, et al. Preparation of aminopyrazine-isoxazole derivatives useful as inhibitors of ATR kinase. WO049726; 2013
  • Charrier JD, Durrant SJ, Knegtel R. Preparation of pyrazine derivatives useful as inhibitors of ATR kinase. US20130115310; 2013
  • Charrier JD, Durrant SJ, Shaw DM. Preparation of pyrazine derivatives useful as inhibitors of ATR kinase. US0115311; 2013
  • Charrier JD, Storck PH, Pinder J, Studley JR. Preparation of pyrazine derivatives useful as inhibitors of ATR kinase. US0115312; 2013
  • Charrier JD, O’Donnell ME, Everitt SR. Preparation of pyrazine derivatives useful as inhibitors of ATR kinase. US0115313; 2013
  • Charrier JD, Kay D. Preparation of pyrazine derivatives useful as inhibitors of ATR kinase. US20130115314; 2013
  • Charrier JD, Pinder J, Storck PH. Preparation of substituted isoxazolylpyrazinamines as inhibitors of ATR kinase. US0107093; 2014
  • Charrier JD, Durrant SJ, Kay D, et al. Compounds useful as inhibitors of ATR kinase. US113005; 2014
  • Pollard JR, Reaper PM. Treating pancreatic cancer and non-small cell lung cancer with ATR kinase inhibitors. WO049859; 2013
  • Fokas E, Prevo R, Pollard JR, et al. Targeting ATR in vivo using the novel inhibitor VE-822 results in selective sensitization of pancreatic tumors to radiation. Cell Death Dis 2012;3:e441
  • Song Y, Xu Q, Jia Z, et al. Preparation of pyrazine derivatives for use as Syk kinase activity inhibitors. US0131040; 2013
  • Boyle RG, Boyce RJ. Pharmaceutically active pyrazine derivatives. WO072502; 2013
  • Li GQ, Hasvold LA, Tao ZF, et al. Synthesis and biological evaluation of 1-(2,4,5-trisubstituted phenyl)-3-(5-cyanopyrazin-2-yl)ureas as potent Chk1 kinase inhibitors. Bioorg Med Chem Lett 2006;16:2293-8
  • Collins I, Lainchbury M, Matthews TP, Reader JC. Preparation of 5-(pyridin-2-ylamino)pyrazine-2-carbonitrile compounds as CHK1 inhibitors. WO068755; 2013
  • Collins I, Lainchbury M, Matthews TP, Reader JC. 5-(pyridine-2-yl-aminop-pyrazine-2-carbonitrile compounds and their therapeutic use. AU2012335409; 2014
  • Wishart N, Bonafoux DF, Frank KE, et al. Preparation of imidazopyrrolopyrazine derivatives and analogs for use as protein kinase modulators. US0072470; 2013
  • Wang L, Qi C, He X, Zhang Q. Application of glipizide in preparing medicine for treating tumors. CN103622975; 2014
  • Lewis RT, Choquette D, Epstein O, et al. Aminodihydrothiazine and aminodioxodihydrothiazine compounds as beta-secretase antagonists and their preparation. WO059185; 2014
  • Ito Y, Kushida I, Mitasev B. Fused aminodihydrothiazine derivative salts as BACE1 inhibitors and their preparation. WO015125; 2014
  • Hall A, O’Connor DM. Fused aminodihydrothiazine derivatives. GB2504615; 2014
  • Hilpert H. Difluoro-hexahydro-cyclopentaoxazinyls and difluoro-hexahydro-benzoxazinyls as BACE1 inhibitors and their preparation. WO001228; 2014
  • Borroni E, Gobbi L, Hilpert H, et al. [1,3]Oxazines as BACE inhibitors and their preparation and use as imaging agents and in the treatment of Alzheimer’s disease and diabetes. WO168175; 2012
  • Le Clerq LC, Bartolome-Nebreda JM, Conde-Ceide S, Van Gool MLM. Inhibitors of phosphodiesterase 10 enzyme. WO009305; 2014
  • Coskran TM, Morton D, Menniti FS, et al. Immunohistochemical localization of phosphodiesterase 10A in multiple mammalian species. J Histochem Cytochem 2006;54:1205-13
  • Bartolome-Nebreda JM, Conde-Ceide S, MacDonald GJ, et al. Preparation of imidazo[1,2–a]pyrazine derivatives and their use for the prevention or treatment of neurological, psychiatric and metabolic disorders and diseases. WO110545; 2011
  • Bartolome-Nebreda JM, Delgado F, Martin-Martin ML, et al. Discovery of a Potent, Selective, and Orally Active Phosphodiesterase 10A Inhibitor for the Potential Treatment of Schizophrenia. J Med Chem 2014;57:4196-212
  • Cambell JE, Jones P. Triazolo-pyrazine derivatives useful in the treatment of disorders of the central nervous system. WO085284; 2014
  • Galley G, Norcross R, Pflieger P. Preparation of pyrazine derivatives as inhibitors of TAARs. WO072257; 2014
  • Graham ES, Ashton JC, Glass M. Cannabinoid receptors: a brief history and "what’s hot". Front Biosci 2009;14:944-57
  • Bissantz C, Dhurwasulu B, Grether U, et al. Preparation of novel pyrazine derivatives a CB2 agonist. WO060751; 2013
  • Dhurwasulu B, Grether U, Nettekoven M, et al. Novel pyrazine derivatives as CB2 receptor agonists. WO086807; 2014
  • Woodward RM. Use of opioid receptor antagonist for gastrointestinal tract disorders. MX003310; 2012
  • Bylock LA. Oxadiazoles as inhibitors of leukotriene production for combination therapy and their preparation. WO0195879; 2013
  • Sitbon O, Morrell N. Pathways in pulmonary arterial hypertension: the future is here. Eur Respir Rev 2012;21:321-7
  • Li T, Patel S, Perner RJ, et al. Preparation of octahydropyrrolopyrazine sulfonamide derivatives for use as calcium channel blockers. WO049174; 2013
  • Gillis EP, Bowsher S, Scola PM. Preparation of peptide hepatitis C virus inhibitors that target NS3 protease. WO071007; 2014
  • Romano KP, Ali A, Aydin C, et al. The molecular basis of drug resistance against hepatitis C virus NS3/4A protease inhibitors. PLoS Pathog 2012;8:15
  • Hirsh AJ, Sabater JR, Zamurs A, et al. Evaluation of second generation amiloride analogs as therapy for cystic fibrosis lung disease. J Pharmacol Exp Ther 2004;311:929-38
  • Bhalay G, Budd E, Bloomfield GC, et al. Treating diseases mediated by blockade of epithelial sodium channel with pyrazine-2-carboxamide derivatives. US171421; 2014
  • Bhalay G, Edwards L, Howsham C, et al. Preparation of pyrazine derivatives as epithelial sodium channel blockers. US0113914; 2014
  • Hamprecht D, Heckel A, Kley J. N-(Pyrazinecarbonyl)guanidines as epithelial sodium channel inhibitors and processes for the preparation thereof. WO174757; 2013
  • Heckel A, Blum A, Hamprecht D, Kley J. Preparation of heterocyclic compounds for treating lung and airways diseases. US0157981; 2013
  • Heckel A, Frattini S, Hamprecht D, Kley J. Heterocyclic compounds, medicaments comtaining said compounds use thereof and processes for the preparation thereof. US0109697; 2013
  • Johnson MR. Preparation of 3,5-diamino-6-chloro-N-(N-(4-(4-(2-hexyl(2,3,4,5,6-penta-hydroxyhexyl)amino)ethoxy)phenyl)butyl)carbamimidoyl)pyrazine-2-carboxamide isomers as sodium channel blockers for therapy. WO003386; 2013
  • Johnson MR. Chloro-pyrazine carboxamide derivatives with epithelial sodium channel blocking activity. US171447; 2014
  • Feng T, Sanganee HJ, Wada H. Pyrazine derivatives. US123275; 2013
  • Berg S, Bergh M, Hellberg S, et al. Discovery of novel potent and highly selective glycogen synthase kinase-3 beta (GSK3 beta) inhibitors for alzheimer’s disease: design, synthesis, and characterization of pyrazines. J Med Chem 2012;55:9107-19
  • Younis Y, Chibale K, Witty MJ, Waterson D. Preparation of aminopyrazine compounds as antimalarial agents for treatment of malaria. WO121387; 2013
  • Van Voorhis WC, Hol WGJ, Larson ET, et al. Compositions and methods for treating toxoplasmosis, cryptosporidiosis, and other apicomplexan protozoan related diseases. US018040; 2013
  • Vidadala RSR, Ojo KK, Johnson SM, et al. Development of potent and selective plasmodium falciparum calcium-dependent protein kinase 4 (PfCDPK4) inhibitors that the transmission of malaria to mosquitoes. Eur J Med Chem 2014;74:562-73
  • Mendez S, Traslavina R, Hinchman M, et al. The antituberculosis drug pyrazinamide affects the course of cutaneous leishmaniasis in vivo and increases activation of macrophages and dendritic cells. Antimicrob Agents Chemother 2009;53:5114-21
  • Welch JT, Mendez S, Cynamon MH. Pyrazinamide for immunostimulation and the treatment of leishmaniases. US157396; 2012

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