Author: Jessica.F

On May 19, 2011, Epstein, David M.; Jin, Meizhong; Mulvihill, Mark J. published a patent.Category: pyrazines The title of the patent was Preparation of deuterated heteroaryl compounds as tyrosine kinase inhibitors. And the patent contained the following:

The title compounds with general formula I [wherein X = independently N or C-A; Y = independently N or C; Z = N, C-H, C-D, or N-A; W = independently N, N=O, or C-B; G = Ph or pyridyl, either optionally substituted by one or more D or halogen atoms; R = absent, D, optionally substituted C1-10 alkyl, C3-10cycloalkyl, etc.; where A = independently H, D, halogen, CF3, etc.; B = Me, Et, H, D, etc.; with the proviso that at least one of Y and Z is N or N-A, at least one of W is N or N=O, and any hydrogen atom can be replaced by a D atom and the compound or salt is present as a material comprising at least one D atom in an abundance of at least about 10 %] or pharmaceutically acceptable salts thereof were prepared as inhibitors of IGF-1R and IR. For example, compound II was prepared in a multi-step synthesis. Compounds I may inhibit the activity of tyrosine kinase enzymes in animals, including humans, and are useful in the treatment and prevention of various diseases and conditions such as hyperproliferative disorders such as cancers. The experimental process involved the reaction of 3-(8-Chloroimidazo[1,5-a]pyrazin-3-yl)cyclobutanone(cas: 936901-72-3).Category: pyrazines

The Article related to preparation deuterated tyrosine kinase inhibitor quinoline imidazole triazine pyrazine, human treatment cancer hyperproliferative disorder antitumor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Category: pyrazines

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On September 21, 2006, Brittelli, David R.; Currie, Kevin S.; Darrow, James W.; Kropf, Jeffrey E.; Lee, Seung H.; Gallion, Steven L.; Mitchell, Scott A.; Pippin, Douglas A. I.; Blomgren, Peter A. published a patent.Electric Literature of 87486-34-8 The title of the patent was Preparation of substituted amides as Btk inhibitors. And the patent contained the following:

At least one chem. entity chosen from compounds I [R = (un)substituted cycloalkyl, aryl, heteroaryl; M = a bond, CH:CH; Q = CR10R11NR12, NR12CR10R11, NR13CO, CONR13, NR14CONR15 (wherein R10, R11 = H, alkyl, haloalkyl; R12-R15 = H, alkyl, haloalkyl, Ph, etc.); Z = (un)substituted phenylene, pyridylidene; W = (un)substituted heteroaryl other than imidazo[1,2-a]pyrazine; D = hydrogen bond donor other than hydrogen; with the provision] and pharmaceutically acceptable salts, solvates, chelates, non-covalent complexes, prodrugs, and mixtures thereof is described herein. E.g., a multi-step synthesis of II, starting from 3,5-dibromo-1H-pyridin-2-one, was given. Exemplified compounds I were tested in the Btk biochem. assay and certain of those compounds exhibited an IC50 value less than or equal to 1 μM. Some of the compounds I were also tested for inhibition of B-cell proliferation and T-cell proliferation. Pharmaceutical compositions comprising at least one chem. entity of the invention, together with at least one pharmaceutically acceptable vehicle chosen from carriers adjuvants, and excipients, are also described. Methods of treating patients suffering from certain diseases responsive to inhibition of Btk activity and/or B-cell activity are described. Methods for determining the presence of Btk in a sample are described. The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).Electric Literature of 87486-34-8

The Article related to amide preparation bruton’s tyrosine kinase btk inhibitor, b cell proliferation inhibitor amide preparation, t cell proliferation inhibitor amide preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Electric Literature of 87486-34-8

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On March 26, 2009, Blomgren, Peter A.; Currie, Kevin S.; Lee, Seung H.; Mitchell, Scott A.; Xu, Jianjun; Schmitt, Aaron C.; Zhao, Zhongdong; Zhichkin, Pavel E.; Stafford, Douglas G.; Kroft, Jeffrey E. published a patent.COA of Formula: C5H4Br2N2O The title of the patent was Preparation of pyrazinone substituted amides as Btk inhibitors. And the patent contained the following:

The title compounds I [X = N, CR2; Y = N, CR31; Z = N, CR3; provided that only one of X, Y and Z = N at a time; W = N, CH; V = CH, N; provided that one of W and V must be N and W and V are not both N; R1 = (un)substituted 4,5,6,7-tetrahydrobenzo[b]thien-2-yl, Ph, cyclohepta[b]thien-2-yl, etc.; R2 = H, Me, F, Cl, etc.; R21 = H, F; R3 = H, Me, CF3, F, etc.; R31 = H, Me, F, Cl, etc.; R4 = II (wherein m, n = 0-1; R5 = H, (un)substituted alkyl, cycloalkyl; R6 = H, (un)substituted alkyl; or NR5R6 = (un)substituted 4-6 membered cyclic ring having 0-1 addnl. N, S or O atoms; R7 = H, (un)substituted alkyl, cycloalkyl; R8 = H, (un)substituted alkyl; or NR7R8 = (un)substituted 4-6 membered cyclic ring having 0-1 addnl. N, S or O atoms; R9 = H, Me); R10 = OH, H, (un)substituted alkyl; R11 = H, Me, CF3] that inhibit Btk, were prepared E.g., a multi-step synthesis of III.CF3CO2H, starting from 4-nitrophenylacetic acid, was given. Exemplified compounds I were tested in the Btk biochem. assay and showed an IC50 of ≤ 2 μM, and certain of exemplified compounds I showed an IC50 of ≤ 1 μM. Pharmaceutical compositions comprising at least one compound I, together with at least one pharmaceutically acceptable vehicle chosen from carriers, adjuvants, and excipients, are described. Methods of treating patients suffering from certain diseases responsive to inhibition of Btk activity and/ or B-cell activity are described. Methods for determining the presence of Btk in a sample are described. The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).COA of Formula: C5H4Br2N2O

The Article related to pyrazinone amide benzamide preparation btk bruton’s tyrosine kinase inhibitor, antitumor combination chemotherapy btk inhibitor pyrazinone amide benzamide preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.COA of Formula: C5H4Br2N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On March 20, 2008, Whitney, James A.; Di Paolo, Julie; Valleca, Mark A.; Brittelli, David R.; Currie, Kevin S.; Darrow, James W.; Kropf, Jeffrey E.; Lee, Tony; Gallion, Steven L.; Mitchell, Scott A.; Pippen, Douglas A.I.; Blomgren, Peter A.; Stafford, Douglas Gregory published a patent.COA of Formula: C5H4Br2N2O The title of the patent was Preparation of substituted amides as Btk kinase inhibitors. And the patent contained the following:

Methods of inhibiting Btk activity by inhibiting phosphorylation of Y551 of Btk, methods of treating patients by inhibiting Btk activity by inhibiting phosphorylation of Y551 of Btk, chem. entities that bind to Btk and inhibited complexes are provided. Thus, the title compounds I [R = (un)substituted cycloalkyl, aryl, heteroaryl; M = a bond, CH:CH; Q = CR10R11NR12, NR12CR10R11, NR13CO, CONR13, NR14CONR15 (R10, R11 = H, alkyl, haloalkyl; R12-R15 = H, alkyl, haloalkyl, etc.); Z = (un)substituted phenylene, pyridylidene; W = (un)substituted heteroaryl other than imidazo[1,2-a]pyrazine; D = hydrogen bond donor other than H; with the proviso] were prepared E.g., a multi-step synthesis of II, starting from 3,5-dibromo-1H-pyridin-2-one, was given. Exemplified compounds I were tested in the Btk assay and certain of those compounds exhibited an IC50 value less than or equal to 1 μM. Some of the compounds I were tested in the B-cell proliferation assay and exhibited an IC50 value less than or equal to 10 μM. The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).COA of Formula: C5H4Br2N2O

The Article related to amide preparation bruton’s tyrosine kinase btk kinase inhibitor, y551 btk phosphorylation inhibitor amide preparation, b cell proliferation inhibitor amide preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.COA of Formula: C5H4Br2N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On March 24, 2005, Heeres, Jan; de Jonge, Marc R.; Koymans, Lucien M. H.; Daeyaert, Frits F. D.; Vinkers, Maarten; Van Aken, Koen J. A.; Arnold, Edward; Das, Kalyan; Kilonda, Amuri; Hoornaert, Georges J.; Compernolle, Frans; Cegla, Marek; Azzam, Rasha A.; Andries, Koen; de Bethune, Marie-Pierre; Azijn, Hilde; Pauwels, Rudi; Lewi, Paul J.; Janssen, Paul A. J. published an article.Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one The title of the article was Design, Synthesis, and SAR of a Novel Pyrazinone Series with Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitory Activity. And the article contained the following:

A series of novel pyrazinones designed as non-nucleoside reverse transcriptase inhibitors (NNRTIs) was synthesized and their anti-HIV structure-activity relationship (SAR) was studied. Optimization of activity was guided by mol. modeling, which in turn was based on x-ray structures of HIV-1 reverse transcriptase-bound 4-[[4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile (dapivirine). An example compound thus prepared and studied was 3-[(4-chlorophenyl)amino]-5-(2,4-dimethylphenoxy)-1-methyl-2(1H)-pyrazinone (I). The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one

The Article related to design synthesis structure activity pyrazinone nonnucleoside hiv reverse transcriptase, mol modeling phenylamino phenoxy pyrazinone hiv reverse transcriptase dapivirine, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On April 9, 2015, Chen, Yi published a patent.Formula: C5H4Br2N2O The title of the patent was Preparation of substituted [(6-phenyl-4-methyl-3-oxo-3,4-dihydropyrazin-2-yl)amino]benzene derivatives as inhibitors of bruton’s tyrosine kinase. And the patent contained the following:

The present invention provides compounds I [R0 and R1 = independently H, alkyl, alkenyl, alkynyl, cycloalkyl, etc.; L = N(Rd)(CH2)m; Rd = H, alkyl, alkenyl, alkynyl, cycloalkyl or heterocycloalkyl; m = 0-4; R2 = H or alkyl; R3 = H, halo, alkyl, or hydroxyalkyl; R4 = W, X, Y or Z; R5, R6, R7, R8, R9, R10, R11 and R12 = independently H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, halo, or alkoxy], or their N-oxides, pharmaceutically acceptable salts, solvates, polymorphs or tautomers. For example, compound II was prepared by coupling of compound III (preparation given) with compound IV (preparation given) followed by hydrolysis. The Kd value of compound II for bruton’s tyrosine kinase (BTK) was 0.86 nM, which clearly shows that compound II is a highly potent BTK inhibitor. The invention compounds are useful as inhibitors of bruton’s tyrosine kinase for the treatment of neoplastic disease, autoimmune disease and inflammatory disorder. The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).Formula: C5H4Br2N2O

The Article related to phenylmethyloxodihydropyrazinylaminobenzene compound preparation bruton tyrosine kinase inhibitor, neoplastic disease autoimmune disease inflammatory disorder treatment, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Formula: C5H4Br2N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On July 28, 2016, Chen, Yi published a patent.Product Details of 87486-34-8 The title of the patent was Preparation of substituted [(6-phenyl-4-methyl-3-oxo-3,4-dihydropyrazin-2-yl)amino]benzene derivatives as selective Bruton’s tyrosine kinase inhibitors. And the patent contained the following:

The invention provides compounds I [R0 and R1 = independently H, alkyl, alkenyl, alkynyl, cycloalkyl, etc.; L = N(Rd)(CH2)m; Rd = H, alkyl, alkenyl, alkynyl, cycloalkyl or heterocycloalkyl; m = 0-4; R2 = H or alkyl; R3 = H, halo, alkyl, or hydroxyalkyl; R4 = W, X, Y or Z; R5, R6, R7, R8, R9, R10, R11 and R12 = independently H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, halo, or alkoxy], or their N-oxides, pharmaceutically acceptable salts, solvates, polymorphs or tautomers. For example, compound II was prepared by coupling of compound III (preparation given) with compound IV (preparation given) followed by hydrolysis. The Kd value of compound II for Bruton’s tyrosine kinase (BTK) was 0.86 nM, which clearly shows that compound II is a highly potent BTK inhibitor. The invention compounds are useful as inhibitors of Bruton’s tyrosine kinase for the treatment of neoplastic disease, autoimmune disease and inflammatory disorder. The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).Product Details of 87486-34-8

The Article related to phenylmethyloxodihydropyrazinylaminobenzene compound preparation bruton tyrosine kinase inhibitor, neoplastic disease autoimmune disease inflammatory disorder treatment, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Product Details of 87486-34-8

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Coutant, Eloi P.; Goyard, Sophie; Hervin, Vincent; Gagnot, Glwadys; Baatallah, Racha; Jacob, Yves; Rose, Thierry; Janin, Yves L. published an article in 2019, the title of the article was Gram-scale synthesis of luciferins derived from coelenterazine and original insights into their bioluminescence properties.Formula: C26H21N3O3 And the article contains the following content:

An original gram-scale synthesis of O-acetylated forms of coelenterazine, furimazine or hydroxy-bearing analogs of luciferins is described. The comparison over two hours of their bioluminescence, using the nanoKAZ/NanoLuc luciferase, provides remarkable insights useful for the selection of a substrate adapted for a given application. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Formula: C26H21N3O3

The Article related to luciferin coelenterazine preparation bioluminescence kinetics light absorption, luciferase inhibition kinetics luciferin, Biomolecules and Their Synthetic Analogs: Others, Including Purines, Pyrimidine Nucleic Acid Bases, Flavins, Lignans and other aspects.Formula: C26H21N3O3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On June 9, 2022, Magalhaes, Carla M.; Esteves da Silva, Joaquim C. G.; Pinto da Silva, Luis published an article.Name: 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one The title of the article was Theoretical Study of the Thermolysis Reaction and Chemiexcitation of Coelenterazine Dioxetanes. And the article contained the following:

Coelenterazine and other imidazopyrazinones are important bioluminescent substrates widespread in marine species and can be found in eight phyla of luminescent organisms. Light emission from these systems is caused by the formation and subsequent thermolysis of a dioxetanone intermediate, whose decomposition allows for efficient chemiexcitation to singlet excited states. Interestingly, some studies have also reported the involvement of unexpected dioxetane intermediates in the chemi- and bioluminescent reactions of Coelenterazine, albeit with little information on the underlying mechanisms of these new species. Herein, we have employed a theor. approach based on d. functional theory to study for the first time the thermolysis reaction and chemiexcitation profile of two Coelenterazine dioxetanes. We have found that the thermolysis reactions of these species are feasible but with relevant energetic differences. More importantly, we found that the singlet chemiexcitation profiles of these dioxetanes are significantly less efficient than the corresponding dioxetanones. Furthermore, we identified triplet chemiexcitation pathways for the Coelenterazine dioxetanes. Given this, the chemiexcitation of these dioxetanes should lead only to minimal luminescence. Thus, our theor. investigation of these systems indicates that the thermolysis of these dioxetanes should only provide “dark” pathways for the formation of nonluminescent degradation products of the chemi- and bioluminescent reactions of Coelenterazine and other imidazopyrazinones. The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Name: 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

The Article related to dft thermolysis reaction chemiexcitation coelenterazine dioxetanes, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Name: 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

On July 31, 2020, Inouye, Satoshi; Sahara-Miura, Yuiko; Nakamura, Mitsuhiro; Hosoya, Takamitsu published an article.Category: pyrazines The title of the article was Expression, purification, and characterization of recombinant apoPholasin. And the article contained the following:

Pholasin is a reactive oxygen-sensitive photoprotein that consists of an apoprotein (apoPholasin) and an unknown chromophore. The preferred human codon-optimized apoPholasin gene was transiently expressed in mammalian cells and apoPholasin was detected using an anti-recombinant apoPholasin antibody. For the first time, we found that apoPholasin secreted into the culture medium could catalyze the oxidation of coelenterazine (CTZ, a luciferin) to produce continuous luminescence. The fusion protein of apoPholasin and glutathione S-transferase (GST-apoPholasin) was successfully expressed as a soluble form in bacterial cells using the cold induction system. The purified GST-apoPholasin also had luminescence activity with CTZ, showing the bioluminescence emission peak at 461 nm, and the resultant product showed purple blue fluorescence under 365 nm light. Unexpectedly, the main oxidation product of CTZ was identified as coelenteramine (CTM), not coelenteramide (CTMD). The experimental process involved the reaction of 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one(cas: 55779-48-1).Category: pyrazines

The Article related to apopholasin glutathione transferase coelenterazine reactive oxygen species oxidation, coelenteramide, coelenteramine, dehydrocoelenterazine, photoproteins, reactive oxygen and other aspects.Category: pyrazines

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem