- Synthesis of new triazole based imidazo[1,2-a]pyrazine-benzimidazole conjugates: H-bonding assisted FRET efficient ratiometric detection of pyrophosphate
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Triazole tethered imidazo[1,2-a]pyrazine-benzimidazole conjugates 13-38 has been synthesized by click and Suzuki-Miyaura cross coupling reactions at C-8 and C-6 positions, respectively. The research findings clearly predicted that by modification of electronic structure of the receptor, the sensitivity of the recognition process could be modified. Compound 24 with hydroxyphenyl substituent, showed stronger binding to the pyrophosphate than other compounds. Compound 24 has been used as selective probe for ratiometric detection of pyrophosphate amongst the other anions. The binding event of compound 24 toward PPi has been successfully evaluated by absorption and emission spectroscopy as well as NMR titration method. The compound 24 showed H-bonding assisted facilitation of FRET phenomenon in the presence of PPi.
- Goel, Richa,Luxami, Vijay,Paul, Kamaldeep
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Read Online
- Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 4: Design, synthesis and biological evaluation of novel imidazo[1,2-a]pyrazines
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Through a structure-guided core-refining approach, a series of novel imidazo[1,2-a]pyrazine derivatives were designed, synthesized and evaluated as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Biological results of antiviral assay in MT
- Huang, Boshi,Liang, Xin,Li, Cuicui,Chen, Wenmin,Liu, Tao,Li, Xiao,Sun, Yueyue,Fu, Lu,Liu, Huiqing,De Clercq, Erik,Pannecouque, Christophe,Zhan, Peng,Liu, Xinyong
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Read Online
- IMIDAZO[1,2-A]PYRAZINE MODULATORS OF THE ADENOSINE A2A RECEPTOR
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The present invention relates to the compound of formula (I) and salts, stereoisomers, tautomers, isotopologues,or N-oxides thereof. The present invention is further concerned with the use of such a compound or salt, stereoisomer, tautomer, isotopologues,or N-oxide thereof as medicament and a pharmaceutical composition comprising said compound.
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Page/Page column 82
(2019/01/17)
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- Investigation of rotameric conformations of substituted imidazo-[1,2-a] pyrazine: Experimental and theoretical approaches
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The different rotameric conformations of imidazo-[1,2-a]pyrazine have been synthesized and characterized by means of different experimental techniques, such as NMR, FTIR, and absorption spectroscopy and quantum chemical calculations. The different conformations were stabilized by hydrogen bonds, such as OH?N, ArH?N and ArH?ArH. The ground state optimizations and potential energy surface (PES) scanning profiles produced using density functional theory (DFT) show two stable rotameric forms for each molecule. The relative population of the conformations is affected by the strength of the hydrogen bonds. The calculated absorption spectra and isotopic shielding constants were acquired by time-dependent density functional theory (TD-DFT) and gauge invariant atomic orbitals (GIAO)-DFT, respectively. The strength of the hydrogen bonding interactions that resulted in the different conformations was studied by quantum theory of atoms in molecules (QTAIM).
- Kumar, Gulshan,Goel, Richa,Paul, Kamaldeep,Luxami, Vijay
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p. 9707 - 9717
(2018/03/23)
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- Method for synthesizing 6,8-dibromo imidazo[1,2a] pyrazine
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The invention relates to a method for synthesizing 6,8-dibromo imidazo[1,2a] pyrazine. The method comprises the following steps: by taking 2-amino-3,5-dibromo pyrazine and chloroacetaldehyde as raw materials, in a proper solvent, performing reaction for 4-12 hours at 25-150 DEG C, and purifying, thereby obtaining a purified product, namely, 6,8-dibromo imidazo[1,2a] pyrazine. According to the method, reaction raw materials are easily available, the material price is reasonable, the reaction condition is gentle, the operation is easy, the control is easy, the aftertreatment is simple, the product quality is stable and the purity is high.
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Paragraph 0012; 0013; 0014; 0015; 0016; 0017; 0018-0022
(2017/08/29)
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- IMIDAZOPYRAZINE DERIVED COMPOUNDS FOR ELECTRONIC DEVICES
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The invention provides a composition comprising at least one compound of Formula 1 through Formula 8, each as described herein. These compounds, containing an imidazopyrazine moiety, are useful in organic electroluminescence devices.
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Paragraph 15; 16
(2017/01/09)
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- Synthesis, in vitro anticancer activity and SAR studies of arylated imidazo[1,2-a]pyrazine-coumarin hybrids
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A new series of imidazo[1,2-a]pyrazine-coumarin hybrids have been synthesized by the combination of two biologically active moieties, imidazo[1,2-a]pyrazine and coumarin, followed by the Suzuki-Miyaura cross coupling reaction for monoarylation at the C6 p
- Goel, Richa,Luxami, Vijay,Paul, Kamaldeep
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p. 37887 - 37895
(2015/05/20)
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- FUSED PYRAZINE DERIVATIVES HAVING INHIBITORY ACTIVITY ON TAK1
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A compound selected from pyrazine fused-ring derivatives of a chemical formula 1 or pharmaceutically acceptable salts thereof has excellent inhibition activity with respect to TAK1 kinase. A pharmaceutical composition comprising the same is capable of increasing activity of anticancer drugs with respect to cancer or tumor by inhibiting activation of TAK1 kinase, with excellent effects as a prevention agent or a therapeutic agent of cancer or tumor. In the chemical formula 1, A, X, Y, W, Z, E, R^1, and m are the same as defined in the specification.COPYRIGHT KIPO 2016
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Paragraph 0140-0143
(2016/11/02)
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- Structure-based drug design of RN486, a potent and selective Bruton's tyrosine kinase (BTK) inhibitor, for the treatment of rheumatoid arthritis
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Structure-based drug design was used to guide the optimization of a series of selective BTK inhibitors as potential treatments for Rheumatoid arthritis. Highlights include the introduction of a benzyl alcohol group and a fluorine substitution, each of which resulted in over 10-fold increase in activity. Concurrent optimization of drug-like properties led to compound 1 (RN486) (J. Pharmacol. Exp. Ther. 2012, 341, 90), which was selected for advanced preclinical characterization based on its favorable properties.
- Lou, Yan,Han, Xiaochun,Kuglstatter, Andreas,Kondru, Rama K.,Sweeney, Zachary K.,Soth, Michael,McIntosh, Joel,Litman, Renee,Suh, Judy,Kocer, Buelent,Davis, Dana,Park, Jaehyeon,Frauchiger, Sandra,Dewdney, Nolan,Zecic, Hasim,Taygerly, Joshua P.,Sarma, Keshab,Hong, Junbae,Hill, Ronald J.,Gabriel, Tobias,Goldstein, David M.,Owens, Timothy D.
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supporting information
p. 512 - 516
(2015/03/03)
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- N-SUBSTITUTED HETEROCYCLIC DERIVATIVES AS KINASE INHIBITORS
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The present invention provides N-substituted novel heterocyclic derivatives of formula (I) as protein kinase inhibitors, in which R1, R2 and 'n' have the same meanings given in the specification, and pharmaceutically acceptable salts
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Page/Page column 28; 29
(2014/09/03)
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- Palladium catalyzed novel monoarylation and symmetrical/unsymmetrical diarylation of imidazo[1,2-a]pyrazines and their in vitro anticancer activities
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Palladium catalyzed Suzuki-Miyaura cross-coupling reactions are reported for the synthesis of monoarylated (at the C8 position) and symmetrical diarylated (at the C6 and C8 positions) imidazo[1,2-a]pyrazines. Monoarylated products have also been used to s
- Goel, Richa,Luxami, Vijay,Paul, Kamaldeep
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p. 9885 - 9892
(2014/03/21)
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- COMBINATIONS FOR THE TREATMENT OF CANCER
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The present invention relates to combinations of at least two compounds A and B, compound A being an inhibitor of Mps-1 kinase, and compound B being an inhibitor of an anti-apoptotic protein of the Bcl-2 family. Another aspect of the present invention relates to the use of such combinations as described supra for the preparation of a medicament for the treatment or prophylaxis of a disease, particularly for the treatment of cancer. Another aspect of the present invention relates to the use of an anti- apoptotic protein from the Bcl-2 family as a sensitizer of cells to Mps-1 inhibitors. Another aspect of the present invention relates to the use of the ratio of pro-apoptotic and anti-apoptotic proteins from the Bcl-2 family in a biological sample as a biomarker for a Mps-1 kinase inhibitor treatment.
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Page/Page column 130-131
(2014/02/16)
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- 6-THIO-SUBSTITUTED IMIDAZOPYRAZINES FOR USE AS MPS-1 AND TKK INHIBITORS IN THE TREATMENT OF HYPERPROLIFERATIVE DISORDERS
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The present invention relates to substituted imidazopyrazine compounds of general formula (I): (I) in which R1, R2, R3, R4 and R5 are as defined in the claims, to methods of and intermediates for prep
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Paragraph 0267-0268
(2013/11/05)
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- SUBSTITUTED 6-IMIDAZOPYRAZINES FOR USE AS MPS-1 AND TKK INHIBITORS IN THE TREATMENT OF HYPERPROLIFERATIVE DISORDERS
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The present invention relates to substituted imidazopyrazine compounds of general formula (I), in which R1, R2, R3, R4 and R5 are as defined in the claims, to methods of and intermediates for preparin
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Paragraph 0242-0243
(2013/10/22)
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- SUBSTITUTED 6-IMIDAZOPYRAZINES FOR USE AS MPS-1 AND TKK INHIBITORS IN THE TREATMENT OF HYPERPROLIFERATIVE DISORDERS
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The present invention relates to substituted imidazopyrazine compounds of general formula (I), in which R1, R2, R3, R4 and R5 are as defined in the claims, to methods of and intermediates for preparin
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Page/Page column 44-45
(2012/06/30)
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- 6-SUBSTITUTED IMIDAZOPYRAZINES FOR USE AS MPS-1 AND TKK INHIBITORS IN THE TREATMENT OF HYPERPROLIFERATIVE DISORDERS
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The present invention relates to substituted imidazopyrazine compounds of general formula (I): in which R1, R2, R3, R4 and R5 are as defined in the claims, to methods of and intermediates for preparin
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Page/Page column 63
(2012/06/30)
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- 6-THIO-SUBSTITUTED IMIDAZOPYRAZINES FOR USE AS MPS-1 AND TKK INHIBITORS IN THE TREATMENT OF HYPERPROLIFERATIVE DISORDERS
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The present invention relates to substituted imidazopyrazine compounds of general formula (I) : (I) in which R1, R2, R3, R4 and R5 are as defined in the claims, to methods of and intermediates for pre
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Page/Page column 42
(2012/06/30)
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- IMIDAZOPYRAZINES FOR USE AS MPS-1 AND TKK INHIBITORS IN THE TREATMENT HYPERPROLIFERATIVE DISORDERS
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The present invention relates to substituted imidazopyrazine compounds of general formula (I) : in which R1, R2, R3, R4 and R5 are as defined in the claims, to methods of and intermediates for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of a hyper-proliferative and/or angiogenesis disorder, as a sole agent or in combination with other active ingredients.
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Page/Page column 44-45
(2012/06/30)
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- 6 SUBSTITUTED IMIDAZOPYRAZINES FOR USE AS MPS-1 AND TKK INHIBITORS IN THE TREATMENT OF HYPERPROLIFERATIVE DISORDERS
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The present invention relates to substituted imidazopyrazine compounds of general formula (I) in which R1, R2, R3, R4 and R5 are as defined in the claims, to methods of and intermediates for preparing
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Page/Page column 44
(2012/06/30)
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- FUSED IMIDAZOLE DERIVATIVE HAVING TTK INHIBITORY ACTION
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Provided are a compound represented by general formula (1) and having a TTK inhibitory action and a medicine containing the compound. In formula (1), (X, Y, V, W) is (—N═, ═CR1—, ═N—, —CR7═), (—CR2═, ═N—, ═N—, —CR7═), etc.; A is an (un)substituted aromatic hydrocarbon ring, etc.; L is a single bond, —C(═O)—NRA—, etc.; Z is a group represented by the formula —NR3R4 or a group represented by the formula —OR5; R1 to R3, R6, and R7 each is a hydrogen atom, etc.; R4 and R5 each is an (un)substituted alkyl, etc.; and R8 is an (un)substituted cycloalkyl, etc.
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Page/Page column 53-54
(2012/03/26)
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- Discovery of novel imidazo[1,2-a]pyrazin-8-amines as Brk/PTK6 inhibitors
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A series of substituted imidazo[1,2-a]pyrazin-8-amines were discovered as novel breast tumor kinase (Brk)/protein tyrosine kinase 6 (PTK6) inhibitors. Tool compounds with low-nanomolar Brk inhibition activity, high selectivity towards other kinases and desirable DMPK properties were achieved to enable the exploration of Brk as an oncology target.
- Zeng, Hongbo,Belanger, David B.,Curran, Patrick J.,Shipps Jr., Gerald W.,Miao, Hua,Bracken, Jack B.,Arshad Siddiqui,Malkowski, Michael,Wang, Yan
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scheme or table
p. 5870 - 5875
(2011/10/09)
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- IMIDAZOPYRAZINE SYK INHIBITORS
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Certain imidazopyrazines and pharmaceutical compositions thereof are provided herein. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of Syk activity, which comprises administering to such patients an amount of at least one chemical entity effective to reduce signs or symptoms of the disease or disorder are provided. Also provided are methods for determining the presence or absence of Syk kinase in a sample.
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Page/Page column 12-13
(2010/06/22)
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- Structure-based design of imidazo[1,2-a]pyrazine derivatives as selective inhibitors of Aurora-A kinase in cells
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Co-crystallisation of the imidazo[1,2-a]pyrazine derivative 15 (3-chloro-N-(4-morpholinophenyl)-6-(pyridin-3-yl)imidazo[1,2-a]pyrazin-8-amine) with Aurora-A provided an insight into the interactions of this class of compound with Aurora kinases. This led to the design and synthesis of potent Aurora-A inhibitors demonstrating up to 70-fold selectivity in cell-based Aurora kinase pharmacodynamic biomarker assays.
- Bouloc, Nathalie,Large, Jonathan M.,Kosmopoulou, Magda,Sun, Chongbo,Faisal, Amir,Matteucci, Mizio,Reynisson, Jóhannes,Brown, Nathan,Atrash, Butrus,Blagg, Julian,McDonald, Edward,Linardopoulos, Spiros,Bayliss, Richard,Bavetsias, Vassilios
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scheme or table
p. 5988 - 5993
(2010/11/02)
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- IMIDAZOPYRAZINE SYK INHIBITORS
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Certain imidazopyrazines and pharmaceutical compositions thereof are provided herein. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of Syk activity, which comprises administering to such patients an amount of at least one chemical entity effective to reduce signs or symptoms of the disease or disorder are provided. Also provided are methods for determining the presence or absence of Syk kinase in a sample
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(2010/07/02)
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- Discovery of imidazo[1,2-a]pyrazine-based Aurora kinase inhibitors
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The synthesis and structure-activity relationships (SAR) of novel, potent imidazo[1,2-a]pyrazine-based Aurora kinase inhibitors are described. The X-ray crystal structure of imidazo[1,2-a]pyrazine Aurora inhibitor 1j is disclosed. Compound 10i was identified as lead compound with a promising overall profile.
- Belanger, David B.,Curran, Patrick J.,Hruza, Alan,Voigt, Johannes,Meng, Zhaoyang,Mandal, Amit K.,Siddiqui, M. Arshad,Basso, Andrea D.,Gray, Kimberly
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scheme or table
p. 5170 - 5174
(2010/10/02)
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- Imidazo[1,2-a]pyrazine diaryl ureas: Inhibitors of the receptor tyrosine kinase EphB4
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Inhibition of receptor tyrosine kinases (RTKs) such as vascular endothelial growth factor receptors (VEGFRs) and platelet-derived growth factor receptors (PDGFRs) has been validated by recently launched small molecules Sutent and Nexavar/
- Mitchell, Scott A.,Danca, Mihaela Diana,Blomgren, Peter A.,Darrow, James W.,Currie, Kevin S.,Kropf, Jeffrey E.,Lee, Seung H.,Gallion, Steven L.,Xiong, Jin-Ming,Pippin, Douglas A.,DeSimone, Robert W.,Brittelli, David R.,Eustice, David C.,Bourret, Aaron,Hill-Drzewi, Melissa,Maciejewski, Patricia M.,Elkin, Lisa L.
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experimental part
p. 6991 - 6995
(2010/07/15)
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- PYRIDINONYL PDK1 INHIBITORS
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The present invention provides pyridinonyl PDKl inhibitors and methods of treating cancer using the same.
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Page/Page column 184
(2008/06/13)
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- IMIDAZO[1,2-A]PYRAZIN-8-YLAMINES AND METHOD OF INHIBITION OF BRUTON’S TYROSINE KINASE BY SUCH COMPOUNDS
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Compounds of Formula (I-a) and all pharmaceutically-acceptable forms thereof, are described herein. The variables R1, R2, R3, Z1, Q, and A shown in Formula I-a are defined herein. Pharmaceutical compositions con
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Page/Page column 44-45
(2010/02/10)
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- IMIDAZO ‘1,2-A’ PYRAZINE COMPOUNDS WHICH INTERACT WITH PROTEIN KINASES
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The present invention relates to a novel compounds of formula I, to pharmaceutical compounds, to processes for their preparation, as well as to the use of the compounds in the inhibition of protein kinases, in particular serine/threonine kinases, more par
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Page/Page column 37-38; 40-41
(2008/06/13)
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- Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhbitors
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The present invention relates to 8-amino-aryl-substituted imidazopyrazines which modulate the activity of protein kinases (“PKs”). The compounds of this invention are therefore useful in treating disorders related to abnormal PK activity. Pharmaceutical compositions comprising these compounds, methods of treating diseases utilizing pharmaceutical compositions comprising these compounds and methods of preparing them are also disclosed.
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- Novel imidazopyrazines as cyclin dependent kinase inhibitors
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In its many embodiments, the present invention provides a novel class of imidazo[1,2-a]pyrazine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, me
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Page/Page column 27
(2008/06/13)
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- CERTAIN 8-HETEROARYL-6-PHENYL-IMIDAZO[1,2-A]PYRAZINES AS MODULATORS OF HSP90 COMPLEX ACTIVITY
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This invention pertains to compounds of Formula (I) and the pharmaceutically-acceptable forms thereof. The variables R1, R2, R3, Z1, Z2, W, and X shown in Formula I are defined herein. The invention a
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- THIOPENE-BASED TRICYCLIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME
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Compounds having the formula (I), and pharmaceutically-acceptable salts, hydrates and prodrugs thereof, are useful as anti-inflammatory agents, in which R1, R2, and R3 are hydrogen, halogen, alkyl, or perfluoroalkyl; R4 is an optionally substituted alkyl or cycloalkyl group; X is a linker; A is an aryl, heteroaryl, heterocycle, cycloalkyl, or is absent; and R7 is a substituent on A as defined in the specification.
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Page/Page column 131-132
(2010/02/07)
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- Imidazo[1,2-a]pyrazin-8-ylamines, method of making, and method of use thereof
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A novel composition comprises a compound of Formula 1 the pharmaceutically acceptable salts, hydrates, solvates, crystal forms, diastereomers, prodrugs, or mixtures thereof. The composition is of particular utility in the treatment of kinase-implicated disorders.
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- 8-alkylaminoimidazo(1,2-a)pyrazines and derivatives, their preparation and their application in therapy
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STR1 Novel 8-alkylamino-imidazo(1,2-a)pyrazines of formula (I) show advantages pharmacological activities. They can be used for medical products in human and veterinary therapy in the field of applications of antispasmodics, uterine relaxants, bronchodila
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- Synthesis of imidazo[1,2-a]pyrazine derivatives with uterine-relaxing, antibronchospastic, and cardiac-stimulating properties
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A series of imidazo[1,2-a]pyrazine derivatives was synthesized by condensation of α-halogenocarbonyl compounds and aminopyrazines. Various compounds resulted from competitive reactions or reagent isomerization and demonstrated in vitro uterine-relaxing and in vivo antibronchospastic activities. On isolated atria, 5-bromoimidazo[1,2-a]pyrazine showed positive chronotropic and inotropic properties; the latter was associated with an increase in the cyclic AMP tissue concentration. Potentiation of the isoproterenol positive inotropic effect of 5-bromoimidazo[1,2-a]pyrazine and the lack of blockade of the 5-bromoimidazo[1,2-a]pyrazine positive inotropic effect by propranolol suggested phosphodiesterase-inhibiting properties.
- Sablayrolles,Cros,Milhavet,Rechenq,Chapat,Boucard,Serrano,McNeill
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p. 206 - 212
(2007/10/02)
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