- From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase
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Significant inhibition of Aurora B was achieved by the synthesis of simplified fragments of benzosceptrins and oroidin belonging to the marine pyrrole-2-aminoimidazoles metabolites isolated from sponges. Evaluation of kinase inhibition enabled the discovery of a synthetically accessible rigid acetylenic structural analogue EL-228 (1), whose structure could be optimized into the potent CJ2-150 (37). Here we present the synthesis of new inhibitors of Aurora B kinase, which is an important target for cancer therapy through mitosis regulation. The biologically oriented synthesis yielded several nanomolar inhibitors. The optimized compound CJ2-150 (37) showed a non-ATP competitive allosteric mode of action in a mixed-type inhibition for Aurora B kinase. Molecular docking identified a probable binding mode in the allosteric site "F"and highlighted the key interactions with the protein. We describe the improvement of the inhibitory potency and specificity of the novel scaffold as well as the characterization of the mechanism of action.
- Juillet, Charlotte,Ermolenko, Ludmila,Boyarskaya, Dina,Baratte, Blandine,Josselin, Béatrice,Nedev, Hristo,Bach, Stéphane,Iorga, Bogdan I.,Bignon, Jér?me,Ruchaud, Sandrine,Al-Mourabit, Ali
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p. 1197 - 1219
(2021/02/05)
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- Discovery of imidazo[1,2-a]pyridine-thiophene derivatives as FLT3 and FLT3 mutants inhibitors for acute myeloid leukemia through structure-based optimization of an NEK2 inhibitor
-
FMS-like tyrosine kinase 3 (FLT3) with an internal tandem duplication (ITD) mutation has been validated as a driver lesion and a therapeutic target for acute myeloid leukemia (AML). Currently, several potent small-molecule FLT3 kinase inhibitors are being evaluated or have completed evaluation in clinical trials. However, many of these inhibitors are challenged by the secondary mutations on kinase domain, especially the point mutations at the activation loop (D835) and gatekeeper residue (F691). To overcome the resistance challenge, we identified a novel series of imidazo[1,2-a]pyridine-thiophene derivatives from a NIMA-related kinase 2 (NEK2) kinase inhibitor CMP3a, which retained inhibitory activities on FTL3-ITDD835V and FLT3-ITDF691L. Through this study, we identified the imidazo[1,2-a]pyridine-thiophene derivatives as type-I inhibitors of FLT3. Moreover, we observed compound 5o as an inhibitor displaying equal anti-proliferative activities against FLT3-ITD, FTL3-ITDD835Y and FLT3-ITDF691L driven acute myeloid leukemia (AML) cell lines. Meanwhile, the apoptotic effects of compound supported its mechanism of anti-proliferative action. These results indicate that the imidazo[1,2-a]pyridine-thiophene scaffold is promising for targeting acquired resistance caused by FLT3 secondary mutations and compound 5o is an interesting lead in this direction.
- Zhang, Lingtian,Lakkaniga, Naga Rajiv,Bharate, Jaideep B.,Mcconnell, Nicholas,Wang, Xiuqi,Kharbanda, Anupreet,Leung, Yuet-Kin,Frett, Brendan,Shah, Neil P.,Li, Hong-yu
-
-
- Design, synthesis and biological evaluation of imidazopyridazine derivatives containing isoquinoline group as potent MNK1/2 inhibitors
-
Mitogen-activated protein kinase (MAPK)-interacting kinases (MNKs) are located at the meeting-point of ERK and p38 MAPK signaling pathways, which can phosphorylate eukaryotic translation initiation factor 4E (eIF4E) at the conserved serine 209 exclusively. MNKs modulate the translation of mRNA involved in tumor-associated signaling pathways. Consequently, selective inhibitors of MNK1/2 could reduce the level of phosphorylated eIF4E. Series of imidazopyrazines, imidazopyridazines and imidazopyridines derivatives were synthesized and evaluated as MNK1/2 inhibitors. Several compounds exhibited great inhibitory activity against MNK1/2 and selected compounds showed moderate to excellent anti-proliferative potency against diffuse large B-cell lymphoma (DLBCL) cell lines. In particular, compound II-5 (MNK1 IC50 = 2.3 nM; MNK2 IC50 = 3.4 nM) exhibited excellent enzymatic inhibitory potency and proved to be the most potent compound against TMD-8 and DOHH-2 cell lines with IC50 value of 0.3896 μM and 0.4092 μM respectively. These results demonstrated that compound II-5 could be considered as a potential MNK1/2 inhibitor for further investigation.
- Bu, Hong,Yuan, Xinrui,Wu, Hanshu,Zhou, Jinpei,Zhang, Huibin
-
-
- INHIBITORS OF LIN28 AND METHODS OF USE THEREOF
-
The present disclosure relates to compounds of formula (I) and compositions comprising the same. The disclosure further relates to methods of treating cancers.
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Page/Page column 52; 69; 102-103
(2021/06/26)
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- Imidazopyridine MNK1/MNK2 kinase inhibitor, and preparation method and application thereof
-
The invention provides an imidazopyridine MNK1/MNK2 kinase inhibitor, and a preparation method and application thereof. The invention particularly provides a compound as shown in a formula (I) which is described in the specification, or a stereoisomer, a tautomer or a pharmaceutically acceptable salt thereof. The compound provided by the invention can be used for preparing a pharmaceutical composition for treating diseases or symptoms related to MNK activity or expression quantity.
- -
-
Paragraph 0089-0095
(2020/12/09)
-
- Design, Synthesis, and Biological Evaluation of Imidazo[1,2- a]pyridine Derivatives as Novel PI3K/mTOR Dual Inhibitors
-
PI3K-Akt-mTOR signaling pathway has been validated as an effective targeting pathway for cancer therapy. However, no PI3K/mTOR dual inhibitor has been approved by the FDA yet. Therefore, it is still essential to discover a candidate with good efficacy and low toxicity. In our design, a series of imidazo[1,2-a]pyridine derivatives had been synthesized and subjected to activity assessment in vitro and in vivo. 15a was proved to be a potent PI3K/mTOR dual inhibitor with excellent kinase selectivity, modest plasma clearance, and acceptable oral bioavailability. Besides, 15a displayed significant inhibition of tumor growth in HCT116 and HT-29 xenografts without obvious effect on body weight.
- Yu, Ya'Nan,Han, Yuqiao,Zhang, Fupo,Gao, Zhenmei,Zhu, Tong,Dong, Suzhen,Ma, Mingliang
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p. 3028 - 3046
(2020/04/09)
-
- Imidazopyridine MNK1/MNK2 kinase inhibitor as well as preparation method and application thereof
-
The invention provides an imidazopyridine MNK1/MNK2 kinase inhibitor as well as a preparation method and application thereof, and particularly provides a compound as shown in a formula (I), or a stereoisomer, a tautomer or a pharmaceutically acceptable salt thereof. The compound provided by the invention can be used for preparing a pharmaceutical composition for treating diseases or symptoms related to MNK activity or expression quantity.
- -
-
Paragraph 0088-0091
(2020/12/09)
-
- Imidazo [1, 2 - a] pyridine derivatives and preparation method and application thereof (by machine translation)
-
The invention discloses 3 -phenyl imidazo [1, 2 - a] pyridine derivatives represented by a formula (I) or 3 - (thiophene -2 substituted) imidazo [1, 2 - a] pyridine derivatives and a preparation method, and also discloses application. of the 3 -phenyimidazo [1, 2 - a] pyridine derivatives or 3 - (thiophene -2 substituted) imidazo [1, 2 - a] pyridine derivatives as a class of novel structural novel small molecule inhibitors, and the like. (by machine translation)
- -
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Paragraph 0154-0158
(2019/07/29)
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- Aromatic heterocyclic compound serving as PI3K/mTOR kinase regulator and preparation method and application of aromatic heterocyclic compound
-
The invention discloses 6-(6-substituted group-5-sulfonamido-3-pyridinyl)imidazo[1,2-a]pyridines shown as a formula (I) or 6-(6-substituted group-5-sulfonamido-3-pyridinyl)imidazo[1,2-b]pyridazine derivatives or pharmaceutically acceptable salts thereof and a preparation method. The invention also discloses application of 6-(6-substituted group-5-sulfonamido-3-pyridinyl)imidazo[1,2-a]pyridines or6-(6-substituted group-5-sulfonamido-3-pyridinyl)imidazo[1,2-b]pyridazine derivatives or pharmaceutically acceptable salts thereof to preparation of medicines for resisting tumors, treating cerebral ischemia and treating diabetes mellitus as a PI3K/mTOR inhibitor.
- -
-
Paragraph 0137; 0228
(2019/08/12)
-
- Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof
-
The present invention provides for a method for treating a disease condition associated with PI3-kinase α and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase α and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth.
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Page/Page column 343
(2016/04/26)
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- PURINE INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
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Provided are compounds of formula I which are PI3K-delta inhibitors, and as such are useful for the treatment of PI3K-delta-mediated diseases such as inflammation, asthma, COPD and cancer.
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Page/Page column 88
(2016/01/01)
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- HETEROCYCLIC COMPOUNDS AND USES THEREOF
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Heterocyclic entities that modulate PI3 kinase activity, pharmaceutical compositions containing the heterocyclic entities, and methods of using these chemical entities for treating diseases and conditions associated with PI3 kinase activity are described herein.
- -
-
Paragraph 0553; 0554
(2015/11/30)
-
- COMBINATION OF KINASE INHIBITORS AND USES THEREOF
-
The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or a receptor tyrosine kinase (RTK) in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase α and/or an RTK in a subject. In yet another aspect, a method of inhibiting phosphorylation of Akt (S473) in a cell is set forth.
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Page/Page column 66
(2015/02/19)
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- 2-ACYLAMIDOMETHYL AND SULFONYLAMIDOMETHYL BENZOXAZINE CARBAMATES FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE
-
The invention provides certain benzoxazine compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, Ra, Rb, Rc, Rd, Rg, and Cy are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds of the Formula (I) or pharmaceutically acceptable salts thereof, and methods of using the compounds of the Formula (I) or pharmaceutically acceptable salts thereof or pharmaceutical compositions comprising the same for treating diseases or conditions mediated by RORgammaT.
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-
Paragraph 0250
(2015/07/07)
-
- A novel pyrazolopyridine with in vivo activity in Plasmodium berghei- and Plasmodium falciparum-infected mouse models from structure-activity relationship studies around the core of recently identified antimalarial imidazopyridazines
-
Toward improving pharmacokinetics, in vivo efficacy, and selectivity over hERG, structure-activity relationship studies around the central core of antimalarial imidazopyridazines were conducted. This study led to the identification of potent pyrazolopyridines, which showed good in vivo efficacy and pharmacokinetics profiles. The lead compounds also proved to be very potent in the parasite liver and gametocyte stages, which makes them of high interest.
- Le Manach, Claire,Paquet, Tanya,Brunschwig, Christel,Njoroge, Mathew,Han, Ze,Gonzàlez Cabrera, Diego,Bashyam, Sridevi,Dhinakaran, Rajkumar,Taylor, Dale,Reader, Janette,Botha, Mariette,Churchyard, Alisje,Lauterbach, Sonja,Coetzer, Theresa L.,Birkholtz, Lyn-Marie,Meister, Stephan,Winzeler, Elizabeth A.,Waterson, David,Witty, Michael J.,Wittlin, Sergio,Jiménez-Díaz, María-Belén,Santos Martínez, María,Ferrer, Santiago,Angulo-Barturen, I?igo,Street, Leslie J.,Chibale, Kelly
-
supporting information
p. 8713 - 8722
(2015/11/25)
-
- IMIDAZOPYRIDINE COMPOUNDS AND USES THEREOF
-
The invention provides compounds of formula (1), stereoisomers and tautomers thereof, or pharmaceutically acceptable salts, solvates and polymorphs thereof, and processes for their preparation. The invention further relates to pharmaceutical compositions containing said compounds and their use in the treatment of diseases or disorders mediated by one or more proinflammatory cytokines selected from TNF-a, IL-Ιβ, IL-6, IL-8, IL-12, IL-17 or IL-23.
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Page/Page column 33
(2014/06/11)
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- HETEROAROMATIC COMPOUNDS AS PI3 KINASE MODULATORS AND METHODS OF USE
-
The present invention provides heteroaromatic derivatives and pharmaceutical acceptable salts and formulations thereof useful in modulating the protein kinase activity, especially phosphatidylinositol 3-kinases (PI3 kinases) and mTOR, and in modulating inter- and/or intra-cellular signaling activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.
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Paragraph 0399
(2014/05/20)
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- COMBINATION OF KINASE INHIBITORS AND USES THEREOF
-
The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth. The present invention also provides a pharmaceutical kit effective for treating a disease condition associated with PI3 -kinase α and/or mTOR in a subject.
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Paragraph 00641
(2014/10/04)
-
- HETEROCYCLIC COMPOUNDS AND USES THEREOF
-
Heterocyclic entities that modulate PI3 kinase activity, pharmaceutical compositions containing the heterocyclic entities, and methods of using these chemical entities for treating diseases and conditions associated with PI3 kinase activity are described herein.
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Page/Page column 118
(2012/09/11)
-
- OXAZOLIDINONE DERIVATIVE HAVING FUSED RING
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The present invention provides a novel antimicrobial drug comprising an oxazolidinone derivative of the formula (I): or a pharmaceutically acceptable salt or solvate thereof; wherein ring A is ring B is a benzene ring optionally substituted with lower alkyl; ring C is an optionally substituted six-membered heterocycle containing at least one nitrogen atom and one to three double bond(s) in the ling wherein the atom at the point of attachment to ring B is a carbon atom; ring D is an optionally substituted five-membered ring containing one or two double bond(s) in the ring; A1 and A2 are independently nitrogen or carbon; m is 0 or 1; R represents H, —NHC(═O)RA, —NHC(═S)RA, —NH-het1, —O-het1, —S-het1, —S(═O)-het1, —S(═O)2-het1, het2, —CONHRA, —OH, lower alkyl, lower alkoxy or lower alkenyl; and het1 and het2 are independently a heterocyclic group; with the proviso that the fused ring C-D is not
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Page/Page column 56
(2011/05/05)
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- Design and synthesis of imidazopyridine analogues as inhibitors of phosphoinositide 3-kinase signaling and angiogenesis
-
Phosphatidylinositol 3-kinase α (PI3Kα) is an important regulator of intracellular signaling pathways, controlling remarkably diverse arrays of physiological processes. Because the PI3K pathway is frequently up-regulated in human cancers, the inhibition of PI3Kα can be a promising approach to cancer therapy. In this study, we have designed and synthesized a new series of imidazo[1,2-a]pyridine derivatives as PI3Kα inhibitors through the fragment-growing strategy. By varying groups at the 3- and 6-positions of imidazo[1,2-a]pyridines, we studied the structure-activity relationships (SAR) profiles and identified a series of potent PI3Kα inhibitors. Representative derivatives showed good activity in cellular proliferation and apoptosis assays. Moreover, these inhibitors exhibited noteworthy antiangiogenic activity.
- Kim, Okseon,Jeong, Yujeong,Lee, Hyunseung,Hong, Sun-Sun,Hong, Sungwoo
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experimental part
p. 2455 - 2466
(2011/06/20)
-
- Pd-catalyzed regiocontrolled Sonogashira and Suzuki cross-coupling reaction of 3,6-dihalogenoimidazo[1,2-a]pyridines: One-pot double-coupling approach
-
New and efficient regioselective Sonogashira and Suzuki-Miyaura palladium-catalyzed coupling reactions of 3,6-dihalogenoimidazo[1,2-a]pyridines followed by another cross-coupling has been successfully developed. Various solvents, palladium species and bases were tested. Scope and limitations of this regiocontrolled palladium-catalyzed reaction were investigated. The synthesis of 3,6-disubstituted imidazo[1,2-a]pyridine derivatives using one-pot regioselective double-coupling approach was developed. This procedure affords convergent syntheses of polysubstituted compounds in high yields in a very few steps.
- El Akkaoui, Ahmed,Bassoude, Ibtissam,Koubachi, Jamal,Berteina-Raboin, Sabine,Mouaddib, Abderrahim,Guillaumet, Gerald
-
experimental part
p. 7128 - 7138
(2011/10/05)
-
- INHIBITORS OF PI3 KINASE
-
The present invention relates to compounds of Formula I, II or III or a pharmaceutically acceptable salt thereof; methods of treating diseases or conditions, such as cancer, using the compounds; and pharmaceutical compositions containing the compounds, wherein the variables are as defined herein
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Page/Page column 53
(2010/10/03)
-
- ORGANIC COMPOUNDS
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Compounds of formula (I): in free or salt or solvate form, where R1, R2, R3 and R20 have the meanings as indicated in the specification, are useful for treati ng diseases mediated by the ALK-5 and/or ALK-4 receptor. Pharmaceutical composit ions that contain the compounds and processes for preparing the compounds are also described.
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Page/Page column 119
(2009/05/28)
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- COMPOUNDS AND COMPOSITIONS AS KINASE INHIBITORS
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The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with abnormal or deregulated kinase activity, particularly Ros, KDR, FMS, c-FMS, FLT3, c-Kit, JAK2, JAK3, Aurora, PDGFR, Lck, TrkA, TrkB, TrkC, IGF-1R, ALK4, ALK5 and ALK or combinations thereof.
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Page/Page column 154
(2009/12/23)
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- THIOZOLIDINEDIONE DERIVATIVES AS P13 KINASE INHIBITORS
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Invented is a method of inhibiting the activity/function of PB kinases using thiozolidinedione derivatives. Also invented is a method of treating one or more disease states selected from: autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergy, asthma, pancreatitis, multiorgan failure, kidney diseases, platelet aggregation, cancer, sperm motility, transplantation rejection, graft rejection and lung injuries by the administration of thiozolidinedione derivatives.
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Page/Page column 44-45
(2008/06/13)
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- NOVEL JNK INHIBITORS
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Disclosed are compounds of the formula (I) wherein X is N or CH, and Y is N or CR5. Also disclosed are methods of treating JNK and ERK mediated diseases using the compounds of formula 1.0.
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Page/Page column 104
(2008/12/07)
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- Synthesis of polysubstituted imidazo[1,2-a]pyridines via microwave-assisted one-pot cyclization/Suzuki coupling/palladium-catalyzed heteroarylation
-
(Chemical Equation Presented) A new and efficient method for the synthesis of 2,3,6-trisubstituted imidazo[1,2-a]pyridine derivatives using a microwave-assisted one-pot, two-step Suzuki/heteroarylation or one-pot, three-step cyclization/Suzuki/heteroarylation was developed. Polysubstituted compounds are obtained in good yield from 2-amino-5-halogenopyridines, 2-halogenocarbonyl derivatives, boronic acids, and heteroaryl bromides.
- Koubachi, Jamal,El Kazzouli, Said,Berteina-Raboin, Sabine,Mouaddib, Abderrahim,Guillaume, Gerald
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p. 7650 - 7655
(2008/02/12)
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- NOVEL COMPOUNDS AS PHARMACEUTICAL AGENTS
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The current invention relates to compounds of the formula:(Ia) and the pharmaceutically acceptable salts thereof and their use as TGF-beta signal transduction inhibitors for treating cancer and other diseases in a patient in need thereof by administration of said compounds.
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- Imidazo[1,2-a]pyridines. Part 2: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors
-
Exploration of SAR and optimisation of the imidazo[1,2-a]pyridine CDK inhibitors has lead to the discovery of novel, potent and selective inhibitors of the cyclin-dependent kinase CDK2. Understanding of SAR has identified positions of substitution, which allow modification of physical properties and offer the potential for in vivo optimisation.
- Byth, Kate F.,Culshaw, Janet D.,Green, Stephen,Oakes, Sandra E.,Thomas, Andrew P.
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p. 2245 - 2248
(2007/10/03)
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- Imidazo[1,2-a]pyridines. Synthesis and inotropic activity of new 5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinone derivatives
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A series of 1,2-dihydro-5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinones was synthesized and evaluated for positive inotropic activity. 1,2-Dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2-oxo-3- pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1,2-a]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increase in the i.v. cardiotonic potency (ED50) from 52 to 23 μg/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1,2-dihydro-5-(6-fluoroimidazo[1,2-a]pyridin-2-yl)-6-methyl-2(1H)- pyridinone (3a) was the most potent (i.v. ED50 11 μg/kg) in this seris. E-1020 is presently under development for the treatment of congestive heart failure.
- Yamanaka,Miyake,Suda,Ohhara,Ogawa
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p. 1556 - 1567
(2007/10/02)
-
- Certain 6-substituted-2-pyridinamines
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Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
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-
- Substituted imidazo [1,2-a] pyridines
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Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
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-
-
- Certain substituted imidazo [1,2-a] pyridines
-
Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
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- Imidazo [1,2-a] pyridines substituted with a thienyl, thiazolyl, or thiadiazolyl group
-
Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3- position and a heterocyclic moiety on the pyrido portion of the molecule are active anthelmintic agents. The heterocyclic moiety is connected to the imidazo [1,2-a] pyridine molecule through an oxygen, sulfur, sulfinyl or sulfone. The novel compounds are prepared from the appropriately substituted 2-amino pyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
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