- NOVEL 4,6-DISUBSTITUTED AMINOPYRIMIDINE DERIVATIVES HAVING BOTH AROMATIC AND HALOGENIC SUBSTITUENTS
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Certain 4,6-disubstituted aminopyrimidine derivatives having both aromatic and halogenic substituents.
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Paragraph 0583; 0584
(2014/03/24)
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- Exploratory process development and kilogram-scale synthesis of a novel oxazolidinone antibacterial candidate
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A concise, environmentally benign, and cost-effective route was developed for the large-scale preparation of 1, a novel oxazolidinone antibacterial candidate. The key intermediate 2-(1-(2-fluoro-4-nitrophenyl)-1H-pyrazol-4-yl) pyridine 7 was prepared with high purity by mild deamination of the regioisomeric mixture 21. The mixture was prepared from a nucleophilic SNAr reaction by selective C-N coupling of the secondary amine functionality of 4-(pyridin-2-yl)-1H-pyrazol-3-amine 14 with 1,2-difluoro-4-nitrobenzene 10 in optimized conditions with the primary amine group remaining intact. The gaseous nitrogen release rate and reaction mixture temperature of the deamination step can be well controlled by altering the feeding manner, thereby providing safety guarantees. The optimized synthetic strategy of 1 with an overall yield of 27.6%, including seven sequential transformations by only five solid-liquid isolations, significantly improved the product separation workup. The strategy bypassed time-consuming and laborious procedures for any intermediate involved as well as for the final API. This study presents a process enabling the rapid delivery of a multikilogram quantity of API with high purity.
- Yang, Tao,Chen, Jia-Xiang,Fu, Yiwei,Chen, Kaixiao,He, Jinyun,Ye, Weiwei,Sang, Zitai,Luo, Youfu
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p. 511 - 519
(2014/05/06)
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- NOVEL COMPOUNDS AS MODULATORS OF PROTEIN KINASES
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The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.
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Page/Page column 114; 115
(2012/11/14)
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- NOVEL COMPOUNDS AS MODULATORS OF PROTEIN KINASES
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The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.
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Page/Page column 106
(2012/12/13)
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- BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
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The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional hetercyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.
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Page/Page column 249
(2010/02/06)
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- THE PHOTOREACTIONS OF 2-FLUORO-4-NITROANISOLE WITH AMINES. THE SEARCH FOR NEW BIOCHEMICAL PHOTOPROBES
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The photosubstitutions of 2-fluoro-4-nitroanisole with several amines are studied from the preparative and the preliminary mechanistic points of view.The possible usefulness of this structure as biochemical photoprobe is discussed.
- Figueredo, M.,Marquet, J.,Moreno-Manas, M.,Pleixats, R.
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p. 2427 - 2428
(2007/10/02)
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