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Pyridine-3-carboxyamide derivative
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A formamide and derivative technology, applied in the field of pyridine-3-carboxamide derivatives
Active Publication Date: 2011-10-26
KOWA CO LTD
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Also, there are no reports on pyridine-based JAK3 inhibitors, so it is still strongly desired to develop pyridine derivatives with excellent JAK3 inhibitory activity
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Embodiment 1
[0485] Example 1 Preparation of 4-(benzylamino)-6-chloropyridine-3-carboxamide
[0486]
[0487] Dissolve 5.00 g of 4,6-dichloropyridine-3-carboxamide synthesized according to the method described in US2006 / 0217417 in 50 mL of ethanol, add 3.37 g of benzylamine and 4.40 g of N,N-diisopropylethylamine , heated to reflux for 12 hours. After cooling, the solvent was distilled off, and 100 mL of water was added to the residue. After cooling with ice water, the precipitated crystals were collected by filtration, washed with water and hexane, and air-dried. Furthermore, drying under reduced pressure (100° C., 2 hours) obtained 5.96 g (87%) of the title compound as light yellow needle crystals.
[0489] Example 2 Preparation of 6-chloro-4-[(2-methoxybenzyl)amino]pyridine-3-carboxamide
[0490]
[0491] The title compound was obtained as a colorless crystalline powder from 4,6-dichloropyridine-3-carboxamide and 2-methoxybenzylamine in the same manner as in Example 1 (yield 71%).
[0493] Example 3 Preparation of 6-chloro-4-[(3-methoxybenzyl)amino]pyridine-3-carboxamide
[0494]
[0495] In the same manner as in Example 1, the title compound was obtained as a colorless crystalline powder from 4,6-dichloropyridine-3-carboxamide and 3-methoxybenzylamine (yield 99%).
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technical field [0001] The present invention relates to novel compounds for Janus tyrosinase 3 (JAK3) inhibitors, their preparation methods, pharmaceutical compositions containing these novel compounds or pharmaceutically acceptable salts thereof and applications thereof. Background technique [0002] Proteinkinase JAK (Janus Kinase) is a proteintyrosinephosphatase present in the cytoplasm capable of controlling functions related to proliferation and survival of cells of the lympho-hematopoietic system. JAKs are activated by mediating stimulation of cytokine receptors, inducing phosphorylation of tyrosine residues of STAT (signaltransducer and activator of transcription) proteins. Phosphorylated STATs form dimers, translocate from the cytoplasm to the nucleus, and bind to specific DNA sequences to cause transcriptional activation of genes (Gene, 285, 1-24, 2002). [0003] There are four known members of the JAK family, JAK1, JAK2, JAK3 and TYK2. JAK1, JAK2, and TYK2 ar...
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