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Pyridine-3-carboxyamide derivative

A formamide and derivative technology, applied in the field of pyridine-3-carboxamide derivatives

Active Publication Date: 2014-03-26
KOWA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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Examples

Experimental program
Comparison scheme
Effect test

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.

[0488] 1 H-NMR (400MHz, CDCl 3 )δ: 4.42 (2H, d, J=5.6Hz), 5.82 (2H, br), 6.53 (1H, s), 7.26-7.39 (5H, m), 8.28 (1H, s), 8.90 (1H, br )

Embodiment 2

[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%).

[0492] 1 H-NMR (400MHz, CDCl 3 )δ: 3.89 (3H, s), 4.40 (2H, d, J=6.1Hz), 5.77 (2H, br), 6.60 (1H, s), 6.89-6.95 (2H, m), 7.21 (1H, dd , J=8.8, 1.5Hz), 7.29(1H, dd, J=7.6, 1.9Hz), 8.25(1H, s), 8.86(1H, br)

Embodiment 3

[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%).

[0496] 1 H-NMR (400MHz, CDCl 3 )δ: 3.80 (3H, s), 4.39 (2H, d, J=5.6Hz), 5.78 (2H, br), 6.52 (1H, s), 6.82-6.85 (2H, m), 6.88-6.91 (1H , m), 7.27-7.30 (1H, m), 8.28 (1H, s), 8.90 (1H, br)

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Abstract

To provide a novel JAK3 inhibitor that is useful as a preventive and / or therapeutic agent for rejection and graft versus host disease (GvHD) in organ transplantation, rheumatoid arthritis, multiple sclerosis, systemic lupus erythematosus, Sjögren syndrome, Behcet's disease, type I diabetes mellitus, autoimmune thyroiditis, idiopathic thrombocytopenic purpura, ulcerative colitis, Crohn's disease, asthma, allergic rhinitis, atopic dermatitis, contact dermatitis, urticaria, eczema, psoriasis, allergic conjunctivitis, uveitis, cancer, leukemia and the like. The pyridine-3-carboxyamide derivative represented by the general formula (1): or its salt or a solvate thereof.

Description

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] Protein kinase JAK (Janus Kinase) is a protein tyrosine phosphatase 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 (signal transducer 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/82A61K31/44A61K31/4439A61K31/4545A61K31/496A61K31/506A61K31/5377A61K31/551
CPCC07D213/82C07D405/12C07D401/12C07D413/12C07D401/14C07D417/12A61P1/04A61P11/06A61P17/00A61P17/06A61P19/02A61P25/00A61P27/02A61P27/16A61P29/00A61P35/00A61P35/02A61P37/02A61P37/06A61P37/08A61P43/00A61P5/14A61P7/04A61P3/10A61K31/44
Inventor 北村崇博山田肇竹村俊司芦川正教石川哲也三宅祥元纐缬章泰佐藤精一石渡博之天竺桂裕一朗柴崎学小泽孝俊重见亮太土肥武田村正宏
Owner KOWA CO LTD
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