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Inhibitors of C-FMS kinase
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A CH3, solvate technology, applied in the field of compounds with c-fms kinase inhibitor function
Active Publication Date: 2009-07-01
JANSSEN PHARMA NV
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[0013] The present invention addresses the current need for selective and active proteintyrosine kinase inhibitors by providing active c-fms kinase inhibitors
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[0319] Imidazole-4-carbonitrile (0.50g, 5.2mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMC1) (0.95mL, 5.3mmol), K 2 CO 3 (1.40g, 10.4mmol) and acetone (5mL) were added to the flask and stirred at room temperature for 10h. The mixture was diluted with EtOAc (20 mL), washed with water (20 mL), brine (20 mL), and the organic layer was washed over MgSO 4 dry. The crude product was eluted on a 20-g SPE cartridge (silica gel) with 30% EtOAc / hexanes to afford 0.80 g (70%) of the title compound as a colorless oil. Mass spectrometry (CI(CH 4 ), m / z): C10 h 17 N 3 Theoretical value of OSi, 224.1 (M+H), found value 224.1.
[0343]To N-[2-(4,4-dimethyl-cyclohex-1-enyl)-4-(4-hydroxy-tetrahydro-pyran-4-yl)-phenyl]-5-cyano -1H-imidazole-2-carboxamide (48.0 mg, 0.114 mmol) (the product of step (h) of Example 1) in 1 mL of DCM suspension was added 2-dimethylaminoethanol (0.114 mL, 1.14 mmol), TFA (0.130 mL, 1.17 mmol). The mixture was heated to 50 °C for 8 h. The mixture was concentrated and the title compound was purified by RP-HPLC on a C18 column with a linear gradient of 30-50% CH 3 CN / 0.1% TFA / H 2 O was eluted for 12 min to afford 14 mg (20%) of a white solid. 1 H-NMR (400MHz, CD 3 OD δ 8.21(d, J=8.6Hz, 1H), 7.91(s, 1H), 7.35(dd, J=8.6, 2.2Hz, 1H), 7.21(d, J=2.2Hz, 1H), 5.67(m , 1H), 3.83-3.66(m, 4H), 3.30-3.15(m, 4H), 2.76(s, 6H), 2.26-2.20(m, 2H), 2.12-1.94(m, 6H), 1.51(t , J=6.3Hz, 2H), 1.00 (s, 6H). Mass Spectrum (ESI...
[0347] To N-[2-(4,4-dimethyl-cyclohex-1-enyl)-4-(4-hydroxy-tetrahydro-pyran-4-yl)-phenyl]-5-cyano -1H-Imidazole-2-carboxamide (48.0 mg, 0.114 mmol) (the product of step (h) of Example 1) in 1 mL of DCM was added methyl glycolate (0.215 mL, 2.78 mmol), TFA (0.036 mL, 0.464 mmol). The mixture was stirred at room temperature for 8 h. The mixture was concentrated and the methyl ester of the title compound was eluted on a 10-g SPE cartridge with 50% EtOAc / hexanes. The obtained ester was dissolved in 1 mL MeOH, 2N KOH (0.30 mL, 0.60 mmol) was added, the mixture was stirred at room temperature for 8 h, the title compound was purified by RP-HPLC on a C18 column with a linear gradient of 30-60% CH 3 CN / 0.1%TFA / H 2 O was eluted for 12 min to afford 13 mg (30%) of a white solid. 1 H-NMR (400MHz, CD 3 OD δ 8.34(d, J=8.6Hz, 1H), 7.85...
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[0001] Related Application Cross Reference [0002] This application claims priority to US Patent Provisional Application Serial No. 60 / 793,667, filed April 20, 2006, the contents of which are hereby incorporated by reference in their entirety. Background of the invention [0003] The present invention relates to novel compounds having the function of proteintyrosinekinase inhibitors. More particularly, the present invention relates to novel compounds that function as c-fms kinase inhibitors. [0004] Protein kinases are enzymes that serve as key components of signal transduction pathways, they are catalysts for the translocation of the terminal phosphate of 5'-adenosine triphosphate (ATP) to hydroxyl groups in tyrosine, serine and threonine residues of proteins. Thus, protein kinase inhibitors and substrates are valuable tools for evaluating the physiological consequences of protein kinase activation. Overexpression or inappropriate expression of normal or mutant pro...
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