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Inhibiting platelet derivative growth factor and/or quinoline and quinowoline compounds of P56lek tyrosinkinase
Inactive Publication Date: 2001-01-17
AVENTIS PHARMACETICAL PRODUCTS INC
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With respect to quinoline or quinoxalinyl compounds, no Lck inhibitors in this area have been reported
Method used
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[0057] In one aspect, the preferred compound of the present invention is a compound of formula I, or an N-oxide thereof, a hydrate thereof, a solvate thereof, a prodrug thereof, or a pharmaceutically acceptable salt thereof, wherein:
[0058] L 1 for (CR 3a R 3b ) m -Z 3 -(CR 3′a R 3′b ) n ;
[0059] L 2 for (CR 3a R 3b ) p -Z 4 -(CR 3′a R 3′b ) q ;
[0060] Z 2 is optionally substituted hydroxycycloalkyl or optionally substituted hydroxycycloalkenyl;
[0061] Z 4 for O and NR 4 ;
[0062] m is 0;
[0063] n is 2 or 3,
[0064] p+q=0 or 1;
[0065] R 1a and R 1b is independently optionally substituted alkyl, optionally substituted alkoxy, optionally substituted cycloalkoxy, optionally substituted heterooxyoxy, or R 5 R 6 N-, or R 1a and R 1b one of which is hydrogen or halogen;
[0066] R 1c is hydrogen, optionally substituted alkyl or optionally substituted alkoxy;
[0067] R 3a , R 3b , R 3′a and R 3′b are independently hydrogen or lower a...
Embodiment 1
[0152] At 0°C, add 3-hydroxy-6,7-dimethoxyquinoline (0.237g, 1.15mmol), cyclohexanol (0.347g, 3.46mmol), Ph 3 P (0.908g, 3.46mmol). Diethyl azodicarboxylate was added in portions until the solution remained dark red (0.663 g, 3.81 mmol). After 4 hours, the solution was concentrated and the residue was chromatographed (50% EtOAc / hexanes). The product was recrystallized from isopropanol / hexane as the HCl salt as a white solid (m.p. 229-232°C, decomposed). Example 2 2-anilino-6-isopropoxy-quinoxalinehydrochloride
Embodiment 2
[0153] Under argonatmosphere, 1 mL DMF was added to NaH (0.033 g, 0.84 mmol), and 2-anilino-6-quinoxalinol (0.1 g, 0.42 mmol) / 1.5 mL DMF was added in portions. After 30 minutes, 2-bromopropane was added dropwise, and the solution was heated to 50°C for 1.5 hours. The cooled reaction mixture was quenched with water and partitioned between EtOAc and H 2 Within O, use H2 O(3X), washed with brine, dried (MgSO 4 ) and concentrate. The resulting residue was chromatographed (30% EtOAc / hexanes) to afford 0.05 g of the dialkylated product and 0.1 g of the title compound. Samples for analysis of the HCl salt were prepared as follows: Et to the free base 2 Add IPA (isopropanol) / HCl to O / IPA solution to obtain HCl salt (n.p.205-210°C decomposition). Elemental Analysis C 17 h 17 N 3 O·HCl: Calculated: C, 64.65; H, 5.74; N, 13.31; Found: C, 64.51; H, 5.90; N, 13.09. Example 3 2-anilino-6-methoxy-quinoxaline hydrochloride
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the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
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