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8-quinoline sulfonamide compound and application thereof

A quinoline sulfonamide and compound technology, applied in the field of medicinal chemistry, can solve problems such as incomplete remission

Pending Publication Date: 2022-08-09
ANHUI RUBIOX VISION BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Drugs currently approved by the FDA to treat RA often provide temporary or incomplete symptom relief and are associated with serious side effects

Method used

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  • 8-quinoline sulfonamide compound and application thereof
  • 8-quinoline sulfonamide compound and application thereof
  • 8-quinoline sulfonamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of compound f1:

[0040]

[0041] Compound d (299 mg, 1 mM) was dissolved in 2 mL of pyridine, and then benzenesulfonyl chloride (substituent R was hydrogen) (176 mg, 1 mM) was added to react at room temperature for 8-12 h. The progress of the reaction was checked by TLC. After the reaction was completed, the reaction solvent was removed. Compound f1 was obtained by ethyl acetate:petroleum ether (1:4) column chromatography to obtain compound f1, which was a white solid with a yield of 68%.

[0042] 1 H NMR (500MHz, DMSO-d 6 )δ10.09(d,J=28.9Hz,2H),9.11(dd,J=4.3,1.8Hz,1H),8.50(d,J=8.4Hz,1H),8.28(dd,J=15.5,7.1 Hz, 2H), 7.79(d, J=7.0Hz, 1H), 7.60(t, J=7.7Hz, 1H), 7.54(t, J=7.4Hz, 2H), 7.50(d, J=7.1Hz, 2H), 7.40(t, J=7.8Hz, 2H), 7.06(s, 1H), 6.89(t, J=8.1Hz, 1H), 6.69(d, J=8.1Hz, 1H), 6.54(d, J=8.0Hz, 1H); 13 C NMR (126MHz, DMSO) δ 151.38, 142.61, 139.27, 138.10, 136.84, 134.97, 134.14, 132.69, 132.10, 129.23, 128.93, 127.67, 126.37, 125.51, 122.54, 115.9...

Embodiment 2

[0044] Synthesis of compound f2:

[0045]

[0046] The method is the same as in Example 1, except that the substituent R in the benzenesulfonyl chloride is 4-methyl, and a white solid, namely compound f2, is obtained in a yield of 70%.

[0047] 1 H NMR (500MHz, DMSO-d 6 )δ10.31(s, 2H), 9.33(dd, J=4.2, 1.9Hz, 1H), 8.72(d, J=8.2Hz, 1H), 8.51(dd, J=23.6, 7.9Hz, 2H), 7.98–7.86(m, 2H), 7.61(d, J=8.3Hz, 2H), 7.40(d, J=7.9Hz, 2H), 7.28(s, 1H), 7.10(t, J=8.1Hz, 1H) ), 6.89(d, J=8.1Hz, 1H), 6.74(d, J=8.0Hz, 1H), 2.50(s, 3H); 13 C NMR (126MHz, DMSO) δ 151.46, 143.07, 142.67, 138.50, 138.31, 136.90, 136.44, 135.00, 134.21, 132.23, 129.44, 128.38, 126.53, 125.57, 122.61, 20.617, 110.61, 115.61.

Embodiment 3

[0049] Synthesis of compound f3:

[0050]

[0051] The method is the same as in Example 1, except that the substituent R in the benzenesulfonyl chloride is 4-isopropyl, and a white solid, namely compound f3, is obtained in a yield of 76%.

[0052] 1 H NMR (500MHz, DMSO-d 6 )δ10.15(s, 2H), 9.12(dd, J=4.2, 1.8Hz, 1H), 8.52(dd, J=8.4, 1.8Hz, 1H), 8.33(dd, J=7.3, 1.5Hz, 1H) ),8.28(dd,J=8.3,1.4Hz,1H),7.75–7.66(m,2H),7.46(d,J=8.5Hz,2H),7.27(d,J=8.5Hz,2H),7.10 (t, J=2.1Hz, 1H), 6.88 (t, J=8.1Hz, 1H), 6.67 (dd, J=8.1, 1.2Hz, 1H), 6.53 (dd, J=8.1, 1.2Hz, 1H) ,2.89(p,J=6.9Hz,1H),1.14(d,J=6.9Hz,7H); 13 C NMR (126MHz, DMSO) δ 153.51, 151.48, 142.71, 138.56, 138.37, 136.95, 135.06, 134.24, 132.25, 129.35, 128.41, 126.98, 126.66, 125.60, 122.63, 3.3.2.9,2,17

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Abstract

The invention relates to an 8-quinoline sulfonamide compound and application thereof. R is hydrogen, 4-methyl, 4-isopropyl, 2, 4, 6-triisopropyl, 4-tert-butyl, 2, 4-dimethoxy, 3, 4-dimethoxy, 2-fluorine, 3-fluorine, 4-fluorine, 2, 6-difluorine, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 3, 5-di-trifluoromethyl, 2-trifluoromethoxy, 4-trifluoromethoxy, 2-chlorine, 4-chlorine, 2, 6-dichloro, 3, 4-dimethoxy, 4-tert-butyl, 2, 4-dimethoxy, 3, 4-dimethoxy, 4-tert-butyl, 2, 4-dimethoxy, 3, 4-dimethoxy, 2-trifluoromethyl, 3, 5-di-trifluoromethyl, 2-trifluoromethoxy, 4-trifluoromethoxy, 2-chlorine, 4-chlorine, 2, 6-dichloro, 3, the compound is any one of 2, 5-dichloro, 2-bromo, 3-bromo, 4-bromo, 3-bromine-5-trifluoromethyl and the like. The compound has an inhibiting effect on generation of macrophage NO stimulated by LPS, can reduce release of inflammation-related cytokines and expression of protein, and has the potential to be developed into a medicine for treating inflammatory diseases.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, in particular to an 8-quinoline sulfonamide compound and an application thereof. Background technique [0002] Rheumatoid arthritis (RA) is a chronic autoimmune disease characterized by infiltration of synovial inflammatory cells in the joint cavity and bone erosion due to the formation of pannus. In recent years, with the aging of the global population, the prevalence of RA has increased year by year. Severe RA can lead to joint deformity, limited mobility and even loss of function, which is highly disabling. [0003] The pathogenesis of RA is extremely complex, and no definite etiology has been found so far. At present, the pathogenesis of RA includes immune factors, environmental factors, and genetic susceptibility factors. Many research reports indicate that the body's immune factors play an important role in the pathogenesis of RA. Interleukin (IL-1β) and tumor necrosis facto...

Claims

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Application Information

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IPC IPC(8): C07D215/36A61P29/00A61P19/02A61K31/47
CPCC07D215/36A61P29/00A61P19/02
Inventor 汪国兴邢思齐刘培培樊丽徐文亮
Owner ANHUI RUBIOX VISION BIOTECH
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