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Quinoline derivatives, pharmaceutically acceptable salts thereof, and methods of use thereof

A pharmacy and drug technology, applied to quinoline derivatives, can solve problems such as weak affinity

Active Publication Date: 2020-10-23
VTV THERAPEUTICS LLC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The PDE4 isozyme family has high affinity for cyclic AMP but weak affinity for cyclic GMP

Method used

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  • Quinoline derivatives, pharmaceutically acceptable salts thereof, and methods of use thereof
  • Quinoline derivatives, pharmaceutically acceptable salts thereof, and methods of use thereof
  • Quinoline derivatives, pharmaceutically acceptable salts thereof, and methods of use thereof

Examples

Experimental program
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Embodiment Construction

[0083] Synthesis of compound I and its HCl salt

[0084] step 1:

[0085] To a 40 mL reaction vial was added ethyl 4-chloro-8-methoxyquinoline-3-carboxylate (1.25 g, 4.7 mmol), m-chloroaniline (0.69 g, 5.4 mmol, 1.15 equiv), 1-butanol (10 mL) and acetic acid (0.3 mL). The mixture was stirred at 95°C for 5 hours, IPC LCMS indicated the reaction was complete. 1-Butanol was removed in vacuo, and the mixture was diluted with ethyl acetate (75 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (25 mL), and concentrated to dryness. The residue was purified by flash column chromatography eluting with DCM / ethyl acetate (1:0 to 1:1) to give the ester intermediate 4-(3-chloroanilino)-8-methoxy-quinone Ethyl pheno-3-carboxylate (1.05 g). Yield 62%. LCMS m / e 357.1(M+1) + ; 1 H NMR, 300MHz (CDCl 3 )δ1.45(t,3H),4.08(s,3H),4.44(q,2H),6.84(br d,1H),6.99(t,1H),7.04(dd,1H),7.05(d, 1H), 7.16(t,1H), 7.20s,1H), 7.22(dd,1H), 9.29(s,1H), 10.25(s,1H)ppm.

[0086] S...

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Abstract

The present invention relates to compounds trans-4-[1-(3-chlorphenyl)-7-methoxy-2, 4-dioxo-pyrimido [5, 4-c] quinoline-3-yl] cyclohexanecarboxylic acid, pharmaceutically acceptable salts thereof, andtheir use as therapeutic agents, including in the treatment of inflammatory disorders.

Description

technical field [0001] The present invention relates to the compound trans-4-[1-(3-chlorophenyl)-7-methoxy-2,4-dioxo-pyrimido[5,4-c]quinolin-3-yl] Cyclohexanecarboxylic acid, its pharmaceutically acceptable salts and their use as therapeutic agents for the treatment of TNF-alpha or PDE4 mediated diseases. Background technique [0002] Tumor necrosis factor-α (TNF-α), also known as TNF, DIF, TNF-α, TNFA and TNFSF2, is a cell-associated cytokine that is processed from a 26kd precursor form to a 17kd soluble form. TNF-α has been shown to be a master regulator of inflammation, fever and acute phase responses in humans and animals, similar to those observed during acute infection and shock. Excess TNF-α has been shown to be lethal. There is currently substantial evidence that blocking the action of TNF-alpha, either by using soluble TNF receptors or by using specific neutralizing antibodies, is beneficial in a variety of conditions, including autoimmune diseases such as rheumat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/519A61P11/00A61P11/06A61P11/02A61P37/08A61P29/00A61P19/02A61P17/00A61P17/06A61P1/04A61P13/12A61P25/28A61P25/24A61P1/00A61P9/10A61P25/00A61P1/16A61P21/04A61P1/12A61P27/02A61P31/06A61P9/04A61P35/00A61P37/02A61P7/06A61P25/16A61P31/12A61P7/02A61P19/10A61P17/16A61P1/02A61P3/10
CPCC07D471/04A61P11/00A61P11/06A61P11/02A61P37/08A61P29/00A61P19/02A61P17/00A61P17/06A61P1/04A61P13/12A61P25/28A61P25/24A61P1/00A61P9/10A61P25/00A61P1/16A61P21/04A61P1/12A61P27/02A61P31/06A61P9/04A61P35/00A61P37/02A61P7/06A61P25/16A61P31/12A61P7/02A61P19/10A61P17/16A61P1/02A61P3/10Y02A50/30A61K31/4738
Inventor B.加达姆
Owner VTV THERAPEUTICS LLC
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