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Novel sulfonamideurea compounds
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A compound and solvate technology, applied in the field of sulfonylurea and sulfonylurea, can solve the problems of limited efficacy and non-specificity
Pending Publication Date: 2021-04-16
INFLAZOME LTD
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Embodiment 1
[0983] Example 1: 3-(N-methyl-N-(1-methylpyrrolidin-3-yl)sulfamoyl)-1-(5-(2-methoxypyridin-4-yl)-2,3-di Hydrogen-1H-inden-4-yl)urea
[0984]
[0985] To a cooled (0°C) solution of chlorosulfonyl isocyanate (59 mg, 0.41 mmol) in DCM (5 mL) was added 5-(2-methoxypyridin-4-yl)-2,3-dihydro-1H- Indene-4-amine (Intermediate A2; 100 mg, 0.41 mmol). The mixture was stirred at 0°C for 10 minutes. N,1-Dimethylpyrrolidin-3-amine (95 mg, 0.83 mmol) in DCM (5 mL) was added and the reaction was allowed to reach room temperature over 30 minutes. The mixture was evaporated to dryness in vacuo and purified by reverse phase chromatography to give the title compound (9 mg; 5%) as a white solid.
[0987] LCMS: m / z 460 (M+H) + (ES + ); 458(M-H) - (ES - ).
Embodiment 2
[0988] Example 2: 3-(N-methyl-N-((1-methylpyrrolidin-2-yl)methyl)sulfamoyl)-1-(5-(2-methoxypyridin-4-yl)-2 ,3-dihydro-1H-inden-4-yl)urea
[0989]
[0990] As for 3-(N-methyl-N-(1-methylpyrrolidin-3-yl)sulfamoyl)-1-(5-(2-methoxypyridin-4-yl)-2,3 -dihydro-1H-inden-4-yl)urea (Example 1) using chlorosulfonyl isocyanate (59 mg, 0.41 mmol), 5-(2-methoxypyridin-4-yl)-2, 3-Dihydro-1H-inden-4-amine (Intermediate A2; 100 mg, 0.41 mmol) and N-methyl-1-(1-methylpyrrolidin-2-yl)methanamine (racemic intermediate P23; 107 mg, 0.83 mmol) to give the title compound (2 mg; 1%) as a white solid.
[0993] Example 3: 3-(N-methyl-N-((1-methylpyrrolidin-2-yl)methyl)sulfamoyl)-1-(7-fluoro-5-(2-methoxypyridine-4- yl)-2,3-dihydro-1H-inden-4-yl)urea
[0994]
[0995] As for 3-(N-methyl-N-(1-methylpyrrolidin-3-yl)sulfamoyl)-1-(5-(2-methoxypyridin-4-yl)-2,3 -dihydro-1H-inden-4-yl)urea (Example 1) using chlorosulfonyl isocyanate (55 mg, 0.38 mmol), 7-fluoro-5-(2-methoxypyridin-4-yl) )-2,3-dihydro-1H-indene-4-amine (Intermediate A1; 100 mg, 0.38 mmol) and N,1-dimethylpyrrolidin-3-amine (95 mg, 0.83 mmol) to give The title compound (12 mg; 10%) as a white solid.
[0996] 1 H NMR (CD 3 OD)δ8.14(d,1H),7.08(d,1H),6.98(m,2H),4.48(m,1H),3.92(s,3H),2.98(m,8H),2.71(s, 3H), 2.60 (s, 3H), 2.10 (m, 3H) and 1.92 (m, 1H).
[0997] LCMS: m / z 479 (M+H) + (ES + ).
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Abstract
The present invention relates to compounds of formula (I): wherein Q is selected from O or S; R1 and R3 are each independently hydrogen or an optionally substituted hydrocarbyl group, or R1 and R3 together with the nitrogen atom to which they are attached may form a 3- to 12-membered optionally substituted cyclic group; and R2 is a cyclic group substituted at the oposition, wherein R2 may optionally be further substituted. The present invention further relates to salts, solvates and prodrugs of such compounds, to pharmaceutical compositions comprising such compounds, and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by the inhibition of NLRP3.
Description
[0001] Field of Invention [0002] The present invention relates to sulfonylureas and sulfonyl thioureas comprising N-bonded substituents attached to a sulfur atom of a sulfonylurea or sulfonylthiourea group and attached to a urea or α-substituted cyclic groups of nitrogen atoms of thiourea groups; and related salts, solvates, prodrugs and pharmaceutical compositions. The present invention also relates to the use of such compounds for the treatment and prevention of medical conditions and diseases, particularly by inhibiting NLRP3. Background technique [0003] The NOD-like receptor (NLR) family pyrin domain-containing protein 3 (NLRP3) inflammasome is a component of the inflammatory process, and its abnormal activity is a consequence of genetic disorders such as cold pyridine-related periodic syndrome ( cryopyrin-associated periodic syndrome, CAPS) and the pathogenesis of complex diseases such as multiple sclerosis, type 2 diabetes, Alzheimer's disease, and atherosclerosis....
Claims
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