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Sulfonylureas and related compounds and use of same

A technology of compounds and solvates used in the field of medical treatment and diagnosis of diseases

Active Publication Date: 2018-12-21
THE UNIV OF QUEENSLAND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Other previously characterized NLRP3 inhibitors include parthenolide, 3,4-methylenedioxy-β-nitrostyrene, and dimethylsulfoxide (DMSO), although these agents have limited potency and are nonspecific of

Method used

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  • Sulfonylureas and related compounds and use of same
  • Sulfonylureas and related compounds and use of same
  • Sulfonylureas and related compounds and use of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0448] Example 1: N-((1,2,3,5,6,7-hexahydro-s-indacene-4-yl)carbamoyl)morpholine-4-sulfonamide

[0449]

[0450] Using 4-isocyanato-1,2,3,5,6,7-hexahydro s-indacene (prepared using general method A2) and morpholine-4-sulfonamide in general method C2 gives The title compound, as a white solid (25 mg, 24%). 1 H NMR (400MHz, DMSO-d6): δ=7.98(bs,1H),6.94(s,1H),3.63(t,J=4.0Hz,4H),3.18(t,J=4.0Hz,4H), 2.81 (t, J = 8.0Hz, 4H), 2.68 (t, J = 8.0Hz, 4H), 2.02-1.95 (m, 4H); LCMS purity: >95%; LCMS (m / z): 366 [M +H] + .

Embodiment 2

[0451] Example 2: N-((1,2,3,5,6,7-hexahydro-s-indacene-4-yl)carbamoyl)-4-methylpiperazine-1-sulfonamide

[0452]

[0453] Using 4-isocyanato-1,2,3,5,6,7-hexahydro-s-indacene (prepared using general method A2) and 4-methylpiperazine-1 in general method C3 -sulfonamide The title compound was obtained as a white solid (60 mg, 55%). 1 H NMR (600MHz, DMSO-d 6 ):δ=7.96(bs,1H),6.94(s,1H),3.20(t,J=6.0Hz,4H),2.80(t,J=6.0Hz,4H),2.69(t,J=6.0Hz , 4H), 2.37(t, J=6.0Hz, 4H), 2.19(s, 3H), 2.00-1.95(m, 4H). 13 C NMR (150MHz, DMSO-d 6 ): δ=150.6, 143.5, 137.4, 129.6, 118.1, 54.3, 46.5, 45.9, 32.9, 30.7, 25.5. LCMS purity: >95%; LCMS (m / z): 379[M+H] + . C 18 h 27 N 4 o 3 S 1 (M+H) + HRMS calculated: 379.1798, found: 379.1795.

Embodiment 3

[0454]Example 3: N-[1,2,3,5,6,7-hexahydro-s-indacene-4-yl]-N'-[(dimethylamino)sulfonyl]urea

[0455]

[0456] 4-Isocyanato-1,2,3,5,6,7-hexahydro-s-indacene (prepared using General Method A2) and N,N-dimethyl Sulfonamide afforded the title compound as a white solid (29 mg, 31%). 1 H NMR (400MHz, DMSO-d 6 ):δ=7.96(s,1H),6.94(s,1H),2.81(t,J=8Hz,4H),2.79(s,6H),2.70(t,J=8Hz,4H),2.02-1.96 (m,4H). 13 C NMR (150MHz, DMSO-d 6 ): δ=143.4, 142.9, 137.4, 125.1 117.9, 38.6, 32.9, 30.7, 25.5; LCMS (m / z): 324[M+H] + ;C 15 h 21 N 3 o 3 S 1 (M+H) + , HRMS calculated value: 324.13764, measured value: 324.13891.

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Abstract

The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts, solvates and prodrugs thereof: Formula (I) wherein Q is selected from O, S and Se; J is S or Se; W1 and W2, when present, are independently selected from N and C; R1 and R2 are independently selected from the group consisting of hydrogen, C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, aryl, heterocyclyl,heteroaryl, cycloalkyl, cycloalkenyl, amino, amido, alkylthio, acyl, arylalkyl and acylamido, all of which may be optionally substituted; and wherein at least one of W1 and W2 is present and is a nitrogen atom and when R1 and R2 are cyclic then the respective W1 or W2 may form part of the ring structure. The present invention also relates to pharmaceutical compositions including such compounds, tomethods of treatment using such compounds, in particular in relation to NLRP3 inflammasome mediated disorders, and to associated diagnostic uses.

Description

technical field [0001] The present invention relates to the field of medical treatment and diagnosis of diseases. More specifically, the present invention relates to novel sulfonylureas and related compounds and their use in the treatment or identification of diseases or conditions responsive to inhibition of NLRP3 or activation of NLRP3 or related components of the inflammatory process. Background technique [0002] Any reference herein to background art is not to be construed as an admission that such art forms common general knowledge, in Australia or elsewhere. [0003] The NOD-like receptor (NLR) family, pyridine domain-containing protein 3 (NLRP3) inflammasome is a component of the inflammatory process and its aberrant activation in genetic disorders such as cryopyrin-associated periodic syndrome (CAPS) and complex diseases such as multiple sclerosis, type 2 diabetes, Alzheimer's disease and atherosclerosis. [0004] NLRP3 is an intracellular signaling molecule that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/18C07C307/06C07C307/08C07C307/10C07D295/26A61P29/00
CPCC07D231/18C07C307/06C07C307/10C07D295/26C07C2601/14C07C2602/08C07C2603/10A61P1/00A61P1/04A61P1/16A61P11/00A61P11/06A61P11/14A61P13/12A61P17/00A61P17/02A61P17/06A61P17/10A61P19/02A61P19/04A61P19/06A61P21/00A61P25/00A61P25/02A61P25/16A61P25/22A61P25/24A61P25/28A61P27/02A61P29/00A61P29/02A61P3/00A61P3/04A61P31/04A61P31/12A61P31/14A61P31/16A61P31/18A61P33/00A61P35/00A61P35/02A61P35/04A61P37/00A61P37/02A61P37/06A61P39/02A61P43/00A61P5/00A61P7/00A61P7/02A61P7/06A61P9/00A61P9/04A61P9/08A61P9/10A61P9/12A61P3/10A61K31/4045A61K31/415A61K31/42A61K31/423A61K31/5375C07D209/40C07D211/96C07D235/30C07D237/22C07D239/32C07D241/04C07D249/18C07D261/20C07D263/58C07D271/12A61K49/0004C07C311/47C07D209/08C07D209/14C07D213/42C07D233/64C07D235/26C07D271/06C07D277/28C07D307/52C07D311/20C07D317/66C07D403/12C07D413/04C07D413/12
Inventor L·奥尼尔R·科尔M·库珀A·罗伯逊K·施罗德A·M·麦克莱昂德D·J·米勒
Owner THE UNIV OF QUEENSLAND
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