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Itaconic acid derivatives and uses thereof in treating an inflammatory disease or a disease associated with an undesirable immune response

A compound and free technology, applied in the direction of diseases, allergic diseases, diseases transmitted by vectors, etc., can solve the problem of losing the biological effect of DMF

Pending Publication Date: 2021-12-21
西特瑞治疗有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is clear that due to the hydrolysis of DMF to MMF in vivo, some of the important biological effects played by DMF in cells are lost

Method used

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  • Itaconic acid derivatives and uses thereof in treating an inflammatory disease or a disease associated with an undesirable immune response
  • Itaconic acid derivatives and uses thereof in treating an inflammatory disease or a disease associated with an undesirable immune response
  • Itaconic acid derivatives and uses thereof in treating an inflammatory disease or a disease associated with an undesirable immune response

Examples

Experimental program
Comparison scheme
Effect test

example

[1088] Analytical equipment

[1089] NMR spectra were recorded using a Bruker 400MHz Avance III spectrometer equipped with a Bruker 5mm probe or a Bruker 500MHz Avance III HD spectrometer equipped with a Bruker 5mm SmartProbeTM. Unless otherwise stated, spectra are measured at 298K and referenced to solvent resonance. Chemical shifts are reported in parts per million. Data were acquired using BrukerTopSpin software.

[1090] UPLC / MS analysis was performed on a Waters Acquity UPLC system using a Waters Acquity CSH C18 or BEH C18 column (2.1 x 30 mm) maintained at a temperature of 40 °C and using a linear acetonitrile gradient appropriate for the lipophilicity of the compound over 3 or 10 minutes. Dissolve at a constant flow rate of 0.77mL / min. The aqueous portion of the mobile phase was 0.1% formic acid (CSH C18 column) or 10 mM ammonium bicarbonate (BEH C18 column). LC-UV chromatograms were recorded between 210 and 400 nm using a Waters Acquity PDA detector. Mass spectr...

example 1-2

[1153] Example 1-2-Methylene succinate 1-(2-cyanoethyl) ester 4-octyl ester

[1154]

preparation example 1

[1155] According to general procedure 2, using 4-octyl itaconate as itaconate monoester and 3-hydroxypropionitrile as R 2 -OH to prepare Example 1. 1 H NMR (500MHz, DMSO-d6) δ6.25(d, J=1.2Hz, 1H), 5.90(d, J=1.3Hz, 1H), 4.27(t, J=6.0Hz, 2H), 4.02(t ,J=6.6Hz,2H),3.39(s,2H),2.92(t,J=6.0Hz,2H),1.58-1.51(m,2H),1.35-1.21(m,10H),0.89-0.84( m,3H). LCMS m / z 318.2 (M+Na) + (ES + ).

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Abstract

The invention relates to compounds of formula (IW-1) and to their use in treating or preventing an inflammatory disease or a disease associated with an undesirable immune response: wherein RA, RB, RC and RD are as defined herein.

Description

technical field [0001] The present invention relates to compounds and their use in the treatment or prevention of inflammatory diseases or diseases associated with adverse immune responses, and to related compositions, methods and intermediate compounds. Background technique [0002] Chronic inflammatory diseases such as rheumatoid arthritis, systemic lupus erythematosus (SLE), multiple sclerosis, psoriasis, Crohn's disease, ulcerative colitis, uveitis, and chronic obstructive Pulmonary disease (COPD) represents a significant burden to society due to lifelong debilitating disease, increased mortality, and high treatment and care costs (Straub R.H. and Schradin C., 2016). Nonsteroidal anti-inflammatory drugs (NSAIDs) are the most widely used drugs for the treatment of inflammatory conditions, but these agents do not prevent the development of inflammation and only treat the accompanying symptoms. Glucocorticoids are potent anti-inflammatory agents, making them an emergency t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/14C07C317/18C07C69/65C07D305/08C07D207/27C07C235/06C07D207/404C07C69/593C07C311/04C07C219/08C07D309/10C07D211/96C07C255/46C07D295/088C07D331/04C07D257/04C07D207/16C07D295/185A61K31/275A61K31/225A61K31/337A61K31/351A61K31/4015A61K31/341A61K31/445A61K31/277A61K31/5375A61K31/397A61K31/495A61K31/54A61K31/38A61K45/06A61P29/00A61P11/00A61P11/06A61P17/06A61P17/00A61P9/10A61P9/04A61P37/02A61P37/00A61P1/00A61P37/06A61P35/00A61P1/16A61P17/14A61P19/02A61P3/10A61P27/16A61P15/00A61P13/12A61P7/00A61P25/00A61P27/12A61P19/00
CPCC07C255/14C07C317/18C07C69/65C07D305/08C07D207/27C07C235/06C07D207/404C07C69/593C07C219/08C07D309/10C07D211/96C07C255/46C07D295/088C07D331/04C07C311/04C07D257/04C07D207/16C07D295/185A61K45/06A61P29/00A61P11/00A61P11/06A61P17/06A61P17/00A61P9/10A61P9/04A61P37/02A61P37/00A61P1/00A61P37/06A61P35/00A61P1/16A61P17/14A61P19/02A61P3/10A61P27/16A61P15/00A61P13/12A61P7/00A61P25/00A61P27/12A61P19/00A61K31/19A61K31/194A61K31/225A61K31/22C07C2601/18C07C2601/14C07C2603/74C07C2603/94C07C2601/04C07C2602/42C07C2602/46C07C51/418C07C69/734C07D307/20C07D309/12C07D205/04C07D471/08Y02A50/30C07C63/26A61K31/351A61K31/41A61K31/5375C07C233/05C07C69/736C07D519/00C07C311/26A61K31/275A61K31/38A61K31/445A61K31/54C07C233/18C07C2601/02C07C69/75C07C67/30C07D207/273A61K31/337A61K31/397A61K31/46C07C311/03C07C317/22C07D207/277C07D295/08C07D451/10A61K31/341A61K31/4015A61K31/495C07C219/10C07C2602/50
Inventor M·L·库克D·卡森M·C·T·法伊夫B·J·特奥尔德S·M·通T·M·沃夫
Owner 西特瑞治疗有限公司