CN101434517A - 治疗免疫疾病的新的1,2-二苯基乙烯衍生物 - Google Patents
治疗免疫疾病的新的1,2-二苯基乙烯衍生物 Download PDFInfo
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- CN101434517A CN101434517A CNA2009100014126A CN200910001412A CN101434517A CN 101434517 A CN101434517 A CN 101434517A CN A2009100014126 A CNA2009100014126 A CN A2009100014126A CN 200910001412 A CN200910001412 A CN 200910001412A CN 101434517 A CN101434517 A CN 101434517A
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/373—Halogenated derivatives with all hydroxy groups on non-condensed rings and with unsaturation outside the aromatic rings
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- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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Abstract
Description
化合物 | IC50(μM) |
5-(2-甲基—2-苯基乙烯基)-2-异丙基-1,3-苯二酚 | 1.15 |
5-(2-甲基—2-苯基乙烯基)-1,3-苯二酚 | 4.65 |
2-[2-(3,5-二羟基-4-异丙基苯基)乙烯基]吡啶盐酸盐 | 2.09 |
2-(3,5-二羟基-4-异丙基苯基)-3-苯基丙烯腈 | 3.50 |
5-(1-甲基—2-苯基乙烯基)-2-异丙基-1,3-苯二酚 | 1.49 |
3-(3,5-二羟基-4-异丙基苯基)-2-苯基丙烯腈 | 1.81 |
2-异丙基-5-(2-噻吩-2-基乙烯基)-1,3-苯二酚 | 5.16 |
化合物 | IC50(μM) |
5-(2-甲基—2-苯基乙烯基)-2-异丙基-1,3-苯二酚 | 0.40 |
5-(2-甲基—2-苯基乙烯基)-1,3-苯二酚 | 1.79 |
2-(3,5-二羟基-4-异丙基苯基)-3-苯基丙烯腈 | 0.13 |
2-异丙基-5-(2-噻吩-2-基乙烯基)-1,3-苯二酚 | 0.028 |
化合物 | % |
5-(2-甲基—2-苯基乙烯基)-2-异丙基-1,3-苯二酚 | 0 |
5-(2-甲基—2-苯基乙烯基)-1,3-苯二酚 | 0 |
5-(1-甲基—2-苯基乙烯基)-2-异丙基-1,3-苯二酚 | 01 |
5-(2,2-二苯基乙烯基)-2-异丙基-1,3-苯二酚 | 47 |
3-(3,5-二羟基-4-异丙基苯基)-2-苯基丙烯腈 | 35 |
2-异丙基-5-(2-噻吩-2-基乙烯基)-1,3-苯二酚 | 23 |
化合物 | IC50(μM) |
2-(3,5-二羟基-4-异丙基苯基)-3-苯基丙烯腈 | 0.86 |
5-(1-甲基—2-苯基乙烯基)-2-异丙基-1,3-苯二酚 | 1.62 |
5-(2,2-二苯基乙烯基)-2-异丙基-1,3-苯二酚 | 1.71 |
3-(3,5-二羟基-4-异丙基苯基)-2-苯基丙烯腈 | 0.71 |
2-异丙基-5-(2-噻吩-2-基乙烯基)-1,3-苯二酚 | 0.08 |
化合物 | % |
5-(2-甲基—2-苯基乙烯基)-1,3-苯二酚 | 42 |
2-[2-(3,5-二羟基-4-异丙基苯基)乙烯基]吡啶盐酸盐 | 75 |
2-(3,5-二羟基-4-异丙基苯基)-3-苯基丙烯腈 | 60 |
2-异丙基-5-(2-噻吩-2-基乙烯基)-1,3-苯二酚 | 23 |
化合物 | % |
5-(2-甲基—2-苯基乙烯基)-2-异丙基-1,3-苯二酚 | 51 |
5-(2-甲基—2-苯基乙烯基)-1,3-苯二酚 | 90 |
2-[2-(3,5-二羟基-4-异丙基苯基)乙烯基]吡啶盐酸盐 | 88 |
5-(1-甲基—2-苯基乙烯基)-2-异丙基-1,3-苯二酚 | 0 |
5-(2,2-二苯基乙烯基)-2-异丙基-1,3-苯二酚 | 10 |
3-(3,5-二羟基-4-异丙基苯基)-2-苯基丙烯腈 | 16 |
2-异丙基-5-(2-噻吩-2-基乙烯基)-1,3-苯二酚 | 2 |
时间(分钟) | % |
1 | 23 |
2 | 10 |
3 | 7 |
4 | 6 |
5 | 6 |
7 | 16 |
10 | 29 |
对照物的% | |
化学发光(mV) | 30 |
化合物 | IC50(μM) |
2-异丙基-5-(2-噻吩-2-基乙烯基)-1,3-苯二酚 | 18.9 |
治疗化合物 | %抑制 |
2-(3,5-二羟基-4-异丙基苯基)-3-苯基丙烯腈 | 85.2 |
0.01%骨化三醇 | 31.2 |
Claims (15)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26207401P | 2001-01-18 | 2001-01-18 | |
US60/262,074 | 2001-01-18 | ||
US32273501P | 2001-09-18 | 2001-09-18 | |
US60/322,735 | 2001-09-18 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB028001214A Division CN100462354C (zh) | 2001-01-18 | 2002-01-17 | 治疗免疫疾病的新的1,2-二苯基乙烯衍生物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101434517A true CN101434517A (zh) | 2009-05-20 |
CN101434517B CN101434517B (zh) | 2014-08-27 |
Family
ID=26949001
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200910001412.6A Expired - Lifetime CN101434517B (zh) | 2001-01-18 | 2002-01-17 | 治疗免疫疾病的1,2-二苯基乙烯衍生物 |
CNB028001214A Expired - Lifetime CN100462354C (zh) | 2001-01-18 | 2002-01-17 | 治疗免疫疾病的新的1,2-二苯基乙烯衍生物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB028001214A Expired - Lifetime CN100462354C (zh) | 2001-01-18 | 2002-01-17 | 治疗免疫疾病的新的1,2-二苯基乙烯衍生物 |
Country Status (10)
Country | Link |
---|---|
US (2) | US20040102517A1 (zh) |
EP (1) | EP1368306B1 (zh) |
JP (1) | JP4230770B2 (zh) |
KR (1) | KR100836207B1 (zh) |
CN (2) | CN101434517B (zh) |
AU (1) | AU2002226225B2 (zh) |
CA (1) | CA2433417C (zh) |
ES (1) | ES2401077T3 (zh) |
HK (1) | HK1128679A1 (zh) |
WO (1) | WO2002057219A1 (zh) |
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US7321050B2 (en) | 1999-12-06 | 2008-01-22 | Welichem Biotech Inc. | Anti-inflammatory and psoriasis treatment and protein kinase inhibition by hydroxy stilbenes and novel stilbene derivatives and analogues |
US20040102517A1 (en) | 2001-01-18 | 2004-05-27 | Genhui Chen | Novel1,2-diphenylethene derivatives for treatment of immune diseases |
MXPA04000695A (es) | 2001-07-23 | 2005-08-26 | Galileo Pharmaceuticals Inc | Compuestos citoprotectores, formulaciones farmaceuticas y cosmeticas y metodos. |
WO2006078941A2 (en) * | 2005-01-20 | 2006-07-27 | Sirtris Pharmaceuticals, Inc. | Novel sirtuin activating compounds and methods of use thereof |
CN1301246C (zh) * | 2005-04-20 | 2007-02-21 | 江苏省原子医学研究所 | 1-氰基-1-(3,5-二甲氧基苯基)-2-(4-r基苯基)乙烯及其制备方法 |
CN1300077C (zh) * | 2005-12-07 | 2007-02-14 | 中国科学院广州化学研究所 | 一种白藜芦醇的制备方法 |
CA2705463C (en) * | 2007-08-10 | 2014-10-07 | Basil Rigas | Anti-inflammatory compounds and uses thereof |
US9040507B2 (en) | 2008-06-02 | 2015-05-26 | Novelmed Therapeutics, Inc. | Method for treating inflammatory conditions |
KR101151861B1 (ko) | 2012-01-10 | 2012-06-08 | ㈜엠알이노베이션 | 여드름 피부개선용 조성물 |
JP2014133732A (ja) * | 2013-07-09 | 2014-07-24 | Meisterbio Co Ltd | ヒスタミン遊離抑制剤 |
US11617724B2 (en) | 2015-05-21 | 2023-04-04 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
US10195160B2 (en) | 2015-05-21 | 2019-02-05 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
WO2019094934A1 (en) | 2017-11-10 | 2019-05-16 | Dermavant Sciences GmbH | Process for preparing tapinarof |
US11497718B2 (en) | 2018-11-13 | 2022-11-15 | Dermavant Sciences GmbH | Use of tapinarof for the treatment of atopic dermatitis |
WO2022200086A1 (en) | 2021-03-25 | 2022-09-29 | Thomas Szekeres | Compounds for use in the treatment and prevention of covid- 19 |
CN113072488A (zh) * | 2021-03-30 | 2021-07-06 | 广东工业大学 | 一种苯乙烯衍生物及其合成方法与应用 |
CN114957171A (zh) * | 2022-06-21 | 2022-08-30 | 广东工业大学 | 一种新颖五元杂环取代的苯乙烯衍生物及其制备方法和应用 |
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WO2003080624A2 (en) | 2002-03-26 | 2003-10-02 | Welichem Biotech Inc. | Dithiolopyrrolone derivatives useful in the treatment of proliferative diseases |
WO2004069243A1 (ja) * | 2003-02-04 | 2004-08-19 | Kabushiki Kaisha Yakult Honsha | 乳癌耐性蛋白(bcrp)阻害剤 |
CN101486666B (zh) | 2007-12-14 | 2014-06-04 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | 具有调节血脂作用的α,β-苯基取代的丙烯酰胺衍生物 |
US7902247B2 (en) * | 2008-01-09 | 2011-03-08 | Allergan, Inc. | Substituted-aryl-2-phenylethyl-1H-imidazole compounds as subtype selective modulators of alpha 2B and/or alpha 2C adrenergic receptors |
US7884228B1 (en) * | 2008-05-06 | 2011-02-08 | Alcon, Inc. | UV-absorbers for ophthalmic lens materials |
-
2002
- 2002-01-17 US US10/466,879 patent/US20040102517A1/en not_active Abandoned
- 2002-01-17 EP EP02716007A patent/EP1368306B1/en not_active Expired - Lifetime
- 2002-01-17 CA CA2433417A patent/CA2433417C/en not_active Expired - Lifetime
- 2002-01-17 WO PCT/CA2002/000059 patent/WO2002057219A1/en active Application Filing
- 2002-01-17 CN CN200910001412.6A patent/CN101434517B/zh not_active Expired - Lifetime
- 2002-01-17 JP JP2002557901A patent/JP4230770B2/ja not_active Expired - Lifetime
- 2002-01-17 KR KR1020027012338A patent/KR100836207B1/ko active IP Right Grant
- 2002-01-17 ES ES02716007T patent/ES2401077T3/es not_active Expired - Lifetime
- 2002-01-17 AU AU2002226225A patent/AU2002226225B2/en not_active Expired
- 2002-01-17 CN CNB028001214A patent/CN100462354C/zh not_active Expired - Lifetime
-
2009
- 2009-02-11 US US12/369,595 patent/US8487009B2/en not_active Expired - Lifetime
- 2009-07-14 HK HK09106335.2A patent/HK1128679A1/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CN100462354C (zh) | 2009-02-18 |
AU2002226225B2 (en) | 2008-03-20 |
CA2433417A1 (en) | 2002-07-25 |
WO2002057219A1 (en) | 2002-07-25 |
KR100836207B1 (ko) | 2008-06-09 |
US20040102517A1 (en) | 2004-05-27 |
JP4230770B2 (ja) | 2009-02-25 |
HK1128679A1 (zh) | 2009-11-06 |
ES2401077T3 (es) | 2013-04-16 |
US8487009B2 (en) | 2013-07-16 |
CN101434517B (zh) | 2014-08-27 |
CN1455766A (zh) | 2003-11-12 |
EP1368306B1 (en) | 2013-01-16 |
CA2433417C (en) | 2010-10-19 |
US20090149548A1 (en) | 2009-06-11 |
KR20020091141A (ko) | 2002-12-05 |
JP2004529085A (ja) | 2004-09-24 |
EP1368306A1 (en) | 2003-12-10 |
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