RU2345759C2 - Применение хиральных арилкетонов в лечении нейтрофил-зависимых воспалительных заболеваний - Google Patents

Применение хиральных арилкетонов в лечении нейтрофил-зависимых воспалительных заболеваний Download PDF

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RU2345759C2
RU2345759C2 RU2005121554/04A RU2005121554A RU2345759C2 RU 2345759 C2 RU2345759 C2 RU 2345759C2 RU 2005121554/04 A RU2005121554/04 A RU 2005121554/04A RU 2005121554 A RU2005121554 A RU 2005121554A RU 2345759 C2 RU2345759 C2 RU 2345759C2
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phenyl
isobutylphenyl
methyl
formula
group
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RU2005121554/04A
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Russian (ru)
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RU2005121554A (ru
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Марчелло АЛЛЕГРЕТТИ (IT)
Марчелло Аллегретти
Риккардо БЕРТИНИ (IT)
Риккардо БЕРТИНИ
Мари Кандида ЧЕСТА (IT)
Мария Кандида ЧЕСТА
Чинци БИЦЦАРРИ (IT)
Чинция БИЦЦАРРИ
Франческо КОЛОТТА (IT)
Франческо Колотта
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    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
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RU2005121554/04A 2002-12-10 2003-12-09 Применение хиральных арилкетонов в лечении нейтрофил-зависимых воспалительных заболеваний RU2345759C2 (ru)

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EP02027453 2002-12-10
EP02027453.6 2002-12-10

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RU2005121554A RU2005121554A (ru) 2006-01-20
RU2345759C2 true RU2345759C2 (ru) 2009-02-10

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RU2005121554/04A RU2345759C2 (ru) 2002-12-10 2003-12-09 Применение хиральных арилкетонов в лечении нейтрофил-зависимых воспалительных заболеваний

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US (2) US20060247297A1 (enExample)
EP (1) EP1581474B1 (enExample)
JP (1) JP5021169B2 (enExample)
CN (1) CN100383110C (enExample)
AT (1) ATE406343T1 (enExample)
AU (1) AU2003289993B8 (enExample)
CA (1) CA2507765C (enExample)
CY (1) CY1108596T1 (enExample)
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NO (1) NO332223B1 (enExample)
PT (1) PT1581474E (enExample)
RU (1) RU2345759C2 (enExample)
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WO (1) WO2004052830A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2421213C1 (ru) * 2010-02-24 2011-06-20 Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) Применение 2-гидрокси-3-метил-6-(1-метилэтенил)циклогекс-3-енона в качестве анальгезирующего средства

Families Citing this family (3)

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Publication number Priority date Publication date Assignee Title
CN109928868A (zh) * 2019-03-22 2019-06-25 河北科技大学 1,3-双(2,5-二甲基苯基)丙-2-酮的合成方法及其应用
CN115894198B (zh) * 2022-11-04 2024-05-17 浙江永太科技股份有限公司 Qulipta的关键中间体1-(2,3,6-三氟苯基)丙烷-2-酮的制备方法
KR102597093B1 (ko) * 2023-06-07 2023-11-03 옙바이오 주식회사 줄기세포 노화 억제 신규 화합물 및 이의 약학적 용도

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000024710A1 (en) * 1998-10-23 2000-05-04 Dompe' S.P.A. N-(2-aryl-propionyl)-sulfonamides and pharmaceutical preparations containing them
WO2001058852A2 (en) * 2000-02-11 2001-08-16 Dompé S.p.A. (r)-2-aryl-propionamides, useful in the inhibition of il-8-induced chemiotaxis of neutrophils

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL125956C (enExample) * 1960-07-26
US3591350A (en) * 1968-06-17 1971-07-06 M & T Chemicals Inc Novel plating process
SE385883B (sv) * 1972-04-10 1976-07-26 Ciba Geigy Ag Forfarande for framstellning av nya pyridinkarbonsyraestrar
JPS5842851B2 (ja) 1976-03-05 1983-09-22 三井東圧化学株式会社 ２−（４′−アルキルフエニル）プロピオン酸の製造方法
US4151172A (en) 1977-08-11 1979-04-24 E. R. Squibb & Sons, Inc. Phosphonoacyl prolines and related compounds
JPS5697249A (en) 1979-12-30 1981-08-05 Ota Seiyaku Kk Preparation of 2-arylalkane acid
JP2782359B2 (ja) 1989-06-22 1998-07-30 日本石油化学株式会社 ２―（４―イソブチルフエニル）―２―ブテン
AU644281B2 (en) 1991-04-24 1993-12-02 Sumitomo Pharmaceuticals Company, Limited Novel thiazole derivatives
JPH05286902A (ja) * 1992-04-10 1993-11-02 Sumitomo Pharmaceut Co Ltd α−クロロ−β−ケトエステル誘導体の製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000024710A1 (en) * 1998-10-23 2000-05-04 Dompe' S.P.A. N-(2-aryl-propionyl)-sulfonamides and pharmaceutical preparations containing them
WO2001058852A2 (en) * 2000-02-11 2001-08-16 Dompé S.p.A. (r)-2-aryl-propionamides, useful in the inhibition of il-8-induced chemiotaxis of neutrophils

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MEYERS A.I. ET AL "An asymmetric synthesis of acyclic and macrocyclic α-alcyi ketones. The role of (E)- and (Z)-lithioenamines." J. Am. Chem. Soc., 1981, v.103, №11, p.3088-3093. WRIGHT J. В. ET AL "Aminosubstituted diphenylacetones, J. Am. Chem., 1959, v.81, p.5193-5197. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2421213C1 (ru) * 2010-02-24 2011-06-20 Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) Применение 2-гидрокси-3-метил-6-(1-метилэтенил)циклогекс-3-енона в качестве анальгезирующего средства

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ATE406343T1 (de) 2008-09-15
WO2004052830A1 (en) 2004-06-24
AU2003289993B8 (en) 2008-05-08
NO332223B1 (no) 2012-07-30
RU2005121554A (ru) 2006-01-20
JP2006509022A (ja) 2006-03-16
US20090203652A1 (en) 2009-08-13
AU2003289993A1 (en) 2004-06-30
NO20053086L (no) 2005-06-23
PT1581474E (pt) 2008-12-09
HK1085721A1 (zh) 2006-09-01
JP5021169B2 (ja) 2012-09-05
CN1732145A (zh) 2006-02-08
SI1581474T1 (sl) 2009-02-28
CA2507765A1 (en) 2004-06-24
ES2312834T3 (es) 2009-03-01
CA2507765C (en) 2012-03-20
US20060247297A1 (en) 2006-11-02
DE60323264D1 (de) 2008-10-09
CN100383110C (zh) 2008-04-23
AU2003289993B2 (en) 2008-04-24
EP1581474B1 (en) 2008-08-27
DK1581474T3 (da) 2008-12-08
EP1581474A1 (en) 2005-10-05
CY1108596T1 (el) 2014-04-09

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