KR20140145203A - 포르밀 펩타이드 수용체 2 조절물질로서 (2-우레이도아세트아미도)알킬 유도체 - Google Patents
포르밀 펩타이드 수용체 2 조절물질로서 (2-우레이도아세트아미도)알킬 유도체 Download PDFInfo
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| PCT/US2013/036715 WO2013158597A1 (en) | 2012-04-16 | 2013-04-16 | (2-ureidoacetamido)alkyl derivatives as formyl peptide receptor 2 modulators |
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| AU2014226001B2 (en) | 2013-03-06 | 2018-12-06 | Allergan, Inc. | Use of agonists of Formyl peptide receptor 2 for treating dermatological diseases |
| BR112016011417A8 (pt) | 2013-11-21 | 2020-05-05 | Allergan Inc | derivados de fenilcarbamatos como moduladores do receptor de formil peptídeo, composição farmacêutica, e seus usos |
| EP3305763B1 (en) | 2013-11-28 | 2019-07-24 | Kyorin Pharmaceutical Co., Ltd. | Deuterated or isotopically labeled urea derivatives or pharmacologically acceptable salts thereof useful as fprl-1 agonists |
| US9604934B2 (en) | 2014-01-29 | 2017-03-28 | Allergan, Inc. | Urea hydantoin derivatives as formyl peptide modulators |
| US9663457B2 (en) | 2014-04-09 | 2017-05-30 | Allergan, Inc. | Carbamoyl hydrazine derivatives as formyl peptide modulators |
| KR20170005121A (ko) | 2014-05-21 | 2017-01-11 | 알러간, 인코포레이티드 | 폼일 펩타이드 수용체 조절제로서의 이미다졸 유도체 |
| TW201718473A (zh) * | 2015-08-05 | 2017-06-01 | 歐樂根公司 | 作為甲醯肽受體１（ｆｐｒ１）選擇性促效劑之苯基脲類似物 |
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| KR102615095B1 (ko) * | 2017-06-09 | 2023-12-15 | 브리스톨-마이어스 스큅 컴퍼니 | 피페리디논 포르밀 펩티드 2 수용체 효능제 |
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| US7109243B2 (en) * | 2003-03-24 | 2006-09-19 | Irm Llc | Inhibitors of cathepsin S |
| US7576206B2 (en) * | 2003-08-14 | 2009-08-18 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| CN100506802C (zh) | 2004-06-04 | 2009-07-01 | 中国科学院上海药物研究所 | 一类甲酰肽样受体-1调节剂、其制备方法和用途 |
| WO2006065755A2 (en) * | 2004-12-13 | 2006-06-22 | Glaxo Group Limited | Quaternary ammonium salts of fused hetearomatic amines as novel muscarinic acetylcholine receptor antagonists |
| EP2585054A1 (en) * | 2010-06-24 | 2013-05-01 | Allergan, Inc. | Derivatives of cycloalkyl- and cycloalkenyl-1,2-dicarboxylic acid compounds having formyl peptide receptor like-1 (fprl-1) agonist or antagonist activity |
| AU2014226001B2 (en) * | 2013-03-06 | 2018-12-06 | Allergan, Inc. | Use of agonists of Formyl peptide receptor 2 for treating dermatological diseases |
| EP2964213B1 (en) * | 2013-03-06 | 2020-11-04 | Allergan, Inc. | Use of agonists of formyl peptide receptor 2 for treating ocular inflammatory diseases |
-
2013
- 2013-04-16 SG SG11201406629VA patent/SG11201406629VA/en unknown
- 2013-04-16 AU AU2013249474A patent/AU2013249474A1/en not_active Abandoned
- 2013-04-16 CN CN201380025558.9A patent/CN104302630A/zh active Pending
- 2013-04-16 EP EP13718477.6A patent/EP2838887B1/en active Active
- 2013-04-16 ES ES13718477T patent/ES2711363T3/es active Active
- 2013-04-16 WO PCT/US2013/036715 patent/WO2013158597A1/en not_active Ceased
- 2013-04-16 CA CA2870356A patent/CA2870356A1/en not_active Abandoned
- 2013-04-16 JP JP2015507101A patent/JP2015520130A/ja active Pending
- 2013-04-16 US US13/863,934 patent/US9670150B2/en active Active
- 2013-04-16 KR KR1020147031783A patent/KR20140145203A/ko not_active Withdrawn
- 2013-04-16 NZ NZ700733A patent/NZ700733A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ700733A (en) | 2016-07-29 |
| JP2015520130A (ja) | 2015-07-16 |
| EP2838887A1 (en) | 2015-02-25 |
| SG11201406629VA (en) | 2014-11-27 |
| ES2711363T3 (es) | 2019-05-03 |
| EP2838887B1 (en) | 2018-11-21 |
| US20130274230A1 (en) | 2013-10-17 |
| US9670150B2 (en) | 2017-06-06 |
| WO2013158597A1 (en) | 2013-10-24 |
| CN104302630A (zh) | 2015-01-21 |
| CA2870356A1 (en) | 2013-10-24 |
| AU2013249474A1 (en) | 2014-11-06 |
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