JP2010509240A - 喘息、アレルギー性鼻炎および皮膚障害の治療方法 - Google Patents
喘息、アレルギー性鼻炎および皮膚障害の治療方法 Download PDFInfo
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- JP2010509240A JP2010509240A JP2009535499A JP2009535499A JP2010509240A JP 2010509240 A JP2010509240 A JP 2010509240A JP 2009535499 A JP2009535499 A JP 2009535499A JP 2009535499 A JP2009535499 A JP 2009535499A JP 2010509240 A JP2010509240 A JP 2010509240A
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- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85733906P | 2006-11-07 | 2006-11-07 | |
| PCT/US2007/083695 WO2008058098A2 (en) | 2006-11-07 | 2007-11-06 | Method of treating asthma, allergic rhinitis, and skin disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010509240A true JP2010509240A (ja) | 2010-03-25 |
| JP2010509240A5 JP2010509240A5 (cg-RX-API-DMAC7.html) | 2011-10-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2009535499A Pending JP2010509240A (ja) | 2006-11-07 | 2007-11-06 | 喘息、アレルギー性鼻炎および皮膚障害の治療方法 |
Country Status (12)
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| US (2) | US20080108695A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2079459A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2010509240A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20090086573A (cg-RX-API-DMAC7.html) |
| CN (1) | CN101534806A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2007316482A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0718540A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2668645A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2009004962A (cg-RX-API-DMAC7.html) |
| TW (1) | TW200829232A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008058098A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200902909B (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7687539B1 (en) * | 2005-11-07 | 2010-03-30 | Alcon Research, Ltd. | Method of treating ocular allergy |
| WO2011096941A1 (en) * | 2010-02-08 | 2011-08-11 | Alcon Research, Ltd. | Method of treating ocular allergy |
| CA2788333A1 (en) * | 2010-02-25 | 2011-09-01 | Alcon Research, Ltd. | Method of accelerating corneal wound healing |
| CN110840878B (zh) * | 2019-11-05 | 2020-06-26 | 牡丹江医学院 | 一种用于治疗银屑病的化合物及其制备方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06329568A (ja) * | 1993-02-16 | 1994-11-29 | Adir | 新規な(シクロヘキシル)アルケン化合物、それらの 調製法およびそれらを含む医薬組成物 |
| JPH08512023A (ja) * | 1993-06-15 | 1996-12-17 | ブリガム・アンド・ウイメンズ・ホスピタル | リポキシン化合物 |
| JP2000509386A (ja) * | 1996-05-02 | 2000-07-25 | スコーツイア・リピツドテクニク・アクチエボラーグ | 新規な使用 |
| WO2003040080A2 (en) * | 2001-11-06 | 2003-05-15 | Schering Aktiengesellschaft | Lipoxin a4 analogs |
| US6887901B1 (en) * | 1993-06-15 | 2005-05-03 | Brigham & Women's Hospital, Inc. | Lipoxin compounds and their use in treating cell proliferative disorders |
| US20050203184A1 (en) * | 2003-09-10 | 2005-09-15 | Petasis Nicos A. | Benzo lipoxin analogues |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5286730A (en) * | 1991-09-17 | 1994-02-15 | American Home Products Corporation | Method of treating immunoinflammatory disease |
| US5430049A (en) * | 1993-12-08 | 1995-07-04 | Gaut; Zane N. | Treating hyperproliferative disorders |
| US8815950B2 (en) * | 2003-08-29 | 2014-08-26 | Janssen Biotech, Inc. | Pharmaceutical compositions and method of using levodopa and carbidopa |
| DE602005020178D1 (de) * | 2004-11-09 | 2010-05-06 | Alcon Inc | 5,6,7-trihydroxyheptansäure und analoge zur behandlung von augenkrankheiten und mit hyperproliferativen und angiogenen reaktionen verbundenen krankheiten |
-
2007
- 2007-11-06 MX MX2009004962A patent/MX2009004962A/es not_active Application Discontinuation
- 2007-11-06 KR KR1020097011453A patent/KR20090086573A/ko not_active Ceased
- 2007-11-06 WO PCT/US2007/083695 patent/WO2008058098A2/en not_active Ceased
- 2007-11-06 US US11/935,457 patent/US20080108695A1/en not_active Abandoned
- 2007-11-06 AU AU2007316482A patent/AU2007316482A1/en not_active Abandoned
- 2007-11-06 JP JP2009535499A patent/JP2010509240A/ja active Pending
- 2007-11-06 BR BRPI0718540-5A patent/BRPI0718540A2/pt not_active IP Right Cessation
- 2007-11-06 TW TW096141830A patent/TW200829232A/zh unknown
- 2007-11-06 CN CNA2007800410362A patent/CN101534806A/zh active Pending
- 2007-11-06 CA CA002668645A patent/CA2668645A1/en not_active Abandoned
- 2007-11-06 ZA ZA200902909A patent/ZA200902909B/xx unknown
- 2007-11-06 EP EP07863926A patent/EP2079459A2/en not_active Withdrawn
-
2009
- 2009-02-19 US US12/388,579 patent/US20090156667A1/en not_active Abandoned
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06329568A (ja) * | 1993-02-16 | 1994-11-29 | Adir | 新規な(シクロヘキシル)アルケン化合物、それらの 調製法およびそれらを含む医薬組成物 |
| JPH08512023A (ja) * | 1993-06-15 | 1996-12-17 | ブリガム・アンド・ウイメンズ・ホスピタル | リポキシン化合物 |
| US6887901B1 (en) * | 1993-06-15 | 2005-05-03 | Brigham & Women's Hospital, Inc. | Lipoxin compounds and their use in treating cell proliferative disorders |
| JP2000509386A (ja) * | 1996-05-02 | 2000-07-25 | スコーツイア・リピツドテクニク・アクチエボラーグ | 新規な使用 |
| WO2003040080A2 (en) * | 2001-11-06 | 2003-05-15 | Schering Aktiengesellschaft | Lipoxin a4 analogs |
| US20050203184A1 (en) * | 2003-09-10 | 2005-09-15 | Petasis Nicos A. | Benzo lipoxin analogues |
Non-Patent Citations (3)
| Title |
|---|
| JPN6012057210; Biochem. Biophys. Res. Commun. Vol.180, 1991, pp.1416-1421 * |
| JPN6012057211; Br. J. Clin. Pharmacol. Vol.32, 1991, pp.557-561 * |
| JPN6012057212; Ann. N. Y. Acad. Sci. Vol.624, 1991, pp.244-256 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008058098A3 (en) | 2008-08-07 |
| WO2008058098A2 (en) | 2008-05-15 |
| TW200829232A (en) | 2008-07-16 |
| US20080108695A1 (en) | 2008-05-08 |
| MX2009004962A (es) | 2009-05-21 |
| AU2007316482A1 (en) | 2008-05-15 |
| CA2668645A1 (en) | 2008-05-15 |
| CN101534806A (zh) | 2009-09-16 |
| US20090156667A1 (en) | 2009-06-18 |
| KR20090086573A (ko) | 2009-08-13 |
| ZA200902909B (en) | 2010-07-28 |
| EP2079459A2 (en) | 2009-07-22 |
| BRPI0718540A2 (pt) | 2013-11-19 |
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