JP2000508645A - ポリ不飽和脂肪酸を使用する免疫病の治療方法 - Google Patents
ポリ不飽和脂肪酸を使用する免疫病の治療方法Info
- Publication number
- JP2000508645A JP2000508645A JP9536587A JP53658797A JP2000508645A JP 2000508645 A JP2000508645 A JP 2000508645A JP 9536587 A JP9536587 A JP 9536587A JP 53658797 A JP53658797 A JP 53658797A JP 2000508645 A JP2000508645 A JP 2000508645A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- polyunsaturated fatty
- double bonds
- thia
- oxa
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- Biomedical Technology (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| AUPN9250A AUPN925096A0 (en) | 1996-04-12 | 1996-04-12 | Methods of treatment |
| AUPN9538A AUPN953896A0 (en) | 1996-04-26 | 1996-04-26 | Treatment of t-cell mediated diseases |
| PCT/AU1997/000231 WO1997038688A1 (en) | 1996-04-12 | 1997-04-14 | Methods of treating immunopathologies using polyunsaturated fattyacids |
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| JP2000508645A true JP2000508645A (ja) | 2000-07-11 |
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| US (1) | US6262119B1 (2) |
| EP (1) | EP0904072A4 (2) |
| JP (1) | JP2000508645A (2) |
| CA (1) | CA2251780A1 (2) |
| GB (1) | GB2328155B (2) |
| WO (1) | WO1997038688A1 (2) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016500092A (ja) * | 2012-11-27 | 2016-01-07 | アヴェクシン エーエス | 皮膚炎治療 |
| US10823981B2 (en) | 2012-03-27 | 2020-11-03 | Adlens Ltd. | Deformable non-round membrane assemblies |
| US10953004B2 (en) | 2016-03-14 | 2021-03-23 | Avexxin As | Combination therapy for proliferative diseases |
| US11351127B2 (en) | 2016-09-21 | 2022-06-07 | Avexxin As | Pharmaceutical composition |
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| AU770726B2 (en) * | 1998-10-20 | 2004-02-26 | Vlaams Interuniversitair Instituut Voor Biotechnologie Vzw | Use of a cytokine-producing lactococcus strain to treat colitis |
| AUPQ291499A0 (en) * | 1999-09-17 | 1999-10-07 | Women's And Children's Hospital Adelaide | Novel nitro and sulphur containing compounds |
| NO328803B1 (no) * | 2000-03-03 | 2010-05-18 | Thia Medica | Nye fettsyreanaloger |
| WO2002011676A2 (en) | 2000-08-04 | 2002-02-14 | Dmi Biosciences, Inc. | Method of using diketopiperazines and composition containing them |
| NO20006008L (no) * | 2000-11-28 | 2002-05-29 | Thia Medica As | Fettsyreanaloger for behandling av inflammatoriske og autoimmune sykdommer |
| US7780961B2 (en) * | 2001-05-03 | 2010-08-24 | Actogenix N.V. | Self-containing Lactococcus strain |
| NZ539735A (en) * | 2002-10-02 | 2009-07-31 | Dmi Biosciences Inc | Diagnosis and monitoring of diseases using markers, such as diketopiperazines |
| CA2506031A1 (en) * | 2002-11-15 | 2004-06-03 | Vib Vzw | Self-containing lactobacillus strain comprising a thya mutation and therapeutic applications thereof |
| GB0311081D0 (en) * | 2003-05-14 | 2003-06-18 | Btg Internat Limted | Treatment of neurodegenerative conditions |
| EP1622633B1 (en) | 2003-05-15 | 2016-02-24 | Ampio Pharmaceuticals, Inc. | Treatment of t-cell mediated diseases |
| WO2005018632A1 (en) * | 2003-08-18 | 2005-03-03 | Btg International Limited | Treatment of neurodegenerative conditions |
| DE10351111A1 (de) * | 2003-11-03 | 2005-06-16 | Langlotz, Rainer | Arzneimittel und Verfahren zu ihrer Herstellung |
| CA2554735A1 (en) * | 2004-01-30 | 2005-08-11 | Peplin Biolipids Pty Ltd | Therapeutic and carrier molecules |
| US7544714B2 (en) * | 2004-07-16 | 2009-06-09 | University Of Massachusetts | Lipid-amino acid conjugates and methods of use |
| GB0425932D0 (en) * | 2004-11-25 | 2004-12-29 | Btg Int Ltd | Structured phospholipids |
| GB0504362D0 (en) * | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Cytokine modulators |
| GB0504333D0 (en) * | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Treatment of cytokine dysregulation |
| US20060246115A1 (en) * | 2005-03-04 | 2006-11-02 | Ricardo Rueda | Nutritional products for ameliorating symptoms of rheumatoid arthritis |
| AU2006319216B2 (en) | 2005-11-29 | 2012-09-13 | Intrexon Actobiotics Nv | Induction of mucosal tolerance to antigens |
| CN103933563B (zh) | 2007-01-25 | 2016-09-28 | 英特瑞克斯顿阿克图比奥帝克斯有限公司 | 使用遗传修饰的乳杆菌通过抗原的粘膜递送治疗免疫疾病 |
| AU2008274876A1 (en) * | 2007-02-05 | 2009-01-15 | Children, Youth And Women's Health Service | Modulators of antigen-dependent T cell proliferation |
| JP5620272B2 (ja) | 2007-11-09 | 2014-11-05 | プロノヴァ・バイオファーマ・ノルゲ・アーエスＰｒｏｎｏｖａ ＢｉｏＰｈａｒｍａ ＮｏｒｇｅＡＳ | 化粧品において，食品サプリメントとして，または医薬品として用いるための脂質化合物 |
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Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK435087A (da) * | 1986-09-10 | 1988-03-11 | Hoffmann La Roche | Isoprenderivater |
| JPS6372648A (ja) * | 1986-09-16 | 1988-04-02 | Sumitomo Pharmaceut Co Ltd | 新規不飽和脂肪酸誘導体 |
| JPH02225411A (ja) * | 1989-02-28 | 1990-09-07 | Nippon Oil & Fats Co Ltd | 高度不飽和脂肪酸の溶血性低下方法 |
| US5202456A (en) * | 1991-04-15 | 1993-04-13 | The President And Fellows Of Harvard College | Compounds for inhibition of protein methylation |
| DE4120916A1 (de) * | 1991-06-25 | 1993-01-07 | Basf Ag | Omega-3 mehrfach ungesaettigte fettsaeurederivate, ihre herstellung und verwendung |
| NL9201438A (nl) * | 1992-08-11 | 1994-03-01 | Prospa Bv | Nieuwe farmaceutische samenstellingen die esters van omega-3 polyonverzadigde zuren omvatten en de toepassing ervan bij de plaatselijke behandeling van ziekelijke aandoeningen. |
| US5618955A (en) * | 1992-11-30 | 1997-04-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Fatty acid derivatives and pharmaceutical compositions containing same |
| WO1994022848A1 (en) * | 1993-03-29 | 1994-10-13 | Pace Asciak Cecil R | Hepoxilin analogs useful as anti-inflammatory agents |
| AUPM740594A0 (en) | 1994-08-11 | 1994-09-01 | J.W. Broadbent Nominees Pty. Ltd. | Anti-inflammatory preparation |
| AU3156595A (en) * | 1994-08-11 | 1996-03-07 | J.W. Broadbent Nominees Pty. Ltd. | Anti-inflammatory preparation |
| DE69524639T2 (de) | 1994-10-13 | 2002-08-08 | Peptech Ltd., North Ryde | Modifizierte mehrfach ungesättigte fettsäuren |
| AU698476B2 (en) * | 1994-10-13 | 1998-10-29 | Children, Youth And Women's Health Service Incorporated | Modified polyunsaturated fatty acids |
| AU686898B2 (en) * | 1994-10-26 | 1998-02-12 | Children, Youth And Women's Health Service Incorporated | Synthetic polyunsaturated fatty acid analogues |
| AUPM906594A0 (en) * | 1994-10-26 | 1994-11-17 | Peptide Technology Limited | Synthetic polyunsaturated fatty acid analogues |
| MY118354A (en) * | 1995-05-01 | 2004-10-30 | Scarista Ltd | 1,3-propane diol derivatives as bioactive compounds |
| US5585400A (en) * | 1996-02-27 | 1996-12-17 | Wisconsin Alumni Research Foundation | Methods of attenuating the allergic response in animals |
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- 1997-04-14 JP JP9536587A patent/JP2000508645A/ja active Pending
- 1997-04-14 EP EP97916266A patent/EP0904072A4/en not_active Ceased
- 1997-04-14 WO PCT/AU1997/000231 patent/WO1997038688A1/en not_active Ceased
- 1997-04-14 CA CA002251780A patent/CA2251780A1/en not_active Abandoned
- 1997-04-14 US US09/171,095 patent/US6262119B1/en not_active Expired - Fee Related
- 1997-04-14 GB GB9822203A patent/GB2328155B/en not_active Expired - Fee Related
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|---|---|---|---|---|
| US10823981B2 (en) | 2012-03-27 | 2020-11-03 | Adlens Ltd. | Deformable non-round membrane assemblies |
| JP2016500092A (ja) * | 2012-11-27 | 2016-01-07 | アヴェクシン エーエス | 皮膚炎治療 |
| US10085952B2 (en) | 2012-11-27 | 2018-10-02 | Avexxin As | Dermatitis treatment |
| US10758499B2 (en) | 2012-11-27 | 2020-09-01 | Avexxin As | Dermatitis treatment |
| US10953004B2 (en) | 2016-03-14 | 2021-03-23 | Avexxin As | Combination therapy for proliferative diseases |
| US11351127B2 (en) | 2016-09-21 | 2022-06-07 | Avexxin As | Pharmaceutical composition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0904072A1 (en) | 1999-03-31 |
| US6262119B1 (en) | 2001-07-17 |
| CA2251780A1 (en) | 1997-10-23 |
| GB2328155B (en) | 2000-08-02 |
| WO1997038688A1 (en) | 1997-10-23 |
| EP0904072A4 (en) | 2003-07-30 |
| GB9822203D0 (en) | 1998-12-02 |
| GB2328155A (en) | 1999-02-17 |
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