AU2002219348B2 - Autoinducer compounds and their uses - Google Patents
Autoinducer compounds and their uses Download PDFInfo
- Publication number
- AU2002219348B2 AU2002219348B2 AU2002219348A AU2002219348A AU2002219348B2 AU 2002219348 B2 AU2002219348 B2 AU 2002219348B2 AU 2002219348 A AU2002219348 A AU 2002219348A AU 2002219348 A AU2002219348 A AU 2002219348A AU 2002219348 B2 AU2002219348 B2 AU 2002219348B2
- Authority
- AU
- Australia
- Prior art keywords
- animal
- lactone
- autoinducer
- homoserine lactone
- acyl
- 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.)
- Ceased
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- 238000003306 harvesting Methods 0.000 description 1
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- YBTWUESFQWFDMR-UHFFFAOYSA-N methyl 3-hydroxypalmitate Chemical compound CCCCCCCCCCCCCC(O)CC(=O)OC YBTWUESFQWFDMR-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 235000020679 tap water Nutrition 0.000 description 1
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- 229950008166 valnemulin Drugs 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Mechanical Coupling Of Light Guides (AREA)
- Paper (AREA)
- Supplying Of Containers To The Packaging Station (AREA)
- Vehicle Body Suspensions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0100387A GB0100387D0 (en) | 2001-01-08 | 2001-01-08 | The application of quorum sensing signals to improve ruminant performance |
| GB0100387.0 | 2001-01-08 | ||
| GB0109477.0 | 2001-04-18 | ||
| GB0109477A GB0109477D0 (en) | 2001-04-18 | 2001-04-18 | The application of quorum sensing signals to improve animal performance |
| PCT/GB2002/000072 WO2002052949A1 (en) | 2001-01-08 | 2002-01-08 | Autoinducer compounds and their uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002219348A1 AU2002219348A1 (en) | 2003-01-23 |
| AU2002219348B2 true AU2002219348B2 (en) | 2006-11-16 |
Family
ID=26245534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002219348A Ceased AU2002219348B2 (en) | 2001-01-08 | 2002-01-08 | Autoinducer compounds and their uses |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7651699B2 (enExample) |
| EP (1) | EP1361801B1 (enExample) |
| JP (2) | JP4499355B2 (enExample) |
| AT (1) | ATE363839T1 (enExample) |
| AU (1) | AU2002219348B2 (enExample) |
| CA (1) | CA2434117C (enExample) |
| DE (1) | DE60220503T2 (enExample) |
| DK (1) | DK1361801T3 (enExample) |
| ES (1) | ES2288550T3 (enExample) |
| WO (1) | WO2002052949A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE523209C2 (sv) * | 2002-05-14 | 2004-04-06 | Akzo Nobel Nv | Förfarande för att reducera metanbildningen från matspjälkningsaktiviteter hos djur |
| SI1599461T1 (sl) | 2003-03-03 | 2009-10-31 | Eisai Corp Of North Amarica | Tiolaktoni kot inhibitorji NAALADaze |
| GB2418427A (en) | 2004-09-02 | 2006-03-29 | Univ Cambridge Tech | Ligands for G-protein coupled receptors |
| US7662967B2 (en) | 2007-08-02 | 2010-02-16 | Cambridge Enterprise Limited | Anti-inflammatory compounds and compositions |
| GB2452696B (en) * | 2007-08-02 | 2009-09-23 | Cambridge Entpr Ltd | 3-(2',2'-dimethylpropanoylamino)-tetrahydropyridin-2-one and its use in pharmaceutical compositions |
| CN104193091A (zh) * | 2009-06-22 | 2014-12-10 | 住友重机械工业株式会社 | 含氨态氮废水的处理方法 |
| US8624063B2 (en) | 2009-06-30 | 2014-01-07 | Wisconsin Alumni Research Foundation | Non-lactone carbocyclic and heterocyclic antagonists and agonists of bacterial quorum sensing |
| US8952192B2 (en) | 2011-03-24 | 2015-02-10 | University Of Maryland, College Park | Phosphorylated and branched dihydroxy-pentane-dione (DPD) analogs as quorum sensing inhibitors in bacteria |
| KR20170008850A (ko) | 2014-05-23 | 2017-01-24 | 피브로-애니멀 헬스 코포레이션 | 배합물, 조성물, 및 배합물 또는 조성물의 동물로의 투여 방법 |
| CN104206920A (zh) * | 2014-09-25 | 2014-12-17 | 冀照明 | 一种中草药羊饲料添加剂 |
| US10526278B2 (en) | 2017-10-19 | 2020-01-07 | Wisconsin Alumni Research Foundation | Inhibitors of quorum sensing receptor LasR |
| CN113930462A (zh) * | 2021-10-19 | 2022-01-14 | 江南大学 | 高丝氨酸内酯信号分子促进碳链延长微生物合成己酸的方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1205638A (en) * | 1966-09-29 | 1970-09-16 | Ciba Ltd | 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them |
| US4616016A (en) * | 1983-04-07 | 1986-10-07 | Basf Aktiengesellschaft | Mixtures which promote growth and increase production, and feeds and drinking liquids which contain small amounts of these mixtures |
| EP0479570A2 (en) * | 1990-10-05 | 1992-04-08 | Merck & Co. Inc. | Animal growth promotion with aromatase inhibitors |
| WO2002000035A1 (en) * | 2000-06-23 | 2002-01-03 | Acuabiotec Llc | Bioactive food complex, method for making bioactive food complex product and method for controlling disease |
| US6395282B1 (en) * | 1998-04-16 | 2002-05-28 | University Of Rochester | Immunogenic conjugates of Gram-negative bacterial autoinducer molecules |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4591872A (en) * | 1982-09-27 | 1986-05-27 | Power Science, Inc. | X-Y distinguishable multi-trace coding for multiparameter recording of a single stylus recorder |
| US4994379A (en) * | 1983-03-09 | 1991-02-19 | Cetus Corporation | Modified signal peptides |
| US4815016A (en) * | 1986-07-24 | 1989-03-21 | Unisys Corp. | High speed logical circuit simulator |
| NO882653D0 (no) * | 1988-06-15 | 1988-06-15 | Apothekernes Lab | Doseringsform. |
| GB9108307D0 (en) | 1991-04-18 | 1991-06-05 | Univ Nottingham | Autoinducer |
| WO1995001175A1 (en) * | 1993-07-02 | 1995-01-12 | The University Of Nottingham | Immunosuppressant and antiallergic compounds, e.g. n-(3-oxohexanoyl) homoserine lactone |
| US6936447B1 (en) * | 2000-04-03 | 2005-08-30 | University Of Iowa Research Foundation | Autoinducer molecule |
| US5591872A (en) * | 1993-08-09 | 1997-01-07 | The University Of Iowa Research Foundation | Autoinducer molecule |
| US5698246A (en) * | 1996-01-29 | 1997-12-16 | Cargill, Incorporated | Foodstuff for and method of feeding crustaceans and fish |
| WO1997027851A1 (en) | 1996-02-01 | 1997-08-07 | The Johns-Hopkins University | L-homoserine and l-homoserine lactone as bacteriostatic agents for m. tuberculosis and m. bovis |
| JP3865461B2 (ja) | 1997-06-16 | 2007-01-10 | 株式会社日立製作所 | Icカード読み書き装置 |
| EP0994961B1 (en) | 1997-06-18 | 2006-10-18 | Montana State University - Bozeman | Homoserine lactones biofilm regulating compounds and their methods of use |
| JP3834763B2 (ja) * | 1997-09-03 | 2006-10-18 | 岡部産業株式会社 | 混合飼料 |
| JPH11269142A (ja) | 1998-03-18 | 1999-10-05 | Toa Yakuhin Kogyo Kk | アゼチジン誘導体、それを有効成分とするビフィズス菌分裂促進組成物およびその製造方法 |
| US6337347B1 (en) * | 1998-06-18 | 2002-01-08 | The Research & Development Institute, Inc. | Autoinducer compounds |
| US6723321B2 (en) * | 1998-07-31 | 2004-04-20 | The Board Of Trustees Of The University Of Illinois | Autoinducer synthase modulating compounds and uses thereof |
| JP2000069985A (ja) | 1998-09-01 | 2000-03-07 | Basic Industries Bureau Miti | 細菌培養による化合物の製造方法及び植物生育促進剤 |
| GB0007588D0 (en) * | 2000-03-30 | 2000-05-17 | Univ Nottingham | N-Acyl homoserine lactones |
| US20030078231A1 (en) * | 2001-06-22 | 2003-04-24 | Wilburn Michael D. | Orthomolecular sulpho-adenosylmethionine derivatives with antioxidant properties |
-
2002
- 2002-01-08 AT AT02727000T patent/ATE363839T1/de not_active IP Right Cessation
- 2002-01-08 US US10/250,842 patent/US7651699B2/en not_active Expired - Fee Related
- 2002-01-08 CA CA2434117A patent/CA2434117C/en not_active Expired - Fee Related
- 2002-01-08 EP EP02727000A patent/EP1361801B1/en not_active Expired - Lifetime
- 2002-01-08 JP JP2002553913A patent/JP4499355B2/ja not_active Expired - Fee Related
- 2002-01-08 ES ES02727000T patent/ES2288550T3/es not_active Expired - Lifetime
- 2002-01-08 AU AU2002219348A patent/AU2002219348B2/en not_active Ceased
- 2002-01-08 DE DE60220503T patent/DE60220503T2/de not_active Expired - Lifetime
- 2002-01-08 WO PCT/GB2002/000072 patent/WO2002052949A1/en not_active Ceased
- 2002-01-08 DK DK02727000T patent/DK1361801T3/da active
-
2007
- 2007-12-19 JP JP2007327905A patent/JP2008079623A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1205638A (en) * | 1966-09-29 | 1970-09-16 | Ciba Ltd | 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them |
| US4616016A (en) * | 1983-04-07 | 1986-10-07 | Basf Aktiengesellschaft | Mixtures which promote growth and increase production, and feeds and drinking liquids which contain small amounts of these mixtures |
| EP0479570A2 (en) * | 1990-10-05 | 1992-04-08 | Merck & Co. Inc. | Animal growth promotion with aromatase inhibitors |
| US6395282B1 (en) * | 1998-04-16 | 2002-05-28 | University Of Rochester | Immunogenic conjugates of Gram-negative bacterial autoinducer molecules |
| WO2002000035A1 (en) * | 2000-06-23 | 2002-01-03 | Acuabiotec Llc | Bioactive food complex, method for making bioactive food complex product and method for controlling disease |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60220503D1 (de) | 2007-07-19 |
| DK1361801T3 (da) | 2007-10-08 |
| DE60220503T2 (de) | 2008-01-31 |
| EP1361801A1 (en) | 2003-11-19 |
| ES2288550T3 (es) | 2008-01-16 |
| EP1361801B1 (en) | 2007-06-06 |
| US7651699B2 (en) | 2010-01-26 |
| JP2004525617A (ja) | 2004-08-26 |
| JP4499355B2 (ja) | 2010-07-07 |
| JP2008079623A (ja) | 2008-04-10 |
| WO2002052949A1 (en) | 2002-07-11 |
| CA2434117A1 (en) | 2002-07-11 |
| CA2434117C (en) | 2011-03-01 |
| US20040115245A1 (en) | 2004-06-17 |
| ATE363839T1 (de) | 2007-06-15 |
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|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: PATHWAY INTERMEDIATES LTD Free format text: FORMER OWNER WAS: GORMAR MARKETING LIMITED |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |