WO2001074801A1 - Immunosuppressant n-acyles homoserine lactones - Google Patents
Immunosuppressant n-acyles homoserine lactones Download PDFInfo
- Publication number
- WO2001074801A1 WO2001074801A1 PCT/GB2001/001435 GB0101435W WO0174801A1 WO 2001074801 A1 WO2001074801 A1 WO 2001074801A1 GB 0101435 W GB0101435 W GB 0101435W WO 0174801 A1 WO0174801 A1 WO 0174801A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- tetradecenoyl
- enantiomer
- compound according
- animal body
- Prior art date
Links
- 230000001861 immunosuppressant effect Effects 0.000 title claims abstract 3
- 229960003444 immunosuppressant agent Drugs 0.000 title claims 3
- 239000003018 immunosuppressive agent Substances 0.000 title claims 3
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 title abstract 2
- -1 piperazino group Chemical group 0.000 claims abstract 27
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 241001465754 Metazoa Species 0.000 claims abstract 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 4
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 125000000468 ketone group Chemical group 0.000 claims abstract 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 2
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- QJPWUUJVYOJNMH-VKHMYHEASA-N L-homoserine lactone Chemical compound N[C@H]1CCOC1=O QJPWUUJVYOJNMH-VKHMYHEASA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 abstract 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 abstract 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 210000004698 lymphocyte Anatomy 0.000 abstract 1
- 210000002540 macrophage Anatomy 0.000 abstract 1
- 210000001616 monocyte Anatomy 0.000 abstract 1
- 230000035755 proliferation Effects 0.000 abstract 1
- 230000028327 secretion Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Transplantation (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
New N-acyl homoserine lactone compounds of the formula (I) in whichR is an acyl group of the formula (II) wherein one of R?1 and R2¿ is H and the other is selected from OR4, SR4 and NHR4, wherein R4 is H or 1-6C alkyl, or R?1 and R2¿ together with the carbon atom to which they are joined form a keto group, and R3 is a straight or branched chain, saturated or unsaturated aliphatic hydrocarbyl group containing from 8 to 11 carbon atoms and is optionally substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl, carbamoyl optionally mono- or disubstituted at the N atom by 1-6C alkyl and NR5R6 wherein each of R?5 and R6¿ is selected from H and 1-6C alkyl or R?5 and R6¿ together with the N atom form a morpholino or piperazino group, or any enantiomer thereof, with the proviso that R is not a 3-oxododecanoyl group, having immunosuppressant properties are disclosed. The compounds are shown to have an inhibitory effect on lymphocyte proliferation and down-regulate TNF-α secretion by monocytes/macrophages in the animal body, including the human body. Pharmaceutical compositions comprising N-acyl homoserine lactones are also described.
Claims
1. A compound of the formula
in which R is an acyl group of the formula II
wherein one of R1 and R2 is H and the other is selected from OR4, SR4 and NHR4, wherein R4 is H or 1-6C alkyl, or R1 and R2 together with the carbon atom to which they are joined form a keto group, and R3 is a straight or branched chain, saturated or unsaturated aliphatic hydrocarbyl group containing from 8 to 11 carbon atoms and is optionally substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl, carbamoyl optionally mono- or disubstituted at the N atom by 1-6C alkyl and NR5R6 wherein each of R5 and R6 is selected from H and 1-6C alkyl or R5 and R6 together with the N atom form a morpholino or piperazino group, or any enantiomer thereof, with the proviso that R is not a 3-oxododecanoyl group.
2. A compound according to claim 1 , wherein the R group is selected from
and o o
RJ -CH,
wherein R3 is as defined in claim 1.
3. A compound according to either claim 1 or claim 2, wherein the group R3 is an 8-11C straight or branched chain alkyl group optionally substituted by a substituent selected from bromo, carboxy and methoxycarbonyl.
4. A compound according to claim 3, wherein the R3 group is such that the group R in formula I is selected from;
3-oxoundecanoyl;
11-bromo-3-oxoundecanoyl;
10-methyl-3-oxoundecanoyl;
6-methyl-3-oxoundecanoyl;
3-hydroxydodecanoyl;
12-bromo-3-oxododecanoyl;
3-oxotridecanoyl;
13-bromo-3-oxotridecanoyl;
3-hydroxytetradecanoyl;
3-oxotetradecanoyl;
14-bromo-3-oxotetradecanoyl; and
13-methoxycarbonyl-3-oxotridecanoyl.
5. A compound according to either claim 1 or claim 2, wherein the group R3 is an 8-11C straight or branched chain alkenyl group optionally substituted by a substituent selected from bromo, carboxy and methoxycarbonyl.
6. A compound according to claim 5, wherein the R3 group is such that the group R in formula I is selected from; 26
3-oxo-l 2-tridecenoyl; 3-oxo-7-tetradecenoyl 3-hydroxy-7-tetradecenoyl; 3-oxo-9-tetradecenoyl; 3-hydroxy-9-tetradecenoyl; 3-oxo-10-tetradecenoyl; 3-hydroxy-10-tetradecenoyl; 3-oxo-l 1 -tetradecenoyl; 3-hydroxy-11-tetradecenoyl; 3-oxo-13-tetradecenoyl; and 3-hydroxy-13-tetradecenoyl.
7. A pharmaceutical composition comprising a therapeutically-effective amount of a compound of any one of claims 1 to 6, or an enantiomer thereof, together with at least one pharmaceutically-acceptable carrier or diluent.
8. The use of a compound according to any one of claims 1 to 6, or an enantiomer thereof, for the manufacture of a medicament for the treatment of a disease of a living animal body, including a human, which disease is responsive to the activity of an immunosuppressant.
9. The use of a compound according to any one of claims 1 to 6, or an enantiomer thereof, for the treatment of an autoimmune disease in a living animal body, including a human.
10. The use according to claim 9, wherein the autoimmune disease is selected from psoriasis, multiple sclerosis and rheumatoid arthritis.
11. A method of treating a disease of a living animal body, including a human, which disease is responsive to the activity of immunosuppressants which method comprises administering to the living animal body, including a 27
human, a therapeutically-effective amount of a compound according to any one of claims 1 to 6 or an enantiomer thereof.
12. The use of Λ/-(3-oxododecanoyl)homoserine lactone, including an enantiomer thereof, for the manufacture of a medicament for the treatment of psoriasis in a living animal body, including human.
13. A method of treating psoriasis in a living animal body, including human, which method comprises administering to the living animal body, including human, a therapeutically-effective amount of Λ/-(3- oxododecanoyl)homosehne lactone or an enantiomer thereof.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/240,237 US20030171371A1 (en) | 2000-03-30 | 2001-03-29 | Immunosuppressant n-acyles homoserine lactones |
| AU2001248504A AU2001248504A1 (en) | 2000-03-30 | 2001-03-29 | Immunosuppressant n-acyles homoserine lactones |
| EP01921527A EP1268459A1 (en) | 2000-03-30 | 2001-03-29 | Immunosuppressant n-acyl homoserine lactones |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0007588.7A GB0007588D0 (en) | 2000-03-30 | 2000-03-30 | N-Acyl homoserine lactones |
| GB0007588.7 | 2000-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2001074801A1 true WO2001074801A1 (en) | 2001-10-11 |
Family
ID=9888642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB2001/001435 WO2001074801A1 (en) | 2000-03-30 | 2001-03-29 | Immunosuppressant n-acyles homoserine lactones |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20030171371A1 (en) |
| EP (1) | EP1268459A1 (en) |
| AU (1) | AU2001248504A1 (en) |
| GB (1) | GB0007588D0 (en) |
| WO (1) | WO2001074801A1 (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002052949A1 (en) * | 2001-01-08 | 2002-07-11 | Gormar Marketing Limited | Autoinducer compounds and their uses |
| WO2003004017A1 (en) * | 2001-07-04 | 2003-01-16 | The University Of Nottingham | Synergistic compositions of n-acylhomoserine lactones and 4-quinolones |
| WO2003022828A1 (en) * | 2001-09-12 | 2003-03-20 | The University Of Nottingham | Use of n-acyl homoserine lactones for the treatment of insulitis |
| EP1299118A2 (en) * | 2000-06-02 | 2003-04-09 | K-Quay Enterprises, LLC | Production and use of derivatized homoserine lactones |
| EP1442742A1 (en) * | 2003-01-29 | 2004-08-04 | Nobuhiko Nomura | Apoptosis inducer and method of screening for a substance inhibiting acylated homoserine lactone |
| WO2007135466A2 (en) * | 2006-05-22 | 2007-11-29 | The Secretary Of State For Defence | Substituted n-acyl homoserine lactones |
| KR100841294B1 (en) | 2006-12-04 | 2008-06-25 | 재단법인서울대학교산학협력재단 | Homoserine lactone derivative for a quorum sensing antagonist and method of preventing a biofilm formation |
| EP2261260A2 (en) | 2004-03-27 | 2010-12-15 | Haptogen Ltd | Methods for inducing autolysis in infectious bacteria |
| EP2260868A2 (en) | 2002-08-13 | 2010-12-15 | Haptogen Ltd | Methods for the treatment of an infectious bacterial disease with anti-lactone or lactone derived signal molecules antibody |
| WO2011001419A1 (en) * | 2009-07-03 | 2011-01-06 | National Institute For Biotechnology In The Negev | Covalent inhibition of bacterial quorum sensing |
| EP2281839A2 (en) | 2004-05-15 | 2011-02-09 | Haptogen Ltd | Methods for reducing biofilm formation in infectious bacteria |
| WO2014201507A1 (en) * | 2013-06-21 | 2014-12-24 | Technological Resources Pty. Limited | Homoserine lactone derivatives for improving elemental recovery during biomining |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI594991B (en) * | 2015-06-30 | 2017-08-11 | 中央研究院 | Novel glucagon-like peptide 1 modulator and uses thereof |
| WO2017058757A1 (en) * | 2015-10-01 | 2017-04-06 | The University Of Toledo | Use of acyl-homoserine lactone derivatives as anti-thrombotic agents |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0094233A1 (en) * | 1982-05-11 | 1983-11-16 | Scripps Clinic And Research Foundation | Immune modulator peptides |
| WO1992018614A1 (en) * | 1991-04-18 | 1992-10-29 | The University Of 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 |
| US5591872A (en) * | 1993-08-09 | 1997-01-07 | The University Of Iowa Research Foundation | Autoinducer molecule |
| WO1998058075A2 (en) * | 1997-06-18 | 1998-12-23 | The Research And Development Institute, Inc. | Homoserine lactones biofilm regulating compounds and their methods of use |
| WO1999027786A1 (en) * | 1997-12-04 | 1999-06-10 | The University Of Nottingham | Control of biofilm formation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6395282B1 (en) * | 1998-04-16 | 2002-05-28 | University Of Rochester | Immunogenic conjugates of Gram-negative bacterial autoinducer molecules |
| US6337347B1 (en) * | 1998-06-18 | 2002-01-08 | The Research & Development Institute, Inc. | Autoinducer compounds |
-
2000
- 2000-03-30 GB GBGB0007588.7A patent/GB0007588D0/en not_active Ceased
-
2001
- 2001-03-29 AU AU2001248504A patent/AU2001248504A1/en not_active Abandoned
- 2001-03-29 WO PCT/GB2001/001435 patent/WO2001074801A1/en not_active Application Discontinuation
- 2001-03-29 US US10/240,237 patent/US20030171371A1/en not_active Abandoned
- 2001-03-29 EP EP01921527A patent/EP1268459A1/en not_active Withdrawn
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0094233A1 (en) * | 1982-05-11 | 1983-11-16 | Scripps Clinic And Research Foundation | Immune modulator peptides |
| WO1992018614A1 (en) * | 1991-04-18 | 1992-10-29 | The University Of 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 |
| US5591872A (en) * | 1993-08-09 | 1997-01-07 | The University Of Iowa Research Foundation | Autoinducer molecule |
| WO1998058075A2 (en) * | 1997-06-18 | 1998-12-23 | The Research And Development Institute, Inc. | Homoserine lactones biofilm regulating compounds and their methods of use |
| WO1999027786A1 (en) * | 1997-12-04 | 1999-06-10 | The University Of Nottingham | Control of biofilm formation |
Non-Patent Citations (4)
| Title |
|---|
| CHHABRA,S.R. ET AL.: "Autoregulation of Carbapenem Biosyntesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl)-L-Homserine Lactone", J.ANTIBIOT., vol. 46, no. 3, March 1993 (1993-03-01), pages 441 - 454, XP002171280 * |
| EBERHARD A ET AL: "ANALOGS OF THE AUTOINDUCER OF BIOLUMINESCENCE IN VIBRIO FISCHERI", ARCHIVES OF MICROBIOLOGY,DE,BERLIN, vol. 146, no. 1, 1986, pages 35 - 40, XP000884126, ISSN: 0302-8933 * |
| TELFORD,G. ET AL.: "The Pseudomonas aeruginosa Quorum-Sensing signal Molecule N-(3-oxododecanoyl)-L-Homserine Lactone Has Immunomodulatory Activity", INFECTION AND IMMUNITY, vol. 66, no. 1, January 1998 (1998-01-01), pages 36 - 42, XP002171279 * |
| ZHU J ET AL: "ANALOGS OF THE AUTOINDUCER 3-OXOOCTANOYL-HOMOSERINE LACTONE STRONGLY INHIBIT ACTIVITY OF THE TRAR PROTEIN OF AGROBACTERIUM TUMEFACIENS", JOURNAL OF BACTERIOLOGY,WASHINGTON, DC,US, vol. 180, no. 20, October 1998 (1998-10-01), pages 5398 - 5405, XP000884118, ISSN: 0021-9193 * |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7560572B2 (en) | 2000-06-02 | 2009-07-14 | K-Quay Enterprises, Llc | Production and use of derivatized homoserine lactones |
| EP1299118A2 (en) * | 2000-06-02 | 2003-04-09 | K-Quay Enterprises, LLC | Production and use of derivatized homoserine lactones |
| EP1299118A4 (en) * | 2000-06-02 | 2007-08-15 | Quay Entpr Llc K | Production and use of derivatized homoserine lactones |
| WO2002052949A1 (en) * | 2001-01-08 | 2002-07-11 | Gormar Marketing Limited | Autoinducer compounds and their uses |
| US7651699B2 (en) | 2001-01-08 | 2010-01-26 | Pathway Intermediates Limited | Autoinducer compounds and their uses |
| WO2003004017A1 (en) * | 2001-07-04 | 2003-01-16 | The University Of Nottingham | Synergistic compositions of n-acylhomoserine lactones and 4-quinolones |
| US7371779B2 (en) | 2001-07-04 | 2008-05-13 | The Secretary Of State For Defense Science And Technology | Synergistic compositions of N-acylhomoserine lactones and 4-quinolones |
| WO2003022828A1 (en) * | 2001-09-12 | 2003-03-20 | The University Of Nottingham | Use of n-acyl homoserine lactones for the treatment of insulitis |
| EP2260868A2 (en) | 2002-08-13 | 2010-12-15 | Haptogen Ltd | Methods for the treatment of an infectious bacterial disease with anti-lactone or lactone derived signal molecules antibody |
| EP1442742A1 (en) * | 2003-01-29 | 2004-08-04 | Nobuhiko Nomura | Apoptosis inducer and method of screening for a substance inhibiting acylated homoserine lactone |
| US7537906B2 (en) | 2003-01-29 | 2009-05-26 | Nobuhiko Nomura | Apoptosis inducer and method of screening for a substance inhibiting acylated homoserine lactone |
| EP2261260A2 (en) | 2004-03-27 | 2010-12-15 | Haptogen Ltd | Methods for inducing autolysis in infectious bacteria |
| EP2281839A2 (en) | 2004-05-15 | 2011-02-09 | Haptogen Ltd | Methods for reducing biofilm formation in infectious bacteria |
| US8049020B2 (en) | 2006-05-22 | 2011-11-01 | The Secretary Of State For Defence | Substituted N -acyl homoserine lactones |
| GB2452436A (en) * | 2006-05-22 | 2009-03-04 | Secr Defence | Substituted N-Acyl homoserine lactones |
| WO2007135466A3 (en) * | 2006-05-22 | 2008-01-10 | Sec Dep For Defence As Represe | Substituted n-acyl homoserine lactones |
| WO2007135466A2 (en) * | 2006-05-22 | 2007-11-29 | The Secretary Of State For Defence | Substituted n-acyl homoserine lactones |
| JP2009537625A (en) * | 2006-05-22 | 2009-10-29 | ザ セクレタリー オブ ステイト フォー ディフェンス | Substituted N-acyl homoserine lactone |
| KR100841294B1 (en) | 2006-12-04 | 2008-06-25 | 재단법인서울대학교산학협력재단 | Homoserine lactone derivative for a quorum sensing antagonist and method of preventing a biofilm formation |
| WO2011001419A1 (en) * | 2009-07-03 | 2011-01-06 | National Institute For Biotechnology In The Negev | Covalent inhibition of bacterial quorum sensing |
| CN102482244A (en) * | 2009-07-03 | 2012-05-30 | 内盖夫国家生物技术有限公司 | Covalent inhibition of bacterial quorum sensing |
| JP2012532095A (en) * | 2009-07-03 | 2012-12-13 | ザ ナショナル インスティテュート フォー バイオテクノロジー イン ザ ネゲヴ リミテッド | Covalent inhibition of bacterial quorum sensing |
| US8501969B2 (en) | 2009-07-03 | 2013-08-06 | The National Institute for Biotechnology in the Negev Ltd. | Covalent inhibition of bacterial quorum sensing |
| CN102482244B (en) * | 2009-07-03 | 2015-09-09 | 内盖夫国家生物技术有限公司 | The covalency of bacterial population induction suppresses |
| US9242951B2 (en) | 2009-07-03 | 2016-01-26 | The National Institute for Biotechnology in the Negev Ltd. | Covalent inhibition of bacterial quorum sensing |
| WO2014201507A1 (en) * | 2013-06-21 | 2014-12-24 | Technological Resources Pty. Limited | Homoserine lactone derivatives for improving elemental recovery during biomining |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030171371A1 (en) | 2003-09-11 |
| EP1268459A1 (en) | 2003-01-02 |
| AU2001248504A1 (en) | 2001-10-15 |
| GB0007588D0 (en) | 2000-05-17 |
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