CA2693051A1 - Composes a base de lanthibiotique a activite antimicrobienne - Google Patents
Composes a base de lanthibiotique a activite antimicrobienne Download PDFInfo
- Publication number
- CA2693051A1 CA2693051A1 CA 2693051 CA2693051A CA2693051A1 CA 2693051 A1 CA2693051 A1 CA 2693051A1 CA 2693051 CA2693051 CA 2693051 CA 2693051 A CA2693051 A CA 2693051A CA 2693051 A1 CA2693051 A1 CA 2693051A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- monocarboxamide
- group
- deoxyactagardine
- actagardine
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 283
- 108010062877 Bacteriocins Proteins 0.000 title description 58
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 102
- 108010053762 deoxyactagardine B Proteins 0.000 claims abstract description 92
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- 108010070411 gardimycin Proteins 0.000 claims abstract description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 46
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- 125000000539 amino acid group Chemical group 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
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- 238000011282 treatment Methods 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
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- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 claims description 2
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- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 claims description 2
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- KHVCOYGKHDJPBZ-WDCZJNDASA-N tetrahydrooxazine Chemical compound OC[C@H]1ONC[C@@H](O)[C@@H]1O KHVCOYGKHDJPBZ-WDCZJNDASA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
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- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- BQAJJINKFRRSFO-UHFFFAOYSA-N thiolane Chemical compound C1CCSC1.C1CCSC1 BQAJJINKFRRSFO-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000001551 total correlation spectroscopy Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/195—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria
- C07K14/365—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria from Actinoplanes (G)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0714029.6A GB0714029D0 (en) | 2007-07-18 | 2007-07-18 | Lantibiotic-based compounds having antimicrobial activity |
| GB0714029.6 | 2007-07-18 | ||
| PCT/GB2008/002465 WO2009010765A2 (fr) | 2007-07-18 | 2008-07-18 | Composes a base de lanthibiotique a activite antimicrobienne |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2693051A1 true CA2693051A1 (fr) | 2009-01-22 |
Family
ID=38476566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2693051 Abandoned CA2693051A1 (fr) | 2007-07-18 | 2008-07-18 | Composes a base de lanthibiotique a activite antimicrobienne |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8329644B2 (fr) |
| EP (1) | EP2167527A2 (fr) |
| JP (1) | JP5389023B2 (fr) |
| KR (1) | KR20100044849A (fr) |
| CN (1) | CN101796067A (fr) |
| AU (1) | AU2008277422A1 (fr) |
| BR (1) | BRPI0814555A2 (fr) |
| CA (1) | CA2693051A1 (fr) |
| EA (1) | EA018841B1 (fr) |
| GB (1) | GB0714029D0 (fr) |
| IL (1) | IL202620A0 (fr) |
| NZ (1) | NZ581885A (fr) |
| WO (1) | WO2009010765A2 (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0600928D0 (en) | 2006-01-17 | 2006-02-22 | Novacta Biosystems Ltd | Improvements relating to lantibiotics |
| GB0714030D0 (en) | 2007-07-18 | 2007-08-29 | Novacta Biosystems Ltd | The use of type-B lantibiotic-based compounds having antimicrobial activity |
| GB0714029D0 (en) | 2007-07-18 | 2007-08-29 | Novacta Biosystems Ltd | Lantibiotic-based compounds having antimicrobial activity |
| GB0900599D0 (en) * | 2009-01-14 | 2009-02-18 | Novacta Biosystems Ltd | Treatment |
| PL2387580T3 (pl) | 2009-01-14 | 2015-01-30 | Novacta Biosystems Ltd | Pochodne deoksyaktagardyny |
| EP2393829A1 (fr) * | 2009-02-04 | 2011-12-14 | Novacta Biosystems Limited | Dérivés d'actagardine |
| GB201001688D0 (en) * | 2010-02-02 | 2010-03-17 | Novacta Biosystems Ltd | Compounds |
| JP5852966B2 (ja) * | 2010-02-02 | 2016-02-03 | ノヴァクタ バイオシステムズ リミティッド | ランチビオティックの塩 |
| CA2804697A1 (fr) * | 2010-07-14 | 2012-01-19 | Novacta Biosystems Limited | Formulation comprenant un lantibiotique de type b |
| GB201013509D0 (en) * | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Compounds |
| GB201013508D0 (en) * | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Compounds |
| GB201013513D0 (en) * | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Formulations |
| GB201013507D0 (en) * | 2010-08-11 | 2010-09-22 | Novacta Biosystems Ltd | Compounds |
| US20140094402A1 (en) * | 2011-03-30 | 2014-04-03 | Sentinella Pharmaceuticals, Inc. | Lantibiotic NAI-802, Pharmaceutically Acceptable Salts, Compositions and Uses Thereof |
| GB201213434D0 (en) * | 2012-07-27 | 2012-09-12 | Novacta Biosystems Ltd | The use of type-B lantibiotic-based compounds having antimicrobial activity |
| US9975930B2 (en) | 2012-11-30 | 2018-05-22 | Naicons S.R.L. | Lantibiotic derivatives and process for their preparation |
| WO2014193237A2 (fr) * | 2013-05-30 | 2014-12-04 | Academisch Ziekenhuis Leiden H.O.D.N. Lumc | Protéase de c. difficile |
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| US3710795A (en) * | 1970-09-29 | 1973-01-16 | Alza Corp | Drug-delivery device with stretched, rate-controlling membrane |
| GB8507528D0 (en) | 1985-03-22 | 1985-05-01 | Lepetit Spa | Basis monocarboxyamide derivatives |
| US5304540A (en) | 1988-06-22 | 1994-04-19 | Applied Microbiology, Inc. | Pharmaceutical bacteriocin compositions and methods for using the same |
| IN167138B (fr) * | 1988-08-17 | 1990-09-01 | Hoechst India | |
| GB8926639D0 (en) | 1989-11-24 | 1990-01-17 | Agricultural & Food Res | Delayed release formulations |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| IT1260505B (it) | 1992-06-01 | 1996-04-09 | Poli Ind Chimica Spa | Sistemi farmaceutici orali a cessione ritardata per il rilascio specifico nel colon |
| IL107887A (en) * | 1992-12-08 | 2003-07-06 | Ambi Inc | Stabilized lanthionine containing bacteriocin compositions |
| US5512269A (en) | 1993-06-09 | 1996-04-30 | Burroughs Wellcome, Co. | Method of treating retained pulmonary secretions |
| EP0700998B1 (fr) | 1994-09-12 | 2003-11-26 | Aventis Pharma Deutschland GmbH | Mersacidine recombinante et méthode de production |
| SK285563B6 (sk) | 1995-06-23 | 2007-03-01 | Ambi, Inc. | Použitie lanthocinu na výrobu liečiva na liečenieinfekcie |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| US5958873A (en) | 1997-06-09 | 1999-09-28 | University Of Cincinnati | Oral formulation for treatment of bacteria-induced diseases of the colon |
| US5985823A (en) * | 1997-06-09 | 1999-11-16 | Ambi Inc. | Method for the treatment of diarrheal disease and for eliminating particular bacterial populations from the colon |
| DE19745583A1 (de) * | 1997-10-15 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Neues Lantibiotikum verwandt mit Actagardine, Verfahren zur Herstellung und Verwendung derselben |
| US6569830B1 (en) * | 1999-03-05 | 2003-05-27 | Ambi, Inc. | Compositions and methods for treatment of staphylococcal infection while suppressing formation of antibiotic-resistant strains |
| MXPA03000051A (es) | 2000-06-28 | 2003-08-19 | Smithkline Beecham Plc | Procedimiento de molido en humedo. |
| GB0110432D0 (en) | 2001-04-27 | 2001-06-20 | Plant Bioscience Ltd | Lantibiotic production |
| WO2002103010A1 (fr) | 2001-06-14 | 2002-12-27 | Plant Bioscience Limited | Methodes et materiels destines a la disruption ciblee de genes dans des actinomycetes |
| US6861236B2 (en) | 2002-05-24 | 2005-03-01 | Applied Nanosystems B.V. | Export and modification of (poly)peptides in the lantibiotic way |
| JP2006502713A (ja) | 2002-10-10 | 2006-01-26 | モリケム メディシンズ， インコーポレイテッド | デュラマイシンをコードする核酸 |
| JP4163737B2 (ja) | 2003-07-18 | 2008-10-08 | ヴァイキュロン ファーマシューティカルズ， インコーポレイテッド | 抗生物質１０７８９１、そのａ１因子とａ２因子、その薬剤学的に許容される塩、組成物、およびその使用 |
| US7351687B2 (en) | 2003-07-18 | 2008-04-01 | Vicuron Pharmaceuticals, Inc. | Antibiotic 107891, its factors A1 and A2, pharmaceutically acceptable salts and compositions, and use thereof |
| GB0406870D0 (en) | 2004-03-26 | 2004-04-28 | Novacta Biosystems Ltd | Improvements relating to the production of lantibiotics |
| EP1928900A1 (fr) | 2005-09-27 | 2008-06-11 | Novacta Biosystems Limited | Variantes du lantibiotique mersacidine, et leur utilisation |
| GB0600928D0 (en) | 2006-01-17 | 2006-02-22 | Novacta Biosystems Ltd | Improvements relating to lantibiotics |
| CA2667167C (fr) | 2006-10-27 | 2014-02-18 | Pfizer Products Inc. | Capsules dures en hydroxypropylmethylcellulose et leur procede de fabrication |
| CA2690267A1 (fr) | 2007-06-12 | 2008-12-18 | The University Of British Columbia | Petits peptides cationiques antimicrobiens |
| GB0714030D0 (en) | 2007-07-18 | 2007-08-29 | Novacta Biosystems Ltd | The use of type-B lantibiotic-based compounds having antimicrobial activity |
| GB0714029D0 (en) | 2007-07-18 | 2007-08-29 | Novacta Biosystems Ltd | Lantibiotic-based compounds having antimicrobial activity |
| RU2506272C2 (ru) | 2008-11-24 | 2014-02-10 | Сентинелла Фармасьютикалз, Инк. ("Сентинелла") | Лантибиотические карбоксиамидные производные с усиленной антибактериальной активностью |
| PL2387580T3 (pl) | 2009-01-14 | 2015-01-30 | Novacta Biosystems Ltd | Pochodne deoksyaktagardyny |
| GB0900599D0 (en) | 2009-01-14 | 2009-02-18 | Novacta Biosystems Ltd | Treatment |
| EP2393829A1 (fr) | 2009-02-04 | 2011-12-14 | Novacta Biosystems Limited | Dérivés d'actagardine |
-
2007
- 2007-07-18 GB GBGB0714029.6A patent/GB0714029D0/en not_active Ceased
-
2008
- 2008-07-18 EA EA200971101A patent/EA018841B1/ru not_active IP Right Cessation
- 2008-07-18 EP EP08775990A patent/EP2167527A2/fr not_active Withdrawn
- 2008-07-18 CN CN200880024962A patent/CN101796067A/zh active Pending
- 2008-07-18 KR KR1020107003251A patent/KR20100044849A/ko not_active Application Discontinuation
- 2008-07-18 CA CA 2693051 patent/CA2693051A1/fr not_active Abandoned
- 2008-07-18 US US12/669,432 patent/US8329644B2/en not_active Expired - Fee Related
- 2008-07-18 AU AU2008277422A patent/AU2008277422A1/en not_active Abandoned
- 2008-07-18 BR BRPI0814555-5A2A patent/BRPI0814555A2/pt active Search and Examination
- 2008-07-18 JP JP2010516583A patent/JP5389023B2/ja not_active Expired - Fee Related
- 2008-07-18 WO PCT/GB2008/002465 patent/WO2009010765A2/fr active Application Filing
- 2008-07-18 NZ NZ581885A patent/NZ581885A/en not_active IP Right Cessation
-
2009
- 2009-12-09 IL IL202620A patent/IL202620A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA200971101A1 (ru) | 2010-08-30 |
| EP2167527A2 (fr) | 2010-03-31 |
| GB0714029D0 (en) | 2007-08-29 |
| JP2010533696A (ja) | 2010-10-28 |
| JP5389023B2 (ja) | 2014-01-15 |
| US8329644B2 (en) | 2012-12-11 |
| CN101796067A (zh) | 2010-08-04 |
| US20100261638A1 (en) | 2010-10-14 |
| EA018841B1 (ru) | 2013-11-29 |
| WO2009010765A2 (fr) | 2009-01-22 |
| KR20100044849A (ko) | 2010-04-30 |
| IL202620A0 (en) | 2010-06-30 |
| BRPI0814555A2 (pt) | 2015-01-06 |
| WO2009010765A3 (fr) | 2009-04-23 |
| NZ581885A (en) | 2012-03-30 |
| AU2008277422A1 (en) | 2009-01-22 |
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| FZDE | Discontinued |
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