CA2599336A1 - Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity - Google Patents
Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity Download PDFInfo
- Publication number
- CA2599336A1 CA2599336A1 CA002599336A CA2599336A CA2599336A1 CA 2599336 A1 CA2599336 A1 CA 2599336A1 CA 002599336 A CA002599336 A CA 002599336A CA 2599336 A CA2599336 A CA 2599336A CA 2599336 A1 CA2599336 A1 CA 2599336A1
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- Prior art keywords
- substituted
- group
- alkyl
- aryl
- heteroaryl
- Prior art date
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- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 title claims abstract description 17
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 title claims abstract description 16
- 108010059993 Vancomycin Proteins 0.000 title claims abstract description 15
- 229960003165 vancomycin Drugs 0.000 title claims abstract description 15
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- 102000002068 Glycopeptides Human genes 0.000 title abstract description 21
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- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 3
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
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- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65763605P | 2005-02-28 | 2005-02-28 | |
| US60/657,636 | 2005-02-28 | ||
| PCT/US2006/007021 WO2006093933A2 (en) | 2005-02-28 | 2006-02-27 | Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2599336A1 true CA2599336A1 (en) | 2006-09-08 |
Family
ID=36941722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002599336A Abandoned CA2599336A1 (en) | 2005-02-28 | 2006-02-27 | Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7368422B2 (enExample) |
| EP (1) | EP1858908A4 (enExample) |
| JP (2) | JP2008531701A (enExample) |
| AU (1) | AU2006218743A1 (enExample) |
| BR (1) | BRPI0607701A2 (enExample) |
| CA (1) | CA2599336A1 (enExample) |
| WO (1) | WO2006093933A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2588285A1 (en) | 2004-11-29 | 2006-06-01 | National University Corporation Nagoya University | Glycopeptide antibiotic monomer derivatives |
| US7632918B2 (en) * | 2005-02-28 | 2009-12-15 | Novartis Vaccines And Diagnostics, Inc. | Semi-synthetic glycopeptides with antibiotic activity |
| US7368422B2 (en) * | 2005-02-28 | 2008-05-06 | Novartis Vaccines And Diagnostics Inc. | Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| US20070185015A1 (en) * | 2005-02-28 | 2007-08-09 | Chiron Corporation and North China Pharmaceutical Corporation | Semi-synthetic desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| TW200808818A (en) | 2006-05-26 | 2008-02-16 | Shionogi & Co | Glycopeptide antibiotic derivatives |
| GB2449156B8 (en) * | 2007-05-08 | 2010-06-02 | Lead Therapeutics Inc | Semi-synthetic glycopeptides with antibacterial activity. |
| AU2008343502A1 (en) * | 2007-12-26 | 2009-07-09 | Biomarin Pharmaceutical Inc. | Novel semi-synthetic glycopeptides as antibacterial agents |
| US20100105607A1 (en) * | 2008-10-24 | 2010-04-29 | Lead Therapeutics, Inc. | Novel semi-synthetic glycopeptides as antibacterial agents |
| GB2465863A (en) * | 2008-12-05 | 2010-06-09 | Lead Therapeutics Inc | Semi-synthetic heptapeptidic glycopeptides for the treatment of bacterial infections |
| EP2499591A2 (en) * | 2009-11-13 | 2012-09-19 | Beckman Coulter, Inc. | Systems and methods for detecting the presence of a biological status using clustering |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0174198B1 (en) * | 1984-09-06 | 1989-03-08 | Fujimori Kogyo Co., Ltd. | Laminated film for packaging |
| US5500410A (en) * | 1989-03-29 | 1996-03-19 | Gruppo Lepetit S.P.A. | Substituted alkylamide derivatives of teicoplanin |
| US5840684A (en) * | 1994-01-28 | 1998-11-24 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| US5488131A (en) | 1994-03-23 | 1996-01-30 | California Institute Of Technology | Synthesis of compounds with predetermined chirality |
| US5919756A (en) * | 1996-06-28 | 1999-07-06 | Eli Lilly And Company | Amides |
| EP1140993B1 (en) * | 1998-12-23 | 2003-06-11 | Theravance, Inc. | Glycopeptide derivatives and pharmaceutical compositions containing the same |
| US6699836B2 (en) * | 1999-04-02 | 2004-03-02 | The Trustees Of Princeton University | Vancomycin analogs |
| AU5029700A (en) | 1999-05-19 | 2000-12-05 | Merck & Co., Inc. | Glycopeptide antibacterial compounds, compositions containing same and methods of using same |
| US20030008812A1 (en) | 2001-02-02 | 2003-01-09 | Christensen Burton G. | Glycopeptide derivatives |
| US7348309B2 (en) | 2001-03-30 | 2008-03-25 | Wisconsin Alumni Research Foundation | Glycorandomization and production of novel vancomycin analogs |
| JP2006503015A (ja) | 2002-08-30 | 2006-01-26 | カー・イュー・ルーベン・リサーチ・アンド・ディベロップメント | グリコペプチド抗生物質誘導体 |
| AU2003287605A1 (en) | 2002-11-12 | 2004-06-03 | Enzon Pharmaceuticals, Inc. | Polymeric prodrugs of vancomycin |
| JP2006528704A (ja) * | 2003-05-27 | 2006-12-21 | セラヴァンス インコーポレーテッド | グリコペプチド抗細菌剤と組み合わせたポリエンマクロライド抗真菌剤の使用 |
| US7368422B2 (en) * | 2005-02-28 | 2008-05-06 | Novartis Vaccines And Diagnostics Inc. | Semi-synthetic rearranged vancomycin/desmethyl-vancomycin-based glycopeptides with antibiotic activity |
| US7632918B2 (en) | 2005-02-28 | 2009-12-15 | Novartis Vaccines And Diagnostics, Inc. | Semi-synthetic glycopeptides with antibiotic activity |
-
2006
- 2006-02-24 US US11/361,311 patent/US7368422B2/en not_active Expired - Fee Related
- 2006-02-27 BR BRPI0607701-3A patent/BRPI0607701A2/pt not_active IP Right Cessation
- 2006-02-27 EP EP06736361A patent/EP1858908A4/en not_active Withdrawn
- 2006-02-27 CA CA002599336A patent/CA2599336A1/en not_active Abandoned
- 2006-02-27 JP JP2007558123A patent/JP2008531701A/ja active Pending
- 2006-02-27 WO PCT/US2006/007021 patent/WO2006093933A2/en not_active Ceased
- 2006-02-27 AU AU2006218743A patent/AU2006218743A1/en not_active Abandoned
-
2008
- 2008-03-05 US US12/043,076 patent/US20080214444A1/en not_active Abandoned
-
2009
- 2009-02-18 JP JP2009035654A patent/JP2009102445A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008531701A (ja) | 2008-08-14 |
| JP2009102445A (ja) | 2009-05-14 |
| EP1858908A2 (en) | 2007-11-28 |
| WO2006093933A3 (en) | 2007-03-08 |
| WO2006093933A2 (en) | 2006-09-08 |
| US20080214444A1 (en) | 2008-09-04 |
| US7368422B2 (en) | 2008-05-06 |
| EP1858908A4 (en) | 2010-01-27 |
| BRPI0607701A2 (pt) | 2009-11-03 |
| AU2006218743A8 (en) | 2008-04-17 |
| AU2006218743A1 (en) | 2006-09-08 |
| US20070021328A1 (en) | 2007-01-25 |
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