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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- 238000013207 serial dilution Methods 0.000 description 1
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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
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000001509 sodium citrate Substances 0.000 description 1
- 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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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 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
- 238000011269 treatment regimen Methods 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 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 |
|---|---|---|---|---|
| EP1818340A4 (en) | 2004-11-29 | 2009-02-25 | Univ Nagoya Nat Univ Corp | ANTIBIOTIC MONOMERS GLYCOPEPTIDE DERIVATIVES |
| 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 |
| US7632918B2 (en) * | 2005-02-28 | 2009-12-15 | Novartis Vaccines And Diagnostics, Inc. | Semi-synthetic 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. |
| KR20100109936A (ko) * | 2007-12-26 | 2010-10-11 | 리드 테라퓨틱스, 인크. | 항박테리아제로서의 신규한 반(半)-합성 글리코펩티드 |
| WO2010048340A2 (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 |
| WO2011060222A2 (en) * | 2009-11-13 | 2011-05-19 | Beckman Coulter, Inc. | Systems and methods for detecting the presence of a biological status using clustering |
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|---|---|---|---|---|
| US4692327A (en) * | 1984-09-06 | 1987-09-08 | Fujimori Kogyo Co., Inc. | 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 |
| BRPI9914221B8 (pt) * | 1998-12-23 | 2021-05-25 | Advanced Medicine Inc | derivados de glicopeptídeos e composições farmacêuticas contendo os mesmos |
| US6699836B2 (en) * | 1999-04-02 | 2004-03-02 | The Trustees Of Princeton University | Vancomycin analogs |
| US6498238B1 (en) * | 1999-05-19 | 2002-12-24 | Princeton University | 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 |
| KR20060091049A (ko) | 2002-08-30 | 2006-08-17 | 케이.유.루벤 리서치 앤드 디벨럽먼트 | 글리코펩티드 항생제 및 그것의 반합성 유도체 및 항바이러스제로서의 그것의 사용 |
| AU2003287605A1 (en) * | 2002-11-12 | 2004-06-03 | Enzon Pharmaceuticals, Inc. | Polymeric prodrugs of vancomycin |
| US7521418B2 (en) * | 2003-05-27 | 2009-04-21 | Theravance, Inc. | Use of a polyene macrolide antifungal agent in combination with a glycopeptide antibacterial agent |
| 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 JP JP2007558123A patent/JP2008531701A/ja active Pending
- 2006-02-27 WO PCT/US2006/007021 patent/WO2006093933A2/en not_active Ceased
- 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 AU AU2006218743A patent/AU2006218743A1/en not_active Abandoned
-
2008
- 2008-03-05 US US12/043,076 patent/US20080214444A1/en not_active Abandoned
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2009
- 2009-02-18 JP JP2009035654A patent/JP2009102445A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006093933A3 (en) | 2007-03-08 |
| JP2009102445A (ja) | 2009-05-14 |
| AU2006218743A1 (en) | 2006-09-08 |
| US20070021328A1 (en) | 2007-01-25 |
| AU2006218743A8 (en) | 2008-04-17 |
| BRPI0607701A2 (pt) | 2009-11-03 |
| US20080214444A1 (en) | 2008-09-04 |
| JP2008531701A (ja) | 2008-08-14 |
| WO2006093933A2 (en) | 2006-09-08 |
| EP1858908A2 (en) | 2007-11-28 |
| EP1858908A4 (en) | 2010-01-27 |
| US7368422B2 (en) | 2008-05-06 |
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