CA2921080A1 - Vancomycin derivative, and preparation process and application thereof - Google Patents
Vancomycin derivative, and preparation process and application thereof Download PDFInfo
- Publication number
- CA2921080A1 CA2921080A1 CA2921080A CA2921080A CA2921080A1 CA 2921080 A1 CA2921080 A1 CA 2921080A1 CA 2921080 A CA2921080 A CA 2921080A CA 2921080 A CA2921080 A CA 2921080A CA 2921080 A1 CA2921080 A1 CA 2921080A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- aryl
- coor
- hydrogen
- iii
- 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
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical class 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 abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 2
- 230000002829 reductive effect Effects 0.000 claims abstract 5
- 150000002367 halogens Chemical class 0.000 claims 29
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 13
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical class 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)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims 13
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 7
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 7
- -1 C5-C12 aryl Chemical group 0.000 claims 7
- 108010059993 Vancomycin Proteins 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 229960003165 vancomycin Drugs 0.000 claims 6
- 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 claims 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229910052700 potassium Inorganic materials 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- NUAQIRUAZSJTAI-YRPZDAAMSA-N 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](N)CC(C)C)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 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](N)CC(C)C)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 NUAQIRUAZSJTAI-YRPZDAAMSA-N 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 229910000085 borane Inorganic materials 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 108700014375 norvancomycin Proteins 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 1
- 241000192125 Firmicutes Species 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 229910052784 alkaline earth metal Chemical group 0.000 claims 1
- 150000001342 alkaline earth metals Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 229960004592 isopropanol Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 1
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical group OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Gastroenterology & Hepatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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 |
|---|---|---|---|
| CN201310361577.0A CN104418941B (zh) | 2013-08-19 | 2013-08-19 | 万古霉素衍生物、制备方法及其应用 |
| CN2013103615770 | 2013-08-19 | ||
| PCT/CN2014/075905 WO2015024389A1 (zh) | 2013-08-19 | 2014-04-22 | 万古霉素衍生物、制备方法及其应用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2921080A1 true CA2921080A1 (en) | 2015-02-26 |
Family
ID=52483023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2921080A Abandoned CA2921080A1 (en) | 2013-08-19 | 2014-04-22 | Vancomycin derivative, and preparation process and application thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9828413B2 (enExample) |
| EP (1) | EP3037431A4 (enExample) |
| JP (1) | JP6452698B2 (enExample) |
| KR (1) | KR20160043094A (enExample) |
| CN (2) | CN107759672A (enExample) |
| AU (1) | AU2014311148B2 (enExample) |
| BR (1) | BR112016003491A2 (enExample) |
| CA (1) | CA2921080A1 (enExample) |
| EA (1) | EA029855B1 (enExample) |
| IL (1) | IL244140A0 (enExample) |
| MX (1) | MX2016002190A (enExample) |
| NZ (1) | NZ717098A (enExample) |
| SG (1) | SG11201601127TA (enExample) |
| WO (1) | WO2015024389A1 (enExample) |
| ZA (1) | ZA201601343B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107759672A (zh) * | 2013-08-19 | 2018-03-06 | 南京爱斯药业有限公司 | 万古霉素衍生物、制备方法及其应用 |
| CN105985412A (zh) * | 2015-02-28 | 2016-10-05 | 爱斯医药科技(南京)有限公司 | 万古霉素衍生物、制备方法及其应用 |
| CN107365359B (zh) * | 2017-07-17 | 2021-06-04 | 昆明理工大学 | 一种万古霉素手性功能单体合成方法 |
| CN107759671A (zh) * | 2017-09-11 | 2018-03-06 | 昆明理工大学 | 水相中合成万古霉素手性功能单体的方法 |
| USD922342S1 (en) | 2018-10-05 | 2021-06-15 | Samsung Electronics Co., Ltd. | Television receiver |
| USD906992S1 (en) | 2018-12-13 | 2021-01-05 | Samsung Electronics Co., Ltd. | Television receiver |
| CN112079902B (zh) * | 2019-06-12 | 2025-05-06 | 迪普深合医药研发(上海)有限公司 | 万古霉素衍生物、其中间体、制备方法、组合物及用途 |
| EP4069712A4 (en) * | 2019-12-04 | 2024-03-13 | University of Massachusetts | COMPOSITIONS AND METHODS FOR ON-DEMAND RELEASE OF ANTIMICROBIAL AGENTS |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA909847B (en) * | 1989-12-13 | 1992-08-26 | Lilly Co Eli | Glycopeptide derivatives |
| US5840684A (en) * | 1994-01-28 | 1998-11-24 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| NZ270387A (en) * | 1994-01-28 | 1996-11-26 | Lilly Co Eli | Glycopeptide antibiotic, its production and compositions thereof |
| EP1095058A4 (en) * | 1998-07-14 | 2003-07-16 | Univ Princeton | GLYCOPEPTIDANTIBIOTICS, COMBINATIONAL LIBRARIES OF GLYCOPEPTIDANTIBIOTICS AND METHOD FOR THEIR PRODUCTION |
| GB0026924D0 (en) | 2000-11-03 | 2000-12-20 | Univ Cambridge Tech | Antibacterial agents |
| TWI233932B (en) * | 2001-08-24 | 2005-06-11 | Theravance Inc | Process for purifying glycopeptide phosphonate derivatives |
| US8193312B2 (en) | 2004-01-28 | 2012-06-05 | The Regents Of The University Of California | Bone morphogenic protein binding peptide |
| WO2006057303A1 (ja) * | 2004-11-29 | 2006-06-01 | National University Corporation Nagoya University | グリコペプチド抗生物質モノマー誘導体 |
| CN107759672A (zh) * | 2013-08-19 | 2018-03-06 | 南京爱斯药业有限公司 | 万古霉素衍生物、制备方法及其应用 |
-
2013
- 2013-08-19 CN CN201711062456.0A patent/CN107759672A/zh active Pending
- 2013-08-19 CN CN201310361577.0A patent/CN104418941B/zh not_active Expired - Fee Related
-
2014
- 2014-04-22 CA CA2921080A patent/CA2921080A1/en not_active Abandoned
- 2014-04-22 BR BR112016003491A patent/BR112016003491A2/pt not_active IP Right Cessation
- 2014-04-22 NZ NZ717098A patent/NZ717098A/en not_active IP Right Cessation
- 2014-04-22 EA EA201690396A patent/EA029855B1/ru not_active IP Right Cessation
- 2014-04-22 AU AU2014311148A patent/AU2014311148B2/en not_active Ceased
- 2014-04-22 WO PCT/CN2014/075905 patent/WO2015024389A1/zh not_active Ceased
- 2014-04-22 KR KR1020167006849A patent/KR20160043094A/ko not_active Ceased
- 2014-04-22 MX MX2016002190A patent/MX2016002190A/es unknown
- 2014-04-22 JP JP2016535311A patent/JP6452698B2/ja not_active Expired - Fee Related
- 2014-04-22 EP EP14838314.4A patent/EP3037431A4/en not_active Withdrawn
- 2014-04-22 SG SG11201601127TA patent/SG11201601127TA/en unknown
- 2014-04-22 US US14/912,573 patent/US9828413B2/en not_active Expired - Fee Related
-
2016
- 2016-02-15 IL IL244140A patent/IL244140A0/en unknown
- 2016-02-26 ZA ZA2016/01343A patent/ZA201601343B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2016002190A (es) | 2016-11-25 |
| ZA201601343B (en) | 2017-05-31 |
| JP2016528262A (ja) | 2016-09-15 |
| JP6452698B2 (ja) | 2019-01-16 |
| NZ717098A (en) | 2017-06-30 |
| EP3037431A1 (en) | 2016-06-29 |
| SG11201601127TA (en) | 2016-03-30 |
| IL244140A0 (en) | 2016-04-21 |
| BR112016003491A2 (pt) | 2017-09-12 |
| CN107759672A (zh) | 2018-03-06 |
| EA201690396A1 (ru) | 2016-06-30 |
| EA029855B1 (ru) | 2018-05-31 |
| KR20160043094A (ko) | 2016-04-20 |
| US9828413B2 (en) | 2017-11-28 |
| US20160200768A1 (en) | 2016-07-14 |
| CN104418941A (zh) | 2015-03-18 |
| CN104418941B (zh) | 2017-11-07 |
| WO2015024389A1 (zh) | 2015-02-26 |
| EP3037431A4 (en) | 2017-04-19 |
| AU2014311148A1 (en) | 2016-03-10 |
| AU2014311148B2 (en) | 2017-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160211 |
|
| FZDE | Discontinued |
Effective date: 20190423 |