CN107759672A - 万古霉素衍生物、制备方法及其应用 - Google Patents
万古霉素衍生物、制备方法及其应用 Download PDFInfo
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- CN107759672A CN107759672A CN201711062456.0A CN201711062456A CN107759672A CN 107759672 A CN107759672 A CN 107759672A CN 201711062456 A CN201711062456 A CN 201711062456A CN 107759672 A CN107759672 A CN 107759672A
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- Prior art keywords
- alkyl
- vancomycin
- amino
- coor
- aryl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 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 description 42
- 229960003165 vancomycin Drugs 0.000 claims abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 108010059993 Vancomycin Proteins 0.000 claims abstract description 30
- 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 abstract description 30
- 241000894006 Bacteria Species 0.000 claims abstract description 10
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 8
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 238000006722 reduction reaction Methods 0.000 claims abstract description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 63
- 150000002367 halogens Chemical class 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- -1 C5-C12 aryl Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 15
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 5
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- 239000002585 base Substances 0.000 claims description 4
- 229910000085 borane Inorganic materials 0.000 claims description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 3
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| CN201711062456.0A CN107759672A (zh) | 2013-08-19 | 2013-08-19 | 万古霉素衍生物、制备方法及其应用 |
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| 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 |
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| BR (1) | BR112016003491A2 (https=) |
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| WO (1) | WO2015024389A1 (https=) |
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| 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 |
| WO2021113115A1 (en) * | 2019-12-04 | 2021-06-10 | University Of Massachusetts | Compositions and methods for on-demand release of antimicrobial agents |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1052483A (zh) * | 1989-12-13 | 1991-06-26 | 伊莱利利公司 | 糖肽衍生物的改进及有关的糖肽衍生物 |
| WO1996030401A1 (en) * | 1995-03-24 | 1996-10-03 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| CN104418941B (zh) * | 2013-08-19 | 2017-11-07 | 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 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW457248B (en) * | 1994-01-28 | 2001-10-01 | Lilly Co Eli | Glycopeptide antibiotic derivatives |
| CA2337103A1 (en) * | 1998-07-14 | 2000-01-27 | Robert Kerns | Glycopeptide antibiotics, combinatorial libraries of glycopeptide antibiotics and methods of producing same |
| 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 |
| US8778874B2 (en) * | 2004-11-29 | 2014-07-15 | National University Corporation Nagoya University | Glycopeptide antibiotic monomer derivatives |
-
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
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2014
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- 2014-04-22 JP JP2016535311A patent/JP6452698B2/ja not_active Expired - Fee Related
- 2014-04-22 SG SG11201601127TA patent/SG11201601127TA/en unknown
- 2014-04-22 US US14/912,573 patent/US9828413B2/en not_active Expired - Fee Related
- 2014-04-22 AU AU2014311148A patent/AU2014311148B2/en not_active Ceased
- 2014-04-22 EP EP14838314.4A patent/EP3037431A4/en not_active Withdrawn
- 2014-04-22 NZ NZ717098A patent/NZ717098A/en not_active IP Right Cessation
- 2014-04-22 CA CA2921080A patent/CA2921080A1/en not_active Abandoned
- 2014-04-22 KR KR1020167006849A patent/KR20160043094A/ko not_active Ceased
- 2014-04-22 MX MX2016002190A patent/MX2016002190A/es unknown
- 2014-04-22 WO PCT/CN2014/075905 patent/WO2015024389A1/zh not_active Ceased
- 2014-04-22 EA EA201690396A patent/EA029855B1/ru not_active IP Right Cessation
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2016
- 2016-02-15 IL IL244140A patent/IL244140A0/en unknown
- 2016-02-26 ZA ZA2016/01343A patent/ZA201601343B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1052483A (zh) * | 1989-12-13 | 1991-06-26 | 伊莱利利公司 | 糖肽衍生物的改进及有关的糖肽衍生物 |
| WO1996030401A1 (en) * | 1995-03-24 | 1996-10-03 | Eli Lilly And Company | Glycopeptide antibiotic derivatives |
| CN104418941B (zh) * | 2013-08-19 | 2017-11-07 | 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 |
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| Title |
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| UWE EICHELBERGER，ET AL.: "Synthesis of analogues of the 2-O-alkyl glycerate part of the moenomycins", 《TETRAHEDRON》 * |
Also Published As
| Publication number | Publication date |
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| CN104418941B (zh) | 2017-11-07 |
| CA2921080A1 (en) | 2015-02-26 |
| JP2016528262A (ja) | 2016-09-15 |
| BR112016003491A2 (pt) | 2017-09-12 |
| JP6452698B2 (ja) | 2019-01-16 |
| KR20160043094A (ko) | 2016-04-20 |
| CN104418941A (zh) | 2015-03-18 |
| IL244140A0 (en) | 2016-04-21 |
| US9828413B2 (en) | 2017-11-28 |
| MX2016002190A (es) | 2016-11-25 |
| AU2014311148A1 (en) | 2016-03-10 |
| ZA201601343B (en) | 2017-05-31 |
| SG11201601127TA (en) | 2016-03-30 |
| AU2014311148B2 (en) | 2017-07-13 |
| EP3037431A1 (en) | 2016-06-29 |
| EA029855B1 (ru) | 2018-05-31 |
| EA201690396A1 (ru) | 2016-06-30 |
| US20160200768A1 (en) | 2016-07-14 |
| EP3037431A4 (en) | 2017-04-19 |
| WO2015024389A1 (zh) | 2015-02-26 |
| NZ717098A (en) | 2017-06-30 |
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