AU2014295747B2 - Pharmaceutical, water-soluble and antifungal macromolecular compound - Google Patents
Pharmaceutical, water-soluble and antifungal macromolecular compound Download PDFInfo
- Publication number
- AU2014295747B2 AU2014295747B2 AU2014295747A AU2014295747A AU2014295747B2 AU 2014295747 B2 AU2014295747 B2 AU 2014295747B2 AU 2014295747 A AU2014295747 A AU 2014295747A AU 2014295747 A AU2014295747 A AU 2014295747A AU 2014295747 B2 AU2014295747 B2 AU 2014295747B2
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- AU
- Australia
- Prior art keywords
- polyconjugate
- poly
- amino acid
- amphotericin
- macro
- 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.)
- Ceased
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- 229920002521 macromolecule Polymers 0.000 title abstract description 26
- 230000000843 anti-fungal effect Effects 0.000 title description 9
- 229940121375 antifungal agent Drugs 0.000 title description 3
- 239000000126 substance Substances 0.000 claims abstract description 66
- 229920000642 polymer Polymers 0.000 claims abstract description 45
- 150000004291 polyenes Chemical class 0.000 claims abstract description 39
- 239000003120 macrolide antibiotic agent Substances 0.000 claims abstract description 36
- 229960003942 amphotericin b Drugs 0.000 claims description 197
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 182
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 160
- 238000000034 method Methods 0.000 claims description 116
- 150000001413 amino acids Chemical class 0.000 claims description 84
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- 235000001014 amino acid Nutrition 0.000 claims description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims description 32
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 28
- 229940088679 drug related substance Drugs 0.000 claims description 28
- -1 canmtracin Chemical compound 0.000 claims description 21
- MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 18
- 229960002442 glucosamine Drugs 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 230000000379 polymerizing effect Effects 0.000 claims description 14
- IMQSIXYSKPIGPD-NKYUYKLDSA-N filipin Chemical compound CCCCC[C@H](O)[C@@H]1[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@H](O)\C(C)=C\C=C\C=C\C=C\C=C\[C@H](O)[C@@H](C)OC1=O IMQSIXYSKPIGPD-NKYUYKLDSA-N 0.000 claims description 13
- 229960003255 natamycin Drugs 0.000 claims description 13
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 claims description 13
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 12
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- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 11
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- 239000000463 material Substances 0.000 claims description 11
- ALPPGSBMHVCELA-WHUUVLPESA-N methyl (19E,21E,23E,25E,27E,29E,31E)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-17-[7-(4-aminophenyl)-5-hydroxy-7-oxoheptan-2-yl]-1,3,5,7,9,13,37-heptahydroxy-18-methyl-11,15-dioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate methyl (19E,21E,23E,25E,27E,29E,31E)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,7,9,13,37-heptahydroxy-17-[5-hydroxy-7-[4-(methylamino)phenyl]-7-oxoheptan-2-yl]-18-methyl-11,15-dioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate Chemical compound CC1\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C(O[C@H]2[C@H]([C@@H](N)[C@H](O)[C@@H](C)O2)O)CC(O2)C(C(=O)OC)C(O)CC2(O)CC(O)CC(O)CC(O)CC(O)CC(=O)CC(O)CC(=O)OC1C(C)CCC(O)CC(=O)C1=CC=C(N)C=C1.C1=CC(NC)=CC=C1C(=O)CC(O)CCC(C)C1C(C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/C(O[C@H]2[C@H]([C@@H](N)[C@H](O)[C@@H](C)O2)O)CC(O2)C(C(=O)OC)C(O)CC2(O)CC(O)CC(O)CC(O)CC(O)CC(=O)CC(O)CC(=O)O1 ALPPGSBMHVCELA-WHUUVLPESA-N 0.000 claims description 11
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 claims description 9
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 9
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 9
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- 229930195098 Hamycin Natural products 0.000 claims description 8
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- A61K47/645—Polycationic or polyanionic oligopeptides, polypeptides or polyamino acids, e.g. polylysine, polyarginine, polyglutamic acid or peptide TAT
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- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310315504 | 2013-07-25 | ||
| CN201310315504.8 | 2013-07-25 | ||
| PCT/CN2014/000146 WO2015010439A1 (zh) | 2013-07-25 | 2014-02-08 | 药用水溶性抗真菌大分子化合物 |
Publications (2)
| Publication Number | Publication Date |
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| AU2014295747A1 AU2014295747A1 (en) | 2016-02-11 |
| AU2014295747B2 true AU2014295747B2 (en) | 2016-08-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014295747A Ceased AU2014295747B2 (en) | 2013-07-25 | 2014-02-08 | Pharmaceutical, water-soluble and antifungal macromolecular compound |
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| Country | Link |
|---|---|
| US (1) | US20160158376A1 (enExample) |
| EP (1) | EP3025733A4 (enExample) |
| JP (1) | JP2016525129A (enExample) |
| KR (1) | KR101749004B1 (enExample) |
| CN (1) | CN104055787B (enExample) |
| AU (1) | AU2014295747B2 (enExample) |
| CA (1) | CA2919145A1 (enExample) |
| HK (1) | HK1220629A1 (enExample) |
| RU (1) | RU2016103088A (enExample) |
| WO (1) | WO2015010439A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110669087B (zh) * | 2018-07-02 | 2023-03-31 | 上海医药工业研究院 | 两性霉素b肽衍生物及其制备方法 |
| CN110343650B (zh) * | 2019-05-28 | 2020-12-29 | 浙江工业大学 | 一种产两性霉素b的重组结节链霉菌及其应用 |
| CN110577921B (zh) * | 2019-05-28 | 2021-04-02 | 浙江工业大学 | 产两性霉素b的重组结节链霉菌及其应用 |
| CN112094362B (zh) * | 2020-09-29 | 2022-04-12 | 四川大学华西医院 | 烟酰胺核糖或单核苷酸类似物-大分子载体轭合物及制法和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1596129A (zh) * | 2001-06-21 | 2005-03-16 | 费森尤斯卡比德国有限公司 | 多糖结合物形式的含有氨基糖的水溶性抗生素 |
| CN101333044A (zh) * | 2008-05-20 | 2008-12-31 | 北京能拓高科技有限公司 | 箱式组合式污水处理系统 |
| CN101935336A (zh) * | 2010-09-01 | 2011-01-05 | 北京大学 | 一类水溶性紫杉烷类药物的制备方法和应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1359473A (en) | 1970-11-03 | 1974-07-10 | Prodotti Antibiotici Spa | Polyenic antibiotic |
| AU5858690A (en) * | 1989-06-14 | 1991-01-08 | Cetus Corporation | Polymer/antibiotic conjugate |
| US5610264A (en) | 1995-11-16 | 1997-03-11 | Calwood Chemical Industries, Inc. | Continuous process for polyaspartic acid synthesis |
| DE10155098A1 (de) * | 2001-11-09 | 2003-05-22 | Supramol Parenteral Colloids | Mittel zur Prävention von mykotischen Kontaminationen bei der Zell- und Gewebekultur bakteriellen, pflanzlichen, animalischen und humanen Ursprungs, bestehend aus Polyen-Makrolid-Konjugaten mit Polysacchariden |
| US7261875B2 (en) * | 2001-12-21 | 2007-08-28 | Board Of Regents, The University Of Texas System | Dendritic poly (amino acid) carriers and methods of use |
| CA2625426A1 (en) * | 2005-09-22 | 2007-03-29 | Hadasit Medical Research Services & Development Limited | Dextran and arabinogalactan conjugates of therapeutically active compounds |
| US20080181852A1 (en) * | 2007-01-29 | 2008-07-31 | Nitto Denko Corporation | Multi-functional Drug Carriers |
| EP2277547A1 (de) * | 2009-07-20 | 2011-01-26 | Merck Patent GmbH | Epsilon-Polylysin-Konjugate und deren Verwendung |
| CA2809934C (en) * | 2010-09-02 | 2018-09-04 | Nippon Kayaku Kabushiki Kaisha | Process for producing drug-block copolymer composite and pharmaceutical preparation containing same |
| US8785569B2 (en) * | 2011-11-22 | 2014-07-22 | Original Biomedicals Co., Ltd. | Drug carrier with chelating complex micelles and the application thereof |
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2013
- 2013-12-16 CN CN201310688394.XA patent/CN104055787B/zh not_active Expired - Fee Related
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2014
- 2014-02-08 KR KR1020167001958A patent/KR101749004B1/ko not_active Expired - Fee Related
- 2014-02-08 RU RU2016103088A patent/RU2016103088A/ru unknown
- 2014-02-08 JP JP2016528298A patent/JP2016525129A/ja active Pending
- 2014-02-08 WO PCT/CN2014/000146 patent/WO2015010439A1/zh not_active Ceased
- 2014-02-08 EP EP14829240.2A patent/EP3025733A4/en not_active Withdrawn
- 2014-02-08 CA CA2919145A patent/CA2919145A1/en not_active Abandoned
- 2014-02-08 US US14/907,555 patent/US20160158376A1/en not_active Abandoned
- 2014-02-08 HK HK16108769.4A patent/HK1220629A1/en unknown
- 2014-02-08 AU AU2014295747A patent/AU2014295747B2/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1596129A (zh) * | 2001-06-21 | 2005-03-16 | 费森尤斯卡比德国有限公司 | 多糖结合物形式的含有氨基糖的水溶性抗生素 |
| CN101333044A (zh) * | 2008-05-20 | 2008-12-31 | 北京能拓高科技有限公司 | 箱式组合式污水处理系统 |
| CN101935336A (zh) * | 2010-09-01 | 2011-01-05 | 北京大学 | 一类水溶性紫杉烷类药物的制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101749004B1 (ko) | 2017-06-19 |
| CN104055787A (zh) | 2014-09-24 |
| CN104055787B (zh) | 2017-04-26 |
| JP2016525129A (ja) | 2016-08-22 |
| RU2016103088A (ru) | 2017-08-30 |
| CA2919145A1 (en) | 2015-01-29 |
| US20160158376A1 (en) | 2016-06-09 |
| EP3025733A4 (en) | 2017-09-20 |
| EP3025733A1 (en) | 2016-06-01 |
| AU2014295747A1 (en) | 2016-02-11 |
| HK1220629A1 (en) | 2017-05-12 |
| WO2015010439A1 (zh) | 2015-01-29 |
| KR20160022915A (ko) | 2016-03-02 |
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