JP2014533678A5 - - Google Patents
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- Publication number
- JP2014533678A5 JP2014533678A5 JP2014541753A JP2014541753A JP2014533678A5 JP 2014533678 A5 JP2014533678 A5 JP 2014533678A5 JP 2014541753 A JP2014541753 A JP 2014541753A JP 2014541753 A JP2014541753 A JP 2014541753A JP 2014533678 A5 JP2014533678 A5 JP 2014533678A5
- Authority
- JP
- Japan
- Prior art keywords
- nonapeptide
- alkyl
- compound
- group
- prodrug
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 23
- 229940002612 prodrug Drugs 0.000 claims 20
- 239000000651 prodrug Substances 0.000 claims 20
- -1 2-hydroxyoctanoyl Chemical group 0.000 claims 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- PYHYGIPVYYRJHU-LPGHPFMSSA-N (2s,3r)-2-amino-n-[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15s,18s,21s)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1r)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]-3-hydroxybutanamid Polymers N1C(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@@H](N)[C@@H](C)O)CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CC1=CC=CC=C1 PYHYGIPVYYRJHU-LPGHPFMSSA-N 0.000 claims 13
- 108700026839 polymyxin B nonapeptide Proteins 0.000 claims 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 108010078777 Colistin Proteins 0.000 claims 4
- XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 claims 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Polymers CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 claims 3
- YKQOSKADJPQZHB-YNWHQGOSSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1s)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Polymers CCC(C)CCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O YKQOSKADJPQZHB-YNWHQGOSSA-N 0.000 claims 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N 2,4-diaminobutyric acid Chemical compound NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 208000034950 Acinetobacter Infections Diseases 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 125000001711 D-phenylalanine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 206010061259 Klebsiella infection Diseases 0.000 claims 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical group CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229960003346 colistin Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- 235000014705 isoleucine Nutrition 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 claims 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161561361P | 2011-11-18 | 2011-11-18 | |
| US61/561,361 | 2011-11-18 | ||
| PCT/GB2012/052844 WO2013072695A1 (en) | 2011-11-18 | 2012-11-16 | Polymyxin derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014533678A JP2014533678A (ja) | 2014-12-15 |
| JP2014533678A5 true JP2014533678A5 (enExample) | 2016-01-14 |
| JP6185920B2 JP6185920B2 (ja) | 2017-08-23 |
Family
ID=47297320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014541753A Expired - Fee Related JP6185920B2 (ja) | 2011-11-18 | 2012-11-16 | ポリミキシン誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9234006B2 (enExample) |
| EP (1) | EP2780357A1 (enExample) |
| JP (1) | JP6185920B2 (enExample) |
| KR (1) | KR20140091724A (enExample) |
| CN (1) | CN103946233A (enExample) |
| AU (1) | AU2012338571B2 (enExample) |
| BR (1) | BR112014012016A2 (enExample) |
| CA (1) | CA2855916A1 (enExample) |
| CO (1) | CO7061068A2 (enExample) |
| EA (1) | EA024792B1 (enExample) |
| IL (1) | IL232278A0 (enExample) |
| MX (1) | MX355217B (enExample) |
| SG (1) | SG11201402390PA (enExample) |
| TW (1) | TWI608019B (enExample) |
| WO (1) | WO2013072695A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX355217B (es) | 2011-11-18 | 2018-04-10 | New Pharma Licence Holdings Ltd | Derivados de polimixina. |
| HUE059544T2 (hu) * | 2013-05-22 | 2022-11-28 | Spero Therapeutics Inc | Polimixin-származékok és ezek alkalmazása kombinációs terápiában különbözõ antibiotikumokkal |
| KR20160135739A (ko) * | 2014-03-11 | 2016-11-28 | 뉴 파마 라이센스 홀딩스 리미티드 | 폴리믹신 유도체 및 상이한 항생제와의 조합 요법에 있어서의 이들의 용도 |
| US10047126B2 (en) | 2014-04-01 | 2018-08-14 | Monash University | Polymyxin derivatives as antimicrobial compounds |
| CN107108699A (zh) * | 2014-11-26 | 2017-08-29 | 新药物许可控股有限公司 | 化合物 |
| EP3233889B1 (en) * | 2014-12-16 | 2022-07-06 | Shanghai MicuRx Pharmaceutical Co., Ltd. | Antimicrobial polymyxins for treatment of bacterial infections |
| FI126143B (en) | 2015-01-15 | 2016-07-15 | Northern Antibiotics Oy | Polymyxine derivative and its uses |
| US9763996B2 (en) | 2015-01-16 | 2017-09-19 | Northern Antibiotics, Ltd. | Polymyxin derivative and uses thereof |
| US10322187B2 (en) | 2015-08-10 | 2019-06-18 | Lehigh University | Reduced toxicity molecular conjugates of anti-fungal agents |
| JP7367950B2 (ja) | 2015-09-29 | 2023-10-24 | モナッシュ ユニバーシティ | 抗菌性ポリミキシン誘導体化合物 |
| BR112019004877A2 (pt) * | 2016-09-13 | 2019-06-11 | Centauri Therapeutics Limited | novos compostos e usos terapêuticos dos mesmos |
| CN108226315B (zh) * | 2016-12-15 | 2022-04-12 | 上海医药工业研究院 | 一种检测多黏菌素e残留量的分析方法 |
| WO2019084628A1 (en) * | 2017-11-02 | 2019-05-09 | The University Of Queensland | Peptide antibiotics |
| DK3810633T3 (da) | 2018-06-25 | 2024-01-15 | Spero Therapeutics Inc | Forbindelser |
| CN111690040A (zh) * | 2019-03-12 | 2020-09-22 | 上海来益生物药物研究开发中心有限责任公司 | 多粘菌素衍生物、其制备方法和应用 |
| CN111072757B (zh) * | 2020-01-02 | 2021-10-15 | 上海上药第一生化药业有限公司 | 多黏菌素b组分或其盐及其制备方法和应用 |
| WO2021150792A1 (en) | 2020-01-21 | 2021-07-29 | Micurx Pharmaceuticals, Inc. | Novel compounds and composition for targeted therapy of kidney-associated cancers |
| TW202233649A (zh) | 2020-11-06 | 2022-09-01 | 美商斯佩羅治療學股份有限公司 | 化合物 |
| CN112755174B (zh) * | 2021-02-26 | 2022-11-18 | 沈阳药科大学 | 多粘菌素衍生物及其制备方法和应用 |
| WO2022262823A1 (zh) * | 2021-06-18 | 2022-12-22 | 华南理工大学 | 活性氧自由基响应的多粘菌素前药化合物及其应用 |
| NL2030897B1 (en) * | 2022-02-11 | 2023-08-18 | Univ Leiden | Antibiotic compounds, formulations and methods of use |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2128617A (en) | 1982-10-06 | 1984-05-02 | Martti Vaara | Polypeptides for use in antibacterial therapy |
| AU7753787A (en) | 1986-08-06 | 1988-02-24 | Jean-Luc Fauchere | Production of covalent-linked conjugates from an antibiotic and a non-toxic derivative of polymyxine b |
| US20010021697A1 (en) | 1987-09-14 | 2001-09-13 | Henning Lowenstein | Methods and compositions for the treatment of mammalian infections employing medicaments comprising hymenoptera venom, proteinageous or polypeptide components thereof, or analogues of such proteinaceous or polypeptide components |
| TW274552B (enExample) | 1992-05-26 | 1996-04-21 | Hoechst Ag | |
| US5767068A (en) | 1997-02-13 | 1998-06-16 | Pathogenesis Corporation | Pure biologically active colistin, its components and a colistin formulation for treatment of pulmonary infections |
| JP2007507512A (ja) | 2003-09-30 | 2007-03-29 | コーヒ コーポレーション | 熱傷を治療するための組成物および方法 |
| US20060004185A1 (en) * | 2004-07-01 | 2006-01-05 | Leese Richard A | Peptide antibiotics and peptide intermediates for their prepartion |
| BRPI0715095B8 (pt) * | 2006-08-11 | 2021-05-25 | Northern Antibiotics Oy | derivado de polimixina da fórmula geral (i); produto de combinação; composição farmacêutica; método para se sensibilizar bactérias gram-negativas a um agente antibacteriano; método para o desenvolvimento de antibióticos; método para a redução da toxicidade de polimixinas, octapeptinas naturais e seus derivados durante a aplicação das mesmas no tratamento de infecções em um indivíduo; método para melhorar as propriedades farmacocinéticas, de polimixinas, octapeptinas naturais e seus derivados; método para a sensibilização de bactérias gram-negativas clinicamente importantes a um complemento de mecanismo de defesa presente no soro; uso de um derivado; e processo para a preparação de um derivado de polimixina da fórmula (i). |
| FI20085469A0 (fi) * | 2008-02-08 | 2008-05-16 | Northern Antibiotics Oy | Polymyksiinijohdannaiset, joissa on lyhyt rasvahappohäntä, ja niiden käyttöjä |
| US8329645B2 (en) | 2008-02-08 | 2012-12-11 | Northern Antibiotics Ltd. | Polymyxin derivatives and uses thereof |
| US8193148B2 (en) | 2008-02-08 | 2012-06-05 | Northern Antibiotics Ltd. | Short fatty acid tail polymyxin derivatives and uses thereof |
| ES2334547B1 (es) | 2008-09-10 | 2010-12-03 | Universidad De Barcelona | Compuestos peptidicos antibacterianos. |
| WO2010075416A1 (en) | 2008-12-23 | 2010-07-01 | Biosource Pharm, Inc. | Antibiotic compositions for the treatment of gram negative infections |
| CN101851270A (zh) | 2009-04-03 | 2010-10-06 | 梁浩 | 一种多粘菌素衍生物及其制备方法 |
| WO2010130007A1 (en) | 2009-05-14 | 2010-11-18 | Monash University | Antimicrobial compounds |
| US8415307B1 (en) | 2010-06-23 | 2013-04-09 | Biosource Pharm, Inc. | Antibiotic compositions for the treatment of gram negative infections |
| WO2012051663A1 (en) | 2010-10-21 | 2012-04-26 | Monash University | Antimicrobial compounds |
| WO2012168820A1 (en) * | 2011-06-08 | 2012-12-13 | Pfizer Inc. | Polymyxin derivatives useful as antibacterial agents |
| MX355217B (es) | 2011-11-18 | 2018-04-10 | New Pharma Licence Holdings Ltd | Derivados de polimixina. |
| HUE059544T2 (hu) * | 2013-05-22 | 2022-11-28 | Spero Therapeutics Inc | Polimixin-származékok és ezek alkalmazása kombinációs terápiában különbözõ antibiotikumokkal |
| KR20160135739A (ko) * | 2014-03-11 | 2016-11-28 | 뉴 파마 라이센스 홀딩스 리미티드 | 폴리믹신 유도체 및 상이한 항생제와의 조합 요법에 있어서의 이들의 용도 |
-
2012
- 2012-11-16 MX MX2014005542A patent/MX355217B/es active IP Right Grant
- 2012-11-16 EP EP12797961.5A patent/EP2780357A1/en not_active Withdrawn
- 2012-11-16 JP JP2014541753A patent/JP6185920B2/ja not_active Expired - Fee Related
- 2012-11-16 TW TW101142961A patent/TWI608019B/zh not_active IP Right Cessation
- 2012-11-16 KR KR1020147014427A patent/KR20140091724A/ko not_active Withdrawn
- 2012-11-16 CA CA2855916A patent/CA2855916A1/en not_active Abandoned
- 2012-11-16 WO PCT/GB2012/052844 patent/WO2013072695A1/en not_active Ceased
- 2012-11-16 BR BR112014012016A patent/BR112014012016A2/pt not_active Application Discontinuation
- 2012-11-16 EA EA201490634A patent/EA024792B1/ru not_active IP Right Cessation
- 2012-11-16 CN CN201280055987.6A patent/CN103946233A/zh active Pending
- 2012-11-16 US US14/356,868 patent/US9234006B2/en active Active
- 2012-11-16 AU AU2012338571A patent/AU2012338571B2/en not_active Ceased
- 2012-11-16 SG SG11201402390PA patent/SG11201402390PA/en unknown
-
2014
- 2014-04-28 IL IL232278A patent/IL232278A0/en unknown
- 2014-06-13 CO CO14128978A patent/CO7061068A2/es unknown
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