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 (https=) | 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 (https=) |
| EP (1) | EP2780357A1 (https=) |
| JP (1) | JP6185920B2 (https=) |
| KR (1) | KR20140091724A (https=) |
| CN (1) | CN103946233A (https=) |
| AU (1) | AU2012338571B2 (https=) |
| BR (1) | BR112014012016A2 (https=) |
| CA (1) | CA2855916A1 (https=) |
| CO (1) | CO7061068A2 (https=) |
| EA (1) | EA024792B1 (https=) |
| IL (1) | IL232278A0 (https=) |
| MX (1) | MX355217B (https=) |
| SG (1) | SG11201402390PA (https=) |
| TW (1) | TWI608019B (https=) |
| WO (1) | WO2013072695A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112014012016A2 (pt) | 2011-11-18 | 2017-05-16 | Cantab Anti-Infectives Ltd | compostos |
| JP6643758B2 (ja) | 2013-05-22 | 2020-02-12 | スペロ・セラピューティクス・インコーポレーテッド | 異なった抗生物質と一緒の組合せ療法におけるポリミキシン誘導体及びその使用 |
| RU2740190C2 (ru) * | 2014-03-11 | 2021-01-12 | Сперо Терапьютикс, Инк. | Производные полимиксина и их применение в комбинированной терапии совместно с различными антибиотиками |
| 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 |
| US9771394B2 (en) | 2014-12-16 | 2017-09-26 | Micurx Pharmaceuticals, Inc. | 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 |
| EP3356387B1 (en) * | 2015-09-29 | 2024-06-26 | Monash University | Antimicrobial polymyxin derivative compounds |
| MX2019002879A (es) * | 2016-09-13 | 2019-09-18 | Centauri Therapeutics Ltd | Compuestos novedosos y usos terapeuticos de los mismos. |
| 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 |
| AU2018359018B2 (en) * | 2017-11-02 | 2022-11-24 | The University Of Queensland | Peptide antibiotics |
| MD3810633T2 (ro) | 2018-06-25 | 2024-05-31 | Spero Therapeutics Inc | Compuşi |
| 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 |
| JP7045520B2 (ja) * | 2020-01-02 | 2022-03-31 | 上海上薬第一生化薬業有限公司 | ポリミキシンｂ成分又はその塩、その製造方法及び使用 |
| 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 |
| WO1988000950A2 (fr) | 1986-08-06 | 1988-02-11 | Fauchere Jean Luc | Fabrication de conjugues a liaisons de covalence a partir d'un antibiotique et d'un derive non toxique de la 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 (https=) | 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 |
| AU2004277977B2 (en) | 2003-09-30 | 2010-10-28 | Biomechanisms Inc. | Compositions and methods for treating burns |
| US20060004185A1 (en) * | 2004-07-01 | 2006-01-05 | Leese Richard A | Peptide antibiotics and peptide intermediates for their prepartion |
| HUE028271T2 (en) * | 2006-08-11 | 2016-12-28 | Northern Antibiotics Oy | Polymixin derivatives and their applications |
| 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. |
| TW201035111A (en) * | 2008-12-23 | 2010-10-01 | 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 |
| BR112014012016A2 (pt) | 2011-11-18 | 2017-05-16 | Cantab Anti-Infectives Ltd | compostos |
| JP6643758B2 (ja) * | 2013-05-22 | 2020-02-12 | スペロ・セラピューティクス・インコーポレーテッド | 異なった抗生物質と一緒の組合せ療法におけるポリミキシン誘導体及びその使用 |
| RU2740190C2 (ru) * | 2014-03-11 | 2021-01-12 | Сперо Терапьютикс, Инк. | Производные полимиксина и их применение в комбинированной терапии совместно с различными антибиотиками |
-
2012
- 2012-11-16 BR BR112014012016A patent/BR112014012016A2/pt not_active Application Discontinuation
- 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 CN CN201280055987.6A patent/CN103946233A/zh active Pending
- 2012-11-16 CA CA2855916A patent/CA2855916A1/en not_active Abandoned
- 2012-11-16 AU AU2012338571A patent/AU2012338571B2/en not_active Ceased
- 2012-11-16 SG SG11201402390PA patent/SG11201402390PA/en unknown
- 2012-11-16 MX MX2014005542A patent/MX355217B/es active IP Right Grant
- 2012-11-16 EA EA201490634A patent/EA024792B1/ru not_active IP Right Cessation
- 2012-11-16 WO PCT/GB2012/052844 patent/WO2013072695A1/en not_active Ceased
- 2012-11-16 US US14/356,868 patent/US9234006B2/en active Active
- 2012-11-16 KR KR1020147014427A patent/KR20140091724A/ko not_active Withdrawn
-
2014
- 2014-04-28 IL IL232278A patent/IL232278A0/en unknown
- 2014-06-13 CO CO14128978A patent/CO7061068A2/es unknown
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