JP2018506272A5 - - Google Patents
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- JP2018506272A5 JP2018506272A5 JP2017535019A JP2017535019A JP2018506272A5 JP 2018506272 A5 JP2018506272 A5 JP 2018506272A5 JP 2017535019 A JP2017535019 A JP 2017535019A JP 2017535019 A JP2017535019 A JP 2017535019A JP 2018506272 A5 JP2018506272 A5 JP 2018506272A5
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- JP
- Japan
- Prior art keywords
- cpp
- alkyl
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- formula
- compound
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 230000008685 targeting Effects 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- -1 4-methoxytrityl Chemical group 0.000 claims description 21
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 20
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 20
- 108010078777 Colistin Proteins 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 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 description 16
- 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 description 16
- 125000005647 linker group Chemical group 0.000 claims description 14
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 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 description 12
- 108700026839 polymyxin B nonapeptide Proteins 0.000 claims description 12
- 229940113082 thymine Drugs 0.000 claims description 10
- 229940035893 uracil Drugs 0.000 claims description 10
- 108010093965 Polymyxin B Proteins 0.000 claims description 8
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 8
- 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 description 8
- 229920000024 polymyxin B Polymers 0.000 claims description 8
- 229960005266 polymyxin b Drugs 0.000 claims description 8
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 7
- 101150004974 ACP3 gene Proteins 0.000 claims description 7
- 241000023308 Acca Species 0.000 claims description 7
- 101150029029 CAVIN4 gene Proteins 0.000 claims description 7
- 101100000438 Mus musculus Acacb gene Proteins 0.000 claims description 7
- 101100426065 Mus musculus Trim54 gene Proteins 0.000 claims description 7
- 210000000170 cell membrane Anatomy 0.000 claims description 7
- 230000000295 complement effect Effects 0.000 claims description 7
- 108020004999 messenger RNA Proteins 0.000 claims description 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 7
- 210000004899 c-terminal region Anatomy 0.000 claims description 6
- 208000032536 Pseudomonas Infections Diseases 0.000 claims description 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical group NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical group NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 2
- 229960002684 aminocaproic acid Drugs 0.000 claims description 2
- 229940000635 beta-alanine Drugs 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 239000002773 nucleotide Substances 0.000 claims description 2
- 125000003729 nucleotide group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- VHNZDWLFXDSLGB-UHFFFAOYSA-N CN(C)P(N(CC1)CCN1C(OCCOCCOCCO)=O)(OC=[IH])=O Chemical compound CN(C)P(N(CC1)CCN1C(OCCOCCOCCO)=O)(OC=[IH])=O VHNZDWLFXDSLGB-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021202636A JP2022040131A (ja) | 2014-12-31 | 2021-12-14 | アンチセンス抗細菌性化合物および方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462098713P | 2014-12-31 | 2014-12-31 | |
| US62/098,713 | 2014-12-31 | ||
| PCT/US2015/000280 WO2016108930A2 (en) | 2014-12-31 | 2015-12-23 | Antisense antibacterial compounds and methods |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021202636A Division JP2022040131A (ja) | 2014-12-31 | 2021-12-14 | アンチセンス抗細菌性化合物および方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018506272A JP2018506272A (ja) | 2018-03-08 |
| JP2018506272A5 true JP2018506272A5 (enExample) | 2019-02-07 |
| JP6994941B2 JP6994941B2 (ja) | 2022-02-04 |
Family
ID=56285129
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017535019A Active JP6994941B2 (ja) | 2014-12-31 | 2015-12-23 | アンチセンス抗細菌性化合物および方法 |
| JP2021202636A Withdrawn JP2022040131A (ja) | 2014-12-31 | 2021-12-14 | アンチセンス抗細菌性化合物および方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021202636A Withdrawn JP2022040131A (ja) | 2014-12-31 | 2021-12-14 | アンチセンス抗細菌性化合物および方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US11293024B2 (enExample) |
| EP (1) | EP3240794A4 (enExample) |
| JP (2) | JP6994941B2 (enExample) |
| AU (1) | AU2015372560B2 (enExample) |
| CA (2) | CA3249464A1 (enExample) |
| HK (1) | HK1246303A1 (enExample) |
| WO (1) | WO2016108930A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2948373A1 (en) | 2014-05-16 | 2015-11-19 | Oregon State University | Antisense antibacterial compounds and methods |
| EP3569252B1 (en) | 2014-05-19 | 2021-12-15 | Oregon State University | Antisense antibacterial compounds and methods |
| CA3249464A1 (en) | 2014-12-31 | 2025-11-29 | Univ Texas | Antisense antibacterial compounds and methods |
| US10907158B2 (en) | 2015-12-23 | 2021-02-02 | Board Of Regents, The University Of Texas System | Antisense antibacterial compounds and methods |
| JP7393121B2 (ja) | 2015-12-23 | 2023-12-06 | オレゴン ステイト ユニバーシティー | アンチセンス抗菌化合物および方法 |
| WO2020035620A1 (en) * | 2018-08-17 | 2020-02-20 | Centre National De La Recherche Scientifique (Cnrs) | Rna-based therapeutic methods to protect animals against pathogenic bacteria and / or promote beneficial effects of symbiotic and commensal bacteria |
| GB2579253A (en) | 2018-11-28 | 2020-06-17 | Pedanius Therapeutics Ltd | Antibacterial antisense agents |
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| WO1986005519A1 (en) | 1985-03-15 | 1986-09-25 | James Summerton | Polynucleotide assay reagent and method |
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| US6245747B1 (en) | 1996-03-12 | 2001-06-12 | The Board Of Regents Of The University Of Nebraska | Targeted site specific antisense oligodeoxynucleotide delivery method |
| AU7327598A (en) * | 1997-05-02 | 1998-11-27 | University Of Guelph | Proteins involved in the synthesis and assembly of core lipopolysaccharide of pseudomonas aeruginosa |
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| CA2948373A1 (en) | 2014-05-16 | 2015-11-19 | Oregon State University | Antisense antibacterial compounds and methods |
| EP3569252B1 (en) | 2014-05-19 | 2021-12-15 | Oregon State University | Antisense antibacterial compounds and methods |
| CA3249464A1 (en) | 2014-12-31 | 2025-11-29 | Univ Texas | Antisense antibacterial compounds and methods |
| US10907158B2 (en) | 2015-12-23 | 2021-02-02 | Board Of Regents, The University Of Texas System | Antisense antibacterial compounds and methods |
| JP7393121B2 (ja) | 2015-12-23 | 2023-12-06 | オレゴン ステイト ユニバーシティー | アンチセンス抗菌化合物および方法 |
-
2015
- 2015-12-23 CA CA3249464A patent/CA3249464A1/en active Pending
- 2015-12-23 CA CA2972653A patent/CA2972653C/en active Active
- 2015-12-23 HK HK18105904.4A patent/HK1246303A1/zh unknown
- 2015-12-23 WO PCT/US2015/000280 patent/WO2016108930A2/en not_active Ceased
- 2015-12-23 JP JP2017535019A patent/JP6994941B2/ja active Active
- 2015-12-23 EP EP15875820.1A patent/EP3240794A4/en active Pending
- 2015-12-23 AU AU2015372560A patent/AU2015372560B2/en active Active
- 2015-12-23 US US15/540,387 patent/US11293024B2/en active Active
-
2021
- 2021-12-14 JP JP2021202636A patent/JP2022040131A/ja not_active Withdrawn