CA2968902C - Compounds derived from polymyxin - Google Patents
Compounds derived from polymyxin Download PDFInfo
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- CA2968902C CA2968902C CA2968902A CA2968902A CA2968902C CA 2968902 C CA2968902 C CA 2968902C CA 2968902 A CA2968902 A CA 2968902A CA 2968902 A CA2968902 A CA 2968902A CA 2968902 C CA2968902 C CA 2968902C
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- alkyl
- nitrogen
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 545
- 108010040201 Polymyxins Proteins 0.000 title description 230
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 229
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 211
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 208
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 174
- 125000000539 amino acid group Chemical group 0.000 claims abstract description 163
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims abstract description 92
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 88
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims abstract description 72
- 239000004473 Threonine Substances 0.000 claims abstract description 44
- 238000011282 treatment Methods 0.000 claims abstract description 43
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims abstract description 37
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims abstract description 36
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims abstract description 35
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims abstract description 33
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims abstract description 23
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical group CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims abstract description 22
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims abstract description 21
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims abstract description 20
- 239000004474 valine Substances 0.000 claims abstract description 20
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229960000310 isoleucine Drugs 0.000 claims abstract description 13
- 235000014705 isoleucine Nutrition 0.000 claims abstract description 13
- 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 abstract description 10
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 295
- 125000000623 heterocyclic group Chemical group 0.000 claims description 134
- 125000003118 aryl group Chemical group 0.000 claims description 125
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 117
- 125000001424 substituent group Chemical group 0.000 claims description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 150000001721 carbon Chemical group 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 58
- 125000005843 halogen group Chemical group 0.000 claims description 52
- 239000012453 solvate Substances 0.000 claims description 52
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 229960002898 threonine Drugs 0.000 claims description 43
- 125000005647 linker group Chemical group 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 39
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 36
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 35
- 229960003136 leucine Drugs 0.000 claims description 33
- 229960005190 phenylalanine Drugs 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 31
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 31
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 30
- 241000894006 Bacteria Species 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000002619 bicyclic group Chemical group 0.000 claims description 29
- 208000015181 infectious disease Diseases 0.000 claims description 29
- 125000002950 monocyclic group Chemical group 0.000 claims description 29
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 28
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 21
- 230000000813 microbial effect Effects 0.000 claims description 21
- 229960004295 valine Drugs 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 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 description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 125000005488 carboaryl group Chemical group 0.000 claims description 14
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 14
- 229960001153 serine Drugs 0.000 claims description 14
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Chemical group 0.000 claims description 10
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims description 3
- 241000588722 Escherichia Species 0.000 claims description 3
- 241000607142 Salmonella Species 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 241001135756 Alphaproteobacteria Species 0.000 claims description 2
- 241000604933 Bdellovibrio Species 0.000 claims description 2
- 241000588921 Enterobacteriaceae Species 0.000 claims description 2
- 241000589989 Helicobacter Species 0.000 claims description 2
- 241000588748 Klebsiella Species 0.000 claims description 2
- 241000589248 Legionella Species 0.000 claims description 2
- 208000007764 Legionnaires' Disease Diseases 0.000 claims description 2
- 241000588621 Moraxella Species 0.000 claims description 2
- 241000588772 Morganella morganii Species 0.000 claims description 2
- 241000589516 Pseudomonas Species 0.000 claims description 2
- 241000607768 Shigella Species 0.000 claims description 2
- 241000122971 Stenotrophomonas Species 0.000 claims description 2
- 241000607477 Yersinia pseudotuberculosis Species 0.000 claims description 2
- 229940076266 morganella morganii Drugs 0.000 claims description 2
- 241000589291 Acinetobacter Species 0.000 claims 1
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims 1
- 241000588923 Citrobacter Species 0.000 claims 1
- 241000588914 Enterobacter Species 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 74
- 238000002360 preparation method Methods 0.000 abstract description 20
- -1 His Chemical compound 0.000 description 148
- 229940024606 amino acid Drugs 0.000 description 94
- 239000000203 mixture Substances 0.000 description 77
- 229920000024 polymyxin B Polymers 0.000 description 77
- 229960005266 polymyxin b Drugs 0.000 description 76
- 235000001014 amino acid Nutrition 0.000 description 75
- 108010093965 Polymyxin B Proteins 0.000 description 70
- 239000003795 chemical substances by application Substances 0.000 description 57
- BVAUMRCGVHUWOZ-ZETCQYMHSA-N (2s)-2-(cyclohexylazaniumyl)propanoate Chemical compound OC(=O)[C@H](C)NC1CCCCC1 BVAUMRCGVHUWOZ-ZETCQYMHSA-N 0.000 description 56
- 150000001413 amino acids Chemical class 0.000 description 54
- 230000000694 effects Effects 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 125000006413 ring segment Chemical group 0.000 description 45
- 125000000304 alkynyl group Chemical group 0.000 description 43
- 125000003342 alkenyl group Chemical group 0.000 description 42
- 239000000463 material Substances 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- 125000003277 amino group Chemical group 0.000 description 38
- 125000004433 nitrogen atom Chemical group N* 0.000 description 38
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- 239000000543 intermediate Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
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- 125000006239 protecting group Chemical group 0.000 description 26
- 241000588626 Acinetobacter baumannii Species 0.000 description 25
- 108010078777 Colistin Proteins 0.000 description 25
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
- 230000004071 biological effect Effects 0.000 description 22
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- 238000003786 synthesis reaction Methods 0.000 description 22
- 125000003275 alpha amino acid group Chemical group 0.000 description 21
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 20
- 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 description 20
- 125000003106 haloaryl group Chemical group 0.000 description 19
- 125000001072 heteroaryl group Chemical group 0.000 description 19
- 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 description 19
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- 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 description 14
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- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin 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](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- 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 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- KGPGQDLTDHGEGT-JCIKCJKQSA-N zeven Chemical compound C=1C([C@@H]2C(=O)N[C@H](C(N[C@H](C3=CC(O)=C4)C(=O)NCCCN(C)C)=O)[C@H](O)C5=CC=C(C(=C5)Cl)OC=5C=C6C=C(C=5O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@H](O5)C(O)=O)NC(=O)CCCCCCCCC(C)C)OC5=CC=C(C=C5)C[C@@H]5C(=O)N[C@H](C(N[C@H]6C(=O)N2)=O)C=2C(Cl)=C(O)C=C(C=2)OC=2C(O)=CC=C(C=2)[C@H](C(N5)=O)NC)=CC=C(O)C=1C3=C4O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O KGPGQDLTDHGEGT-JCIKCJKQSA-N 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- ORQXBVXKBGUSBA-QMMMGPOBSA-N β-cyclohexyl-alanine Chemical compound OC(=O)[C@@H](N)CC1CCCCC1 ORQXBVXKBGUSBA-QMMMGPOBSA-N 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/60—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation occurring through the 4-amino group of 2,4-diamino-butanoic acid
- C07K7/62—Polymyxins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1421020.7 | 2014-11-26 | ||
| GBGB1421020.7A GB201421020D0 (en) | 2014-11-26 | 2014-11-26 | Compounds |
| GB1516059.1 | 2015-09-10 | ||
| GBGB1516059.1A GB201516059D0 (en) | 2015-09-10 | 2015-09-10 | Compounds |
| PCT/EP2015/077821 WO2016083531A1 (en) | 2014-11-26 | 2015-11-26 | Compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2968902A1 CA2968902A1 (en) | 2016-06-02 |
| CA2968902C true CA2968902C (en) | 2023-08-29 |
Family
ID=54705181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2968902A Active CA2968902C (en) | 2014-11-26 | 2015-11-26 | Compounds derived from polymyxin |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US12146004B2 (enExample) |
| EP (1) | EP3224273A1 (enExample) |
| JP (1) | JP7349773B2 (enExample) |
| CN (1) | CN107108699A (enExample) |
| AU (1) | AU2015352440B2 (enExample) |
| CA (1) | CA2968902C (enExample) |
| TW (1) | TWI757229B (enExample) |
| WO (1) | WO2016083531A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3224273A1 (en) * | 2014-11-26 | 2017-10-04 | New Pharma Licence Holdings Limited | Compounds |
| WO2018006063A1 (en) * | 2016-07-01 | 2018-01-04 | Cidara Therapeutics, Inc. | Compositions and methods for the treatment of bacterial infections |
| AU2017376711B2 (en) * | 2016-12-16 | 2020-07-16 | Institute Of Medicinal Biotechnology, Chinese Academy Of Medical Sciences | Polymyxin derivative, preparation method and application thereof |
| US11279733B2 (en) | 2017-11-02 | 2022-03-22 | The University Of Queensland | Peptide antibiotics |
| PL3810633T3 (pl) * | 2018-06-25 | 2024-04-08 | Spero Therapeutics, Inc. | Związki |
| 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 |
| WO2021150792A1 (en) | 2020-01-21 | 2021-07-29 | Micurx Pharmaceuticals, Inc. | Novel compounds and composition for targeted therapy of kidney-associated cancers |
| CN111559992B (zh) * | 2020-05-29 | 2022-04-08 | 华中科技大学 | 一种2-芳基-γ-氨基丁酸衍生物的制备方法 |
| 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 |
| WO2022206826A1 (zh) * | 2021-03-31 | 2022-10-06 | 江苏奥赛康药业有限公司 | 一种多粘菌素衍生物的硫酸盐及其药物组合物 |
Family Cites Families (27)
| 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 |
| CA2540742A1 (en) | 2003-09-30 | 2005-04-14 | Terry Hicks | 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 |
| CN103059106B (zh) | 2006-08-11 | 2015-01-14 | 北方抗生素有限公司 | 多粘菌素衍生物及其用途 |
| US7807637B2 (en) * | 2006-08-11 | 2010-10-05 | Northern Antibiotics Oy | Polymyxin derivatives and uses thereof |
| US8329645B2 (en) | 2008-02-08 | 2012-12-11 | Northern Antibiotics Ltd. | Polymyxin derivatives and uses thereof |
| FI20085469A0 (fi) | 2008-02-08 | 2008-05-16 | Northern Antibiotics Oy | Polymyksiinijohdannaiset, joissa on lyhyt rasvahappohäntä, ja niiden käyttöjä |
| 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. |
| US8343912B2 (en) | 2008-12-23 | 2013-01-01 | 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 |
| WO2013072695A1 (en) * | 2011-11-18 | 2013-05-23 | Novacta Biosystems Limited | Polymyxin derivatives |
| PL2999711T3 (pl) | 2013-05-22 | 2022-09-26 | Spero Therapeutics, Inc. | Pochodne polimyksyny i ich zastosowanie w terapii skojarzonej razem z różnymi antybiotykami |
| LT3116897T (lt) | 2014-03-11 | 2022-05-10 | Spero Therapeutics, Inc. | Polimiksino dariniai ir jų panaudojimas kompleksinėje terapijoje kartu su skirtingais antibiotikais |
| US10047126B2 (en) | 2014-04-01 | 2018-08-14 | Monash University | Polymyxin derivatives as antimicrobial compounds |
| EP3224273A1 (en) * | 2014-11-26 | 2017-10-04 | New Pharma Licence Holdings Limited | Compounds |
| WO2016166103A1 (en) | 2015-04-13 | 2016-10-20 | Xellia Pharmaceuticals Aps | Polymyxin derivatives |
| AU2016331658B2 (en) | 2015-09-29 | 2021-04-01 | Monash University | Antimicrobial polymyxin derivative compounds |
| PL3810633T3 (pl) | 2018-06-25 | 2024-04-08 | Spero Therapeutics, Inc. | Związki |
-
2015
- 2015-11-26 EP EP15801162.7A patent/EP3224273A1/en not_active Withdrawn
- 2015-11-26 CA CA2968902A patent/CA2968902C/en active Active
- 2015-11-26 AU AU2015352440A patent/AU2015352440B2/en active Active
- 2015-11-26 US US15/529,786 patent/US12146004B2/en active Active
- 2015-11-26 JP JP2017528156A patent/JP7349773B2/ja active Active
- 2015-11-26 TW TW104139459A patent/TWI757229B/zh not_active IP Right Cessation
- 2015-11-26 WO PCT/EP2015/077821 patent/WO2016083531A1/en not_active Ceased
- 2015-11-26 CN CN201580072906.7A patent/CN107108699A/zh active Pending
-
2023
- 2023-04-25 US US18/139,030 patent/US20230340026A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2015352440B2 (en) | 2020-02-06 |
| JP7349773B2 (ja) | 2023-09-25 |
| AU2015352440A1 (en) | 2017-06-29 |
| WO2016083531A1 (en) | 2016-06-02 |
| US20180030092A1 (en) | 2018-02-01 |
| TW201625664A (zh) | 2016-07-16 |
| EP3224273A1 (en) | 2017-10-04 |
| US20230340026A1 (en) | 2023-10-26 |
| US12146004B2 (en) | 2024-11-19 |
| CN107108699A (zh) | 2017-08-29 |
| JP2017538692A (ja) | 2017-12-28 |
| CA2968902A1 (en) | 2016-06-02 |
| TWI757229B (zh) | 2022-03-11 |
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