CA2632968A1 - Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents - Google Patents
Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents Download PDFInfo
- Publication number
- CA2632968A1 CA2632968A1 CA002632968A CA2632968A CA2632968A1 CA 2632968 A1 CA2632968 A1 CA 2632968A1 CA 002632968 A CA002632968 A CA 002632968A CA 2632968 A CA2632968 A CA 2632968A CA 2632968 A1 CA2632968 A1 CA 2632968A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- compound
- alkyl
- alkynyl
- alkenyl
- 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.)
- Abandoned
Links
- 229940126575 aminoglycoside Drugs 0.000 title abstract description 24
- 230000000844 anti-bacterial effect Effects 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 420
- 238000000034 method Methods 0.000 claims description 156
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 125
- -1 -NJ1J2 Chemical group 0.000 claims description 72
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 70
- UOZODPSAJZTQNH-LSWIJEOBSA-N paromomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-LSWIJEOBSA-N 0.000 claims description 69
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 67
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
- 229960001914 paromomycin Drugs 0.000 claims description 55
- UOZODPSAJZTQNH-UHFFFAOYSA-N Paromomycin II Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)CC(N)C2O)OC2C(C(O)C(O)C(CO)O2)N)OC1CO UOZODPSAJZTQNH-UHFFFAOYSA-N 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000006239 protecting group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 229930193140 Neomycin Natural products 0.000 claims description 18
- 229960004927 neomycin Drugs 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 17
- 239000000651 prodrug Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003367 polycyclic group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 7
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract description 37
- 239000003814 drug Substances 0.000 abstract description 13
- 208000015181 infectious disease Diseases 0.000 abstract description 4
- 230000000069 prophylactic effect Effects 0.000 abstract description 3
- 230000000813 microbial effect Effects 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 300
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 161
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 113
- 238000005481 NMR spectroscopy Methods 0.000 description 100
- 239000000243 solution Substances 0.000 description 93
- 229910001868 water Inorganic materials 0.000 description 93
- 239000000203 mixture Substances 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 67
- 235000019439 ethyl acetate Nutrition 0.000 description 63
- 239000002904 solvent Substances 0.000 description 61
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 238000003818 flash chromatography Methods 0.000 description 56
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
- 239000012043 crude product Substances 0.000 description 52
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 49
- 238000003756 stirring Methods 0.000 description 47
- 238000003786 synthesis reaction Methods 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 44
- 239000012044 organic layer Substances 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 42
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 41
- 239000000741 silica gel Substances 0.000 description 37
- 229910002027 silica gel Inorganic materials 0.000 description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
- 239000007832 Na2SO4 Substances 0.000 description 34
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
- 229910052938 sodium sulfate Inorganic materials 0.000 description 34
- 235000011152 sodium sulphate Nutrition 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000000126 substance Substances 0.000 description 32
- 239000012267 brine Substances 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- 238000001704 evaporation Methods 0.000 description 28
- 230000008020 evaporation Effects 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 230000001580 bacterial effect Effects 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- 229910052739 hydrogen Chemical group 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 23
- 239000001257 hydrogen Chemical group 0.000 description 23
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 238000003556 assay Methods 0.000 description 21
- 238000012512 characterization method Methods 0.000 description 21
- 108090000623 proteins and genes Proteins 0.000 description 21
- 102000004169 proteins and genes Human genes 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 241000588724 Escherichia coli Species 0.000 description 19
- 239000013058 crude material Substances 0.000 description 19
- 125000000524 functional group Chemical group 0.000 description 19
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 18
- 239000003242 anti bacterial agent Substances 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- 239000003480 eluent Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 229940088710 antibiotic agent Drugs 0.000 description 16
- 230000027455 binding Effects 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 15
- 238000010189 synthetic method Methods 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- WLLIXJBWWFGEHT-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F WLLIXJBWWFGEHT-UHFFFAOYSA-N 0.000 description 14
- 125000005647 linker group Chemical group 0.000 description 14
- 230000004048 modification Effects 0.000 description 14
- 238000012986 modification Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 13
- 238000000605 extraction Methods 0.000 description 13
- 235000017557 sodium bicarbonate Nutrition 0.000 description 13
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 13
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 241000894006 Bacteria Species 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 239000012298 atmosphere Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 229940125877 compound 31 Drugs 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000003446 ligand Substances 0.000 description 10
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 10
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 238000010511 deprotection reaction Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000013519 translation Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 8
- 238000010791 quenching Methods 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
- 230000001588 bifunctional effect Effects 0.000 description 7
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- 241000699670 Mus sp. Species 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
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- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 6
- 150000003384 small molecules Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
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- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 5
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 4
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 4
- 229940126657 Compound 17 Drugs 0.000 description 4
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- DVWOYOSIEJRHKW-UIRZNSHLSA-M sodium (2S)-2-[[(2S)-2-[[(4,4-difluorocyclohexyl)-phenylmethoxy]carbonylamino]-4-methylpentanoyl]amino]-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonate Chemical compound FC1(CCC(CC1)C(OC(=O)N[C@H](C(=O)N[C@H](C(S(=O)(=O)[O-])O)C[C@H]1C(NCC1)=O)CC(C)C)C1=CC=CC=C1)F.[Na+] DVWOYOSIEJRHKW-UIRZNSHLSA-M 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
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- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
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- 230000001954 sterilising effect Effects 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 150000003456 sulfonamides Chemical class 0.000 description 1
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- JYRWUSXRTGACLY-UHFFFAOYSA-N tert-butyl 4-[[3-(4-methylsulfonylphenyl)-[1,2]oxazolo[4,5-d]pyrimidin-7-yl]oxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC2=C1ON=C2C1=CC=C(S(C)(=O)=O)C=C1 JYRWUSXRTGACLY-UHFFFAOYSA-N 0.000 description 1
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- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- NSFFHOGKXHRQEW-AIHSUZKVSA-N thiostrepton Chemical compound C([C@]12C=3SC=C(N=3)C(=O)N[C@H](C(=O)NC(/C=3SC[C@@H](N=3)C(=O)N[C@H](C=3SC=C(N=3)C(=O)N[C@H](C=3SC=C(N=3)[C@H]1N=1)[C@@H](C)OC(=O)C3=CC(=C4C=C[C@H]([C@@H](C4=N3)O)N[C@H](C(N[C@@H](C)C(=O)NC(=C)C(=O)N[C@@H](C)C(=O)N2)=O)[C@@H](C)CC)[C@H](C)O)[C@](C)(O)[C@@H](C)O)=C\C)[C@@H](C)O)CC=1C1=NC(C(=O)NC(=C)C(=O)NC(=C)C(N)=O)=CS1 NSFFHOGKXHRQEW-AIHSUZKVSA-N 0.000 description 1
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- NSFFHOGKXHRQEW-OFMUQYBVSA-N thiostrepton A Natural products CC[C@H](C)[C@@H]1N[C@@H]2C=Cc3c(cc(nc3[C@H]2O)C(=O)O[C@H](C)[C@@H]4NC(=O)c5csc(n5)[C@@H](NC(=O)[C@H]6CSC(=N6)C(=CC)NC(=O)[C@@H](NC(=O)c7csc(n7)[C@]8(CCC(=N[C@@H]8c9csc4n9)c%10nc(cs%10)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)[C@H](C)NC1=O)[C@@H](C)O)[C@](C)(O)[C@@H](C)O)[C@H](C)O NSFFHOGKXHRQEW-OFMUQYBVSA-N 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
- C07H15/23—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with only two saccharide radicals in the molecule, e.g. ambutyrosin, butyrosin, xylostatin, ribostamycin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
- C07H15/232—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with at least three saccharide radicals in the molecule, e.g. lividomycin, neomycin, paromomycin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74205105P | 2005-12-02 | 2005-12-02 | |
| US60/742,051 | 2005-12-02 | ||
| PCT/US2006/046122 WO2007064954A2 (en) | 2005-12-02 | 2006-12-01 | Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2632968A1 true CA2632968A1 (en) | 2007-06-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002632968A Abandoned CA2632968A1 (en) | 2005-12-02 | 2006-12-01 | Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents |
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| JP (1) | JP5256043B2 (enExample) |
| AU (1) | AU2006320374B2 (enExample) |
| CA (1) | CA2632968A1 (enExample) |
| ES (1) | ES2707787T3 (enExample) |
| WO (1) | WO2007064954A2 (enExample) |
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| WO2006052930A1 (en) | 2004-11-05 | 2006-05-18 | Isis Pharmaceuticals, Inc. | Antimicrobial 2-deoxystreptamine compounds |
| WO2007028012A2 (en) * | 2005-09-01 | 2007-03-08 | Isis Pharmaceuticals, Inc. | Antibacterial 6'-n-modified 4,5-substituted aminoglycoside analogs |
| AU2006320374B2 (en) | 2005-12-02 | 2012-08-30 | Isis Pharmaceuticals, Inc. | Antibacterial 4,5-substituted aminoglycoside analogs having multiple substituents |
| EP1953171A1 (en) * | 2007-02-02 | 2008-08-06 | Eidgenössische Technische Hochschule Zürich | Aminoglycoside antibiotics targeting bacterial 16S ribosomal RNA |
| JP2010527913A (ja) * | 2007-04-10 | 2010-08-19 | アカオジェン インコーポレイテッド | 抗菌性１，４，５置換アミノグリコシド類似体 |
| PT2217610T (pt) | 2007-11-21 | 2017-02-10 | Achaogen Inc | Análogos de aminoglicosido antibacterianos |
| WO2010030690A1 (en) | 2008-09-10 | 2010-03-18 | Isis Pharmaceuticals, Inc. | Antibacterial 4,6-substituted 6', 6" and 1 modified aminoglycoside analogs |
| WO2010030704A2 (en) | 2008-09-10 | 2010-03-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010030808A2 (en) * | 2008-09-11 | 2010-03-18 | Utah State University | Novel antibiotics against resistant bacteria |
| CN102256989B (zh) | 2008-10-03 | 2016-01-06 | 聚糖生物科学有限责任公司 | 糖基化细菌代谢物的阴离子轭合物 |
| WO2010042850A1 (en) | 2008-10-09 | 2010-04-15 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010042851A1 (en) | 2008-10-09 | 2010-04-15 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| SG171914A1 (en) | 2008-12-02 | 2011-07-28 | Chiralgen Ltd | Method for the synthesis of phosphorus atom modified nucleic acids |
| WO2010132765A2 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010132768A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of sisomicin |
| WO2010132757A2 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010132759A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of dibekacin |
| WO2010132760A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of tobramycin |
| EP2451461A4 (en) | 2009-07-06 | 2013-05-29 | Ontorii Inc | NOVEL NUCLEIC ACID PRODRUGS AND METHOD OF USE THEREOF |
| WO2011044502A1 (en) * | 2009-10-09 | 2011-04-14 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2011044538A1 (en) * | 2009-10-09 | 2011-04-14 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| CA2777107A1 (en) * | 2009-10-09 | 2011-04-14 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2011044503A1 (en) * | 2009-10-09 | 2011-04-14 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| CA2791253A1 (en) * | 2010-04-06 | 2011-10-13 | Frank Schweizer | Polyol modified aminoglycoside-lipid conjugates |
| DK2620428T3 (da) | 2010-09-24 | 2019-07-01 | Wave Life Sciences Ltd | Asymmetrisk hjælpegruppe |
| CN103282370A (zh) | 2010-11-17 | 2013-09-04 | 尔察祯有限公司 | 抗菌氨基糖苷类类似物 |
| US9605019B2 (en) | 2011-07-19 | 2017-03-28 | Wave Life Sciences Ltd. | Methods for the synthesis of functionalized nucleic acids |
| CN112007045B (zh) | 2012-07-13 | 2026-01-06 | 波涛生命科学有限公司 | 手性控制 |
| DK2872485T3 (da) | 2012-07-13 | 2021-03-08 | Wave Life Sciences Ltd | Asymmetrisk hjælpegruppe |
| JP6246121B2 (ja) | 2012-07-13 | 2017-12-13 | 株式会社新日本科学 | キラル核酸アジュバント |
| WO2015108048A1 (ja) | 2014-01-15 | 2015-07-23 | 株式会社新日本科学 | 抗腫瘍作用を有するキラル核酸アジュバンド及び抗腫瘍剤 |
| EP3095461A4 (en) | 2014-01-15 | 2017-08-23 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having immunity induction activity, and immunity induction activator |
| US10322173B2 (en) | 2014-01-15 | 2019-06-18 | Shin Nippon Biomedical Laboratories, Ltd. | Chiral nucleic acid adjuvant having anti-allergic activity, and anti-allergic agent |
| KR102423317B1 (ko) | 2014-01-16 | 2022-07-22 | 웨이브 라이프 사이언시스 리미티드 | 키랄 디자인 |
| AU2017368050A1 (en) | 2016-11-29 | 2019-06-20 | Puretech Lyt, Inc. | Exosomes for delivery of therapeutic agents |
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| FR1361393A (fr) | 1963-03-29 | 1964-05-22 | Rit Rech Ind Therapeut | Dérivés d'antibiotiques basiques et leur procédé de préparation |
| US3897412A (en) | 1972-05-04 | 1975-07-29 | Bristol Myers Co | Paromomycin antibiotic derivatives |
| JPS5632999B2 (enExample) | 1972-05-04 | 1981-07-31 | ||
| US3896106A (en) | 1972-06-26 | 1975-07-22 | Bristol Myers Co | Antibiotic derivatives |
| US3808198A (en) | 1972-09-07 | 1974-04-30 | Bristol Myers Co | Lividomycin b derivatives |
| FR2209546B1 (enExample) * | 1972-12-06 | 1977-09-02 | Bristol Myers Co | |
| US3860574A (en) | 1972-12-06 | 1975-01-14 | Bristol Myers Co | Derivatives of neomycin b and neomycin c |
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| JPS553358B2 (enExample) | 1973-03-13 | 1980-01-24 | ||
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2006
- 2006-12-01 AU AU2006320374A patent/AU2006320374B2/en not_active Ceased
- 2006-12-01 EP EP06844751.5A patent/EP1957507B1/en active Active
- 2006-12-01 CA CA002632968A patent/CA2632968A1/en not_active Abandoned
- 2006-12-01 ES ES06844751T patent/ES2707787T3/es active Active
- 2006-12-01 JP JP2008543517A patent/JP5256043B2/ja active Active
- 2006-12-01 WO PCT/US2006/046122 patent/WO2007064954A2/en not_active Ceased
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2008
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2011
- 2011-01-10 US US12/987,842 patent/US8114856B2/en active Active
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2012
- 2012-01-05 US US13/344,247 patent/US8569264B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20130005674A1 (en) | 2013-01-03 |
| WO2007064954A3 (en) | 2007-08-16 |
| US8569264B2 (en) | 2013-10-29 |
| US8114856B2 (en) | 2012-02-14 |
| JP2009519243A (ja) | 2009-05-14 |
| WO2007064954A2 (en) | 2007-06-07 |
| EP1957507A2 (en) | 2008-08-20 |
| ES2707787T3 (es) | 2019-04-05 |
| AU2006320374A1 (en) | 2007-06-07 |
| AU2006320374B2 (en) | 2012-08-30 |
| US7893039B2 (en) | 2011-02-22 |
| US20080293649A1 (en) | 2008-11-27 |
| US20110166334A1 (en) | 2011-07-07 |
| JP5256043B2 (ja) | 2013-08-07 |
| EP1957507B1 (en) | 2018-10-24 |
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| FZDE | Discontinued |
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