KR20150105300A - 신규 항균 화합물 및 이들의 생물학적 용도 - Google Patents
신규 항균 화합물 및 이들의 생물학적 용도 Download PDFInfo
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- KR20150105300A KR20150105300A KR1020157014444A KR20157014444A KR20150105300A KR 20150105300 A KR20150105300 A KR 20150105300A KR 1020157014444 A KR1020157014444 A KR 1020157014444A KR 20157014444 A KR20157014444 A KR 20157014444A KR 20150105300 A KR20150105300 A KR 20150105300A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 246
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 99
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 59
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 239000002253 acid Substances 0.000 claims abstract description 30
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 13
- 150000007513 acids Chemical class 0.000 claims abstract description 11
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 229940079593 drug Drugs 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 230000015788 innate immune response Effects 0.000 claims abstract description 5
- -1 cyclic hemiacetal Chemical class 0.000 claims description 190
- 238000006243 chemical reaction Methods 0.000 claims description 123
- 239000000203 mixture Substances 0.000 claims description 82
- 238000002360 preparation method Methods 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 32
- 230000015572 biosynthetic process Effects 0.000 claims description 30
- 125000006239 protecting group Chemical group 0.000 claims description 20
- 150000002923 oximes Chemical class 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- 241000894006 Bacteria Species 0.000 claims description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 238000006366 phosphorylation reaction Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- FBPFZTCFMRRESA-OMMKOOBNSA-N L-altritol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@@H](O)CO FBPFZTCFMRRESA-OMMKOOBNSA-N 0.000 claims description 6
- 238000005917 acylation reaction Methods 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- LBJFEFHCTYMJFD-JKUQZMGJSA-N [(2r,3s,4s)-5-[formyl(hydroxy)amino]-2,3,4-trihydroxypentyl] dihydrogen phosphate Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN(O)C=O LBJFEFHCTYMJFD-JKUQZMGJSA-N 0.000 claims description 5
- 238000006555 catalytic reaction Methods 0.000 claims description 5
- 238000005755 formation reaction Methods 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 230000026731 phosphorylation Effects 0.000 claims description 5
- 238000006722 reduction reaction Methods 0.000 claims description 5
- 101000805864 Homo sapiens Divergent protein kinase domain 2A Proteins 0.000 claims description 4
- 101000998623 Homo sapiens NADH-cytochrome b5 reductase 3 Proteins 0.000 claims description 4
- 101000928408 Homo sapiens Protein diaphanous homolog 2 Proteins 0.000 claims description 4
- 238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 claims description 4
- 102100033153 NADH-cytochrome b5 reductase 3 Human genes 0.000 claims description 4
- 102100036469 Protein diaphanous homolog 2 Human genes 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000006268 reductive amination reaction Methods 0.000 claims description 4
- 108010028921 Lipopeptides Proteins 0.000 claims description 3
- 229930189077 Rifamycin Natural products 0.000 claims description 3
- 108010034396 Streptogramins Proteins 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000005906 dihydroxylation reaction Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000026030 halogenation Effects 0.000 claims description 3
- 238000005658 halogenation reaction Methods 0.000 claims description 3
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 3
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 3
- 229940041033 macrolides Drugs 0.000 claims description 3
- 238000005649 metathesis reaction Methods 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 claims description 3
- 229940081192 rifamycins Drugs 0.000 claims description 3
- 229940041030 streptogramins Drugs 0.000 claims description 3
- 230000007704 transition Effects 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 238000007014 Michaelis-Becker reaction Methods 0.000 claims description 2
- JVWLUVNSQYXYBE-UHFFFAOYSA-N Ribitol Natural products OCC(C)C(O)C(O)CO JVWLUVNSQYXYBE-UHFFFAOYSA-N 0.000 claims description 2
- OMYWYTPGDNNIDC-KTUCCBJNSA-N [(3r,4r,5s)-6-[formyl(hydroxy)amino]-3,4,5,7-tetrahydroxyheptyl]phosphonic acid Chemical compound O=CN(O)C(CO)[C@H](O)[C@H](O)[C@H](O)CCP(O)(O)=O OMYWYTPGDNNIDC-KTUCCBJNSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 150000001298 alcohols Chemical group 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 230000009435 amidation Effects 0.000 claims description 2
- 238000007112 amidation reaction Methods 0.000 claims description 2
- 150000001412 amines Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 230000020335 dealkylation Effects 0.000 claims description 2
- 238000006900 dealkylation reaction Methods 0.000 claims description 2
- 238000005695 dehalogenation reaction Methods 0.000 claims description 2
- 238000006392 deoxygenation reaction Methods 0.000 claims description 2
- 238000006735 epoxidation reaction Methods 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 238000005954 phosphonylation reaction Methods 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 230000006103 sulfonylation Effects 0.000 claims description 2
- 238000005694 sulfonylation reaction Methods 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical group 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 3
- VNMFURBRXFDBRC-JKUQZMGJSA-N [(2s,3s,4s)-5-[formyl(hydroxy)amino]-2,3,4-trihydroxypentyl]phosphonic acid Chemical compound O=CN(O)C[C@H](O)[C@H](O)[C@H](O)CP(O)(O)=O VNMFURBRXFDBRC-JKUQZMGJSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 abstract description 3
- 239000004599 antimicrobial Substances 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 293
- 238000005481 NMR spectroscopy Methods 0.000 description 203
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
- 239000000243 solution Substances 0.000 description 172
- 239000011541 reaction mixture Substances 0.000 description 153
- 235000019439 ethyl acetate Nutrition 0.000 description 127
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 121
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 120
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 116
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 84
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 75
- 230000002829 reductive effect Effects 0.000 description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 239000000741 silica gel Substances 0.000 description 63
- 229910002027 silica gel Inorganic materials 0.000 description 63
- 206010057190 Respiratory tract infections Diseases 0.000 description 54
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
- 239000012230 colorless oil Substances 0.000 description 47
- 238000004809 thin layer chromatography Methods 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000003480 eluent Substances 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- 239000011734 sodium Substances 0.000 description 39
- 239000000047 product Substances 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000002158 endotoxin Substances 0.000 description 34
- 229920006008 lipopolysaccharide Polymers 0.000 description 34
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 30
- 238000003556 assay Methods 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 238000004587 chromatography analysis Methods 0.000 description 26
- 238000000132 electrospray ionisation Methods 0.000 description 26
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
- 229920006395 saturated elastomer Polymers 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 239000007864 aqueous solution Substances 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 22
- 239000002585 base Substances 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 239000012298 atmosphere Substances 0.000 description 19
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 241000588724 Escherichia coli Species 0.000 description 18
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 18
- 239000007983 Tris buffer Substances 0.000 description 17
- 230000001580 bacterial effect Effects 0.000 description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 16
- 229910004298 SiO 2 Inorganic materials 0.000 description 15
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 15
- 238000002013 hydrophilic interaction chromatography Methods 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tertiry butyl alcohol Natural products CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000012267 brine Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 230000000670 limiting effect Effects 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 13
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- 235000011054 acetic acid Nutrition 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 150000002386 heptoses Chemical class 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 9
- 0 CC(C)C(N(*)*)=C(C)C Chemical compound CC(C)C(N(*)*)=C(C)C 0.000 description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 8
- HWTGSIHSDQGXAV-DSYKOEDSSA-N [(3r,4r,5s)-6-[formyl(hydroxy)amino]-3,4,5-trihydroxyhexyl]phosphonic acid Chemical compound OP(=O)(O)CC[C@@H](O)[C@@H](O)[C@@H](O)CN(O)C=O HWTGSIHSDQGXAV-DSYKOEDSSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
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- 235000019253 formic acid Nutrition 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 229940088710 antibiotic agent Drugs 0.000 description 7
- 150000001720 carbohydrates Chemical class 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- 235000014633 carbohydrates Nutrition 0.000 description 6
- 239000013256 coordination polymer Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 238000010186 staining Methods 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
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- A61K31/66—Phosphorus compounds
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
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- Epidemiology (AREA)
- Molecular Biology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Emergency Medicine (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12306350.5A EP2725029A1 (en) | 2012-10-29 | 2012-10-29 | New antibacterial compounds and biological applications thereof |
| EP12306350.5 | 2012-10-29 | ||
| PCT/EP2013/072526 WO2014067904A1 (en) | 2012-10-29 | 2013-10-28 | New antibacterial compounds and biological applications thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150105300A true KR20150105300A (ko) | 2015-09-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157014444A Withdrawn KR20150105300A (ko) | 2012-10-29 | 2013-10-28 | 신규 항균 화합물 및 이들의 생물학적 용도 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9975911B2 (https=) |
| EP (2) | EP2725029A1 (https=) |
| JP (1) | JP6389463B2 (https=) |
| KR (1) | KR20150105300A (https=) |
| CN (1) | CN104936966A (https=) |
| AU (1) | AU2013339557A1 (https=) |
| BR (1) | BR112015009546A2 (https=) |
| CA (1) | CA2889503A1 (https=) |
| CL (1) | CL2015000985A1 (https=) |
| HK (1) | HK1211034A1 (https=) |
| MX (1) | MX2015005498A (https=) |
| RU (1) | RU2015120376A (https=) |
| WO (1) | WO2014067904A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102282155B (zh) | 2008-12-02 | 2017-06-09 | 日本波涛生命科学公司 | 磷原子修饰的核酸的合成方法 |
| RU2612521C2 (ru) | 2009-07-06 | 2017-03-09 | Онтории, Инк. | Новые пролекарства нуклеиновых кислот и способы их применения |
| JP5868324B2 (ja) | 2010-09-24 | 2016-02-24 | 株式会社Wave Life Sciences Japan | 不斉補助基 |
| CN103796657B (zh) | 2011-07-19 | 2017-07-11 | 波涛生命科学有限公司 | 合成官能化核酸的方法 |
| PL2872485T3 (pl) | 2012-07-13 | 2021-05-31 | Wave Life Sciences Ltd. | Asymetryczna grupa pomocnicza |
| BR112016016400A2 (pt) | 2014-01-16 | 2017-10-03 | Wave Life Sciences Ltd | Composições de oligonucleotídeos quiralmente controlados, seu uso, sua composição farmacêutica, e métodos |
| CN108484619A (zh) * | 2018-04-26 | 2018-09-04 | 福建师范大学泉港石化研究院 | 一种罗丹明基Fe3+荧光探针及其制备方法 |
| CN108484620A (zh) * | 2018-04-26 | 2018-09-04 | 福建师范大学泉港石化研究院 | 一种水溶性罗丹明基Cu2+荧光探针及其合成方法 |
| US11905286B2 (en) | 2018-08-09 | 2024-02-20 | Antabio Sas | Diazabicyclooctanones as inhibitors of serine beta-lactamases |
| SG11202101255UA (en) | 2018-08-09 | 2021-03-30 | Antabio Sas | Diazabicyclooctanones as inhibitors of serine beta-lactamases |
| RU2770537C1 (ru) * | 2021-09-15 | 2022-04-18 | федеральное государственное автономное образовательное учреждение высшего образования «Казанский (Приволжский) федеральный университет» (ФГАОУ ВО КФУ) | Фосфорилсодержащие четвертичные соли аммония с высшими алкильными заместителями, обладающие бактерицидной и фунгицидной активностью |
| CN116905145B (zh) * | 2023-08-07 | 2026-03-06 | 安徽恒益智能科技股份有限公司 | 一种抗菌包芯纱线及其制备方法 |
Family Cites Families (19)
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| US4206156A (en) * | 1976-07-27 | 1980-06-03 | Fujisawa Pharmaceutical Company, Limited | Hydroxyaminohydrocarbonphosphonic acids |
| GB1580899A (en) | 1976-07-27 | 1980-12-10 | Fujisawa Pharmaceutical Co | Hydroxyaminohydrocarbonphosphonic acid derivatives and production and use thereof |
| JPS5463024A (en) * | 1977-10-27 | 1979-05-21 | Fujisawa Pharmaceut Co Ltd | 3-(n-formyl-n-hydroxyamino)-2(r)-hydroxypropyl-phosphonic acid, its preparation, and its use |
| JPS5562019A (en) * | 1978-09-14 | 1980-05-10 | Fujisawa Pharmaceut Co Ltd | Antibacterial |
| US4693742A (en) | 1983-12-20 | 1987-09-15 | Rohm And Hass Company | Herbicidal hydroxyamino phosphonic acids and derivatives |
| CA1340588C (en) | 1988-06-13 | 1999-06-08 | Balraj Krishan Handa | Amino acid derivatives |
| US6949528B1 (en) | 1998-03-18 | 2005-09-27 | Goddard John G | Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof |
| BR9912062A (pt) * | 1998-07-15 | 2001-04-03 | Hassan Jomaa | Compostos orgânicos fosforosos e seu uso |
| US6911450B1 (en) | 2001-01-29 | 2005-06-28 | Universite De Geneve | Pyrimidine acyclonucleoside derivatives, preparation method and use thereof |
| FR2872158B1 (fr) | 2004-06-28 | 2006-11-03 | Merck Sante Soc Par Actions Si | Nouveaux composes diazeniumdiolates, leur procede de preparation et leur utilisation therapeutique |
| EP1669365A1 (en) | 2004-12-03 | 2006-06-14 | Mutabilis SA | Method for preparing enzymatic substrate analogs as inhibitors of bacterial heptosyl-transferases |
| WO2008033747A2 (en) | 2006-09-11 | 2008-03-20 | Curis, Inc. | Multi-functional small molecules as anti-proliferative agents |
| AU2007301607A1 (en) | 2006-09-25 | 2008-04-03 | Mutabilis Sa | Substituted heterocyclylcarbonylamino-acetic-acid-derivatives as inhibitors of bacterial heptose synthesis, methods for their preparation and biological applications of said inhibitors |
| EP2141164A1 (en) | 2008-07-01 | 2010-01-06 | Mutabilis | New 1,2,4-triazine derivatives and biological applications thereof |
| HRP20150778T1 (hr) * | 2009-01-23 | 2015-08-28 | Euro-Celtique S.A. | Derivati hidroksamske kiseline |
| WO2011045703A2 (en) | 2009-10-13 | 2011-04-21 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| EP2377853A1 (en) | 2010-04-09 | 2011-10-19 | Universite de Rouen | 7,11-Methanocycloocta[b]quinoline derivative as highly functionalizable acetylcholinesterase inhibitors |
| EP2646451A2 (en) | 2010-12-01 | 2013-10-09 | Laboratoire Biodim | Heptose derivatives for use in the treatment of bacterial infections |
| US9593136B2 (en) * | 2011-07-01 | 2017-03-14 | The George Washington University | Compounds for inhibiting 1-deoxy-D-xylulose-5-phosphate reductoisomerase |
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2012
- 2012-10-29 EP EP12306350.5A patent/EP2725029A1/en not_active Withdrawn
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2013
- 2013-04-28 BR BR112015009546A patent/BR112015009546A2/pt not_active IP Right Cessation
- 2013-10-28 CA CA2889503A patent/CA2889503A1/en not_active Abandoned
- 2013-10-28 JP JP2015538485A patent/JP6389463B2/ja not_active Expired - Fee Related
- 2013-10-28 AU AU2013339557A patent/AU2013339557A1/en not_active Abandoned
- 2013-10-28 CN CN201380064824.9A patent/CN104936966A/zh active Pending
- 2013-10-28 HK HK15111841.1A patent/HK1211034A1/xx unknown
- 2013-10-28 US US14/438,929 patent/US9975911B2/en active Active - Reinstated
- 2013-10-28 MX MX2015005498A patent/MX2015005498A/es unknown
- 2013-10-28 WO PCT/EP2013/072526 patent/WO2014067904A1/en not_active Ceased
- 2013-10-28 KR KR1020157014444A patent/KR20150105300A/ko not_active Withdrawn
- 2013-10-28 EP EP13783572.4A patent/EP2912043B1/en not_active Not-in-force
- 2013-10-28 RU RU2015120376A patent/RU2015120376A/ru unknown
-
2015
- 2015-04-17 CL CL2015000985A patent/CL2015000985A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014067904A1 (en) | 2014-05-08 |
| EP2912043B1 (en) | 2016-11-30 |
| AU2013339557A1 (en) | 2015-04-30 |
| MX2015005498A (es) | 2016-01-08 |
| EP2912043A1 (en) | 2015-09-02 |
| US20150291636A1 (en) | 2015-10-15 |
| HK1211034A1 (en) | 2016-05-13 |
| US9975911B2 (en) | 2018-05-22 |
| JP2015536928A (ja) | 2015-12-24 |
| BR112015009546A2 (pt) | 2017-07-04 |
| RU2015120376A (ru) | 2016-12-20 |
| JP6389463B2 (ja) | 2018-09-12 |
| EP2725029A1 (en) | 2014-04-30 |
| CA2889503A1 (en) | 2014-05-08 |
| CN104936966A (zh) | 2015-09-23 |
| CL2015000985A1 (es) | 2016-05-13 |
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