NO322083B1 - Nye antibakterielle forbindelser, farmasoytisk akseptable forbindelser av disse, anvendelse ved fremstilling av et medikament, fremgangsmate for fremstilling, samt mikroorganisme. - Google Patents

Info

Publication number

NO322083B1

NO322083B1 NO20010105A NO20010105A NO322083B1 NO 322083 B1 NO322083 B1 NO 322083B1 NO 20010105 A NO20010105 A NO 20010105A NO 20010105 A NO20010105 A NO 20010105A NO 322083 B1 NO322083 B1 NO 322083B1

Authority

NO

Norway

Prior art keywords

group

hydrogen atom

compound

methyl group

methyl

Prior art date

1998-07-09

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 580
• 244000005700 microbiome Species 0.000 title claims abstract description 33
• 239000003814 drug Substances 0.000 title claims abstract description 21
• 238000000034 method Methods 0.000 title claims description 112
• 238000002360 preparation method Methods 0.000 title claims description 31
• 238000004519 manufacturing process Methods 0.000 title claims description 16
• 229940079593 drug Drugs 0.000 title description 10
• 230000000844 anti-bacterial effect Effects 0.000 title description 4
• 150000001408 amides Chemical class 0.000 claims abstract description 39
• 238000011282 treatment Methods 0.000 claims abstract description 15
• 241000187747 Streptomyces Species 0.000 claims abstract description 14
• 230000002265 prevention Effects 0.000 claims abstract description 11
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 9
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 250
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 216
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 154
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 126
• -1 ether compound Chemical class 0.000 claims description 99
• 150000003839 salts Chemical class 0.000 claims description 90
• PURGDQCDJJEGGD-PTRINMDFSA-N methyl (2s,3s,4s)-2-[(1r)-2-amino-1-[(2s,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-3,4-dihydro-2h-pyran-6-carboxylate Chemical compound O([C@H]([C@H]1O[C@H]([C@H](O)[C@@H]1OC)N1C(NC(=O)C=C1)=O)C(N)=O)[C@H]1OC(C(=O)OC)=C[C@H](O)[C@@H]1O PURGDQCDJJEGGD-PTRINMDFSA-N 0.000 claims description 49
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 47
• 150000002148 esters Chemical class 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 241000187392 Streptomyces griseus Species 0.000 claims description 18
• 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 17
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
• 230000008569 process Effects 0.000 claims description 10
• 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
• 125000005935 hexyloxycarbonyl group Chemical group 0.000 claims description 8
• 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000001033 ether group Chemical group 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 3
• 238000002955 isolation Methods 0.000 claims description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• 238000012786 cultivation procedure Methods 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 255
• IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 196
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• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 130
• 239000000126 substance Substances 0.000 description 129
• 239000000047 product Substances 0.000 description 122
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• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 108
• 229910001868 water Inorganic materials 0.000 description 90
• 239000002904 solvent Substances 0.000 description 88
• 239000000203 mixture Substances 0.000 description 84
• 239000000243 solution Substances 0.000 description 84
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• 238000010521 absorption reaction Methods 0.000 description 76
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 74
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
• 239000000843 powder Substances 0.000 description 60
• 239000002609 medium Substances 0.000 description 57
• 238000004128 high performance liquid chromatography Methods 0.000 description 55
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
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• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 47
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
• 230000014759 maintenance of location Effects 0.000 description 46
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 34
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
• 230000002829 reductive effect Effects 0.000 description 34
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• 238000011218 seed culture Methods 0.000 description 33
• 239000008367 deionised water Substances 0.000 description 30
• 229910021641 deionized water Inorganic materials 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 30
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
• 239000012442 inert solvent Substances 0.000 description 26
• 239000013543 active substance Substances 0.000 description 25
• 150000002170 ethers Chemical class 0.000 description 25
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 24
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 239000012153 distilled water Substances 0.000 description 24
• 239000000706 filtrate Substances 0.000 description 24
• 230000003287 optical effect Effects 0.000 description 24
• 230000035484 reaction time Effects 0.000 description 23
• RVEJXOKUHHMFKS-BPJITGRLSA-N (2s,3s,4s)-2-[(1r)-2-amino-1-[(2s,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-n-[(3s,7r)-7-methyl-2-oxoazepan-3-yl]-3,4-dihydro-2h-pyran-6-carboxamide Chemical compound O([C@@H]([C@H]([C@@H](O)C=1)O)O[C@H]([C@H]2O[C@H]([C@H](O)[C@@H]2OC)N2C(NC(=O)C=C2)=O)C(N)=O)C=1C(=O)N[C@H]1CCC[C@@H](C)NC1=O RVEJXOKUHHMFKS-BPJITGRLSA-N 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
• 125000006239 protecting group Chemical group 0.000 description 22
• 238000000746 purification Methods 0.000 description 22
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 21
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
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• 239000007864 aqueous solution Substances 0.000 description 20
• 238000001514 detection method Methods 0.000 description 20
• 238000004949 mass spectrometry Methods 0.000 description 20
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• 239000002585 base Substances 0.000 description 19
• 238000004440 column chromatography Methods 0.000 description 19
• 238000005194 fractionation Methods 0.000 description 19
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 239000002198 insoluble material Substances 0.000 description 17
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
• 239000002253 acid Substances 0.000 description 16
• 238000001914 filtration Methods 0.000 description 16
• 239000001963 growth medium Substances 0.000 description 16
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 229910052757 nitrogen Inorganic materials 0.000 description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
• YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 13
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 13
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
• 238000012360 testing method Methods 0.000 description 13
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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• 150000001298 alcohols Chemical class 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 238000010828 elution Methods 0.000 description 12
• 150000008282 halocarbons Chemical class 0.000 description 12
• 229930195733 hydrocarbon Natural products 0.000 description 12
• 150000002430 hydrocarbons Chemical class 0.000 description 12
• 239000003960 organic solvent Substances 0.000 description 12
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• 229920001817 Agar Polymers 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 238000005273 aeration Methods 0.000 description 11
• 239000008272 agar Substances 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 238000001953 recrystallisation Methods 0.000 description 11
• 238000003756 stirring Methods 0.000 description 11
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 10
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• 235000010419 agar Nutrition 0.000 description 10
• 235000008504 concentrate Nutrition 0.000 description 10
• 239000012141 concentrate Substances 0.000 description 10
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• 238000004108 freeze drying Methods 0.000 description 10
• 230000007062 hydrolysis Effects 0.000 description 10
• 238000006460 hydrolysis reaction Methods 0.000 description 10
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• 230000001954 sterilising effect Effects 0.000 description 10
• 238000004659 sterilization and disinfection Methods 0.000 description 10
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• 230000015572 biosynthetic process Effects 0.000 description 9
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• BISOEENGZHMDEO-RLXIHFJVSA-N (2s,3s,4s)-2-[(1r)-2-amino-1-[(2s,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-n-[(3s)-2-oxoazepan-3-yl]-3,4-dihydro-2h-pyran-6-carboxamide Chemical compound O([C@@H]([C@H]([C@@H](O)C=1)O)O[C@H]([C@H]2O[C@H]([C@H](O)[C@@H]2OC)N2C(NC(=O)C=C2)=O)C(N)=O)C=1C(=O)N[C@H]1CCCCNC1=O BISOEENGZHMDEO-RLXIHFJVSA-N 0.000 description 8
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• 241000894006 Bacteria Species 0.000 description 6
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• 229910019142 PO4 Inorganic materials 0.000 description 6
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• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 6
• 230000003115 biocidal effect Effects 0.000 description 6
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
• XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
• 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 6
• 235000012054 meals Nutrition 0.000 description 6
• 150000002825 nitriles Chemical class 0.000 description 6
• 150000007524 organic acids Chemical class 0.000 description 6
• 235000005985 organic acids Nutrition 0.000 description 6
• 235000021317 phosphate Nutrition 0.000 description 6
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