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

Nye antibakterielle forbindelser, farmasoytisk akseptable forbindelser av disse, anvendelse ved fremstilling av et medikament, fremgangsmate for fremstilling, samt mikroorganisme. Download PDF

Info

Publication number: NO322083B1
Authority: NO; Norway
Prior art keywords: group; hydrogen atom; compound; methyl group; methyl
Prior art date: 1998-07-09

Application number

NO20010105A

Other languages

English (en)

Norwegian (no)

Other versions

NO20010105D0 (no

NO20010105L (no

Inventor

Hitoshi Hotoda

Masatoshi Inukai

Toshio Takatsu

Masatoshi Arai

Shunichi Miyakoshi

Masaaki Kizuka

Yasumasa Ogawa

Masakatsu Kaneko

Original Assignee

Sankyo Co

Priority date (The priority date 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 date listed.)

1998-07-09

Filing date

2001-01-08

Publication date

2006-08-14

2001-01-08 Application filed by Sankyo Co filed Critical Sankyo Co

2001-01-08 Publication of NO20010105D0 publication Critical patent/NO20010105D0/no

2001-03-08 Publication of NO20010105L publication Critical patent/NO20010105L/no

2006-08-14 Publication of NO322083B1 publication Critical patent/NO322083B1/no

Links

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
238000006243 chemical reaction Methods 0.000 description 138
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 138
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 130
239000000126 substance Substances 0.000 description 129
239000000047 product Substances 0.000 description 122
238000000862 absorption spectrum Methods 0.000 description 120
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 115
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
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239000002904 solvent Substances 0.000 description 88
239000000203 mixture 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
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
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
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
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 21
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
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
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
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
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
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SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
235000010419 agar Nutrition 0.000 description 10
235000008504 concentrate Nutrition 0.000 description 10
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238000001035 drying Methods 0.000 description 10
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230000007062 hydrolysis Effects 0.000 description 10
238000006460 hydrolysis reaction Methods 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
230000001954 sterilising effect Effects 0.000 description 10
238000004659 sterilization and disinfection Methods 0.000 description 10
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
238000005886 esterification reaction Methods 0.000 description 9
230000003472 neutralizing effect Effects 0.000 description 9
238000001226 reprecipitation Methods 0.000 description 9
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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239000003463 adsorbent Substances 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 8
230000032050 esterification Effects 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
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230000000996 additive effect Effects 0.000 description 7
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235000015097 nutrients Nutrition 0.000 description 7
239000008107 starch Substances 0.000 description 7
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150000003462 sulfoxides Chemical class 0.000 description 7
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125000005118 N-alkylcarbamoyl group Chemical class 0.000 description 6
229910019142 PO4 Inorganic materials 0.000 description 6
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
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
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235000021317 phosphate Nutrition 0.000 description 6
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238000010992 reflux Methods 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
229960001225 rifampicin Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000005070 sampling Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
238000007873 sieving Methods 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000012916 structural analysis Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
FEQPHYCEZKWPNE-UHFFFAOYSA-K trichlororhodium;triphenylphosphane Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FEQPHYCEZKWPNE-UHFFFAOYSA-K 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
241001446247 uncultured actinomycete Species 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
- C12P17/162—Heterorings having oxygen atoms as the only ring heteroatoms, e.g. Lasalocid
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
- C12P17/167—Heterorings having sulfur atoms as ring heteroatoms, e.g. vitamin B1, thiamine nucleus and open chain analogs
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/38—Nucleosides
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/38—Nucleosides
- C12P19/40—Nucleosides having a condensed ring system containing a six-membered ring having two nitrogen atoms in the same ring, e.g. purine nucleosides
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
Microbiology (AREA)
Molecular Biology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Oncology (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Saccharide Compounds (AREA)

NO20010105A 1998-07-09 2001-01-08 Nye antibakterielle forbindelser, farmasoytisk akseptable forbindelser av disse, anvendelse ved fremstilling av et medikament, fremgangsmate for fremstilling, samt mikroorganisme. NO322083B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP19428598		1998-07-09
JP26944598		1998-09-24
PCT/JP1999/003718 WO2000002892A1 (en)	1998-07-09	1999-07-09	Novel antibacterial compounds

Publications (3)

Publication Number	Publication Date
NO20010105D0 NO20010105D0 (no)	2001-01-08
NO20010105L NO20010105L (no)	2001-03-08
NO322083B1 true NO322083B1 (no)	2006-08-14

Family

ID=26508414

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20010105A NO322083B1 (no)	1998-07-09	2001-01-08	Nye antibakterielle forbindelser, farmasoytisk akseptable forbindelser av disse, anvendelse ved fremstilling av et medikament, fremgangsmate for fremstilling, samt mikroorganisme.

Country Status (23)

Country	Link
US (2)	US6472384B1 (zh)
EP (3)	EP1319406A1 (zh)
KR (2)	KR100622889B1 (zh)
CN (1)	CN1181087C (zh)
AT (2)	ATE304548T1 (zh)
AU (1)	AU751470B2 (zh)
BR (1)	BR9911965A (zh)
CA (1)	CA2337225C (zh)
DE (2)	DE69935513T2 (zh)
DK (2)	DK1095947T3 (zh)
ES (2)	ES2284260T3 (zh)
HK (2)	HK1053063A1 (zh)
HU (1)	HUP0103711A3 (zh)
ID (1)	ID27955A (zh)
IL (3)	IL140731A0 (zh)
NO (1)	NO322083B1 (zh)
NZ (1)	NZ509233A (zh)
PL (1)	PL200426B1 (zh)
PT (1)	PT1095947E (zh)
RU (1)	RU2209210C2 (zh)
TR (1)	TR200100059T2 (zh)
WO (1)	WO2000002892A1 (zh)
ZA (1)	ZA200100200B (zh)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI245047B (en)	1999-08-20	2005-12-11	Sankyo Co	Novel A-500359 derivatives
EP1322504A1 (de)	2000-09-25	2003-07-02	Volkswagen AG	Airbagvorrichtung und betriebsverfahren dafür
US7652039B2 (en) *	2002-05-17	2010-01-26	Sequella, Inc.	Methods of use and compositions for the diagnosis and treatment of infectious disease
US20040033986A1 (en) *	2002-05-17	2004-02-19	Protopopova Marina Nikolaevna	Anti tubercular drug: compositions and methods
US7456222B2 (en) *	2002-05-17	2008-11-25	Sequella, Inc.	Anti tubercular drug: compositions and methods
EP1670314A4 (en) *	2003-09-05	2009-02-25	Sequella Inc	METHODS AND COMPOSITIONS INCLUDE DIAMINE AS A NEW THERAPEUTIC FOR TUBERCULOSIS
EP1771435A4 (en) *	2004-06-19	2008-02-13	Human Biomolecular Res Inst	MODULATORS OF NEUROTRANSMITTERS OF THE CENTRAL NERVOUS SYSTEM
US20090068325A1 (en) *	2007-09-10	2009-03-12	Gil Depicciotto	Method of treatment of fresh produce
WO2009136965A1 (en) *	2008-05-06	2009-11-12	Sequella, Inc.	Compositions and methods comprising capuramycin analogues

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60259190A (ja) *	1984-06-06	1985-12-21	Kanto Ishi Pharma Co Ltd	新抗生物質カプラマイシン及びその製造法
US5034381A (en) *	1988-01-07	1991-07-23	Ciba-Geigy Corporation	2-(substituted amino) adenosines as antihypertensives
JPH05148293A (ja) *	1991-11-28	1993-06-15	Mect Corp	新規カプラマイシン誘導体およびその製造方法
GB9307043D0 (en)	1993-04-05	1993-05-26	Norsk Hydro As	Chemical compounds
TWI245047B (en) *	1999-08-20	2005-12-11	Sankyo Co	Novel A-500359 derivatives

1999
- 1999-07-09 ES ES99929772T patent/ES2284260T3/es not_active Expired - Lifetime
- 1999-07-09 IL IL14073199A patent/IL140731A0/xx active IP Right Grant
- 1999-07-09 EP EP03004405A patent/EP1319406A1/en not_active Withdrawn
- 1999-07-09 DK DK99929772T patent/DK1095947T3/da active
- 1999-07-09 BR BR9911965-0A patent/BR9911965A/pt active Search and Examination
- 1999-07-09 DE DE69935513T patent/DE69935513T2/de not_active Expired - Lifetime
- 1999-07-09 PT PT99929772T patent/PT1095947E/pt unknown
- 1999-07-09 DE DE69927306T patent/DE69927306T2/de not_active Expired - Lifetime
- 1999-07-09 CA CA002337225A patent/CA2337225C/en not_active Expired - Fee Related
- 1999-07-09 PL PL345403A patent/PL200426B1/pl not_active IP Right Cessation
- 1999-07-09 EP EP03004404A patent/EP1319666B1/en not_active Expired - Lifetime
- 1999-07-09 AT AT03004404T patent/ATE304548T1/de not_active IP Right Cessation
- 1999-07-09 DK DK03004404T patent/DK1319666T3/da active
- 1999-07-09 ES ES03004404T patent/ES2248654T3/es not_active Expired - Lifetime
- 1999-07-09 CN CNB998107417A patent/CN1181087C/zh not_active Expired - Fee Related
- 1999-07-09 EP EP99929772A patent/EP1095947B1/en not_active Expired - Lifetime
- 1999-07-09 NZ NZ509233A patent/NZ509233A/en not_active IP Right Cessation
- 1999-07-09 KR KR1020017000380A patent/KR100622889B1/ko not_active IP Right Cessation
- 1999-07-09 HU HU0103711A patent/HUP0103711A3/hu unknown
- 1999-07-09 WO PCT/JP1999/003718 patent/WO2000002892A1/ja active Application Filing
- 1999-07-09 RU RU2001101459/04A patent/RU2209210C2/ru not_active IP Right Cessation
- 1999-07-09 AT AT99929772T patent/ATE356825T1/de not_active IP Right Cessation
- 1999-07-09 ID IDW20010052A patent/ID27955A/id unknown
- 1999-07-09 KR KR1020067000525A patent/KR100729196B1/ko not_active IP Right Cessation
- 1999-07-09 TR TR2001/00059T patent/TR200100059T2/xx unknown
- 1999-07-09 AU AU46505/99A patent/AU751470B2/en not_active Ceased
2001
- 2001-01-04 IL IL140731A patent/IL140731A/en not_active IP Right Cessation
- 2001-01-08 NO NO20010105A patent/NO322083B1/no not_active IP Right Cessation
- 2001-01-08 ZA ZA2001/00200A patent/ZA200100200B/en unknown
- 2001-01-09 US US09/757,393 patent/US6472384B1/en not_active Expired - Lifetime
- 2001-07-04 HK HK03105384.0A patent/HK1053063A1/zh unknown
- 2001-07-04 HK HK03105386.8A patent/HK1053127B/zh not_active IP Right Cessation
2002
- 2002-03-12 US US10/096,006 patent/US6844173B2/en not_active Expired - Fee Related
2007
- 2007-11-22 IL IL187551A patent/IL187551A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
US6472384B1 (en)	2002-10-29
ES2284260T3 (es)	2007-11-01
CA2337225A1 (en)	2000-01-20
EP1095947A4 (en)	2002-01-16
AU4650599A (en)	2000-02-01
HK1053127A1 (en)	2003-10-10
CN1317008A (zh)	2001-10-10
EP1319406A1 (en)	2003-06-18
PT1095947E (pt)	2007-06-20
IL140731A0 (en)	2002-02-10
WO2000002892A1 (en)	2000-01-20
AU751470B2 (en)	2002-08-15
BR9911965A (pt)	2001-05-29
ATE356825T1 (de)	2007-04-15
KR100622889B1 (ko)	2006-09-12
CN1181087C (zh)	2004-12-22
ZA200100200B (en)	2002-06-26
HK1053063A1 (zh)	2003-10-10
RU2209210C2 (ru)	2003-07-27
KR100729196B1 (ko)	2007-06-19
EP1319666A1 (en)	2003-06-18
NZ509233A (en)	2003-05-30
PL345403A1 (en)	2001-12-17
HK1053127B (zh)	2005-12-30
IL187551A (en)	2009-12-24
EP1095947B1 (en)	2007-03-14
DE69935513T2 (de)	2007-11-29
HUP0103711A3 (en)	2003-11-28
IL140731A (en)	2008-06-05
ES2248654T3 (es)	2006-03-16
CA2337225C (en)	2009-05-26
DK1095947T3 (da)	2007-07-16
EP1319666B1 (en)	2005-09-14
NO20010105D0 (no)	2001-01-08
PL200426B1 (pl)	2009-01-30
DE69927306D1 (de)	2005-10-20
US6844173B2 (en)	2005-01-18
IL187551A0 (en)	2008-03-20
KR20060011919A (ko)	2006-02-03
DE69935513D1 (de)	2007-04-26
ID27955A (id)	2001-05-03
HUP0103711A2 (hu)	2002-02-28
ATE304548T1 (de)	2005-09-15
NO20010105L (no)	2001-03-08
DE69927306T2 (de)	2006-07-06
KR20010083101A (ko)	2001-08-31
TR200100059T2 (tr)	2001-05-21
DK1319666T3 (da)	2005-12-05
US20030069204A1 (en)	2003-04-10
EP1095947A1 (en)	2001-05-02

Publication	Publication Date	Title
JPH06247894A (ja)	1994-09-06	エステル誘導体
NO322083B1 (no)	2006-08-14	Nye antibakterielle forbindelser, farmasoytisk akseptable forbindelser av disse, anvendelse ved fremstilling av et medikament, fremgangsmate for fremstilling, samt mikroorganisme.
KR100226305B1 (ko)	1999-10-15	폴리히드록시 시클로펜탄유도체, 그의 제조방법 및 그의 치료적용도
US7166634B2 (en)	2007-01-23	Bis-indole pyrroles useful as antimicrobials agents
JP4960548B2 (ja)	2012-06-27	新規抗細菌化合物の用途
JP4531167B2 (ja)	2010-08-25	新規抗細菌化合物
JP5619001B2 (ja)	2014-11-05	ストレプトスピロール誘導体
AU764109B2 (en)	2003-08-07	Novel antibacterial compounds
EP1237866B1 (en)	2005-06-29	Amycomycin, a process for its production and its use as a pharmaceutical
JP2000169495A (ja)	2000-06-20	糖脂質、その製造法および用途
MXPA01000375A (en)	2001-09-07	Novel antibacterial compounds

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2011-02-28	MM1K	Lapsed by not paying the annual fees