BG104995A - Производни на 2''-деокси хигромицин - Google Patents

Производни на 2''-деокси хигромицин Download PDF

Info

Publication number: BG104995A
Authority: BG; Bulgaria
Prior art keywords: methyl; oxy; oxo; amino; inositol
Prior art date: 1998-05-04

Application number

BG104995A

Other languages

Bulgarian (bg)

English (en)

Inventor

Robert Gerald Ii Linde

Original Assignee

Pfizer Products Inc.

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.)

1998-05-04

Filing date

2000-11-28

Publication date

2001-07-31

2000-11-28 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2001-07-31 Publication of BG104995A publication Critical patent/BG104995A/bg

Links

150000001875 compounds Chemical class 0.000 claims abstract description 136
238000000034 method Methods 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 39
208000035143 Bacterial infection Diseases 0.000 claims abstract description 17
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 17
239000000651 prodrug Substances 0.000 claims abstract description 17
229940002612 prodrug Drugs 0.000 claims abstract description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
239000012453 solvate Substances 0.000 claims abstract description 6
150000002923 oximes Chemical class 0.000 claims description 297
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 275
-1 nitro, difluoromethoxy Chemical group 0.000 claims description 215
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 213
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 212
229960000367 inositol Drugs 0.000 claims description 112
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
125000000623 heterocyclic group Chemical group 0.000 claims description 53
125000003118 aryl group Chemical group 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 24
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical group [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 24
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 12
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
230000000903 blocking effect Effects 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 10
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 10
241000251468 Actinopterygii Species 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
125000004434 sulfur atom Chemical group 0.000 claims description 10
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims description 9
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 8
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 8
208000028172 protozoa infectious disease Diseases 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000004494 ethyl ester group Chemical group 0.000 claims description 5
150000002443 hydroxylamines Chemical class 0.000 claims description 5
229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 4
125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
239000011521 glass Substances 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000006308 propyl amino group Chemical group 0.000 claims 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
QUBJDMPBDURTJT-UHFFFAOYSA-N 3-chlorothiophene Chemical compound ClC=1C=CSC=1 QUBJDMPBDURTJT-UHFFFAOYSA-N 0.000 claims 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
NPGSSYDNCMYGPK-UHFFFAOYSA-N 6-chloro-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=CC(Cl)=CC=C21 NPGSSYDNCMYGPK-UHFFFAOYSA-N 0.000 claims 1
229910000029 sodium carbonate Inorganic materials 0.000 claims 1
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims 1
208000015181 infectious disease Diseases 0.000 abstract description 35
230000001580 bacterial effect Effects 0.000 abstract description 8
239000003242 anti bacterial agent Substances 0.000 abstract description 6
206010037075 Protozoal infections Diseases 0.000 abstract description 5
230000000844 anti-bacterial effect Effects 0.000 abstract description 4
239000003904 antiprotozoal agent Substances 0.000 abstract description 2
208000035475 disorder Diseases 0.000 abstract 1
YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 description 42
YQYJSBFKSSDGFO-FWAVGLHBSA-N hygromycin A Chemical compound O[C@H]1[C@H](O)[C@H](C(=O)C)O[C@@H]1Oc1ccc(\C=C(/C)C(=O)N[C@@H]2[C@@H]([C@H]3OCO[C@H]3[C@@H](O)[C@@H]2O)O)cc1O YQYJSBFKSSDGFO-FWAVGLHBSA-N 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
239000000243 solution Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
238000000855 fermentation Methods 0.000 description 20
230000004151 fermentation Effects 0.000 description 20
239000000872 buffer Substances 0.000 description 17
CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical compound OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
150000002576 ketones Chemical class 0.000 description 15
239000000047 product Substances 0.000 description 15
239000002585 base Substances 0.000 description 14
239000000945 filler Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
239000007787 solid Substances 0.000 description 12
238000011282 treatment Methods 0.000 description 12
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PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
235000019439 ethyl acetate Nutrition 0.000 description 9
239000000463 material Substances 0.000 description 9
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 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
239000002609 medium Substances 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
150000001732 carboxylic acid derivatives Chemical group 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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229920002472 Starch Polymers 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
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239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
241000193996 Streptococcus pyogenes Species 0.000 description 5
238000011081 inoculation Methods 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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230000009471 action Effects 0.000 description 4
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229910052784 alkaline earth metal Inorganic materials 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
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150000002243 furanoses Chemical class 0.000 description 4
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125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
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BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 4
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 3
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KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 3
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NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
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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 description 1
238000007911 parenteral administration Methods 0.000 description 1
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239000000546 pharmaceutical excipient Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000008105 phosphatidylcholines Chemical class 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
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XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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229920001610 polycaprolactone Polymers 0.000 description 1
229920002721 polycyanoacrylate Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001184 polypeptide Chemical group 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
108090000765 processed proteins & peptides Chemical group 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
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208000020029 respiratory tract infectious disease Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
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HBEFYGYBMKPNSZ-UHFFFAOYSA-N s-phenyl chloromethanethioate Chemical compound ClC(=O)SC1=CC=CC=C1 HBEFYGYBMKPNSZ-UHFFFAOYSA-N 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
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238000006884 silylation reaction Methods 0.000 description 1
239000002356 single layer Substances 0.000 description 1
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235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
208000015339 staphylococcus aureus infection Diseases 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229940115920 streptococcus dysgalactiae Drugs 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
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230000009885 systemic 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
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
238000010998 test method Methods 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001583 thiepanyl group Chemical group 0.000 description 1
125000002053 thietanyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

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
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- 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
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
- 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)
Health & Medical Sciences (AREA)
Organic Chemistry (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)
Veterinary Medicine (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)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

BG104995A 1998-05-04 2000-11-28 Производни на 2''-деокси хигромицин BG104995A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8405898P	1998-05-04	1998-05-04
PCT/IB1999/000611 WO1999057127A1 (en)	1998-05-04	1999-04-08	2'-deoxy hygromycin derivatives

Publications (1)

Publication Number	Publication Date
BG104995A true BG104995A (bg)	2001-07-31

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ID=22182624

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG104995A BG104995A (bg)	1998-05-04	2000-11-28	Производни на 2''-деокси хигромицин

Country Status (38)

Country	Link
US (1)	US6342497B1 (no)
EP (1)	EP1077984B1 (no)
JP (1)	JP2002513798A (no)
KR (1)	KR100396099B1 (no)
CN (1)	CN1299367A (no)
AP (1)	AP1069A (no)
AR (1)	AR015776A1 (no)
AT (1)	ATE243218T1 (no)
AU (1)	AU762302B2 (no)
BG (1)	BG104995A (no)
BR (1)	BR9910232A (no)
CA (1)	CA2331261C (no)
DE (1)	DE69908936T2 (no)
DK (1)	DK1077984T3 (no)
DZ (1)	DZ2779A1 (no)
EA (1)	EA004374B1 (no)
ES (1)	ES2199559T3 (no)
GT (1)	GT199900058A (no)
HN (1)	HN1999000064A (no)
HR (1)	HRP20000748A2 (no)
HU (1)	HUP0102412A3 (no)
ID (1)	ID26368A (no)
IL (1)	IL139020A0 (no)
IS (1)	IS5680A (no)
MA (1)	MA26626A1 (no)
NO (1)	NO20005551L (no)
NZ (1)	NZ507450A (no)
OA (1)	OA11507A (no)
PA (1)	PA8471901A1 (no)
PE (1)	PE20000440A1 (no)
PL (1)	PL344085A1 (no)
PT (1)	PT1077984E (no)
SK (1)	SK16442000A3 (no)
TN (1)	TNSN99084A1 (no)
TR (1)	TR200003249T2 (no)
WO (1)	WO1999057127A1 (no)
YU (1)	YU64300A (no)
ZA (1)	ZA993063B (no)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ511424A (en) *	1998-12-02	2003-08-29	Pfizer Prod Inc	Hygromycin A derivatives as antibacterial agents
GB9923078D0 (en) *	1999-09-29	1999-12-01	Phytopharm Plc	Sapogenin derivatives and their use
CZ20023859A3 (cs) *	2000-06-02	2004-02-18	Pfizer Products Inc.	Deriváty hygromycinu A pro léčení bakteriálních a protozoálních infekcí
CN102168034B (zh) *	2010-11-29	2012-12-05	中国科学院南海海洋研究所	一种海洋链霉菌以及利用该菌制备替达霉素a和b的方法
US12233081B2 (en)	2018-08-20	2025-02-25	Northeastern University	Hygromycin a compounds and methods of treating spirochete diseases

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2832356B2 (ja) *	1988-03-31	1998-12-09	武田薬品工業株式会社	ハイグロマイシン類の合成中間体および製造法

1999
- 1999-04-08 US US09/380,718 patent/US6342497B1/en not_active Expired - Fee Related
- 1999-04-08 BR BR9910232-3A patent/BR9910232A/pt not_active IP Right Cessation
- 1999-04-08 AT AT99909164T patent/ATE243218T1/de not_active IP Right Cessation
- 1999-04-08 DE DE69908936T patent/DE69908936T2/de not_active Expired - Fee Related
- 1999-04-08 PT PT99909164T patent/PT1077984E/pt unknown
- 1999-04-08 JP JP2000547096A patent/JP2002513798A/ja active Pending
- 1999-04-08 CA CA002331261A patent/CA2331261C/en not_active Expired - Fee Related
- 1999-04-08 PL PL99344085A patent/PL344085A1/xx unknown
- 1999-04-08 AU AU28508/99A patent/AU762302B2/en not_active Ceased
- 1999-04-08 ES ES99909164T patent/ES2199559T3/es not_active Expired - Lifetime
- 1999-04-08 CN CN99805810A patent/CN1299367A/zh active Pending
- 1999-04-08 SK SK1644-2000A patent/SK16442000A3/sk unknown
- 1999-04-08 TR TR2000/03249T patent/TR200003249T2/xx unknown
- 1999-04-08 ID IDW20002256A patent/ID26368A/id unknown
- 1999-04-08 KR KR10-2000-7012222A patent/KR100396099B1/ko not_active Expired - Fee Related
- 1999-04-08 EP EP99909164A patent/EP1077984B1/en not_active Expired - Lifetime
- 1999-04-08 WO PCT/IB1999/000611 patent/WO1999057127A1/en not_active Ceased
- 1999-04-08 YU YU64300A patent/YU64300A/sh unknown
- 1999-04-08 HU HU0102412A patent/HUP0102412A3/hu unknown
- 1999-04-08 EA EA200001028A patent/EA004374B1/ru not_active IP Right Cessation
- 1999-04-08 DK DK99909164T patent/DK1077984T3/da active
- 1999-04-08 NZ NZ507450A patent/NZ507450A/en unknown
- 1999-04-08 HR HR20000748A patent/HRP20000748A2/hr not_active Application Discontinuation
- 1999-04-08 IL IL13902099A patent/IL139020A0/xx unknown
- 1999-04-16 GT GT199900058A patent/GT199900058A/es unknown
- 1999-04-29 AP APAP/P/1999/001525A patent/AP1069A/en active
- 1999-04-29 PE PE1999000355A patent/PE20000440A1/es not_active Application Discontinuation
- 1999-04-30 AR ARP990102023A patent/AR015776A1/es not_active Application Discontinuation
- 1999-05-03 HN HN1999000064A patent/HN1999000064A/es unknown
- 1999-05-03 MA MA25566A patent/MA26626A1/fr unknown
- 1999-05-03 ZA ZA9903063A patent/ZA993063B/xx unknown
- 1999-05-03 DZ DZ990079A patent/DZ2779A1/xx active
- 1999-05-03 TN TNTNSN99084A patent/TNSN99084A1/fr unknown
- 1999-05-04 PA PA19998471901A patent/PA8471901A1/es unknown
2000
- 2000-10-24 IS IS5680A patent/IS5680A/is unknown
- 2000-10-27 OA OA1200000298A patent/OA11507A/en unknown
- 2000-11-03 NO NO20005551A patent/NO20005551L/no not_active Application Discontinuation
- 2000-11-28 BG BG104995A patent/BG104995A/bg unknown

Also Published As

Publication number	Publication date
DZ2779A1 (fr)	2005-04-23
KR100396099B1 (ko)	2003-08-27
AR015776A1 (es)	2001-05-16
DK1077984T3 (da)	2003-09-15
HUP0102412A2 (hu)	2001-11-28
IS5680A (is)	2000-10-24
AU2850899A (en)	1999-11-23
YU64300A (sh)	2003-07-07
SK16442000A3 (sk)	2001-07-10
HN1999000064A (es)	2000-01-12
EA200001028A1 (ru)	2001-04-23
TNSN99084A1 (fr)	2005-11-10
ZA993063B (en)	2000-11-03
BR9910232A (pt)	2001-01-09
PA8471901A1 (es)	2000-09-29
IL139020A0 (en)	2001-11-25
DE69908936T2 (de)	2004-05-19
WO1999057127A1 (en)	1999-11-11
US6342497B1 (en)	2002-01-29
HUP0102412A3 (en)	2003-07-28
PL344085A1 (en)	2001-09-24
HRP20000748A2 (en)	2001-06-30
KR20010043267A (ko)	2001-05-25
TR200003249T2 (tr)	2001-03-21
NO20005551L (no)	2001-01-02
CA2331261A1 (en)	1999-11-11
CN1299367A (zh)	2001-06-13
NO20005551D0 (no)	2000-11-03
AP1069A (en)	2002-05-14
EP1077984A1 (en)	2001-02-28
EP1077984B1 (en)	2003-06-18
DE69908936D1 (en)	2003-07-24
OA11507A (en)	2004-05-13
AP9901525A0 (en)	1999-06-30
CA2331261C (en)	2004-07-27
AU762302B2 (en)	2003-06-19
GT199900058A (es)	2000-10-07
ES2199559T3 (es)	2004-02-16
ATE243218T1 (de)	2003-07-15
PE20000440A1 (es)	2000-05-26
ID26368A (id)	2000-12-14
EA004374B1 (ru)	2004-04-29
MA26626A1 (fr)	2004-12-20
JP2002513798A (ja)	2002-05-14
PT1077984E (pt)	2003-09-30
NZ507450A (en)	2003-08-29

Publication	Publication Date	Title
US6313100B1 (en)	2001-11-06	Hygromycin derivatives
AP1069A (en)	2002-05-14	2'-Deoxy hygromycin derivatives.
AU6362799A (en)	2000-06-19	Hygromycin a derivatives as antibacterial agents
EP1369490B1 (en)	2006-02-08	Method of preparing a composition containing hygromycin A and epi-hygromycin
MXPA00010822A (es)	2001-07-31	Derivados de 2"-desoxi higromicina
CZ20004075A3 (cs)	2001-05-16	Deriváty 2"-deoxy-hygromycinu
AU2001260528A1 (en)	2001-12-11	Hygromycin a derivatives for the treatment of bacterial and protozoal infections
MXPA00010821A (en)	2001-07-31	Hygromycin a derivatives
CZ20004074A3 (cs)	2001-05-16	Deriváty hygromycinu A
NZ523779A (en)	2003-09-26	Hygromycin A derivatives
HK1036628A (en)	2002-01-11	2"-deoxy hygromycin derivatives