OA11721A - Hygromycin A derivatives as antibacterial agents. - Google Patents

Hygromycin A derivatives as antibacterial agents. Download PDF

Info

Publication number: OA11721A
Authority: OA; OAPI
Prior art keywords: methyl; hydroxy; trihydroxy; tetrahydro; furan
Prior art date: 1998-12-02

Application number

OA1200100135A

Other languages

English (en)

Inventor

Matthew Merrill Hayward

Original Assignee

Pfizer Prod 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.)

1998-12-02

Filing date

1999-11-09

Publication date

2005-01-25

1999-11-09 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2005-01-25 Publication of OA11721A publication Critical patent/OA11721A/en

Links

239000003242 anti bacterial agent Substances 0.000 title abstract description 6
YQYJSBFKSSDGFO-FWAVGLHBSA-N hygromycin A Chemical class 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 title description 44
150000001875 compounds Chemical class 0.000 claims abstract description 94
238000000034 method Methods 0.000 claims abstract description 42
208000015181 infectious disease Diseases 0.000 claims abstract description 40
150000003839 salts Chemical class 0.000 claims abstract description 28
208000035143 Bacterial infection Diseases 0.000 claims abstract description 15
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
-1 azido, hydroxy Chemical group 0.000 claims description 68
125000003118 aryl group Chemical group 0.000 claims description 60
125000000623 heterocyclic group Chemical group 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 32
229920002554 vinyl polymer Polymers 0.000 claims description 18
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 17
238000011282 treatment Methods 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000004434 sulfur atom Chemical group 0.000 claims description 12
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
241000251468 Actinopterygii Species 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
208000028172 protozoa infectious disease Diseases 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 4
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 4
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
RRIWSQXXBIFKQM-UHFFFAOYSA-N monomeric N-benzylcarbamic acid Natural products OC(=O)NCC1=CC=CC=C1 RRIWSQXXBIFKQM-UHFFFAOYSA-N 0.000 claims description 3
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
WPWXYQIMXTUMJB-UHFFFAOYSA-N tert-butyl 3-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(CN)C1 WPWXYQIMXTUMJB-UHFFFAOYSA-N 0.000 claims description 3
NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 claims description 2
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000651 prodrug Substances 0.000 claims 1
229940002612 prodrug Drugs 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
208000035475 disorder Diseases 0.000 abstract description 9
206010037075 Protozoal infections Diseases 0.000 abstract description 8
230000001580 bacterial effect Effects 0.000 abstract description 6
230000000844 anti-bacterial effect Effects 0.000 abstract description 5
239000003904 antiprotozoal agent Substances 0.000 abstract description 2
239000012453 solvate Substances 0.000 abstract 1
229940117913 acrylamide Drugs 0.000 description 175
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 130
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 70
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 67
239000000243 solution Substances 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
235000019439 ethyl acetate Nutrition 0.000 description 44
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
229940093499 ethyl acetate Drugs 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 29
235000002639 sodium chloride Nutrition 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 24
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000000872 buffer Substances 0.000 description 16
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
230000000694 effects Effects 0.000 description 15
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 14
239000002253 acid Substances 0.000 description 14
229940073584 methylene chloride Drugs 0.000 description 14
238000010898 silica gel chromatography Methods 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
239000012043 crude product Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000002609 medium Substances 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
238000000855 fermentation Methods 0.000 description 8
230000004151 fermentation Effects 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241000283690 Bos taurus Species 0.000 description 7
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 7
125000004494 ethyl ester group Chemical group 0.000 description 7
239000002054 inoculum Substances 0.000 description 7
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
241000193996 Streptococcus pyogenes Species 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000011591 potassium Substances 0.000 description 6
239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
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 5
238000010792 warming Methods 0.000 description 5
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000588724 Escherichia coli Species 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
241000191967 Staphylococcus aureus Species 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000007853 buffer solution Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
QQFBQBDINHJDMN-UHFFFAOYSA-N ethyl 2-trimethylsilylacetate Chemical compound CCOC(=O)C[Si](C)(C)C QQFBQBDINHJDMN-UHFFFAOYSA-N 0.000 description 4
150000002243 furanoses Chemical class 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
101100337363 Dictyostelium discoideum gmsA gene Proteins 0.000 description 3
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238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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238000003527 Peterson olefination reaction Methods 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
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108010059993 Vancomycin Proteins 0.000 description 3
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230000001154 acute effect Effects 0.000 description 3
238000013019 agitation Methods 0.000 description 3
239000003513 alkali Substances 0.000 description 3
150000004808 allyl alcohols Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
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229910000019 calcium carbonate Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
238000011068 loading method Methods 0.000 description 3
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
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BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 3
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
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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
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JDYCDPFQWXHUDL-UHFFFAOYSA-N trimethyl(methylsulfanyl)silane Chemical compound CS[Si](C)(C)C JDYCDPFQWXHUDL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—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
- A61P31/02—Local antiseptics
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Oncology (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

OA1200100135A 1998-12-02 1999-11-09 Hygromycin A derivatives as antibacterial agents. OA11721A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US11061898P	1998-12-02	1998-12-02

Publications (1)

Publication Number	Publication Date
OA11721A true OA11721A (en)	2005-01-25

Family

ID=22334003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200100135A OA11721A (en)	1998-12-02	1999-11-09	Hygromycin A derivatives as antibacterial agents.

Country Status (38)

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US (1)	US6245745B1 (is)
EP (1)	EP1135400A1 (is)
JP (1)	JP3393189B2 (is)
KR (1)	KR100418167B1 (is)
CN (1)	CN1329617A (is)
AP (1)	AP2001002154A0 (is)
AR (1)	AR019784A1 (is)
AU (1)	AU6362799A (is)
BG (1)	BG105645A (is)
BR (1)	BR9915813A (is)
CA (1)	CA2352332C (is)
CO (1)	CO5150171A1 (is)
CZ (1)	CZ20011904A3 (is)
DZ (1)	DZ2932A1 (is)
EA (1)	EA004303B1 (is)
EE (1)	EE200100301A (is)
GE (1)	GEP20033144B (is)
GT (1)	GT199900205A (is)
HN (1)	HN1999000202A (is)
HR (1)	HRP20010413A2 (is)
HU (1)	HUP0104949A3 (is)
ID (1)	ID28848A (is)
IL (1)	IL142882A0 (is)
IS (1)	IS5930A (is)
MA (1)	MA26705A1 (is)
NO (1)	NO20012687D0 (is)
NZ (1)	NZ511424A (is)
OA (1)	OA11721A (is)
PA (1)	PA8486101A1 (is)
PE (1)	PE20001429A1 (is)
PL (1)	PL348063A1 (is)
SK (1)	SK7302001A3 (is)
TN (1)	TNSN99211A1 (is)
TR (1)	TR200101540T2 (is)
UY (1)	UY25827A1 (is)
WO (1)	WO2000032616A1 (is)
YU (1)	YU32601A (is)
ZA (1)	ZA200104434B (is)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CZ20021355A3 (cs) *	1999-10-29	2002-11-13	Pfizer Products Inc.	Deriváty hygromycinu
CZ20021347A3 (cs) *	1999-10-29	2002-11-13	Pfizer Products Inc.	Proléčiva hygromycinu A
CN1432019A (zh) *	2000-06-02	2003-07-23	辉瑞产品公司	用于治疗细菌和原生动物感染的潮霉素a衍生物
US20050031181A1 (en) *	2003-06-19	2005-02-10	Xiaoli Bi	Method and system for analyzing bone conditions using DICOM compliant bone radiographic image

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1075483B1 (en) *	1998-05-04	2003-12-03	Pfizer Products Inc.	Hygromycin a derivatives
ATE243218T1 (de) *	1998-05-04	2003-07-15	Pfizer Prod Inc	2''-deoxyhygromycinderivate

1999
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- 1999-11-09 CN CN99813939A patent/CN1329617A/zh active Pending
- 1999-11-09 EP EP99951055A patent/EP1135400A1/en not_active Withdrawn
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- 1999-11-09 WO PCT/IB1999/001798 patent/WO2000032616A1/en not_active Ceased
- 1999-11-09 CA CA002352332A patent/CA2352332C/en not_active Expired - Fee Related
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- 1999-11-09 KR KR10-2001-7006849A patent/KR100418167B1/ko not_active Expired - Fee Related
- 1999-11-09 AU AU63627/99A patent/AU6362799A/en not_active Abandoned
- 1999-11-09 AP APAP/P/2001/002154A patent/AP2001002154A0/en unknown
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- 1999-11-09 JP JP2000585257A patent/JP3393189B2/ja not_active Expired - Fee Related
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- 1999-11-10 TN TNTNSN99211A patent/TNSN99211A1/fr unknown
- 1999-11-10 DZ DZ990232A patent/DZ2932A1/xx active
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- 1999-11-15 AR ARP990105799A patent/AR019784A1/es not_active Application Discontinuation
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- 1999-12-02 US US09/453,429 patent/US6245745B1/en not_active Expired - Fee Related
2001
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- 2001-05-31 NO NO20012687A patent/NO20012687D0/no not_active Application Discontinuation
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Also Published As

Publication number	Publication date
IS5930A (is)	2001-04-27
HN1999000202A (es)	2000-06-13
YU32601A (sh)	2004-05-12
HUP0104949A2 (hu)	2002-04-29
NO20012687L (no)	2001-05-31
ID28848A (id)	2001-07-05
EE200100301A (et)	2002-08-15
NO20012687D0 (no)	2001-05-31
AU6362799A (en)	2000-06-19
HRP20010413A2 (en)	2002-06-30
MA26705A1 (fr)	2004-12-20
CA2352332C (en)	2004-12-07
GT199900205A (es)	2001-05-24
PA8486101A1 (es)	2000-09-29
CZ20011904A3 (cs)	2001-10-17
EA004303B1 (ru)	2004-02-26
KR100418167B1 (ko)	2004-02-11
PL348063A1 (en)	2002-05-06
KR20010093136A (ko)	2001-10-27
JP2002531463A (ja)	2002-09-24
EA200100444A1 (ru)	2001-10-22
JP3393189B2 (ja)	2003-04-07
CA2352332A1 (en)	2000-06-08
UY25827A1 (es)	2001-08-27
ZA200104434B (en)	2002-05-30
HUP0104949A3 (en)	2003-12-29
BR9915813A (pt)	2001-08-21
TR200101540T2 (tr)	2001-10-22
AP2001002154A0 (en)	2001-05-09
BG105645A (bg)	2002-02-28
EP1135400A1 (en)	2001-09-26
DZ2932A1 (fr)	2004-03-15
US6245745B1 (en)	2001-06-12
AR019784A1 (es)	2002-03-13
WO2000032616A1 (en)	2000-06-08
IL142882A0 (en)	2002-03-10
GEP20033144B (en)	2003-12-25
NZ511424A (en)	2003-08-29
CN1329617A (zh)	2002-01-02
TNSN99211A1 (fr)	2005-11-10
SK7302001A3 (en)	2001-12-03
CO5150171A1 (es)	2002-04-29
PE20001429A1 (es)	2000-12-18

Publication	Publication Date	Title
EP1075483B1 (en)	2003-12-03	Hygromycin a derivatives
OA11721A (en)	2005-01-25	Hygromycin A derivatives as antibacterial agents.
EP1077984B1 (en)	2003-06-18	2"-deoxy hygromycin derivatives
US6867230B2 (en)	2005-03-15	Hygromycin A derivatives
CA2389191A1 (en)	2001-05-03	Hygromycin derivatives
AU2004201309A1 (en)	2004-04-29	Hygromycin A Derivatives as Antibacterial Agents
EP1369490B1 (en)	2006-02-08	Method of preparing a composition containing hygromycin A and epi-hygromycin
MXPA01005554A (en)	2001-12-04	Hygromycin a derivatives as antibacterial agents
MXPA00010822A (es)	2001-07-31	Derivados de 2"-desoxi higromicina