SK7302001A3 - Hygromycin a derivatives as antibacterial agents - Google Patents

Hygromycin a derivatives as antibacterial agents Download PDF

Info

Publication number: SK7302001A3
Authority: SK; Slovakia
Prior art keywords: methyl; yloxy; dioxol; acrylamide; propenyl
Prior art date: 1998-12-02

Application number

SK730-2001A

Other languages

English (en)

Slovak (sk)

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

2001-12-03

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

2001-12-03 Publication of SK7302001A3 publication Critical patent/SK7302001A3/sk

Links

239000003242 anti bacterial agent Substances 0.000 title abstract description 9
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 title description 57
150000001875 compounds Chemical class 0.000 claims abstract description 98
208000015181 infectious disease Diseases 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 33
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
208000035143 Bacterial infection Diseases 0.000 claims abstract description 14
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 14
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
239000012453 solvate Substances 0.000 claims abstract description 5
-1 azido, hydroxy Chemical group 0.000 claims description 516
125000003118 aryl group Chemical group 0.000 claims description 67
125000000623 heterocyclic group Chemical group 0.000 claims description 38
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 26
229910052717 sulfur Inorganic materials 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 19
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 19
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 17
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
229920002554 vinyl polymer Polymers 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 12
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
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
241000251468 Actinopterygii Species 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
125000006017 1-propenyl group Chemical group 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
125000004434 sulfur atom Chemical group 0.000 claims description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
208000028172 protozoa infectious disease Diseases 0.000 claims description 4
ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 3
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 3
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 3
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 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
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
238000010511 deprotection reaction Methods 0.000 claims description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
229950005514 glycyclamide Drugs 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
239000003446 ligand Substances 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
230000001580 bacterial effect Effects 0.000 abstract description 6
206010037075 Protozoal infections Diseases 0.000 abstract description 3
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
208000035475 disorder Diseases 0.000 abstract description 3
239000003904 antiprotozoal agent Substances 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 139
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
239000000243 solution Substances 0.000 description 53
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
235000019439 ethyl acetate Nutrition 0.000 description 47
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 description 35
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 23
238000000855 fermentation Methods 0.000 description 21
230000004151 fermentation Effects 0.000 description 21
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
239000000872 buffer Substances 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 16
239000002253 acid Substances 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 15
235000019341 magnesium sulphate Nutrition 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000004587 chromatography analysis Methods 0.000 description 14
230000000694 effects Effects 0.000 description 14
201000010099 disease Diseases 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 12
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
239000012043 crude product Substances 0.000 description 11
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 11
238000002360 preparation method Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 9
239000002609 medium Substances 0.000 description 9
241000283690 Bos taurus Species 0.000 description 8
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
241000894006 Bacteria 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
239000003153 chemical reaction reagent Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
125000004494 ethyl ester group Chemical group 0.000 description 5
239000002054 inoculum Substances 0.000 description 5
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical class [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 5
239000000047 product Substances 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000271566 Aves Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
241000193996 Streptococcus pyogenes Species 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
235000002017 Zea mays subsp mays Nutrition 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001447 alkali salts Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000002518 antifoaming agent Substances 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
239000012267 brine Substances 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
235000005822 corn Nutrition 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
238000001704 evaporation Methods 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
239000012499 inoculation medium Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000011343 solid material Substances 0.000 description 4
239000003549 soybean oil Substances 0.000 description 4
235000012424 soybean oil Nutrition 0.000 description 4
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 4
HQIXMKWBUPCCGR-LHECETPHSA-N (e)-n-[(3as,4r,5r,6s,7r,7ar)-4,6,7-trihydroxy-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl]-3-(3-hydroxyphenyl)-2-methylprop-2-enamide Chemical compound N([C@@H]1[C@@H]([C@@H](O)[C@H]2OCO[C@H]2[C@@H]1O)O)C(=O)C(/C)=C/C1=CC=CC(O)=C1 HQIXMKWBUPCCGR-LHECETPHSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
101100337363 Dictyostelium discoideum gmsA gene Proteins 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 3
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
241000187391 Streptomyces hygroscopicus Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
150000007514 bases Chemical class 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 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
244000052769 pathogen Species 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
229910021653 sulphate ion Inorganic materials 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000010792 warming Methods 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
241000194033 Enterococcus Species 0.000 description 2
241000194032 Enterococcus faecalis Species 0.000 description 2
241000194031 Enterococcus faecium Species 0.000 description 2
244000024675 Eruca sativa Species 0.000 description 2
235000014755 Eruca sativa Nutrition 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
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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

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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)
Tropical Medicine & Parasitology (AREA)
Oncology (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)

SK730-2001A 1998-12-02 1999-11-09 Hygromycin a derivatives as antibacterial agents SK7302001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US11061898P	1998-12-02	1998-12-02
PCT/IB1999/001798 WO2000032616A1 (en)	1998-12-02	1999-11-09	Hygromycin a derivatives as antibacterial agents

Publications (1)

Publication Number	Publication Date
SK7302001A3 true SK7302001A3 (en)	2001-12-03

Family

ID=22334003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK730-2001A SK7302001A3 (en)	1998-12-02	1999-11-09	Hygromycin a derivatives as antibacterial agents

Country Status (38)

Country	Link
US (1)	US6245745B1 (cs)
EP (1)	EP1135400A1 (cs)
JP (1)	JP3393189B2 (cs)
KR (1)	KR100418167B1 (cs)
CN (1)	CN1329617A (cs)
AP (1)	AP2001002154A0 (cs)
AR (1)	AR019784A1 (cs)
AU (1)	AU6362799A (cs)
BG (1)	BG105645A (cs)
BR (1)	BR9915813A (cs)
CA (1)	CA2352332C (cs)
CO (1)	CO5150171A1 (cs)
CZ (1)	CZ20011904A3 (cs)
DZ (1)	DZ2932A1 (cs)
EA (1)	EA004303B1 (cs)
EE (1)	EE200100301A (cs)
GE (1)	GEP20033144B (cs)
GT (1)	GT199900205A (cs)
HN (1)	HN1999000202A (cs)
HR (1)	HRP20010413A2 (cs)
HU (1)	HUP0104949A3 (cs)
ID (1)	ID28848A (cs)
IL (1)	IL142882A0 (cs)
IS (1)	IS5930A (cs)
MA (1)	MA26705A1 (cs)
NO (1)	NO20012687L (cs)
NZ (1)	NZ511424A (cs)
OA (1)	OA11721A (cs)
PA (1)	PA8486101A1 (cs)
PE (1)	PE20001429A1 (cs)
PL (1)	PL348063A1 (cs)
SK (1)	SK7302001A3 (cs)
TN (1)	TNSN99211A1 (cs)
TR (1)	TR200101540T2 (cs)
UY (1)	UY25827A1 (cs)
WO (1)	WO2000032616A1 (cs)
YU (1)	YU32601A (cs)
ZA (1)	ZA200104434B (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1382150A (zh) *	1999-10-29	2002-11-27	辉瑞产品公司	潮霉素衍生物
BR0015156A (pt) *	1999-10-29	2002-07-16	Pfizer Prod Inc	Pró-drogas de higromicina a
CA2410643A1 (en)	2000-06-02	2001-12-06	Pfizer Products Inc.	Hygromycin a derivatives for the treatment of bacterial and protozoal infections
WO2004112580A2 (en) *	2003-06-19	2004-12-29	Compumed, Inc.	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
KR100396099B1 (ko) *	1998-05-04	2003-08-27	화이자 프로덕츠 인코포레이티드	2''-데옥시 하이그로마이신 유도체
YU66900A (sh) *	1998-05-04	2003-12-31	Pfizer Products Inc.	Derivati higromicina a

1999
- 1999-11-09 JP JP2000585257A patent/JP3393189B2/ja not_active Expired - Fee Related
- 1999-11-09 NZ NZ511424A patent/NZ511424A/en unknown
- 1999-11-09 BR BR9915813-2A patent/BR9915813A/pt not_active IP Right Cessation
- 1999-11-09 SK SK730-2001A patent/SK7302001A3/sk unknown
- 1999-11-09 HU HU0104949A patent/HUP0104949A3/hu unknown
- 1999-11-09 WO PCT/IB1999/001798 patent/WO2000032616A1/en not_active Ceased
- 1999-11-09 EE EEP200100301A patent/EE200100301A/xx unknown
- 1999-11-09 OA OA1200100135A patent/OA11721A/en unknown
- 1999-11-09 ID IDW00200101182A patent/ID28848A/id unknown
- 1999-11-09 GE GEAP19995922A patent/GEP20033144B/en unknown
- 1999-11-09 TR TR2001/01540T patent/TR200101540T2/xx unknown
- 1999-11-09 KR KR10-2001-7006849A patent/KR100418167B1/ko not_active Expired - Fee Related
- 1999-11-09 YU YU32601A patent/YU32601A/sh unknown
- 1999-11-09 AU AU63627/99A patent/AU6362799A/en not_active Abandoned
- 1999-11-09 CA CA002352332A patent/CA2352332C/en not_active Expired - Fee Related
- 1999-11-09 EP EP99951055A patent/EP1135400A1/en not_active Withdrawn
- 1999-11-09 IL IL14288299A patent/IL142882A0/xx unknown
- 1999-11-09 AP APAP/P/2001/002154A patent/AP2001002154A0/en unknown
- 1999-11-09 HR HR20010413A patent/HRP20010413A2/hr not_active Application Discontinuation
- 1999-11-09 CN CN99813939A patent/CN1329617A/zh active Pending
- 1999-11-09 CZ CZ20011904A patent/CZ20011904A3/cs unknown
- 1999-11-09 PL PL99348063A patent/PL348063A1/xx not_active Application Discontinuation
- 1999-11-09 EA EA200100444A patent/EA004303B1/ru not_active IP Right Cessation
- 1999-11-10 DZ DZ990232A patent/DZ2932A1/xx active
- 1999-11-10 TN TNTNSN99211A patent/TNSN99211A1/fr unknown
- 1999-11-10 MA MA25843A patent/MA26705A1/fr unknown
- 1999-11-15 AR ARP990105799A patent/AR019784A1/es not_active Application Discontinuation
- 1999-11-18 HN HN1999000202A patent/HN1999000202A/es unknown
- 1999-11-25 CO CO99074411A patent/CO5150171A1/es unknown
- 1999-11-29 PE PE1999001195A patent/PE20001429A1/es not_active Application Discontinuation
- 1999-11-30 PA PA19998486101A patent/PA8486101A1/es unknown
- 1999-11-30 UY UY25827A patent/UY25827A1/es unknown
- 1999-12-01 GT GT199900205A patent/GT199900205A/es unknown
- 1999-12-02 US US09/453,429 patent/US6245745B1/en not_active Expired - Fee Related
2001
- 2001-04-27 IS IS5930A patent/IS5930A/is unknown
- 2001-05-30 ZA ZA200104434A patent/ZA200104434B/en unknown
- 2001-05-31 NO NO20012687A patent/NO20012687L/no not_active Application Discontinuation
- 2001-06-25 BG BG105645A patent/BG105645A/bg unknown

Also Published As

Publication number	Publication date
KR100418167B1 (ko)	2004-02-11
CA2352332A1 (en)	2000-06-08
KR20010093136A (ko)	2001-10-27
PL348063A1 (en)	2002-05-06
PE20001429A1 (es)	2000-12-18
UY25827A1 (es)	2001-08-27
TNSN99211A1 (fr)	2005-11-10
DZ2932A1 (fr)	2004-03-15
US6245745B1 (en)	2001-06-12
IS5930A (is)	2001-04-27
OA11721A (en)	2005-01-25
ZA200104434B (en)	2002-05-30
CN1329617A (zh)	2002-01-02
HUP0104949A2 (hu)	2002-04-29
BR9915813A (pt)	2001-08-21
EA200100444A1 (ru)	2001-10-22
GT199900205A (es)	2001-05-24
IL142882A0 (en)	2002-03-10
CA2352332C (en)	2004-12-07
NZ511424A (en)	2003-08-29
AU6362799A (en)	2000-06-19
JP2002531463A (ja)	2002-09-24
HRP20010413A2 (en)	2002-06-30
NO20012687D0 (no)	2001-05-31
HUP0104949A3 (en)	2003-12-29
MA26705A1 (fr)	2004-12-20
AP2001002154A0 (en)	2001-05-09
EA004303B1 (ru)	2004-02-26
AR019784A1 (es)	2002-03-13
TR200101540T2 (tr)	2001-10-22
NO20012687L (no)	2001-05-31
JP3393189B2 (ja)	2003-04-07
CZ20011904A3 (cs)	2001-10-17
BG105645A (bg)	2002-02-28
WO2000032616A1 (en)	2000-06-08
EP1135400A1 (en)	2001-09-26
CO5150171A1 (es)	2002-04-29
PA8486101A1 (es)	2000-09-29
HN1999000202A (es)	2000-06-13
EE200100301A (et)	2002-08-15
GEP20033144B (en)	2003-12-25
ID28848A (id)	2001-07-05
YU32601A (sh)	2004-05-12

Publication	Publication Date	Title
US20070060545A1 (en)	2007-03-15	Novel compounds
EP1075483B1 (en)	2003-12-03	Hygromycin a derivatives
US6245745B1 (en)	2001-06-12	Hygromycin A derivatives
DE69908936T2 (de)	2004-05-19	2''-deoxyhygromycinderivate
CZ20021355A3 (cs)	2002-11-13	Deriváty hygromycinu
US6867230B2 (en)	2005-03-15	Hygromycin A derivatives
AU2004201309A1 (en)	2004-04-29	Hygromycin A Derivatives as Antibacterial Agents
MXPA01005554A (en)	2001-12-04	Hygromycin a derivatives as antibacterial agents
CZ20004074A3 (cs)	2001-05-16	Deriváty hygromycinu A
MXPA00010822A (es)	2001-07-31	Derivados de 2"-desoxi higromicina
EP1369490A1 (en)	2003-12-10	Method of preparing a composition containing hygromycin A and epi-hygromycin