HRP20010413A2 - Hygromycin a derivatives as antibacterial agents - Google Patents

Hygromycin a derivatives as antibacterial agents Download PDF

Info

Publication number: HRP20010413A2
Authority: HR; Croatia
Prior art keywords: methyl; hydroxy; yloxy; benzo; trihydroxy
Prior art date: 1998-12-02

Application number

HR20010413A

Other languages

English (en)

Croatian (hr)

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

2001-05-29

Publication date

2002-06-30

2001-05-29 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2002-06-30 Publication of HRP20010413A2 publication Critical patent/HRP20010413A2/hr

Links

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 79
239000003242 anti bacterial agent Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims description 101
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 53
-1 azido, hydroxy Chemical group 0.000 claims description 51
238000000034 method Methods 0.000 claims description 44
125000000623 heterocyclic group Chemical group 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 35
125000003118 aryl group Chemical group 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 20
125000005843 halogen group Chemical group 0.000 claims description 18
229920002554 vinyl polymer Polymers 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
208000010362 Protozoan Infections Diseases 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 15
208000035143 Bacterial infection Diseases 0.000 claims description 14
208000022362 bacterial infectious disease Diseases 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
125000000217 alkyl group Chemical group 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
125000004430 oxygen atom Chemical group 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
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 11
208000035475 disorder Diseases 0.000 claims description 11
241000251468 Actinopterygii Species 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 10
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
238000011282 treatment Methods 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
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 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 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl 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
229920006395 saturated elastomer Polymers 0.000 claims description 4
NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
XRKIHUXCUIFHAS-UHFFFAOYSA-N [4-(3-methoxy-3-oxopropyl)phenyl]boronic acid Chemical compound COC(=O)CCC1=CC=C(B(O)O)C=C1 XRKIHUXCUIFHAS-UHFFFAOYSA-N 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
238000010511 deprotection reaction Methods 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
125000005842 heteroatom Chemical group 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
239000000825 pharmaceutical preparation Substances 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
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 1
239000000651 prodrug Substances 0.000 claims 1
229940002612 prodrug Drugs 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 142
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
239000000243 solution Substances 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
235000019439 ethyl acetate Nutrition 0.000 description 48
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 46
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
208000015181 infectious disease Diseases 0.000 description 33
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 28
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
238000004587 chromatography analysis Methods 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000000872 buffer Substances 0.000 description 16
230000000694 effects Effects 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000003513 alkali Substances 0.000 description 13
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 12
239000012043 crude product Substances 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000007787 solid Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
238000000855 fermentation Methods 0.000 description 11
230000004151 fermentation Effects 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
150000001412 amines Chemical class 0.000 description 9
241000894006 Bacteria Species 0.000 description 8
241000283690 Bos taurus Species 0.000 description 8
230000001580 bacterial effect Effects 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
206010061218 Inflammation Diseases 0.000 description 7
241001465754 Metazoa Species 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
230000004054 inflammatory process Effects 0.000 description 7
239000002609 medium Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229910019142 PO4 Inorganic materials 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
241000193996 Streptococcus pyogenes Species 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
235000021317 phosphate Nutrition 0.000 description 6
239000000126 substance Substances 0.000 description 6
229920002472 Starch Polymers 0.000 description 5
241000187391 Streptomyces hygroscopicus Species 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000007853 buffer solution Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
125000004494 ethyl ester group Chemical group 0.000 description 5
238000010438 heat treatment Methods 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
238000000746 purification Methods 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000008107 starch Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000271566 Aves Species 0.000 description 4
229910021580 Cobalt(II) chloride Inorganic materials 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
238000003527 Peterson olefination reaction Methods 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
241000282887 Suidae 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
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
235000005822 corn Nutrition 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000010828 elution Methods 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
239000012499 inoculation medium 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
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
239000010452 phosphate Substances 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
235000012424 soybean oil Nutrition 0.000 description 4
239000003549 soybean oil Substances 0.000 description 4
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 4
241000282472 Canis lupus familiaris Species 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
241000282326 Felis catus Species 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
241000699670 Mus sp. Species 0.000 description 3
241000606856 Pasteurella multocida Species 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052784 alkaline earth metal Chemical class 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
235000011130 ammonium sulphate Nutrition 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
235000010216 calcium carbonate Nutrition 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
239000007884 disintegrant Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
159000000011 group IA salts Chemical class 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000011068 loading method Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
238000002156 mixing 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
239000002674 ointment Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
235000000346 sugar Nutrition 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241001148536 Bacteroides sp. Species 0.000 description 2
241001148534 Brachyspira Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
241000606153 Chlamydia trachomatis Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241000193403 Clostridium 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
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000606768 Haemophilus influenzae Species 0.000 description 2
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 2
239000007836 KH2PO4 Substances 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
238000006751 Mitsunobu reaction Methods 0.000 description 2
241001502334 Mycobacterium avium complex bacterium Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
241000191992 Peptostreptococcus Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920000954 Polyglycolide Polymers 0.000 description 2
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239000008183 oral pharmaceutical preparation Substances 0.000 description 1
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NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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159000000001 potassium salts Chemical class 0.000 description 1
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150000007660 quinolones Chemical class 0.000 description 1
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229910000033 sodium borohydride Inorganic materials 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
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150000003890 succinate salts Chemical class 0.000 description 1
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125000003831 tetrazolyl group Chemical group 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
125000001544 thienyl group Chemical group 0.000 description 1
125000001583 thiepanyl group Chemical group 0.000 description 1
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SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
JDYCDPFQWXHUDL-UHFFFAOYSA-N trimethyl(methylsulfanyl)silane Chemical compound CS[Si](C)(C)C JDYCDPFQWXHUDL-UHFFFAOYSA-N 0.000 description 1
BFUMGFNGDCUBSH-UHFFFAOYSA-N trimethylsilylmethanesulfonyl chloride Chemical compound C[Si](C)(C)CS(Cl)(=O)=O BFUMGFNGDCUBSH-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
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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)

HR20010413A 1998-12-02 2001-05-29 Hygromycin a derivatives as antibacterial agents HRP20010413A2 (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
HRP20010413A2 true HRP20010413A2 (en)	2002-06-30

Family

ID=22334003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20010413A HRP20010413A2 (en)	1998-12-02	2001-05-29	Hygromycin a derivatives as antibacterial agents

Country Status (38)

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

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR0015153A (pt) *	1999-10-29	2002-07-16	Pfizer Prod Inc	Derivados de higromicina
BR0015156A (pt) *	1999-10-29	2002-07-16	Pfizer Prod Inc	Pró-drogas de higromicina a
IL152984A0 (en) *	2000-06-02	2003-06-24	Pfizer Prod Inc	Hygromycin a derivatives for the treatment of bacterial and protozoal infections
EP1643901A4 (en) *	2003-06-19	2008-10-29	Compumed Inc	METHOD AND SYSTEM FOR ANALYZING BONE CONDITIONS USING A RADIOGRAPHIC IMAGE OF COMPATIBLE DICOM OS

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MA24852A1 (fr) *	1998-05-04	1999-12-31	Pfizer Prod Inc	Derives d'hygromycine a et leur procede de preparation
AU762302B2 (en) *	1998-05-04	2003-06-19	Pfizer Products Inc.	2"-deoxy hygromycin derivatives

1999
- 1999-11-09 YU YU32601A patent/YU32601A/sh unknown
- 1999-11-09 SK SK730-2001A patent/SK7302001A3/sk unknown
- 1999-11-09 ID IDW00200101182A patent/ID28848A/id unknown
- 1999-11-09 GE GEAP19995922A patent/GEP20033144B/en unknown
- 1999-11-09 EE EEP200100301A patent/EE200100301A/xx unknown
- 1999-11-09 CZ CZ20011904A patent/CZ20011904A3/cs unknown
- 1999-11-09 OA OA1200100135A patent/OA11721A/en unknown
- 1999-11-09 KR KR10-2001-7006849A patent/KR100418167B1/ko not_active IP Right Cessation
- 1999-11-09 BR BR9915813-2A patent/BR9915813A/pt not_active IP Right Cessation
- 1999-11-09 IL IL14288299A patent/IL142882A0/xx unknown
- 1999-11-09 AU AU63627/99A patent/AU6362799A/en not_active Abandoned
- 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 HU HU0104949A patent/HUP0104949A3/hu unknown
- 1999-11-09 EA EA200100444A patent/EA004303B1/ru not_active IP Right Cessation
- 1999-11-09 EP EP99951055A patent/EP1135400A1/en not_active Withdrawn
- 1999-11-09 AP APAP/P/2001/002154A patent/AP2001002154A0/en unknown
- 1999-11-09 CA CA002352332A patent/CA2352332C/en not_active Expired - Fee Related
- 1999-11-09 TR TR2001/01540T patent/TR200101540T2/xx unknown
- 1999-11-09 WO PCT/IB1999/001798 patent/WO2000032616A1/en not_active Application Discontinuation
- 1999-11-09 CN CN99813939A patent/CN1329617A/zh active Pending
- 1999-11-09 PL PL99348063A patent/PL348063A1/xx not_active Application Discontinuation
- 1999-11-10 MA MA25843A patent/MA26705A1/fr unknown
- 1999-11-10 TN TNTNSN99211A patent/TNSN99211A1/fr unknown
- 1999-11-10 DZ DZ990232A patent/DZ2932A1/xx active
- 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
- 2001-05-29 HR HR20010413A patent/HRP20010413A2/hr not_active Application Discontinuation
- 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
OA11721A (en)	2005-01-25
HN1999000202A (es)	2000-06-13
SK7302001A3 (en)	2001-12-03
JP2002531463A (ja)	2002-09-24
IL142882A0 (en)	2002-03-10
CN1329617A (zh)	2002-01-02
EA200100444A1 (ru)	2001-10-22
NO20012687D0 (no)	2001-05-31
ID28848A (id)	2001-07-05
KR20010093136A (ko)	2001-10-27
ZA200104434B (en)	2002-05-30
TR200101540T2 (tr)	2001-10-22
CO5150171A1 (es)	2002-04-29
MA26705A1 (fr)	2004-12-20
CA2352332C (en)	2004-12-07
BR9915813A (pt)	2001-08-21
DZ2932A1 (fr)	2004-03-15
GEP20033144B (en)	2003-12-25
TNSN99211A1 (fr)	2005-11-10
AU6362799A (en)	2000-06-19
HUP0104949A3 (en)	2003-12-29
GT199900205A (es)	2001-05-24
HUP0104949A2 (hu)	2002-04-29
JP3393189B2 (ja)	2003-04-07
YU32601A (sh)	2004-05-12
EE200100301A (et)	2002-08-15
AP2001002154A0 (en)	2001-05-09
EP1135400A1 (en)	2001-09-26
PA8486101A1 (es)	2000-09-29
IS5930A (is)	2001-04-27
AR019784A1 (es)	2002-03-13
NO20012687L (no)	2001-05-31
KR100418167B1 (ko)	2004-02-11
CA2352332A1 (en)	2000-06-08
NZ511424A (en)	2003-08-29
PL348063A1 (en)	2002-05-06
PE20001429A1 (es)	2000-12-18
WO2000032616A1 (en)	2000-06-08
BG105645A (bg)	2002-02-28
US6245745B1 (en)	2001-06-12
UY25827A1 (es)	2001-08-27
EA004303B1 (ru)	2004-02-26
CZ20011904A3 (cs)	2001-10-17

Legal Events

Date	Code	Title
2002-06-30	A1OB	Publication of a patent application
2002-07-03	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2008-12-08	OBST	Application withdrawn

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