AU2001260528A1 - Hygromycin a derivatives for the treatment of bacterial and protozoal infections - Google Patents

Hygromycin a derivatives for the treatment of bacterial and protozoal infections

Info

Publication number: AU2001260528A1
Authority: AU; Australia
Prior art keywords: methyl; hydroxy; phenyl; chloro; aryl
Prior art date: 2000-06-02
Legal status (The legal status 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 status listed.): Abandoned

Application number

AU2001260528A

Other languages

English (en)

Inventor

Matthew Merrill Hayward

Takushi Kaneko

Robert Gerald Linde Ii

Michael Scott Visser

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

Original Assignee

Pfizer Products Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-06-02

Filing date

2001-05-25

Publication date

2001-12-11

2001-05-25 Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc

2001-12-11 Publication of AU2001260528A1 publication Critical patent/AU2001260528A1/en

Status Abandoned legal-status Critical Current

Links

208000035143 Bacterial infection Diseases 0.000 title claims description 18
208000022362 bacterial infectious disease Diseases 0.000 title claims description 18
238000011282 treatment Methods 0.000 title claims description 17
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 70
206010037075 Protozoal infections Diseases 0.000 title description 9
230000001580 bacterial effect Effects 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 83
238000000034 method Methods 0.000 claims description 46
-1 azido, hydroxy Chemical group 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
239000000651 prodrug Substances 0.000 claims description 17
229940002612 prodrug Drugs 0.000 claims description 17
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 16
125000000623 heterocyclic group Chemical group 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 11
241000251468 Actinopterygii Species 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 10
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
229910052799 carbon 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
208000028172 protozoa infectious disease Diseases 0.000 claims description 7
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000001072 heteroaryl group Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
239000012453 solvate Substances 0.000 claims description 4
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
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 53
239000000243 solution Substances 0.000 description 52
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
235000019439 ethyl acetate Nutrition 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 37
208000015181 infectious disease Diseases 0.000 description 37
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
238000002360 preparation method Methods 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000872 buffer Substances 0.000 description 17
230000000694 effects Effects 0.000 description 16
239000000047 product Substances 0.000 description 15
239000002253 acid Substances 0.000 description 14
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 14
239000007787 solid Substances 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
239000000203 mixture Substances 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
238000010898 silica gel chromatography Methods 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
238000000855 fermentation Methods 0.000 description 12
230000004151 fermentation Effects 0.000 description 12
150000002576 ketones Chemical class 0.000 description 12
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 12
235000019341 magnesium sulphate Nutrition 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
239000002904 solvent Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
150000001299 aldehydes Chemical class 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 10
239000002054 inoculum Substances 0.000 description 10
239000002609 medium Substances 0.000 description 10
241000283690 Bos taurus Species 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 9
239000012043 crude product Substances 0.000 description 9
208000035475 disorder Diseases 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
238000003527 Peterson olefination reaction Methods 0.000 description 8
239000002585 base Substances 0.000 description 8
125000004494 ethyl ester group Chemical group 0.000 description 8
239000011347 resin Substances 0.000 description 8
229920005989 resin Polymers 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
239000012267 brine Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
125000004122 cyclic group Chemical group 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
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 7
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
125000004429 atom Chemical group 0.000 description 6
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 6
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
238000006751 Mitsunobu reaction Methods 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
241000187391 Streptomyces hygroscopicus Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
238000003556 assay Methods 0.000 description 5
238000010511 deprotection reaction Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
150000002243 furanoses Chemical class 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
230000008569 process Effects 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000012321 sodium triacetoxyborohydride Substances 0.000 description 5
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 5
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
241000191967 Staphylococcus aureus Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
238000007239 Wittig reaction Methods 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
230000000844 anti-bacterial effect Effects 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000005822 corn Nutrition 0.000 description 4
239000013530 defoamer Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000003814 drug Substances 0.000 description 4
JSEMUSFPVZYRSG-UHFFFAOYSA-N ethyl 3-(triphenyl-$l^{5}-phosphanylidene)propanoate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CCC(=O)OCC)C1=CC=CC=C1 JSEMUSFPVZYRSG-UHFFFAOYSA-N 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
230000001404 mediated effect Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 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
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000000746 purification Methods 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000003549 soybean oil Substances 0.000 description 4
235000012424 soybean oil Nutrition 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
238000010792 warming Methods 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
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238000010189 synthetic method Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000001583 thiepanyl group Chemical group 0.000 description 1
125000002053 thietanyl group Chemical group 0.000 description 1
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
210000001519 tissue Anatomy 0.000 description 1
238000003354 tissue distribution assay Methods 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
206010044008 tonsillitis Diseases 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61P31/04—Antibacterial agents
- 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
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Genetics & Genomics (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biotechnology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

AU2001260528A 2000-06-02 2001-05-25 Hygromycin a derivatives for the treatment of bacterial and protozoal infections Abandoned AU2001260528A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US20902300P	2000-06-02	2000-06-02
US60209023		2000-06-02
PCT/IB2001/000946 WO2001092280A1 (en)	2000-06-02	2001-05-25	Hygromycin a derivatives for the treatment of bacterial and protozoal infections

Publications (1)

Publication Number	Publication Date
AU2001260528A1 true AU2001260528A1 (en)	2001-12-11

Family

ID=22777009

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2001260528A Abandoned AU2001260528A1 (en)	2000-06-02	2001-05-25	Hygromycin a derivatives for the treatment of bacterial and protozoal infections

Country Status (31)

Country	Link
US (1)	US6867230B2 (es)
EP (1)	EP1287011A1 (es)
JP (1)	JP2003535100A (es)
KR (1)	KR20030010655A (es)
CN (1)	CN1432019A (es)
AP (1)	AP2002002669A0 (es)
AR (1)	AR028667A1 (es)
AU (1)	AU2001260528A1 (es)
BG (1)	BG107265A (es)
BR (1)	BR0111242A (es)
CA (1)	CA2410643A1 (es)
CZ (1)	CZ20023859A3 (es)
EA (1)	EA200201167A1 (es)
EC (1)	ECSP014093A (es)
EE (1)	EE200200671A (es)
GT (1)	GT200100099A (es)
HU (1)	HUP0302263A2 (es)
IL (1)	IL152984A0 (es)
IS (1)	IS6618A (es)
MA (1)	MA26909A1 (es)
MX (1)	MXPA02011966A (es)
NO (1)	NO20025704D0 (es)
OA (1)	OA12277A (es)
PA (1)	PA8518101A1 (es)
PE (1)	PE20020334A1 (es)
PL (1)	PL359179A1 (es)
SK (1)	SK16612002A3 (es)
SV (1)	SV2002000474A (es)
TN (1)	TNSN01080A1 (es)
UY (1)	UY26741A1 (es)
WO (1)	WO2001092280A1 (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE516263T1 (de)	2002-05-16	2011-07-15	Sunovion Pharmaceuticals Inc	Amine, die einen säugetier-anandamidtransporter hemmen; und verfahren zu deren verwendung
EP3840743A4 (en) *	2018-08-20	2022-08-17	Northeastern University	HYGROMYCIN A COMPOUNDS AND METHODS OF TREATING SPIROCHETE DISEASES
CU20180159A7 (es) *	2018-12-28	2020-10-20	Chengdu Olisynn Biotechnology Co Ltd	Derivados de oligosacáridos sintéticos como vacuna contra la bordetella pertussis

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1234567A (en) *	1915-09-14	1917-07-24	Edward J Quigley	Soft collar.
US2004123A (en) *	1934-02-15	1935-06-11	Jr Robert B Loibl	Pest exterminator
CN1299367A (zh) *	1998-05-04	2001-06-13	辉瑞产品公司	2"－脱氧潮霉素衍生物
PL344521A1 (en) *	1998-05-04	2001-11-05	Pfizer Prod Inc	Hygromycin a derivatives
KR100418167B1 (ko) *	1998-12-02	2004-02-11	화이자 프로덕츠 인크.	항균제로서의 하이그로마이신 ａ 유도체
KR20020063885A (ko) *	1999-10-29	2002-08-05	화이자 프로덕츠 인코포레이티드	하이그로마이신 유도체
US7654321B2 (en) *	2006-12-27	2010-02-02	Schlumberger Technology Corporation	Formation fluid sampling apparatus and methods

2001
- 2001-05-25 KR KR1020027016396A patent/KR20030010655A/ko not_active Application Discontinuation
- 2001-05-25 BR BR0111242-2A patent/BR0111242A/pt not_active IP Right Cessation
- 2001-05-25 EE EEP200200671A patent/EE200200671A/xx unknown
- 2001-05-25 PL PL01359179A patent/PL359179A1/xx not_active Application Discontinuation
- 2001-05-25 WO PCT/IB2001/000946 patent/WO2001092280A1/en not_active Application Discontinuation
- 2001-05-25 IL IL15298401A patent/IL152984A0/xx unknown
- 2001-05-25 AP APAP/P/2002/002669A patent/AP2002002669A0/en unknown
- 2001-05-25 CA CA002410643A patent/CA2410643A1/en not_active Abandoned
- 2001-05-25 HU HU0302263A patent/HUP0302263A2/hu unknown
- 2001-05-25 EA EA200201167A patent/EA200201167A1/ru unknown
- 2001-05-25 OA OA1200200361A patent/OA12277A/en unknown
- 2001-05-25 EP EP01934231A patent/EP1287011A1/en not_active Withdrawn
- 2001-05-25 JP JP2002500893A patent/JP2003535100A/ja not_active Withdrawn
- 2001-05-25 MX MXPA02011966A patent/MXPA02011966A/es not_active Application Discontinuation
- 2001-05-25 CZ CZ20023859A patent/CZ20023859A3/cs unknown
- 2001-05-25 SK SK1661-2002A patent/SK16612002A3/sk unknown
- 2001-05-25 AU AU2001260528A patent/AU2001260528A1/en not_active Abandoned
- 2001-05-25 CN CN01810623A patent/CN1432019A/zh active Pending
- 2001-05-30 GT GT200100099A patent/GT200100099A/es unknown
- 2001-05-30 PA PA20018518101A patent/PA8518101A1/es unknown
- 2001-05-31 UY UY26741A patent/UY26741A1/es not_active Application Discontinuation
- 2001-06-01 AR ARP010102642A patent/AR028667A1/es unknown
- 2001-06-01 TN TNTNSN01080A patent/TNSN01080A1/fr unknown
- 2001-06-01 US US09/872,731 patent/US6867230B2/en not_active Expired - Fee Related
- 2001-06-01 EC EC2001004093A patent/ECSP014093A/es unknown
- 2001-06-01 SV SV2001000474A patent/SV2002000474A/es not_active Application Discontinuation
- 2001-06-01 PE PE2001000511A patent/PE20020334A1/es not_active Application Discontinuation
2002
- 2002-11-12 BG BG107265A patent/BG107265A/bg unknown
- 2002-11-14 IS IS6618A patent/IS6618A/is unknown
- 2002-11-27 NO NO20025704A patent/NO20025704D0/no not_active Application Discontinuation
- 2002-11-29 MA MA26928A patent/MA26909A1/fr unknown

Also Published As

Publication number	Publication date
GT200100099A (es)	2002-01-31
PL359179A1 (en)	2004-08-23
KR20030010655A (ko)	2003-02-05
NO20025704L (no)	2002-11-27
BR0111242A (pt)	2003-06-03
PE20020334A1 (es)	2002-04-30
OA12277A (en)	2006-05-11
JP2003535100A (ja)	2003-11-25
SK16612002A3 (sk)	2004-04-06
CA2410643A1 (en)	2001-12-06
NO20025704D0 (no)	2002-11-27
PA8518101A1 (es)	2002-09-17
WO2001092280A1 (en)	2001-12-06
IS6618A (is)	2002-11-14
ECSP014093A (es)	2002-01-25
MXPA02011966A (es)	2003-04-22
BG107265A (bg)	2003-07-31
HUP0302263A2 (hu)	2003-10-28
TNSN01080A1 (fr)	2005-11-10
CZ20023859A3 (cs)	2004-02-18
AP2002002669A0 (en)	2002-12-31
EA200201167A1 (ru)	2003-06-26
IL152984A0 (en)	2003-06-24
US6867230B2 (en)	2005-03-15
EE200200671A (et)	2004-08-16
CN1432019A (zh)	2003-07-23
UY26741A1 (es)	2001-12-28
AR028667A1 (es)	2003-05-21
US20030045528A1 (en)	2003-03-06
SV2002000474A (es)	2002-07-03
EP1287011A1 (en)	2003-03-05
MA26909A1 (fr)	2004-12-20

Publication	Publication Date	Title
EP1075483B1 (en)	2003-12-03	Hygromycin a derivatives
EP1077984B1 (en)	2003-06-18	2"-deoxy hygromycin derivatives
US6245745B1 (en)	2001-06-12	Hygromycin A derivatives
US6867230B2 (en)	2005-03-15	Hygromycin A derivatives
WO2001030795A1 (en)	2001-05-03	Hygromycin derivatives
EP1369490B1 (en)	2006-02-08	Method of preparing a composition containing hygromycin A and epi-hygromycin
MXPA01005554A (es)	2001-12-04	Derivados de higromicina
AU2004201309A1 (en)	2004-04-29	Hygromycin A Derivatives as Antibacterial Agents
MXPA00010822A (es)	2001-07-31	Derivados de 2"-desoxi higromicina
MXPA00010821A (es)	2001-07-31	Derivados de higromicina a