PH26316A - Antimicrobial agent for animals - Google Patents
Antimicrobial agent for animals Download PDFInfo
- Publication number
- PH26316A PH26316A PH39070A PH39070A PH26316A PH 26316 A PH26316 A PH 26316A PH 39070 A PH39070 A PH 39070A PH 39070 A PH39070 A PH 39070A PH 26316 A PH26316 A PH 26316A
- Authority
- PH
- Philippines
- Prior art keywords
- species
- mycoplasma
- compound
- staphylococcus
- coli
- Prior art date
Links
- 241001465754 Metazoa Species 0.000 title claims description 27
- 239000004599 antimicrobial Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 71
- 241000588724 Escherichia coli Species 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 241000204031 Mycoplasma Species 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 241000283690 Bos taurus Species 0.000 claims description 6
- 241000607142 Salmonella Species 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 241000271566 Aves Species 0.000 claims description 4
- 241000282472 Canis lupus familiaris Species 0.000 claims description 4
- 241000282326 Felis catus Species 0.000 claims description 4
- 241000191967 Staphylococcus aureus Species 0.000 claims description 4
- 241000282887 Suidae Species 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 241000191940 Staphylococcus Species 0.000 claims description 3
- 241000588779 Bordetella bronchiseptica Species 0.000 claims description 2
- 241000606790 Haemophilus Species 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 241000606856 Pasteurella multocida Species 0.000 claims 4
- 229940051027 pasteurella multocida Drugs 0.000 claims 4
- 241000191963 Staphylococcus epidermidis Species 0.000 claims 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 241000606748 Actinobacillus pleuropneumoniae Species 0.000 claims 1
- 241000186042 Actinomyces bovis Species 0.000 claims 1
- 241000606767 Avibacterium paragallinarum Species 0.000 claims 1
- 241000588747 Klebsiella pneumoniae Species 0.000 claims 1
- 241000202938 Mycoplasma hyorhinis Species 0.000 claims 1
- 241000588770 Proteus mirabilis Species 0.000 claims 1
- 241000607683 Salmonella enterica subsp. enterica serovar Pullorum Species 0.000 claims 1
- 241000191982 Staphylococcus hyicus Species 0.000 claims 1
- 241000194017 Streptococcus Species 0.000 claims 1
- 241000193985 Streptococcus agalactiae Species 0.000 claims 1
- 241000186064 Trueperella pyogenes Species 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 241000287828 Gallus gallus Species 0.000 description 24
- 235000013330 chicken meat Nutrition 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 230000000845 anti-microbial effect Effects 0.000 description 13
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 11
- 241000204022 Mycoplasma gallisepticum Species 0.000 description 11
- 208000015181 infectious disease Diseases 0.000 description 11
- 208000035473 Communicable disease Diseases 0.000 description 9
- 235000010633 broth Nutrition 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- -1 alkali metal salts Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical class C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 description 4
- CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical compound O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010028470 Mycoplasma infections Diseases 0.000 description 4
- 210000004712 air sac Anatomy 0.000 description 4
- 244000052616 bacterial pathogen Species 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 3
- 206010039438 Salmonella Infections Diseases 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000005130 benzoxazines Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229960001699 ofloxacin Drugs 0.000 description 3
- 229960000321 oxolinic acid Drugs 0.000 description 3
- 206010039447 salmonellosis Diseases 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000032969 Hemorrhagic Septicemia Diseases 0.000 description 2
- 208000014645 Pasteurella hemorrhagic septicemia Diseases 0.000 description 2
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 201000003146 cystitis Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- IMLJLCJZQLGHJS-JEKSYDDFSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;dihydrate Chemical compound O.O.C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O IMLJLCJZQLGHJS-JEKSYDDFSA-N 0.000 description 1
- QLEIDMAURCRVCX-UHFFFAOYSA-N 1-propylpiperazine Chemical compound CCCN1CCNCC1 QLEIDMAURCRVCX-UHFFFAOYSA-N 0.000 description 1
- AQNOPFHAWMMARU-UHFFFAOYSA-N 2H-1,4-benzoxazine-6-carboxylic acid hydrochloride Chemical compound Cl.O1CC=NC2=C1C=CC(=C2)C(=O)O AQNOPFHAWMMARU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 201000008283 Atrophic Rhinitis Diseases 0.000 description 1
- 241000588807 Bordetella Species 0.000 description 1
- 101100367084 Caenorhabditis elegans such-1 gene Proteins 0.000 description 1
- 206010008631 Cholera Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010014568 Empyema Diseases 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 206010061126 Escherichia infection Diseases 0.000 description 1
- 206010061190 Haemophilus infection Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 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 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000004100 Oxytetracycline Substances 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 206010034107 Pasteurella infections Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010039088 Rhinitis atrophic Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004182 Tylosin Substances 0.000 description 1
- 229930194936 Tylosin Natural products 0.000 description 1
- ZULJYVVAYGFYKU-UHFFFAOYSA-N acetonitrile;chloroform Chemical compound CC#N.ClC(Cl)Cl ZULJYVVAYGFYKU-UHFFFAOYSA-N 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002725 anti-mycoplasma Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 208000020612 escherichia coli infection Diseases 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229960000625 oxytetracycline Drugs 0.000 description 1
- 235000019366 oxytetracycline Nutrition 0.000 description 1
- 201000005115 pasteurellosis Diseases 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229960004444 piromidic acid Drugs 0.000 description 1
- RCIMBBZXSXFZBV-UHFFFAOYSA-N piromidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCCC1 RCIMBBZXSXFZBV-UHFFFAOYSA-N 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 201000006509 pleuropneumonia Diseases 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000001974 tryptic soy broth Substances 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
- 229960004059 tylosin Drugs 0.000 description 1
- 235000019375 tylosin Nutrition 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19819988 | 1988-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26316A true PH26316A (en) | 1992-04-29 |
Family
ID=16387124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH39070A PH26316A (en) | 1988-08-09 | 1989-08-08 | Antimicrobial agent for animals |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0354453B1 (ko) |
| KR (1) | KR0137767B1 (ko) |
| CN (1) | CN1042732C (ko) |
| AU (1) | AU625066B2 (ko) |
| CA (1) | CA1339449C (ko) |
| DE (1) | DE68920794T2 (ko) |
| ES (1) | ES2070150T3 (ko) |
| MY (1) | MY104139A (ko) |
| NZ (1) | NZ230130A (ko) |
| PH (1) | PH26316A (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW208013B (ko) * | 1990-03-01 | 1993-06-21 | Daiichi Co Ltd | |
| CN1055927C (zh) * | 1997-11-18 | 2000-08-30 | 中国科学院上海药物研究所 | 左旋氧氟沙星类似物的合成及其用途 |
| SE9904108D0 (sv) * | 1999-11-15 | 1999-11-15 | New Pharma Research Ab | Nya föreningar |
| CN102101865A (zh) * | 2009-12-22 | 2011-06-22 | 江苏九寿堂生物制品有限公司 | 一种喹诺酮类化合物盐酸盐的结晶形式 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5746986A (en) * | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| JPS60184014A (ja) * | 1984-03-02 | 1985-09-19 | Dai Ichi Seiyaku Co Ltd | 動物のマイコプラズマ感染症の予防・治療剤 |
| AU585995B2 (en) * | 1985-06-20 | 1989-06-29 | Daiichi Pharmaceutical Co., Ltd. | Optically active pyridobenzoxazine derivatives and intermediates thereof |
| DK170473B1 (da) * | 1985-06-20 | 1995-09-11 | Daiichi Seiyaku Co | S(-)-pyridobenzoxazinforbindelser |
| DE3639465A1 (de) * | 1986-11-18 | 1988-05-19 | Hoechst Ag | Optisch aktive gyrasehemmer, ihre herstellung und verwendung als antibiotika |
-
1989
- 1989-07-25 MY MYPI89001014A patent/MY104139A/en unknown
- 1989-07-28 NZ NZ230130A patent/NZ230130A/en unknown
- 1989-08-01 EP EP89114219A patent/EP0354453B1/en not_active Expired - Lifetime
- 1989-08-01 DE DE68920794T patent/DE68920794T2/de not_active Expired - Fee Related
- 1989-08-01 ES ES89114219T patent/ES2070150T3/es not_active Expired - Lifetime
- 1989-08-01 CA CA000607148A patent/CA1339449C/en not_active Expired - Fee Related
- 1989-08-03 AU AU39276/89A patent/AU625066B2/en not_active Ceased
- 1989-08-03 KR KR1019890011102A patent/KR0137767B1/ko not_active IP Right Cessation
- 1989-08-08 PH PH39070A patent/PH26316A/en unknown
- 1989-08-09 CN CN89105541A patent/CN1042732C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1042732C (zh) | 1999-03-31 |
| CA1339449C (en) | 1997-09-09 |
| KR0137767B1 (ko) | 1998-05-15 |
| NZ230130A (en) | 1992-06-25 |
| EP0354453A2 (en) | 1990-02-14 |
| CN1040200A (zh) | 1990-03-07 |
| MY104139A (en) | 1994-02-28 |
| KR900002781A (ko) | 1990-03-23 |
| ES2070150T3 (es) | 1995-06-01 |
| EP0354453B1 (en) | 1995-01-25 |
| AU625066B2 (en) | 1992-07-02 |
| EP0354453A3 (en) | 1991-04-10 |
| AU3927689A (en) | 1990-02-15 |
| DE68920794D1 (de) | 1995-03-09 |
| DE68920794T2 (de) | 1995-06-29 |
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