PH26316A - Antimicrobial agent for animals - Google Patents

Antimicrobial agent for animals Download PDF

Info

Publication number: PH26316A
Authority: PH; Philippines
Prior art keywords: species; mycoplasma; compound; staphylococcus; coli
Prior art date: 1988-08-09

Application number

PH39070A

Other languages

English (en)

Inventor

Toshihiro Takahata

Masakazu Takei

Masahiro Kato

Tadayoshi Miura

Toshiyuki Yoshioka

Original Assignee

Daiichi Seiyaku Co

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.)

1988-08-09

Filing date

1989-08-08

Publication date

1992-04-29

1989-08-08 Application filed by Daiichi Seiyaku Co filed Critical Daiichi Seiyaku Co

1992-04-29 Publication of PH26316A publication Critical patent/PH26316A/en

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)

PH39070A 1988-08-09 1989-08-08 Antimicrobial agent for animals PH26316A (en)

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 (es)
KR (1)	KR0137767B1 (es)
CN (1)	CN1042732C (es)
AU (1)	AU625066B2 (es)
CA (1)	CA1339449C (es)
DE (1)	DE68920794T2 (es)
ES (1)	ES2070150T3 (es)
MY (1)	MY104139A (es)
NZ (1)	NZ230130A (es)
PH (1)	PH26316A (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW208013B (es) *	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
KR102866350B1 (ko)	2023-02-24	2025-10-14	아세아시멘트(주)	염소바이패스 분진 자원화 처리 방법

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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
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 CA CA000607148A patent/CA1339449C/en not_active Expired - Fee Related
- 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
- 1989-08-03 AU AU39276/89A patent/AU625066B2/en not_active Ceased
- 1989-08-03 KR KR1019890011102A patent/KR0137767B1/ko not_active Expired - Fee Related
- 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
EP0354453A3 (en)	1991-04-10
KR0137767B1 (ko)	1998-05-15
CA1339449C (en)	1997-09-09
EP0354453B1 (en)	1995-01-25
NZ230130A (en)	1992-06-25
KR900002781A (ko)	1990-03-23
CN1040200A (zh)	1990-03-07
DE68920794T2 (de)	1995-06-29
AU3927689A (en)	1990-02-15
DE68920794D1 (de)	1995-03-09
AU625066B2 (en)	1992-07-02
ES2070150T3 (es)	1995-06-01
CN1042732C (zh)	1999-03-31
MY104139A (en)	1994-02-28
EP0354453A2 (en)	1990-02-14

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