JPH0373523B2 - - Google Patents
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- Publication number
- JPH0373523B2 JPH0373523B2 JP8060683A JP8060683A JPH0373523B2 JP H0373523 B2 JPH0373523 B2 JP H0373523B2 JP 8060683 A JP8060683 A JP 8060683A JP 8060683 A JP8060683 A JP 8060683A JP H0373523 B2 JPH0373523 B2 JP H0373523B2
- Authority
- JP
- Japan
- Prior art keywords
- drugs
- strains
- effects
- combination
- acid
- Prior art date
- 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.)
- Expired
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- 239000000203 mixture Substances 0.000 claims description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 4
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- 230000002195 synergetic effect Effects 0.000 description 7
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 6
- 230000003042 antagnostic effect Effects 0.000 description 6
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 6
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 229960000723 ampicillin Drugs 0.000 description 4
- GCFBRXLSHGKWDP-XCGNWRKASA-N cefoperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC(O)=CC=1)C(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 GCFBRXLSHGKWDP-XCGNWRKASA-N 0.000 description 4
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960000210 nalidixic acid Drugs 0.000 description 4
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 4
- 229960001180 norfloxacin Drugs 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 229960004682 cefoperazone Drugs 0.000 description 3
- 229960004261 cefotaxime Drugs 0.000 description 3
- AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 description 3
- 229940106164 cephalexin Drugs 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 229940056360 penicillin g Drugs 0.000 description 3
- 229960001732 pipemidic acid Drugs 0.000 description 3
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 description 3
- IVBHGBMCVLDMKU-GXNBUGAJSA-N piperacillin Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 IVBHGBMCVLDMKU-GXNBUGAJSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YSLIPUSJNFIFAB-UHFFFAOYSA-N 2-oxopyridine-1-carboxylic acid Chemical compound OC(=O)N1C=CC=CC1=O YSLIPUSJNFIFAB-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229940126575 aminoglycoside Drugs 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229960002292 piperacillin Drugs 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WZRJTRPJURQBRM-UHFFFAOYSA-N 4-amino-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1.COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 WZRJTRPJURQBRM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000589291 Acinetobacter Species 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- 101100542977 Arabidopsis thaliana PIPC gene Proteins 0.000 description 1
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 206010042276 Subacute endocarditis Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003781 beta lactamase inhibitor Substances 0.000 description 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- SYLKGLMBLAAGSC-QLVMHMETSA-N cefsulodin Chemical compound C1=CC(C(=O)N)=CC=[N+]1CC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)[C@@H](C=3C=CC=CC=3)S(O)(=O)=O)[C@H]2SC1 SYLKGLMBLAAGSC-QLVMHMETSA-N 0.000 description 1
- 229960003202 cefsulodin Drugs 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229960003324 clavulanic acid Drugs 0.000 description 1
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229960000318 kanamycin Drugs 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 229930182823 kanamycin A Natural products 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229960001699 ofloxacin Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur 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
- 239000003826 tablet Substances 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
〔産業上の利用分野〕
本発明は式
で示される化合物またはその付加塩あるいは水和
物とβ−ラクタム系抗生物質との組合せからなる
組成物を有効成分とする抗菌性組成物に関する。
〔従来の技術〕
一般に薬剤の併用効果に関しては古くより知ら
れており、抗菌剤に関しても併用による相乗効
果、耐性菌出現の防止、抗菌スペクトルの拡大、
副作用の軽減、薬物の不活化酵素の抑制等を目的
として研究が続けられている。
しかし薬物を併用した場合、相乗あるいは相加
作用を示す場合と逆に拮抗的な作用を示す場合が
知られている。例えばペニシリンＧはアミノ配糖
体系薬物と相乗作用を示すがクロラムフエニコー
ルやテトラサイクリン系薬物とは拮抗作用を示
す。またアミノ配糖体系薬物とマクロライド系薬
物では相加的な作用しか示さない。
このように化学療法剤の併用に関する問題はそ
のメカニズムも含めて不明な点が多い。従つて臨
床上実用に供せられている併用薬はペニシリンＧ
とストレプトマイシン（またはカナマイシン）、
また近年注目されたトリメトプリムとスルフアメ
トキサゾールあるいはアンピシリンとクラブラン
酸（またはその類似薬）ぐらいのものである。し
かしこれらとて次のような問題点に直面してい
る。すなわち、ペニシリンＧとストレプトマイシ
ンは現在では両剤の耐性菌の増加によりもはや両
者の併用は亜急性心内膜炎以外には意味のないも
のになつている。またサルフア剤とトリメトプリ
ム合剤も造血臓器への障害などにより適量の使用
はさけられている。さらにアンピシリンとβ−ラ
クタマーゼ抑制剤との併用においても基礎的には
抑制にばらつきがあり、臨床面でも効果が安定し
ていない。
〔発明が解決しようとする問題点〕
今日、種々の抗生剤が次々と開発されているに
もかかわらず、第１選択剤としての条件、すなわ
ち、強い殺菌性を有し、耐性菌の出現頻度が少な
く抗菌スペクトルが広く、更に安全性が高い等の
条件を具備した薬剤はいまだみあたらない。
〔問題点を解決するための手段〕
本発明者等は一連の抗菌剤開発研究途上に於
て、ナリジクス酸をはじめとするピリドンカルボ
ン酸系薬物とβ−ラクタム系抗生物質との合剤に
より前記の条件が満足されるものと考え、基礎的
研究を重ねて来た。その結果両剤との間に顕著な
相乗効果のあることを認めた。しかし反面ある種
の病原菌に対しては拮抗作用を示す事も判明し
た。従つて合剤としての実用性は欠くものと判断
された。しかし本発明者等は更に鋭意研究を重ね
た結果、ピリドンカルボン酸系薬物の中でも式
［］で示される化合物、即ちノルフロキサシン
は驚いた事に他のピリドンカルボン酸系薬物例え
ばナリジクス酸やピペミド酸のようにある種の病
原菌に対して拮抗作用を示すような作用が無い事
を発見し、ここにおいて初めて、本発明者等によ
つて実用的な配合剤が完成された。
本発明組成物の成分としてのβ−ラクタム系抗
生物質としては例えばアンピシリン、セフアレキ
シン、ピペラシリン、セフオタキシム、セフオペ
ラゾン、セフスロジン等があげられる。
投与形態としては例えば錠剤、カプセル剤、懸
濁剤、液剤、シロップ剤等の経口投与形態、軟膏
剤、液剤、スプレー剤等の外用形態および注射用
形態等があげられる。
〔実施例および発明の効果〕
以下実験例を示して本発明を更に詳細に説明す
る。
実施例 １
インビトロにおける相乗効果の測定
日本化学療法学会標準法を応用して寒天平板希
釈チエス盤法により２種の薬剤の組合せの系列を
作製して検討した。併用する薬剤の倍数希釈系列
を各々作製してその各濃度段階を互に組合せてこ
れをミユーラー・ヒントンメデイウムに含ませて
寒天平板を作製した。試験菌株をミユーラー・ヒ
ントンブロスで37℃１夜培養し、その100倍希釈
液をミクロプランターを用いて先に作製した寒天
平板に接種した。菌液接種後37℃で20時間培養
し、寒天上のコロニーの発育の有無を観察して感
受性を判定しFICインデツクス（F.Paulaら：
Antimicrob.Agents ＆ chemother.，11巻、
225頁、1977年）を求めた。試験結果は表１〜４
にまとめた。
尚表中には次の略号を使用した。
ABPC：アンピシリン
PIPC：ピペラシリン
CEX：セフアレキシン
CTX：セフオタキシム
CPZ：セフオペラゾン
CFS：セフスロジン
NFLX：ノルフロキサシン、１−エチル−
６−フルオロ−１，４−ジヒドロ
−４−オキソ−７−（１−ピペラ
ジニル）キノリン−３−カルボン
酸
NA：ナリジクス酸
PPA：ピペミド酸
DL：オフロキサシン
表１では臨床分離のS.marcescens9株に対する
併用効果が示されている。
ナリジクス酸はセフアレキシン、セフオタキシ
ム、セフオペラゾン、セフスロジンとの併用に於
てそれぞれ６株中２株、12株中６株、13株中７
株、９株中４株とかなりの 効率で拮抗作用が認
められた。これに対しノルフロキサシンでは全く
拮抗作用は認められず、相加又は相乗作用は全株
で認められた。
表２では臨床分離のP.aeruginosa、表３では
Acinetobacter属、表４ではAlcaligene属に対す
る併用効果が示されている。いずれの菌種でもノ
ルフロキサシンは全株に相加又は相乗効果が認め
られた。ナリジクス酸、ピペミド酸では拮抗作用
を示す菌株が散見された。
[Industrial Application Field] The present invention is based on the formula The present invention relates to an antibacterial composition containing as an active ingredient a composition consisting of a combination of the compound shown in (1) or an addition salt or hydrate thereof and a β-lactam antibiotic. [Prior art] In general, the effects of combinations of drugs have been known for a long time, and with regard to antibacterial agents, there is a synergistic effect, prevention of the appearance of resistant bacteria, expansion of the antibacterial spectrum,
Research continues with the aim of reducing side effects and inhibiting enzymes that inactivate drugs. However, when drugs are used together, it is known that in some cases they show synergistic or additive effects, and in others they show antagonistic effects. For example, penicillin G exhibits a synergistic effect with aminoglycoside drugs, but an antagonistic effect with chloramphenicol and tetracycline drugs. Furthermore, aminoglycoside drugs and macrolide drugs only exhibit additive effects. As described above, there are many questions regarding the combination of chemotherapeutic agents, including their mechanisms, that are unclear. Therefore, the concomitant drug used clinically is penicillin G.
and streptomycin (or kanamycin),
Other examples include trimethoprim and sulfamethoxazole, or ampicillin and clavulanic acid (or similar drugs), which have attracted attention in recent years. However, these methods face the following problems. That is, due to the increase in bacteria resistant to both penicillin G and streptomycin, the combination of the two drugs is no longer meaningful except for subacute endocarditis. Furthermore, the use of a combination of sulfur drugs and trimethoprim in appropriate amounts is avoided due to damage to hematopoietic organs. Furthermore, when ampicillin is used in combination with a β-lactamase inhibitor, the inhibition basically varies, and the effect is not stable clinically. [Problems to be solved by the invention] Today, although various antibiotics are being developed one after another, the conditions for being a first-choice drug are not met, namely, having strong bactericidal properties and the frequency of appearance of resistant bacteria. No drug has yet been found that meets the following requirements: low oxidation, broad antibacterial spectrum, and high safety. [Means for Solving the Problems] In the course of a series of research on the development of antibacterial agents, the present inventors discovered the We have conducted repeated basic research believing that the following conditions are satisfied. As a result, it was found that there was a significant synergistic effect between the two drugs. However, on the other hand, it has also been found to have antagonistic effects against certain pathogenic bacteria. Therefore, it was judged that it lacked practicality as a mixture. However, as a result of further intensive research, the present inventors found that among pyridonecarboxylic acid drugs, the compound represented by the formula [], that is, norfloxacin, surprisingly showed that other pyridonecarboxylic acid drugs such as nalidixic acid and pipemidic acid It was discovered that there was no antagonistic effect against certain pathogenic bacteria, and this was the first time that the present inventors completed a practical combination drug. Examples of the β-lactam antibiotic as a component of the composition of the present invention include ampicillin, cephalexin, piperacillin, cefotaxime, cefoperazone, and cefsulozin. Examples of dosage forms include oral dosage forms such as tablets, capsules, suspensions, solutions, and syrups; external dosage forms such as ointments, solutions, and sprays; and injection forms. [Examples and Effects of the Invention] The present invention will be explained in more detail below with reference to experimental examples. Example 1 Measurement of synergistic effect in vitro A series of combinations of two drugs was prepared and investigated using the agar plate dilution cheese plate method, applying the Japanese Society of Chemotherapy standard method. A series of multiple dilutions of the drugs to be used in combination was prepared, and the respective concentration levels were combined and included in Mueller-Hinton medium to prepare agar plates. The test strain was cultured in Mueller-Hinton broth at 37°C overnight, and a 100-fold dilution thereof was inoculated onto the previously prepared agar plate using a microplanter. After inoculating the bacterial solution, culture at 37°C for 20 hours, observe the presence or absence of colony growth on agar to determine susceptibility, and use the FIC index (F. Paula et al.:
Antimicrob.Agents & chemother., vol. 11,
p. 225, 1977). Test results are in Tables 1-4
summarized in. The following abbreviations were used in the table. ABPC: Ampicillin PIPC: Piperacillin CEX: Cephalexin CTX: Cefotaxime CPZ: Cefoperazone CFS: Cefsulozin NFLX: Norfloxacin, 1-ethyl-
6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid NA: nalidixic acid PPA: pipemidic acid DL: ofloxacin Table 1 shows the combinations against nine clinically isolated S. marcescens strains. It has been shown to be effective. Nalidixic acid was used in combination with cephalexin, cefotaxime, cefoperazone, and cefsulodin in 2 of 6 strains, 6 of 12 strains, and 7 of 13 strains, respectively.
Antagonism was observed with considerable efficiency in 4 out of 9 strains. In contrast, no antagonistic effect was observed with norfloxacin, and additive or synergistic effects were observed in all strains. Table 2 shows the clinical isolate P. aeruginosa, Table 3 shows the clinical isolate P. aeruginosa.
Table 4 shows the combined effect against the genus Acinetobacter and the genus Alcaligene. Norfloxacin had an additive or synergistic effect on all bacterial strains. Bacterial strains showing antagonistic effects on nalidixic acid and pipemidic acid were found here and there.
【表】【table】
【表】【table】
【表】【table】
Claims (1)
物とβ−ラクタム系抗生物質とを有効成分とする
ことを特徴とする抗菌性組成物。 ２ 有効量の式 で示される化合物またはその付加塩あるいは水和
物と有効量のβ−ラクタム系抗生物質および製剤
上必要な賦形剤から成る特許請求の範囲第１項記
載の抗菌性組成物。[Claims] 1 formula An antibacterial composition comprising as active ingredients a compound represented by the above formula or an addition salt or hydrate thereof and a β-lactam antibiotic. 2 Effective amount formula 2. The antibacterial composition according to claim 1, which comprises a compound represented by the above formula or an addition salt or hydrate thereof, an effective amount of a β-lactam antibiotic, and excipients necessary for formulation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8060683A JPS606617A (en) | 1983-05-09 | 1983-05-09 | Antibacterial agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8060683A JPS606617A (en) | 1983-05-09 | 1983-05-09 | Antibacterial agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS606617A JPS606617A (en) | 1985-01-14 |
| JPH0373523B2 true JPH0373523B2 (en) | 1991-11-22 |
Family
ID=13722986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8060683A Granted JPS606617A (en) | 1983-05-09 | 1983-05-09 | Antibacterial agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS606617A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4767762A (en) * | 1985-12-23 | 1988-08-30 | Abbott Laboratories | Tricyclic quinoline and naphthyride antibacterials |
| JP2800939B2 (en) * | 1987-08-31 | 1998-09-21 | 大日本製薬株式会社 | Tricyclic compounds, esters and salts thereof |
| US5273973A (en) * | 1988-10-24 | 1993-12-28 | Norwich Eaton Pharmaceuticals, Inc. | Antimicrobial quinolonyl esters |
| US5491139A (en) * | 1988-10-24 | 1996-02-13 | The Procter & Gamble Company | Antimicrobial quinolonyl lactams |
| US5328908A (en) * | 1988-10-24 | 1994-07-12 | Procter & Gamble Pharmaceuticals, Inc. | Antimicrobial quinolone thioureas |
| US5180719A (en) * | 1988-10-24 | 1993-01-19 | Norwich Eaton Pharmaceuticals, Inc. | Antimicrobial quinolonyl lactam esters |
| EP0997466A1 (en) * | 1988-10-24 | 2000-05-03 | PROCTER & GAMBLE PHARMACEUTICALS, INC. | Novel antimicrobial lactam-quinolones |
| CA2001203C (en) * | 1988-10-24 | 2001-02-13 | Thomas P. Demuth, Jr. | Novel antimicrobial dithiocarbamoyl quinolones |
| EP0525057B1 (en) | 1990-04-18 | 2000-06-14 | Procter & Gamble Pharmaceuticals, Inc. | Antimicrobial quinolonyl lactams |
| KR100295742B1 (en) * | 1999-04-16 | 2001-07-03 | 이동규 | Complex antibiotic composition for animal bacterial infections |
-
1983
- 1983-05-09 JP JP8060683A patent/JPS606617A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS606617A (en) | 1985-01-14 |
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