JPH0481967B2 - - Google Patents
Info
- Publication number
- JPH0481967B2 JPH0481967B2 JP25276184A JP25276184A JPH0481967B2 JP H0481967 B2 JPH0481967 B2 JP H0481967B2 JP 25276184 A JP25276184 A JP 25276184A JP 25276184 A JP25276184 A JP 25276184A JP H0481967 B2 JPH0481967 B2 JP H0481967B2
- Authority
- JP
- Japan
- Prior art keywords
- acetyl
- chitohexaose
- infective
- active ingredient
- hexa
- 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 - Lifetime
Links
- 239000004480 active ingredient Substances 0.000 claims description 13
- 229960005475 antiinfective agent Drugs 0.000 claims description 12
- 239000004599 antimicrobial Substances 0.000 claims description 12
- FUHDMRPNDKDRFE-LPUYKFNUSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r)-5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy- Chemical compound O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@@H]([C@H](O)[C@H](C=O)NC(=O)C)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)NC(C)=O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 FUHDMRPNDKDRFE-LPUYKFNUSA-N 0.000 claims description 10
- DPTYILOGADPXRZ-RXDSZOQSSA-N Penta-N-acetylchitopentaose Chemical compound O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@@H]([C@H](O)[C@H](C=O)NC(=O)C)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 DPTYILOGADPXRZ-RXDSZOQSSA-N 0.000 claims description 8
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 12
- 241000894006 Bacteria Species 0.000 description 11
- 230000002924 anti-infective effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- 229920002101 Chitin Polymers 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 241000186781 Listeria Species 0.000 description 2
- 206010027906 Monocytosis Diseases 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 210000000416 exudates and transudate Anatomy 0.000 description 2
- 230000036737 immune function Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 210000003200 peritoneal cavity Anatomy 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 239000006159 Sabouraud's agar Substances 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
Description
（産業上の利用分野）
本発明は、新規な抗感染症剤に関するものであ
る。
（従来の技術）
従来、抗感染症剤として抗生物質等種々のもの
が知られているが、耐性菌の出現や患者への強い
副作用を示す等の欠点を有するために新規な抗感
染症剤の出現が望まれていた。また、免疫機能が
低下した者たとえばガン患者や臓器移植等のため
に免疫抑制処置を受けた患者等は真菌類の日和見
感染を受け易く、免疫機能亢進作用を示す安全な
抗感染症剤の出現が望まれていた。このような新
規な抗感染症剤として、本発明者らは先に天然界
に多量に存在するキチンまたはキトサンを有効成
分とする抗感染症剤を提供した（特開昭59−
27827号公報）。
（発明が解決しようとする問題点）
しかしながら、キチンたはキトサンを有効成分
とする抗感染症剤はすぐれた抗感染活性をを有す
るが、キチンおよびキトサンが水不溶性の高分子
物質であるために、注射剤等の製剤化および投与
において問題点を有し、抗感染症剤として未だ充
分満足できるものではなかつた。
（問題点を解決するための手段、作用）
本発明者らは、キチンおよびキトサンの有する
問題点を解決し、更にすぐれた活性を有する薬剤
を提供すべく鋭意研究を重ねた結果、キチンを分
解して得られる水溶性のキトおよびキトサノオリ
ゴ糖の中から選ばれるペンタ−Ｎ−アセチル−キ
トペンタオースおよびヘキサ−Ｎ−アセチル−キ
トヘキサオースが以外にも抗感染症剤としてすぐ
れた特性を有することを見出し、本発明を完成す
るに至つた。
本発明の抗感染症剤はペンタ−Ｎ−アセチル−
キトペンタオースおよび／またはヘキサ−Ｎ−ア
セル−キトヘキサオースを有効成分とするもので
あり、中でもヘキサ−Ｎ−アセチル−キトヘキサ
オースを有効成分とするものが特にすぐれた効果
を示す。
本発明の抗感染症剤は有効成分のペンタ−Ｎ−
アセチル−キトペンタオースおよびヘキサ−Ｎ−
アセチル−キトヘキサオースが水溶性であるの
で、これら常法により注射剤、錠剤、粉剤等の形
に製剤し、静脈注射、経口投与等によつて使用さ
れる。
本発明の抗感染症剤はカシジダ・アルビカンス
（Candida albicans）等の真菌、黄色ブドウ球
菌、グラム陰性菌、グラム陽性菌等の各種の菌に
対しすぐれた抗感染効果を示し、その有効薬量は
体重Kg当り10〜100mgである。
（発明の効果）
本発明の抗感染症剤はカニの甲羅等に存在する
天然のキチンを分解して得られるペンタ−Ｎ−ア
セチル−キトペンタオースおよび／またはヘキサ
−Ｎ−アセチル−キトヘキサオースを有効成分と
するので人体に対する毒性、副作用がほとんどな
く、またペンタ−Ｎ−アセチル−キトペンタオー
スおよびヘキサ−Ｎ−アセチル−キトヘキサオー
スが水溶性であるために注射財投の製剤化および
投与が簡便であり、かつ薬効の発現が早い、免疫
機能亢進作用を示す等のすぐれた効果を示す。
（実施例）
製剤例
注射剤の製造
ペンタ−Ｎ−アセチル−キトペンタオース10
ｇ、注射用生理食塩水適量をとり全量1000mlと
し、第十日本薬局方注射剤の製法によつて注射剤
を得た。
実験例 １
抗感染効果試験１
製剤例に準じて調製したペンタ−Ｎ−アセチル
−キトペンタオース（実施例１）、ヘキサ−Ｎ−
アセチル−キトヘキサオース（実施例２）、また
はチキン（比較例１）を有効成分とす注射液を、
４〜６週令のBALB／Ｃ雄性マウスの腹腔内に
有効成分50mg／Kgマウス注射し、投与後３、12、
24および48時間後にハンクス緩衝液を用いて腹腔
を洗うことによつて腹腔滲出細胞を採取し、これ
を同一緩衡液に１×106細胞／ml濃度になるよう
に懸濁した。次いで、これに５ミリモルのグリコ
ールおよびジメチルスルホキシド１ml当りのルミ
ノール２mgを溶解して調製したルミノール液50μ
を加えて37℃で10分間前培養した後、化学発光
測定器Biolumat LB9500（Berthold社製）を用い
て10分間化学発光応答を測定し、活性酸素産生能
を調べることにより抗感染効果を調べた。尚、生
理食塩水のみの注射液を対照として行つた。得ら
れた結果を表−１に示す。
(Industrial Application Field) The present invention relates to a novel anti-infective agent. (Prior Art) Various anti-infective agents, such as antibiotics, have been known in the past. was expected to appear. In addition, people with weakened immune systems, such as cancer patients and patients who have undergone immunosuppressive treatment due to organ transplants, etc., are susceptible to opportunistic fungal infections, and the emergence of safe anti-infective agents that enhance immune function. was desired. As such a novel anti-infective agent, the present inventors have previously provided an anti-infective agent containing chitin or chitosan as an active ingredient, which exists in large amounts in nature (Japanese Patent Application Laid-Open No. 1983-1972).
Publication No. 27827). (Problems to be Solved by the Invention) However, anti-infective agents containing chitin or chitosan as active ingredients have excellent anti-infective activity, but since chitin and chitosan are water-insoluble polymeric substances, However, there were problems in the formulation and administration of injections, etc., and they were not yet fully satisfactory as anti-infective agents. (Means and effects for solving the problems) The present inventors have conducted extensive research to solve the problems of chitin and chitosan and provide a drug with even better activity. Penta-N-acetyl-chitopentaose and hexa-N-acetyl-chitohexaose selected from water-soluble chito- and chitosano-oligosaccharides obtained by They discovered this and completed the present invention. The anti-infective agent of the present invention is penta-N-acetyl-
It contains chitopentaose and/or hexa-N-acetyl-chitohexaose as an active ingredient, and among them, those containing hexa-N-acetyl-chitohexaose as an active ingredient show particularly excellent effects. The anti-infective agent of the present invention has an active ingredient of penta-N-
Acetyl-chitopentaose and hexa-N-
Since acetyl-chitohexaose is water-soluble, it can be formulated into injections, tablets, powders, etc. by these conventional methods, and used by intravenous injection, oral administration, etc. The anti-infective agent of the present invention exhibits excellent anti-infective effects against various bacteria such as fungi such as Candida albicans, Staphylococcus aureus, Gram-negative bacteria, and Gram-positive bacteria. It is 10-100 mg per kg of body weight. (Effects of the Invention) The anti-infective agent of the present invention is penta-N-acetyl-chitopentaose and/or hexa-N-acetyl-chitohexaose obtained by decomposing natural chitin present in crab shells, etc. As the active ingredient, there is almost no toxicity or side effects to the human body, and penta-N-acetyl-chitopentaose and hexa-N-acetyl-chitohexaose are water-soluble, making it easy to formulate and administer injections. It is simple and has excellent effects such as quick onset of efficacy and immune function enhancement effect. (Example) Production of formulation example injection Penta-N-acetyl-chitopentaose 10
g. An appropriate amount of physiological saline for injection was taken to make a total volume of 1000 ml, and an injection was obtained according to the manufacturing method for injections in No. 10 of the Japanese Pharmacopoeia. Experimental Example 1 Anti-infective Effect Test 1 Penta-N-acetyl-chitopentaose (Example 1), hexa-N-
An injection containing acetyl-chitohexaose (Example 2) or chicken (Comparative Example 1) as an active ingredient,
50 mg/Kg of the active ingredient was intraperitoneally injected into 4-6 week old BALB/C male mice, and 3, 12, 3 days after administration.
After 24 and 48 hours, the peritoneal exudate cells were collected by washing the peritoneal cavity with Hank's buffer and suspended in the same buffer at a concentration of 1×10 6 cells/ml. Next, 50μ of a luminol solution was prepared by dissolving 5 mmol of glycol and 2 mg of luminol per 1 ml of dimethyl sulfoxide.
After preincubating at 37°C for 10 minutes, the chemiluminescence response was measured for 10 minutes using a chemiluminescence analyzer Biolumat LB9500 (manufactured by Berthold), and the anti-infective effect was investigated by examining the ability to produce active oxygen. . In addition, an injection solution containing only physiological saline was used as a control. The results obtained are shown in Table-1.
【表】
下を示す。
実験例 ２
抗感染効果試験２
製剤例に準じて調製したペンタ−Ｎ−アセチル
−キトペンタオース（実施例３）、ヘキサ−Ｎ−
アセチル−キトヘキサオース（実施例４）、また
はチキン（比較例２）を有効成分とす注射液を４
〜６週令のBALB／Ｃ雄性マウスの腹腔内に有
効成分50mg／Kgマウス注射し、投与後３、12、24
および48時間後にハンクス緩衝液を用いて腹腔を
洗うことによつて腹腔滲出細胞を採取し、これを
同一緩衡液に１×105細胞／ml濃度になるように
懸濁した。次いで、これわ96穴マイクロプレート
に入れ、これに10％濃度になるように正常マウス
血清を加え、次いでカンジダ・アルビカンス
（Candida albicans）生菌200個を加え５％二酸
化炭素培養器で３時間前培養後、細胞懸濁液をサ
ブロー寒天培地に入れて27±１℃で48時間培養し
て生菌数を数え次式にり殺菌率を測定したカンジ
ダ・アルビカンス（Candidi albicans）に対する
抗感染効果を調べた。
殺菌率（％）＝200−生菌数／200×100
尚、生理食塩水のみの注射を対照として行つ
た。得られた結果を表−２に示す。[Table] Shown below.
Experimental Example 2 Anti-infective Effect Test 2 Penta-N-acetyl-chitopentaose (Example 3), hexa-N-
An injection containing acetyl-chitohexaose (Example 4) or chicken (Comparative Example 2) as an active ingredient
~6 weeks old BALB/C male mice were intraperitoneally injected with 50 mg/kg of the active ingredient, and 3, 12, 24 days after administration.
After 48 hours, the peritoneal exudate cells were collected by washing the peritoneal cavity with Hank's buffer and suspended in the same buffer solution at a concentration of 1×10 5 cells/ml. Next, place this in a 96-well microplate, add normal mouse serum to a concentration of 10%, then add 200 viable Candida albicans cells, and incubate in a 5% carbon dioxide incubator for 3 hours. After culturing, the cell suspension was placed in a Sabouraud agar medium and incubated at 27±1°C for 48 hours. The number of viable bacteria was counted and the bactericidal rate was measured using the following formula. Examined. Sterilization rate (%) = 200 - number of viable bacteria / 200 x 100 In addition, injection of only physiological saline was performed as a control. The results obtained are shown in Table-2.
【表】
％以下を示す。
実験例 ３
抗感染効果試験３
SPF−ddr雄性マウス（１群８匹）に下記の細
菌を感染させる５日前、３日前および１日前に、
それぞれ前記の製剤例に準じて調製したヘキサ−
Ｎ−アセチル−キトヘキサオースの注射液を、有
効成分50mg／Kgマウスの投与量で腹腔内に投与し
た。次いで、単球症リステリア菌（Listeria
monocytogenes）Serotype 4b株をブレインハー
トインフユージヨンのスラントに移植し37℃で培
養後に培地（Trypitcal Soy Broth）に移植、37
℃で24時間振盪培養を行い、培養停止後に生理食
塩水で菌を洗浄し菌数６×108個／mlに調製して
おいた株懸濁液の0.1ml（感染菌数６×107個）
を、上記の処理マウス腹腔内に接触感染させた。
細菌感染後15日目に生存率を求めた。
その結果、ヘキサ−Ｎ−アセチル−キトヘキサ
オースを投与処理したマウスの生存率は100％、
未投与の未処理マウス（対照）の生存率は37.5％
であつた。
実験例 ４
抗感染効果試験４
SPF−ddY雄性マウス（１群８匹）に下記の細
菌を感染させる３日前、２日前および１日前に、
それぞれ前記の製剤例に準じて調製したヘキサ−
Ｎ−アセチル−キトヘキサオースの注射液を、有
効成分50mg／Kgマウスの投与量で腹腔内に投与し
た。次いで、あらかじめ緑濃菌（Pseudomonas
aeruginosa）をブレインハートインフユージヨ
ンのスラントに移植し37℃で培養後普通ブイヨン
に移植、37℃で24時間振盪培養を行い培養停止後
に生理食塩水で菌を洗浄し菌数1.2×108個／mlに
調製しておいた菌懸濁液の0.1ml（感染菌数1.2×
107個）を上記の処理マウス静脈内に接触感染さ
せた。感染後15日目に生存率を求めた。
その結果、ヘキサ−Ｎ−アセチル−キトヘキサ
オースを投与した処理したマウスの生存率は75
％、未投与の未処理マウス（対照）の生存率は44
％であつた。[Table] Shows % or less.
Experimental Example 3 Anti-infective Effect Test 3 5 days, 3 days, and 1 day before infecting SPF-ddr male mice (8 mice per group) with the following bacteria.
Hexane prepared according to the above formulation examples, respectively.
An injection solution of N-acetyl-chitohexaose was administered intraperitoneally at a dose of 50 mg of active ingredient/Kg mouse. Then monocytosis Listeria (Listeria monocytosis)
monocytogenes) Serotype 4b strain was transplanted into the slant of Brain Heart Infusion, cultured at 37°C, and then transplanted into a medium (Trypitcal Soy Broth), 37
Culture with shaking at ℃ for 24 hours, and after stopping the culture, wash the bacteria with physiological saline and prepare 0.1 ml of the strain suspension to a number of infected bacteria of 6 x 10 8 cells/ml (number of infected bacteria 6 x 10 7 Individual)
was infected intraperitoneally with the above-treated mice.
Survival rate was determined 15 days after bacterial infection. As a result, the survival rate of mice treated with hexa-N-acetyl-chitohexaose was 100%;
Survival rate of untreated untreated mice (control) was 37.5%
It was hot. Experimental Example 4 Anti-infective Effect Test 4 Three days, two days, and one day before SPF-ddY male mice (8 mice per group) were infected with the following bacteria.
Hexane prepared according to the above formulation examples, respectively.
An injection solution of N-acetyl-chitohexaose was administered intraperitoneally at a dose of 50 mg of active ingredient/Kg mouse. Next, Pseudomonas
aeruginosa) was transplanted to the slant of Brain Heart Infusion, cultured at 37℃, transferred to ordinary broth, cultured with shaking at 37℃ for 24 hours, and after stopping the culture, the bacteria were washed with physiological saline and the number of bacteria was 1.2 x 108 . 0.1ml of a bacterial suspension prepared at a concentration of 1.2x
10 7 cells) were infected intravenously in the above-treated mice. Survival rates were determined 15 days after infection. As a result, the survival rate of mice treated with hexa-N-acetyl-chitohexaose was 75%.
%, the survival rate of untreated untreated mice (control) was 44
It was %.
Claims (1)
よび／またはヘキサ−Ｎ−アセチル−キトヘキサ
オースを有効成分とする抗感染症剤。1. An anti-infective agent containing penta-N-acetyl-chitopentaose and/or hexa-N-acetyl-chitohexaose as an active ingredient.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25276184A JPS61130230A (en) | 1984-11-29 | 1984-11-29 | Anti-infective |
| CA000496106A CA1261264A (en) | 1984-11-29 | 1985-11-25 | Immunopotentiating agents and method |
| DK550685A DK165731C (en) | 1984-11-29 | 1985-11-28 | USE OF CHITIN OR CHITOSANOL OIGOMERS FOR THE PREPARATION OF IMMUNOPOTENSIVE AGENTS |
| DE8585308687T DE3583217D1 (en) | 1984-11-29 | 1985-11-28 | USE OF CHITIN OR CHITOSAN OLIGOMERS FOR PRODUCING A MEDICINAL PRODUCT FOR STRENGTHENING THE DEFENSE FORCES AGAINST BACTERIA AND MUSHROOM INFECTIONS AND AGAINST TUMOR GROWTH. |
| EP85308687A EP0183556B1 (en) | 1984-11-29 | 1985-11-28 | Use of chitin- or chitosan-oligomers for the manufacture of a immunopotentiating agent for enhancing the immune response against bacterial and fungal infections and against the growth of tumours |
| US07/363,307 US4971956A (en) | 1984-11-29 | 1989-06-07 | Immunopotentiating agents and method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25276184A JPS61130230A (en) | 1984-11-29 | 1984-11-29 | Anti-infective |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61130230A JPS61130230A (en) | 1986-06-18 |
| JPH0481967B2 true JPH0481967B2 (en) | 1992-12-25 |
Family
ID=17241922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25276184A Granted JPS61130230A (en) | 1984-11-29 | 1984-11-29 | Anti-infective |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61130230A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001031577A (en) * | 1999-07-16 | 2001-02-06 | Fujibio Co Ltd | Inhibition of side effect of cisplatin by chitin chitosan and formulation therefor |
| JP2001031575A (en) * | 1999-07-16 | 2001-02-06 | Fujibio Co Ltd | Inhibition of side effect of 5-fluorouracil by chitin chitosan and formulation therefor |
-
1984
- 1984-11-29 JP JP25276184A patent/JPS61130230A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61130230A (en) | 1986-06-18 |
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