JPS631947B2 - - Google Patents
Info
- Publication number
- JPS631947B2 JPS631947B2 JP11667679A JP11667679A JPS631947B2 JP S631947 B2 JPS631947 B2 JP S631947B2 JP 11667679 A JP11667679 A JP 11667679A JP 11667679 A JP11667679 A JP 11667679A JP S631947 B2 JPS631947 B2 JP S631947B2
- Authority
- JP
- Japan
- Prior art keywords
- substance
- base
- sewing machine
- hotei
- reaction
- 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
Links
- 239000000126 substance Substances 0.000 claims description 14
- 238000009958 sewing Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002585 base Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241000187708 Micromonospora Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229940126574 aminoglycoside antibiotic Drugs 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 241000187723 Micromonospora sp. Species 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 mono- Chemical compound 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Description
【発明の詳細な説明】
本発明はアミノ配糖体抗生物質であるホーテイ
ミシンＡの新規な製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing hortimicin A, an aminoglycoside antibiotic.
更に詳しく述べれば、新規アミノ配糖体抗生物
質であるSF−2052物質を塩基で処理することに
よりホーテイミシンＡを生成せしめ、これよりホ
ーテイミシンＡを採取することにある。 More specifically, the present invention involves treating SF-2052, a novel aminoglycoside antibiotic, with a base to produce Houtimicin A, and then collecting Houtimicin A from this.
ホーテイミシンＡは次の構造式(1)を有し、カナ
マイシン、ゲンタミシン耐性菌を含むグラム陽性
菌及びグラム陰性菌に活性を示す有用な抗生物質
である。 Hortimicin A has the following structural formula (1) and is a useful antibiotic that exhibits activity against Gram-positive bacteria and Gram-negative bacteria, including bacteria resistant to kanamycin and gentamicin.
ホーテイミシンＡはミクロモノスポラ・オリボ
アステロスポラによつて醗酵生産されることが知
られている（特開昭50−29789号公報）が、通常
はホーテイミシンＢ、Ｃ、Ｄ、KE、KO等の副
生物を伴つて生産される。 It is known that Hortei sewing machine A is produced by fermentation by Micromonospora oliboasterospora (Japanese Patent Application Laid-Open No. 1983-29789), but it is usually produced by fermentation of Hortei sewing machines B, C, D, KE, KO, etc. Produced with living organisms.
従つてホーテイミシンＡの製造に当つては、こ
れら副生物の分離操作及びそれに伴うホーテイミ
シンＡの収率低下は避けられない。 Therefore, in the production of Hotei Sewing Machine A, separation operations of these by-products and the accompanying decrease in the yield of Houtei Sewing Machine A are unavoidable.
本発明者等は、ホーテイミシンＡの効率的な製
造法について種々研究した結果、本発明者等によ
つて別途に見出された新抗生物質SF−2052物質
を塩基で処理することによつて高収率でホーテイ
ミシンＡに変換できることを発見して、本発明を
完成させた。 As a result of various studies on efficient production methods for Hotei Micin A, the present inventors have discovered that SF-2052, a new antibiotic substance separately discovered by the present inventors, can be highly purified by treating it with a base. The present invention was completed by discovering that it could be converted to Hotei Sewing Machine A with high yield.
SF−2052物質は式(2)によつて示す構造を有し、
ダクテイロスポランギム・マツザキエンゼSF−
2052株（微工研菌寄第4670号）及びミクロモノス
ポラ属SF−2098株（微工研菌寄第5073号）によ
つて生産される新規抗生物質である（本出願人の
出願に係る特願昭53−135921号及び得願昭54−
92642号明細書参照）。 SF-2052 substance has the structure shown by formula (2),
Dactyrosporangim Matsuzakienze SF−
It is a new antibiotic produced by Micromonospora strain SF-2098 (Feikoken Bibori No. 5073) and Micromonospora sp. Patent application No. 135921 (1981) and special application No. 135921 (1982)
92642).
前記生産菌は実質的にSF−2052物質を主成分
として生産するため、副生物の分離操作なしに高
収量で得ることができる。 Since the production bacterium produces the SF-2052 substance as a main component, it can be obtained in high yield without separation of by-products.
SF−2052物質は従来のアミノ配糖体抗生物質
とは異なつて、アルカリに比較的不安定であると
いう特徴を有する。本発明者等はその原因を探究
した結果、SF−2052物質の分子中に含まれるホ
ルムイミノ基が比較的温和な塩基処理によつて特
異的に分解することを見い出した。さらにSF−
2052物質のアルカリ分解は使用する塩基の種類及
び溶媒によつて大きな影響を受け、加水分解を過
激な条件下で行うとSF−2052物質のホルムイミ
ノグリシル基が脱離されて抗菌活生の微弱なホー
テイミシンＢにまで分解されてしまうことも判明
した。 SF-2052 substance differs from conventional aminoglycoside antibiotics in that it is relatively unstable to alkalis. The present inventors investigated the cause and found that the formimino group contained in the molecule of SF-2052 substance is specifically decomposed by relatively mild base treatment. More SF-
The alkaline decomposition of 2052 substance is greatly affected by the type of base and solvent used, and if hydrolysis is performed under extreme conditions, the formiminoglycyl group of SF-2052 substance is eliminated and the antibacterial activity is lost. It was also discovered that it was decomposed into the weak Hotei Sewing Machine B.
したがつて本発明の目的とするホーテイミシン
Ａの取得のためには、塩基による処理を比較的温
和な条件で、SF−2052物質のホルムイミノ基が
脱離されるまで行なうことが肝要である。かかる
目的のために最適の塩基処理条件は使用される塩
基の種類、その濃度、溶媒の種類、原料物質の形
態及びその濃度、温度、時間等の処理条件を相互
に適宜勘案して選定されるべきであり、通常個々
特定の場合について実験的に決定し得る。 Therefore, in order to obtain Houtimicin A, which is the object of the present invention, it is important to carry out the treatment with a base under relatively mild conditions until the formimino group of the SF-2052 substance is eliminated. The optimal base treatment conditions for this purpose are selected by appropriately considering the type of base used, its concentration, the type of solvent, the form of the raw material, and treatment conditions such as its concentration, temperature, and time. and can usually be determined experimentally for each particular case.
本発明の処理に使用する塩基としては、苛性ソ
ーダ、苛性カリ、アンモニア、アンモニア水、水
酸化バリウム、水酸化カルシウム、炭酸ナトリウ
ム、炭酸カリウム、炭酸水素ナトリウム、炭酸水
素カリウム等のアルカリ金属又はアルカリ土金属
の水酸化物、炭酸塩又は重炭酸塩のごとき無機塩
基；及びトリメチルアミン、トリエチルアミン、
エチルアミン、ジエチルアミン、ブチルアミンの
ごときモノ、ジ及びトリアルキルアミン及びピペ
ラジン、Ｎ−エチルピペラジンのごとき環式アミ
ン等の有機塩基が用いられる。反応溶媒としては
通常水が常用されるが、メタノール、エタノー
ル、ジオキサン、Ｎ・Ｎ−ジメチルホルムアミ
ド、ジメチルスルホキサイド及びそれらの含水溶
媒も本反応に好適な溶媒である。 Bases used in the treatment of the present invention include alkali metals or alkaline earth metals such as caustic soda, caustic potash, ammonia, aqueous ammonia, barium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. inorganic bases such as hydroxides, carbonates or bicarbonates; and trimethylamine, triethylamine,
Organic bases such as mono-, di- and trialkylamines such as ethylamine, diethylamine, butylamine and cyclic amines such as piperazine, N-ethylpiperazine are used. Although water is usually used as a reaction solvent, methanol, ethanol, dioxane, N.N-dimethylformamide, dimethyl sulfoxide, and their water-containing solvents are also suitable solvents for this reaction.
原料であるSF−2052物質としては純品は勿論、
その部分精製品やSF−2052物質を含む醗酵液
等を用いることができる。 The raw material SF-2052 substance is of course pure,
A partially purified product thereof, a fermentation liquid containing the SF-2052 substance, etc. can be used.
反応温度及び反応時間は、使用する塩基の種類
及び溶媒によつて異なるが、通常20〜70℃の温度
条件下で反応時間１〜20時間が適当である。 The reaction temperature and reaction time vary depending on the type of base and solvent used, but a reaction time of 1 to 20 hours is usually suitable at a temperature of 20 to 70°C.
反応終了後、目的化合物は通常のアミノ配糖体
の精製法によつて単離される。例えば、反応液を
中和後、アンバーライトIRC50（NH4 +型）のよう
な陽イオン交換樹脂に吸着させ、水洗後希アンモ
ニア水で溶離すれば目的化合物を純粋に得ること
ができる。 After the reaction is completed, the target compound is isolated by a conventional aminoglycoside purification method. For example, the target compound can be obtained in a pure form by neutralizing the reaction solution, adsorbing it on a cation exchange resin such as Amberlite IRC50 (NH 4 + type), washing with water, and eluting with dilute aqueous ammonia.
次に本発明の実施例を示すが、本発明はこれら
によつて何ら限定されるものではない。 Next, examples of the present invention will be shown, but the present invention is not limited thereto.
実施例 １
SF−2052物質硫酸塩1.0ｇを水100mlに溶解し、
苛性ソーダにてPH9.0とし、45℃に３時間加温し
た。この加水分解液の一部をマイクロボンダパツ
クC18を使用する高速液体クロマトグラフイー
（使用溶媒：0.065M PIC Ｂ−７＋0.2M
Na2SO4、螢光分析にて検出）にかけ、検定した
所、原料のSF−2052物質のピークの残存は５％
以下で、ほとんどがホーテイミシンＡに変換され
ていた。Example 1 1.0g of SF-2052 substance sulfate was dissolved in 100ml of water,
The pH was adjusted to 9.0 with caustic soda, and the mixture was heated to 45°C for 3 hours. A portion of this hydrolyzed solution was subjected to high performance liquid chromatography using Microbondapak C 18 (solvent used: 0.065M PIC B-7 + 0.2M
Na 2 SO 4 (detected by fluorescence analysis) and verified that 5% of the peak of the raw material SF-2052 substance remained.
Below, most of the machines have been converted to Hotei Sewing Machine A.
反応液は5N塩酸水にて中和後、アンバーライ
トCG−50（NH4 +）200mlを充填した塔にかけ、
１の水で洗浄後、0.2Nアンモニア水で溶離す
ると、100ml分画でフラクシヨン36〜52にかけて
抗菌活性を有する分画が得られる。 After neutralizing the reaction solution with 5N hydrochloric acid, it was poured into a column filled with 200ml of Amberlite CG-50 (NH 4 + ).
After washing with water in step 1, elution with 0.2N aqueous ammonia yields fractions with antibacterial activity in 100 ml fractions, which are divided into fractions 36 to 52.
この活性フラクシヨン約1.6を減圧濃縮し、
凍結乾燥するとホーテイミシンＡの遊離塩基380
mgが白色粉末として得られた。 Approximately 1.6 of this active fraction was concentrated under reduced pressure.
When freeze-dried, the free base of Hotei Sewing Machine A 380
mg was obtained as a white powder.
実施例 ２
SF−2052物質塩酸塩500mgを0.1Nアンモニア水
40mlに溶解し、50℃にて１時間加温した。反応液
を濃縮乾固し、水10mlに溶解し、アンバーライト
CG−50（NH4 +型）80mlを充填したカラムにか
け、0.2Nアンモニア水で溶離する。ホーテイミ
シンＡを含有する区分を集め濃縮の後、凍結乾燥
してホーテイミシンＡ遊離塩基の白色粉末180mg
を得た。Example 2 500mg of SF-2052 substance hydrochloride in 0.1N ammonia water
The solution was dissolved in 40 ml and heated at 50°C for 1 hour. Concentrate the reaction solution to dryness, dissolve in 10 ml of water, and add Amberlite.
Apply to a column packed with 80 ml of CG-50 (NH 4 + form) and elute with 0.2N aqueous ammonia. The fraction containing Houteimicin A is collected, concentrated, and lyophilized to obtain 180 mg of white powder of Houteimicin A free base.
I got it.
Claims (1)
シンＡを生成せしめ、これよりホーテイミシンＡ
を採取することを特徴とするホーテイミシンＡの
製造法。1. Treat the SF-2052 substance with a base to generate Hortei Mishin A, and from this, Hortei Mishin A
1. A method for producing Hotei Sewing Machine A, which comprises collecting .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11667679A JPS5640698A (en) | 1979-09-13 | 1979-09-13 | Preparation of fortimicin a |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11667679A JPS5640698A (en) | 1979-09-13 | 1979-09-13 | Preparation of fortimicin a |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5640698A JPS5640698A (en) | 1981-04-16 |
| JPS631947B2 true JPS631947B2 (en) | 1988-01-14 |
Family
ID=14693117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11667679A Granted JPS5640698A (en) | 1979-09-13 | 1979-09-13 | Preparation of fortimicin a |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5640698A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07277395A (en) * | 1994-04-04 | 1995-10-24 | Yoshikatsu Fujiwara | Mobile silo for cement or the like |
-
1979
- 1979-09-13 JP JP11667679A patent/JPS5640698A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5640698A (en) | 1981-04-16 |
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