JPH01299232A - Lyophilized injection of stable canrenoate potassium - Google Patents
Lyophilized injection of stable canrenoate potassiumInfo
- Publication number
- JPH01299232A JPH01299232A JP12997288A JP12997288A JPH01299232A JP H01299232 A JPH01299232 A JP H01299232A JP 12997288 A JP12997288 A JP 12997288A JP 12997288 A JP12997288 A JP 12997288A JP H01299232 A JPH01299232 A JP H01299232A
- Authority
- JP
- Japan
- Prior art keywords
- injection
- potassium
- stable
- lyophilized
- basic amino
- 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.)
- Granted
Links
- 238000002347 injection Methods 0.000 title claims abstract description 28
- 239000007924 injection Substances 0.000 title claims abstract description 28
- 229960000206 potassium canrenoate Drugs 0.000 title claims abstract description 23
- JTZQCHFUGHIPDF-RYVBEKKQSA-M potassium canrenoate Chemical compound [K+].O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)CCC([O-])=O)[C@@H]4[C@@H]3C=CC2=C1 JTZQCHFUGHIPDF-RYVBEKKQSA-M 0.000 title claims description 22
- 150000001413 amino acids Chemical class 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 6
- PBKZPPIHUVSDNM-WNHSNXHDSA-N canrenoic acid Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)CCC(O)=O)[C@@H]4[C@@H]3C=CC2=C1 PBKZPPIHUVSDNM-WNHSNXHDSA-N 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 5
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 abstract description 4
- 229960002823 canrenoic acid Drugs 0.000 abstract description 4
- 239000003381 stabilizer Substances 0.000 abstract description 4
- 239000004475 Arginine Substances 0.000 abstract description 3
- 230000007774 longterm Effects 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 abstract description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 abstract description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 abstract description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 abstract description 2
- 229960003104 ornithine Drugs 0.000 abstract description 2
- 239000005557 antagonist Substances 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 239000002395 mineralocorticoid Substances 0.000 abstract 1
- 238000004321 preservation Methods 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 6
- 239000003708 ampul Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 5
- 229930064664 L-arginine Natural products 0.000 description 5
- 235000014852 L-arginine Nutrition 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 229960002885 histidine Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 229940122522 Mineralocorticoid antagonist Drugs 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- -1 hydrated sodium Chemical compound 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002394 mineralocorticoid antagonist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、カンレノ酸カリウム凍結乾燥注射系に関し、
更に詳細には安定剤として塩基性アミノ酸を少を宮有し
、長時間保存しても一値の変動が少なく、シかも溶解時
に「おり」、「メ＜」等の不＃＊の発生がない安定なカ
ンレノ酸カリウム凍結乾燥注射系に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a lyophilized injection system for potassium canrenoate,
More specifically, it contains a small amount of basic amino acids as a stabilizer, so there is little fluctuation in the value even when stored for a long time, and there is no possibility of occurrence of irregularities such as "cold" or "me<" when dissolved. Regarding the stable potassium canrenoate lyophilized injection system.
カンレノ酸はアルドステロンのもつ？Ｅ解質代謝作用に
拮抗し、このカリウム塩でめるカンレノ゛酸カリウムは
強力なミネラルコルチコイド拮抗剤として有用な薬物で
ある。Does canrenoic acid have aldosterone? Potassium canrenoate, which antagonizes the metabolic effects of E-lyte, is a useful drug as a potent mineralocorticoid antagonist.
カンレノ酸カリウムを水溶液注射薬とするには、加熱６
ＩＣ鉋を行なうとダル化を生じるため、無菌操作により
調製する必要がるる。また薫陶操作によりｆＡ＃！Ｌ、
たとしても、この水＃液は経時的に水に不浴性のカンレ
ノ酸を生成し、それが「おり」、「ろく」等の不ｆ６ｖ
Ｊとなって現われ、品質的に満足できる本のは得られな
い。そのため粉末小分は製剤、凍結乾燥製剤等の粉末製
剤とする必要が生じる。To make canrenoic acid potassium into an aqueous solution injection, heat 6
IC planing causes dulling, so it must be prepared using aseptic techniques. Also, fA# due to nurturing operation! L,
Even if this water solution generates canrenoic acid, which is non-bathable in water, over time, it will cause problems such as "ori" and "roku".
J, and you will not be able to get a book that is satisfactory in terms of quality. Therefore, it becomes necessary to make powder preparations into powder preparations such as preparations and freeze-dried preparations.
しかし、粉末小分は製剤は、製造時の無菌性確保が鎌し
いため、従来カンレノばカリウムは凍結乾燥製剤として
提供されていた。However, since it is difficult to ensure sterility during manufacture of small powder preparations, Canrenoba Potassium has conventionally been provided as a freeze-dried preparation.
また、カンレノ酸カリウムは、−８〜ｌ。Moreover, potassium canrenoate is -8~l.
付近でもつとも安定であるが、経時的に−が下降するこ
とにより「おり」、「め〈」尋の不溶物が生成すること
が知られている。Although it is stable even in the vicinity, it is known that as the value of - decreases over time, insoluble matter of ``cold'' and ``medium'' forms.
そこで、−の下降を防ぎ、−埴を８〜１０に維持するよ
うに各種の緩衝剤を用いた凍結乾床注射楽が検討されて
いるが、−安定性や人体への安全性という点から満足で
きるものは未だ少ない。例えば、脣公昭５６−１７３２
６号では、緩衝剤としてトリス（ヒドロキシメチル）ア
ミノメタンを添加することにより上記課題の解決を図っ
ているが、このトリス（ヒドロキシメチル）アミノメタ
ンは、医薬品に対する使用前例が乏しく、注射薬に添加
するには安全性の面から考えて好ましいとはいえないも
のであった。Therefore, freeze-dried bed injection using various buffering agents is being considered to prevent the drop of - and maintain - to a level of 8 to 10, but from the viewpoint of - stability and safety to the human body, There are still very few things that satisfy me. For example,
No. 6 attempts to solve the above problem by adding tris(hydroxymethyl)aminomethane as a buffering agent, but this tris(hydroxymethyl)aminomethane has little precedent for use in pharmaceuticals and has not been added to injections. This was not desirable from a safety standpoint.
従って、安全性に優れた安定剤を用い、長時間保存して
も一憚の変動が少なく、復水時に不溶物のない安定なカ
ンレノ戚カリウム注射薬の提供が望まれていた。Therefore, it has been desired to provide a stable canreno-related potassium injection that uses a stabilizer with excellent safety, exhibits little fluctuation during long-term storage, and is free of insoluble matter upon condensation.
（ｉｌ１題を解決するための手段〕
不発明者らは、カンレノ酸カリウム注射楽の安定剤とし
て用いることができ、しかも安全性の高い添加祷につい
て鋭意研究を行なった結果、塩基性アミノ酸を少量添加
して凍結乾燥することによシ、長時間保存後においても
−１の変動が極めて少なく、かつ性状の面からも「おシ
」、「あく」等の不溶物の生じないカンレン酸カリウム
粉末注射系が得られることを見出した。(Means for Solving Problem 1) The inventors have conducted intensive research on additives that can be used as stabilizers for potassium canrenoate injections and are highly safe. By adding the powder and freeze-drying it, it is possible to obtain a potassium kanrenate powder that has very little -1 fluctuation even after long-term storage, and does not produce insoluble matter such as "stain" or "scum" in terms of properties. It has been found that an injection system can be obtained.
すなわち本発明は、カンレノ酸カリウムと、これに対し
て０．５重重％以上の塩基性アきノ酸を含有してなる安
定なカンレノ酸カリウム凍結乾燥注射系を提供するもの
でるる。That is, the present invention provides a stable lyophilized potassium canrenoate injection system containing potassium canrenoate and 0.5% by weight or more of a basic anoic acid based on the potassium canrenoate.
本発明のカンレノはカリウム凍緒乾旅注射楽は、カンレ
ノ酸カリウムと、これに対して０、５重量％以上の塩基
性アミノ酸を水に溶解し、ＩＪｌ！要に応じて塩酸等の
酸や水醒化ナトリウム等の塩基によりｐＨを８〜ｌＯに
、、４１１Ｆした後、常法によシ凍結乾珠することによ
シ製造される。The canreno potassium freeze-dried injection of the present invention is prepared by dissolving potassium canrenoate and basic amino acids of 0.5% or more by weight relative to the potassium in water. If necessary, the pH is adjusted to 8 to 10F with an acid such as hydrochloric acid or a base such as hydrated sodium, and then freeze-dried according to a conventional method.
本発明に便用する塩基性アミノ酸としては。Basic amino acids useful in the present invention include:
例エバアルギニン、オルニチン、ヒスチジン。Examples evaarginine, ornithine, histidine.
リシン等が挙げられるが、脣にアルギニンが好ましい。Examples include lysine, but arginine is preferred.
これらは光学異性体の区別なく使用できる。塩基性アミ
ノ酸の使用量がカンレノ酸カリウムに対しα５重重％に
満たないと、緩ＷＩ能力がないため製剤の安定化が図れ
ない。These can be used without distinction of optical isomers. If the amount of basic amino acid used is less than α5% by weight based on potassium canrenoate, the formulation cannot be stabilized because it does not have a slow WI ability.
また塩基性アミノ酸の使用量の上限に制限はないが、一
般に経済性や製剤化等の面から５重重％程度で充分でる
る。Although there is no upper limit to the amount of basic amino acids to be used, generally about 5% by weight is sufficient from the viewpoint of economy and formulation.
斯くして得られた本発明のカンレノ酸カリウム凍結乾燥
注射系は、長時間保存しても安定で、−値のＫＩＩＪが
極めて少なく、また性状の面でも、「おり」、「ろく」
等の不溶物の生成はない。また安定性同上のための添加
剤がアミノ酸であるため、安全性についても全く問題な
く、注射薬として好適でるる。The thus obtained lyophilized potassium canrenoate injection system of the present invention is stable even when stored for a long time, has extremely low negative KIIJ values, and has good properties such as "Ori" and "Roku".
There is no formation of insoluble substances such as. Furthermore, since the additive for stability is an amino acid, there is no problem with safety and it is suitable as an injection drug.
次に実施例及び比較例を挙げ、本発明を更に詳しく説明
する。Next, the present invention will be explained in more detail with reference to Examples and Comparative Examples.
実施例１
カンレノ酸カリウム１００ｔを注射用蒸留水３００−に
溶Ｍ後、これにＬ−アルギニン２、ｓｒを注射用蒸留水
１００ゴに溶解したものを加えた。混合後０．１ Ｎ塩
ｒＲ金用いて−を９．５に調整し、次に注射用蒸留水を
用いて５００−に補正し友。これを０．２２μｍのメン
ブランフィルタ−により無菌ろ過しｓＲ園条件下、畝困
された３７！アングルにｌ−ずつ分注した。常法により
凍結乾脈を行なった後、無菌条件下アンプルを溶閉し、
下記注射系を得た。Example 1 100 tons of potassium canrenoate was dissolved in 300 g of distilled water for injection, and then L-arginine 2, sr dissolved in 100 g of distilled water for injection was added thereto. After mixing, the - was adjusted to 9.5 using 0.1 N salt rR gold, and then corrected to 500 using distilled water for injection. This was sterile filtered using a 0.22 μm membrane filter and subjected to 37! The solution was dispensed in liter portions into angle tubes. After freeze-drying the pulse using the usual method, the ampoule was melted and closed under aseptic conditions.
The following injection system was obtained.
１アンプル中
カンレノ酸カリウム ２００■Ｌ−アルギニ
ン ５哩（ｍ：９．５０）
実施例２
一調螢を行なわない以外は実施例１と同様にして下記注
射薬を得た。Potassium canrenoate 200 μL-arginine 5 μg (m: 9.50) in 1 ampoule Example 2 The following injection drug was obtained in the same manner as in Example 1, except that one-shot fireflying was not performed.
１アンプル中
カンレノ酸カリウム ２００哩Ｌ−しルギニ
ン ２ｍ’１（ｐ）ｌ：９．８５）
実ａ例３
Ｌ−アルギニンの代わシにＬ−リシンを用いる以外は実
施例２と同様にして下記注射薬を得た。Potassium canrenoate in 1 ampoule 200 kg L-luginine 2 m'1 (p) l: 9.85) Example 3 The following procedure was carried out in the same manner as in Example 2 except that L-lysine was used instead of L-arginine. I got an injection.
１アングル中
カンレノ酸カリウム ２００ｍ９Ｌ−リシン
６■（…：９．５０）
実施例４
Ｌ−アルギニンの代わりにＬ−ヒスチジンを添加し、ま
た塩酸の代わりに水酸化ナトリウムを用いて一調整を行
なう以外は実施例１と同様にして下記注射薬を得た。Potassium canrenoate in 1 angle 200m9L-lysine 6■ (...:9.50) Example 4 Except for making one adjustment by adding L-histidine instead of L-arginine and using sodium hydroxide instead of hydrochloric acid. The following injection drug was obtained in the same manner as in Example 1.
１アンプル中
カンレノ酸カリウム ２００肩ｇＬ−ヒスチ
ゾン ６ｑ（ｐＨ：９．５０）
比較例Ｉ
Ｌ−アルギニンを添加しない以外は実施例２と同様にし
て下記注射系を得た。Potassium canrenoate 200 g in 1 ampoule L-histizone 6q (pH: 9.50) Comparative Example I The following injection system was obtained in the same manner as in Example 2 except that L-arginine was not added.
１アンプル中
カンレノ酸カリウム ２００■（ｐＨＳ＆４
３）
比較例２
Ｌ−アルギニンの代わりにＮａ冨ｎｐｏ４・１２ＨｚＯ
ｉ ７．５ を及びＮａ３ＰＯ４・１２ Ｈ！Ｏｔ−０
，６を用いる以外は実施例２と同様にして下記注射系を
得た。Potassium canrenoate 200■ (pHS&4) in 1 ampoule
3) Comparative Example 2 Natompo4・12HzO instead of L-arginine
i 7.5 and Na3PO4・12 H! Ot-0
, 6 was used in the same manner as in Example 2 to obtain the following injection system.
１アンプル中
カンレノ酸カリウム ２００■Ｎａｇ）ｉＰ
Ｏ４−１２Ｈ！０ １５ ｍ９Ｎａ３Ｐ
Ｏ４・ １ ２Ｍ！ＯＬ２ｍ９（ＩＩＨ：９．６１）
実施例５
上記実施例１〜４及び比較例１．２で得た凍結乾燥注射
薬について、製造直後ｓ ４０Ｃで３ケ月保存後及び６
０Ｃで１ケ月保存後におｈて％ ２−の注射用蒸留水で
復水し、その−値の測定及び不＃吻の生成状況の観察を
行なった。Potassium canrenoate in 1 ampoule 200 ■ Nag) iP
O4-12H! 0 15 m9Na3P
O4・12M! OL2m9 (IIH: 9.61) Example 5 Regarding the freeze-dried injections obtained in Examples 1 to 4 and Comparative Example 1.2, immediately after manufacture, after storage at 40C for 3 months, and after storage at 40C for 3 months,
After being stored at 0C for one month, the water was condensed with 2% distilled water for injection, and the -value was measured and the state of formation of the proboscis was observed.
その結果を第１表に示す。The results are shown in Table 1.
以下余白
ｍ：不溶物なし
±：不溶′９１Ｊ５ｒわずかｌｃｇめる＋：不溶’ＩＩ
Ｉ全認める
←：不溶物を多く認める
第１表から明らかなように１本発明のカンレノ酸カリウ
ム凍結乾燥注射系は、経時的な一値の変動が極めて小石
＜、また「おり」、「ろく」等の不溶物の生成がなく、
比較例に比して優れた効果を有する。Below margin m: No insoluble material ±: Insoluble '91J5r slightly lcg +: Insoluble 'II
As is clear from Table 1, the potassium canrenoate lyophilized injection system of the present invention exhibits extremely large fluctuations in one value over time, as well as ``sore'' and ``roku''. There is no formation of insoluble substances such as
It has a superior effect compared to the comparative example.
以上that's all
Claims (1)
以上の塩基性アミノ酸を含有してなる安定なカンレノ酸
カリウム凍結乾燥注射薬。1. Potassium canrenoate and 0.5% by weight of this
A stable lyophilized potassium canrenoate injection containing the above basic amino acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12997288A JPH0643316B2 (en) | 1988-05-27 | 1988-05-27 | Method for producing stable lyophilized potassium canrenoate injection |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12997288A JPH0643316B2 (en) | 1988-05-27 | 1988-05-27 | Method for producing stable lyophilized potassium canrenoate injection |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01299232A true JPH01299232A (en) | 1989-12-04 |
| JPH0643316B2 JPH0643316B2 (en) | 1994-06-08 |
Family
ID=15022990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12997288A Expired - Lifetime JPH0643316B2 (en) | 1988-05-27 | 1988-05-27 | Method for producing stable lyophilized potassium canrenoate injection |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0643316B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998034623A1 (en) * | 1997-02-05 | 1998-08-13 | Kirin Beer Kabushiki Kaisha | Freeze-dried composition containing glycosphingolipid and process for producing the same |
| US6417167B1 (en) | 1997-02-05 | 2002-07-09 | Kirin Beer Kabushiki Kaisha | Lyophilized compositions containing shingoglycolipid and process for preparing them |
-
1988
- 1988-05-27 JP JP12997288A patent/JPH0643316B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998034623A1 (en) * | 1997-02-05 | 1998-08-13 | Kirin Beer Kabushiki Kaisha | Freeze-dried composition containing glycosphingolipid and process for producing the same |
| US6417167B1 (en) | 1997-02-05 | 2002-07-09 | Kirin Beer Kabushiki Kaisha | Lyophilized compositions containing shingoglycolipid and process for preparing them |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0643316B2 (en) | 1994-06-08 |
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