JPS603043B2 - Composition for rectal administration of insulin - Google Patents
Composition for rectal administration of insulinInfo
- Publication number
- JPS603043B2 JPS603043B2 JP51092131A JP9213176A JPS603043B2 JP S603043 B2 JPS603043 B2 JP S603043B2 JP 51092131 A JP51092131 A JP 51092131A JP 9213176 A JP9213176 A JP 9213176A JP S603043 B2 JPS603043 B2 JP S603043B2
- Authority
- JP
- Japan
- Prior art keywords
- insulin
- rectal administration
- oil
- composition
- administration
- 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
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 title claims description 52
- 102000004877 Insulin Human genes 0.000 title claims description 26
- 108090001061 Insulin Proteins 0.000 title claims description 26
- 229940125396 insulin Drugs 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 title claims description 7
- -1 alkyltrimethylammonium halide Chemical class 0.000 claims description 2
- 239000008280 blood Substances 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000283977 Oryctolagus Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 102000005237 Isophane Insulin Human genes 0.000 description 1
- 108010081368 Isophane Insulin Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- HXWGXXDEYMNGCT-UHFFFAOYSA-M decyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)C HXWGXXDEYMNGCT-UHFFFAOYSA-M 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 102000018146 globin Human genes 0.000 description 1
- 108060003196 globin Proteins 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- XCOHAFVJQZPUKF-UHFFFAOYSA-M octyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](C)(C)C XCOHAFVJQZPUKF-UHFFFAOYSA-M 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- AQZSPJRLCJSOED-UHFFFAOYSA-M trimethyl(octyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(C)C AQZSPJRLCJSOED-UHFFFAOYSA-M 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
【発明の詳細な説明】
本発明は、インシュリンにハロゲン化アルキルトリメチ
ルアンモニウムを混和させることを特徴とするインシュ
リン直腸投与用組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a composition for rectal administration of insulin, characterized in that an alkyltrimethylammonium halide is mixed with insulin.
インシュリンは血糖低下剤として特に有用な薬剤であり
、注射による投与法が唯一の方法をして使用されている
。そしてインシュリンを必要とする糖尿病患者は殆んど
生涯にわたり毎日注射を繰り返さなければならないので
医師、患者にとって極めて繁雑であり、精神的肉体的苦
痛など大きな負担となっている。このようなインシュリ
ン投与にともなう難点を改良すべく近年直腸投与製剤の
開発が行なわれており、たとえばインシュリンに水、オ
リーブ油およびェマノーン４１１虫菌を演じたもの（東
京医大雑誌、２１巻、１３５頁、１９６３年）やインシ
ュリンに水、オリーブ油およびＨＣＯ−６０■を混じた
もの（日本薬学会第９３羊会講演要旨集第Ｗ分冊１９７
８王４月第１９６頁）等が報告されているが、これらの
製剤は動物実験において何れもインシュリンの投与量が
注射の場合に比較して著しく多量となっている。しかも
インシュリンの高単位の投与は患者の必要量のコントロ
ールが難しく、また、万一多量に吸収された場合に引き
起こされる低血糖症状を考慮するときわめて危険なもの
である。そこで本発明者等はより少ないインシュリンの
投与量で効率的な血糖低下作用を発現する直腸投与製剤
を鋭意研究の結果、頭記の如きインシュリン組成物を見
出したのである。Insulin is a particularly useful drug as a hypoglycemic agent, and the only way it is administered is by injection. Diabetic patients who require insulin must repeat injections every day for most of their lives, which is extremely tedious for doctors and patients, and places a great burden on them, including mental and physical pain. In recent years, rectal administration preparations have been developed in order to improve the difficulties associated with insulin administration. 1963) and insulin mixed with water, olive oil, and HCO-60 (Pharmaceutical Society of Japan 93rd Annual Meeting Abstracts Volume W 197)
8 King, April, p. 196), but in animal experiments, the amount of insulin administered in all of these preparations was significantly higher than in the case of injection. Moreover, administration of high doses of insulin makes it difficult to control the amount required by the patient, and is extremely dangerous considering the hypoglycemic symptoms that may occur if a large amount is absorbed. Accordingly, the present inventors have conducted extensive research into rectal administration preparations that exhibit an efficient hypoglycemic effect with a smaller dose of insulin, and as a result, have discovered the insulin composition described above.
次に本発明の組成物の効果を示す実験例を挙げる。Next, experimental examples showing the effects of the composition of the present invention will be given.
実験例
本発明組成物、インシュリン油性基剤に分散させたもの
（対照）とをそれぞれ家鬼に投与し血糖を比較した。Experimental Example The composition of the present invention and insulin dispersed in an oily base (control) were administered to house demons, and blood sugar levels were compared.
家鬼直腸への投与方法は２劉時間絶食した体重約２ｋ９
の雄性家兎の直腸へ小注射筒を用いて１夕を虹門より約
３弧の深部へ投与した。The method of administration into the rectum is approximately 2 kg after fasting for 2 hours.
Using a small syringe, one dose was administered into the rectum of a male domestic rabbit approximately 3 arcs deep from the rainbow gate.
血糖は経時的に耳静脈より採血し酵素法〔Ｓｃｈｍｉｄ
ｔ Ｆ．日．ｌｎｔｅｍｉｓＬ ４ ５５４（１９６３
）〕によって測定した。上記方法で投与前の血糖を測定
し、これを１００％として経時的な血糖の変化率を求め
その結果を表１に示す。表 １ 家兎の血糖に対する
インシュリン投与の影響注１．投与前の血糖を１００落
として十は皿糖上昇、−は血糖低下を示す。Blood sugar was measured over time by collecting blood from the ear vein and using the enzymatic method [Schmid
tF. Day. lntemis L 4 554 (1963
)]. The blood sugar level before administration was measured using the above method, and the rate of change in blood sugar level over time was determined by setting this value as 100%, and the results are shown in Table 1. Table 1 Effect of insulin administration on blood sugar in domestic rabbits Note 1. The pre-administration blood sugar level was lowered by 100, 10 indicates an increase in plate sugar, and - indicates a decrease in blood sugar.
注２．家兎の投与前の血糖は１２１．３士９．０物／ｄ
ｌである。注３．インシュリンは２４〃イ物を４弱用し
た。注４．変化率は家兎５匹の平均値である。注５．
５０／ｋタウサギｋｇ当りのインシュリン投与量。Note 2. The blood sugar level of the rabbit before administration was 121.3 to 9.0/d.
It is l. Note 3. I used just under 4 of 24 types of insulin. Note 4. The rate of change is the average value of 5 domestic rabbits. Note 5.
50/k insulin dose per kg of rabbit.
本発明で用いられるインシュリンは、ウシ、ブタ、クジ
ラのインシュリンなど非経口的投与によって血糠低下作
用を有するインシュリンであれば何でもよく、例えばイ
ンシュリンの亜鉛母匿体のような金属との鍵体あるいは
プロタミン亜鉛インシュリンやグロビンィンシュリンな
ども使用に適していることは勿論である。又、本発明で
使用するハロゲン化アルキルトリメチルアンモニウムと
しては、塩化オクチルトリメチルアンモニウム、塩化デ
シルトリメチルアンモニウム、塩化ラウリルトリメチル
アンモニウム、塩化パルミチルトリメチルアンモニウム
、塩化ステアリルトリメチルアンモニウム、臭化オクチ
ルトリメチルアンモニウム、臭化ラウリルトリメチルア
ンモニウム、臭化ミリスチルトリメチルアンモニウム等
のハロゲン化中級乃至高級アルキル（Ｃ８一Ｃ，８）ト
リメチルアンモニウムが用いられる。本発明のインシュ
リンの直腸投与用整剤を製造するための基剤としては、
油性基剤または水性基剤が適している。The insulin used in the present invention may be any insulin that has a blood clot-lowering effect when administered parenterally, such as bovine, porcine, or whale insulin. Of course, protamine zinc insulin and globin insulin are also suitable for use. Further, the halogenated alkyltrimethylammonium used in the present invention includes octyltrimethylammonium chloride, decyltrimethylammonium chloride, lauryltrimethylammonium chloride, palmityltrimethylammonium chloride, stearyltrimethylammonium chloride, octyltrimethylammonium bromide, and lauryl bromide. A halogenated intermediate to higher alkyl (C81C,8) trimethylammonium such as trimethylammonium and myristyltrimethylammonium bromide is used. The base for producing the preparation for rectal administration of insulin of the present invention includes:
Oily or aqueous bases are suitable.
油性基剤としてはラッカセイ油、ャシ油、オリーブ油、
大豆油、ナタネ油、メンジツ油、ゴマ油、トウモロコシ
油、ヌカ油、ツバキ油、カカオ脂、豚脂、羊毛脂、牛脂
等、又これらを水素添加、アセチル化、分割抽出等によ
り改質したもの、炭素数６〜３０の脂肪酸とグリセロー
ルのェステル（例ダイナマイトノーベル社製：ウイテプ
ゾル■，日清製油ＫＫ製ＯＤＯ−１■），炭素数６〜３
０の脂肪酸と炭素数２〜８のアルコールとのェステル（
例、ィソプロピルミリステート日光ケミカルズ社製：ニ
ッコールＩＰＭ■）等が挙げられこれらの油性基剤は単
独又は二種以上混合してもよい。水落性基剤としてはた
とえばポリエチレングリコール（局方名マクロゴール）
、プロピレングリコール、グリセロゼラチン等が挙げら
れ、そしてこれらの水落性基剤も単独又は二種以上混合
して使用することができる。Oily bases include peanut oil, coconut oil, olive oil,
Soybean oil, rapeseed oil, menjitsu oil, sesame oil, corn oil, bran oil, camellia oil, cacao fat, lard, wool fat, beef tallow, etc., and those modified by hydrogenation, acetylation, split extraction, etc. Ester of fatty acid and glycerol having 6 to 30 carbon atoms (e.g. Dynamite Nobel: Uitepsol ■, Nisshin Oil Co., Ltd. ODO-1■), carbon number 6 to 3
Esters of 0 fatty acids and alcohols with 2 to 8 carbon atoms (
Examples include isopropyl myristate Nikkor IPM (manufactured by Nikko Chemicals), and these oil bases may be used alone or in combination of two or more. Examples of water-removalable bases include polyethylene glycol (pharmacopoeia name: macrogol)
, propylene glycol, glycerogelatin, etc., and these water-dropping bases can be used alone or in combination of two or more.
尚、このほかの基剤として水を使用してもよく、その場
合前記油性又は水溶性基材と混合してもよい。前記のハ
ロゲン化、アルキルトリメチルアンモニウムの添加塁は
基剤に対し０．１％〜２０％（重量）で好ましくは０．
５〜１０％（重量）であり、インシュリンの添加量は添
加剤および基剤総量の単位重量（グラム）当たり、２〜
２００単位、好ましくは５〜１５山単位である。In addition, water may be used as another base material, and in that case, it may be mixed with the oil-based or water-soluble base material. The amount of the halogenated alkyltrimethylammonium added is 0.1% to 20% (by weight) based on the base material, preferably 0.1% to 20% (by weight).
The amount of insulin added is 2 to 10% (by weight) per unit weight (gram) of the total amount of additive and base material.
The number is 200 units, preferably 5 to 15 units.
なお、本発明で得られた製剤に更に安定化剤、防腐剤等
を加えてもよい。In addition, a stabilizer, a preservative, etc. may be further added to the preparation obtained in the present invention.
直腸投与の剤型としては常温で固体で体温で溶解する虹
門坐剤の型でも良く又液状の油脂に分散させた軟膏状あ
るいは液状のものを例えば直腸投与ソフトカプセル、直
腸投与用注入器等を用いて投与する剤型等にしてもよい
。本発明を実施するには前述の基剤および添加剤を混合
溶剤あるいは混合溶融後これらにインシュリンを均等に
分散すればよく、それ自体公３句の軟膏坐剤等の製法に
準じ成型して調製することができる。The dosage form for rectal administration may be a Hongmen suppository, which is solid at room temperature and dissolves at body temperature, or an ointment or liquid form dispersed in liquid oil, such as a soft capsule for rectal administration, a syringe for rectal administration, etc. It may also be made into a dosage form for administration. To carry out the present invention, the above-mentioned base and additives may be mixed in a solvent or mixed and melted, and then insulin may be evenly dispersed therein, which itself can be prepared by molding in accordance with the manufacturing method for ointment suppositories, etc. can do.
次に本発明の組成物の製造例を示す。Next, a manufacturing example of the composition of the present invention will be shown.
実施例 １
トウモロコシ油１４５．５のこ塩化ステアリルトリメチ
ルアンモニウム４．５夕及びインシュリン５０００単位
を添加し、よくかきまぜ分散させたのち、１．５夕あて
直腸投与用注入器に分注する。Example 1 145.5 units of corn oil, 4.5 units of stearyltrimethylammonium chloride, and 5000 units of insulin were added, stirred well to disperse, and then dispensed into a syringe for rectal administration for 1.5 hours.
実施例 ２トウモロコシ油１４５．５のこ塩化ステアリ
ルトリメチルアンモニウム４．５夕，次いでインシュリ
ン８００山単位を添加し、よくかきまぜ分散させたのち
１．５夕あて直腸投与用注入器に分注する。Example 2 145.5 ml of corn oil, 4.5 ml of stearyltrimethylammonium chloride, and 800 munits of insulin were then added, stirred well to disperse, and dispensed into a syringe for rectal administration after 1.5 ml.
Claims (1)
モニウムを混和させることを特徴とするインシユリン直
腸投与用組成物。1. A composition for rectal administration of insulin, which comprises mixing insulin with alkyltrimethylammonium halide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51092131A JPS603043B2 (en) | 1976-08-02 | 1976-08-02 | Composition for rectal administration of insulin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51092131A JPS603043B2 (en) | 1976-08-02 | 1976-08-02 | Composition for rectal administration of insulin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5318723A JPS5318723A (en) | 1978-02-21 |
| JPS603043B2 true JPS603043B2 (en) | 1985-01-25 |
Family
ID=14045867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51092131A Expired JPS603043B2 (en) | 1976-08-02 | 1976-08-02 | Composition for rectal administration of insulin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS603043B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2552764B2 (en) * | 1991-02-04 | 1996-11-13 | ミサワホーム株式会社 | Roof unit |
-
1976
- 1976-08-02 JP JP51092131A patent/JPS603043B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5318723A (en) | 1978-02-21 |
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