JPH0134205B2 - - Google Patents
Info
- Publication number
- JPH0134205B2 JPH0134205B2 JP56155731A JP15573181A JPH0134205B2 JP H0134205 B2 JPH0134205 B2 JP H0134205B2 JP 56155731 A JP56155731 A JP 56155731A JP 15573181 A JP15573181 A JP 15573181A JP H0134205 B2 JPH0134205 B2 JP H0134205B2
- Authority
- JP
- Japan
- Prior art keywords
- saponin
- absorption
- saponins
- minutes
- orally administered
- 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
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 150000008130 triterpenoid saponins Chemical class 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 2
- 239000002132 β-lactam antibiotic Substances 0.000 claims 1
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 1
- 229930182490 saponin Natural products 0.000 description 11
- 150000007949 saponins Chemical class 0.000 description 11
- 235000017709 saponins Nutrition 0.000 description 11
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- SMRPGWBDLOQHOS-UHFFFAOYSA-N 5-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-3,4-dihydroxy-6-[[9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]oxane-2-carboxylic acid Chemical compound OC1C(O)C(O)C(C)OC1OC1C(OC2C(OC(C(O)C2O)C(O)=O)OC2C(C3C(C4C(C5(CCC6(C)C(O)CC(C)(C)CC6C5=CC4=O)C)(C)CC3)(C)CC2)(C)CO)OC(CO)C(O)C1O SMRPGWBDLOQHOS-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- BMWPBKOFJSHJAW-UHFFFAOYSA-N Saponin B Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(OC6OC(CO)C(O)C(OC7OC(CO)C(O)C(O)C7O)C6=O)C(C)(C)C5CCC34C)C2C1)C(=O)O BMWPBKOFJSHJAW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- PPRSVUXPYPBULA-UHFFFAOYSA-N saponin A Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(OC6OC(CO)C(O)C(O)C6=O)C(C)(C)C5CCC34C)C2C1)C(=O)O PPRSVUXPYPBULA-UHFFFAOYSA-N 0.000 description 3
- 241000208340 Araliaceae Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 description 2
- 241000580938 Sapindus Species 0.000 description 2
- KLOHDWPABZXLGI-YWUHCJSESA-M ampicillin sodium Chemical compound [Na+].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 KLOHDWPABZXLGI-YWUHCJSESA-M 0.000 description 2
- 229960001931 ampicillin sodium Drugs 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 235000008434 ginseng Nutrition 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LVTJOONKWUXEFR-UEZXSUPNSA-N protodioscin Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@@H]5O[C@]([C@H]([C@@H]5[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1)C)(O)CC[C@@H](C)CO[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O LVTJOONKWUXEFR-UEZXSUPNSA-N 0.000 description 2
- QDQWGYLCDZBAMD-UHFFFAOYSA-N saponin C Natural products CC1C2C3CCC4C5(C)CCC(O)C(C)(COC6OC(CO)C(O)C(O)C6O)C5CCC4(C)C3(C)CCC27C8OC8C1(C)OC7=O QDQWGYLCDZBAMD-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NTWLPZMPTFQYQI-UHFFFAOYSA-N (3alpha)-olean-12-ene-3,23-diol Natural products C1CC(O)C(C)(CO)C2CCC3(C)C4(C)CCC5(C)CCC(C)(C)CC5C4=CCC3C21C NTWLPZMPTFQYQI-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000722953 Akebia Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 241000230612 Caulophyllum robustum Species 0.000 description 1
- 241000202567 Fatsia japonica Species 0.000 description 1
- 229930183217 Genin Natural products 0.000 description 1
- 240000004670 Glycyrrhiza echinata Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- GCGBHJLBFAPRDB-UHFFFAOYSA-N Hederagenin Natural products CC1(C)CCC2(CCC3(C)C4CCC5C(C)(CO)C(O)CCC5(C)C4CC=C3C2C1)C(=O)O GCGBHJLBFAPRDB-UHFFFAOYSA-N 0.000 description 1
- 241001190114 Lecaniodiscus cupanioides Species 0.000 description 1
- 108091005461 Nucleic proteins Proteins 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- GCGBHJLBFAPRDB-KCVAUKQGSA-N Scutellaric acid Natural products CC1(C)CC[C@@]2(CC[C@@]3(C)[C@@H]4CC[C@H]5[C@@](C)(CO)[C@H](O)CC[C@]5(C)[C@H]4CC=C3[C@@H]2C1)C(=O)O GCGBHJLBFAPRDB-KCVAUKQGSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 210000000990 duodenal loop Anatomy 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- PGOYMURMZNDHNS-MYPRUECHSA-N hederagenin Chemical compound C1C[C@H](O)[C@@](C)(CO)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C PGOYMURMZNDHNS-MYPRUECHSA-N 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 description 1
- 229940048730 senega Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000005856 steroid saponins Chemical class 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Description
〔〕 発明の背景
技術分野
本発明は、トリテルペノイドサポニンを有効成
分とする経口投与用薬物吸収補助剤に関する。こ
のトリテルペノイドサポニンはムクロジ
（Sapindus mukurossi Gaerth.）の果皮（以下エ
ンメイヒという）より抽出、単離することができ
る。
先行技術
サポニンは、その精製単離の困難性と構造の複
雑性のために、研究の進展を見せたのはここ十数
年のことである。
サポニンの特性は、水溶液中の起泡性と赤血球
破壊作用（溶血活性）、魚毒性、コレステロール
（ステロイド類）とのコンプレツクス形成能で代
表されるが、医薬品としては、去痰、鎮咳、抗炎
症、中枢抑制、抗疲労、抗潰瘍、コレステロール
代謝促進、脂質代謝の促進、核酸、タンパクの合
成促進の他に感染防御、抗腫瘍などの薬理作用が
近年見出だされている。サポニン含量が比較的高
く、今なお日本薬局方に収載されているサポニン
含有生薬は、セネガ、オンジ、キキヨウ、カンゾ
ウ、ゴシツ、サイコ、チクセツニンジン、ニンジ
ン、バクモンドウ、モクツウなどある。
サポニンは、そのサポゲニン部分の化学構造に
より、ステロイドサポニンおよびトリテルペノイ
ドサポニンに分類される。トリテルペノイドサポ
ニンの一つであるエンメイヒサポニンは、従来医
療用としては使用されていなかつたが、化学構造
の類似性からその抗炎症作用が検討され、ラツト
のカラゲニン浮腫、アジユバント開節炎において
抑制効果を示したという報告がある。
以上のようなサポニンについての様々な薬理作
用が発見されているが、本格的な薬理学的研究は
始まつたばかりで、今後も従来の医薬品には見ら
れない新しい薬理作用が発見される可能性を秘め
ている。
またヘデラゲニンをゲニンとするトリテルペノ
イドサポニンは、例えば、アケビ（Akebia
guinata Decne.）（Chem.Pharm.Bull.24，1021
（1976））、ルイヨウボタン（Caulophyllum
robustum Maxim.）（C.A.85，106644h（1976））、
ヤツデ（Fatsia japonica Decne.）
（Phytochemistry 15，781（1976））、ムクロジ
（Sapindus mukurossi Gaertn.）（C.A.73，
77544，110062m，110071p（1970）及びC.A.74，
13384f（1971））、Lecaniodiscus cupanioides
Planch.ex Benth.（Phytochemistry 20，1939
（1981））などの植物から種々得られているが、や
はりその本格的な薬理学的研究は進んでいない。
一方、抗菌製剤の投与においては、最低有効血
中濃度が知られており、これ以下の薬物血中濃度
では、薬物が体内にどれほど長時間存在しても有
効ではない。その為に、経口投与の場合の薬物の
吸収利用率は非常に重要であり、従来、薬物の吸
収効率を高めてより少量の薬物で有効血中濃度を
維持できる方法が、製剤的見地から、あるいは投
与法などから検討されてきた。
しかし、通常の経口投与剤を通常の経口投与で
投与して吸収利用率を高めることができれば裨益
するところは大きい。
最近、本発明者は、サポニン成分含有生薬抽出
物が、薬理活性物質の吸収促進効果を有すること
を発見したが（特開昭57−145816号公報）、具体
的な化合物を提示するには至つていなかつた。
したがつて、このような作用を有する具体的な
化合物が提示できれば、将来、製剤的見地、安全
性、薬理学的見地あるいは品質管理的見地などか
らみて、裨益するところは大きい。
〔〕 発明の概要
本発明は上記の点に解決を与えることを目的と
し、吸収補助剤として特定の化合物を提示するこ
とによつてこの目的を達成しようとするものであ
る。
したがつて、本発明による経口投与されたβ―
ラクタム型抗生物質の吸収を補助するための経口
投与用薬物吸収補助剤は、下式で示されるトリテ
ルペノイドサポニンを有効成分とすること、を特
徴とするものである。
〔〕 発明の具体的説明
１ サポニン
本発明で利用するサポニンは、前記一般式中の
基Ｒの種類によつて、サポニンＡ、ＢおよびＣの
三種である。
[] BACKGROUND TECHNICAL FIELD OF THE INVENTION The present invention relates to an orally administered drug absorption aid containing triterpenoid saponin as an active ingredient. This triterpenoid saponin can be extracted and isolated from the pericarp (hereinafter referred to as Enmeihi) of Sapindus mukurossi Gaerth. PRIOR ART Saponins have only made progress in research over the past decade due to the difficulty in purifying and isolating them and the complexity of their structures. The characteristics of saponin are represented by foaming properties in aqueous solutions, red blood cell destruction activity (hemolytic activity), toxicity to fish, and ability to form complexes with cholesterol (steroids). In addition to central depression, anti-fatigue, anti-ulcer, promotion of cholesterol metabolism, promotion of lipid metabolism, promotion of synthesis of nucleic acids and proteins, pharmacological effects such as infection prevention and antitumor activities have been discovered in recent years. Saponin-containing herbal medicines that have a relatively high saponin content and are still listed in the Japanese Pharmacopoeia include senega, onji, kikiyo, licorice, goshitsu, saiko, chikusetsu ginseng, ginseng, bakumondo, and mokutsu. Saponins are classified into steroid saponins and triterpenoid saponins depending on the chemical structure of their sapogenin moieties. Enmeihi saponin, one of the triterpenoid saponins, had not been used for medical purposes until now, but its anti-inflammatory effect was investigated due to the similarity of its chemical structure, and it was found to have a suppressive effect on carrageenin edema and adjuvant ostitis in rats. There are reports that it showed. Various pharmacological effects of saponins have been discovered as described above, but full-scale pharmacological research has just begun, and there is a possibility that new pharmacological effects not found in conventional drugs will be discovered in the future. is hidden. In addition, triterpenoid saponins containing hederagenin as genin include, for example, Akebia
guinata Decne.) (Chem.Pharm.Bull. 24 , 1021
(1976)), Caulophyllum
robustum Maxim.) (CA 85 , 106644h (1976)),
Fatsia japonica Decne.
(Phytochemistry 15 , 781 (1976)), Sapindus mukurossi Gaertn. (CA 73 ,
77544, 110062m, 110071p (1970) and CA 74 ,
13384f (1971)), Lecaniodiscus cupanioides
Planch.ex Benth. (Phytochemistry 20 , 1939
(1981)), but full-scale pharmacological research has not yet progressed. On the other hand, in the administration of antibacterial preparations, a minimum effective blood concentration is known, and drug blood concentrations below this are not effective no matter how long the drug remains in the body. For this reason, the absorption and utilization rate of drugs during oral administration is extremely important, and from a pharmaceutical standpoint, conventional methods that increase drug absorption efficiency and maintain effective blood concentrations with smaller amounts of drugs are Alternatively, consideration has been given to the method of administration. However, there would be great benefits if the absorption and utilization rate could be increased by administering a conventional oral drug through conventional oral administration. Recently, the present inventor discovered that a herbal medicine extract containing saponin components has the effect of promoting the absorption of pharmacologically active substances (Japanese Patent Application Laid-open No. 145816/1983), but it has not yet been possible to present a specific compound. I wasn't there. Therefore, if a specific compound having such an action could be presented, it would be of great benefit in the future from a pharmaceutical standpoint, safety, pharmacological standpoint, or quality control standpoint. [] SUMMARY OF THE INVENTION The present invention aims to provide a solution to the above points and attempts to achieve this aim by presenting specific compounds as absorption aids. Therefore, the orally administered β-
An orally administered drug absorption adjuvant for assisting absorption of lactam antibiotics is characterized by containing a triterpenoid saponin represented by the following formula as an active ingredient. [] Detailed Description of the Invention 1 Saponin The saponins used in the present invention are of three types, saponins A, B and C, depending on the type of group R in the above general formula.
ラツト（体重180〜220ｇ）をペントバルビター
ルナトリウム（30mg／Kg）で麻酔し、39℃の恒温
水を循環させた金属製ウオーターベツド上に仰臥
固定する。常法により胃幽門部下１cmを始点とし
て長さ10cmの十二指腸ループを作製する。このル
ープ内に、アンピシリンナトリウムおよびサポニ
ンＡまたはサポニンＢまたはサポニンＣを溶解し
たPH6.5リン酸緩衝液をラツト体重200ｇあたり
0.5mlの割合で注入する。注入直後から10分、20
分、40分、60分、90分、120分、および180分に頚
静脈より採血し、生物学的検定法によつて活性濃
度を測定した。
すなわち、日本抗生物質医薬品基準に準拠し
て、検定菌としてはバチルス・スブチリス（B.
subtilis）を用い、ペーパーデイスク法で37℃／
15〜20時間培養、検定した。
投与溶液組成は次の通りである。
アンピシリンナトリウム 20mg／ml
サポニンＡまたはＢまたはＣ ５mg／ml
上記実験方法による実施例を実施例１〜３に示
した。なお、いずれの場合にも、実験で用いた十
二脂腸の肉眼による観察によれば、粘膜の損傷
（たとえば粘膜剥離）あるいは出血斑等の異常は
みられなかつた。
〔実施例 １〕
サポニンＡを用いた結果を表１に示した。
〔実施例 ２〕
サポニンＢを用いた結果を表２に示した。
〔実施例 ３〕
サポニンＣを用いた結果を表３に示した。
Rats (weighing 180-220 g) are anesthetized with pentobarbital sodium (30 mg/Kg) and fixed supine on a metal waterbed in which constant-temperature water at 39°C is circulated. A duodenal loop with a length of 10 cm is created using a standard method starting from 1 cm below the stomach pylorus. In this loop, a PH6.5 phosphate buffer solution containing ampicillin sodium and saponin A, saponin B, or saponin C was added per 200 g of rat body weight.
Inject at a rate of 0.5 ml. 10 minutes, 20 minutes immediately after injection
Blood was collected from the jugular vein at minutes, 40 minutes, 60 minutes, 90 minutes, 120 minutes, and 180 minutes, and the active concentration was measured by a biological assay. In other words, in accordance with the Japanese Antibiotic Drug Standards, Bacillus subtilis (B.
subtilis) using the paper disc method at 37℃/
The cells were cultured and assayed for 15 to 20 hours. The composition of the administration solution is as follows. Ampicillin sodium 20 mg/ml Saponin A or B or C 5 mg/ml Examples 1 to 3 show examples based on the above experimental method. In any case, macroscopic observation of the duodenal intestine used in the experiment revealed no abnormalities such as damage to the mucous membrane (for example, mucosal detachment) or bleeding spots. [Example 1] Table 1 shows the results using saponin A. [Example 2] Table 2 shows the results using saponin B. [Example 3] Table 3 shows the results using saponin C.
【表】【table】
【表】【table】
Claims (1)
有効成分とすることを特徴とする、経口投与され
たβ―ラクタム型抗生物質の吸収を補助するため
の経口投与用薬物吸収補助剤。 [Scope of Claims] 1. An orally administered drug absorption adjuvant for assisting the absorption of an orally administered β-lactam antibiotic, which is characterized by containing a triterpenoid saponin represented by the following formula as an active ingredient.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56155731A JPS5857400A (en) | 1981-09-30 | 1981-09-30 | Adjuvant for drug absorption and its preparation |
| US06/354,289 US4501734A (en) | 1981-03-06 | 1982-03-03 | Promotion of absorption of drugs administered through the alimentary system |
| DE19823207841 DE3207841A1 (en) | 1981-03-06 | 1982-03-04 | ADJUVANS PREPARATION |
| CH1350/82A CH652931A5 (en) | 1981-03-06 | 1982-03-05 | ADJUVANT COMPOSITION FOR ASSISTING THE ABSORPTION OF A PHARMACOLOGICALLY ACTIVE SUBSTANCE, ADMINISTERED VIA THE DIGESTIVE APPARATUS. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56155731A JPS5857400A (en) | 1981-09-30 | 1981-09-30 | Adjuvant for drug absorption and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5857400A JPS5857400A (en) | 1983-04-05 |
| JPH0134205B2 true JPH0134205B2 (en) | 1989-07-18 |
Family
ID=15612215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56155731A Granted JPS5857400A (en) | 1981-03-06 | 1981-09-30 | Adjuvant for drug absorption and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5857400A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103007280B (en) * | 2013-01-18 | 2014-02-19 | 辽宁益康生物股份有限公司 | Piglet colibacillosis lyophilized serum immunoglobulin preparation and preparation process thereof |
| CN103041388B (en) * | 2013-01-18 | 2014-02-19 | 辽宁益康生物股份有限公司 | Piglet colibacillosis egg yolk immunoglobulin biological preparation and preparation process thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146615A (en) * | 1977-01-20 | 1979-03-27 | Laboratoires Sarget | Chrysanthellum plant extract |
-
1981
- 1981-09-30 JP JP56155731A patent/JPS5857400A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146615A (en) * | 1977-01-20 | 1979-03-27 | Laboratoires Sarget | Chrysanthellum plant extract |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5857400A (en) | 1983-04-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU686656B2 (en) | Compositions containing piperine | |
| EP1022022B1 (en) | Composition for inhibiting increase of blood sugar level or lowering blood sugar level | |
| US8586569B2 (en) | Betulonic and betulinic acid derivatives | |
| WO2006056129A1 (en) | Compositions of huperzia serrata alkaloids comprising huperzine a and huperzine b and preparation thereof | |
| CN101541317B (en) | Transmucosal administration of 2,3-dimethoxy-5-methyl-6-(10- hydroxydecy l)-1,4-benzoquinone | |
| WO2009067891A1 (en) | Water-soluble triterpenephenol compounds having antitumor activity and the preparation thereof | |
| JP2003531813A (en) | Naphthoquinone derivatives and their use in the treatment and control of tuberculosis | |
| EP1001799A1 (en) | Pharmaceutical composition containing peptichemio | |
| JPH0134205B2 (en) | ||
| JPS6041656A (en) | Manufacture of novel aminoacid derivative | |
| KR20030023232A (en) | Method of extracting saponin from Panax ginseng or Gynostemma pentaphyllum and foods containing the extracted saponin therefrom | |
| JP3949198B2 (en) | V-ATPase uncoupled H + pump inhibitor | |
| KR101082802B1 (en) | Pharmaceutical composition for preventing or treating premature ejaculation comprising 8-hydroxyclomipramine or its salt | |
| KR100564383B1 (en) | Process for preparing ginsenoside derivatives | |
| JPH0678231B2 (en) | Blood viscosity reducing agent | |
| KR100547253B1 (en) | Treating and prevention of cancer with new ginsenoside derivatives | |
| CN111647036A (en) | Ocotillol esterified derivatives, preparation method thereof and application thereof in preparing anti-inflammatory drugs | |
| JPH09241157A (en) | Medicinal composition for protecting liver containing lithospermate b | |
| US4436732A (en) | Medicated compound for treating diseases infected by virus of the herpes group | |
| JP2631688B2 (en) | Pharmaceuticals composed of glycyrrhetinic acid derivatives | |
| JPH0753385A (en) | Alcohol absorption inhibitor | |
| US8557784B2 (en) | Glycyrrhizinates of morphinan derivatives | |
| KR20060086781A (en) | Ginsenoside derivatives and the uses of them | |
| JPS609023B2 (en) | Indirubin derivatives and antitumor agents containing them | |
| JPS6215529B2 (en) |