JPS6314719A - Guaiazulenesulfonate preparation - Google Patents
Guaiazulenesulfonate preparationInfo
- Publication number
- JPS6314719A JPS6314719A JP16065286A JP16065286A JPS6314719A JP S6314719 A JPS6314719 A JP S6314719A JP 16065286 A JP16065286 A JP 16065286A JP 16065286 A JP16065286 A JP 16065286A JP S6314719 A JPS6314719 A JP S6314719A
- Authority
- JP
- Japan
- Prior art keywords
- glutamine
- guaiazulenesulfonate
- diclofenac
- nitrazepam
- salt
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- VIZXMHCBZLGUET-UHFFFAOYSA-N sodium gualenate Chemical compound CC(C)C1=CC=C(C)C2=C(S(O)(=O)=O)C=C(C)C2=C1 VIZXMHCBZLGUET-UHFFFAOYSA-N 0.000 title abstract description 5
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims abstract description 12
- KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229960001454 nitrazepam Drugs 0.000 claims abstract description 8
- 229960001259 diclofenac Drugs 0.000 claims abstract description 7
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- HTJXMOGUGMSZOG-UHFFFAOYSA-N tiaramide Chemical compound C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 HTJXMOGUGMSZOG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229950010302 tiaramide Drugs 0.000 claims abstract description 6
- 229960002743 glutamine Drugs 0.000 claims abstract description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 239000008280 blood Substances 0.000 abstract description 7
- 210000004369 blood Anatomy 0.000 abstract description 7
- 229930182816 L-glutamine Natural products 0.000 abstract description 5
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 3
- 159000000000 sodium salts Chemical class 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 210000004880 lymph fluid Anatomy 0.000 description 6
- -1 alkali metal salt Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- UKNGDQSYPNBJAO-UHFFFAOYSA-N Tiaramide hydrochloride Chemical compound Cl.C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 UKNGDQSYPNBJAO-UHFFFAOYSA-N 0.000 description 4
- 210000002751 lymph Anatomy 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 229940000425 combination drug Drugs 0.000 description 3
- 229960001193 diclofenac sodium Drugs 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920000669 heparin Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 210000001268 chyle Anatomy 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 210000002796 renal vein Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 241000208838 Asteraceae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- XQQWBPOEMYKKBY-UHFFFAOYSA-H trimagnesium;dicarbonate;dihydroxide Chemical compound [OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[O-]C([O-])=O.[O-]C([O-])=O XQQWBPOEMYKKBY-UHFFFAOYSA-H 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
（発明の目的）
本発明はグアヤズレンスルホン酸塩にグルタミン、ジク
ロフェナック、チアラミド若くはニトラゼパム又はそれ
らの塩類を配合した製剤に関するもので、その目的はグ
アヤズレンスルホン酸塩の血中濃度を上記薬物の配合に
よって上昇させ吸収促進を招来させる点にある。Detailed Description of the Invention (Object of the Invention) The present invention relates to a preparation containing guayazulene sulfonate and glutamine, diclofenac, thiaramide or nitrazepam or their salts; The point is that the concentration of salt in the blood is increased by the combination of the above-mentioned drugs, leading to promotion of absorption.
グアヤズレンスルホン酸塩、なかんず（グアヤグレン−
３−スルホン酸は次の化学構造式で表される。Guayadulene sulfonate, among other things (guayagrain)
3-sulfonic acid is represented by the following chemical structural formula.
ただし式中、Ｘは一価の陽イオンを表わし好ましくはア
ルカリ金属、特にナトリウムである。このものはヨーロ
ッパ原産のキク科植物のカミツレＭａｔｒｉｃａｒｉａ
ｃｈａｍｏｍｉ−１１ａの有効成分であるアズレンの
スルホン化によって得られ、種々の有用な薬理作用（た
とえば抗炎症作用、ヒスタミン遊離抑制作用、抗潰瘍作
用など）を有するため、抗炎症剤や抗潰瘍剤として臨床
上ひろく使用されている。However, in the formula, X represents a monovalent cation and is preferably an alkali metal, particularly sodium. This is Chamomile Matricaria, a plant of the Asteraceae family native to Europe.
It is obtained by sulfonation of azulene, which is the active ingredient of chamomi-11a, and has various useful pharmacological effects (e.g., anti-inflammatory effect, histamine release inhibitory effect, anti-ulcer effect, etc.), so it is used as an anti-inflammatory agent and anti-ulcer agent. Widely used clinically.
しかしながら本品をラットに経口投与した実験によれば
本品の消化管からの吸収は極めて遅く、最高血中濃度に
達するには数時間を要し、従って迅速な血中濃度上昇が
期待される臨床領域においては必ずしも満足すべき結果
を与えず、この点に関する改良が待望されていた。However, according to experiments in which this product was orally administered to rats, the absorption of this product from the gastrointestinal tract was extremely slow, and it took several hours to reach the maximum blood concentration, so a rapid increase in blood concentration was expected. In the clinical field, these methods do not necessarily give satisfactory results, and improvements in this regard have been long awaited.
（発明の構成）
本発明は前記欠点の改良について鋭意研究を重ねたとこ
ろ、グルタミン、ジクロフェナック、チアラミド若くは
ニトラゼバム又はそれらの塩を配合すると、全く予期し
なかったことに本品の吸収が促進され迅速な血中濃度上
昇が期待できることを発見し、本発明を完成した。(Structure of the Invention) As a result of extensive research into improving the above-mentioned drawbacks, the present invention found that when glutamine, diclofenac, thiaramide, nitrazebam, or their salts were blended, the absorption of the product was unexpectedly promoted. The present invention was completed based on the discovery that a rapid increase in blood concentration can be expected.
本発明の要旨は特許請求の範囲に記載の通りであって、
グアヤズレンスルホン酸塩としては既に述べたようにグ
アヤズレンー３−スルホン酸の、好ましくはアルカリ金
属塩、特にナトリウム塩が用いられる。The gist of the present invention is as described in the claims,
As the guaiazulene sulfonate salt, preferably the alkali metal salt, especially the sodium salt, of guaiazulene-3-sulfonic acid is used, as already mentioned.
配合物のうち、グルタミンはＬ−グルタミンが好ましい
。ジクロフェナックはそのナトリウム塩が、そしてチア
ラミドは塩酸塩が好ましい。むろんこれらは単なる例示
であり、決して本発明を限定するものではない。In the formulation, the glutamine is preferably L-glutamine. Diclofenac is preferably its sodium salt, and thiaramide is preferably its hydrochloride. Of course, these are merely examples and do not limit the invention in any way.
（発明の効果） 本発明の効果は次の実験によって確認した。(Effect of the invention) The effects of the present invention were confirmed by the following experiment.
まず実験動物としては、２４時間絶食させた体重２．０
〜２．３ｋｇの白色雄性家兎（Ｋｅａｒｉ、大阪）を用
い、かつ一群５羽を用いた。First, as an experimental animal, the body weight was 2.0 after fasting for 24 hours.
~2.3 kg white male domestic rabbits (Keari, Osaka) were used, and 5 rabbits were used per group.
薬物の投与に際してはグアヤグレン−３−スルホン酸ナ
トリウム（以下ＧＡＳと略す）（９南化工製）５０■を
蒸溜水１０ｍ１に熔解し、該溶液をネラトン・カテーテ
ル（Ｎｏ、７）を用いて経口投与し、なお溶液がカテー
テル内に残らぬよう蒸溜水５ｍｌで洗い流した。When administering the drug, dissolve 50 ml of sodium guayagrain-3-sulfonate (hereinafter abbreviated as GAS) (manufactured by 9 Minami Kako) in 10 ml of distilled water, and administer the solution orally using a Nelaton catheter (No. 7). However, the catheter was rinsed with 5 ml of distilled water so that no solution remained in the catheter.
配合物併用の場合は、ＧＡ３５０■に対してＬ−グルタ
ミンは５０■、ジクロフェナック・ナトリウムは２５■
、チアラミド塩酸塩５０■及びニトラゼパム５■をそれ
ぞれ上記の溶液に添加して経口投与した。When using combinations, L-glutamine is 50■ and diclofenac sodium is 25■ against GA350■.
, 50 μl of tiaramide hydrochloride, and 5 μl of nitrazepam were added to the above solution and administered orally.
これらの溶液の経口投与後の血漿液中及びリンパ液中の
ＧＡＳ濃度を経時的に測定した。なお、血漿及びリンパ
液の採取法、ならびにそれらの中のＧＡＳの定量法を以
下に説明する。After oral administration of these solutions, GAS concentrations in plasma and lymph were measured over time. In addition, the method for collecting plasma and lymph fluid and the method for quantifying GAS therein will be explained below.
血グｎの採取は、家兎を固定器に部位に固定し、エーテ
ル麻酔下、ヘパリン処理したＴ字型カテーテルを家兎頚
動脈に挿入し、あらかじめ１０％ヘパリンナトリウム溶
液で処理した試験管に移し、３０００ｒｐｍで５分間遠
心分離を行って目的とする血漿を採取した。この０．５
１を定量に用いる。Blood samples were collected by fixing the rabbit in place using a fixator, inserting a heparin-treated T-shaped catheter into the rabbit's carotid artery under ether anesthesia, and transferring it to a test tube pretreated with 10% sodium heparin solution. The target plasma was collected by centrifugation at 3000 rpm for 5 minutes. This 0.5
1 is used for quantitative determination.
リンパ液の採取はＢｏｌ Ｉｍａｎらの方法に準じて行
った。Lymph fluid was collected according to the method of Bol Iman et al.
すなわち家兎をエーテル麻酔下で開腹後、腹大静脈と腎
静脈の合流点付近でビンセットを用いて静かに剥離し、
乳ビ槽を露出させた。腹側部に穴をあけ、あらかじめヘ
パリンで処理したポリエチレンチューブ（外径：１ｍｍ
）を体内に誘導したのち、その先端を乳ビ槽に挿入し、
挿入部位にアロンアルファ（登録商標）を滴下してリン
パ液の漏出を防止した。またポリエチレンチューブが外
れないようにそれ自体もアロンアルファで固定した。次
いでポリエチレンチューブからリンパ液を採取しその０
．５ｍｌを定量に用いる。That is, after the rabbit's abdomen was opened under ether anesthesia, the abdominal vena cava and renal vein were gently dissected using a vinset near the confluence of the renal vein.
The chyle tank was exposed. A polyethylene tube (outer diameter: 1 mm) was prepared with a hole in the ventral part and treated with heparin in advance.
) into the body, then insert its tip into the chyle cisterna,
Aronalpha (registered trademark) was instilled at the insertion site to prevent leakage of lymph fluid. I also fixed the polyethylene tube itself with Aron Alpha to prevent it from coming off. Next, collect lymph fluid from the polyethylene tube and drain it.
．． Use 5 ml for quantitative determination.
上記の血漿及びリンパ液の採取は、薬物溶液の経口投与
１＆８時間まで経時点に同時採取を行った。The above-mentioned plasma and lymph fluid were collected at the same time up to 1 and 8 hours after oral administration of the drug solution.
次いでこれら血漿及びリンパ液中のＧＡＳの定量は藤本
らの方法に準じて行った。すなわち、得られた血漿又は
リンパ？＆０．５ｍｌに精製水０．５ｍｌを加え全量１
．０ｍｌ とし、これにエタノール４ｍｌを加えたのち
氷水中に１５分間放置する。次いでこれを５分間振盪し
た後、２０００ｒｐｍで５分間遠心分離を行い、その上
澄液２．０ｍｌを試料とする。この試料に０．５％３−
メチル−２−ベンゾチアゾリン・ヒドラゾン塩酸塩溶液
１．０ｍｌを加え、さらに０．５％塩化第二鉄溶液１．
０ｍｌを加えたのち攪拌し発色させ、２０分後に、盲検
を対照として波長６００ｎｍで品性製作所のＵＶ−２４
０を用いて比色定量を行った。Next, GAS in these plasma and lymph fluids was quantified according to the method of Fujimoto et al. i.e. plasma or lymph obtained? & Add 0.5ml of purified water to 0.5ml to make a total volume of 1
．． 0 ml, add 4 ml of ethanol, and leave in ice water for 15 minutes. Next, after shaking this for 5 minutes, centrifugation is performed at 2000 rpm for 5 minutes, and 2.0 ml of the supernatant is used as a sample. This sample contains 0.5% 3-
Add 1.0 ml of methyl-2-benzothiazoline hydrazone hydrochloride solution, and add 1.0 ml of 0.5% ferric chloride solution.
After adding 0ml, stir to develop color, and after 20 minutes, use UV-24 from Kinsei Seisakusho at a wavelength of 600nm with a blind test as a control.
Colorimetric determination was performed using 0.
以上の結果を図示すれば第１図〜第５図のようになる。The above results are illustrated in FIGS. 1 to 5.
第１図 ＧＡＳ単独投与
第２図 ＧＡＳとＬ−グルタミン併用
第３図 ＧＡＳとジクロフェナックナトリウム併用第４
図 ＧＡＳと塩酸チアラミド併用
第５図 ＧＡＳとニトラゼパム併用
但し各図において（Ａ）は血漿中の、（Ｂ）はリンパ液
中の濃度を示し、０印は平均値でありその上下の伸びは
標準偏差である。Figure 1 GAS alone administration Figure 2 GAS and L-glutamine combination Figure 3 GAS and diclofenac sodium combination Figure 4
Figure 5 Combination of GAS and thiaramide hydrochloride Figure 5 Combination of GAS and nitrazepam However, in each figure, (A) shows the concentration in plasma, (B) shows the concentration in lymph, the 0 mark is the average value, and the growth above and below it is the standard deviation. It is.
これらの図から明らかなようにＧＡＳの吸収すなわち血
中濃度は、グルタミン、ジクロフェナック、チアラミド
又はニトラゼパムを配合することによって著しく増大し
、ＧＡＳの臨床応用上、極めて偉人な貢献を成すもので
ある。As is clear from these figures, the absorption of GAS, that is, the blood concentration, is significantly increased by incorporating glutamine, diclofenac, tialamide, or nitrazepam, making an extremely great contribution to the clinical application of GAS.
第１図はＧＡＳ単独、第２図はＬ−グルタミン配合剤、
第３図はジクロフェナックナトリウム配合剤、第４図は
塩酸チアラミド配合剤及び第５図はニトラゼパム配合剤
をそれぞれ経口投与したときの、（Ａ）は血漿中のそし
て（Ｂ）はリンパ液中の経時的な濃度変化を示す。
以上
Ｓ１７’わ
９Ｖ−ｔＥ）
＊を図
ν庁しゴ（スｒ）
手続補正書（方式）
％式％
特許庁長官 殿 １１？７なり年１０月２
１日差出１、事件の表示 特願昭６１−１６０６５２２
、発明の名称 グアヤズレンスルホン酸塩製剤３、補正
をする者
事件との関係 特許出願人
４、補正命令の日付（発送日）
昭和６１年９月３０日
５、補正の対象
明細書および図面
６、補正の内容Figure 1 shows GAS alone, Figure 2 shows L-glutamine combination,
Figure 3 shows the diclofenac sodium combination drug, Figure 4 shows the tiaramide hydrochloride combination drug, and Figure 5 shows the nitrazepam combination drug when administered orally, (A) in plasma and (B) in lymph over time. It shows a change in concentration. Above S17'wa9V-tE)
1 day submission, case display Patent application 1986-1606522
, Title of the invention Guayazulene sulfonate preparation 3. Relationship with the case of the person making the amendment Patent applicant 4. Date of amendment order (shipment date) September 30, 1985 5. Description and drawings subject to amendment 6. Contents of correction
Claims (1)
エナック、チアラミド若しくはニトラゼパム又はそれら
の塩類を配合した製剤1. Preparations containing guayazulene sulfonate and glutamine, diclofenac, tiaramide, nitrazepam, or their salts
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16065286A JPS6314719A (en) | 1986-07-08 | 1986-07-08 | Guaiazulenesulfonate preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16065286A JPS6314719A (en) | 1986-07-08 | 1986-07-08 | Guaiazulenesulfonate preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6314719A true JPS6314719A (en) | 1988-01-21 |
Family
ID=15719564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16065286A Pending JPS6314719A (en) | 1986-07-08 | 1986-07-08 | Guaiazulenesulfonate preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6314719A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0269421A (en) * | 1988-09-02 | 1990-03-08 | Lion Corp | Gastrointestinal drug |
| WO2006043336A1 (en) * | 2004-10-20 | 2006-04-27 | Kotobuki Pharmaceutical Co., Ltd. | Therapeutic or preventive composition for gastric mucosa disease |
-
1986
- 1986-07-08 JP JP16065286A patent/JPS6314719A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0269421A (en) * | 1988-09-02 | 1990-03-08 | Lion Corp | Gastrointestinal drug |
| WO2006043336A1 (en) * | 2004-10-20 | 2006-04-27 | Kotobuki Pharmaceutical Co., Ltd. | Therapeutic or preventive composition for gastric mucosa disease |
| JPWO2006043336A1 (en) * | 2004-10-20 | 2008-05-22 | 壽製薬株式会社 | Composition for treating or preventing gastric mucosal disease |
| JP4880477B2 (en) * | 2004-10-20 | 2012-02-22 | 壽製薬株式会社 | Pharmaceutical composition for the treatment of gastric mucosal disease |
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