JPS6139286B2 - - Google Patents
Info
- Publication number
- JPS6139286B2 JPS6139286B2 JP8603481A JP8603481A JPS6139286B2 JP S6139286 B2 JPS6139286 B2 JP S6139286B2 JP 8603481 A JP8603481 A JP 8603481A JP 8603481 A JP8603481 A JP 8603481A JP S6139286 B2 JPS6139286 B2 JP S6139286B2
- Authority
- JP
- Japan
- Prior art keywords
- ulcer
- butanediol
- compound
- butanediol diester
- diester
- 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
- -1 2,3-butanediol diester Chemical class 0.000 claims description 15
- 239000003699 antiulcer agent Substances 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 14
- 238000007796 conventional method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- 230000000767 anti-ulcer Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- DPQCZNIGGNJGTD-UHFFFAOYSA-N Chloride-(??)-2-Methylpentanoic acid Natural products CCCCCCC=CCCCCCCCCCC(=O)OC(C)C(C)OC(=O)CCCCCCCC=CCCCCCC DPQCZNIGGNJGTD-UHFFFAOYSA-N 0.000 description 1
- DPQCZNIGGNJGTD-MVCBGFDASA-N Coixenolide Chemical compound CCCCCC\C=C\CCCCCCCCCC(=O)O[C@@H](C)[C@@H](C)OC(=O)CCCCCCC\C=C/CCCCCC DPQCZNIGGNJGTD-MVCBGFDASA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 230000005856 abnormality Effects 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003462 vein Anatomy 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
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
本発明は、２，３―ブタンジオールジエステル
誘導体を有効成分として含有する抗潰瘍剤に関す
る。
従来、２，３―ブタンジオールジエステル誘導
体については、僅かに、〓苡仁の成分であるコイ
クセノリドが抗潰瘍効果を有すること（特公昭36
―13349号）およびいくつかの２，３―ブタンジ
オール脂肪酸ジエステルが持続性香気香味賦与な
いし変調剤として利用できること（特開昭55―
154940号）が知られているにすぎなかつた。
本発明者は、２，３―ブタンジオールジエステ
ル誘導体（以下「ブタンジオールジエステル」と
称する）に関し、その薬理作用について鋭意検討
をおこなつていたところ、次の一般式（）、
（式中、R1、R2は同一又は異なつてアルキル
基又はアルケニル基を示す）
で表わされるブタンジオールジエステルが消化性
潰瘍の発生を強力に抑制するに作用を有すること
並びに当該物質は極めて毒性が低いことを見出
し、本発明を完成した。
従つて、本発明の目的は、ブタンジオールジエ
ステルを有効成分として含有する抗潰瘍剤を提供
するものである。
本発明の抗潰瘍剤の有効成分であるブタンジオ
ールジエステル（）は公知の化合物であるか、
あるいは公知の方法に従つて、例えばカルボン酸
クロライドを適当な溶媒、例えばエーテル中ピリ
ジンなどの存在下２，３―ブタンジオールと共に
室温にて撹拌し、反応終了後常法により処理する
ことによつて容易に製造されるものであり、例え
ば第１表のものが例示される。
The present invention relates to an antiulcer agent containing a 2,3-butanediol diester derivative as an active ingredient. Conventionally, with regard to 2,3-butanediol diester derivatives, it has been reported that coixenolide, a component of linseed, has a slight antiulcer effect (Japanese Patent Publication No. 36
13349) and that some 2,3-butanediol fatty acid diesters can be used as persistent aroma and flavor imparting or modulating agents (Japanese Patent Application Laid-Open No. 1983-1989).
No. 154940) was only known. The present inventor has been conducting extensive studies on the pharmacological effects of 2,3-butanediol diester derivatives (hereinafter referred to as "butanediol diester"), and has found the following general formula (): (In the formula, R 1 and R 2 are the same or different and represent an alkyl group or an alkenyl group.) The butanediol diester represented by: The present invention was completed based on the discovery that the Therefore, an object of the present invention is to provide an anti-ulcer agent containing butanediol diester as an active ingredient. Butanediol diester (), which is the active ingredient of the antiulcer agent of the present invention, is a known compound or
Alternatively, according to a known method, for example, a carboxylic acid chloride is stirred with 2,3-butanediol in a suitable solvent such as ether in the presence of pyridine at room temperature, and after the reaction is completed, the mixture is treated by a conventional method. They are easily manufactured, and examples include those shown in Table 1.
【表】【table】
【表】
これら化合物の代表的なものについて、抗潰瘍
作用及び急性毒性を試験した結果は次のとおりで
ある。
(i) 抗潰瘍作用
体重約200gのウイスター系雄性ラツトを24時
間絶食して実験を行つた。即ち、インドメタシン
を１％カルボキシメチルセルロースナトリウム水
溶液にて懸濁し、25mg／Kgを経口投与した。５時
間後に２％ブリリアントブルー生理食塩水溶液１
mlを尾静脈内に注入し、10分後に屠殺して全胃を
摘出した。その後１％ホルマリン水溶液12mlを注
入して固定後、平板上に拡げて胃体部に発生した
損傷部をノギスで計測し、その長さ（mm）の総和
をもつて潰瘍係数とした。
なお被検化合物は、ポリソルペート801滴を加
えた生理食塩水にて乳化又は懸濁し、インドメタ
シン投与の１時間前に背部に皮下注射を行つた。
潰瘍の抑制率は次式により求めた。
抑制率（％）＝コントロール群の潰瘍係数−被検化合物投与群の潰瘍係数／コントロール群の潰瘍係数×100
その結果は第２表のとおりである。[Table] The results of testing the antiulcer activity and acute toxicity of representative compounds are as follows. (i) Anti-ulcer effect An experiment was conducted in male Wistar rats weighing approximately 200 g, which were fasted for 24 hours. That is, indomethacin was suspended in a 1% sodium carboxymethyl cellulose aqueous solution, and 25 mg/Kg was orally administered. 2% Brilliant Blue Physiological Saline Solution 1 after 5 hours
ml was injected into the tail vein, and 10 minutes later, the animals were sacrificed and the whole stomach was removed. After fixation by injecting 12 ml of a 1% formalin aqueous solution, it was spread out on a flat plate, and the damaged area in the stomach body was measured with a caliper, and the sum of the lengths (mm) was taken as the ulcer index. The test compound was emulsified or suspended in physiological saline to which one drop of polysorbate 80 was added, and subcutaneously injected into the back one hour before indomethacin administration.
The ulcer suppression rate was calculated using the following formula. Inhibition rate (%) = Ulcer coefficient of control group - Ulcer coefficient of test compound administration group / Ulcer coefficient of control group x 100 The results are shown in Table 2.
【表】【table】
【表】
第２表から明らかな如く何れの被検化合物も強
い抗潰瘍作用を有する。
(ii) 急性毒性
被検化合物（第１表中、化合物番号１〜４、８
〜10、14〜18、21のもの）を綿実油に溶解し、こ
れを１群５匹のddY系雄性マウスの腹腔内に1000
mg／Kgの割合で投与し、７日間飼育観察した。７
日経過しても全てのマウスが生存し異常は認めら
れないので、何れの化合物もそのLD50は1000
mg／Kg以上であり、毒性は極めて弱いことは明ら
かである。
本発明の抗潰瘍剤は、経口、非経口のいずれの
方法によつても投与することができ、これに応じ
た各種剤型、例えば散剤、錠剤、カプセル剤、顆
粒剤、液剤等の経口投与剤；皮下、筋肉若しくは
静脈注射剤、輸液混合用剤または坐剤等の非経口
投与剤とすることができる。
上記製剤化は、自体公知の方法によつてなし得
る。すなわち、ブタンジオールジエステルをデン
プン、乳糖、マンニトール等の賦型剤；カルボキ
シメチルセルロースナトリウム、ヒドロキシプロ
ピルセルロース等の結合剤；結晶セルロース、カ
ルボキシメチルセルロースカルシウム等の崩壊
剤；タルク、ステアリン酸マグネシウム等の滑沢
剤；軽質無水ケイ酸等の流動性向上剤等を適宜組
み合せて処方することにより散剤、錠剤、カプセ
ル剤又は顆粒剤を製造することができる。また、
液剤、注射剤はブタンジオールエステルがオリー
ブ油、ラツカセイ油等に溶解することを利用して
油性の液剤若しくは注射剤とするか、あるいは当
該化合物を例えばポリソルベート60、ポリソルベ
ート80等の非イオン界面活性剤を用いて水、生理
食塩水等に溶解又は懸濁させて水性の液剤若しく
は注射剤とすることにより製造することができ
る。更に坐剤は、通常用いられる基剤、例えばカ
カオ脂、合成油脂等に常法により分散後固化させ
ることにより製造することができる。
斯くして得られた本発明の抗潰瘍剤の投与量
は、その疾患の程度によつても異なるが、通常成
人において、経口投与の場合には0.1〜1000mg／
Kg、非経口投与の場合には0.05〜500mg／Kgを１
日１回〜数回に分けて投与するのが好適である。
以下、更に実施例を挙げて本発明を説明する。
実施例１（錠剤）
常法に従い、下記組成の錠剤１個を製造した。
ブタンジオールジエステル 100mg
（第１表中、化合物番号１）
軽質無水ケイ酸 100mg
結晶セルロース 50mg
ヒドロキシプロピルセルロース 10mg
カルボキシメチルセルロースカルシウム 25mg
タルク ４mgステアリン酸マグネシウム ２mg
乳糖をもつて全量を350mgとする。
実施例２（顆粒剤）
常法に従い、下記組成の顆粒剤を製造した。
ブタンジオールジエステル 100mg
（第１表中、化合物番号１）
軽質無水ケイ酸 100mg
マンニツト 650mg
デンプン 135mgポリビニルピロリドン 15mg
全量 1000mg
実施例３（注射剤）
常法に従い、下記組成で油性注射剤を製造し
た。
ブタンジオールジエステル 100mg
（第１表中、化合物殿号２）ラツカセイ油 1900mg
全量 2000mg
実施例４（坐剤）
常法に従い、下記組成を溶融、撹拌後成型固化
し、坐剤１個を製造した。
ブタンジオールジエステル 100mg
（第１表中、化合物番号２）カカオ脂 1000mg
全量 1100mg[Table] As is clear from Table 2, all of the test compounds have strong anti-ulcer effects. (ii) Acute toxicity Test compound (compound numbers 1 to 4, 8 in Table 1)
-10, 14-18, 21) were dissolved in cottonseed oil and intraperitoneally administered to 5 ddY male mice per group at 1,000 doses.
The mice were administered at a rate of mg/Kg, and reared and observed for 7 days. 7
All the mice survived and no abnormalities were observed after a day had passed, so the LD 50 of each compound was 1000.
mg/Kg or more, and it is clear that the toxicity is extremely weak. The antiulcer agent of the present invention can be administered either orally or parenterally, and can be administered in various dosage forms depending on the oral administration, such as powders, tablets, capsules, granules, and liquids. Agents: Subcutaneous, intramuscular or intravenous injections, infusion preparations, or parenteral preparations such as suppositories can be used. The above formulation can be performed by a method known per se. That is, butanediol diester is mixed with excipients such as starch, lactose, and mannitol; binders such as sodium carboxymethyl cellulose and hydroxypropyl cellulose; disintegrants such as crystalline cellulose and calcium carboxymethyl cellulose; lubricants such as talc and magnesium stearate. Powders, tablets, capsules, or granules can be produced by appropriately combining and formulating fluidity improvers such as light anhydrous silicic acid. Also,
Liquids and injections can be made into oil-based solutions or injections by taking advantage of the fact that butanediol ester dissolves in olive oil, peanut oil, etc., or by adding the compound to a nonionic surfactant such as polysorbate 60 or polysorbate 80. It can be manufactured by dissolving or suspending it in water, physiological saline, etc. to prepare an aqueous solution or injection. Furthermore, suppositories can be produced by dispersing the compound in a commonly used base such as cacao butter, synthetic oil, etc., and then solidifying it by a conventional method. The dosage of the anti-ulcer agent of the present invention thus obtained varies depending on the severity of the disease, but is usually 0.1 to 1000 mg/dose for oral administration in adults.
kg, or 0.05 to 500 mg/Kg for parenteral administration.
It is suitable to administer once to several times a day. The present invention will be further described below with reference to Examples. Example 1 (Tablet) One tablet having the following composition was manufactured according to a conventional method. Butanediol diester 100mg (Compound No. 1 in Table 1) Light anhydrous silicic acid 100mg Crystalline cellulose 50mg Hydroxypropyl cellulose 10mg Carboxymethyl cellulose calcium 25mg Talc 4mg Magnesium stearate 2mg Lactose to make a total amount of 350mg. Example 2 (Granules) Granules having the following composition were manufactured according to a conventional method. Butanediol diester 100mg (Compound No. 1 in Table 1) Light silicic anhydride 100mg Mannitrate 650mg Starch 135mg Polyvinylpyrrolidone 15mg Total amount 1000mg Example 3 (Injection) An oily injection was produced with the following composition according to a conventional method. Butanediol diester 100mg (Compound No. 2 in Table 1) Rat casing oil 1900mg Total amount 2000mg Example 4 (Suppositories) The following composition was melted, stirred, and molded and solidified according to a conventional method to produce one suppository. Butanediol diester 100mg (Compound number 2 in Table 1) Cocoa butter 1000mg Total amount 1100mg
Claims (1)
基又はアルケニル基を示す） で表わされる２，３―ブタンジオールジエステル
誘導体を有効成分として含有する抗潰瘍剤。 ２ 経口投与形態である特許請求の範囲第１項記
載の抗潰瘍剤。 ３ 非経口投与形態である特許請求の範囲第１項
記載の抗潰瘍剤。[Claims] 1. General () An anti-ulcer agent containing a 2,3-butanediol diester derivative represented by the formula (wherein R 1 and R 2 are the same or different and represent an alkyl group or an alkenyl group) as an active ingredient. 2. The antiulcer agent according to claim 1, which is in an oral administration form. 3. The anti-ulcer agent according to claim 1, which is in a parenteral administration form.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8603481A JPS57200309A (en) | 1981-06-04 | 1981-06-04 | Antiulcerative |
| DE8181306100T DE3175184D1 (en) | 1980-12-26 | 1981-12-23 | 2,3-butanediol diester derivatives, process for producing the same, and an antiulcer drug containing the same |
| US06/333,772 US4469704A (en) | 1980-12-26 | 1981-12-23 | 2,3-Butanediol diester derivatives, process for producing the same, and an antiulcer drug containing the same |
| EP81306100A EP0056189B1 (en) | 1980-12-26 | 1981-12-23 | 2,3-butanediol diester derivatives, process for producing the same, and an antiulcer drug containing the same |
| US06/572,242 US4548753A (en) | 1980-12-26 | 1984-01-20 | 2,3-Butanediol diester derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8603481A JPS57200309A (en) | 1981-06-04 | 1981-06-04 | Antiulcerative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57200309A JPS57200309A (en) | 1982-12-08 |
| JPS6139286B2 true JPS6139286B2 (en) | 1986-09-03 |
Family
ID=13875378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8603481A Granted JPS57200309A (en) | 1980-12-26 | 1981-06-04 | Antiulcerative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57200309A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2847523B2 (en) * | 1989-03-29 | 1999-01-20 | マツダ株式会社 | Rotation mechanism of automotive front seat |
-
1981
- 1981-06-04 JP JP8603481A patent/JPS57200309A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57200309A (en) | 1982-12-08 |
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