JPS5943942B2 - Taurine derivative - Google Patents

Taurine derivative

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Publication number
JPS5943942B2
JPS5943942B2 JP54075148A JP7514879A JPS5943942B2 JP S5943942 B2 JPS5943942 B2 JP S5943942B2 JP 54075148 A JP54075148 A JP 54075148A JP 7514879 A JP7514879 A JP 7514879A JP S5943942 B2 JPS5943942 B2 JP S5943942B2
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JP
Japan
Prior art keywords
formula
taurine
compound
formulas
tables
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
Application number
JP54075148A
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Japanese (ja)
Other versions
JPS554381A (en
Inventor
ラフアエル・パソニ
ビツトリオ・カンボニ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
RABORATORIO KIMIKO FUARUMASEEUCHIKO KAUSHISU SpA
Original Assignee
RABORATORIO KIMIKO FUARUMASEEUCHIKO KAUSHISU SpA
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Application filed by RABORATORIO KIMIKO FUARUMASEEUCHIKO KAUSHISU SpA filed Critical RABORATORIO KIMIKO FUARUMASEEUCHIKO KAUSHISU SpA
Publication of JPS554381A publication Critical patent/JPS554381A/en
Publication of JPS5943942B2 publication Critical patent/JPS5943942B2/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

【発明の詳細な説明】 この発明の対象は、一般式 で示されるタウリン誘導体及びそれらの塩類である。[Detailed description of the invention] The object of this invention is the general formula These are taurine derivatives and salts thereof.

この発明は更に式（Ｉ）の化合物の製法、即ち次に記さ
れている様にジエタノールタウリン（式：）を３・４・
５−トリメトキシ安息香酸の反応性誘導体（式）（ハロ
ゲニド、エステル、（混合）酸無水物）と反応させる方
法にも関する。This invention further provides a method for preparing the compound of formula (I), namely, diethanoltaurine (formula:) as described below.
It also relates to a method for reacting 5-trimethoxybenzoic acid with reactive derivatives (formula) (halogenides, esters, (mixed) acid anhydrides).

式中Ｒは３・４・５−トリメトキシ安息香酸のアシル残
基を示し、Ｘはハロゲン原子（殊にクロル原子）又はメ
トキシ、エトキシなどのアルコキシ残基又はアルコキシ
−カルボキシル残基（特に残基−Ｏ −ＣＯ− ０Ｃ２
Ｈ５）を示す。上記諸反応はアルコール性を有する化合
物のアシル化に−般に用いられる条件下で行われる。Ｘ
がクロル原子を示す場合は、例えばアシル化はしばしば
トリエチルアミン又はピリジンの様な第三塩基の存在下
で行われる。なお、本発明の式（１）で示される化合物
は下記の方法によつても製造することができる。In the formula, R represents an acyl residue of 3,4,5-trimethoxybenzoic acid; O -CO- 0C2
H5) is shown. The above reactions are carried out under conditions commonly used for acylation of compounds having alcoholic properties. X
If represents a chloro atom, for example, the acylation is often carried out in the presence of a tertiary base such as triethylamine or pyridine. Note that the compound represented by formula (1) of the present invention can also be produced by the following method.

即ち、式。実施例 １ Ｎ−Ｎ−ジ〔２−（３・４・５−トリメトキシベンゾイ
ルオキシ）エチル〕一タウリン（ａ） Ｎ−Ｎ−ジ（２
−ヒドロキシ）エチルタウリン（式）水１５００ＴｒＬ
１にプロモエタンスルホン酸ナトリウム塩９０７及びエ
タノールアミン１１０ｆを溶解した溶液を約２時間蒸気
浴上で加熱する。That is, Eq. Example 1 N-N-di[2-(3,4,5-trimethoxybenzoyloxy)ethyl]mono-taurine (a) N-N-di(2
-Hydroxy)ethyltaurine (formula) water 1500TrL
A solution prepared by dissolving promoethanesulfonic acid sodium salt 907 and ethanolamine 110f in Example 1 is heated on a steam bath for about 2 hours.

反応混合物を一夜放置する。次いで過剰のジエタノール
アミン及び水を真空留去する。残渣を水１００ｍ１と濃
塩酸８００ｍ１に溶かした溶液を冷却し、塩化ナトリウ
ムを減圧瀘過する。次いで瀘液を減圧濃縮しこうして得
られた油状物を沸騰エタノールに取る。冷却すると、融
点１６３〜１６５℃を示す結晶性生成物を得る。The reaction mixture is left overnight. Excess diethanolamine and water are then removed in vacuo. A solution of the residue in 100 ml of water and 800 ml of concentrated hydrochloric acid is cooled and sodium chloride is filtered off under reduced pressure. The filtrate is then concentrated under reduced pressure and the oil thus obtained is taken up in boiling ethanol. Upon cooling, a crystalline product is obtained with a melting point of 163-165°C.

エタノールと水とから再結晶できる。１６７の生成物が
得られこのものの分析値及び分光値は標品と一致する。Can be recrystallized from ethanol and water. A product of 167 was obtained, and the analytical and spectroscopic values of this product matched those of the standard product.

（ｂ） Ｎ−Ｎ−ジ〔２−（３・４・５−トリメトキシ
ベンゾイルオキシ）エチル〕一タウリン実施例１（ａ）
で得られた生成物８．５ｙを無水ピリジン２５ｍ１に懸
濁し、これに３・４・５−トリメトキシベンゾイルクロ
リド１８．４７を攪拌しながら徐々に添加する。(b) N-N-di[2-(3.4.5-trimethoxybenzoyloxy)ethyl]-taurine Example 1(a)
8.5y of the product obtained above is suspended in 25ml of anhydrous pyridine, and 18.47ml of 3,4,5-trimethoxybenzoyl chloride is gradually added thereto with stirring.

室温に１時間放置した後、混合物を更に１時間８０℃に
加熱する。次いで室温まで冷却しエタノール５０ｍ１で
稀釈して冷蔵庫に放置する。１７４−１７８℃で熔ける
無色の結晶性化合物が沈澱する。After standing at room temperature for 1 hour, the mixture is heated to 80° C. for a further 1 hour. Then, cool to room temperature, dilute with 50 ml of ethanol, and leave in the refrigerator. A colorless crystalline compound precipitates which melts at 174-178°C.

メタノールから再結晶すると融点は１８０−１８３℃に
上昇する。純粋な生成物の収量は１１．５７であつた。
実施例 ２ Ｎ−Ｎ−ジ〔２−（３・４・５−トリメトキシベンゾイ
ルオキシ）エチル〕一タウリンタウリンナトリウム塩１
２７、水酸化バリウム１０７及びエチレンオキシド８ｙ
を水１００ｍ１に溶解し、９６時間１０℃に保つ。Recrystallization from methanol raises the melting point to 180-183°C. The yield of pure product was 11.57.
Example 2 N-N-di[2-(3.4.5-trimethoxybenzoyloxy)ethyl]mono-taurine taurine sodium salt 1
27, barium hydroxide 107 and ethylene oxide 8y
was dissolved in 100 ml of water and kept at 10°C for 96 hours.

ついでバリウムを硫酸で沈澱させ瀘去する．瀘液を減圧
下約５０ｍ１に濃縮する。約１ｆ．の濃塩酸を添加し、
生成した沈澱を瀘去し、瀘液を減圧下シロツプ状濃度と
なるまで濃縮させる。これを熱エタノールに取り冷却し
、得られた沈澱を瀘取して８０％エタノールから再結晶
すると、融点１６３−１６５℃を示す生成物を得る。こ
のものは実施例１の（ａ）で得られた生成物と一致する
。この生成物を実施例１の（ｂ）と同様に処理すると、
融点１７８−１８２℃のＮ−Ｎ−ジ〔２−（３・４・５
−トリメトキシベンゾイルオキシ）エチル〕一タウリン
を得る。Barium is then precipitated with sulfuric acid and filtered out. The filtrate is concentrated under reduced pressure to approximately 50 ml. Approximately 1f. of concentrated hydrochloric acid,
The formed precipitate is filtered off, and the filtrate is concentrated under reduced pressure to a syrupy consistency. This is taken in hot ethanol and cooled, and the resulting precipitate is filtered and recrystallized from 80% ethanol to obtain a product having a melting point of 163-165°C. This corresponds to the product obtained in Example 1 (a). When this product is treated similarly to Example 1 (b),
N-N-di[2-(3・4・5
-trimethoxybenzoyloxy)ethyl]-taurine is obtained.

このものは実施例１の（ｂ）で得られたものと一致する
。実施例 ３ Ｎ−Ｎ−ジ一〔２−（３・４・５丁トリメトキシベンゾ
イルオキシ）エチル〕一タウリンジエタノールアミン塩
酸塩１４７、ジメトキシエタン２００ｍ１及び３・４・
５−トリメトキシベンゾイルクロリド４７７の混合物を
室温で一夜攪拌する。This corresponds to that obtained in Example 1 (b). Example 3 N-N-di-[2-(3,4,5-trimethoxybenzoyloxy)ethyl]-taurine diethanolamine hydrochloride 147, dimethoxyethane 200ml and 3,4.
The mixture of 5-trimethoxybenzoyl chloride 477 is stirred at room temperature overnight.

過剰のＨＣｌを窒素気流中で除き、次いで溶液を減圧下
濃縮した後、無水エチルアルコール３００ｍ１に取る。
無水アルコール２００ｍ１中のナトリウムエチラート１
４ｆを冷却下添加し冷却したのちブロモエタンスルホン
酸ナトリウム塩２１７とヨードカリ１．７７を添加する
。室温に１２０時間保つた後、無機塩を瀘去し、瀘液を
減圧下少量になるまで濃縮する。一夜放置した後、瀘過
してメタノールから結晶化する。Excess HCl is removed in a stream of nitrogen, and the solution is then concentrated under reduced pressure and then taken up in 300 ml of absolute ethyl alcohol.
1 part sodium ethylate in 200 ml absolute alcohol
After cooling, 217 g of bromoethanesulfonic acid sodium salt and 1.77 g of potassium iodo were added. After 120 hours at room temperature, the inorganic salts are filtered off and the filtrate is concentrated under reduced pressure to a small volume. After standing overnight, it is filtered and crystallized from methanol.

生成物は１７９−１８２℃の融点を示し、実施例１で得
られたものと一致する。実施例 ４ Ｎ−Ｎ−ジ一〔２−（３・４・５−トリメトキシベンゾ
イルオキシ）エチル〕タウリン四塩化炭素２００ｍ１中
のエチレンオキシド４４７に３・４・５−トリメトキシ
ベンゾイルクロリド塩酸塩１８０ｙを少量ずつＯ℃で添
加、更に６時間攪拌する。The product exhibits a melting point of 179-182°C, consistent with that obtained in Example 1. Example 4 N-N-di-[2-(3,4,5-trimethoxybenzoyloxy)ethyl]taurine 180 y of 3,4,5-trimethoxybenzoyl chloride hydrochloride was added to 447 ethylene oxide in 200 ml of carbon tetrachloride. Add portionwise at 0° C. and stir for additional 6 hours.

溶媒を減圧下でとばし、残渣をジメトキシエタン１１に
取る。タウリンナトリウム塩７５７とヨードカリ１．５
７を添加後、１２０時間室温で攪拌する。減圧下蒸発さ
せ、ピリジン１００ｍ１を添加する。混合物をエタノー
ル３００ｍ１で稀釈し得られた固形物を瀘取する。メタ
ノールから再結晶して融点１７９−１８２の生成物を得
る。このものは実施例１で得られたものと一致する。本
発明の化合物は興味ある薬埋活性を有している。The solvent is removed under reduced pressure and the residue is taken up in dimethoxyethane 11. Taurine sodium salt 757 and iodopotassium 1.5
After adding 7, stir at room temperature for 120 hours. Evaporate under reduced pressure and add 100 ml of pyridine. The mixture was diluted with 300 ml of ethanol and the resulting solid was filtered. Recrystallization from methanol gives the product, melting point 179-182. This corresponds to that obtained in Example 1. The compounds of the invention have interesting pharmacological activity.

これらの活性について、以下説明する。Ｎ−Ｎ−ジ〔２
−（３・４・５−トリメトキシベンゾイルオキシ）エチ
ル〕一タウリン（化合物Ｂ）の薬理作用毒性（１８０日
以上継続投与） 雌雄マウスに化合物Ｂを２００ワ／Ｋ９ずつ１８０日間
にわたつて経口投与した。These activities will be explained below. N-N-di [2
Pharmacological toxicity of -(3,4,5-trimethoxybenzoyloxy)ethyl monotaurine (compound B) (continuous administration for 180 days or more) Compound B was orally administered at 200 W/K9 to male and female mice for 180 days. did.

死亡例は認められず、コントロールにくらべて体重増加
曲線にも何ら実質的な変化は見られなかつた。薬理 冷寒状態でのＣＣｌ４での肝蔵中毒に対する保護作用オ
イル中ＣＣｌ４２Ｏ％溶液を５ｍ１／Ｋ９経口投与する
と同時に、化合物Ｂの５００ｍノ／Ｋｇを腹腔内投与し
、次いで５時間４℃に保つた。No deaths were observed, and no substantial changes were observed in the weight gain curve compared to controls. Pharmacology Protective effect against liver poisoning with CCl4 in cold conditions A 20% solution of CCl4 in oil was administered orally at 5 ml/K9, and at the same time, 500 m/Kg of compound B was administered intraperitoneally and then kept at 4°C for 5 hours. .

血液中のＢＳＦ（５０ｍ９／Ｋ９静注）の試験を行つた
。比較化合物：ホモシステインチオラクトン（０ＣＴと
略） １群１０匹を使用。A test for BSF (50m9/K9 intravenously) in the blood was conducted. Comparative compound: Homocysteine thiolactone (abbreviated as 0CT) 10 animals per group were used.

結果はコントロール動物に対比してパーセント変化で示
す。ＢＳＦ胆汁分泌 化合物Ｂを１００ＴＩ１９／Ｋ９ずつ４日間腹腔内投与
した。Results are expressed as percent change relative to control animals. BSF bile secretion compound B was intraperitoneally administered at 100 TI19/K9 doses for 4 days.

４日目に最後の投与から１時間後、オイル中ＣＣｌ４ｌ
Ｏ％溶液を１０ｍ１／Ｋ９ラツトに経口投与した。On day 4, 1 hour after the last dose, 4 l of CCl in oil.
The O% solution was orally administered to 10ml/K9 rats.

胆汁中におけるＢＳＦ（５η／Ｋ９静注）の試験を行つ
た。１群１０匹を使用。BSF (5η/K9 intravenous injection) in bile was tested. 10 animals per group were used.

結果は分泌のパーセントとして示す。
北オイル中ＣＣｌ４ｌＯ％溶液を１０ｍ１／Ｋ９
経口投与した。化合物ＢｌＯＯη／Ｋ９を１時間後ラツ
トに腹腔内投与し、４時間後に血中のＢＳＦ（５０ｍ９
／Ｋ９静注）の試験を行つた。１群５匹を使用した。Results are expressed as percent secretion.
10ml/K9 of CCl4lO% solution in Kita Oil
Administered orally. Compound BlOOη/K9 was intraperitoneally administered to rats 1 hour later, and 4 hours later, blood BSF (50m9
/K9 intravenous injection) was tested. Five animals were used per group.

得られた結果を以下に示す。データはコントロール動物
に対するパーセント変化として表わす。化合物Ｂ−一３
４．２ＣＣ１４による中毒と治療処理 第１日目にオイル中ＣＣｌ４ｌＯ％溶液を１０ｍ１／Ｋ
９経口投与すると同時に化合物Ｂを１００ｍ９／Ｋｇ腹
腔内投与した。The results obtained are shown below. Data are expressed as percent change relative to control animals. Compound B-13
4.2 Poisoning and Treatment with CC14 On the first day of treatment, add 10 ml/K of CCl4lO% solution in oil.
At the same time as 9 oral administration, 100 m9/Kg of Compound B was intraperitoneally administered.

第２日目及び第３日目に化合物Ｂを１００ｍ９／Ｋｇ腹
腔内投与し、次いで血中のＢＳＦ（５０ｍ９／Ｋｇ静注
）の試験を行つた。１群５匹を使用Ｕ２た。Compound B was administered intraperitoneally at 100 m9/Kg on the second and third day, and then blood BSF (50 m9/Kg intravenously) was tested. U2 was used, with 5 animals per group.

得られた結果を以下にコントロール動物に対するパーセ
ント変化として表わす。化合物Ｂ−一２６．１ 抗脂血作用 ビスターラツトに４５口間モーリス食餌、ハンドラ一食
餌又はナス（Ｎａｔｈ）食餌を与えた。The results obtained are expressed below as percent change relative to control animals. Compound B-1 26.1 Antilipidemic Effect Vistar rats were fed Morris diet, Handler single diet or Nath diet for 45 mouths.

食餌と同時に化合物Ｂ又はコリン（但し、ナス食餌を除
く）を毎日２００即／Ｋｇずつ与えた。コントロール動
物群には食餌だけを与えた。１群１０匹を使用した。At the same time as the diet, Compound B or choline (excluding eggplant diet) was given at a dose of 200 g/kg every day. A control group of animals received chow only. 10 animals were used per group.

Claims (1)

【特許請求の範囲】 １ 一般式（ I ） ▲数式、化学式、表等があります▼（ I ）で示される
タウリン誘導体。 ２ 式（III） ▲数式、化学式、表等があります▼（III）で示される
ジエタノールタウリンを式（IV）▲数式、化学式、表等
があります▼（IV）式中Ｘは、ハロゲン原子、アルコキ
シ残基、又はアルコキシカルボニルオキシ残基を意味す
る、で示される３・４・５−トリメトキシ安息香酸の反
応性誘導体と反応させることを特徴とする式（ I ）▲
数式、化学式、表等があります▼（ I ）で示されるタ
ウリン誘導体の製法。[Claims] 1. A taurine derivative represented by the general formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼(I). 2 Formula (III) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ The diethanoltaurine represented by (III) is expressed as formula (IV) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ In the formula (IV), X is a halogen atom, alkoxy or an alkoxycarbonyloxy residue, the formula (I) is characterized by reacting with a reactive derivative of 3,4,5-trimethoxybenzoic acid represented by
There are mathematical formulas, chemical formulas, tables, etc.▼Production method of taurine derivative shown in (I).
JP54075148A 1978-06-15 1979-06-13 Taurine derivative Expired JPS5943942B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT0024587-A/78 1978-06-15
IT24587/78A IT1096662B (en) 1978-06-15 1978-06-15 TAURINIC DERIVATIVES FOR ANTI-LIPEMIC AND CHOLERETIC ACTIVITIES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM

Publications (2)

Publication Number Publication Date
JPS554381A JPS554381A (en) 1980-01-12
JPS5943942B2 true JPS5943942B2 (en) 1984-10-25

Family

ID=11214073

Family Applications (2)

Application Number Title Priority Date Filing Date
JP54075148A Expired JPS5943942B2 (en) 1978-06-15 1979-06-13 Taurine derivative
JP23774083A Pending JPS6133171A (en) 1978-06-15 1983-12-16 Taurine derivative

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP23774083A Pending JPS6133171A (en) 1978-06-15 1983-12-16 Taurine derivative

Country Status (9)

Country Link
JP (2) JPS5943942B2 (en)
BE (1) BE876969A (en)
DE (1) DE2901046C3 (en)
ES (3) ES476812A1 (en)
FR (2) FR2465717A1 (en)
GB (1) GB2023586B (en)
IT (1) IT1096662B (en)
LU (1) LU81379A1 (en)
NL (1) NL7904644A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1126575B (en) * 1979-12-07 1986-05-21 Causyth Chim Farm COMPOUND WITH ANTI-INFLAMMATORY, ANALGESIC AND ANTI-PIRETIC ACTIVITY, PROCESS FOR ITS PREPARATION, AND RELATED PHARMACEUTICAL COMPOSITIONS

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR920312A (en) * 1944-08-01 1947-04-03 Ward Process for the preparation of nicotic acid derivatives
GB586453A (en) * 1944-08-01 1947-03-19 Ward Blenkinsop & Co Ltd Process for the production of derivatives of nicotinic acid
CH520697A (en) * 1970-03-03 1972-03-31 Sopharma Sa Process for the preparation of a nicotinic acid ester-amide

Also Published As

Publication number Publication date
IT1096662B (en) 1985-08-26
GB2023586B (en) 1982-08-04
BE876969A (en) 1979-10-01
DE2901046A1 (en) 1979-12-20
ES476812A1 (en) 1979-12-16
ES482483A1 (en) 1980-04-16
FR2511365B1 (en) 1985-03-15
FR2465717A1 (en) 1981-03-27
IT7824587A0 (en) 1978-06-15
GB2023586A (en) 1980-01-03
FR2511365A1 (en) 1983-02-18
DE2901046B2 (en) 1981-07-16
NL7904644A (en) 1979-12-18
DE2901046C3 (en) 1982-05-06
JPS6133171A (en) 1986-02-17
JPS554381A (en) 1980-01-12
ES482484A1 (en) 1980-04-01
LU81379A1 (en) 1979-09-12

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