JPH0242826B2 - - Google Patents
Info
- Publication number
- JPH0242826B2 JPH0242826B2 JP55181247A JP18124780A JPH0242826B2 JP H0242826 B2 JPH0242826 B2 JP H0242826B2 JP 55181247 A JP55181247 A JP 55181247A JP 18124780 A JP18124780 A JP 18124780A JP H0242826 B2 JPH0242826 B2 JP H0242826B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acetic acid
- general formula
- phenylthiophenyl
- acid
- 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 - Lifetime
Links
- UOCQATUFLPHRNG-UHFFFAOYSA-N 2-phenyl-2-phenylsulfanylacetic acid Chemical class C=1C=CC=CC=1C(C(=O)O)SC1=CC=CC=C1 UOCQATUFLPHRNG-UHFFFAOYSA-N 0.000 claims description 5
- JMIYLNQBNSEKAO-UHFFFAOYSA-N 2-(2-phenylsulfanylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1SC1=CC=CC=C1 JMIYLNQBNSEKAO-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- -1 dibenzothiepine propionic acid derivative Chemical class 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- UTFSPWRTXCDUIJ-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethoxy)phenol Chemical compound OC1=CC=C(OC(F)(F)F)C(F)=C1 UTFSPWRTXCDUIJ-UHFFFAOYSA-N 0.000 description 2
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MUXFZBHBYYYLTH-UHFFFAOYSA-N Zaltoprofen Chemical compound O=C1CC2=CC(C(C(O)=O)C)=CC=C2SC2=CC=CC=C21 MUXFZBHBYYYLTH-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004325 thiepin-2-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C(*)S1 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Description
【発明の詳細な説明】
本発明は次の一般式（）
で表わされるフエニルチオフエニル酢酸誘導体に
関する。[Detailed Description of the Invention] The present invention is based on the following general formula () This invention relates to a phenylthiophenyl acetic acid derivative represented by:
本発明化合物から導かれる一般式（）
で表わされるジベンゾチエピンプロピオン酸誘導
体は、すぐれた抗炎症作用ならびに鎮痛作用を有
する。例えば、カラゲニン浮腫法による抗炎症作
用では、２−（10，11−ジヒドロ−10−オキソジ
ベンゾ〔ｂ，ｆ〕チエピン−２−イル）プロピン
酸は、インドメサシンの約２倍の効力を有し、さ
らに酢酸ライジング法による鎮痛作用では、アス
ピリンの20倍もの効力を有する。 General formula () derived from the compound of the present invention The dibenzothiepine propionic acid derivative represented by has excellent anti-inflammatory and analgesic effects. For example, in terms of anti-inflammatory effects measured by the carrageenan edema method, 2-(10,11-dihydro-10-oxodibenzo[b,f]thiepin-2-yl)propionic acid has approximately twice the potency of indomethacin; Furthermore, the analgesic effect achieved by the acetic acid rising method is 20 times more effective than aspirin.
また、ラツトにおける急性毒性値、LD50値は
232mgであり安全性の高い有用な抗炎症剤として
期待される（特開昭55−53282）。 In addition, the acute toxicity value and LD50 value in rats are
232mg, it is expected to be a highly safe and useful anti-inflammatory agent (Japanese Patent Application Laid-Open No. 55-53282).
本発明者らは、すぐれた薬理作用を有する一般
式（）で示される化合物の工業的かつ経済的製
法について鋭意検討した結果、一般式（）で表
わされる化合物が中間原料として有用なことを見
い出し本発明を完成した。 The present inventors have conducted intensive studies on industrial and economical methods for producing compounds represented by the general formula () that have excellent pharmacological effects, and have discovered that the compound represented by the general formula () is useful as an intermediate raw material. The invention has been completed.
従つて、本発明の目的は一般式（）で表わさ
れるフエニルチオフエニル酢酸誘導体を提供せん
とすることにある。 Therefore, an object of the present invention is to provide a phenylthiophenyl acetic acid derivative represented by the general formula ().
本発明化合物は、次式で示される方法により容
易に有用な薬理作用を有する一般式（）の化合
物にすることが出来る。 The compound of the present invention can be easily converted into a compound of the general formula () having a useful pharmacological action by the method shown by the following formula.
従来一般式（）で表わされる化合物は、下記
反応工程により製造されてきた。 Conventionally, the compound represented by the general formula () has been produced by the following reaction steps.
（式中、Ｒは低級アルキル基を示す。）
しかしながら前記公知方法における、化合物
（）から化合物（）への閉環反応にみられる
低収率、さらには、化合物（）を加水分解反応
に付した後、得られる粗生成物から化合物（）
を単離精製するのに必要であつたカラムクロマト
グラフイーによる処理等、工業的製法において重
大な問題点を、本発明化合物を閉環反応に付すこ
とにより改善することが出来る。また、本発明化
合物は、公知中間体化合物、たとえば、一般式
（）あるいは一般式（）の化合物と比較して
容易に結晶化するため、単離および精製操作をた
やすくおこなうことが出来、工業的操作を有利に
おこなうことが可能である。 (In the formula, R represents a lower alkyl group.) However, in the above-mentioned known method, the yield is low in the ring-closing reaction from compound () to compound (), and furthermore, when compound () is subjected to a hydrolysis reaction, From the crude product obtained after, compound ()
Significant problems in industrial production methods, such as column chromatography treatment required to isolate and purify the compound, can be improved by subjecting the compound of the present invention to a ring-closing reaction. In addition, the compound of the present invention crystallizes easily compared to known intermediate compounds, such as compounds of general formula () or general formula (), so isolation and purification operations can be easily performed, and industrial It is possible to advantageously carry out targeted operations.
例えば、本発明化合物から導かれる特に好まし
い化合物２−（10，11−ジヒドロ−10−オキソジ
ベンゾ〔ｂ，ｆ〕チエピン−２−イル）プロピオ
ン酸は、５−（α−カルボキシ）エチル−２−フ
エニルチオフエニル酢酸をポリリン酸中、閉環反
応に付した後、得られる粗生成物を、従来必要で
あつたカラムクロマトグラフイーによる処理をお
こなうことなく、再結晶により63％以上の収率で
得られる。即ち本発明化合物を閉環することによ
り、前記公知方法による収率を大巾に向上させる
ことに成功した。 For example, a particularly preferred compound derived from the compounds of the present invention, 2-(10,11-dihydro-10-oxodibenzo[b,f]thiepin-2-yl)propionic acid, is 5-(α-carboxy)ethyl-2- After subjecting phenylthiophenyl acetic acid to a ring-closing reaction in polyphosphoric acid, the resulting crude product is recrystallized with a yield of 63% or more without the conventional column chromatography treatment. It can be obtained with That is, by ring-closing the compound of the present invention, we succeeded in greatly improving the yield obtained by the above-mentioned known method.
本発明化合物は、一般式（）の化合物のエス
テル基とニトリル基を加水分解して得られる。 The compound of the present invention can be obtained by hydrolyzing the ester group and nitrile group of the compound of general formula ().
反応は、反応溶媒として、水あるいはアルコー
ル類たとえばメタノール、エタノール等、さらに
は、テトラヒドロフラン、ジオキサン、ジメチル
ホルムアミド、酢酸など一般に使用される有機溶
媒を水との共存下に用い塩酸、硫酸、臭化水素酸
などの鉱酸あるいは、水酸化ナトリウム、水酸化
カリウム等のアルカリ存在下、反応温度は特に限
定されるものではないが、好ましくは室温から加
熱還流の範囲であり、反応時間は、用いる溶媒、
反応温度さらには、酸あるいはアルカリの量によ
つて異なるが、多くは、数時間で行うことが出来
る。 The reaction is carried out using water or alcohols such as methanol, ethanol, etc., as well as commonly used organic solvents such as tetrahydrofuran, dioxane, dimethylformamide, and acetic acid in the coexistence of water as a reaction solvent. In the presence of a mineral acid such as an acid or an alkali such as sodium hydroxide or potassium hydroxide, the reaction temperature is not particularly limited, but is preferably in the range of room temperature to reflux, and the reaction time is determined by the solvent used,
Although it varies depending on the reaction temperature and the amount of acid or alkali, in most cases it can be carried out in several hours.
以下、実施例によつて本発明を説明する。 The present invention will be explained below with reference to Examples.
実施例 １
５−（α−カルボキシエチル）−２−フエニルチ
オフエニル酢酸：
エチル５−（α−シアノエチル）−２−フエニル
チオフエニルアセテート（）11.0ｇに酢酸55
ml、47％臭化水素酸55mlを順次加え、撹拌下に５
時間加熱還流する。反応物を減圧濃縮し、冷水を
加え酢酸エチルで抽出する。酢酸エチル層を飽和
食塩水で洗浄後、飽和炭酸水素ナトリウム溶液と
ともに振とうし、水層を分取する。水層は塩酸酸
性としたのち酢酸エチルで抽出する。酢酸エチル
層は飽和食塩水で洗浄後、無水硫酸マグネシウム
で乾燥した。酢酸エチルを減圧下で留去し、ほぼ
無色の結晶9.6ｇを得た。ベンゼン−ｎ−ヘキサ
ンより再結晶して融点143〜144.5℃の無色結晶と
して５−（α−カルボキシエチル）−２−フエニル
チオフエニル酢酸8.4ｇを得た（収率78.5％）。Example 1 5-(α-carboxyethyl)-2-phenylthiophenyl acetic acid: Add 55% of acetic acid to 11.0 g of ethyl 5-(α-cyanoethyl)-2-phenylthiophenyl acetate ().
ml, 55 ml of 47% hydrobromic acid were added sequentially, and 55 ml of 47% hydrobromic acid was added under stirring.
Heat to reflux for an hour. The reaction mixture was concentrated under reduced pressure, added with cold water, and extracted with ethyl acetate. After washing the ethyl acetate layer with saturated brine, it is shaken with saturated sodium bicarbonate solution and the aqueous layer is separated. The aqueous layer is acidified with hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure to obtain 9.6 g of almost colorless crystals. Recrystallization from benzene-n-hexane gave 8.4 g of 5-(α-carboxyethyl)-2-phenylthiophenyl acetic acid as colorless crystals with a melting point of 143 to 144.5°C (yield 78.5%).
IRνKBr naxcm-1：3400〜2400，1690（COOH）
NMR（DMSO−d6）δ：1.36（3H，ｄ，Ｊ＝７
Hz，＝CHCH3）
3.70（3H，ｑ，Ｊ＝０Hz，＝CHCH3＋−
CH2CO2H）
7.10〜7.50（8H，ｍ，芳香族プロトン）
12.20（2H，ｂ，−COOH×２）
参考例
２−（10，11−ジヒドロ−10−オキソジベンゾ
〔ｂ，ｆ〕チエピン−２−イル）プロピオン酸
５−（α−カルボキシエチル）−２−フエニルチ
オフエニル酢酸（）1.0ｇにポリリン酸20.6ｇ
を加え、70℃で３時間、加熱、撹拌する。冷水を
加え、クロロホルムで抽出した。クロロホルム層
を飽和食塩水で洗浄したのち無水硫酸マグネシウ
ムで乾燥した。クロロホルムを減圧下に留去して
得られた残渣を放置し、結晶化させ、ベンゼン−
ｎ−ヘキサンより再結晶し、融点130.5〜131.5℃
の微黄色結晶として２−（10，11−ジヒドロ−10
−オキソジベンゾ〔ｂ，ｆ〕チエピン−２−イ
ル）プロピオン酸0.8ｇを得た（収率84.8％）。 IRν KBr nax cm -1 : 3400-2400, 1690 (COOH) NMR (DMSO-d 6 ) δ: 1.36 (3H, d, J=7
Hz, = CHCH 3 ) 3.70 (3H, q, J = 0Hz, = CHCH 3 +-
CH2CO2H ) 7.10-7.50 (8H, m, aromatic proton) 12.20 (2H, b, -COOH x 2) Reference example 2-(10,11-dihydro - 10-oxodibenzo[b,f]thiepin -2-yl)propionic acid 5-(α-carboxyethyl)-2-phenylthiophenyl acetic acid () 1.0g and polyphosphoric acid 20.6g
Add and heat and stir at 70°C for 3 hours. Cold water was added and extracted with chloroform. The chloroform layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The residue obtained by distilling off chloroform under reduced pressure was left to crystallize, and benzene-
Recrystallized from n-hexane, melting point 130.5-131.5℃
2-(10,11-dihydro-10
0.8 g of -oxodibenzo[b,f]thiepin-2-yl)propionic acid was obtained (yield 84.8%).
IRνKBr naxcm-1：1710，1675（CO）
NMR（CDCl3）δ：1.46（3H，ｄ，Ｊ＝７Hz，
＝CHCH3）
3.68（1H，ｑ，Ｊ＝７Hz，＝CHCH3）
4.29（2H，ｓ，−CH2CO−）
6.92〜7.64（6H，ｍ，芳香族プロトン）
8.07（1H，dd，Ｊ＝８，２Hz，C9−Ｈ）
10.02（1H，b.s，−COOH）
MSm／ｅ：298（M+） IRν KBr nax cm -1 : 1710, 1675 (CO) NMR (CDCl 3 ) δ: 1.46 (3H, d, J = 7Hz,
= CHCH3 ) 3.68 (1H, q, J=7Hz, = CHCH3 ) 4.29 (2H, s, -CH2CO- ) 6.92~7.64 (6H, m, aromatic proton) 8.07 (1H, dd, J= 8.2Hz, C 9 -H) 10.02 (1H, bs, -COOH) MSm/e: 298 (M + )
Claims (1)
２−フエニルチオフエニル酢酸であることを特徴
とする特許請求の範囲第１項記載のフエニルチオ
フエニル酢酸誘導体。[Claims] 1 General formula () A phenylthiophenyl acetic acid derivative represented by 2 () In the formula, 5-(α-carboxyethyl)-
The phenylthiophenyl acetic acid derivative according to claim 1, which is 2-phenylthiophenyl acetic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18124780A JPS57106656A (en) | 1980-12-23 | 1980-12-23 | Phenylthiophenylacetic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18124780A JPS57106656A (en) | 1980-12-23 | 1980-12-23 | Phenylthiophenylacetic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57106656A JPS57106656A (en) | 1982-07-02 |
| JPH0242826B2 true JPH0242826B2 (en) | 1990-09-26 |
Family
ID=16097360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18124780A Granted JPS57106656A (en) | 1980-12-23 | 1980-12-23 | Phenylthiophenylacetic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57106656A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5553282A (en) * | 1978-10-17 | 1980-04-18 | Nippon Chemiphar Co Ltd | Dibenzothiepin derivative and its preparation |
-
1980
- 1980-12-23 JP JP18124780A patent/JPS57106656A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5553282A (en) * | 1978-10-17 | 1980-04-18 | Nippon Chemiphar Co Ltd | Dibenzothiepin derivative and its preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57106656A (en) | 1982-07-02 |
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