JPH0524148B2 - - Google Patents
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- Publication number
- JPH0524148B2 JPH0524148B2 JP1252754A JP25275489A JPH0524148B2 JP H0524148 B2 JPH0524148 B2 JP H0524148B2 JP 1252754 A JP1252754 A JP 1252754A JP 25275489 A JP25275489 A JP 25275489A JP H0524148 B2 JPH0524148 B2 JP H0524148B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- compound
- mixture
- ethyl acetate
- 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
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
（産業上の利用分野）
本発明はトロンボキサンA2拮抗作用を有する
インダン誘導体の新規合成中間体及びその製法に
関する。
（従来の技術）
トロンボキサンA2（Thromboxan A2、以下
TxA2と称する）は動物の各種臓器（例えば、肝
臓、腎臓、肺臓、脳等）に広く存在しているアラ
キドン酸が代謝されて生成し、このTxA2が有す
る血小板凝集作用に起因して、しばしば末梢動脈
血栓症、肺塞栓症、冠動脈閉塞症、心筋梗塞症、
一過性脳虚血症等の各種血栓症が引き起こされる
ことが知られている。このため、TxA2に基づく
血小板凝集を抑制する物質として４−（２−ベン
ゼンスルホニルアミノエチル）フエノキシ酢酸が
報告されている〔トロンボシス・リサーチ
（Thrombosis Research）、第35巻、379−395頁
（1984年）〕。
（発明の構成及び効果）
本発明は一般式
（但し、R1はトリフルオロメチルフエニル基、
ニトロフエニル基、ナフチル基又は含硫複素環式
基、R2は低級アルコキシカルボニル基又はカル
ボキシル基を表す。）
で示されるインダン誘導体に関する。
本発明の目的化合物は、各種医薬化合物、例え
ば上記公知化合物に較べて一層優れたTxA2拮抗
作用を有する医薬化合物、の合成中間体として有
用な新規化合物である。かかる目的化合物の具体
例としては、一般式（）において、R1がブロ
モフエニル基、トリフルオロメチルフエニル基、
ニトロフエニル基、ナフチル基又はチエニル基で
ある化合物があげられる。
本発明の目的化合物（）は１子の不斉炭素原
子に基づく２種の光学異性体及びその混合物をい
ずれも包含するものである。
本発明によれば、目的化合物（）は、例え
ば、一般式
（但し、R2は前記と同一意味を有する。）
で示されるアミノインダン化合物又はその塩と一
般式
R1SO3H （）
（但し、R1は前記と同一意味を有する。）
で示されるスルホン酸化合物又はその反応性誘導
体とを縮合反応させ、要すれば生成物を加水分解
して製造することができる。
アミノインダン化合物（）又はその塩とスル
ホン酸化合物（）又はその反応性誘導体との縮
合反応は脱酸剤の存在又は非存在下に実施するこ
とができる。化合物（）の反応性誘導体として
は、慣用の反応性誘導体、例えば対応するスルホ
ニルハライド化合物が好適にあげられる。脱酸剤
としては、後えば炭酸アルカリ金属、炭酸水素ア
ルカリ金属、トリアルキルアミン、ピリジンなど
慣用のものをいずれも用いることができる。また
アミノインダン化合物（）の塩としては、鉱酸
塩及び有機酸塩を適宜用いることができる。本反
応は適当な溶媒（例えば水、酢酸エチル）中冷却
〜加温下で実施するのが好ましい。
また、加水分解は例えばアルカリ試薬又は酸で
処理することにより実施することができる。アル
カリ試薬としては例えば水酸化アルカリ金属を、
酸としては例えば鉱酸を適宜用いることができ
る。本加水分解は適当な溶媒（例えば、水、低級
アルカノール）中冷却〜加温下で実施するのが好
ましい。
上記反応はすべてラセミ化を伴わずに進行する
ため、光学活性な原料化合物からは光学活性な目
的化合物（）を得ることができる。
上記の如くして得られる本発明化合物（）
は、遊離カルボン酸またはその塩のいずれの形で
でも合成中間体として使用でき、かかる塩として
は、例えばアルカリ金属塩、アルカリ土類金属
塩、トリエチルアミン塩、ビリジン塩、塩基性ア
ミノ塩酸の如き有機アミノ塩があげられる。
また、かかる目的化合物（）及びその塩は、
例えば、一般式R3−NH2（但し、R3は低級アルコ
キシカルボニル低級アルキル基又はカルボキシ低
級アルキル基を表す。）で示される化合物とペプ
チド縮合させれば、一般式
（但し、記号は前記と同一意味を有する。）
とすることができる（特願昭63−289801）。
この化合物（）は、トロンボシス・リサーチ
（Thrombosis Research）、第35巻、379−395頁
（1984年）記載の化合物に較べてより強力な
TxA2拮抗作用を有し、血小板凝集抑制剤、血栓
症の予防・治療剤、冠・脳血管などの平滑筋攣縮
及び喘息の予防・治療剤として有用な医薬化合物
である。
なお、本発明の原料化合物（）は、例えば２
−アミノインダンとアセチルクロリドとを溶媒中
脱酸剤の存在下反応させて２−アセチルアミノイ
ンダンとし、該化合物とハロ（メチルチオ）酢酸
低級アルキルエステルとを溶媒中反応させた後還
元剤で処理して、２−アセチルアミノ−５−低級
アリコキシカルボニルメチル−インダンとし、該
化合物を加水分解後、常法により脱アセチル化し
て製造することができる。
実施例 １
(1) （２−アミノインダン−５−イル）酢酸メチ
ルエステル・塩酸塩4.83ｇ、炭酸カリウム8.29
ｇ、水40ml、酢酸エチル100ml及び４−ニトロ
フエニルスルホニルクロリド4.43ｇの混合物を
室温で１時間撹拌する。反応混合物から酢酸エ
チル層を分取し、食塩水で洗浄、乾燥後減圧下
に溶媒を留去する。得られる粗製物を酢酸エチ
ル−イソプロピルエーテル−ｎ−ヘキサン混液
から再結晶して｛２−〔（４−ニトロフエニル）
スルホニルアミノ〕−インダン−５−イル｝酢
酸メチルエステル7.43ｇを得る。
m.p. 122〜124℃
MS（ｍ／ｅ）：390（M+）
IRνnujolmaxcm-1：3280、1720
(2) 本品7.32ｇのメタノール70ml溶液に1N水酸
化ナトリウム水溶液37mlを加え室温で１時間攪
拌後、減圧下に溶媒を留去する。残渣を水に溶
解し、10％塩酸で約PH１とした後酢酸エチルで
抽出する。抽出液を乾燥後減圧下に溶媒を留去
する得られる粗製物を酢酸エチル−ｎ−ヘキサ
ン混液から再結晶して｛２−〔（４−ニトロフエ
ニル）スルホニルアミノ〕−インダン−５−イ
ル｝酢酸6.71ｇを得る。
m.p. 173−174℃
MS（ｍ／ｅ）：376（M+）
IRνnujol naxcm-1：3285、1700
ナトリウム塩：m.p. 173−176℃（イソプロピ
ルアルコール−水から再結晶）
実施例 ２〜４
(1) 対応原料化合物を実施例１−(1)と同様に処理
して下記第１表記載化合物を得る。
(Industrial Application Field) The present invention relates to a novel synthetic intermediate for indane derivatives having thromboxane A 2 antagonistic activity and a method for producing the same. (Prior art) Thromboxan A 2 (hereinafter referred to as Thromboxan A 2 )
TxA 2 ) is produced by the metabolism of arachidonic acid, which is widely present in various organs of animals (e.g. liver, kidneys, lungs, brain, etc.), and due to the platelet aggregation effect of TxA 2 , Often peripheral arterial thrombosis, pulmonary embolism, coronary artery occlusion, myocardial infarction,
It is known that various thromboses such as transient cerebral ischemia are caused. For this reason, 4-( 2 -benzenesulfonylaminoethyl)phenoxyacetic acid has been reported as a substance that inhibits platelet aggregation based on TxA2 [Thrombosis Research, Vol. 35, pp. 379-395 (1984 Year)〕. (Structure and effects of the invention) The present invention is based on the general formula (However, R 1 is a trifluoromethylphenyl group,
A nitrophenyl group, a naphthyl group or a sulfur-containing heterocyclic group, R 2 represents a lower alkoxycarbonyl group or a carboxyl group. ) Regarding an indane derivative represented by The object compound of the present invention is a novel compound useful as a synthetic intermediate for various pharmaceutical compounds, for example, a pharmaceutical compound that has superior TxA 2 antagonistic activity compared to the above-mentioned known compounds. Specific examples of such target compounds include, in the general formula (), R 1 is a bromophenyl group, a trifluoromethylphenyl group,
Examples include compounds having a nitrophenyl group, a naphthyl group or a thienyl group. The object compound () of the present invention includes both two types of optical isomers based on one asymmetric carbon atom and mixtures thereof. According to the invention, the target compound () may be, for example, of the general formula (However, R 2 has the same meaning as above.) Aminoindan compound or its salt represented by the general formula R 1 SO 3 H () (However, R 1 has the same meaning as above.) It can be produced by subjecting a sulfonic acid compound or a reactive derivative thereof to a condensation reaction and, if necessary, hydrolyzing the product. The condensation reaction between the aminoindan compound () or its salt and the sulfonic acid compound () or its reactive derivative can be carried out in the presence or absence of an acid absorbing agent. Suitable examples of the reactive derivative of compound () include conventional reactive derivatives, such as the corresponding sulfonyl halide compounds. As the deoxidizing agent, any commonly used deoxidizing agent can be used, such as alkali metal carbonate, alkali metal hydrogencarbonate, trialkylamine, and pyridine. Furthermore, as the salt of the aminoindan compound (), mineral acid salts and organic acid salts can be used as appropriate. This reaction is preferably carried out in a suitable solvent (eg, water, ethyl acetate) under cooling to heating. Hydrolysis can also be carried out, for example, by treatment with an alkaline reagent or an acid. Examples of alkaline reagents include alkali metal hydroxide,
As the acid, for example, a mineral acid can be used as appropriate. This hydrolysis is preferably carried out in a suitable solvent (eg, water, lower alkanol) under cooling to heating. Since all of the above reactions proceed without racemization, the optically active target compound ( ) can be obtained from the optically active starting compound. Compound of the present invention obtained as described above ()
can be used as a synthetic intermediate in either the form of a free carboxylic acid or a salt thereof, and such salts include organic compounds such as alkali metal salts, alkaline earth metal salts, triethylamine salts, biridine salts, and basic amino hydrochloric acids. Amino salts are available. In addition, such target compound () and its salt are:
For example, if a peptide is condensed with a compound represented by the general formula R 3 -NH 2 (wherein R 3 represents a lower alkoxycarbonyl lower alkyl group or a carboxy lower alkyl group), the general formula (However, the symbols have the same meanings as above.) (Japanese Patent Application No. 63-289801). This compound () is more potent than the compound described in Thrombosis Research, Vol. 35, pp. 379-395 (1984).
It has a TxA 2 antagonistic effect and is a useful pharmaceutical compound as a platelet aggregation inhibitor, a prophylactic/therapeutic agent for thrombosis, a prophylactic/therapeutic agent for smooth muscle spasm of coronary and cerebrovascular vessels, and asthma. Note that the raw material compound () of the present invention is, for example, 2
- Reacting aminoindan and acetyl chloride in a solvent in the presence of a deoxidizing agent to produce 2-acetylaminoindan, reacting the compound with halo(methylthio)acetic acid lower alkyl ester in a solvent, and then treating with a reducing agent. 2-acetylamino-5-lower alkoxycarbonylmethyl-indane can be produced by hydrolyzing the compound and then deacetylating it by a conventional method. Example 1 (1) (2-Aminoindan-5-yl)acetic acid methyl ester hydrochloride 4.83g, potassium carbonate 8.29
A mixture of 40 ml of water, 100 ml of ethyl acetate and 4.43 g of 4-nitrophenylsulfonyl chloride is stirred at room temperature for 1 hour. The ethyl acetate layer is separated from the reaction mixture, washed with brine, dried, and then the solvent is distilled off under reduced pressure. The obtained crude product was recrystallized from a mixture of ethyl acetate-isopropyl ether-n-hexane to give {2-[(4-nitrophenyl)
7.43 g of sulfonylamino]-indan-5-yl}acetic acid methyl ester are obtained. mp 122-124℃ MS (m/e): 390 (M + ) IRν nujolmax cm -1 : 3280, 1720 (2) Add 37 ml of 1N sodium hydroxide aqueous solution to 70 ml of methanol solution of 7.32 g of this product and keep at room temperature for 1 hour. After stirring, the solvent is distilled off under reduced pressure. The residue was dissolved in water, adjusted to pH 1 with 10% hydrochloric acid, and extracted with ethyl acetate. After drying the extract, the solvent was distilled off under reduced pressure. The resulting crude product was recrystallized from a mixture of ethyl acetate and n-hexane to give {2-[(4-nitrophenyl)sulfonylamino]-indan-5-yl}acetic acid. Obtain 6.71g. mp 173-174℃ MS (m/e): 376 (M + ) IRν nujol nax cm -1 : 3285, 1700 Sodium salt: mp 173-176℃ (recrystallized from isopropyl alcohol-water) Examples 2-4 ( 1) The corresponding raw material compounds are treated in the same manner as in Example 1-(1) to obtain the compounds listed in Table 1 below.
【表】
(2) 上記(1)の生成物を実施例１−(2)と同様に処理
して下記第２表記載化合物を得る。[Table] (2) The product of (1) above was treated in the same manner as in Example 1-(2) to obtain the compounds listed in Table 2 below.
(1) ２−アミノインダン塩酸塩10.40ｇ、炭酸カ
リウム34.2ｇ、水100ml及び酢酸エチル150mlの
混合物に氷冷下塩化アセチル9.68ｇを滴下す
る。混合物を０℃で1.5時間攪拌した後酢酸エ
チル層を分取し、洗浄、乾燥後減圧下に溶媒を
留去する。残査を酢酸エチル−ｎ−ヘキサン混
液から再結晶して２−アセチルアミノインダン
9.5ｇを無色結晶として得る。
m.p. 126.5〜127.5℃
(2) 本品13.06ｇ、クロロ（メチルチオ）酢酸
エチルエステル13.35ｇ及び塩化メチレン100ml
の混合物に塩化第二スズ40.0ｇの塩化メチレン
50ml溶液を氷冷下滴下する。混合物を０℃〜室
温で２時間撹拌後、氷に注加し酢酸エチルで抽
出する。抽出液を10％塩酸、炭酸水素ナトリウ
ム水溶液及び食塩水で順次洗浄し、乾燥後減圧
下に溶媒を留去する。残査（24.3ｇ）を酢酸
150mlに溶解し、亜鉛末100ｇを加え２時間加熱
還流する。冷後、混合物をろ過し、ろ液を減圧
下に濃縮して酢酸を留去する。残査に水と酢酸
エチルを加え、酢酸エチル層を分取する。酢酸
エチル液を炭酸水素ナトリウム水溶液及び食塩
水で洗浄し、乾燥後減圧下に溶媒を留去する。
得られる粗結晶をエーテル−ｎ−ヘキサン混合
液から再結晶して（２−アセチルアミノインダ
ン−５−イル）酢酸エチルエステル15.67ｇを
無色結晶として得る。
m.p. 82〜84℃
(3) 本品16.69ｇ及び2N塩酸100mlの混合物を18
時間加熱還流する。反応後、減圧下に溶媒を留
去し、残査にメタノール100mlを加え１時間加
熱還流する。冷後、減圧下に溶媒を留去し、得
られる粗結晶をメタノールイソプロピルアルコ
ール−イソロピルエーテル混液から再結晶して
（２−アミノインダン−５−イル）酢酸メチル
エステル塩酸塩15.14ｇを無色結晶として得る。
m.p. 145〜148℃
(1) 9.68 g of acetyl chloride was added dropwise to a mixture of 10.40 g of 2-aminoindan hydrochloride, 34.2 g of potassium carbonate, 100 ml of water, and 150 ml of ethyl acetate under ice cooling. After stirring the mixture at 0°C for 1.5 hours, the ethyl acetate layer was separated, washed and dried, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 2-acetylaminoindan.
9.5 g are obtained as colorless crystals. mp 126.5～127.5℃ (2) 13.06g of this product, 13.35g of chloro(methylthio)acetic acid ethyl ester and 100ml of methylene chloride
40.0 g of stannic chloride and methylene chloride in a mixture of
Add 50 ml of the solution dropwise under ice cooling. The mixture was stirred at 0°C to room temperature for 2 hours, then poured onto ice and extracted with ethyl acetate. The extract is washed successively with 10% hydrochloric acid, an aqueous sodium bicarbonate solution, and brine, and after drying, the solvent is distilled off under reduced pressure. The residue (24.3g) was dissolved in acetic acid.
Dissolve in 150ml, add 100g of zinc powder, and heat under reflux for 2 hours. After cooling, the mixture is filtered, and the filtrate is concentrated under reduced pressure to remove acetic acid. Water and ethyl acetate are added to the residue, and the ethyl acetate layer is separated. The ethyl acetate solution is washed with an aqueous sodium hydrogen carbonate solution and brine, and after drying, the solvent is distilled off under reduced pressure.
The resulting crude crystals were recrystallized from an ether-n-hexane mixture to obtain 15.67 g of (2-acetylaminoindan-5-yl)acetic acid ethyl ester as colorless crystals. mp 82-84℃ (3) A mixture of 16.69g of this product and 100ml of 2N hydrochloric acid
Heat to reflux for an hour. After the reaction, the solvent is distilled off under reduced pressure, 100 ml of methanol is added to the residue, and the mixture is heated under reflux for 1 hour. After cooling, the solvent was distilled off under reduced pressure, and the resulting crude crystals were recrystallized from a mixture of methanol isopropyl alcohol and isopyl ether to obtain 15.14 g of (2-aminoindan-5-yl)acetic acid methyl ester hydrochloride. Obtained as crystals. mp 145~148℃
Claims (1)
ニトロフエニル基、ナフチル基又は含硫複素環式
基、R2は低級アルコキシカルボニル基又はカル
ボキシル基を表す。） で示されるインダン誘導体。 ２ 一般式 （但し、R2は低級アルコキシカルボニル基又は
カルボキシル基を表す。） で示されるアミノインダン化合物又はその塩と一
般式 R1SO3H （但し、R1はトリフルオロメチルフエニル基、
ニトロフエニル基、ナフチル基又は含硫複素環式
基を表す。） で示されるスルホン酸化合物又はその反応性誘導
体とを縮合反応させることを特徴とする一般式 （但し、記号は前記と同一意味を有する。） で示されるインダン誘導体の製法。 ３ 一般式 （但し、R1はトリフルオロメチルフエニル基、
ニトロフエニル基、ナフチル基又は含硫複素環式
基、R21は低級アルコキシカルボニル基を表す。） で示されるインダン誘導体を加水分解することを
特徴とする一般式 （但し、記号は前記と同一意味を有する。） で示されるインダン誘導体の製法。[Claims] 1. General formula (However, R 1 is a trifluoromethylphenyl group,
A nitrophenyl group, a naphthyl group or a sulfur-containing heterocyclic group, R 2 represents a lower alkoxycarbonyl group or a carboxyl group. ) is an indane derivative represented by 2 General formula (However, R 2 represents a lower alkoxycarbonyl group or a carboxyl group.) An aminoindan compound or its salt represented by the general formula R 1 SO 3 H (However, R 1 is a trifluoromethylphenyl group,
Represents a nitrophenyl group, a naphthyl group, or a sulfur-containing heterocyclic group. ) A general formula characterized by a condensation reaction with a sulfonic acid compound represented by (However, the symbols have the same meanings as above.) A method for producing an indane derivative shown by: 3 General formula (However, R 1 is a trifluoromethylphenyl group,
A nitrophenyl group, a naphthyl group or a sulfur-containing heterocyclic group, R 21 represents a lower alkoxycarbonyl group. ) A general formula characterized by hydrolyzing an indane derivative represented by (However, the symbols have the same meanings as above.) A method for producing an indane derivative shown by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25275489A JPH02149553A (en) | 1989-09-28 | 1989-09-28 | Indane derivative and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25275489A JPH02149553A (en) | 1989-09-28 | 1989-09-28 | Indane derivative and production thereof |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63289801A Division JPH02138248A (en) | 1987-11-18 | 1988-11-16 | Indane derivative, its production and synthetic intermediate thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02149553A JPH02149553A (en) | 1990-06-08 |
| JPH0524148B2 true JPH0524148B2 (en) | 1993-04-06 |
Family
ID=17241822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25275489A Granted JPH02149553A (en) | 1989-09-28 | 1989-09-28 | Indane derivative and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02149553A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3623944A1 (en) * | 1986-07-16 | 1988-02-11 | Thomae Gmbh Dr K | NEW BENZOLSULFONAMIDO INDANYL COMPOUNDS, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
-
1989
- 1989-09-28 JP JP25275489A patent/JPH02149553A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02149553A (en) | 1990-06-08 |
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