JPS594408B2 - Kanjiyo Hydroxykagobutsuno Seizouhou - Google Patents
Kanjiyo Hydroxykagobutsuno SeizouhouInfo
- Publication number
- JPS594408B2 JPS594408B2 JP10360273A JP10360273A JPS594408B2 JP S594408 B2 JPS594408 B2 JP S594408B2 JP 10360273 A JP10360273 A JP 10360273A JP 10360273 A JP10360273 A JP 10360273A JP S594408 B2 JPS594408 B2 JP S594408B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- seizouhou
- kanjiyo
- hydroxykagobutsuno
- general formula
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 本発明は、一般式 □ （Ｉ） で示される化合物を還元して一般式 ”゜ □ 。[Detailed description of the invention] The present invention is based on the general formula □ (I) The general formula is obtained by reducing the compound shown by ”゜ □.
。、 ２０で示される化合物を製造する方法に関する。. , The present invention relates to a method for producing the compound represented by No. 20.
上記式中、Ａはカルボキシル基または低級アルコキシカ
ルボニル基を示す。前記一般式においてＡで示される低
級アルコキシカルボニル基としてはたとえばメトキシカ
ルボ２５ニル、エトキシカルボニル、ｎ−プロポキシカ
ルボニル、ｉ−プロポキシカルボニル、ｎ−ブトキシカ
ルボニル、ｓｅｃ−ブトキシカルボニル、を−ブトキシ
カルボニルなどがあげられる。In the above formula, A represents a carboxyl group or a lower alkoxycarbonyl group. Examples of the lower alkoxycarbonyl group represented by A in the above general formula include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, and -butoxycarbonyl. It will be done.
本発明の方法は一般式（Ｉ）で表わされる化合３０物を
還元することよりなる。The method of the present invention consists of reducing compound 30 represented by general formula (I).
この還元は、一般にカルボニル基をアルコールに還元す
る方法であれば、いかなる方法でもよいが、実用的には
、たとえば水素化ホウ素ナトリウムや水素化アルミニウ
ムリチウムなどり金属水素化物を用いる方法、パ３５ラ
ジウム、ニッケル、白金、鉄、ロジウム、イリジウムな
どの金属触媒を用いる接触還元、ナトリウム、リチウム
、カリウムなどのアルカリ金属とアルコール、液体アン
モニアのような水素供与性溶媒を用いる還元、ロジウム
、インジウムなどの金属錯体を用いる還元などがよい。Generally, this reduction may be carried out by any method as long as it reduces a carbonyl group to an alcohol, but in practice, for example, a method using a metal hydride such as sodium borohydride or lithium aluminum hydride; , catalytic reduction using metal catalysts such as nickel, platinum, iron, rhodium, iridium, etc., reduction using alkali metals such as sodium, lithium, potassium and alcohols, hydrogen-donating solvents such as liquid ammonia, metals such as rhodium, indium, etc. Reduction using a complex is preferable.
反応は一般に、冷却下ないし加熱下で進行し、反応温度
、反応時間などに特に限定はない。The reaction generally proceeds under cooling or heating, and there are no particular limitations on the reaction temperature, reaction time, etc.
また接触還元の場合、水素は常圧または加圧下で用い、
その水素圧に特に限定はない。水素化アルミニウムリチ
ウムを用いる場合には、無水のエーテル系溶媒（例、エ
チルエーテル、プロピルエーテル、イソプロピルエーテ
ル、テトラヒドロフラン、ジオキサン、エチレングリコ
ールジメチルエーテル、エチレングリコールジエチルエ
ーテル）、アルカリ金属を用いる場合には、液体アンモ
ニア、無水アルコール類（例、メタノール、工汐ノール
、プロパノール、イソプロパノール、ブタノール、イソ
フッノール）などが溶媒として好ましい。その他の場合
には、水、アルコール類、エーテル類などが用いられ特
に限定はない。かくして得られる一般式（）の化合物は
、蒸留、再結晶、カラムクロマトグラフイ一などの通常
の手段により分離、精製することが出来る。かくして得
られる化合物は、下記反応式に従つて、下記一般式（）
または（Ｖ）で示される化合物に導くことができ、この
化合物（）または（Ｖ）はきわめてすぐれた消炎、鎮痛
、解熱作用を示し、たとえば消炎剤、鎮痛剤、解熱剤な
どとして有用である。In addition, in the case of catalytic reduction, hydrogen is used at normal pressure or under pressure,
There is no particular limitation on the hydrogen pressure. When using lithium aluminum hydride, an anhydrous ether solvent (e.g., ethyl ether, propyl ether, isopropyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether), and when using an alkali metal, a liquid Ammonia, anhydrous alcohols (eg, methanol, Kosho alcohol, propanol, isopropanol, butanol, isofluorol), and the like are preferred as the solvent. In other cases, water, alcohols, ethers, etc. are used, and there are no particular limitations. The compound of general formula () thus obtained can be separated and purified by conventional means such as distillation, recrystallization, and column chromatography. The compound thus obtained has the following general formula () according to the following reaction formula.
Alternatively, the compound (V) can be derived, and this compound () or (V) exhibits extremely excellent anti-inflammatory, analgesic, and antipyretic effects, and is useful as, for example, an anti-inflammatory agent, analgesic, and antipyretic agent.
〔上記式中、Ａは前記と同意義であり、Ｂはベンゾイル
基を示す。[In the above formula, A has the same meaning as above, and B represents a benzoyl group.
〕実施例 １
１２０１１１のエタノールに、５．７７の１−オキソイ
ンダン一４−カルボン酸メチルエステルを加え、室温で
攪拌する。Example 1 5.77 of 1-oxoindan-4-carboxylic acid methyl ester was added to 120111 of ethanol and stirred at room temperature.
次に６００ηの水素化ホウ素ナトリウムを加え、１時間
３０分撹拌したのち４ｍ１のアセトンを加え、さらに３
０分攪拌を続ける。減圧下溶媒を留去し残留物に水と希
塩酸を加えエーテルで抽出する。抽出層は水、飽和食塩
水で洗つたのち乾燥する。減圧下溶媒を留去すると、１
ヒドロキシインダン一４−カルボン酸メチルエステルが
得られる。エーテル一石油エーテルから再結晶すると、
融点６５−６７℃を示す。元素分析値 ＣｌｌＨｌ２Ｏ
３
計算値 Ｃ：６８．７３Ｈ：６．２９
実験値 Ｃ：６８．４０Ｈ：６６４２
実施例 ２
水酸化ナトリウム４．４ｔを水１００ｍ１に溶かし、こ
れに１−オキソインダン一４−カルボン酸１７．６ｙを
加える。Next, 600η of sodium borohydride was added, and after stirring for 1 hour and 30 minutes, 4ml of acetone was added, and an additional 3ml of acetone was added.
Continue stirring for 0 minutes. The solvent was distilled off under reduced pressure, water and diluted hydrochloric acid were added to the residue, and the mixture was extracted with ether. The extracted layer is washed with water and saturated saline, and then dried. When the solvent is distilled off under reduced pressure, 1
Hydroxyindane-4-carboxylic acid methyl ester is obtained. When recrystallized from ether-petroleum ether,
It exhibits a melting point of 65-67°C. Elemental analysis value CllHl2O
3 Calculated value C: 68.73H: 6.29 Experimental value C: 68.40H: 6642 Example 2 Dissolve 4.4t of sodium hydroxide in 100ml of water, and add 17.6y of 1-oxoindan-4-carboxylic acid to this. Add.
これを冷水浴で冷やしながら水素化ホウ素ナトリウム１
．８９７を加える。浴を除いて３時間かきまぜた後、ア
セトン５ｍ１を加える。１時間後、反応液を氷７０ｔと
濃塩酸３０ｍ１との溶液に加えて析出する結晶を▲別し
、アセトンから再結晶すると１−ヒドロキシインダン一
４カルボン酸が得られる。While cooling this in a cold water bath, add 1 part of sodium borohydride.
．． Add 897. After removing the bath and stirring for 3 hours, add 5 ml of acetone. After 1 hour, the reaction solution was added to a solution of 70 t of ice and 30 ml of concentrated hydrochloric acid, and the precipitated crystals were separated and recrystallized from acetone to obtain 1-hydroxyindan-4 carboxylic acid.
融点１７４〜１７６℃（分解）元素分析値 ＣｌＯＨｌ
ＯＯ８
計算値 Ｃ：６７．４１、Ｈ：５．６６
実験値 Ｃ：６７．１７、Ｈ：５．４１Melting point 174-176℃ (decomposition) Elemental analysis value ClOHl
OO8 Calculated value C: 67.41, H: 5.66 Experimental value C: 67.17, H: 5.41
Claims (1)
ボニル基を示す。 〕で示される化合物を還元することを特徴とする一般式
▲数式、化学式、表等があります▼ 〔式中、Ａは前記と同意義〕で示される化合物の製造法
。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, A represents a carboxyl group or a lower alkoxycarbonyl group. ] A method for producing a compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, A has the same meaning as above].
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10360273A JPS594408B2 (en) | 1973-09-13 | 1973-09-13 | Kanjiyo Hydroxykagobutsuno Seizouhou |
| CA205,943A CA1048041A (en) | 1973-08-11 | 1974-07-30 | Benzalicyclic carboxylic acid derivatives |
| FI2361/74A FI59788C (en) | 1973-08-11 | 1974-08-08 | FOERFARANDE FOER FRAMSTAELLNING AV SOM FEBERNEDSAETTANDE SMAERTSTILLANDE OCH INFLAMMATION MOTVERKANDE MEDEL ANVAENDBARA 4-BENZOYL-INDAN-1-KARBOXYLSYRAFOERENINGAR |
| FR7427644A FR2257282B1 (en) | 1973-08-11 | 1974-08-08 | |
| SE7410175A SE421522B (en) | 1973-08-11 | 1974-08-08 | SET TO PREPARE 4-ACYLARED 1-INDUCARBOXYL ACIDS RESPECTIVE 5-ACYLARED 1,2,3,4-TETRAHYDRO-1-Naphthalene CARBOXYL ACIDES, AND CERTAIN AMIDS AND ESTERS THEREOF |
| NL7410752A NL7410752A (en) | 1973-08-11 | 1974-08-09 | PROCESS FOR PREPARING NEW BENZO-CYCLO-ALIPHATIC CARBONIC ACID DERIVATIVES. |
| GB35171/74A GB1480231A (en) | 1973-08-11 | 1974-08-09 | Benzalicyclic carboxylic acid derivatives |
| NO742873A NO143573C (en) | 1973-08-11 | 1974-08-09 | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVITY INDAN-1-CARBOXYLIC ACID DERIVATIVES |
| DK424874AA DK139514B (en) | 1973-08-11 | 1974-08-09 | Analogous process for the preparation of indane-1-carboxylic acid derivatives. |
| DE19742438380 DE2438380C2 (en) | 1973-08-11 | 1974-08-09 | 4-Benzoylindan-1-carboxylic acids, 4-Benzylindan-1-carboxylic acids, 4-Benzoylindan-1-carbonitriles, 4-Benzoylindan-1-ones, 1-Carbamoylindan-4-carboxylic acid, 1-Cyano-indane-4-carboxylic acid and functional derivatives of carboxylic acids |
| GB488577A GB1480232A (en) | 1973-08-11 | 1974-08-09 | Carboxylic diketones |
| BE147478A BE818698A (en) | 1973-08-11 | 1974-08-09 | BENZALICYCLIC CARBOXYLIC ACID DERIVATIVES |
| US05/496,855 US3953500A (en) | 1973-08-11 | 1974-08-12 | Benzalicyclic carboxylic acid derivative |
| NO751045A NO145573C (en) | 1973-08-11 | 1975-03-25 | INTERMEDIATE FOR USE IN THE PREPARATION OF THERAPEUTIC EFFECTIVE INDAN-1-CARBOXYLIC ACID DERIVATIVES |
| US05/647,810 US4007225A (en) | 1973-08-11 | 1976-01-09 | 4-Benzoylindan-1-carboxamide and derivatives thereof |
| US05/742,111 US4111997A (en) | 1973-08-11 | 1976-11-15 | Benzalicyclic carboxylic acid derivative |
| CA319,616A CA1078871A (en) | 1973-08-11 | 1979-01-15 | Benzalicyclic compounds and their production |
| CH243279A CH616140A5 (en) | 1973-08-11 | 1979-03-14 | Process for the preparation of indan- and tetrahydronaphthalene-carboxamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10360273A JPS594408B2 (en) | 1973-09-13 | 1973-09-13 | Kanjiyo Hydroxykagobutsuno Seizouhou |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5058045A JPS5058045A (en) | 1975-05-20 |
| JPS594408B2 true JPS594408B2 (en) | 1984-01-30 |
Family
ID=14358305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10360273A Expired JPS594408B2 (en) | 1973-08-11 | 1973-09-13 | Kanjiyo Hydroxykagobutsuno Seizouhou |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS594408B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02304849A (en) * | 1989-05-18 | 1990-12-18 | Jeol Ltd | Transmission electron microscope having measuring function |
-
1973
- 1973-09-13 JP JP10360273A patent/JPS594408B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02304849A (en) * | 1989-05-18 | 1990-12-18 | Jeol Ltd | Transmission electron microscope having measuring function |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5058045A (en) | 1975-05-20 |
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