JPS58201763A - Indoleacetoxyacetic acid ester - Google Patents
Indoleacetoxyacetic acid esterInfo
- Publication number
- JPS58201763A JPS58201763A JP8286182A JP8286182A JPS58201763A JP S58201763 A JPS58201763 A JP S58201763A JP 8286182 A JP8286182 A JP 8286182A JP 8286182 A JP8286182 A JP 8286182A JP S58201763 A JPS58201763 A JP S58201763A
- Authority
- JP
- Japan
- Prior art keywords
- indoleacetoxyacetic
- acid ester
- formula
- acetate
- 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.)
- Granted
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本・発４明は新規なインドールアセトキシ酢酸エステル
、更に゛詳細には、次の一般式ａｉ。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel indoleacetoxyacetic ester, more specifically, the following general formula ai.
（式中、−ＲはＣ３〜０１１１の直鎖又は分岐鎖潰アル
キル基を示す）
で表わされるインドールアセトキシ酢酸エステルに関す
る。(In the formula, -R represents a C3-0111 linear or branched alkyl group.)
（１）式のイント一−ル骨゛格′３位の”アセトキシ酢
酸エステル基の代りに酢酸基が置換したインドメタシン
及び（１）式中Ｒ′が水素原子で表わされるプ”セメタ
゛シ゛ンは卓□越した”消炎鎮痛作用を有し、“特′に
′ｉ！ｈ”者゛は現□在臨床゛にお゛いて゛広く使用さ
れている。Indomethacin in which an acetate group is substituted in place of the acetoxyacetate group at the 3-position of the central skeleton in formula (1), and a substitute in which R' in formula (1) is a hydrogen atom are table □ It has superior anti-inflammatory and analgesic effects, and is especially effective! ``h'' agents are currently widely used in clinical practice.
しかしながら、これらは遊離カルボン酸の形で経口もし
くは９直・腸内投与されるか、あるｂはアルカリ塩の形
で注射投与式れているが、経口及び直腸内投与の場合は
しばしば重篤々消化管障害を惹起し、また注射投与の場
合はショック、アレルギー等の副作用をおこす難点があ
り、その改善が望まれていた。However, these can be administered orally or rectally in the form of free carboxylic acids, or by injection in the form of alkaline salts, but oral and rectal administration often causes severe It has the disadvantage that it causes gastrointestinal disorders, and when administered by injection, it causes side effects such as shock and allergies, and improvement of these problems has been desired.
一方、インドールアセトキシ酢酸エステルとしては、（
１）式中Ｒがメチル基で表わされるインドールアセトキ
シ酢酸メチルエステルが知られているが、これはインド
ールアセトキシ酢酸に比較し、消炎作用が１／１００〜
１／１０と低いとされており（特公昭５１−４７７０８
号）、医薬品としての利用可能性が否定でれていた。On the other hand, as indole acetoxyacetic ester, (
1) Indoleacetoxyacetic acid methyl ester, in which R is a methyl group, is known, but this has an anti-inflammatory effect that is 1/100 to 1/100 that of indoleacetoxyacetic acid.
It is said to be as low as 1/10 (Tokuko Sho 51-47708
(No.), the possibility of its use as a medicine was denied.
斯かる実情において、本発明者はインドールアセトキシ
酢酸のエステル類は副作用が少ないことに着目し、鋭意
研究を行った結果、（１）式で表わされる本発明化合物
がインドメタシン及びアセメタシンと同勢の強い消炎鎮
痛作用を有し、しかも副作用が弱い仁とを見出し、本発
明を完成した。Under these circumstances, the present inventor focused on the fact that esters of indole acetoxyacetic acid have few side effects, and as a result of intensive research, it was found that the compound of the present invention represented by formula (1) is as strong as indomethacin and acemethacin. The present invention was completed by discovering that the compound has anti-inflammatory and analgesic effects and has weak side effects.
従って、本発明は、消炎鎮痛剤として有用な新規なイン
ドールアセトキシ酢酸エステル（１）を提供するもので
ある。Therefore, the present invention provides a novel indoleacetoxyacetic acid ester (1) useful as an anti-inflammatory analgesic.
本発明の官ンドールアセトキシ酢酸エステルは、インド
ールアセトキシ酢酸〔（Ｉ）式中Ｒ＝Ｈの化合物〕とア
ルコール（ＲＯＭ ）とを通常のエステル化方法によっ
て反応させること ３−
によって製造される。すなわち、両者を適当な脱水縮合
剤、例えばｎｃｃの存在下反応させる直接法、あるいは
何れか一方を反応性誘導体とする間接法尋によって行わ
れる。The indole acetoxy acetic acid ester of the present invention is produced by reacting indole acetoxy acetic acid [a compound of formula (I) with R=H] and an alcohol (ROM) by a conventional esterification method. That is, it is carried out by a direct method in which both are reacted in the presence of a suitable dehydration condensation agent such as ncc, or by an indirect method in which either one is used as a reactive derivative.
次に実施例を挙げて説明する。Next, an example will be given and explained.
実施例１
イソブチルオキシカルボニルメチル・１−（ｐ−クロロ
ベンゾイル）−５−メトキシ−２−メチルインドール−
３−アセテート：アセメタシン２．０８Ｆｉ、イソブチ
ルアルコール０．３７グ、ＤＣＣ１，０３ｔｓ ４−ジ
メチルアミノピリジン０．０６Ｐ、シアツメ、チル４〇
−の混液を室温にて１５時間攪拌する。反応後不溶物を
枦去し、Ｆ液を濃縮し、残油をシリカゲルカラムクロマ
ト精製（展開液：酢酸 ４ −
エチル：ｎ−ヘキサン≧１ ： ４ ） Ｌ、黄色油状
物ｘ、９ｏ）（収率８ｏ、６％）を得る。これを酢酸エ
チル−ｎ−ヘキサンより結晶化して、融点７０〜７１℃
の淡黄色粉末を得る。Example 1 Isobutyloxycarbonylmethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-
3-Acetate: A mixed solution of 2.08 Fi of acemetacin, 0.37 g of isobutyl alcohol, 1,03 ts of DCC, 0.06 P of 4-dimethylaminopyridine, 40 of Shiatsume, and 40 of Til is stirred at room temperature for 15 hours. After the reaction, insoluble matters were removed, liquid F was concentrated, and the residual oil was purified by silica gel column chromatography (developing solution: 4-ethyl acetate:n-hexane≧1:4) L, yellow oil x, 9o) (harvested 8o, 6%). This was crystallized from ethyl acetate-n-hexane, with a melting point of 70-71°C.
A pale yellow powder is obtained.
Ｍ８ Ｉｖ／ｓ：４７３［：Ｍ ｆｏｒ ３１Ｃｔ］
＋ ４７１［Ｍ”ｆ Ｏｒ ” ＣＬ ） ｔ ３１１
Ｃ，Ｍ” −ＣＯＯＣＨ２ＣＯＯＣ４Ｈｇ ’） ＊
１６８０ （ＣＯＮ） 、 ”Ｈ−ＮＭＲ（ＣＤＣ１，
）δニア、６７（２Ｈ。M8 Iv/s:473 [:M for 31Ct]
+ 471 [M"f Or "CL) t 311
C, M"-COOCH2COOC4Hg') *
1680 (CON), “H-NMR (CDC1,
) δ near, 67 (2H.
買
Ｃ４−Ｈ） ＃ ６．８８ （Ｉ Ｈｅ ｄ ｅ Ｊ”
８．６ Ｈｚ −Ｃ？−ＩＴ ） 。Buy C4-H) #6.88 (I He de J”
8.6 Hz -C? -IT).
６．６７ （ＩＨｓ ｄ 、 ｄ 、 ＃ Ｊｏｒｔｈ
ｏ＝９．０Ｈｚ ＊ Ｊｍｅｔａ＝２．７Ｈｚ 、 ｃ
、−ａ） 、４．６５（２ａ、 ｍ 、ＯＣＨ，Ｃｏｏ
） 。6.67 (IHs d, d, #Jorth
o=9.0Hz * Jmeta=2.7Hz, c
, -a) ,4.65(2a,m,OCH,Coo
).
ａ、９ａ（ｚａ、ａ、Ｊ＝６゜６ Ｈｇ ＊ ０ＣＨｚ
Ｑ（＜ ） ＋ ３．８５（ａＨｓ ｍ ＊ ０ＣＨ３
） ＊ ３．７９ （２Ｈ＃ ｌ ｒ Ｃ５−ＣＨｌ）
＃２．３９（３Ｈ１＊−Ｃ１−ＣＨｓ） 、１．９１
（ＩＨ２７重線。a, 9a (za, a, J=6゜6 Hg * 0CHz
Q (< ) + 3.85 (aHs m * 0CH3
) * 3.79 (2H# l r C5-CHl)
#2.39 (3H1*-C1-CHs), 1.91
(IH27 double line.
実施例２
ｎ−オクチルオキシカルボニルメチル弓−（ｐ−クロロ
ベンゾイル）−５−メトキシ−２−メチルインドール−
３−アセテート：アセメタシン２．０８９ ％ ｎ−オ
クチルアルコール０．６５ ｆ／、 ＤＣＣ１，０３９
、シアノメチル５０ｍ、４−ジメチルアミノピリジン０
．０６ｆの混液を室温にて１５時間攪拌する。Example 2 n-octyloxycarbonylmethyl-(p-chlorobenzoyl)-5-methoxy-2-methylindole-
3-Acetate: Acetacin 2.089% n-octyl alcohol 0.65 f/, DCC 1,039
, cyanomethyl 50m, 4-dimethylaminopyridine 0
．． The mixture of 06f is stirred at room temperature for 15 hours.
反応液を実施例１と同様に処理して黄色油状物１．６８
９（収率６３．６％）を得る。これを酢酸エチル−ｎ−
ヘキサンより結晶化して、融点５６〜５７℃の淡黄色粉
末を得る。The reaction solution was treated in the same manner as in Example 1 to give a yellow oil of 1.68 g.
9 (yield 63.6%). This is ethyl acetate-n-
Crystallization from hexane gives a pale yellow powder with a melting point of 56-57°C.
ＭＳｍ／＊ ： ５２９（Ｍ ｆｏｒ ３７Ｃ１〕、
５２７（Ｍ＋ｆｏｒ ３５Ｃ１） −３１１（Ｍ
−ＣＯＯＣＨ２ＣＯＯ（４Ｈ１７） 。MSm/*: 529 (M for 37C1),
527(M+for 35C1) -311(M
-COOCH2COO (4H17).
１６７０ （ＣＯＮ ） 、 ’ Ｈ−ＮＭＲ（ＣＤＣ
ｌ２）δニア、６７（２Ｈ。1670 (CON), 'H-NMR (CDC
l2) δ near, 67 (2H.
Ｒ′
２．４Ｈｚ、Ｃ４−Ｈ）、６．８８（ＩＨＩｄ、Ｊ＝＝
９．０Ｈｚ、Ｃ７−Ｈ） 、 ６．６７ （ｌ Ｈ、ｄ
、ｄ、、 Ｊｏｒｔｈｏ＝９．０Ｉ（ｓ 、Ｊｍ＠ｔａ
＝２５Ｈｚ 、Ｃ６−Ｈ） 、４．６３（２’Ｈ，ｓ
、０ＣＨＩＣＯＯ） 。R' 2.4Hz, C4-H), 6.88 (IHId, J==
9.0Hz, C7-H), 6.67 (l H, d
,d,, Jortho=9.0I(s, Jm@ta
=25Hz, C6-H), 4.63(2'H,s
,0CHICOO).
４．１４（２ａ、ｉ、、ｙ＝６．６ａｚ、ｏｃＨ，／Ｖ
’／’Ａ ）。4.14 (2a,i,,y=6.6az,ocH,/V
'/'A).
３．８５（３Ｈ１１＊ＯＣ’Ｈ３）Ｃ３，７９（２Ｈ＋
ｌＩＣ５−ＣＨ，）１２．３９ （３Ｈ＊ ｓ ＃
ＣＨ＜Ｈｓ ） ＋ １−２６ （１２Ｈ＊ ｂｒｏａ
ｄｅ。3.85(3H11*OC'H3)C3,79(2H+
lIC5-CH,)12.39 (3H*s #
CH<Hs) + 1-26 (12H* broa
de.
０△（ＣＨｚ）ａ−） 、 ｏ、ｓ ｓ （３Ｈ、ｔ
、 Ｊ＝６．８Ｈｚ 。0△(CHz)a-) , o, s s (3H, t
, J=6.8Hz.
△ハｔシＣＨｓ）
実施例３
セチルオキシカルボニルメチル・１−（ｐ−クロロベン
ゾイル）−５−メトキシ−２−メチルインドール−３−
アセテート：
アセメタシン２．０８ｐ、セチルアルコール１．２１
Ｐ、ＤＣＣ１，０３ｆ、 ４−ジメチルアミノピリジン
０．０６Ｐ、シアノメチル４０−の混液を室温にて１５
時間攪拌する。反応液を実施例１と同様に処理し、得ら
れる油状物を酢酸エチル−鳳−ヘキサンより結晶化して
、融点６８〜６９℃の淡黄色粉末２．ｘｔａｔ（収率６
８．４％）を得る。ΔCHs) Example 3 Cetyloxycarbonylmethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-
Acetate: acemetacin 2.08p, cetyl alcohol 1.21
A mixture of P, DCC 1,03f, 4-dimethylaminopyridine 0.06P, and cyanomethyl 40- was heated to 15% at room temperature.
Stir for an hour. The reaction solution was treated in the same manner as in Example 1, and the resulting oil was crystallized from ethyl acetate-hexane to give a pale yellow powder with a melting point of 68-69°C.2. xtat (yield 6
8.4%).
十
ＭＢｗ／ｅ：６４２［Ｍ ｆｏｒ ｓ７ＣＬ）ｔ６
４０（Ｍｆｏｒ ３５Ｃｔ） 、３１１（Ｍ” −ＣＯ
ＯＣＨ２ＣＯＯＣ１６Ｈ＠＠ ：］ 。10 MBw/e: 642 [M for s7CL) t6
40(Mfor 35Ct), 311(M”-CO
OCH2COOC16H@@:].
（Ｃｏｏ） 、 １６６０ （ＣＯＮ ） 、 Ｉ Ｈ
−ＮＭＲ（ＣＤＣ１ｓ ）δ：５−
２．４Ｈｚ 、Ｃ４−Ｈ） 、 １３．９１ （ＩＨ、
ｄ 、 Ｊ＝９．０１（ｚ 。(Coo), 1660 (CON), IH
-NMR (CDC1s) δ:5-2.4Hz, C4-H), 13.91 (IH,
d, J = 9.01 (z.
Ｃ？−Ｈ） 、 ６．６７ （ＩＨ＋ ｄ、ｄ、、 Ｊ
ｏｒｔｈｅ＝９．０Ｈｚ 。C? -H), 6.67 (IH+ d, d,, J
orthe=9.0Hz.
１ａｚ ｔ ａ ＝２．４ Ｈｚ ＊ Ｃ６−Ｈ） ＋
４−６３ （２Ｈｓ ｓ ＊ ｏｃｔｔ、ｃｏｏ ）
； ４．１３ （２Ｈｙ ｔ ｙ Ｊ＝６．８１１＊
＊ ０ＣＨｊＣ１＠Ｈ３１） 。1az ta = 2.4 Hz * C6-H) +
4-63 (2Hs * octt, coo)
; 4.13 (2Hy t y J=6.811*
*0CHjC1@H31).
３．８４ （３Ｈ−、０ＣＨＢ ）、３．７９ （２Ｈ
＊ Ｉ ＋ Ｃ禽−ＣＨ２）＋２．３９（３Ｈ，諷、Ｃ
クーＣＨｓ） ＋ １．２５ （２８ｎ 、 ｓ 。3.84 (3H-,0CHB), 3.79 (2H
* I + C bird-CH2) + 2.39 (3H, idiom, C
Cu CHs) + 1.25 (28n, s.
（ＣＨｚ）ｔａ） ｅ Ｏ，８８（３Ｈ＋ ｔ ｔ Ｊ
＝＝８．０Ｈｚ 、 （ＣＨｘ）ｔ４ｃＨｓ）以上(CHz) ta) e O, 88 (3H+ t t J
==8.0Hz, (CHx)t4cHs) or more
Claims (1)
ル基を示す） で表わされるインドールアセトキシ酢酸エステル。
、 、 。[Scope of Claims] 1. Indoleacetoxyacetic acid ester represented by the general formula (wherein R represents a linear or branched □ alkyl group of 03 to 01g).
, , .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8286182A JPS58201763A (en) | 1982-05-17 | 1982-05-17 | Indoleacetoxyacetic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8286182A JPS58201763A (en) | 1982-05-17 | 1982-05-17 | Indoleacetoxyacetic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58201763A true JPS58201763A (en) | 1983-11-24 |
| JPH0212221B2 JPH0212221B2 (en) | 1990-03-19 |
Family
ID=13786116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8286182A Granted JPS58201763A (en) | 1982-05-17 | 1982-05-17 | Indoleacetoxyacetic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58201763A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6207700B1 (en) | 1999-01-07 | 2001-03-27 | Vanderbilt University | Amide derivatives for antiangiogenic and/or antitumorigenic use |
| US6306890B1 (en) | 1999-08-30 | 2001-10-23 | Vanderbilt University | Esters derived from indolealkanols and novel amides derived from indolealkylamides that are selective COX-2 inhibitors |
| US6762182B1 (en) | 1999-01-07 | 2004-07-13 | Vanderbilt University | Converting cox inhibition compounds that are not COX-2 selective inhibitors to derivatives that are COX-2 selective inhibitors |
| US7736624B2 (en) | 2006-06-19 | 2010-06-15 | Univ Vanderbilt | Methods and compositions for diagnostic and therapeutic targeting of COX-2 |
| US8168656B2 (en) | 2004-04-26 | 2012-05-01 | Vanderbilt University | Indoleacetic acid and indenacetic acid derivatives as therapeutic agents with reduced gastrointestinal toxicity |
| US9346803B2 (en) | 2011-10-17 | 2016-05-24 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5147708A (en) * | 1974-10-23 | 1976-04-23 | Hitachi Ltd | DENSHANONTEN KAIRO |
| JPS58164570A (en) * | 1982-02-26 | 1983-09-29 | トロポンベルケ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・カンパニ−・コマンジツト・ゲゼルシヤフト | Indole derivative, manufacture and use as drug |
-
1982
- 1982-05-17 JP JP8286182A patent/JPS58201763A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5147708A (en) * | 1974-10-23 | 1976-04-23 | Hitachi Ltd | DENSHANONTEN KAIRO |
| JPS58164570A (en) * | 1982-02-26 | 1983-09-29 | トロポンベルケ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・カンパニ−・コマンジツト・ゲゼルシヤフト | Indole derivative, manufacture and use as drug |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6207700B1 (en) | 1999-01-07 | 2001-03-27 | Vanderbilt University | Amide derivatives for antiangiogenic and/or antitumorigenic use |
| US6399647B2 (en) | 1999-01-07 | 2002-06-04 | Vanderbilt University | Amide derivatives for antiangiogenic and/or antitumorigenic use |
| US6762182B1 (en) | 1999-01-07 | 2004-07-13 | Vanderbilt University | Converting cox inhibition compounds that are not COX-2 selective inhibitors to derivatives that are COX-2 selective inhibitors |
| US6306890B1 (en) | 1999-08-30 | 2001-10-23 | Vanderbilt University | Esters derived from indolealkanols and novel amides derived from indolealkylamides that are selective COX-2 inhibitors |
| US8168656B2 (en) | 2004-04-26 | 2012-05-01 | Vanderbilt University | Indoleacetic acid and indenacetic acid derivatives as therapeutic agents with reduced gastrointestinal toxicity |
| US7736624B2 (en) | 2006-06-19 | 2010-06-15 | Univ Vanderbilt | Methods and compositions for diagnostic and therapeutic targeting of COX-2 |
| US8143302B2 (en) | 2006-06-19 | 2012-03-27 | Vanderbilt University | Methods and compositions for diagnostic and therapeutic targeting of COX-2 |
| US8865130B2 (en) | 2006-06-19 | 2014-10-21 | Vanderbilt University | Methods and compositions for diagnostic and therapeutic targeting of COX-2 |
| US9346803B2 (en) | 2011-10-17 | 2016-05-24 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
| US9895351B2 (en) | 2011-10-17 | 2018-02-20 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
| US10398678B2 (en) | 2011-10-17 | 2019-09-03 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
| US11738004B2 (en) | 2011-10-17 | 2023-08-29 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0212221B2 (en) | 1990-03-19 |
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