JPS602309B2 - Manufacturing method of dibenzoxepines - Google Patents
Manufacturing method of dibenzoxepinesInfo
- Publication number
- JPS602309B2 JPS602309B2 JP11422274A JP11422274A JPS602309B2 JP S602309 B2 JPS602309 B2 JP S602309B2 JP 11422274 A JP11422274 A JP 11422274A JP 11422274 A JP11422274 A JP 11422274A JP S602309 B2 JPS602309 B2 JP S602309B2
- Authority
- JP
- Japan
- Prior art keywords
- oxodibenzo
- dihydro
- oxepinyl
- formaldehyde
- dibenzoxepines
- 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
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は新規なジベンゾオキセピン類の製法に関し、反
応式を示せば次の如くである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing dibenzoxepines, and the reaction formula is as follows.
（式中Ｒはアルキル基を示し、Ｚは水素原子、金属原子
又は有機塩残基を示す。(In the formula, R represents an alkyl group, and Z represents a hydrogen atom, a metal atom, or an organic salt residue.
）即ち、６，１１−ジヒドロー１１−オキソジベンゾ〔
ｂ，ｅ〕オキセピニルホルムアルデヒド（１）にホルム
アルデヒドジアルキルメルカブタールーＳ−オキシドを
作用させ、１ーアルキルスルフイニルー１ーアルキルチ
オー２−（６，１１ージヒドロー１１−オキソジベンゾ
〔ｂ，ｅ〕オキセピニル）エチレン（ロ）となし、これ
を加水分解して６一１１ージヒドロー１１ーオキソジベ
ンゾ〔ｂ，ｅ〕オキセピニル酢酸（ｍ）を製する方法で
ある。), that is, 6,11-dihydro-11-oxodibenzo [
b, e] Oxepinyl formaldehyde (1) is reacted with formaldehyde dialkylmercabutal-S-oxide to form 1-alkylsulfinyl-1-alkylthio 2-(6,11-dihydro 11-oxodibenzo[b,e]oxepinyl ) and hydrolyzing this to produce 6-11-dihydro-11-oxodibenzo[b,e]oxepinyl acetic acid (m).
縮合反応は、適当な溶媒例えばテトラヒドロフラン、ジ
グラィム、ジオキサン等中で塩基性触媒存在下行なうの
が適している。The condensation reaction is suitably carried out in a suitable solvent such as tetrahydrofuran, diglyme, dioxane, etc. in the presence of a basic catalyst.
得られる縮合物（Ｄ）は単機できるが、単離せずに次の
反応に用いることもできる。加水分解は、通常用いられ
る方法により行なわれ、例えば水溶媒中酸、例えば塩酸
、硫酸等と処理すれば容易に進行する。The resulting condensate (D) can be used alone, but it can also be used in the next reaction without isolation. Hydrolysis can be carried out by a commonly used method, and can easily proceed by treatment with an acid such as hydrochloric acid or sulfuric acid in an aqueous medium.
なお、原料化合物（１）は新規物質であるが、対応する
アルコールの酸化等の方法によって製造し得る。Although the raw material compound (1) is a new substance, it can be produced by a method such as oxidation of the corresponding alcohol.
このようにして得られた本発明の目的化合物は強力な抗
炎症、鎮痛、下熱、血小板凝集阻害作用等のすぐれた薬
理学的特性を有し、かつ毒性の低い有用な物質である。The object compound of the present invention thus obtained is a useful substance with excellent pharmacological properties such as strong anti-inflammatory, analgesic, hypopyretic and platelet aggregation inhibiting effects, and low toxicity.
本発明の代表的化合物をあげ、公知薬物との効果を対比
すれば下記の通りである。抗炎症作用（ラットーヵラゲ
ーニン足藤浮腫法）鎮痛作用（ラット Ｒａｎｄａ！１
−Ｓｅｌｌｉｔｔｏ法）※炎症足におりる効果経口急性
毒性（ラット）
実施例 １
２５０のｏの（６，１１ージヒドロー１１ーオキソジベ
ンゾ〔ｂ，ｅ〕オキセピン−３−イル）ホルムアルデヒ
ドをペンジルトリメチルアンモニウムハイドロオキシド
０．０７肌、ホルムアルデヒドジメチルメルカプタール
ーＳ−オキシド７０の９及びテトラハイドロフラン１地
と共に４虫時間加熱還流下縮合させる。Representative compounds of the present invention are listed below and their effects compared with known drugs are as follows. Anti-inflammatory effect (Rat carrageenin foot edema method) Analgesic effect (Rat Randa!1
-Sellitto method) *Effect on inflamed paw Oral acute toxicity (rat) Example 1 250 o of (6,11-dihydro-11-oxodibenzo[b,e]oxepin-3-yl)formaldehyde was mixed with penzyltrimethylammonium hydroxide. 0.07, formaldehyde dimethyl mercaptal, 70 parts of S-oxide, and 1 part of tetrahydrofuran were condensed under heating under reflux for 4 hours.
反応後、反応液をシリカゲルクロマトグラフィーに付し
、ベンゼンーリグロィンで溶離し、所望のフラクション
を集め、溶剤を留去し、黄色油状物の１−メチルスルフ
ィニル−１ーメチルチオー２一〔３一（６，１１ージヒ
ドロ−１１−オキソジベンゾ〔ｂ，ｅ〕オキセピニル〕
ーエチレンが得られる。Ｎ．Ｍ．Ｒ．（Ｓｏｌｖ．ＣＣ
１４，ｐｐｍｈｏｍＴ．Ｍ．Ｓ．）２．３本ｐｍ，が，
ｓ，Ｓ‐９２２．粉ｐｐｍ，９日，ｓ，ＳＯ−ＣＨ３
５．１４ｐｐｍ，２日，ｓ，Ｃ６′一日２６．５２Ｐｐ
ｍ，ＩＨ，ｓ，Ｃ２−日
７．７皿ｐｍ，ＩＨ，ｍ，Ｃ，。After the reaction, the reaction solution was subjected to silica gel chromatography, eluted with benzene-ligroin, the desired fractions were collected, and the solvent was distilled off to obtain 1-methylsulfinyl-1-methylthio 2-[3- (6,11-dihydro-11-oxodibenzo[b,e]oxepinyl]
- Ethylene is obtained. N. M. R. (Solv.CC
14, ppmhomT. M. S. ) 2.3 pm, but,
s, S-922. Powder ppm, 9 days, s, SO-CH3 5.14 ppm, 2 days, s, C6' 26.52 Pp per day
m, IH, s, C2-day 7.7 dishes pm, IH, m, C,.
′一日８．１沙ｐｍ，ＩＨ，ｄ，Ｃ，′一日
このものをテトラハイドロフラン１机と濃塩酸１の‘と
共に１．鼠時間加熱還流後クロロホルム−水で分配、ク
ｏロホルム層を分取、水洗、乾燥後濃縮して６，１１ー
ジヒドロ−１１−オキソジベンゾ〔ｂ，ｅ〕オキセピン
−３一酢酸を得る。'8.1 spm, IH, d, C, '1 day for 1 day. After heating under reflux for an hour, the mixture was partitioned between chloroform and water, and the chloroform layer was separated, washed with water, dried, and concentrated to obtain 6,11-dihydro-11-oxodibenzo[b,e]oxepine-3-monoacetic acid.
Claims (1)
チオ−２−（６，１１−ジヒドロ−１１−オキソジベン
ゾ〔ｂ，ｅ〕オキセピニル）エチレンを加水分解するこ
とを特徴とする６，１１−ジヒドロ−１１−オキソジベ
ンゾ〔ｂ，ｅ〕オキセピニル酢酸若しくはそのエステル
又はその塩の製法。 ２ ６，１１−ジヒドロ−１１−オキソジベンゾ〔ｂ，
ｅ〕オキセピニルホルムアルデヒドにホルムアルデヒド
低級アルキルメルカプタール−Ｓ−オキシドを縮合させ
、次いで得られた１−低級アルキルスルフイニル−１−
低級アルキルチオ−２−（６，１１−ジヒドロ−１１−
オキソジベンゾ〔ｂ，ｅ〕オキセピニル）エチレンを加
水分解することを特徴とする６，１１−ジヒドロ−１１
−オキソジベンゾ〔ｂ，ｅ〕オキセピニル酢酸若しくは
そのエステル又はその塩の製法。[Claims] 1. Characterized by hydrolyzing 1-lower alkylsulfinyl-1-lower alkylthio-2-(6,11-dihydro-11-oxodibenzo[b,e]oxepinyl)ethylene A method for producing 6,11-dihydro-11-oxodibenzo[b,e]oxepinyl acetic acid, its ester, or its salt. 2 6,11-dihydro-11-oxodibenzo [b,
e] Oxepinyl formaldehyde is condensed with formaldehyde lower alkyl mercaptal-S-oxide, and then the obtained 1-lower alkylsulfinyl-1-
Lower alkylthio-2-(6,11-dihydro-11-
6,11-dihydro-11 characterized by hydrolyzing oxodibenzo[b,e]oxepinyl)ethylene
- A method for producing oxodibenzo[b,e]oxepinyl acetic acid or its ester or its salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11422274A JPS602309B2 (en) | 1974-10-03 | 1974-10-03 | Manufacturing method of dibenzoxepines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11422274A JPS602309B2 (en) | 1974-10-03 | 1974-10-03 | Manufacturing method of dibenzoxepines |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1199582A Division JPS603394B2 (en) | 1982-01-28 | 1982-01-28 | Manufacturing method of dibenzoxepines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5141374A JPS5141374A (en) | 1976-04-07 |
| JPS602309B2 true JPS602309B2 (en) | 1985-01-21 |
Family
ID=14632277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11422274A Expired JPS602309B2 (en) | 1974-10-03 | 1974-10-03 | Manufacturing method of dibenzoxepines |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS602309B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11578641B2 (en) | 2018-03-14 | 2023-02-14 | Scania Cv Ab | Thermostat device for a cooling system and a cooling system comprising said thermostat device |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2641810B2 (en) * | 1991-05-02 | 1997-08-20 | 三菱鉛筆株式会社 | Non-fired colored pencil lead and its manufacturing method |
-
1974
- 1974-10-03 JP JP11422274A patent/JPS602309B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11578641B2 (en) | 2018-03-14 | 2023-02-14 | Scania Cv Ab | Thermostat device for a cooling system and a cooling system comprising said thermostat device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5141374A (en) | 1976-04-07 |
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