JPH0359067B2 - - Google Patents
Info
- Publication number
- JPH0359067B2 JPH0359067B2 JP10851582A JP10851582A JPH0359067B2 JP H0359067 B2 JPH0359067 B2 JP H0359067B2 JP 10851582 A JP10851582 A JP 10851582A JP 10851582 A JP10851582 A JP 10851582A JP H0359067 B2 JPH0359067 B2 JP H0359067B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- lower alkyl
- hydrogen atom
- reaction
- 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
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明は次の一般式
（式中R1は水素原子又は１〜２個の低級アルキ
ル基或は低級アルコキシ基を意味し、R2は低級
アルキル基、低級アルケニル基又はアラルキル基
を意味し、R3は水素原子又は低級アルキル基を
意味する）
で表わされるジベンゾオキサゼピノン誘導体に関
する。
上式で表わされる本発明の化合物は、例えば、
一般式
（式中R1及びR3は前記と同一の意味を有する）
で表わされるジベンゾオキサゼピノンカルボン酸
エステルと一般式
R2X 〔〕
（式中R2は前記と同一の意味を有し、Ｘはハロ
ゲン原子を示す）
で表わされる化合物とを反応せしめ、必要に応じ
て加水分解することにより容易に得られる。
反応はアセトン、ベンゼン、ジオキサン、Ｎ，
Ｎ−ジメチルホルムアミド等の反応に関与しない
溶媒中で、塩基の存在下、好ましくは50〜200℃
に加熱することによつて行われる。
反応後、必要に応じてエステルの加水分解が行
われる。
加水分解反応は、常法により、例えば水酸化ナ
トリウム又は水酸化カリウム等のアルカリの存在
下エタノール−水混合溶媒中30分〜数時間加熱還
流することによつて行われる。
かくして得られる本発明の化合物は、抗潰瘍作
用を有し、医薬として有用である。
実施例 １
２，４−ジイソプロピル−８−エトキシカルボ
ニルジベンゾ〔ｂ、ｆ〕〔１，４〕オキサゼピン
−11（10H）をオン５ｇをアセトン150mlに溶解
し、これにヨードメチル3.86ｇと炭酸カリウム
5.63ｇを添加し30時間撹拌加熱還流後冷却し無機
物を去し、溶媒を留去して、残渣をベンゼンに
て抽出し、抽出液を水洗し芒硝乾燥後ベンゼンを
留去して２，４−ジイソプロピル−８−エトキシ
カルボニル−10−メチルベンゾ〔ｂ、ｆ〕〔１，
４〕オキサゼピン−11（10H）オンを4.5ｇ得た。
収率86％。希エタノールから再結晶し融点79〜81
℃。
元素分析値 分子式C23H27O4Nとして
Ｃ Ｈ Ｎ
理論値（％） 72.42 7.13 3.67
実測値（％） 72.40 7.09 3.64
実施例 ２〜８
上記と同様にして表の化合物を得た。
The present invention is based on the following general formula (In the formula, R 1 means a hydrogen atom or 1 to 2 lower alkyl groups or lower alkoxy groups, R 2 means a lower alkyl group, lower alkenyl group, or aralkyl group, and R 3 means a hydrogen atom or a lower Refers to a dibenzoxazepinone derivative represented by (meaning an alkyl group). The compound of the present invention represented by the above formula is, for example, the general formula (In the formula, R 1 and R 3 have the same meaning as above) and the dibenzoxazepinone carboxylic acid ester represented by the general formula R 2 X [ ] (In the formula, R 2 has the same meaning as above, (X represents a halogen atom) and can be easily obtained by reacting with a compound represented by the formula (X represents a halogen atom) and, if necessary, hydrolyzing. The reaction is acetone, benzene, dioxane, N,
In a solvent that does not participate in the reaction such as N-dimethylformamide, in the presence of a base, preferably at 50 to 200°C.
This is done by heating to. After the reaction, the ester is hydrolyzed if necessary. The hydrolysis reaction is carried out by a conventional method, for example, by heating under reflux for 30 minutes to several hours in an ethanol-water mixed solvent in the presence of an alkali such as sodium hydroxide or potassium hydroxide. The thus obtained compound of the present invention has antiulcer activity and is useful as a medicine. Example 1 Dissolve 5 g of 2,4-diisopropyl-8-ethoxycarbonyldibenzo[b,f][1,4]oxazepine-11 (10H) in 150 ml of acetone, and add 3.86 g of iodomethyl and potassium carbonate to this.
5.63 g was added, stirred for 30 hours, heated under reflux, cooled, the inorganic matter was removed, the solvent was distilled off, the residue was extracted with benzene, the extract was washed with water, and after drying with sodium sulfate, the benzene was distilled off. -diisopropyl-8-ethoxycarbonyl-10-methylbenzo[b,f][1,
4] 4.5 g of oxazepine-11(10H)one was obtained.
Yield 86%. Recrystallized from dilute ethanol, melting point 79-81
℃. Elemental analysis value Molecular formula C 23 H 27 O 4 N C H N Theoretical value (%) 72.42 7.13 3.67 Actual value (%) 72.40 7.09 3.64 Examples 2 to 8 The compounds shown in the table were obtained in the same manner as above.
【表】【table】
【表】
実施例 ９
２，４−ジイソプロピル−８−エトキシカルボ
ニル−10−メチルベンゾ〔ｂ、ｆ〕〔１，４〕オ
キサゼピン−11（10H）オン５ｇをエタノール50
mlに溶解し、これに10％NaOH50mlを加え２時
間還流する。反応後、エタノール減圧下留去し塩
酸酸性とし析出する結晶を取し、水洗後乾燥し
て８−カルボキシ−２，４−ジイソプロピル−10
−メチルベンゾ〔ｂ、ｆ〕〔１，４〕オキサゼピ
ン−11（10H）オンを4.3ｇ得る。収率92％。ベン
ゼン−ｎ−ヘキサンから再結晶し融点204℃。
元素分析値 分子式C21H23O4Nとして
Ｃ Ｈ Ｎ
理論値（％） 71.31 6.56 3.96
実測値（％） 71.11 6.55 3.94
実施例 10〜16
上記と同様にして表の化合物を得た。[Table] Example 9 5 g of 2,4-diisopropyl-8-ethoxycarbonyl-10-methylbenzo[b,f][1,4]oxazepine-11(10H)one was added to 50 ml of ethanol.
ml, add 50 ml of 10% NaOH, and reflux for 2 hours. After the reaction, ethanol was distilled off under reduced pressure, acidified with hydrochloric acid, and the precipitated crystals were collected, washed with water and dried to give 8-carboxy-2,4-diisopropyl-10
-4.3 g of methylbenzo[b,f][1,4]oxazepine-11(10H)one are obtained. Yield 92%. Recrystallized from benzene-n-hexane, melting point 204°C. Elemental analysis value Molecular formula C 21 H 23 O 4 N C H N Theoretical value (%) 71.31 6.56 3.96 Actual value (%) 71.11 6.55 3.94 Examples 10 to 16 The compounds shown in the table were obtained in the same manner as above.
【表】【table】
Claims (1)
ル基或は低級アルコキシ基を意味し、R2は低級
アルキル基、低級アルケニル基又はアラルキル基
を意味しR3は水素原子又は低級アルキル基を意
味する） で表わされる化合物。[Claims] 1. General formula (In the formula, R 1 means a hydrogen atom or 1 to 2 lower alkyl groups or lower alkoxy groups, R 2 means a lower alkyl group, lower alkenyl group, or aralkyl group, and R 3 means a hydrogen atom or lower alkyl group. A compound represented by (meaning a group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10851582A JPS58225073A (en) | 1982-06-25 | 1982-06-25 | Dibenzoxazepinone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10851582A JPS58225073A (en) | 1982-06-25 | 1982-06-25 | Dibenzoxazepinone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58225073A JPS58225073A (en) | 1983-12-27 |
| JPH0359067B2 true JPH0359067B2 (en) | 1991-09-09 |
Family
ID=14486740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10851582A Granted JPS58225073A (en) | 1982-06-25 | 1982-06-25 | Dibenzoxazepinone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58225073A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10242488A1 (en) * | 2002-09-13 | 2004-03-25 | Bayer Ag | New N-alkyl-dibenzoxazepinone derivatives, are aminopeptidase N inhibitors useful for treating cardiovascular, inflammatory, autoimmune or cancer diseases or chronic pain, especially arteriosclerosis |
| WO2019173761A1 (en) | 2018-03-09 | 2019-09-12 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | C-abl tyrosine kinase inhibitory compound embodiments and methods of making and using the same |
-
1982
- 1982-06-25 JP JP10851582A patent/JPS58225073A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58225073A (en) | 1983-12-27 |
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