JPH0220638B2 - - Google Patents
Info
- Publication number
- JPH0220638B2 JPH0220638B2 JP7417780A JP7417780A JPH0220638B2 JP H0220638 B2 JPH0220638 B2 JP H0220638B2 JP 7417780 A JP7417780 A JP 7417780A JP 7417780 A JP7417780 A JP 7417780A JP H0220638 B2 JPH0220638 B2 JP H0220638B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- general formula
- lower alkyl
- alkyl group
- 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
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- RVSGRNKUJJUAPV-UHFFFAOYSA-N benzo[d][1,2]benzoxazepine Chemical class O1N=CC2=CC=CC=C2C2=CC=CC=C12 RVSGRNKUJJUAPV-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- -1 ethyl -phenyldibenzo[b,f][1,4]oxazepine-8-carboxylate Chemical compound 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
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
【発明の詳細な説明】
本発明は次の一般式
（式中R1は水素原子、低級アルキル基又は低級
アルコキシ基を示し、R2は低級アルコキシカル
ボニル基を示し、R3は低級アルキル基又は置換
基を有し得るフエニル基を示す。）で表わされる
ジベンゾオキサゼピン誘導体に関する。
一般式〔〕で表わされる本発明の化合物は例え
ば、次の一般式
〔〕
（式中R1、R2及びR3は前記と同一の意味を有す
る。）で表わされる化合物を還元することにより
工業的に得ることができる。
還元反応は常法により、例えば、メタノール、
エタノール、ジオキサン、酢酸エチル、テトラヒ
ドロフラン等の溶媒中、５〜10％のラネーニツケ
ル又はパラジウム−カーボン等の触媒の存在下接
触還元することにより行われる。
また、上記に替えて、溶媒中、水素化ホウ素ナ
トリウムのような還元剤を作用させても、同様に
目的物を得ることができる。
ここで用いられる前記一般式〔〕で表わされる
原料化合物も新規物質であるが、例えば、次の一
般式
〔〕
（式中R1、R2及びR3は前記と同一の意味を有す
る。）で表わされる化合物を閉環せしめることに
より容易に得ることができる。閉環反応は、ベン
ゼン、トルエン、クロロホルムのような不活性溶
媒中、オキシ塩化リン、塩化亜鉛等の脱水剤の存
在下、加熱することにより行われる。
かくして得られる本発明の化合物は、脂質低下
作用、血小板凝集抑制作用を有し、医薬として有
用である。
実施例 １
２，４−ジメトキシ−11−フエニルジベンゾ
〔ｂ，ｆ〕〔１，４〕オキサゼピン−８−ウルボン
酸エチル0.6ｇを酢酸エチル20mlに溶解し、パラ
ジウム−カーボン（５％Pd）0.05ｇを加え、水素
気流下撹拌する。反応終了後、反応液を過し、
液を濃縮後、残渣にエタノールを加えて結晶化
させ、これをエタノールから再結晶して、無色針
状の10，11−ジヒドロ−２，４−ジメトキシ−11
−フエニルジベンゾ〔ｂ，ｆ〕〔１，４〕オキサ
ゼピン−８−カルボン酸エチル0.55ｇを得た。収
率91％、融点189.5〜190.5℃。
元素分析値 分子式C24H23NO5として
Ｃ Ｈ Ｎ
理論値(%)68.40 5.50 3.32
実測値(%)68.35 5.48 3.29
実施例 ２
実施例１と同様にして次表の化合物を得た。
【表】[Detailed Description of the Invention] The present invention is based on the following general formula: (In the formula, R 1 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group, R 2 represents a lower alkoxycarbonyl group, and R 3 represents a lower alkyl group or a phenyl group that may have a substituent.) dibenzoxazepine derivatives. The compound of the present invention represented by the general formula [] is, for example, the following general formula [] (In the formula, R 1 , R 2 and R 3 have the same meanings as above.) It can be obtained industrially by reducing the compound represented by the formula. The reduction reaction can be carried out by a conventional method, for example, using methanol,
Catalytic reduction is carried out in a solvent such as ethanol, dioxane, ethyl acetate, or tetrahydrofuran in the presence of a catalyst such as 5 to 10% Raney nickel or palladium-carbon. Furthermore, instead of the above, the desired product can be obtained in the same way by using a reducing agent such as sodium borohydride in a solvent. The raw material compound represented by the above general formula [] used here is also a new substance, but for example, the following general formula [] (In the formula, R 1 , R 2 and R 3 have the same meanings as above.) It can be easily obtained by ring-closing the compound represented by the formula. The ring-closing reaction is carried out by heating in an inert solvent such as benzene, toluene, or chloroform in the presence of a dehydrating agent such as phosphorus oxychloride or zinc chloride. The compound of the present invention thus obtained has lipid-lowering action and platelet aggregation-inhibiting action, and is useful as a medicine. Example 1 0.6 g of ethyl 2,4-dimethoxy-11-phenyldibenzo[b,f][1,4]oxazepine-8-urboxate was dissolved in 20 ml of ethyl acetate, and palladium-carbon (5% Pd) 0.05 g was dissolved in 20 ml of ethyl acetate. g and stirred under a hydrogen stream. After the reaction is complete, filter the reaction solution,
After concentrating the liquid, ethanol was added to the residue to crystallize it, and this was recrystallized from ethanol to give colorless needle-shaped 10,11-dihydro-2,4-dimethoxy-11
0.55 g of ethyl -phenyldibenzo[b,f][1,4]oxazepine-8-carboxylate was obtained. Yield 91%, melting point 189.5-190.5℃. Elemental analysis value Molecular formula C 24 H 23 NO 5 C H N Theoretical value (%) 68.40 5.50 3.32 Actual value (%) 68.35 5.48 3.29 Example 2 The compounds shown in the following table were obtained in the same manner as in Example 1. 【table】
Claims (1)
アルコキシ基を示し、R2は低級アルコキシカル
ボニル基を示し、R3は低級アルキル基又は置換
基を有し得るフエニル基を示す。）で表される化
合物。[Claims] 1. General formula (In the formula, R 1 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group, R 2 represents a lower alkoxycarbonyl group, and R 3 represents a lower alkyl group or a phenyl group that may have a substituent.) compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7417780A JPS572279A (en) | 1980-06-04 | 1980-06-04 | Dibenzoxazepin derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7417780A JPS572279A (en) | 1980-06-04 | 1980-06-04 | Dibenzoxazepin derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS572279A JPS572279A (en) | 1982-01-07 |
| JPH0220638B2 true JPH0220638B2 (en) | 1990-05-10 |
Family
ID=13539615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7417780A Granted JPS572279A (en) | 1980-06-04 | 1980-06-04 | Dibenzoxazepin derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS572279A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4886795A (en) * | 1984-06-20 | 1989-12-12 | Schachar Ronald A | Treatment and prevention of retinal edema with dopaminergic antagonists |
| US4886815A (en) * | 1984-06-20 | 1989-12-12 | Schachar Ronald A | Treatment and prevention of retinal edema with dopaminergic antagonists |
| JPH0754640Y2 (en) * | 1990-09-10 | 1995-12-18 | 謙治 岡安 | Heat driven pump |
| 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 |
-
1980
- 1980-06-04 JP JP7417780A patent/JPS572279A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS572279A (en) | 1982-01-07 |
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