JPS6159314B2 - - Google Patents
Info
- Publication number
- JPS6159314B2 JPS6159314B2 JP53065692A JP6569278A JPS6159314B2 JP S6159314 B2 JPS6159314 B2 JP S6159314B2 JP 53065692 A JP53065692 A JP 53065692A JP 6569278 A JP6569278 A JP 6569278A JP S6159314 B2 JPS6159314 B2 JP S6159314B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- compound
- formula
- dibenzoxepine
- oxepin
- 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
- ZGNHLWKYNFSKCD-UHFFFAOYSA-N Dibenzoxepine Chemical class O1C=CC2=CC=CC=C2C2=CC=CC=C12 ZGNHLWKYNFSKCD-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- -1 cyano compound Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 244000240602 cacao Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Description
本発明は次の一般式（）
で表わされるジベンゾオキセピン誘導体およびそ
の無毒性塩ならびにその製造法に関する。
本発明者は多くのジベンゾオキセピン系化合物
を合成し、その薬理作用を検討していたところ、
上記一般式（）で表わされるジベンゾオキセピ
ン誘導体が卓越した抗炎症作用を有することを見
出し、本発明を完成した。
従つて、本発明は優れた薬理作用を有する一般
式（）で表わされる新規な化合物を提供せんと
するにある。
他の目的は一般式（）の化合物を製造する方
法を提供せんとするにある。
本発明の式（）の化合物は次に示す方法によ
つて製造される。
すなわち、式（）のシアノ化合物を加水分解
することにより、式（）のジベンゾオキセピン
酢酸誘導体を製造する。
この反応は、通常の加水分解、例えば水または
含水有機溶媒中、酸または塩基の存在下３〜10時
間加熱還流することにより行われる。
尚、原料の式（）の化合物は例えば次の如く
して製造される。
（式中、ＸおよびＹは同一または異なつてハロゲ
ン原子を示す）すなわち、２−ハロゲノ−６−フ
エノキシフエニル酢酸を縮合剤と反応せしめるこ
とにより１−ハロゲノ−10・11−ジヒドロ−10−
オキソジベンゾ〔ｂ・ｆ〕オキセピンとなし、次
いで還元して１−ハロゲノ−10・11−ジヒドロジ
ベンゾ〔ｂ・ｆ〕オキセピンとなし、これをシア
ノ化し更に加水分解して、１−カルボキシ−10・
11−ジヒドロジベンゾ〔ｂ・ｆ〕オキセピンとな
し、これを還元し次いでハロゲン化し、更にシア
ノ化することにより、式（）の１−シアノメチ
ル−10・11−ジヒドロジベンゾ〔ｂ・ｆ〕オキセ
ピンを製造する。
本発明化合物の単離、精製は常法により行われ
る。
一般式（）で表わされる本発明化合物は優れ
た抗炎症作用を有する。以下に本発明化合物をカ
ラゲニン浮腫法を用いて検討した薬理結果を、既
知の代表的消炎剤の効果と対比して示す。
すなわち、１群５〜７匹からなる体重約100ｇ
のWister系雄性ラツトに本発明化合物または既
知の代表的消炎剤を経口投与し、１時間後に１％
カラゲニン生理食塩水0.1ml／ラツトを後肢足蹠
皮下に注射し、足蹠容積をVolume differential
meterを用いて経時的に測定した。カラゲニンを
注射してから３時間目の抑制率を表１に示す。
The present invention is based on the following general formula () The present invention relates to a dibenzoxepine derivative represented by the above formula, a non-toxic salt thereof, and a method for producing the same. The present inventor synthesized many dibenzoxepine compounds and investigated their pharmacological effects.
The present invention was completed based on the discovery that the dibenzoxepine derivative represented by the above general formula () has an outstanding anti-inflammatory effect. Therefore, the present invention aims to provide a novel compound represented by the general formula () having excellent pharmacological action. Another object is to provide a method for producing compounds of general formula (). The compound of formula () of the present invention is produced by the method shown below. That is, the dibenzoxepine acetic acid derivative of formula () is produced by hydrolyzing the cyano compound of formula (). This reaction is carried out by conventional hydrolysis, for example, heating under reflux for 3 to 10 hours in water or a water-containing organic solvent in the presence of an acid or base. Incidentally, the compound of formula () as a raw material is produced, for example, as follows. (In the formula, X and Y are the same or different and represent a halogen atom.) That is, by reacting 2-halogeno-6-phenoxyphenylacetic acid with a condensing agent, 1-halogeno-10,11-dihydro-10-
It is converted into oxodibenzo[b・f]oxepin, which is then reduced to 1-halogeno-10,11-dihydrodibenzo[b・f]oxepin, which is cyanated and further hydrolyzed to form 1-carboxy-10,
1-cyanomethyl-10,11-dihydrodibenzo[b/f]oxepin of the formula () is produced by reducing this, followed by halogenation, and further cyanation. do. Isolation and purification of the compounds of the present invention are carried out by conventional methods. The compound of the present invention represented by the general formula () has an excellent anti-inflammatory effect. The pharmacological results of the compound of the present invention examined using the carrageenan edema method are shown below in comparison with the effects of known representative anti-inflammatory agents. In other words, each group consists of 5 to 7 animals, weighing approximately 100g.
The compound of the present invention or a known typical anti-inflammatory agent was orally administered to Wistar male rats, and 1 hour later, 1%
Carrageenin saline (0.1 ml/rat) was injected subcutaneously into the hind foot pad, and the volume differential was measured.
It was measured over time using a meter. Table 1 shows the inhibition rate 3 hours after carrageenan injection.
【表】
本発明化合物：（10・11−ジヒドロジベンゾ
〔ｂ・ｆ〕オキセピン−１−イル）酢酸
本発明の化合物は医薬として用いる場合には、
それ自体あるいはその塩の形で使用できる。塩と
しては、ナトリウム、カリウム、カルシウム、ア
ルミニウムのような無毒性塩とするのが好まし
い。
本発明の化合物は、経口投与、非経口投与のい
ずれにおいても作用を発揮し、経口、注射、経直
腸、局所投与用の剤型にすることができる。
経口投与用の固体剤型としては、カプセル、錠
剤、丸剤、粉末剤、顆粒剤がある。これらの剤型
の場合の添加剤としては、白糖、乳糖、澱粉等の
賦形剤の他にステアリン酸マグネシウムのような
滑沢剤を使用することができる。また、腸溶性、
徐放性を持つた剤型にすることもできる。
経口投与用の液体剤型としては、乳化剤、溶液
剤、懸濁剤、シロツプ剤、エリキシル剤等があ
る。これらの剤型の場合の添加剤としては、精製
水、アルコール類等の溶剤の他に、湿潤剤、乳化
剤、懸濁剤等の補助剤を加えることができる。
本発明化合物の非経口投与用製剤としては注射
剤、坐剤等がある。注射剤の場合には殺菌した水
性または非水性溶液にすることができる。溶剤の
例としては、プロピレングリコール、ポリエチレ
ングリコール、植物油、有機酸エステル等が挙げ
られる。また、粉末充填の形にして、使用前に溶
剤に溶かすことのできる剤型にしてもよい。坐剤
の場合にはココア、バターあるいは坐薬用ワツク
スのような賦形剤を加える。
本発明の化合物の投与量は、症状、投与経路、
投与期間等によつて異なるが、一般的には、人間
の場合、１日20〜1000mgが好適である。
次に実施例を挙げて本発明を詳細に説明する。
実施例 １
（10・11−ジヒドロジベンゾ〔ｂ・ｆ〕オキセ
ピン−１−イル）酢酸：
１−シアノメチル−10・11−ジヒドロジベンゾ
〔ｂ・ｆ〕オキセピン190mgをエタノール２mlに溶
解し、水酸化ナトリウム200mgを水２mlに溶解し
て加え、撹拌下３時間加熱還流した。反応後、エ
タノールを留去し、塩酸酸性として酢酸エチルに
て抽出し、飽和食塩水で洗浄後、無水硫酸ナトリ
ウムで乾燥した。溶媒を留去して淡黄色油状物を
得、シリカゲル６ｇを用いてカラムクロマトグラ
フイーに付し、クロロホルムにて溶出し、さらに
ベンゼン−ｎ−ヘキサンの混合溶媒より再結晶し
て、融点135.5〜136℃の（10・11−ジヒドロジベ
ンゾ〔ｂ・ｆ〕オキセピン−１−イル）酢酸の無
色結晶113mg（収率55％）を得た。
IRνＫＢｒ ｎａｘcm-1：1700（Ｃ＝０）
NMR（CDCI3）δ：3.09（4H、ｓ、ＣH2 ＣH2 ）
3.63（2H、ｓ、ＣH2 CO−）
6.84〜7.22（7H、ｍ、芳香族プロトン）
8.66（1H、broad ｓ、COOＨ）
MS ｍ／ｅ ：254（M+）[Table] Compound of the present invention: (10,11-dihydrodibenzo[b·f]oxepin-1-yl)acetic acid When the compound of the present invention is used as a medicine,
It can be used by itself or in the form of its salts. The salt is preferably a non-toxic salt such as sodium, potassium, calcium or aluminum. The compound of the present invention exerts its action in both oral and parenteral administration, and can be formulated into dosage forms for oral, injection, rectal, and topical administration. Solid dosage forms for oral administration include capsules, tablets, pills, powders, and granules. As additives for these dosage forms, in addition to excipients such as white sugar, lactose, and starch, a lubricant such as magnesium stearate can be used. Also enteric coated,
It can also be made into a dosage form with sustained release properties. Liquid dosage forms for oral administration include emulsions, solutions, suspensions, syrups, elixirs, and the like. As additives for these dosage forms, in addition to solvents such as purified water and alcohols, auxiliary agents such as wetting agents, emulsifiers, and suspending agents can be added. Preparations for parenteral administration of the compound of the present invention include injections, suppositories, and the like. In the case of injections, it can be a sterile aqueous or non-aqueous solution. Examples of the solvent include propylene glycol, polyethylene glycol, vegetable oil, organic acid ester, and the like. It may also be in the form of a powder filling, which can be dissolved in a solvent before use. In the case of suppositories, excipients such as cocoa, butter or suppository wax are added. The dosage of the compounds of the invention depends on the symptoms, route of administration,
Although it varies depending on the administration period etc., in general, 20 to 1000 mg per day is suitable for humans. Next, the present invention will be explained in detail with reference to Examples. Example 1 (10,11-dihydrodibenzo[b/f]oxepin-1-yl)acetic acid: 190 mg of 1-cyanomethyl-10,11-dihydrodibenzo[b/f]oxepin was dissolved in 2 ml of ethanol, and sodium hydroxide was added. A solution of 200 mg in 2 ml of water was added, and the mixture was heated under reflux for 3 hours with stirring. After the reaction, ethanol was distilled off, acidified with hydrochloric acid, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a pale yellow oil, which was subjected to column chromatography using 6 g of silica gel, eluted with chloroform, and further recrystallized from a mixed solvent of benzene-n-hexane, with a melting point of 135.5 ~ 113 mg (yield 55%) of colorless crystals of (10·11-dihydrodibenzo[b·f]oxepin-1-yl)acetic acid at 136°C were obtained. IRν KBr nax cm -1 : 1700 (C=0) NMR (CDCI 3 ) δ: 3.09 (4H, s, C H 2 C H 2 ) 3.63 (2H, s, C H 2 CO−) 6.84-7.22 (7H , m, aromatic proton) 8.66 (1H, broad s, COO H ) MS m/e: 254 (M + )
Claims (1)
の無毒性塩。 ２ 式 で表わされるシアノ化合物を加水分解することを
特徴とする式 で表わされるジベンゾオキセピン誘導体の製法。[Claims] 1. General formula Dibenzoxepine derivatives represented by and non-toxic salts thereof. 2 formulas A formula characterized by hydrolyzing a cyano compound represented by A method for producing a dibenzoxepine derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6569278A JPS54157582A (en) | 1978-06-02 | 1978-06-02 | Dibenzoxepin derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6569278A JPS54157582A (en) | 1978-06-02 | 1978-06-02 | Dibenzoxepin derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54157582A JPS54157582A (en) | 1979-12-12 |
| JPS6159314B2 true JPS6159314B2 (en) | 1986-12-16 |
Family
ID=13294313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6569278A Granted JPS54157582A (en) | 1978-06-02 | 1978-06-02 | Dibenzoxepin derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54157582A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6019310A (en) * | 1983-07-13 | 1985-01-31 | Nec Corp | High frequency power control circuit |
-
1978
- 1978-06-02 JP JP6569278A patent/JPS54157582A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6019310A (en) * | 1983-07-13 | 1985-01-31 | Nec Corp | High frequency power control circuit |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54157582A (en) | 1979-12-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4585788A (en) | 6,11-dihydrodibenz[b,e]oxepin-acetic acids and derivatives | |
| JPS6159313B2 (en) | ||
| US4247706A (en) | Dibenzothiepin derivatives and a process for producing the same | |
| US3780061A (en) | Tricyclic ketonic compounds | |
| JPH054383B2 (en) | ||
| JPH0433793B2 (en) | ||
| JPH0118899B2 (en) | ||
| JPS6332786B2 (en) | ||
| US4515946A (en) | 6,11-Dihydro-11-oxo-dibenz-[b,e]oxepin derivatives | |
| US4035509A (en) | Methods and compositions for the use of 2-carboxy-5-oxo-5H-dibenzo[a,d]cycloheptenes, salts and esters thereof | |
| JP2873599B2 (en) | Novel benzofuran derivative, uric acid excreting agent and method for producing the same | |
| JPS6159314B2 (en) | ||
| DK159110B (en) | 4H-BENZO (4,5) CYCLOHEPTA (1,2-B) THIOPHENDER DERIVATIVES, PROCEDURES FOR PREPARING IT, AND PHARMACEUTICAL PREPARATIONS CONTAINING THE DERIVATIVES | |
| JPH0436156B2 (en) | ||
| JPH0710863B2 (en) | Novel derivative of 4-OH quinolinecarboxylic acid substituted at position 2 with an etherifiable or esterifiable dihydroxy group, a process for its preparation and its use as a medicament | |
| EP0011282B1 (en) | Thienylbenzoic-acid derivatives, process for their production, and pharmaceutical preparations containing these compounds | |
| KR920006785B1 (en) | Anti-inflammatory 1-heteroaryl-3-acyl-2-oxindoles | |
| IL34468A (en) | Acid addition salts of indenopyridine derivatives,their preparation and pharmaceutical compositions containing them | |
| JPS6111232B2 (en) | ||
| BE893835A (en) | THIAZOLO (3,2, -A) SUBSTITUTED PYRIMIDINES AND PROCESS FOR THEIR PREPARATION | |
| KR100246821B1 (en) | A thiapentarene carboxylate derivative as non-steroid anti-inflammatory agent | |
| JPS6141359B2 (en) | ||
| JPS59186962A (en) | Imidazoline derivative and medicine | |
| JPH0422912B2 (en) | ||
| JPS6130669B2 (en) |