JPH0259816B2 - - Google Patents
Info
- Publication number
- JPH0259816B2 JPH0259816B2 JP14544683A JP14544683A JPH0259816B2 JP H0259816 B2 JPH0259816 B2 JP H0259816B2 JP 14544683 A JP14544683 A JP 14544683A JP 14544683 A JP14544683 A JP 14544683A JP H0259816 B2 JPH0259816 B2 JP H0259816B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- examples
- compound
- lower alkoxy
- 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 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 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-butoxy, pentyloxy Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- SWNROPPWBFHVCS-UHFFFAOYSA-N 1,4,5,8-tetramethoxynaphthalene Chemical compound C1=CC(OC)=C2C(OC)=CC=C(OC)C2=C1OC SWNROPPWBFHVCS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は新規なアルコキシナフタレン誘導体に
関する。
本発明のアルコキシナフタレン誘導体は、文献
未載の新規化合物であつて、下記一般式〔１〕で
表わされる。
〔式中、R1は、低級アルコキシ基を、R2はハロ
ゲン原子、低級アルキル基、シアノ基および低級
アルコキシ基からなる群から選択される１〜３個
を有することのあるフエニル基を示す〕
上記一般式〔１〕で表わされる本発明化合物
は、抗炎症作用、抗高血圧作用、抗アレルギー作
用および中枢神経抑制作用を有し、例えば消炎
剤、抗高血圧剤、抗アレルギー剤、分裂病の治療
剤および鎮静剤などの医薬品として有用である。
本明細書において、低級アルコキシ基としては
例えばメトキシ、エトキシ、プロポキシ、イソプ
ロポキシ、ブトキシ、ｔ−ブトキシ、ペンチルオ
キシ、ヘキシルオキシ基などが挙げられる。ハロ
ゲン原子としては、塩素原子、臭素原子、ヨウ素
原子およびフツソ原子が挙げられる。低級アルキ
ル基としては例えばメチル、エチル、プロピル、
イソプロピル、ブチル、ｔ−ブチル、ペンチル、
ヘキシル基などが挙げられる。
本発明の化合物は種々の方法により製造され
る。その好ましい一例を下記反応行程式−１に示
す。
〔各式においてR1およびR2は前記と同じ。Ｘは
ハロゲン原子を示す〕
反応行程式−１によれば、一般式〔１〕で表わ
される本発明化合物は公知の一般式〔２〕の化合
物を、一般式〔３〕の酸ハロゲン化物とフリーデ
ルクラフト反応させてアシル化することにより製
造される。
本反応は通常、溶媒中、触媒の存在下で行なわ
れる。溶媒としては、例えば、ニトロメタン、ニ
トロベンゼン、二硫化炭素、ジクロルメタン、ク
ロロホルム等の一般のフリーデルクラフト反応に
使用される各種のものを例示できる。また触媒と
しては通常のルイス酸触媒例えば塩化アルミニウ
ム、塩化第二スズ、四塩化チタン、三フツ化ホウ
素等を例示できる。これらの触媒は、一般式
〔１〕の化合物に対して通常当モル〜５倍モル程
度使用される。一般式〔３〕の酸ハロゲン化物は
一般式〔１〕の化合物に対して通常当モル〜15倍
モル使用される。反応温度は約０℃〜溶媒の沸点
程度とするのがよい。上記反応の好ましい一例と
しては、ルイス酸として塩化第二スズを用い、溶
媒としてジクロルメタンを使用する方法を例示で
きる。
斯くして生成する本発明化合物は、慣用の分離
手段、例えば溶媒抽出、再結晶、カラムフロマト
グラフイー等により容易に単離精製される。
以下に本発明化合物の製造例を実施例として挙
げる。
実施例 １
１，４，５，８−テトラメトキシナフタレン
6gを、ジクロルメタン250mlに溶解し、塩化ベン
ゾイル21gを加え、さらに塩化第２スズ18gを室
温で加え、混合物を２時間還流する。反応混合物
を水層に移し、ジクロルメタンで抽出する。有機
層を分離し、飽和炭酸水素ナトリウム水で２回洗
浄する。有機層を乾燥（MgSO4）留去して得ら
れた粗生成物を、シリカゲルクロマトグラフイー
（エチルエーテル：ｎ−ヘキサン＝１：１、次い
でジクロルメタン）にて精製して、4.5gの２−ベ
ンゾイル１，４，５，８−テトラメトキシナフタ
レンを油状物として得る。
1H−NMR（CDCl3、TMS）：δppm＝7.90〜
7.93（ｍ、2H）、7.36〜7.84（ｍ、3H）、6.86（Ｓ、
2H）、6.78（Ｓ、1H）、3.90（Ｓ、3H）、3.89（Ｓ、
3H）、3.87（Ｓ、3H）3.64（Ｓ、3H）
実施例 ２〜６
適当な出発原料を用い、実施例１と同様にし
て、下記第１表に示す各化合物を得る。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel alkoxynaphthalene derivatives. The alkoxynaphthalene derivative of the present invention is a novel compound that has not been described in any literature, and is represented by the following general formula [1]. [In the formula, R 1 represents a lower alkoxy group, and R 2 represents a phenyl group that may have 1 to 3 atoms selected from the group consisting of a halogen atom, a lower alkyl group, a cyano group, and a lower alkoxy group] The compound of the present invention represented by the above general formula [1] has an anti-inflammatory effect, an anti-hypertensive effect, an anti-allergic effect, and a central nervous system depressing effect, such as an anti-inflammatory agent, an anti-hypertensive agent, an anti-allergic agent, and a treatment for schizophrenia. It is useful as a medicine, such as a stimulant and a sedative. In this specification, examples of lower alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-butoxy, pentyloxy, and hexyloxy groups. Examples of the halogen atom include a chlorine atom, a bromine atom, an iodine atom, and a fluorine atom. Examples of lower alkyl groups include methyl, ethyl, propyl,
Isopropyl, butyl, t-butyl, pentyl,
Examples include hexyl group. Compounds of the invention are made by a variety of methods. A preferred example thereof is shown in Reaction Scheme-1 below. [In each formula, R 1 and R 2 are the same as above. X represents a halogen atom] According to Reaction Scheme-1, the compound of the present invention represented by the general formula [1] is obtained by combining a known compound of the general formula [2] with an acid halide of the general formula [3] and free Manufactured by acylation through Delkraft reaction. This reaction is usually carried out in a solvent in the presence of a catalyst. Examples of the solvent include various solvents commonly used in Friedel-Crafts reactions, such as nitromethane, nitrobenzene, carbon disulfide, dichloromethane, and chloroform. Examples of catalysts include common Lewis acid catalysts such as aluminum chloride, stannic chloride, titanium tetrachloride, and boron trifluoride. These catalysts are usually used in an amount of about 1 molar to 5 times the molar amount of the compound of general formula [1]. The acid halide of general formula [3] is usually used in a molar equivalent to 15 times the molar amount of the compound of general formula [1]. The reaction temperature is preferably about 0° C. to the boiling point of the solvent. A preferred example of the above reaction is a method in which stannic chloride is used as the Lewis acid and dichloromethane is used as the solvent. The compound of the present invention thus produced can be easily isolated and purified by conventional separation means such as solvent extraction, recrystallization, column chromatography, etc. Examples of the production of the compounds of the present invention are listed below as examples. Example 1 1,4,5,8-tetramethoxynaphthalene
6 g are dissolved in 250 ml of dichloromethane, 21 g of benzoyl chloride are added, a further 18 g of stannic chloride are added at room temperature, and the mixture is refluxed for 2 hours. The reaction mixture is transferred to the aqueous layer and extracted with dichloromethane. Separate the organic layer and wash twice with saturated aqueous sodium bicarbonate. The organic layer was dried (MgSO 4 ) and the resulting crude product was purified by silica gel chromatography (ethyl ether:n-hexane=1:1, then dichloromethane) to obtain 4.5 g of 2- Benzoyl 1,4,5,8-tetramethoxynaphthalene is obtained as an oil. 1H -NMR ( CDCl3 , TMS): δppm=7.90~
7.93 (m, 2H), 7.36-7.84 (m, 3H), 6.86 (S,
2H), 6.78 (S, 1H), 3.90 (S, 3H), 3.89 (S,
3H), 3.87 (S, 3H) 3.64 (S, 3H) Examples 2 to 6 Using appropriate starting materials, each compound shown in Table 1 below is obtained in the same manner as in Example 1. 【table】
Claims (1)
換基としてハロゲン原子、低級アルキル基、シア
ノ基および低級アルコキシ基からなる群から選択
される１〜３個を有することのあるフエニル基を
示す〕 で表わされるアルコキシナフタレン誘導体。[Claims] 1. General formula [In the formula, R 1 is a lower alkoxy group, and R 2 is a phenyl group that may have 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkyl group, a cyano group, and a lower alkoxy group. An alkoxynaphthalene derivative represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14544683A JPS6036436A (en) | 1983-08-08 | 1983-08-08 | Alkoxynaphthalene derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14544683A JPS6036436A (en) | 1983-08-08 | 1983-08-08 | Alkoxynaphthalene derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6036436A JPS6036436A (en) | 1985-02-25 |
| JPH0259816B2 true JPH0259816B2 (en) | 1990-12-13 |
Family
ID=15385410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14544683A Granted JPS6036436A (en) | 1983-08-08 | 1983-08-08 | Alkoxynaphthalene derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6036436A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5026759A (en) * | 1985-05-08 | 1991-06-25 | Du Pont Merck Pharmaceutical | 2-substituted-1-naphthols as 5-lipoxygenase inhibitors |
| CN103833539A (en) * | 2014-01-23 | 2014-06-04 | 上海甘田光学材料有限公司 | Aryl naphthalenylmethanone derivatives and preparation method thereof |
-
1983
- 1983-08-08 JP JP14544683A patent/JPS6036436A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6036436A (en) | 1985-02-25 |
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