JPH0458467B2 - - Google Patents
Info
- Publication number
- JPH0458467B2 JPH0458467B2 JP12308384A JP12308384A JPH0458467B2 JP H0458467 B2 JPH0458467 B2 JP H0458467B2 JP 12308384 A JP12308384 A JP 12308384A JP 12308384 A JP12308384 A JP 12308384A JP H0458467 B2 JPH0458467 B2 JP H0458467B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- methanol
- alcohol
- solution
- under reduced
- 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
- 150000003839 salts Chemical class 0.000 claims description 5
- -1 3,6-dihydroxy-3-methoxycarbonyl-3,4-dihydro-2(1H)-quinolone Chemical compound 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 241000209094 Oryza Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 239000000043 antiallergic agent Substances 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
- 229940121354 immunomodulator Drugs 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
産業上の利用分野
本発明は免疫調節作用、抗アレルギー作用及び
消炎鎮痛作用を有する新規２（1H）−キノロン誘
導体に関し、さらに詳しくは３，６−ジヒドロキ
シ−３−メトキシカルボニル−３，４−ジヒドロ
−２（1H）−キノロン（以下、化合物〔〕と称
する）及びその塩に係る。
発明の目的
本発明の目的は免疫調節剤、抗アレルギー剤及
び消炎鎮痛剤の有効成分となり得る化合物〔Ｉ〕
とその塩を提供することにある。
発明の構成
本発明の化合物〔〕は上記の化合構造式を有
し、その３位及び／又は６位のヒドロキシル基
に、医薬上許容される強塩基性化合物、例えば水
酸化ナトリウム、水酸化カリウム、水酸化カルシ
ウムなどを作用させることにより、化合物〔〕
の塩を容易に得ることができる。本発明の化合物
〔〕及びその塩は、免疫調節作用、抗アレルギ
ー作用及び消炎鎮痛作用を有し、従つて、免疫調
節剤、抗アレルギー剤及び消炎鎮痛剤の薬効成分
として極めて有用である。
尚、本発明の化合物〔〕は、そのラセミ体及
び光学異性体をも包含する。
本発明の化合物〔〕は、例えば米糖より容易
に単離することができる。単離手段としては、溶
媒抽出、カラムクロマトグラフイー、薄層クロマ
トグラフイーなどの公知の分離方法が採用され
る。米糖から化合物〔〕を単離する方法の一例
を述べれば、望ましくは乾燥状態にある米糖を、
メタノール、エタノール、イソプロパノールなど
の低級アルコールに常温乃至50℃で浸漬してアル
コール可溶分を米糖から抽出し、第１次抽出液を
得る。この第１次抽出液に必要ならば低級アルコ
ールを加え、さらに疎水性溶媒（例えばｎ−ヘキ
サン）と水を加えて充分に混合し、混合液を静置
するか遠心分離にかけることによつて分層させ、
低級アルコールを含有し、脂質を含まない水溶液
を分取する。次にこの水溶液を減圧濃縮又は減圧
乾固した後、改めて低級アルコールを加えてアル
コール可溶物をこれに溶解させ、アルコール不溶
物（糖質）をアルコール溶液から除去して第２次
抽出液を得る。
こうして得た第２次抽出液を望ましくは減圧濃
縮した後、これに低級アルコールとクロロホルム
の混合液を添加して混合し、生成するタール様物
質を沈降させて上澄液を採取する。次いでこの上
澄液を減圧乾固させて得られる物質を低級アルコ
ールに溶解し、そのアルコール溶液をカラムクロ
マトグラフイー又は薄膜クロマトグラフイーにか
けることにより、目的物たる化合物〔〕を単離
することができる。
カラムクロマトグラフイーの担体には、例えば
シリカゲル、活性アルミナ、硝酸銀シリカゲルな
どが使用可能であり、溶離剤としては、例えばｎ
−ヘキサン、ベンゼン、ジエチルエーテル、クロ
ロホルム、酢酸エチル、アセトン、メタノール、
エタノール及びこれらの混合物が使用可能であ
る。
以下、実施例を掲げて本発明をさらに説明す
る。
実施例
乾燥した米糖10Kgを40℃に加温したメタノール
50に１時間浸漬して抽出を行ない、得られた第
１次抽出液を減圧下に５まで濃縮する。この濃
縮液にｎ−ヘキサン10及び水10を加えて40℃
で振りまぜた後、これを静置すると、メタノール
を含む水性溶液が下層に分離されるので、これを
分液して水性溶液を得る。次にこの水性溶液を減
圧下に蒸発乾固し、乾固物に純メタノール５を
加えて糖質を析出させ、析出物を濾過で除去する
ことにより、メタノール溶液（第２次抽出液）を
得る。このメタノール溶液を蒸発乾固した後、メ
タノール・クロロホルム混合溶液（容積比２：
８）５を加え、生成するタール様物質を沈降さ
せ、上澄液を分離する。次いで、この上澄液を蒸
発乾固してから改めてこれにメタノールを加え、
メタノール溶液を調製する。
他方、メルク社製のKieselgel 60Gで厚さ0.5mm
の薄層を作り、120℃で１時間これを活性化させ
る。この薄層に、先に調製したメタノール溶液を
線状にスポツトし、メタメール・クロロホルム混
合溶媒（容積比１：９）で10cm展開させ、Rf値
＝0.26の部分を集めてメタノールで抽出する。し
かる後、このメタノールを抽出液からメタノール
を留去することにより、３，６−ジヒドロキシ−
３−メトキシカルボニル−３，４−ジヒドロ−２
（1H）−キノロン500mgを得た。
当該化合物の物理的及び化学的性状は下記の通
りである。
外観：黄褐色結晶性粉末
融点：67〜68℃
比旋光度：〔α〕D＝−3.8°（C1.0MeOH）
溶解性：水及び低級アルコールに易溶。酢酸エチ
ル、クロロホルム、ベンゼンに難溶。
味：水溶液は苦味を呈する。
元素分析値（C11H11O5として）
INDUSTRIAL APPLICATION FIELD The present invention relates to novel 2(1H)-quinolone derivatives having immunomodulatory, antiallergic, and antiinflammatory and analgesic effects, and more specifically to 3,6-dihydroxy-3-methoxycarbonyl-3,4-dihydroquinolone derivatives. -2(1H)-quinolone (hereinafter referred to as compound []) and its salt. Object of the invention The object of the invention is to provide a compound [I] that can be an active ingredient of an immunomodulator, an antiallergic agent, and an anti-inflammatory analgesic.
and to provide that salt. Composition of the invention The compound [ ] of the present invention has the above chemical structural formula, and the hydroxyl group at the 3- and/or 6-position is replaced with a pharmaceutically acceptable strong basic compound, such as sodium hydroxide, potassium hydroxide, hydroxide. By acting on calcium etc., compounds []
salt can be easily obtained. The compound [ ] of the present invention and its salts have immunomodulatory, antiallergic, and antiinflammatory and analgesic effects, and are therefore extremely useful as medicinal ingredients of immunomodulators, antiallergic agents, and antiinflammatory and analgesic agents. In addition, the compound of the present invention [ ] also includes its racemate and optical isomer. The compound of the present invention [ ] can be easily isolated from, for example, rice sugar. As the isolation means, known separation methods such as solvent extraction, column chromatography, and thin layer chromatography are employed. To describe an example of a method for isolating the compound [ ] from rice sugar, rice sugar, preferably in a dry state, is
The alcohol-soluble content is extracted from the rice sugar by immersing it in a lower alcohol such as methanol, ethanol, or isopropanol at room temperature to 50°C to obtain a primary extract. If necessary, add a lower alcohol to this first extract, add a hydrophobic solvent (for example, n-hexane) and water, mix thoroughly, and leave the mixture still or centrifuge it. Separate the layers,
An aqueous solution containing lower alcohol and no lipid is separated. Next, after concentrating this aqueous solution under reduced pressure or drying it under reduced pressure, lower alcohol is added again to dissolve the alcohol-soluble substances therein, and the alcohol-insoluble substances (carbohydrates) are removed from the alcohol solution to obtain the second extract. obtain. After the secondary extract thus obtained is preferably concentrated under reduced pressure, a mixture of lower alcohol and chloroform is added and mixed, the resulting tar-like substance is precipitated, and the supernatant is collected. Next, the substance obtained by drying this supernatant liquid under reduced pressure is dissolved in a lower alcohol, and the target compound [] is isolated by subjecting the alcohol solution to column chromatography or thin film chromatography. Can be done. For example, silica gel, activated alumina, silver nitrate silica gel, etc. can be used as a carrier for column chromatography, and as an eluent, for example, n
-hexane, benzene, diethyl ether, chloroform, ethyl acetate, acetone, methanol,
Ethanol and mixtures thereof can be used. The present invention will be further explained below with reference to Examples. Example Methanol made by heating 10kg of dried rice sugar to 40℃
50 for 1 hour to perform extraction, and the obtained primary extract was concentrated under reduced pressure to a concentration of 5. Add 10 parts of n-hexane and 10 parts of water to this concentrated solution and heat at 40°C.
When the mixture is shaken and left to stand, an aqueous solution containing methanol is separated into a lower layer, and this is separated to obtain an aqueous solution. Next, this aqueous solution is evaporated to dryness under reduced pressure, pure methanol 5 is added to the dried product to precipitate carbohydrates, and the precipitate is removed by filtration to obtain a methanol solution (secondary extract). obtain. After evaporating this methanol solution to dryness, methanol/chloroform mixed solution (volume ratio 2:
8) Add 5, sediment the generated tar-like substance, and separate the supernatant. Next, this supernatant liquid was evaporated to dryness, and methanol was added to it again.
Prepare a methanol solution. On the other hand, Kieselgel 60G manufactured by Merck, 0.5 mm thick
Make a thin layer of and activate this at 120℃ for 1 hour. On this thin layer, the previously prepared methanol solution is spotted in a linear manner, developed for 10 cm with a mixed solvent of metamer and chloroform (volume ratio 1:9), and the portion with an Rf value of 0.26 is collected and extracted with methanol. Thereafter, by distilling off the methanol from the extract, 3,6-dihydroxy-
3-methoxycarbonyl-3,4-dihydro-2
500 mg of (1H)-quinolone was obtained. The physical and chemical properties of the compound are as follows. Appearance: Yellow-brown crystalline powder Melting point: 67-68℃ Specific rotation: [α] D = -3.8° (C1.0MeOH) Solubility: Easily soluble in water and lower alcohols. Slightly soluble in ethyl acetate, chloroform, and benzene. Taste: Aqueous solution has a bitter taste. Elemental analysis value (as C 11 H 11 O 5 )
【表】 紫外吸収 λEtOH max：265nｍ，325nｍ Ε１％ １cm（265nｍ）＝353.4 核磁気共鳴吸収（第１図及び第２図参照）1 H NMR（CD3OD、400MHz） δppm＝2.97（1H、ｄ、Ｊ＝15.4） ＝3.03（1H、ｄ、Ｊ＝15.4） ＝3.49（3H、Ｓ） ＝6.67（1H、dd、Ｊ＝8.3、2.3） ＝6.70（1H、dd、Ｊ＝8.3、0.6） ＝6.84（1H、dd、Ｊ＝2.3、0.6） （CD3ODのシグナルを3.30ppmとした時）13 C NMR（DMSO−d6、50MHz） δppm＝41.5、50.7、72.9、109.6、 112.1、115.0、131.7、133.8、 152.3、168.8、177.4 （DMSO−d6を39.5′として） 質量スペクトル（第３図参照） ｍ／Ｚ 237（M+、C11H11NO5）、 219（Ｍ−H2O）、 185、177（Ｍ−C2H4O2）、 164、135（Ｍ−C4H6O3） 赤外スペクトル（第４図参照……KBr錠剤法）[Table] Ultraviolet absorption λEtOH max: 265nm, 325nm E1% 1cm (265nm) = 353.4 Nuclear magnetic resonance absorption (see Figures 1 and 2) 1 H NMR (CD 3 OD, 400MHz) δppm = 2.97 (1H, d , J = 15.4) = 3.03 (1H, d, J = 15.4) = 3.49 (3H, S) = 6.67 (1H, dd, J = 8.3, 2.3) = 6.70 (1H, dd, J = 8.3, 0.6) = 6.84 (1H, dd, J = 2.3, 0.6) (When CD 3 OD signal is 3.30 ppm) 13 C NMR (DMSO-d 6 , 50 MHz) δppm = 41.5, 50.7, 72.9, 109.6, 112.1, 115.0, 131.7, 133.8, 152.3, 168.8, 177.4 (DMSO-d 6 as 39.5') Mass spectrum (see Figure 3) m/Z 237 (M + , C 11 H 11 NO 5 ), 219 (M-H 2 O ), 185, 177 (M-C 2 H 4 O 2 ), 164, 135 (M-C 4 H 6 O 3 ) Infrared spectrum (see Figure 4...KBr tablet method)
第１図は実施例で得た本発明の化合物〔〕の
1H核磁気共鳴スペクトルを、第２図は同じく化
合物〔〕の13C核磁気共鳴スペクトルを示す。
第３図は実施例で得た本発明の化合物〔〕のマ
ススペクトルを、第４図は同じく化合物〔〕の
赤外スペクトルを示す。
Figure 1 shows the compound of the present invention [] obtained in Example.
Figure 2 shows the 1 H nuclear magnetic resonance spectrum and the 13 C nuclear magnetic resonance spectrum of the compound [].
FIG. 3 shows the mass spectrum of the compound [ ] of the present invention obtained in the Examples, and FIG. 4 shows the infrared spectrum of the compound [ ].
Claims (1)
カルボニル−３，４−ジヒドロ−２（1H）−キノ
ロン又はその塩。[Claims] 1 formula 3,6-dihydroxy-3-methoxycarbonyl-3,4-dihydro-2(1H)-quinolone or a salt thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12308384A JPS611666A (en) | 1984-06-15 | 1984-06-15 | Novel 2(1h)-quinolone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12308384A JPS611666A (en) | 1984-06-15 | 1984-06-15 | Novel 2(1h)-quinolone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS611666A JPS611666A (en) | 1986-01-07 |
| JPH0458467B2 true JPH0458467B2 (en) | 1992-09-17 |
Family
ID=14851772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12308384A Granted JPS611666A (en) | 1984-06-15 | 1984-06-15 | Novel 2(1h)-quinolone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS611666A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106061454A (en) | 2014-03-06 | 2016-10-26 | 宝洁公司 | 3D base |
| US10973702B2 (en) | 2015-08-26 | 2021-04-13 | The Procter & Gamble Company | Absorbent articles having three dimensional substrates and indicia |
| TWI817867B (en) * | 2022-12-15 | 2023-10-01 | 大江生醫股份有限公司 | Use of 1,2,3,4-tetrahydroquinoline derivatives for improving atherosclerosis |
-
1984
- 1984-06-15 JP JP12308384A patent/JPS611666A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS611666A (en) | 1986-01-07 |
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