JPS64398B2 - - Google Patents
Info
- Publication number
- JPS64398B2 JPS64398B2 JP57154788A JP15478882A JPS64398B2 JP S64398 B2 JPS64398 B2 JP S64398B2 JP 57154788 A JP57154788 A JP 57154788A JP 15478882 A JP15478882 A JP 15478882A JP S64398 B2 JPS64398 B2 JP S64398B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- isoquinolines
- phthalide
- formula
- represented
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- -1 phthalide isoquinolines Chemical class 0.000 claims description 12
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 9
- JEXCBTXFJQTLFP-UHFFFAOYSA-N 3-nitro-3h-2-benzofuran-1-one Chemical class C1=CC=C2C([N+](=O)[O-])OC(=O)C2=C1 JEXCBTXFJQTLFP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- IRGJVQIJENCTQF-UHFFFAOYSA-N tritoqualine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=C(OCC)C(OCC)=C(OCC)C(N)=C2C(=O)O1 IRGJVQIJENCTQF-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- FTLVJOVZLDLKLZ-UHFFFAOYSA-N 4,5,6-triethoxy-7-nitro-3h-2-benzofuran-1-one Chemical compound CCOC1=C(OCC)C(OCC)=C2COC(=O)C2=C1[N+]([O-])=O FTLVJOVZLDLKLZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000002537 isoquinolines Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Description
【発明の詳細な説明】
本発明はフタライドイソキノリン類の製法に関
し、さらに詳しくは、抗アレルギー等の作用を有
し医薬として有用なトリトクアリン製造のための
中間体、等として有用なフタライドイソキノリン
類の製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing phthalide isoquinolines, and more particularly to phthalide isoquinolines useful as intermediates for producing tritoqualin, which has antiallergic effects and is useful as a medicine. Concerning the manufacturing method.
従来、上記一般式（）で示されるフタライド
イソキノリン類は、一般式（）で示されるニト
ロフタライド類を、一般式（）で示されるイソ
キノリン類とエタノール中で反応させて得る方法
が知られている（たとえば、英国特許第873935号
明細書）。しかしながら、この方法には、必ずし
も満足すべき収率を達成できないという難点があ
る。 Conventionally, the phthalide isoquinolines represented by the general formula () above are obtained by reacting the nitrophthalides represented by the general formula () with the isoquinolines represented by the general formula () in ethanol. (For example, British Patent No. 873935). However, this method has the drawback that a satisfactory yield cannot always be achieved.
本発明者らは、収率向上のため種々検討した結
果、エタノールに代えてメタノールを使用するこ
とにより格段に収率が向上することを見出し本発
明に到達した。 As a result of various studies to improve the yield, the present inventors have found that the yield can be significantly improved by using methanol instead of ethanol, and have arrived at the present invention.
すなわち、本発明の要旨は、一般式（）
（式中、R1，R2及びR3は低級アルキル基を表
わす）
で示されるニトロフタライド類を、
一般式（）
（式中、R4，R5，R6及びR7は低級アルキル基
を表わし、R6，R7、又はR5，R6でメチレン基を
形成してもよい）
で示されるイソキノリン類とメタノール中で反応
させて、一般式（）
〔式中、R1〜R7は、一般式（）及び（）
におけると同義である。〕
で示されるフタライドイソキノリン類の光学異性
体「1RS―3′RS」体を得ることを特徴とするフ
タライドイソキノリン類の製法にある。 That is, the gist of the present invention is that the general formula () (In the formula, R 1 , R 2 and R 3 represent lower alkyl groups.) Nitrophthalides represented by the general formula () (In the formula, R 4 , R 5 , R 6 and R 7 represent a lower alkyl group, and R 6 , R 7 or R 5 and R 6 may form a methylene group) By reacting in methanol, the general formula () [In the formula, R 1 to R 7 are general formulas () and ()
It is synonymous with . ] A method for producing phthalide isoquinolines, which is characterized by obtaining the optical isomer "1RS-3'RS" of phthalide isoquinolines represented by the following.
以下、本発明を詳細に説明する。 The present invention will be explained in detail below.
まず、上記一般式においてR1〜R7は、メチル、
エチル、ｎ―プロピル、iso―プロピル、ｎ―ブ
チル等の炭素数１〜６の低級アルキル基であり、
これらは相異なつていてもよい。また、一般式
（）において、R6，R7、又はR5，R6でメチレ
ン基を形成してもよい（すなわち、OR6とOR7、
又はOR5とOR6のいずれかでメチレンジオキシ基
を形成してもよい）。 First, in the above general formula, R 1 to R 7 are methyl,
A lower alkyl group having 1 to 6 carbon atoms such as ethyl, n-propyl, iso-propyl, n-butyl,
These may be different. Furthermore, in the general formula (), R 6 , R 7 , or R 5 , R 6 may form a methylene group (i.e., OR 6 and OR 7 ,
Or a methylenedioxy group may be formed with either OR 5 or OR 6 ).
たとえば、トリトクアリンの原料としてのフタ
ライドイソキノリン類を得る場合には、コタルニ
ン
が選ばれる。 For example, when obtaining phthalide isoquinolines as raw materials for tritoqualin, cotalnin is is selected.
本方法においては、一般式（）で示されるニ
トロフタライド類と一般式（）で示されるイソ
キノリン類との反応をメタノール中で行なう。メ
タノールの量は、上記ニトロフタライド類に対
し、1.5〜10倍量（容量）程度であり、2.5〜３倍
量が最も好ましい。上記イソキノリン類の使用量
は、ニトロフタライド類に対し、通常等モル程度
である。 In this method, a reaction between a nitrophthalide represented by the general formula () and an isoquinoline represented by the general formula () is carried out in methanol. The amount of methanol is approximately 1.5 to 10 times the amount (volume) of the above-mentioned nitrophthalides, and most preferably 2.5 to 3 times the amount (volume). The amount of the above-mentioned isoquinolines used is usually about equimolar to the amount of nitrophthalides.
反応温度は50〜80℃程度が採用され、反応時間
は、８〜36時間程度である。 The reaction temperature is about 50 to 80°C, and the reaction time is about 8 to 36 hours.
反応終了後、精製は常法に従つて行なわれる。 After the reaction is completed, purification is carried out according to conventional methods.
たとえば、R1〜R3がエチル基であるニトロフ
タライド類とコタルニンとより上記方法によつて
得られるフタライドイソキノリン類は、次いで錫
等によつて還元してトリトクアリンに導くことが
できる。 For example, phthalide isoquinolines obtained by the above method from nitrophthalides in which R 1 to R 3 are ethyl groups and cotarnin can then be reduced with tin or the like to lead to tritoqualin.
この場合、本発明方法によれば、得られるフタ
ライド類は、実質的に1RS―3′RSの配置（すな
わち、トリトクアリンの配置と同一）のみを有す
るので、工業的にきわめて有利である。 In this case, according to the method of the present invention, the obtained phthalides have substantially only the 1RS-3'RS configuration (ie, the same configuration as tritoqualin), which is extremely advantageous industrially.
以下、実施例により本発明をさらに詳細に説明
する。 Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例 １
２―メチル―６，７―メチレンジオキシ―８―
メトキシ―１―〔４，５，６―トリエトキシ―
７―ニトロ―フタリジル―(3)〕―１，２，３，
４―テトラヒドロイソキノリンの合成
４，５，６―トリエトキシ―７―ニトロ―フタ
ライド34.2ｇ（0.11モル）とコタルニン26.1ｇ
（0.11モル）にメチルアルコール88mlを加え、80
℃に加熱したオイルバス中、撹拌下10時間反応さ
せる。室温になつた反応液にメチルアルコール
176mlとメチルイソブチルケトン66mlを加えて撹
拌１時間した後結晶をロ過し、少量のメチルアル
コールで洗浄すると目的物を37.0ｇ（収率64％）
得る。m.p.149.5―151.5℃
ロ液と洗浄液を減圧濃縮し、残つたオイル分に
更にコタルニン5.2ｇ（0.022モル）とメチルアル
コール18mlを加えて上記と同様に10時間反応さ
せ、全く同様に後処理を行なつて目的物9.4ｇ
（収率16％）を得る。Example 1 2-methyl-6,7-methylenedioxy-8-
Methoxy-1-[4,5,6-triethoxy-
7-nitro-phthalidyl-(3)]-1,2,3,
Synthesis of 4-tetrahydroisoquinoline 34.2 g (0.11 mol) of 4,5,6-triethoxy-7-nitro-phthalide and 26.1 g of cotarunine
(0.11 mol), add 88 ml of methyl alcohol, and add 88 ml of methyl alcohol to
React for 10 hours with stirring in an oil bath heated to ℃. Add methyl alcohol to the reaction solution that has reached room temperature.
After adding 176 ml and 66 ml of methyl isobutyl ketone and stirring for 1 hour, the crystals were filtered and washed with a small amount of methyl alcohol to obtain 37.0 g of the target product (64% yield).
obtain. mp149.5 - 151.5℃ The filtrate and washing solution were concentrated under reduced pressure, and 5.2 g (0.022 mol) of cotalunine and 18 ml of methyl alcohol were added to the remaining oil, reacted for 10 hours in the same manner as above, and post-treated in the same manner. Target 9.4g
(yield 16%).
得られる上記目的物はいずれも、1RS―3′RS
体であつた。 All of the above objects obtained are 1RS−3′RS
My body was warm.
比較例 １
４，５，６―トリエトキシ―７―ニトロ―フタ
ライド2.10ｇ（8.86ミリモル）、コタルニン2.75ｇ
（8.84ミリモル）と粉状の無水硫酸ナトリウム
2.10ｇに無水エタノール30mlを加え、窒素気流
下、27時間撹拌還流させ反応を行なう。反応終了
後反応液を冷蔵庫に１晩放置し析出した結晶をロ
過し乾燥すると２種類の異性体よりなる２―メチ
ル―６，７―メチレンジオキシ―８―メトキシ―
１―〔４，５，６―トリエトキシ―７―ニトロ―
フタリジル―(3)〕―１，２，３，４―テトラヒド
ロイソキノリンを1.76ｇ（収率36％）得る。m.
p.124―141℃
なお、上記異性体は1RS―3′RS体と1RS―
3′RS体であり、その比率は約2.5：１であつた。Comparative Example 1 2.10 g (8.86 mmol) of 4,5,6-triethoxy-7-nitro-phthalide, 2.75 g of cotalunine
(8.84 mmol) and powdered anhydrous sodium sulfate
Add 30 ml of absolute ethanol to 2.10 g, and stir and reflux for 27 hours under a nitrogen atmosphere to carry out the reaction. After the reaction is completed, the reaction solution is left in the refrigerator overnight, and the precipitated crystals are filtered and dried to obtain 2-methyl-6,7-methylenedioxy-8-methoxy, which consists of two types of isomers.
1-[4,5,6-triethoxy-7-nitro-
1.76 g (yield 36%) of phthalidyl-(3)]-1,2,3,4-tetrahydroisoquinoline was obtained. m.
p.124-141℃ The above isomers are 1RS-3′RS form and 1RS-
It was a 3'RS form, and the ratio was approximately 2.5:1.
参考例 １
トリトクアリンの合成
（1RS―3′RS―）２―メチル―６，７―メチ
レンジオキシ―８―メトキシ―１―〔４，５，６
―トリエトキシ―７―ニトロ―フタリジル―(3)〕
―１，２，３，４―テトラヒドロイソキノリン
26.5ｇ（0.05モル）と錫粉11.9ｇ（0.10モル）に
アセトン100mlを加え、氷冷下撹拌しながら、8N
―塩酸水溶液117mlを徐々に1.5時間かけて滴下す
る。この時反応液の温度は20℃を越えない様に滴
下速度を調節する。滴下終了後氷浴をとり除き室
温で撹拌１時間反応させた後アセトンを減圧留去
し、残つた水溶液からジクロルエタン抽出する。
ジクロルエタン層を合しこれに氷冷下10％水酸化
ナトリウム水溶液150mlを徐々に加え、得られた
アミン化合物をフリーにする。水層を分液除去後
ジクロルエタン層を１％EDTA水溶液で２回洗
浄、更に水洗後硫酸マグネシウム上で乾燥する。
溶媒を留去して残つた結晶をメチルエチルケトン
から再結晶して純粋なトリトクアリン23.0ｇ（収
率92％）を得る。m.p.180.5―182℃。Reference example 1 Synthesis of tritoqualin (1RS-3′RS-)2-methyl-6,7-methylenedioxy-8-methoxy-1-[4,5,6
-Triethoxy-7-nitro-phthalidyl-(3)]
-1,2,3,4-tetrahydroisoquinoline
Add 100ml of acetone to 26.5g (0.05mol) and 11.9g (0.10mol) of tin powder, and add 8N while stirring under ice cooling.
- Gradually add 117 ml of hydrochloric acid solution dropwise over 1.5 hours. At this time, the dropping rate is adjusted so that the temperature of the reaction solution does not exceed 20°C. After the dropwise addition was completed, the ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hour. The acetone was distilled off under reduced pressure, and the remaining aqueous solution was extracted with dichloroethane.
Combine the dichloroethane layers and gradually add 150 ml of 10% aqueous sodium hydroxide solution under ice cooling to free the resulting amine compound. After separating and removing the aqueous layer, the dichloroethane layer was washed twice with a 1% aqueous EDTA solution, further washed with water, and then dried over magnesium sulfate.
The solvent was distilled off and the remaining crystals were recrystallized from methyl ethyl ketone to obtain 23.0 g (yield 92%) of pure tritoqualin. mp180.5―182℃.
Claims (1)
わす） で示されるニトロフタライド類を、一般式（） （式中、R4，R5，R6及びR7は低級アルキル基
を表わし、R6，R7又はR5，R6でメチレン基を形
成してもよい） で示されるイソキノリン類とメタノール中で反応
させて、一般式（） 〔式中、R1〜R7は、一般式（）及び（）
におけると同義である。〕 で示される、フタライドイソキノリン類の光学異
性体（1RS―3′RS〕体を得ることを特徴とする
フタライドイソキノリン類の製法。[Claims] 1 General formula () (In the formula, R 1 , R 2 and R 3 represent lower alkyl groups.) Nitrophthalides represented by the general formula () (In the formula, R 4 , R 5 , R 6 and R 7 represent a lower alkyl group, and R 6 , R 7 or R 5 and R 6 may form a methylene group) and methanol React in the general formula () [In the formula, R 1 to R 7 are general formulas () and ()
It is synonymous with . ] A method for producing phthalide isoquinolines, which is characterized by obtaining an optical isomer (1RS-3'RS) of phthalide isoquinolines.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15478882A JPS5944382A (en) | 1982-09-06 | 1982-09-06 | Preparation of phthalide isoquinoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15478882A JPS5944382A (en) | 1982-09-06 | 1982-09-06 | Preparation of phthalide isoquinoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5944382A JPS5944382A (en) | 1984-03-12 |
| JPS64398B2 true JPS64398B2 (en) | 1989-01-06 |
Family
ID=15591906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15478882A Granted JPS5944382A (en) | 1982-09-06 | 1982-09-06 | Preparation of phthalide isoquinoline |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5944382A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB873935A (en) * | 1959-08-05 | 1961-08-02 | Maurice Jeanson | Improvements in and relating to new isoquinoline phthalides and their process of preparation |
-
1982
- 1982-09-06 JP JP15478882A patent/JPS5944382A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB873935A (en) * | 1959-08-05 | 1961-08-02 | Maurice Jeanson | Improvements in and relating to new isoquinoline phthalides and their process of preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5944382A (en) | 1984-03-12 |
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