JP2021527703A - ブリバラセタム中間体、その製造方法及びブリバラセタムの製造方法 - Google Patents
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- BQMYDNIVIMBFIX-BDAKNGLRSA-N CCC[C@H](CC(O)=O)CN[C@@H](CC)C(N)=O Chemical compound CCC[C@H](CC(O)=O)CN[C@@H](CC)C(N)=O BQMYDNIVIMBFIX-BDAKNGLRSA-N 0.000 description 2
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- GIPYVQIUWHWUDC-UHFFFAOYSA-N CCCC(CC(O)=O)CNS(CC)CC(N)=O Chemical compound CCCC(CC(O)=O)CNS(CC)CC(N)=O GIPYVQIUWHWUDC-UHFFFAOYSA-N 0.000 description 1
- BQMYDNIVIMBFIX-GKAPJAKFSA-N CCCC(CC(O)=O)CN[C@@H](CC)C(N)=O Chemical compound CCCC(CC(O)=O)CN[C@@H](CC)C(N)=O BQMYDNIVIMBFIX-GKAPJAKFSA-N 0.000 description 1
- AAYKRKOACPCHOW-UHFFFAOYSA-N CCCC1=CC(O)OC1O Chemical compound CCCC1=CC(O)OC1O AAYKRKOACPCHOW-UHFFFAOYSA-N 0.000 description 1
- FMAZZNJEWVYABA-YGPZHTELSA-N CCC[C@H](C1)CN(CC(C)C(N)=O)C1=O Chemical compound CCC[C@H](C1)CN(CC(C)C(N)=O)C1=O FMAZZNJEWVYABA-YGPZHTELSA-N 0.000 description 1
- HNNJFUDLLWOVKZ-VKHMYHEASA-N CC[C@@H](C(N)=O)N Chemical compound CC[C@@H](C(N)=O)N HNNJFUDLLWOVKZ-VKHMYHEASA-N 0.000 description 1
- JUODSNRKJOVATP-LURJTMIESA-N CC[C@@H](C(N)=O)NCCCC(O)=O Chemical compound CC[C@@H](C(N)=O)NCCCC(O)=O JUODSNRKJOVATP-LURJTMIESA-N 0.000 description 1
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Abstract
【化1】
Description
(2)ステップ(1)における結晶化した後の母液にXと溶媒を添加し、結晶形を析出させ;
本発明はn−バレルアルデヒド及びグリオキシル酸を原材料とし、安価で入手が容易であり、且つ、得られた生成物をカラムクロマトグラフィーで分離する必要がなく、同時に反応過程で金属試薬を必要としない。本発明で提供されるブリバラセタムの合成経路は、ステップが短く、原材料が安く、簡潔・効率的であり、カラムクロマトグラフィーで異性体を分離又は非対称合成する必要がなく、製造コストを低減させ、工業化された大規模生産に適している。
Claims (21)
- Xはシュウ酸又はマレイン酸であり;
及び/又は、前記溶媒は水、アルコール系溶媒及び塩化チオニルの中の一つ又は複数であり、好ましくはC1−4のアルコールであり、より好ましくはメタノール、エタノール及びイソプロパノールの中の一つ又は複数であり;
及び/又は、前記式(II)−R−X又は(II)−Rで表される化合物が前記溶媒におけるモル濃度は0.2〜1.0mol/Lであり、好ましくは、0.4〜0.6mol/Lであり;
及び/又は、前記環形成反応の温度は25〜100℃であり、好ましくは、25〜80℃であり、更に好ましくは65〜80℃であり;
及び/又は、前記環形成反応の時間は4〜10hであることを特徴とする、請求項5に記載の式(I)で表されるブリバラセタムの製造方法。 - 前記Xはシュウ酸又はマレイン酸であり;
及び/又は、前記塩形成のステップの溶媒はC1−4のアルコール及び/又は水であり;
及び/又は、前記塩形成のステップの溶媒と式(II)で表される化合物の質量比は(2〜10):1であり、好ましくは(3〜5):1であり、より好ましくは4:1であり;
及び/又は、前記式(II)で表される化合物と前記Xのモル比は(0.8〜2):1であり、好ましくは(1〜1.5):1であり、より好ましくは(1〜1.3):1であり;
及び/又は、前記結晶化ステップの溶媒はC1−4のアルコール、水及びエーテル系溶媒の混合溶媒、又はC1−4のアルコール、水及びアルカン系溶媒の混合溶媒であり;
及び/又は、前記結晶化ステップの溶媒と前記式(II)で表される化合物の質量比は(5〜15):1であり、より好ましくは(7〜11):1であり;
及び/又は、前記結晶化ステップの温度は5〜50℃であり、好ましくは10〜40℃であり、より好ましくは25〜30℃であり;
及び/又は、前記結晶化ステップの結晶化時間は0.5〜5hであり、好ましくは1〜2hであることを特徴とする、請求項8に記載の式(I)で表されるブリバラセタムの製造方法。 - 前記C1−4のアルコールは、プロパノール、n−ブタノール及びイソブタノールの中の1つ又は複数であり;
及び/又は、前記エーテル系溶媒は石油エーテル及び/又はイソプロピルエーテルであり;
及び/又は、前記アルカン系溶媒はn−ヘキサン及び/又はn−ヘプタンであり;
及び/又は、前記結晶化ステップにおいて、前記C1−4のアルコール、水及び(エーテル系溶媒又はアルカン系溶媒)の質量比は(2〜10):1:(2〜10)であり、好ましくは(3〜5):1:(4〜6)であり、より好ましくは4:1:(4〜6)であることを特徴とする、請求項9に記載の式(I)で表されるブリバラセタムの製造方法。 - 前記結晶化ステップの溶媒はn−ブタノール、水及びイソプロピルエーテルの混合溶媒、イソブタノール、水及びイソプロピルエーテルの混合溶媒、イソブタノール、水及び石油エーテルの混合溶媒、n−ブタノール、水及びn−ヘプタンの混合溶媒、イソプロパノール、水及びイソプロピルエーテルの混合溶媒、又はイソプロパノール、水及びn−ヘキサンの混合溶媒であり、好ましくは、イソブタノール、水及びイソプロピルエーテルの混合溶媒、又はイソプロパノール、水とイソプロピルエーテルの混合溶媒であることを特徴とする、請求項8〜10のいずれか1項に記載の式(I)で表されるブリバラセタムの製造方法。
- 更に、式(II)で表される化合物をC1−4のアルコール及び水の混合溶媒に添加し、次に順次に有機酸、エーテル系又はアルカン系溶媒を添加し、結晶化させるステップを含むことを特徴とする、請求項9〜10のいずれか1項に記載の式(I)で表されるブリバラセタムの製造方法。
- 更に、式(II)で表される化合物をC1−4のアルコール及び水の混合溶媒に添加し、次に順次に有機酸、エーテル系又はアルカン系溶媒を添加し、結晶化させるステップを含み;結晶化させて得られた生成物をC1−4のアルコール及び水の混合溶媒に添加し、再びエーテル系又はアルカン系溶媒を添加し、結晶化させるステップを含むことを特徴とする、請求項9〜10のいずれか1項に記載の式(I)で表されるブリバラセタムの製造方法。
- 前記水素化還元反応は有機酸の関与条件下で行われ;前記有機酸はクエン酸、シュウ酸及びマレイン酸の中の一つ又は複数であり、好ましくはクエン酸であり;
及び/又は、前記有機酸と前記式(III)で表される化合物のモル比は(7〜10):1であることを特徴とする、請求項14項に記載の式(I)で表されるブリバラセタムの製造方法。 - 前記Xはシュウ酸又はマレイン酸であり;
及び/又は、ステップ(2)において、前記溶媒はエテール系溶媒であり、好ましくは石油エーテル及び/又はイソプロピルエーテルであり;
及び/又は、ステップ(2)において、前記Xと前記式(II)で表される化合物のモル比は1:(1〜4)であり;
及び/又は、ステップ(2)において、前記溶媒と前記式(II)で表される化合物の体積対質量比は(1〜4)mL/gであり;
及び/又は、ステップ(2)において、前記結晶形の析出温度は−20〜0℃であることを特徴とする、請求項18に記載の式(II)−S−Xで表される化合物を得の製造方法。
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WO2019242192A1 (zh) | 2019-12-26 |
CN110615744A (zh) | 2019-12-27 |
EP3812377A4 (en) | 2022-03-16 |
CN112020498A (zh) | 2020-12-01 |
US11518741B2 (en) | 2022-12-06 |
CN112020498B (zh) | 2024-04-02 |
US20210253523A1 (en) | 2021-08-19 |
EP3812377A1 (en) | 2021-04-28 |
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CN110615744B (zh) | 2023-01-06 |
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