JP2021527621A - ガドリニウム系造影剤におけるtert−ブチルエステルの加水分解方法 - Google Patents
ガドリニウム系造影剤におけるtert−ブチルエステルの加水分解方法 Download PDFInfo
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- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
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- A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
- A61K49/106—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/135—Halogens; Compounds thereof with titanium, zirconium, hafnium, germanium, tin or lead
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/04—Mixing
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/06—Washing
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- A—HUMAN NECESSITIES
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- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/05—Detecting, measuring or recording for diagnosis by means of electric currents or magnetic fields; Measuring using microwaves or radio waves
- A61B5/055—Detecting, measuring or recording for diagnosis by means of electric currents or magnetic fields; Measuring using microwaves or radio waves involving electronic [EMR] or nuclear [NMR] magnetic resonance, e.g. magnetic resonance imaging
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
- G01N24/08—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects by using nuclear magnetic resonance
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
- G01R33/44—Arrangements or instruments for measuring magnetic variables involving magnetic resonance using nuclear magnetic resonance [NMR]
- G01R33/48—NMR imaging systems
- G01R33/54—Signal processing systems, e.g. using pulse sequences ; Generation or control of pulse sequences; Operator console
- G01R33/56—Image enhancement or correction, e.g. subtraction or averaging techniques, e.g. improvement of signal-to-noise ratio and resolution
- G01R33/5601—Image enhancement or correction, e.g. subtraction or averaging techniques, e.g. improvement of signal-to-noise ratio and resolution involving use of a contrast agent for contrast manipulation, e.g. a paramagnetic, super-paramagnetic, ferromagnetic or hyperpolarised contrast agent
Abstract
Description
式(III)で表される化合物を、蒸留水が200mL入った500mLの反応フラスコに加え、撹拌しながら触媒を加え(式(III)で表される化合物と触媒の質量比は1:100である。)、90℃で12時間反応させ、濾過し、少量の水で洗浄し、乾固するまで減圧濃縮し、95%エタノールで再結晶させ、テリドール(teridol)として白色固体17gが得られた。
式(III)で表される化合物を、蒸留水が200mL入った500mLの反応フラスコに加え、撹拌しながら触媒を加え(式(III)で表される化合物と触媒の質量比は1:1である。)、70℃で24時間反応させ、濾過し、少量の水で洗浄し、乾固するまで減圧濃縮し、95%エタノールで再結晶させ、白色固体が得られた。そのうち、使用された触媒は、実施例1における触媒と同じものであった。本実施例で得られたテリドールの元素分析結果、赤外吸収スペクトルおよび1H NMRスペクトルは実施例1のと同じであった。本実施例で得られたテリドールの純度は99%であり、収率は90%であった。
式(III)で表される化合物を、蒸留水が200mL入った500mLの反応フラスコに加え、撹拌しながら触媒を加え(式(III)で表される化合物と触媒の質量比は1:50である。)、90℃で15時間反応させ、濾過し、少量の水で洗浄し、乾固するまで減圧濃縮し、95%エタノールで再結晶させ、白色固体が得られた。そのうち、使用された触媒は、実施例1における触媒と同じものであった。本実施例で得られたテリドールの元素分析結果、赤外吸収スペクトルおよび1H NMRスペクトルは実施例1のと同じであった。本実施例で得られたテリドールの純度は99.5%であり、収率は92%であった。
本実施例は、ガドリニウム系造影剤におけるtert−ブチルエステルの加水分解方法を提供する。本実施例において、下記のような触媒の調製方法が使用されたこと以外、実施例1におけるステップと同じであった。当該触媒の調製方法において、ZrO25g、TiCl40.76gを、蒸留水100mLに加え、硫酸5mLを加え、固体が完全に溶解するまで80℃程度で加熱し、SiO250mlを加えて2時間吸着させ、濾過し、水で二回洗浄し、10%NaOH50mlで二回洗浄し、中性になるまで蒸留水で洗浄し、500℃で焼成して触媒が得られた。
本実施例は、ガドリニウム系造影剤におけるtert−ブチルエステルの加水分解方法を提供する。本実施例において、下記のような触媒の調製方法が使用されたこと以外、実施例1におけるステップと同じであった。当該触媒の調製方法において、ZrO25g、TiCl47.59gを、蒸留水100mLに加え、硫酸30mLを加え、固体が完全に溶解するまで80℃程度で加熱し、SiO2100mlを加えて2時間吸着させ、濾過し、水で二回洗浄し、10%NaOH50mlで二回洗浄し、中性になるまで蒸留水で洗浄し、700℃で焼成して触媒が得られた。
Claims (9)
- 触媒を用いてtert−ブチルエステルを加水分解するステップを含み、
前記触媒の調製方法は、ジルコニアと塩化チタンを、硫酸と水の存在下、固体が溶解するまで60℃〜90℃で反応させ、シリカを加えて1〜5h反応させ、固体を濾取して洗浄した後に焼成するステップを含む
ことを特徴とするガドリニウム系造影剤におけるtert−ブチルエステルの加水分解方法。 - 前記ジルコニアと塩化チタンのモル比は1:(0.1〜1)であり、1:(0.4〜0.5)であることが好ましいことを特徴とする請求項1に記載の加水分解方法。
- 前記硫酸と水の体積比は(0.5〜3):10であり、(1〜1.5):10であることが好ましいことを特徴とする請求項1又は2に記載の加水分解方法。
- 前記ジルコニアとシリカの質量体積比は1:(10〜20)であり、1:(12〜15)であることが好ましいことを特徴とする請求項1〜3のいずれか1項に記載の加水分解方法。
- 前記焼成の温度は500℃〜700℃であり、550℃〜600℃であることが好ましいことを特徴とする請求項1〜4のいずれか1項に記載の加水分解方法。
- 前記tert−ブチルエステルと前記触媒の質量比は1:(1〜1000)であり、1:(50〜100)であることが好ましいことを特徴とする請求項1〜6のいずれか1項に記載の加水分解方法。
- 前記加水分解の温度は70℃〜90℃であり、時間は8〜24hであり、好ましくは、前記加水分解の温度は85℃〜90℃であり、時間は12〜15hであることを特徴とする請求項1〜7のいずれか1項に記載の加水分解方法。
- 触媒の調製方法は、ジルコニアと塩化チタンを、硫酸と水の存在下、固体が溶解するまで60℃〜90℃で反応させ、シリカを加えて1〜5h反応させ、固体を濾取して洗浄した後に焼成するステップを含むことを特徴とするガドリニウム系造影剤におけるtert−ブチルエステルの加水分解用触媒。
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Application Number | Priority Date | Filing Date | Title |
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CN201910078756.0 | 2019-01-28 | ||
CN201910078756.0A CN109851516B (zh) | 2019-01-28 | 2019-01-28 | 用于钆系造影剂中叔丁酯的水解方法 |
PCT/CN2019/073688 WO2020154891A1 (zh) | 2019-01-28 | 2019-01-29 | 用于钆系造影剂中叔丁酯的水解方法 |
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US (1) | US11618737B2 (ja) |
EP (1) | EP3835286B1 (ja) |
JP (1) | JP7128890B2 (ja) |
KR (1) | KR20210045348A (ja) |
CN (1) | CN109851516B (ja) |
ES (1) | ES2942312T3 (ja) |
WO (1) | WO2020154891A1 (ja) |
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CN104740655A (zh) * | 2015-02-13 | 2015-07-01 | 华东理工大学 | 一类具有高水合常数的核磁共振成像造影剂及其制备方法 |
WO2020154892A1 (zh) * | 2019-01-28 | 2020-08-06 | 湖北天舒药业有限公司 | 钆系离子型造影剂中间体的制备方法及其应用 |
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US4791089A (en) * | 1983-10-07 | 1988-12-13 | Enron Chemical Corporation | Zirconia-titania-silica tergels and their use as catalyst supports |
CA3002512C (en) * | 2015-12-10 | 2021-08-03 | Bracco Imaging Spa | Macrocyclic chelating ligand and use thereof as contrast agent |
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2019
- 2019-01-28 CN CN201910078756.0A patent/CN109851516B/zh active Active
- 2019-01-29 WO PCT/CN2019/073688 patent/WO2020154891A1/zh unknown
- 2019-01-29 EP EP19877540.5A patent/EP3835286B1/en active Active
- 2019-01-29 KR KR1020207011195A patent/KR20210045348A/ko not_active Application Discontinuation
- 2019-01-29 US US16/761,178 patent/US11618737B2/en active Active
- 2019-01-29 ES ES19877540T patent/ES2942312T3/es active Active
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Patent Citations (6)
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JP2001314763A (ja) * | 2000-05-10 | 2001-11-13 | Johnson Matthey Japan Inc | NOx吸蔵還元型触媒用支持材とそれを用いたNOx吸蔵還元型触媒 |
CN1623664A (zh) * | 2003-12-03 | 2005-06-08 | 浙江大学 | 钛锆固溶体及其制备方法 |
CN101062481A (zh) * | 2006-04-30 | 2007-10-31 | 肇庆学院 | 一种固体超强酸的制备方法 |
CN103068790A (zh) * | 2010-06-11 | 2013-04-24 | 拜耳知识产权有限责任公司 | 用于制备结晶的3,6,9-三氮杂-3,6,9-三(羧甲基)-4-(4-乙氧基苄基)十一烷二酸的方法以及用于制备普美显*(Primovist*)的用途 |
CN104740655A (zh) * | 2015-02-13 | 2015-07-01 | 华东理工大学 | 一类具有高水合常数的核磁共振成像造影剂及其制备方法 |
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JP7128890B2 (ja) | 2022-08-31 |
US20210179568A1 (en) | 2021-06-17 |
CN109851516B (zh) | 2020-10-02 |
CN109851516A (zh) | 2019-06-07 |
ES2942312T3 (es) | 2023-05-31 |
EP3835286A4 (en) | 2022-05-11 |
US11618737B2 (en) | 2023-04-04 |
EP3835286A1 (en) | 2021-06-16 |
KR20210045348A (ko) | 2021-04-26 |
WO2020154891A1 (zh) | 2020-08-06 |
EP3835286B1 (en) | 2023-01-11 |
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