JPH10508878A - (s)−n,n’−ビス[2−ヒドロキシ−1−(ヒドロキシメチル)エチル]−5−[(2−ヒドロキシ−1−オキソプロピル)アミノ]−2,4,6−トリヨード−1,3−ベンゼンジカルボキサアミドの、水からの結晶化方法 - Google Patents
(s)−n,n’−ビス[2−ヒドロキシ−1−(ヒドロキシメチル)エチル]−5−[(2−ヒドロキシ−1−オキソプロピル)アミノ]−2,4,6−トリヨード−1,3−ベンゼンジカルボキサアミドの、水からの結晶化方法Info
- Publication number
- JPH10508878A JPH10508878A JP9506045A JP50604597A JPH10508878A JP H10508878 A JPH10508878 A JP H10508878A JP 9506045 A JP9506045 A JP 9506045A JP 50604597 A JP50604597 A JP 50604597A JP H10508878 A JPH10508878 A JP H10508878A
- Authority
- JP
- Japan
- Prior art keywords
- iopamidol
- hydroxy
- water
- alcohol
- crystallizing
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 20
- -1 2-hydroxy-1-oxopropyl Chemical group 0.000 title abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title abstract description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 title abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title abstract description 5
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 claims abstract description 29
- 229960004647 iopamidol Drugs 0.000 claims abstract description 29
- 239000013078 crystal Substances 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 11
- 235000019441 ethanol Nutrition 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 4
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000010899 nucleation Methods 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HEWFFWKWOGSXNH-UHFFFAOYSA-N cyclohexa-2,4-diene-1,1-dicarboxamide Chemical compound C1(CC=CC=C1)(C(=O)N)C(=O)N HEWFFWKWOGSXNH-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.薬局方基準に従いかつ無水の結晶形態での化合物を与えるように、ヨーパミ ドールを、水から結晶化する方法であって、 −加熱により脱イオン水中にヨーパミドールを溶解する工程; −活性炭素により溶液を脱色する工程; −60℃で水溶液を真空−濃縮する工程; −結晶化を開始させるための無水のヨーパミドールの結晶の種を添加する工程; −60℃で結晶化させる工程; −生成した沈殿を濾過する工程;及び −湿潤生成物を真空−乾燥する工程を含むことを特徴とする方法。 2.水溶液中のヨーパミドールの濃度が、78.6%(g/mLの溶液)を越える、 請求項1記載の方法。 3.ヨーパミドールの無水形態の結晶の種が、原料ヨーパミドールの1〜10% の量である、請求項1記載の方法。 4.濾過された結晶固体が、直鎖又は分岐の(C1−C4)アルコールで、更に洗 浄される、請求項1記載の方法。 5.該アルコールが、エチルアルコールである、請求項4記載の方法。 6.請求項1〜3の方法により得られる結晶ヨーパミドール中の前の合成工程か らの溶媒の残留含量を減少させるための、直鎖又は分岐の(C1−C4)アルコー ルの用途。 7.請求項1〜3の方法により得られる結晶ヨーパミドール中の前の合成工程か らのジメチルアセトアミドの残留含量を減少させるための、直鎖又は分岐の(C1 −C4)アルコールの用途。 8.請求項7のジメチルアセトアミド含量を減少させるための、エチルアルコー ルの用途。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITRM950599 IT1277934B1 (it) | 1995-09-08 | 1995-09-08 | Processo per la cristallizzazione da acqua della s-n,n' -bis- ( 2-idrossi -1 -(idrossimetil) etil) -5- ((2 -idrossi -1- ossopropil) |
IT95RM000831 IT1277950B1 (it) | 1995-12-19 | 1995-12-19 | Processo per la cristallizzazione da acqua della s-n,n'-bis (2-idrossi -1-(idrossimetil)etil)-5-((2-idrossi-1-ossopropil)ammino).2,4,6- |
IT95A000599 | 1995-12-19 | ||
IT95A000831 | 1995-12-19 | ||
PCT/EP1996/003399 WO1997009300A1 (en) | 1995-09-08 | 1996-08-02 | Process for the crystallization from water of (s)-n,n'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH10508878A true JPH10508878A (ja) | 1998-09-02 |
JP4070235B2 JP4070235B2 (ja) | 2008-04-02 |
Family
ID=26332086
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50604597A Expired - Lifetime JP4070235B2 (ja) | 1995-09-08 | 1996-08-02 | (s)−n,n’−ビス[2−ヒドロキシ−1−(ヒドロキシメチル)エチル]−5−[(2−ヒドロキシ−1−オキソプロピル)アミノ]−2,4,6−トリヨード−1,3−ベンゼンジカルボキサアミドの、水からの結晶化方法 |
Country Status (17)
Country | Link |
---|---|
US (1) | US5689002A (ja) |
EP (1) | EP0790979B1 (ja) |
JP (1) | JP4070235B2 (ja) |
KR (1) | KR100270411B1 (ja) |
CN (1) | CN1070843C (ja) |
AT (1) | ATE187437T1 (ja) |
AU (1) | AU708195B2 (ja) |
BR (1) | BR9606624A (ja) |
CA (1) | CA2204734C (ja) |
CZ (1) | CZ288645B6 (ja) |
DE (1) | DE69605528T2 (ja) |
ES (1) | ES2140887T3 (ja) |
HK (1) | HK1001861A1 (ja) |
HU (1) | HU220965B1 (ja) |
NO (1) | NO308841B1 (ja) |
PL (1) | PL184937B1 (ja) |
WO (1) | WO1997009300A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PT101720A (pt) * | 1995-06-08 | 1997-01-31 | Hovione Sociedade Quimica S A | Processo para a purificacao e cristalizacao de iopamidol |
KR20000031642A (ko) * | 1998-11-09 | 2000-06-05 | 강재헌 | 이오파미돌의 결정화 방법 |
BR0214209A (pt) * | 2001-11-16 | 2004-10-26 | Ranbaxy Lab Ltd | Processo para a preparação de imipenem cristalino e composto preparado pelo dito processo |
CN100418945C (zh) * | 2006-01-13 | 2008-09-17 | 江苏省原子医学研究所 | 一种碘昔兰的纯化方法 |
US20110021834A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | Continuous process of preparing intermediate for non-ionic x-ray contrast agents |
WO2012136813A2 (en) | 2011-04-07 | 2012-10-11 | Universitetet I Oslo | Agents for medical radar diagnosis |
CN110023279B (zh) | 2016-12-05 | 2022-03-11 | 伯拉考成像股份公司 | 放射照相剂中间体的机械化学合成 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH608189A5 (ja) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
IL110391A (en) * | 1993-07-30 | 1998-12-06 | Zambon Spa | Process for the formation of infamidol |
-
1996
- 1996-08-02 KR KR1019970702994A patent/KR100270411B1/ko not_active IP Right Cessation
- 1996-08-02 EP EP96928403A patent/EP0790979B1/en not_active Expired - Lifetime
- 1996-08-02 JP JP50604597A patent/JP4070235B2/ja not_active Expired - Lifetime
- 1996-08-02 CN CN96191028A patent/CN1070843C/zh not_active Expired - Lifetime
- 1996-08-02 WO PCT/EP1996/003399 patent/WO1997009300A1/en active IP Right Grant
- 1996-08-02 HU HU9801837A patent/HU220965B1/hu unknown
- 1996-08-02 DE DE69605528T patent/DE69605528T2/de not_active Expired - Lifetime
- 1996-08-02 CA CA002204734A patent/CA2204734C/en not_active Expired - Lifetime
- 1996-08-02 AU AU67888/96A patent/AU708195B2/en not_active Expired
- 1996-08-02 BR BR9606624A patent/BR9606624A/pt not_active Application Discontinuation
- 1996-08-02 CZ CZ19971385A patent/CZ288645B6/cs not_active IP Right Cessation
- 1996-08-02 AT AT96928403T patent/ATE187437T1/de not_active IP Right Cessation
- 1996-08-02 ES ES96928403T patent/ES2140887T3/es not_active Expired - Lifetime
- 1996-08-02 PL PL96320027A patent/PL184937B1/pl unknown
- 1996-09-05 US US08/708,668 patent/US5689002A/en not_active Expired - Lifetime
-
1997
- 1997-04-23 NO NO971863A patent/NO308841B1/no not_active IP Right Cessation
-
1998
- 1998-02-10 HK HK98100990A patent/HK1001861A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
ATE187437T1 (de) | 1999-12-15 |
CZ288645B6 (cs) | 2001-08-15 |
AU6788896A (en) | 1997-03-27 |
NO971863D0 (no) | 1997-04-23 |
ES2140887T3 (es) | 2000-03-01 |
DE69605528T2 (de) | 2000-05-04 |
PL320027A1 (en) | 1997-09-01 |
JP4070235B2 (ja) | 2008-04-02 |
AU708195B2 (en) | 1999-07-29 |
NO971863L (no) | 1997-04-23 |
HUP9801837A3 (en) | 2001-06-28 |
CZ138597A3 (cs) | 1998-02-18 |
CA2204734C (en) | 2009-12-29 |
EP0790979B1 (en) | 1999-12-08 |
US5689002A (en) | 1997-11-18 |
CA2204734A1 (en) | 1997-03-13 |
MX9703341A (es) | 1997-07-31 |
CN1070843C (zh) | 2001-09-12 |
PL184937B1 (pl) | 2003-01-31 |
HK1001861A1 (en) | 1998-07-17 |
EP0790979A1 (en) | 1997-08-27 |
CN1164853A (zh) | 1997-11-12 |
WO1997009300A1 (en) | 1997-03-13 |
BR9606624A (pt) | 1997-11-11 |
KR970707073A (ko) | 1997-12-01 |
HUP9801837A2 (hu) | 1998-12-28 |
DE69605528D1 (de) | 2000-01-13 |
NO308841B1 (no) | 2000-11-06 |
HU220965B1 (hu) | 2002-07-29 |
KR100270411B1 (ko) | 2000-11-01 |
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