JPH11510827A - イオパミドールの調製中の中間体の精製方法 - Google Patents
イオパミドールの調製中の中間体の精製方法Info
- Publication number
- JPH11510827A JPH11510827A JP10501197A JP50119798A JPH11510827A JP H11510827 A JPH11510827 A JP H11510827A JP 10501197 A JP10501197 A JP 10501197A JP 50119798 A JP50119798 A JP 50119798A JP H11510827 A JPH11510827 A JP H11510827A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- anionic
- conditioned
- bed
- cationic
- 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 40
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000000543 intermediate Substances 0.000 title description 17
- 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 title description 3
- 229960004647 iopamidol Drugs 0.000 title description 3
- 229920005989 resin Polymers 0.000 claims abstract description 91
- 239000011347 resin Substances 0.000 claims abstract description 91
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 6
- 238000002955 isolation Methods 0.000 claims abstract description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 40
- 125000000129 anionic group Chemical group 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 17
- 125000002091 cationic group Chemical group 0.000 claims description 16
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 14
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- -1 acetonitrile ester Chemical class 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000002872 contrast media Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 claims description 2
- 230000001143 conditioned effect Effects 0.000 claims 12
- 159000000000 sodium salts Chemical class 0.000 claims 3
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims 2
- GVULBYBBPKVIQE-UHFFFAOYSA-N 1-[2,3-bis(ethenyl)phenyl]-2-methylprop-2-en-1-one Chemical compound CC(=C)C(=O)C1=CC=CC(C=C)=C1C=C GVULBYBBPKVIQE-UHFFFAOYSA-N 0.000 claims 2
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 claims 2
- FGGQULYFLASSKR-UHFFFAOYSA-N 1-[2,3-bis(ethenyl)phenyl]prop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC(C=C)=C1C=C FGGQULYFLASSKR-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 claims 1
- GMPOMLNJZPYPGR-VKHMYHEASA-N [(2s)-1-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-1-oxopropan-2-yl] acetate Chemical compound CC(=O)O[C@@H](C)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I GMPOMLNJZPYPGR-VKHMYHEASA-N 0.000 abstract description 6
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- 238000011097 chromatography purification Methods 0.000 abstract description 2
- FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 abstract 1
- 229920001429 chelating resin Polymers 0.000 description 34
- 239000000243 solution Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229940113088 dimethylacetamide Drugs 0.000 description 8
- 239000012045 crude solution Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 2
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 description 2
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- DOGCTUGYGZGSFX-UHFFFAOYSA-N 1-aminopropane-1,3-diol Chemical compound NC(O)CCO DOGCTUGYGZGSFX-UHFFFAOYSA-N 0.000 description 1
- FQAXLTARZOJBPJ-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=C(I)C=C(I)C(C(Cl)=O)=C1I FQAXLTARZOJBPJ-UHFFFAOYSA-N 0.000 description 1
- QMQFFHSJUJDRPG-UHFFFAOYSA-N 3-amino-2,4,6-triiodobenzoic acid Chemical class NC1=C(I)C=C(I)C(C(O)=O)=C1I QMQFFHSJUJDRPG-UHFFFAOYSA-N 0.000 description 1
- GOCIYSIBXXQUAW-REOHCLBHSA-N 5-[[(2s)-2-hydroxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I GOCIYSIBXXQUAW-REOHCLBHSA-N 0.000 description 1
- 241001370313 Alepes vari Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000003911 water pollution Methods 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
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Removal Of Specific Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Carbon And Carbon Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.スキーム1: による(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シアミドの調製方法であって、以下の 工程: a)ジメチルアセトアミド中の式(II)の化合物、(S)−5−[[2−(アセチ ルオキシ)−1−オキソプロピル]アミノ]−2,4,6−トリヨード−1,3− ベンゼンジカルボン酸二塩化物の溶液を得るための、式(I)の化合物、5−アミ ノ−2,4,6−トリヨード−1,3−ベンゼンジカルボン酸二塩化物と、(S) −(−)−[2−(アセチルオキシ)]プロピオン酸塩化物とのジメチルアセト アミド中での反応; b)工程a)で得られた溶液の、陰イオン性および陽イオン性の、陰イオン性 樹脂は遊離の塩基の形態の、陽イオン性樹脂はナトリウム塩の形態の、多孔性お よび/またはマクロポーラス質架橋樹脂からの溶出、ただし、該溶液および樹脂 によって構成される系は、過剰なS−(−)−[2−(アセチルオキシ)]プロ ピオン酸塩化物を加水分解し得るが、化合物の(II)の二塩化物は加水分解しない 量の水を含んでいる; c)工程b)で得られた溶液からの含有量0−2%までの可能な水の除去; d)セリノールとの温度0−10℃での5−20時間の反応; e)式(III)の化合物の単離 を包含する調製方法。 2.前記工程a)において、多孔性および/またはマクロポーラス架橋樹脂のポ リマー構造が:アクリル−ジビニルベンゼン、スチレン−ジビニルベンゼン、ま たはメタアクリル−ジビニルベンゼンによって構成される群から選択される、請 求項1に記載の方法。 3.前記樹脂が、単独で調整されるか連続して連なっており、あるいは混合床で あるかまたは浮遊床であり、そして溶出が低圧もしくは高圧下で行われる請求項 1または2に記載の方法。 4.前記樹脂が、分離床内に調整された弱陰イオン性樹脂である、請求項3に記 載の方法。 5.前記樹脂が、分離床内に調整された弱陰イオン性樹脂であり、それに分離床 内に調整された1つの強陰イオン性樹脂が続いている、請求項4に記載の方法。 6.前記樹脂が、分離床内に調整された弱陰イオン性樹脂であり、それに分離床 内に調整された異なる弱陰イオン性樹脂が続いている、請求項4に記載の方法。 7.前記樹脂が、混合床内に調整された弱陰イオン性樹脂と強陰イオン性樹脂で ある、請求項4に記載の方法。 8.前記樹脂が浮遊床内に調整された強陰イオン性樹脂であり、そして前記溶液 がカラム底部から負荷される、請求項4に記載の方法。 9.前記樹脂が浮遊床内に調整された弱陰イオン性樹脂であり、そして前記溶液 がカラム底部から負荷される、請求項4に記載の方法。 10.前記樹脂が、弱陰イオン性樹脂であり、それに強陰イオン性樹脂が続き、 それに陽イオン性樹脂が続き、該樹脂が分離床内に調整されている、請求項4に 記載の方法。 11.(S)−(−)−[2−(アセチルオキシ)]プロピオン酸塩化物の加水 分解に必要な水の量が溶出前の水の添加によって得られ得る、請求項1に記載の 方法。 12.工程c)における水の除去が減圧下での蒸留によって行われる、請求項1に 記載の方法。 13.ジメチルホルムアミド、N−メチルピロリドン、アセトアミド、ジメチル スルホキシド、カルボン酸のアセトニトリルエステルによって構成される群から 選択される双極性非プロトン性溶媒の精製のための多孔性および/またはマクロ ポーラス架橋樹脂であって、遊離の塩基の形態の弱陰イオン性もしくは強陰イオ ン性、またはナトリウム塩の形態としての陽イオン性樹脂またはそれらの任意の 他の混合物の使用。 14.前記多孔性および/またはマクロポーラス架橋樹脂のポリマー構造が、ア クリル−ジビニルベンゼン、スチレン−ジビニルベンゼンまたはメタアクリル− ジビニルベンゼンによって構成される群から選択される、請求項13に記載の使 用。 15.前記樹脂が混合床または連続した分離床内に調整されている、請求項13ま たは14に記載の使用。 16.前記樹脂が、強陰イオン性樹脂と陽イオン性樹脂との混合床内に調整され ている、請求項15に記載の使用。 17.前記樹脂が、連続した陽イオン性樹脂、強陰イオン性樹脂、陽イオン性樹 脂で調整されている、請求項16に記載の使用。 18.有機塩および無機塩からジメチルアセトアミドを精製する方法であって、 多孔性および/またはマクロポーラス架橋樹脂であって、陰イオン性および/ま たは陽イオン性であり、陰イオン樹脂は遊離の塩基の形態であり陽イオン樹脂は ナトリウム塩の形態であり、請求項13〜17にしたがって使用される、樹脂か らの溶出を包含する方法。 19.ジメチルアセトアミドが、ヨウ素化された造影剤の調製のために用いられ る、請求項20に記載の方法。 20.溶媒として用いられるジメチルアセトアミドが請求項18の方法で精製さ れる、請求項1に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT96MI001204A IT1288114B1 (it) | 1996-06-13 | 1996-06-13 | Processo per la purificazione di un intermedio |
IT96A001204 | 1996-06-13 | ||
PCT/EP1997/003021 WO1997047590A2 (en) | 1996-06-13 | 1997-06-11 | Process for the purification of an intermediate in the preparation of iopamidol |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11510827A true JPH11510827A (ja) | 1999-09-21 |
JP4018751B2 JP4018751B2 (ja) | 2007-12-05 |
Family
ID=11374420
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50119798A Expired - Lifetime JP4018751B2 (ja) | 1996-06-13 | 1997-06-11 | イオパミドールの調製中の中間体の精製方法 |
Country Status (17)
Country | Link |
---|---|
US (1) | US5849953A (ja) |
EP (1) | EP0851854B1 (ja) |
JP (1) | JP4018751B2 (ja) |
CN (1) | CN1089335C (ja) |
AT (1) | ATE210630T1 (ja) |
AU (1) | AU3094597A (ja) |
CZ (1) | CZ293956B6 (ja) |
DE (1) | DE69709044T2 (ja) |
ES (1) | ES2165610T3 (ja) |
HU (1) | HU227980B1 (ja) |
IL (1) | IL123259A (ja) |
IN (1) | IN182809B (ja) |
IT (1) | IT1288114B1 (ja) |
NO (1) | NO324342B1 (ja) |
PT (1) | PT851854E (ja) |
WO (1) | WO1997047590A2 (ja) |
ZA (1) | ZA975203B (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002517381A (ja) * | 1998-05-08 | 2002-06-18 | ディブラ・ソシエタ・ペル・アチオニ | 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シアミドを製造する方法 |
JP2018517705A (ja) * | 2015-06-02 | 2018-07-05 | ホビオネ サイエンティア リミテッド | 非イオン性造影剤の調製に有用な中間体の調製プロセス |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1302200B1 (it) * | 1998-09-11 | 2000-07-31 | Dibra Spa | PROCESSO PER LA PREPARAZIONE DELLA S-N,N'-BIS°2-IDROSSI-1-(IDROSSIMETIL)ETILé-5-°(2-IDROSSI-1- |
DE102007053531B4 (de) * | 2007-11-09 | 2010-10-21 | Hs Genion Gmbh | Rolloeinrichtung |
EP2230227A1 (en) | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Process for the preparation of triiodinated carboxylic aromatic derivatives |
EP2243767A1 (en) | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Process for the iodination of aromatic compounds |
IT1403988B1 (it) * | 2010-07-15 | 2013-11-08 | Bracco Imaging Spa | Processo per la preparazione di agenti di contrasto. |
PL2931696T3 (pl) | 2012-12-11 | 2019-01-31 | Bracco Imaging S.P.A | Ciągły sposób otrzymywania kwasu (S)-2-acetyloksypropionowego |
ES2674279T3 (es) | 2013-11-05 | 2018-06-28 | Bracco Imaging S.P.A. | Proceso para la preparación de Iopamidol |
NZ726674A (en) | 2014-06-10 | 2022-12-23 | Bracco Imaging Spa | Method for the preparation of (s)-2-acetyloxypropionic acid and derivatives thereof |
WO2018104228A1 (en) | 2016-12-05 | 2018-06-14 | Bracco Imaging Spa | Mechanochemical synthesis of radiographic agents intermediates |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3324107A (en) * | 1964-03-27 | 1967-06-06 | Du Pont | Dialkylamide purification |
US3576870A (en) * | 1967-07-05 | 1971-04-27 | Du Pont | Process for purifying n,n-dimethylacetamide |
CH608189A5 (ja) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
CH616403A5 (en) * | 1975-10-29 | 1980-03-31 | Bracco Ind Chimica Spa | Process for the preparation of 2,4,6-triodoisophthalamides which are readily soluble in water. |
IT1193211B (it) * | 1979-08-09 | 1988-06-15 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono |
GB2088850B (en) * | 1980-12-09 | 1983-09-28 | Coal Industry Patents Ltd | Treatment of n-methyl pyrrolidone |
IT1256162B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
-
1996
- 1996-06-13 IT IT96MI001204A patent/IT1288114B1/it active IP Right Grant
-
1997
- 1997-06-11 CN CN97190690A patent/CN1089335C/zh not_active Expired - Lifetime
- 1997-06-11 CZ CZ1998399A patent/CZ293956B6/cs not_active IP Right Cessation
- 1997-06-11 JP JP50119798A patent/JP4018751B2/ja not_active Expired - Lifetime
- 1997-06-11 AU AU30945/97A patent/AU3094597A/en not_active Abandoned
- 1997-06-11 AT AT97925993T patent/ATE210630T1/de not_active IP Right Cessation
- 1997-06-11 HU HU9901631A patent/HU227980B1/hu unknown
- 1997-06-11 DE DE69709044T patent/DE69709044T2/de not_active Expired - Lifetime
- 1997-06-11 IL IL12325997A patent/IL123259A/xx not_active IP Right Cessation
- 1997-06-11 PT PT97925993T patent/PT851854E/pt unknown
- 1997-06-11 WO PCT/EP1997/003021 patent/WO1997047590A2/en active IP Right Grant
- 1997-06-11 ES ES97925993T patent/ES2165610T3/es not_active Expired - Lifetime
- 1997-06-11 EP EP97925993A patent/EP0851854B1/en not_active Expired - Lifetime
- 1997-06-12 US US08/873,771 patent/US5849953A/en not_active Expired - Lifetime
- 1997-06-12 ZA ZA9705203A patent/ZA975203B/xx unknown
- 1997-06-13 IN IN1291MA1997 patent/IN182809B/en unknown
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1998
- 1998-02-11 NO NO19980594A patent/NO324342B1/no not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002517381A (ja) * | 1998-05-08 | 2002-06-18 | ディブラ・ソシエタ・ペル・アチオニ | 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シアミドを製造する方法 |
JP2018517705A (ja) * | 2015-06-02 | 2018-07-05 | ホビオネ サイエンティア リミテッド | 非イオン性造影剤の調製に有用な中間体の調製プロセス |
Also Published As
Publication number | Publication date |
---|---|
HUP9901631A2 (hu) | 1999-08-30 |
HUP9901631A3 (en) | 2001-02-28 |
CZ39998A3 (cs) | 1998-07-15 |
EP0851854B1 (en) | 2001-12-12 |
ITMI961204A0 (ja) | 1996-06-13 |
ATE210630T1 (de) | 2001-12-15 |
CN1089335C (zh) | 2002-08-21 |
ITMI961204A1 (it) | 1997-12-13 |
ES2165610T3 (es) | 2002-03-16 |
IN182809B (ja) | 1999-07-24 |
CN1195338A (zh) | 1998-10-07 |
JP4018751B2 (ja) | 2007-12-05 |
WO1997047590A3 (en) | 1998-04-02 |
US5849953A (en) | 1998-12-15 |
NO980594L (no) | 1998-04-07 |
IT1288114B1 (it) | 1998-09-10 |
EP0851854A2 (en) | 1998-07-08 |
ZA975203B (en) | 1998-01-20 |
DE69709044D1 (de) | 2002-01-24 |
AU3094597A (en) | 1998-01-07 |
PT851854E (pt) | 2002-06-28 |
WO1997047590A2 (en) | 1997-12-18 |
HU227980B1 (en) | 2012-07-30 |
NO324342B1 (no) | 2007-09-24 |
IL123259A (en) | 2000-07-16 |
NO980594D0 (no) | 1998-02-11 |
IL123259A0 (en) | 1998-09-24 |
DE69709044T2 (de) | 2002-08-22 |
CZ293956B6 (cs) | 2004-08-18 |
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