JP2000517313A - 造影剤の製法 - Google Patents
造影剤の製法Info
- Publication number
- JP2000517313A JP2000517313A JP10511401A JP51140198A JP2000517313A JP 2000517313 A JP2000517313 A JP 2000517313A JP 10511401 A JP10511401 A JP 10511401A JP 51140198 A JP51140198 A JP 51140198A JP 2000517313 A JP2000517313 A JP 2000517313A
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- phenyl
- acid derivative
- amino
- corresponding amino
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 239000002872 contrast media Substances 0.000 title claims description 10
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 38
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 26
- 230000010933 acylation Effects 0.000 claims abstract description 20
- 238000005917 acylation reaction Methods 0.000 claims abstract description 20
- 238000007126 N-alkylation reaction Methods 0.000 claims abstract description 16
- 239000002168 alkylating agent Substances 0.000 claims abstract description 11
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 15
- -1 iodophenyl compound Chemical class 0.000 claims description 13
- 229960000824 iopentol Drugs 0.000 claims description 12
- IUNJANQVIJDFTQ-UHFFFAOYSA-N iopentol Chemical compound COCC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I IUNJANQVIJDFTQ-UHFFFAOYSA-N 0.000 claims description 12
- 229960004359 iodixanol Drugs 0.000 claims description 10
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- RHISTIGVAKTTCM-UHFFFAOYSA-N 5-[[3-[3,5-bis(1,3-dihydroxypropan-2-ylcarbamoyl)-n-(2-hydroxyethyl)-2,4,6-triiodoanilino]-3-oxopropanoyl]-(2-hydroxyethyl)amino]-1-n,3-n-bis(1,3-dihydroxypropan-2-yl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound IC=1C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C(I)C=1N(CCO)C(=O)CC(=O)N(CCO)C1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I RHISTIGVAKTTCM-UHFFFAOYSA-N 0.000 claims description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 3
- XUHXFSYUBXNTHU-UHFFFAOYSA-N Iotrolan Chemical compound IC=1C(C(=O)NC(CO)C(O)CO)=C(I)C(C(=O)NC(CO)C(O)CO)=C(I)C=1N(C)C(=O)CC(=O)N(C)C1=C(I)C(C(=O)NC(CO)C(O)CO)=C(I)C(C(=O)NC(CO)C(O)CO)=C1I XUHXFSYUBXNTHU-UHFFFAOYSA-N 0.000 claims description 3
- AMDBBAQNWSUWGN-UHFFFAOYSA-N Ioversol Chemical compound OCCN(C(=O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I AMDBBAQNWSUWGN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 229950002407 iodecimol Drugs 0.000 claims description 3
- 229960000780 iomeprol Drugs 0.000 claims description 3
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 claims description 3
- 229960003182 iotrolan Drugs 0.000 claims description 3
- 229960004537 ioversol Drugs 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229960001025 iohexol Drugs 0.000 description 9
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FOLYKNXDLNPWGC-UHFFFAOYSA-N 1-chloro-3-methoxypropan-2-ol Chemical compound COCC(O)CCl FOLYKNXDLNPWGC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KAEGSAWWVYMWIQ-UHFFFAOYSA-N 5-amino-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I KAEGSAWWVYMWIQ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- DGNHGHNYQRBKMC-UHFFFAOYSA-N 1-chloro-3-methoxypropan-1-ol Chemical compound COCCC(O)Cl DGNHGHNYQRBKMC-UHFFFAOYSA-N 0.000 description 1
- KFIQRSOQSOSKOM-UHFFFAOYSA-N 1-n,3-n-bis(2,3-dihydroxypropyl)-5-(2-hydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound CC(O)CC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I KFIQRSOQSOSKOM-UHFFFAOYSA-N 0.000 description 1
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 1
- LDOMKUVUXZRECL-UHFFFAOYSA-N 2-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(C(O)=O)C=CC=C1C(O)=O LDOMKUVUXZRECL-UHFFFAOYSA-N 0.000 description 1
- PXDUXZQJUFJWEA-UHFFFAOYSA-N 4-[acetyl(2,3-dihydroxypropyl)amino]-1-n,2-n-bis(2,3-dihydroxypropyl)-1,3,5-triiodocyclohexa-3,5-diene-1,2-dicarboxamide Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)C(I)(C(=O)NCC(O)CO)C=C1I PXDUXZQJUFJWEA-UHFFFAOYSA-N 0.000 description 1
- DGIJJAHTRAQISB-UHFFFAOYSA-N 4-acetamido-1-n,2-n-bis(2,3-dihydroxypropyl)-1,3,5-triiodocyclohexa-3,5-diene-1,2-dicarboxamide Chemical compound CC(=O)NC1=C(I)C(C(=O)NCC(O)CO)C(I)(C(=O)NCC(O)CO)C=C1I DGIJJAHTRAQISB-UHFFFAOYSA-N 0.000 description 1
- TWPRBHMFCUHAGA-UHFFFAOYSA-N 4-amino-1-n,2-n-bis(2,3-dihydroxypropyl)-1,3,5-triiodocyclohexa-3,5-diene-1,2-dicarboxamide Chemical compound NC1=C(I)C(C(=O)NCC(O)CO)C(I)(C(=O)NCC(O)CO)C=C1I TWPRBHMFCUHAGA-UHFFFAOYSA-N 0.000 description 1
- BKLPQLGRQLUPQT-UHFFFAOYSA-N 6-(2,3-dihydroxypropyl)-1,3,5-triiodocyclohexa-3,5-diene-1,2-dicarboxamide Chemical compound NC(=O)C1C(I)=CC(I)=C(CC(O)CO)C1(I)C(N)=O BKLPQLGRQLUPQT-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940126534 drug product Drugs 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
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000006303 iodophenyl group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Steroid Compounds (AREA)
- Glass Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.相当するアミノ−フェニル−カルボン酸(またはカルボン酸誘導体)の液相 アシル化および次のN−アルキル化によってN−アルキル−アシルアミノ−フェ ニル−カルボン酸またはカルボン酸誘導体を製造する方法において、アルキル化 剤をアシル化の反応生成物を含有する溶液に加えてN−アルキル化を行うことか らなる改良。 2.相当するアミノ−フェニルカルボン酸(またはカルボン酸誘導体)がフェニ ル環上に合計3個のアミノおよびカルボキシル基を有する化合物である請求項1 記載の方法。 3.相当するアミノ−フェニル−カルボン酸(またはカルボン酸誘導体)がトリ ヨードフェニル化合物である請求項1記載の方法。 4.相当するアミノ−フェニル−カルボン酸(またはカルボン酸誘導体)がアル キルアミノ−カルボニル−トリヨードフェニル化合物である請求項1記載の方法 。 5.相当するアミノ−フェニル−カルボン酸(またはカルボン酸誘導体)が2,4, 6−トリヨード−2,5−ビス(アルキルアミノ−カルボニル)−アニリンである請 求項1記載の方法。 6.相当するアミノ−フェニル−カルボン酸(またはカルボン酸誘導体)が5− アミノ−N,N'−ビス(2,3−ジヒドロキシプロピル)−2,4,6−トリヨードフタル アミドである請求項1記載の方法。 7.相当するアミノ−フェニル−カルボン酸(またはカルボン酸誘導体)が、1 個または2個以上のヒドロキシル基を有しそして6個までの炭素原子を含有する アルキルアミノカルボニル基を含有する請求項1記載の方法。 8.アシル化を酸ハロゲン化物または無水酢酸を使用して行なう請求項1 記載の方法。 9.アルキル化剤が、1−ハロ−2,3−プロパンジオール、グリシドール、1− ハロ−3−メトキシ−2−プロパノール、1,3−ハロ−2−プロパノールおよび エピクロロヒドリンからなる群から選択されたものである請求項1記載の方法。 10.アミノ−フェニル−カルボン酸(またはカルボン酸誘導体)を液相において アシル化し、アシル化された生成物を塩基加水分解して得られたN−アシル−ア ミノ中間体からO−アシル基を除去しそして液相を塩基性のpHに維持し、該アシ ルアミノ中間体をN−アルキル化することからなるN−アルキル−アシルアミノ −フェニル−カルボン酸またはカルボン酸誘導体化合物を製造する方法。 11.イオメプロール、イオベルソール、イオキシラン、イオトロラン、イオキサ グレート、イオデシモール、2−イオピロール、2−イオピペリドール、イオヘ キソール、イオペントールおよびイオジキサノールからなる群からの選択された 造影剤の製法である請求項1または10記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9618055.9A GB9618055D0 (en) | 1996-08-29 | 1996-08-29 | Process |
GB9618055.9 | 1996-08-29 | ||
PCT/GB1997/002335 WO1998008805A1 (en) | 1996-08-29 | 1997-08-29 | Process for the preparation of contrast agents |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2000517313A true JP2000517313A (ja) | 2000-12-26 |
JP2000517313A5 JP2000517313A5 (ja) | 2005-04-07 |
JP4113587B2 JP4113587B2 (ja) | 2008-07-09 |
Family
ID=10799119
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51140198A Expired - Lifetime JP4113587B2 (ja) | 1996-08-29 | 1997-08-29 | 造影剤の製法 |
Country Status (21)
Country | Link |
---|---|
EP (1) | EP0923537B1 (ja) |
JP (1) | JP4113587B2 (ja) |
KR (1) | KR100539647B1 (ja) |
CN (1) | CN1092182C (ja) |
AT (1) | ATE207880T1 (ja) |
AU (1) | AU717842B2 (ja) |
BG (1) | BG103288A (ja) |
BR (1) | BR9711358A (ja) |
CA (1) | CA2263426A1 (ja) |
CZ (1) | CZ296230B6 (ja) |
DE (1) | DE69707901T2 (ja) |
EE (1) | EE9900081A (ja) |
ES (1) | ES2167014T3 (ja) |
GB (1) | GB9618055D0 (ja) |
HU (1) | HUP9903852A3 (ja) |
IL (1) | IL128685A0 (ja) |
NO (1) | NO322141B1 (ja) |
NZ (1) | NZ334818A (ja) |
PL (1) | PL193698B1 (ja) |
SK (1) | SK26399A3 (ja) |
WO (1) | WO1998008805A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000517312A (ja) * | 1996-08-29 | 2000-12-26 | ニユコメド・イメージング・アクシエセルカペト | イオヘキソールの製法 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9903109D0 (en) | 1999-02-11 | 1999-04-07 | Nycomed Imaging As | Process |
ITMI20010773A1 (it) * | 2001-04-11 | 2002-10-11 | Chemi Spa | Processo per la produzione di ioexolo ad elevata purezza |
CN100344606C (zh) * | 2005-12-28 | 2007-10-24 | 江苏省原子医学研究所 | 一种碘昔兰的制备方法 |
US20110021822A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | continuous deacetylation and purification process in synthesis of non-ionic x-ray contrast agents |
CN103058880B (zh) * | 2011-10-21 | 2015-08-05 | 连云港润众制药有限公司 | 碘克沙醇及其合成中间体的制备方法 |
PT3077368T (pt) * | 2013-12-06 | 2018-10-19 | Ge Healthcare As | Processo alternativo para a purificação de um intermediário na síntese de agentes de contraste não iónicos para raios-x |
WO2015082718A1 (en) * | 2013-12-06 | 2015-06-11 | Ge Healthcare As | Alternative process for the purification of an intermediate in the synthesis of non-ionic x-ray contrast agents |
CN104356023B (zh) * | 2014-10-29 | 2016-04-13 | 武汉工程大学 | 一种碘曲仑的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5321137A (en) * | 1976-06-11 | 1978-02-27 | Serukapeto | Xxray contrast medium |
JPS5982355A (ja) * | 1982-10-01 | 1984-05-12 | ニユエガ−ド・アンド・コンパニ−・アクシエ/セルカペト | X線造影剤 |
Family Cites Families (3)
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FR2132530B1 (ja) * | 1971-04-07 | 1974-08-02 | Guerbet Lab Andre | |
US4584401A (en) * | 1983-10-20 | 1986-04-22 | Biophysica Foundation | Methods and compositions involving polyhydroxylated polyiodo non-ionic contrast media |
AU600672B2 (en) * | 1985-08-09 | 1990-08-23 | Guerbet Llc | 2,4,6-triiodo-isophthalamides in x-ray imaging |
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1996
- 1996-08-29 GB GBGB9618055.9A patent/GB9618055D0/en active Pending
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1997
- 1997-08-29 JP JP51140198A patent/JP4113587B2/ja not_active Expired - Lifetime
- 1997-08-29 DE DE69707901T patent/DE69707901T2/de not_active Expired - Lifetime
- 1997-08-29 HU HU9903852A patent/HUP9903852A3/hu unknown
- 1997-08-29 KR KR10-1999-7001685A patent/KR100539647B1/ko active IP Right Grant
- 1997-08-29 CA CA002263426A patent/CA2263426A1/en not_active Abandoned
- 1997-08-29 PL PL97331821A patent/PL193698B1/pl unknown
- 1997-08-29 ES ES97937743T patent/ES2167014T3/es not_active Expired - Lifetime
- 1997-08-29 EP EP97937743A patent/EP0923537B1/en not_active Expired - Lifetime
- 1997-08-29 IL IL12868597A patent/IL128685A0/xx unknown
- 1997-08-29 AT AT97937743T patent/ATE207880T1/de not_active IP Right Cessation
- 1997-08-29 CZ CZ0067099A patent/CZ296230B6/cs not_active IP Right Cessation
- 1997-08-29 AU AU40267/97A patent/AU717842B2/en not_active Ceased
- 1997-08-29 NZ NZ334818A patent/NZ334818A/xx unknown
- 1997-08-29 CN CN97197523A patent/CN1092182C/zh not_active Expired - Lifetime
- 1997-08-29 SK SK263-99A patent/SK26399A3/sk unknown
- 1997-08-29 BR BR9711358A patent/BR9711358A/pt not_active Application Discontinuation
- 1997-08-29 WO PCT/GB1997/002335 patent/WO1998008805A1/en active IP Right Grant
- 1997-08-29 EE EEP199900081A patent/EE9900081A/xx unknown
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1999
- 1999-02-25 NO NO19990890A patent/NO322141B1/no not_active IP Right Cessation
- 1999-03-26 BG BG103288A patent/BG103288A/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5321137A (en) * | 1976-06-11 | 1978-02-27 | Serukapeto | Xxray contrast medium |
JPS5982355A (ja) * | 1982-10-01 | 1984-05-12 | ニユエガ−ド・アンド・コンパニ−・アクシエ/セルカペト | X線造影剤 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2000517312A (ja) * | 1996-08-29 | 2000-12-26 | ニユコメド・イメージング・アクシエセルカペト | イオヘキソールの製法 |
Also Published As
Publication number | Publication date |
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CN1228762A (zh) | 1999-09-15 |
ATE207880T1 (de) | 2001-11-15 |
WO1998008805A1 (en) | 1998-03-05 |
AU4026797A (en) | 1998-03-19 |
CZ67099A3 (cs) | 1999-08-11 |
DE69707901D1 (de) | 2001-12-06 |
DE69707901T2 (de) | 2002-07-18 |
HUP9903852A3 (en) | 2001-08-28 |
NO322141B1 (no) | 2006-08-21 |
BG103288A (en) | 2000-01-31 |
ES2167014T3 (es) | 2002-05-01 |
KR100539647B1 (ko) | 2005-12-29 |
HUP9903852A2 (hu) | 2000-03-28 |
JP4113587B2 (ja) | 2008-07-09 |
BR9711358A (pt) | 1999-08-17 |
CA2263426A1 (en) | 1998-03-05 |
PL331821A1 (en) | 1999-08-02 |
GB9618055D0 (en) | 1996-10-09 |
AU717842B2 (en) | 2000-04-06 |
EP0923537B1 (en) | 2001-10-31 |
PL193698B1 (pl) | 2007-03-30 |
IL128685A0 (en) | 2000-01-31 |
NZ334818A (en) | 2000-08-25 |
CZ296230B6 (cs) | 2006-02-15 |
EE9900081A (et) | 1999-10-15 |
NO990890D0 (no) | 1999-02-25 |
NO990890L (no) | 1999-02-25 |
KR20000035944A (ko) | 2000-06-26 |
EP0923537A1 (en) | 1999-06-23 |
CN1092182C (zh) | 2002-10-09 |
SK26399A3 (en) | 2000-03-13 |
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