JPH11505234A - 触媒の存在下で塩化チオニルによる塩素化により5−アミノ−2,4,6−トリヨードイソフタル酸二塩化物を製造する方法 - Google Patents
触媒の存在下で塩化チオニルによる塩素化により5−アミノ−2,4,6−トリヨードイソフタル酸二塩化物を製造する方法Info
- Publication number
- JPH11505234A JPH11505234A JP8534531A JP53453196A JPH11505234A JP H11505234 A JPH11505234 A JP H11505234A JP 8534531 A JP8534531 A JP 8534531A JP 53453196 A JP53453196 A JP 53453196A JP H11505234 A JPH11505234 A JP H11505234A
- Authority
- JP
- Japan
- Prior art keywords
- amino
- chloride
- triiodoisophthalic acid
- thionyl chloride
- triiodoisophthalic
- 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
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 32
- 230000008569 process Effects 0.000 title claims description 14
- 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 title abstract description 21
- 239000003054 catalyst Substances 0.000 title description 7
- 238000005660 chlorination reaction Methods 0.000 title description 6
- 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 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000005490 tosylate group Chemical group 0.000 claims abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 claims description 2
- SBHRWOBHKASWGU-UHFFFAOYSA-M tridodecyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CCCCCCCCCCCC SBHRWOBHKASWGU-UHFFFAOYSA-M 0.000 claims description 2
- QMADWSQEVHUFFJ-UHFFFAOYSA-N 2,4,5-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(I)=C(I)C(C(O)=O)=C1I QMADWSQEVHUFFJ-UHFFFAOYSA-N 0.000 claims 1
- UIZQXRXURRIARN-UHFFFAOYSA-N 2-iodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1I UIZQXRXURRIARN-UHFFFAOYSA-N 0.000 claims 1
- PBIDRTDEJPAXHY-UHFFFAOYSA-N 2-iodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1I PBIDRTDEJPAXHY-UHFFFAOYSA-N 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000002872 contrast media Substances 0.000 abstract description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- -1 tertiary amine salt Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- TZEBLZRSPJJCOS-UHFFFAOYSA-N 2,4,6-triiodo-5-(methylamino)benzene-1,3-dicarbonyl chloride Chemical compound CNC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I TZEBLZRSPJJCOS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- RERHJVNYJKZHLJ-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;2-(3,5-diiodo-4-oxopyridin-1-yl)acetate Chemical compound OCCNCCO.OC(=O)CN1C=C(I)C(=O)C(I)=C1 RERHJVNYJKZHLJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229960001025 iohexol Drugs 0.000 description 1
- 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 1
- 229960004647 iopamidol Drugs 0.000 description 1
- 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 description 1
- 229960004537 ioversol Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.適切な溶媒の存在下、塩化チオニルにより5−アミノ−2,4,6−トリ ヨードイソフタル酸を塩素化することによって、5−アミノ−2,4,6−トリ ヨードイソフタル酸二塩化物を製造する方法であって、触媒量の式(I): R1R2R3R4NX (I) (式中、Xはハロゲン、メシラート基又はトシラート基;R1、R2、R3及び R4は、同一又は異なって、R1、R2、R3及びR4基の炭素原子の総数が16を 越えるような、C1−C20アルキル基である)で示されるテトラアルキルアンモ ニウム塩の存在下で反応を実施することを特徴とする方法。 2.塩化チオニルの量が、5−アミノ−2,4,6−トリヨードイソフタル酸 に対して3〜4モルである、請求項1記載の方法。 3.式(I)のテトラアルキルアンモニウム塩が、5−アミノ−2,4,6− トリヨードイソフタル酸に対して0.3%〜10%のモル量である、請求項1記 載の方法。 4.テトラアルキルアンモニウム塩のモル量が、1%〜5%である、請求項3 記載の方法。 5.Xが塩素、臭素、メシラート基又はトシラート基;R1、R2、R3及びR4 が、同一又は異なって、炭素原子の総数が25〜38であるようなC1〜C20ア ルキル基を用いる、請求項1記載の方法。 6.式(I)のテトラアルキルアンモニウム塩が、トリオクチルメチルアンモ ニウム、メチルトリアルキル(C8〜C10)アンモニウム、ジオクタデシルジメ チルアンモニウム及びトリドデシルメチルアンモニウムの、塩化物、臭化物、メ シラート又はトシラートから選択される、請求項5記 載の方法。 7.トリオクチルメチルアンモニウムクロリド又はメチルトリアルキル(C8 〜C10)アンモニウムクロリドを用いる、請求項6記載の方法。 8.溶媒が、酢酸エチル、トルエン、塩化メチレン、1,2−ジクロロエタン 、酢酸イソプロピル及びその混合物から選択される、請求項1記載の方法。 9.溶媒がトルエンである、請求項8記載の方法。 10.請求項1記載の5−アミノ−2,4,6−トリヨードイソフタル酸二塩 化物の製造を含む、ヨーパミドール、ヨーヘキソール又はヨーベルソールの製造 方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI951004A IT1275429B (it) | 1995-05-18 | 1995-05-18 | Processo per la preparazione di un intermedio utile nella sintesi di composti organici |
IT95A001004 | 1995-05-18 | ||
PCT/EP1996/002009 WO1996036590A1 (en) | 1995-05-18 | 1996-05-10 | Process for the preparation of 5-amino-2,4,6-triiodoisophthalic acid dichloride by chlorination with thionyl chloride in the presence of a catalyst |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11505234A true JPH11505234A (ja) | 1999-05-18 |
JP3865405B2 JP3865405B2 (ja) | 2007-01-10 |
Family
ID=11371619
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53453196A Expired - Lifetime JP3865405B2 (ja) | 1995-05-18 | 1996-05-10 | 触媒の存在下で塩化チオニルによる塩素化により5−アミノ−2,4,6−トリヨードイソフタル酸二塩化物を製造する方法 |
Country Status (20)
Country | Link |
---|---|
US (1) | US5663432A (ja) |
JP (1) | JP3865405B2 (ja) |
AU (1) | AU5895096A (ja) |
BE (1) | BE1009466A3 (ja) |
CA (1) | CA2221278C (ja) |
CH (1) | CH691534A5 (ja) |
CZ (1) | CZ287815B6 (ja) |
DE (1) | DE19681399B4 (ja) |
DK (1) | DK176046B1 (ja) |
FR (1) | FR2734262B1 (ja) |
GB (1) | GB2315751B (ja) |
HU (1) | HUP9801142A3 (ja) |
IE (1) | IE80674B1 (ja) |
IL (1) | IL118062A (ja) |
IT (1) | IT1275429B (ja) |
NL (1) | NL1003127C2 (ja) |
NO (1) | NO310286B1 (ja) |
SE (1) | SE520616C2 (ja) |
WO (1) | WO1996036590A1 (ja) |
ZA (1) | ZA963788B (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014527510A (ja) * | 2011-06-24 | 2014-10-16 | ホビオネ インテル リミテッド | トリヨード造影剤の製造 |
CN108026017A (zh) * | 2015-10-02 | 2018-05-11 | 日本瑞翁株式会社 | 酰卤溶液的制造方法、混合溶液及单酯化合物的制造方法 |
KR20180101396A (ko) | 2016-01-26 | 2018-09-12 | 니폰 제온 가부시키가이샤 | 산 할라이드 용액의 제조 방법, 및 모노에스테르 화합물의 제조 방법 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101307010B (zh) * | 2008-07-12 | 2011-05-25 | 厦门大学 | 碘佛醇的合成方法 |
CA2897700C (en) | 2012-12-11 | 2022-05-03 | Bracco Imaging S.P.A. | Continuous process for the preparation of (s)-2-acetyloxypropionic acid chloride |
SI3154928T1 (sl) | 2014-06-10 | 2020-06-30 | Bracco Imaging S.P.A. | Postopek za pripravo (S)-2-acetiloksipropionske kisline in njenih derivatov |
US10342232B1 (en) | 2018-10-24 | 2019-07-09 | The United States Of America As Represented By The Secretary Of The Navy | Iodinated polymers for biological agent defeat |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR825418A (fr) * | 1936-08-10 | 1938-03-03 | Bosch Robert | Pompe à combustibles liquides |
US3655752A (en) * | 1969-06-20 | 1972-04-11 | Sterling Drug Inc | Isomers of 2 4 6-trihalo-n n n' n'-tetraalkylisophthalamides |
CH608189A5 (ja) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
GB1548594A (en) * | 1976-06-11 | 1979-07-18 | Nyegaard & Co As | Triiodoisophthalic acid amides |
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 |
US4396598A (en) * | 1982-01-11 | 1983-08-02 | Mallinckrodt, Inc. | Triiodoisophthalamide X-ray contrast agent |
FR2541676A1 (fr) * | 1983-02-25 | 1984-08-31 | Guerbet Sa | Composes non-ioniques a structures benzenique iodee ou bromee et produits opacifiants en contenant |
US5075502A (en) * | 1989-12-13 | 1991-12-24 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
CA2124559A1 (en) * | 1991-12-03 | 1993-06-10 | Mills Thomas Kneller | Nonionic x-ray contrast agents, compositions and methods |
IT1271107B (it) * | 1994-11-29 | 1997-05-26 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di composti organici |
-
1995
- 1995-05-18 IT ITMI951004A patent/IT1275429B/it active IP Right Grant
-
1996
- 1996-04-29 IL IL11806296A patent/IL118062A/xx not_active IP Right Cessation
- 1996-05-09 FR FR9605773A patent/FR2734262B1/fr not_active Expired - Lifetime
- 1996-05-10 JP JP53453196A patent/JP3865405B2/ja not_active Expired - Lifetime
- 1996-05-10 GB GB9724181A patent/GB2315751B/en not_active Expired - Lifetime
- 1996-05-10 CH CH02665/97A patent/CH691534A5/de not_active IP Right Cessation
- 1996-05-10 CA CA002221278A patent/CA2221278C/en not_active Expired - Lifetime
- 1996-05-10 CZ CZ19973633A patent/CZ287815B6/cs not_active IP Right Cessation
- 1996-05-10 AU AU58950/96A patent/AU5895096A/en not_active Abandoned
- 1996-05-10 DE DE19681399T patent/DE19681399B4/de not_active Expired - Lifetime
- 1996-05-10 DK DK199701303A patent/DK176046B1/da not_active IP Right Cessation
- 1996-05-10 HU HU9801142A patent/HUP9801142A3/hu unknown
- 1996-05-10 WO PCT/EP1996/002009 patent/WO1996036590A1/en active IP Right Grant
- 1996-05-13 ZA ZA963788A patent/ZA963788B/xx unknown
- 1996-05-15 NL NL1003127A patent/NL1003127C2/nl not_active IP Right Cessation
- 1996-05-17 US US08/649,490 patent/US5663432A/en not_active Expired - Lifetime
- 1996-05-17 IE IE960350A patent/IE80674B1/en not_active IP Right Cessation
- 1996-05-20 BE BE9600446A patent/BE1009466A3/fr not_active IP Right Cessation
-
1997
- 1997-11-17 NO NO19975260A patent/NO310286B1/no not_active IP Right Cessation
- 1997-11-17 SE SE9704190A patent/SE520616C2/sv unknown
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014527510A (ja) * | 2011-06-24 | 2014-10-16 | ホビオネ インテル リミテッド | トリヨード造影剤の製造 |
CN108026017A (zh) * | 2015-10-02 | 2018-05-11 | 日本瑞翁株式会社 | 酰卤溶液的制造方法、混合溶液及单酯化合物的制造方法 |
KR20180064393A (ko) | 2015-10-02 | 2018-06-14 | 니폰 제온 가부시키가이샤 | 산 할라이드 용액의 제조 방법, 혼합 용액, 및 모노에스테르 화합물의 제조 방법 |
US10508072B2 (en) | 2015-10-02 | 2019-12-17 | Zeon Corporation | Method for producing acid halide solution, mixed solution, and method for producing monoester compound |
CN108026017B (zh) * | 2015-10-02 | 2021-09-21 | 日本瑞翁株式会社 | 酰卤溶液的制造方法、混合溶液及单酯化合物的制造方法 |
KR20180101396A (ko) | 2016-01-26 | 2018-09-12 | 니폰 제온 가부시키가이샤 | 산 할라이드 용액의 제조 방법, 및 모노에스테르 화합물의 제조 방법 |
US10633323B2 (en) | 2016-01-26 | 2020-04-28 | Zeon Corporation | Method of producing acid halide solution and method of producing monoester compound |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH11505234A (ja) | 触媒の存在下で塩化チオニルによる塩素化により5−アミノ−2,4,6−トリヨードイソフタル酸二塩化物を製造する方法 | |
US5763650A (en) | Process for the preparation of a halosubstituted aromatic acid | |
JP3795524B2 (ja) | 第三級アミン塩又は第四級アンモニウム塩の存在下対応する酸の塩素化による5−アミノ−2,4,6−トリヨードイソフタル酸ジクロライドの製造法 | |
JP4219409B2 (ja) | 5―アミノ―2,4,6―トリヨード―1,3―ベンゼンジカルボン酸誘導体を製造する方法 | |
JP4039700B2 (ja) | トリヨードベンゼン化合物の製造 | |
WO2012175903A1 (en) | Manufacture of a triiodinated contrast agent | |
JP4035198B2 (ja) | ヨウ素化造影剤の合成に有用な中間体の製造方法 | |
JP2574667B2 (ja) | 新規なフルオル化されたo−ジアミノベンゾ−1,4−ジオキセン | |
JP3390476B2 (ja) | ハロゲンアントラニル酸の製造方法 | |
KR20150047997A (ko) | 이오프로마이드의 중간체의 제조방법 | |
JP4842469B2 (ja) | 2−アミノ−3−カルボキシ−1,4−ナフトキノンの製造法 | |
JP3438084B2 (ja) | 3,4−ジクロロベンゾニトリルの製造法 | |
WO2005014531A1 (ja) | N-メタクリロイル-4-シアノ-3-トリフルオロメチルアニリンの製造方法、該化合物の安定化方法およびビカルタミドの製造方法 | |
JPS6054948B2 (ja) | α,β↓−不飽和環状脂肪族ケトキシムから芳香族アミンを製造する方法 | |
JPH0853400A (ja) | ヒドロキシカルボキシアニリドの製造方法 | |
JP3508214B2 (ja) | 1−アミノアントラキノン類の製造方法 | |
JPH11158159A (ja) | 5−パーフルオロアルキル−5−ブロモ−6−ヒドロウラシル類の製造方法 | |
JPH06329658A (ja) | クロメン誘導体およびその製法 | |
JPH041159A (ja) | 2,6―ジハロゲノアニリンの製造方法 | |
JPH01272556A (ja) | 4‐アリル‐2,6‐ジエチルアニリン及びその製造法 | |
JPS6344556A (ja) | N−(3,4−ジメトキシシンナモイル)アントラニル酸の製造方法 | |
JPH0211536A (ja) | 2,4−ジヒドロキシアセトフェノンの製造法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20040227 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20060905 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20061003 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091013 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101013 Year of fee payment: 4 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111013 Year of fee payment: 5 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121013 Year of fee payment: 6 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131013 Year of fee payment: 7 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |