NL1003127C2 - Werkwijze voor het bereiden van 5-amino-2,4,6-trijodoisoftaalzuur- dichloride. - Google Patents

Werkwijze voor het bereiden van 5-amino-2,4,6-trijodoisoftaalzuur- dichloride. Download PDF

Info

Publication number: NL1003127C2
Authority: NL; Netherlands
Prior art keywords: amino; ammonium; triiodoisophthalic; dichloride; carbon atoms
Prior art date: 1995-05-18

Application number

NL1003127A

Other languages

English (en)

Dutch (nl)

Other versions

NL1003127A1 (nl

Inventor

Graziano Castaldi

Marco Villa

Claudio Pozzoli

Lauro Russo

Original Assignee

Bracco Int Bv

Priority date (The priority date 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 date listed.)

1995-05-18

Filing date

1996-05-15

Publication date

1999-08-25

1996-05-15 Application filed by Bracco Int Bv filed Critical Bracco Int Bv

1996-11-19 Publication of NL1003127A1 publication Critical patent/NL1003127A1/xx

1999-08-25 Application granted granted Critical

1999-08-25 Publication of NL1003127C2 publication Critical patent/NL1003127C2/nl

Links

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 claims description 13
238000004519 manufacturing process Methods 0.000 title claims 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 44
238000000034 method Methods 0.000 claims description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 16
150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 14
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 description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
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
230000008569 process Effects 0.000 claims description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
230000003197 catalytic effect Effects 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
238000005660 chlorination reaction Methods 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
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 6
125000000217 alkyl group Chemical group 0.000 claims description 5
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
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
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 2
235000019270 ammonium chloride Nutrition 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
150000001649 bromium compounds Chemical class 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 2
229960001025 iohexol Drugs 0.000 claims description 2
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 claims description 2
229960004647 iopamidol Drugs 0.000 claims description 2
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 description 2
229960004537 ioversol Drugs 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 class [Cl-].CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CCCCCCCCCCCC SBHRWOBHKASWGU-UHFFFAOYSA-M 0.000 claims description 2
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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
238000004090 dissolution Methods 0.000 claims 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
238000010992 reflux 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
239000002253 acid Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000002955 isolation Methods 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
230000008901 benefit Effects 0.000 description 3
239000000193 iodinated contrast media Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
241000234282 Allium Species 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method 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
230000009467 reduction Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
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
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
101100520151 Mus musculus Pirt gene Proteins 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
229960003237 betaine Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 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
150000002894 organic compounds Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000005490 tosylate group Chemical group 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Indole Compounds (AREA)

NL1003127A 1995-05-18 1996-05-15 Werkwijze voor het bereiden van 5-amino-2,4,6-trijodoisoftaalzuur- dichloride. NL1003127C2 (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ITMI951004		1995-05-18
ITMI951004A IT1275429B (it)	1995-05-18	1995-05-18	Processo per la preparazione di un intermedio utile nella sintesi di composti organici

Publications (2)

Publication Number	Publication Date
NL1003127A1 NL1003127A1 (nl)	1996-11-19
NL1003127C2 true NL1003127C2 (nl)	1999-08-25

Family

ID=11371619

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1003127A NL1003127C2 (nl)	1995-05-18	1996-05-15	Werkwijze voor het bereiden van 5-amino-2,4,6-trijodoisoftaalzuur- dichloride.

Country Status (20)

Country	Link
US (1)	US5663432A (cs)
JP (1)	JP3865405B2 (cs)
AU (1)	AU5895096A (cs)
BE (1)	BE1009466A3 (cs)
CA (1)	CA2221278C (cs)
CH (1)	CH691534A5 (cs)
CZ (1)	CZ287815B6 (cs)
DE (1)	DE19681399B4 (cs)
DK (1)	DK176046B1 (cs)
FR (1)	FR2734262B1 (cs)
GB (1)	GB2315751B (cs)
HU (1)	HUP9801142A3 (cs)
IE (1)	IE80674B1 (cs)
IL (1)	IL118062A (cs)
IT (1)	IT1275429B (cs)
NL (1)	NL1003127C2 (cs)
NO (1)	NO310286B1 (cs)
SE (1)	SE520616C2 (cs)
WO (1)	WO1996036590A1 (cs)
ZA (1)	ZA963788B (cs)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
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
PT105770B (pt) *	2011-06-24	2013-07-08	Hovione Farmaciencia S A	Novo intermediário e seu uso na preparação de agente de contrate triiodado
KR102044772B1 (ko)	2012-12-11	2019-11-14	브라코 이미징 에스.피.에이.	(s)-2-아세틸옥시프로피온산 클로라이드의 제조를 위한 연속식 공정
LT3154928T (lt)	2014-06-10	2020-05-11	Bracco Imaging S.P.A.	(s)-2-acetiloksipropioninės rūgšties ir jos darinių gavimo būdas
JP6787331B2 (ja)	2015-10-02	2020-11-18	日本ゼオン株式会社	酸ハライド溶液の製造方法、混合溶液、及びモノエステル化合物の製造方法
US10633323B2 (en)	2016-01-26	2020-04-28	Zeon Corporation	Method of producing acid halide solution and method of producing monoester compound
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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0026281A1 (de) *	1979-08-09	1981-04-08	BRACCO INDUSTRIA CHIMICA Società per Azioni	Neue Derivate der 2,4,6-Trijod-isophthalsäure, Verfahren zu deren Herstellung und diese enthaltende Röntgenkontrastmittel
EP0118347A1 (fr) *	1983-02-25	1984-09-12	Guerbet S.A.	Composés non-ioniques à structure benzénique iodée ou bromée et produits opacifiants en contenant
WO1991009007A2 (en) *	1989-12-13	1991-06-27	Mallinckrodt, Inc.	Nonionic x-ray contrast agents, compositions and methods
WO1996016927A1 (en) *	1994-11-29	1996-06-06	Zambon Group S.P.A.	Process for preparing 5-amino-2,4,6-triiodoisophthalic acid dichloride by chlorination of the corresponding acid in the presence of a tertiary amine salt or quarternary ammonium salt

Family Cites Families (6)

* Cited by examiner, † Cited by third party
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 (cs) *	1974-12-13	1978-12-29	Savac Ag
GB1548594A (en) *	1976-06-11	1979-07-18	Nyegaard & Co As	Triiodoisophthalic acid amides
US4396598A (en) *	1982-01-11	1983-08-02	Mallinckrodt, Inc.	Triiodoisophthalamide X-ray contrast agent
WO1993010825A1 (en) *	1991-12-03	1993-06-10	Mallinckrodt Medical, Inc.	Nonionic x-ray contrast agents, compositions and methods

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 WO PCT/EP1996/002009 patent/WO1996036590A1/en not_active Ceased
- 1996-05-10 DK DK199701303A patent/DK176046B1/da not_active IP Right Cessation
- 1996-05-10 CZ CZ19973633A patent/CZ287815B6/cs not_active IP Right Cessation
- 1996-05-10 CH CH02665/97A patent/CH691534A5/de not_active IP Right Cessation
- 1996-05-10 JP JP53453196A patent/JP3865405B2/ja not_active Expired - Lifetime
- 1996-05-10 DE DE19681399T patent/DE19681399B4/de not_active Expired - Lifetime
- 1996-05-10 HU HU9801142A patent/HUP9801142A3/hu unknown
- 1996-05-10 GB GB9724181A patent/GB2315751B/en not_active Expired - Lifetime
- 1996-05-10 AU AU58950/96A patent/AU5895096A/en not_active Abandoned
- 1996-05-10 CA CA002221278A patent/CA2221278C/en not_active Expired - Lifetime
- 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 IE IE960350A patent/IE80674B1/en not_active IP Right Cessation
- 1996-05-17 US US08/649,490 patent/US5663432A/en not_active Expired - Lifetime
- 1996-05-20 BE BE9600446A patent/BE1009466A3/fr not_active IP Right Cessation
1997
- 1997-11-17 SE SE9704190A patent/SE520616C2/sv unknown
- 1997-11-17 NO NO19975260A patent/NO310286B1/no not_active IP Right Cessation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0026281A1 (de) *	1979-08-09	1981-04-08	BRACCO INDUSTRIA CHIMICA Società per Azioni	Neue Derivate der 2,4,6-Trijod-isophthalsäure, Verfahren zu deren Herstellung und diese enthaltende Röntgenkontrastmittel
EP0118347A1 (fr) *	1983-02-25	1984-09-12	Guerbet S.A.	Composés non-ioniques à structure benzénique iodée ou bromée et produits opacifiants en contenant
WO1991009007A2 (en) *	1989-12-13	1991-06-27	Mallinckrodt, Inc.	Nonionic x-ray contrast agents, compositions and methods
WO1996016927A1 (en) *	1994-11-29	1996-06-06	Zambon Group S.P.A.	Process for preparing 5-amino-2,4,6-triiodoisophthalic acid dichloride by chlorination of the corresponding acid in the presence of a tertiary amine salt or quarternary ammonium salt

Also Published As

Publication number	Publication date
ITMI951004A1 (it)	1996-11-18
JP3865405B2 (ja)	2007-01-10
CZ363397A3 (cs)	1998-04-15
IT1275429B (it)	1997-08-07
FR2734262A1 (fr)	1996-11-22
JPH11505234A (ja)	1999-05-18
IL118062A (en)	2001-03-19
DK130397A (da)	1997-11-17
US5663432A (en)	1997-09-02
SE9704190D0 (sv)	1997-11-17
NL1003127A1 (nl)	1996-11-19
WO1996036590A1 (en)	1996-11-21
DK176046B1 (da)	2006-02-20
GB2315751B (en)	1999-04-14
GB2315751A (en)	1998-02-11
DE19681399T1 (de)	1998-05-20
ZA963788B (en)	1996-09-05
GB9724181D0 (en)	1998-01-14
CH691534A5 (de)	2001-08-15
IE80674B1 (en)	1998-11-18
FR2734262B1 (fr)	1997-08-29
ITMI951004A0 (it)	1995-05-18
CA2221278A1 (en)	1996-11-21
SE520616C2 (sv)	2003-07-29
AU5895096A (en)	1996-11-29
NO310286B1 (no)	2001-06-18
NO975260D0 (no)	1997-11-17
HUP9801142A3 (en)	1998-09-28
CZ287815B6 (en)	2001-02-14
NO975260L (no)	1997-11-17
SE9704190L (sv)	1997-11-17
IE960350A1 (en)	1996-11-27
IL118062A0 (en)	1996-08-04
DE19681399B4 (de)	2008-08-28
CA2221278C (en)	2008-12-02
BE1009466A3 (fr)	1997-04-01
HUP9801142A1 (hu)	1998-08-28

Legal Events

Date	Code	Title	Description
1997-01-06	AD1A	A request for search or an international type search has been filed
1998-09-01	CD	Transfer of rights (laid open patent application)	Free format text: BRACCO INTERNATIONAL B.V.
1999-08-02	RD2N	Patents in respect of which a decision has been taken or a report has been made (novelty report)	Effective date: 19990624
2004-02-02	SD	Assignments of patents	Owner name: BRACCO IMAGING S.P.A.
2016-05-18	MK	Patent expired because of reaching the maximum lifetime of a patent	Effective date: 20160514

Publication	Publication Date	Title
NL1003127C2 (nl)	1999-08-25	Werkwijze voor het bereiden van 5-amino-2,4,6-trijodoisoftaalzuur- dichloride.
JP6618569B2 (ja)	2019-12-11	キラルキヌレニン化合物の合成方法
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US5856570A (en)	1999-01-05	Process for preparing 5-amino-2,4,6-triiodoisophthalic acid dichloride by chlorination of the corresponding acid in the presence of a tertiary amine salt or quaternary ammonium salt
JP4439123B2 (ja)	2010-03-24	Ｎ，ｎ′−ビス〔２，３−ジヒドロキシプロピル〕−５−〔（ヒドロキシアセチル）メチルアミノ〕−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
CA2755650C (en)	2013-12-03	Process for the preparation of triiodinated carboxylic aromatic derivatives
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