NO314257B1 - Fremgangsmåte ved fremstilling av en halogen-substituert aromatisk syre - Google Patents

Fremgangsmåte ved fremstilling av en halogen-substituert aromatisk syre Download PDF

Info

Publication number: NO314257B1
Authority: NO; Norway
Prior art keywords: benzenedicarboxylic acid; amino; hcl; solution; acid
Prior art date: 1995-05-23

Application number

NO19970263A

Other languages

English (en)

Norwegian (no)

Other versions

NO970263L (no

NO970263D0 (no

Inventor

Marina Mauro

Carlo Felice Viscardi

Massimo Gagna

Original Assignee

Bracco Imaging Spa

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.)

1995-05-23

Filing date

1997-01-21

Publication date

2003-02-24

1995-05-23 Priority claimed from ITMI951045A external-priority patent/IT1274547B/it

1995-08-04 Priority claimed from IT95RM000549 external-priority patent/IT1277899B1/it

1997-01-21 Application filed by Bracco Imaging Spa filed Critical Bracco Imaging Spa

1997-01-21 Publication of NO970263D0 publication Critical patent/NO970263D0/no

1997-03-24 Publication of NO970263L publication Critical patent/NO970263L/no

2003-02-24 Publication of NO314257B1 publication Critical patent/NO314257B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title abstract description 10
159000000032 aromatic acids Chemical class 0.000 title 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 17
239000000243 solution Substances 0.000 claims abstract description 17
238000006192 iodination reaction Methods 0.000 claims abstract description 13
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 12
NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 claims abstract description 12
IUEVXLACZFKZSP-UHFFFAOYSA-L disodium;5-aminobenzene-1,3-dicarboxylate Chemical compound [Na+].[Na+].NC1=CC(C([O-])=O)=CC(C([O-])=O)=C1 IUEVXLACZFKZSP-UHFFFAOYSA-L 0.000 claims abstract description 11
230000026045 iodination Effects 0.000 claims abstract description 11
238000000746 purification Methods 0.000 claims abstract description 9
239000007864 aqueous solution Substances 0.000 claims abstract description 5
230000007935 neutral effect Effects 0.000 claims abstract description 5
235000011149 sulphuric acid Nutrition 0.000 claims abstract description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 4
239000012266 salt solution Substances 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 9
KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
-1 5-amino-2,4,6-triiodo-1,4-benzenedicarboxylic acid Chemical compound 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229940116559 iodinated x-ray contrast media Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction 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
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- 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
- C07C227/16—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 not involving the amino or carboxyl groups

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)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

NO19970263A 1995-05-23 1997-01-21 Fremgangsmåte ved fremstilling av en halogen-substituert aromatisk syre NO314257B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
ITMI951045A IT1274547B (it)	1995-05-23	1995-05-23	Processo per la preparazione dell'acido 5-ammino-2,4,6- triiodoisoftalico
IT95RM000549 IT1277899B1 (it)	1995-08-04	1995-08-04	Processo per la preparazione dell'acido 5-ammino-2,4,6 -triiodo- isoftalico"
PCT/EP1996/002105 WO1996037458A1 (en)	1995-05-23	1996-05-17	Process for the preparation of a halosubstituted aromatic acid

Publications (3)

Publication Number	Publication Date
NO970263D0 NO970263D0 (no)	1997-01-21
NO970263L NO970263L (no)	1997-03-24
NO314257B1 true NO314257B1 (no)	2003-02-24

Family

ID=26331278

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19970263A NO314257B1 (no)	1995-05-23	1997-01-21	Fremgangsmåte ved fremstilling av en halogen-substituert aromatisk syre

Country Status (23)

Country	Link
US (1)	US5763650A (de)
EP (1)	EP0773923B1 (de)
JP (1)	JP4012568B2 (de)
KR (1)	KR100269079B1 (de)
CN (1)	CN1109670C (de)
AT (1)	ATE192138T1 (de)
AU (1)	AU707177B2 (de)
BR (1)	BR9606487A (de)
CA (1)	CA2195635C (de)
CZ (1)	CZ289771B6 (de)
DE (2)	DE69607921T2 (de)
DK (1)	DK0773923T3 (de)
ES (1)	ES2103254T3 (de)
GR (2)	GR970300029T1 (de)
HU (1)	HU217686B (de)
IL (1)	IL118360A (de)
MX (1)	MX9700549A (de)
NO (1)	NO314257B1 (de)
PL (1)	PL318285A1 (de)
PT (1)	PT773923E (de)
SI (1)	SI9620011A (de)
SK (1)	SK8997A3 (de)
WO (1)	WO1996037458A1 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1966110B1 (de)	2005-12-19	2013-04-24	Ge Healthcare As	Verfahren zur aufreinigung von iodixanol
US8445725B2 (en)	2008-01-14	2013-05-21	Mallinckrodt Llc	Process for the preparation of iosimenol
EP2093206A1 (de) *	2008-02-20	2009-08-26	BRACCO IMAGING S.p.A.	Verfahren zur Iodierung aromatischer Verbindungen
EP2230227A1 (de)	2009-03-20	2010-09-22	Bracco Imaging S.p.A	Verfahren zur Herstellung von aromatischen Trijodid-Carboxyl- Derivaten
EP2243767A1 (de)	2009-04-21	2010-10-27	Bracco Imaging S.p.A	Verfahren zur Iodierung aromatischer Verbindungen
US9157156B2 (en) *	2009-07-07	2015-10-13	Bracco Imaging S.P.A.	Process for the preparation of a iodinating agent
US7999135B2 (en)	2009-07-21	2011-08-16	Ge Healthcare As	Crystallization of iodixanol using ultrasound
US7999134B2 (en)	2009-07-21	2011-08-16	Ge Healthcare As	Crystallization of iodixanol using milling
KR101699226B1 (ko)	2009-11-26	2017-01-24	호비온 차이나 홀딩 리미티드	이오딕사놀의 제조 및 정제
EP2394984A1 (de)	2010-06-10	2011-12-14	Bracco Imaging S.p.A	Verfahren zur Iodinierung von Phenol-Derivaten
KR102044772B1 (ko)	2012-12-11	2019-11-14	브라코 이미징 에스.피.에이.	(s)-2-아세틸옥시프로피온산 클로라이드의 제조를 위한 연속식 공정
CN105705483B (zh)	2013-11-05	2018-09-04	伯拉考成像股份公司	碘帕醇的制备方法
LT3154928T (lt)	2014-06-10	2020-05-11	Bracco Imaging S.P.A.	(s)-2-acetiloksipropioninės rūgšties ir jos darinių gavimo būdas
MX2019014608A (es) *	2017-06-07	2020-02-07	Bracco Imaging Spa	Proceso para la recuperacion de yodo de soluciones acuosas.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2820814A (en) *	1955-03-21	1958-01-21	Schering Corp	Polyiodinated 5-aminoisophthalic acids, salts, and esters
SU502875A1 (ru) *	1973-03-26	1976-02-15	Войсковая Часть 41598	Способ получени метилового эфира 4-диметиламиносалициловой кислоты
SU502874A1 (ru) *	1973-12-07	1976-02-15	Институт Органического Катализа И Электрохимии	Способ получени м-аминоизофталевой кислоты
US4102917A (en) *	1977-06-01	1978-07-25	American Cyanamid Company	Substituted phenyl naphthalenesulfonic acids
JP2765696B2 (ja) *	1989-12-27	1998-06-18	三井化学株式会社	５―アミノ―２，４，６―トリヨードイソフタル酸の製造方法

1996
- 1996-05-13 US US08/645,448 patent/US5763650A/en not_active Expired - Lifetime
- 1996-05-17 DE DE69607921T patent/DE69607921T2/de not_active Expired - Lifetime
- 1996-05-17 SK SK89-97A patent/SK8997A3/sk unknown
- 1996-05-17 CN CN96190526A patent/CN1109670C/zh not_active Expired - Lifetime
- 1996-05-17 DE DE0773923T patent/DE773923T1/de active Pending
- 1996-05-17 SI SI9620011A patent/SI9620011A/sl unknown
- 1996-05-17 AT AT96919779T patent/ATE192138T1/de active
- 1996-05-17 ES ES96919779T patent/ES2103254T3/es not_active Expired - Lifetime
- 1996-05-17 BR BR9606487A patent/BR9606487A/pt not_active Application Discontinuation
- 1996-05-17 PL PL96318285A patent/PL318285A1/xx unknown
- 1996-05-17 AU AU58189/96A patent/AU707177B2/en not_active Ceased
- 1996-05-17 WO PCT/EP1996/002105 patent/WO1996037458A1/en not_active Ceased
- 1996-05-17 PT PT96919779T patent/PT773923E/pt unknown
- 1996-05-17 KR KR1019970700404A patent/KR100269079B1/ko not_active Expired - Lifetime
- 1996-05-17 MX MX9700549A patent/MX9700549A/es unknown
- 1996-05-17 JP JP53534796A patent/JP4012568B2/ja not_active Expired - Lifetime
- 1996-05-17 HU HU9700189A patent/HU217686B/hu unknown
- 1996-05-17 DK DK96919779T patent/DK0773923T3/da active
- 1996-05-17 CZ CZ1997185A patent/CZ289771B6/cs not_active IP Right Cessation
- 1996-05-17 EP EP96919779A patent/EP0773923B1/de not_active Expired - Lifetime
- 1996-05-17 CA CA002195635A patent/CA2195635C/en not_active Expired - Lifetime
- 1996-05-22 IL IL11836096A patent/IL118360A/xx not_active IP Right Cessation
1997
- 1997-01-21 NO NO19970263A patent/NO314257B1/no not_active IP Right Cessation
- 1997-09-30 GR GR970300029T patent/GR970300029T1/el unknown
2000
- 2000-07-14 GR GR20000401642T patent/GR3033957T3/el unknown

Also Published As

Publication number	Publication date
CN1109670C (zh)	2003-05-28
ES2103254T1 (es)	1997-09-16
CA2195635C (en)	2008-07-22
HU217686B (hu)	2000-03-28
NO970263L (no)	1997-03-24
BR9606487A (pt)	1997-11-25
HUP9700189A1 (hu)	1998-01-28
EP0773923A1 (de)	1997-05-21
AU5818996A (en)	1996-12-11
AU707177B2 (en)	1999-07-01
DE773923T1 (de)	1997-12-18
KR100269079B1 (ko)	2000-10-16
ATE192138T1 (de)	2000-05-15
WO1996037458A1 (en)	1996-11-28
CA2195635A1 (en)	1996-11-28
CN1154688A (zh)	1997-07-16
DE69607921T2 (de)	2000-08-17
MX9700549A (es)	1997-05-31
US5763650A (en)	1998-06-09
JP4012568B2 (ja)	2007-11-21
PL318285A1 (en)	1997-06-09
NO970263D0 (no)	1997-01-21
CZ289771B6 (cs)	2002-04-17
GR3033957T3 (en)	2000-11-30
SK8997A3 (en)	1997-08-06
DK0773923T3 (da)	2000-09-04
DE69607921D1 (de)	2000-05-31
IL118360A (en)	1999-12-22
JPH10503530A (ja)	1998-03-31
HUP9700189A3 (en)	1998-03-02
SI9620011A (en)	1997-06-30
ES2103254T3 (es)	2000-07-01
GR970300029T1 (en)	1997-09-30
PT773923E (pt)	2000-08-31
CZ18597A3 (en)	1997-07-16
EP0773923B1 (de)	2000-04-26
IL118360A0 (en)	1996-09-12

Legal Events

Date	Code	Title	Description
2016-05-23	MK1K	Patent expired

Publication	Publication Date	Title
NO314257B1 (no)	2003-02-24	Fremgangsmåte ved fremstilling av en halogen-substituert aromatisk syre
HU218820B (hu)	2000-12-28	Eljárás kreatin és kreatin-monohidrát előállítására
US7285678B2 (en)	2007-10-23	Purification of 2-nitro-4-methylsulphonylbenzoic acid
AU2002249384A1 (en)	2003-03-27	Purification of 2-nitro-4-methylsulphonylbenzoic acid
CN100545146C (zh)	2009-09-30	2-氨基-5-碘安息香酸的制备方法
KR910008936B1 (ko)	1991-10-26	2,4-디클로로-5-플루오로-벤조산의 제조방법
JPH0774186B2 (ja)	1995-08-09	５−アミノサリチル酸の製造方法
US12103900B2 (en)	2024-10-01	Environment-friendly process for selective acylation of aminophenol
US4007221A (en)	1977-02-08	Manufacture of nuclear-iodinated iodine compounds of aromatic character
US5523472A (en)	1996-06-04	Process for the preparation of 5-fluoroanthranilic acid
JPS62288102A (ja)	1987-12-15	ジシアナミド金属塩の製造方法
US3427306A (en)	1969-02-11	Process for the manufacture of n-(5 - nitro - 2 - furfuryliden) - 1 - amino-hydantoin
US5233083A (en)	1993-08-03	Process for the preparation of 2-amino-3-chlorobenzoic acid
JPS6115848B2 (de)	1986-04-26
JPH0242043A (ja)	1990-02-13	４―ニトロ―３―トリフルオロメチルアニリンの製造方法
JP3547497B2 (ja)	2004-07-28	ベンゾチアゾロン化合物の製造方法
JPH0559027A (ja)	1993-03-09	２−メルカプト−ベンゾチアゾールの製法
JPH0525119A (ja)	1993-02-02	ｐ−トルエンスルホニル酢酸の製造方法
JP4114911B2 (ja)	2008-07-09	４−ヒドロキシベンゼンスルホンアニリドの製造方法
EP0596130B1 (de)	1997-09-24	Verfahren zur herstellung von 2-halo-3,5-difluoranilin sowie zwischenprodukt dafür und dessen herstellung
JPH02295968A (ja)	1990-12-06	４―ハロゲノチオフェノールの製造法
JPS6097943A (ja)	1985-05-31	５‐クロル‐２‐アミノフエノールの製造方法
GB2101130A (en)	1983-01-12	Process for preparing N-carbamoylbenzoic acid sulfimide derivatives
JPH06293711A (ja)	1994-10-21	モノｐ−ニトロベンジルマロネートの結晶変態及びその製法
JPS5841873A (ja)	1983-03-11	２−メルカプト−２−チアゾリン類の製法