NO327489B1 - Fremstilling av trijodbensen forbindelser - Google Patents

Fremstilling av trijodbensen forbindelser Download PDF

Info

Publication number: NO327489B1
Authority: NO; Norway
Prior art keywords: added; temperature; agent; range; amino
Prior art date: 1997-05-23

Application number

NO19995675A

Other languages

English (en)

Norwegian (no)

Other versions

NO995675D0 (no

NO995675L (no

Inventor

Dick Malthe-Sorenssen

Ole Magne Homestad

Britt Sterud

Original Assignee

Ge Healthcare As

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.)

1997-05-23

Filing date

1999-11-19

Publication date

2009-07-13

1999-11-19 Application filed by Ge Healthcare As filed Critical Ge Healthcare As

1999-11-19 Publication of NO995675D0 publication Critical patent/NO995675D0/no

1999-11-19 Publication of NO995675L publication Critical patent/NO995675L/no

2009-07-13 Publication of NO327489B1 publication Critical patent/NO327489B1/no

Links

238000002360 preparation method Methods 0.000 title abstract description 5
RIWAPWDHHMWTRA-UHFFFAOYSA-N 1,2,3-triiodobenzene Chemical class IC1=CC=CC(I)=C1I RIWAPWDHHMWTRA-UHFFFAOYSA-N 0.000 title description 2
239000003795 chemical substances by application Substances 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 25
-1 iodine halide Chemical class 0.000 claims abstract description 22
229910052740 iodine Inorganic materials 0.000 claims abstract description 14
239000011630 iodine Substances 0.000 claims abstract description 14
XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical class NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims abstract description 12
239000012736 aqueous medium Substances 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 9
239000012431 aqueous reaction media Substances 0.000 claims abstract description 4
150000001412 amines Chemical class 0.000 claims abstract 4
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical group ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 28
238000006192 iodination reaction Methods 0.000 claims description 25
230000026045 iodination Effects 0.000 claims description 22
239000012429 reaction media Substances 0.000 claims description 11
XOZGAPXHJKSZCU-UHFFFAOYSA-N 5-amino-1-n,3-n-bis(2,3-dihydroxypropyl)benzene-1,3-dicarboxamide Chemical compound NC1=CC(C(=O)NCC(O)CO)=CC(C(=O)NCC(O)CO)=C1 XOZGAPXHJKSZCU-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
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 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
239000012336 iodinating agent Substances 0.000 abstract 2
238000006243 chemical reaction Methods 0.000 description 14
238000007792 addition Methods 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000003518 caustics Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 10
239000012535 impurity Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000002872 contrast media Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000004811 liquid chromatography Methods 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
GSCPDZHWVNUUFI-UHFFFAOYSA-N 3-aminobenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1 GSCPDZHWVNUUFI-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
BCBIXNWEWWQJST-UHFFFAOYSA-N ClICl Chemical class ClICl BCBIXNWEWWQJST-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229940088679 drug related substance Drugs 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229960001025 iohexol Drugs 0.000 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 description 2
150000003839 salts Chemical class 0.000 description 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
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 1
UXPIWHPHEGRYLB-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxamide Chemical compound NC(=O)C1=CC(N)=CC(C(N)=O)=C1 UXPIWHPHEGRYLB-UHFFFAOYSA-N 0.000 description 1
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 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-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
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
LHAXAXZUTHLWDX-UHFFFAOYSA-N [Na].ICl Chemical compound [Na].ICl LHAXAXZUTHLWDX-UHFFFAOYSA-N 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
125000003368 amide group Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000002591 computed tomography Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000013527 degreasing agent Substances 0.000 description 1
239000000539 dimer Substances 0.000 description 1
239000007862 dimeric product 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
238000009472 formulation Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000002768 hydroxyalkyl group Chemical class 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229960004359 iodixanol Drugs 0.000 description 1
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 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
229960000824 iopentol Drugs 0.000 description 1
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 description 1
229960004537 ioversol Drugs 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
238000007040 multi-step synthesis reaction Methods 0.000 description 1
FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000012306 spectroscopic technique Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000006257 total synthesis reaction 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide 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)
Other In-Based Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Glass Compositions (AREA)
Iron Core Of Rotating Electric Machines (AREA)

NO19995675A 1997-05-23 1999-11-19 Fremstilling av trijodbensen forbindelser NO327489B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9710725.4A GB9710725D0 (en)	1997-05-23	1997-05-23	Process
PCT/GB1998/001488 WO1998052908A1 (en)	1997-05-23	1998-05-22	Preparation of tri-iodo benzene compounds

Publications (3)

Publication Number	Publication Date
NO995675D0 NO995675D0 (no)	1999-11-19
NO995675L NO995675L (no)	1999-11-19
NO327489B1 true NO327489B1 (no)	2009-07-13

Family

ID=10812987

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19995675A NO327489B1 (no)	1997-05-23	1999-11-19	Fremstilling av trijodbensen forbindelser

Country Status (17)

Country	Link
US (1)	US6274762B1 (de)
EP (1)	EP0984922B1 (de)
JP (1)	JP4039700B2 (de)
KR (1)	KR100544932B1 (de)
CN (1)	CN1152854C (de)
AT (1)	ATE221872T1 (de)
AU (1)	AU7540498A (de)
BR (1)	BR9809658A (de)
CA (1)	CA2290529A1 (de)
CZ (1)	CZ296389B6 (de)
DE (1)	DE69807073T2 (de)
ES (1)	ES2183366T3 (de)
GB (1)	GB9710725D0 (de)
IL (1)	IL133099A0 (de)
NO (1)	NO327489B1 (de)
PT (1)	PT984922E (de)
WO (1)	WO1998052908A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN100355710C (zh) *	2005-12-15	2007-12-19	上海交通大学	芳烃碘代物的制备方法
EP2243767A1 (de) *	2009-04-21	2010-10-27	Bracco Imaging S.p.A	Verfahren zur Iodierung aromatischer Verbindungen
US20110021834A1 (en) *	2009-07-21	2011-01-27	Ge Healthcare As	Continuous process of preparing intermediate for non-ionic x-ray contrast agents
US20110020238A1 (en) *	2009-07-21	2011-01-27	Ge Healthcare As	Stabilizing aqueous solution of iodine chloride by adding sodium chloride
US7863484B1 (en)	2009-07-21	2011-01-04	Ge Healthcare As	Method for reducing aminoisophthalic acid bisamide related impurities in preparation of non-ionic X-ray contrast agents
EP2277846A1 (de)	2009-07-21	2011-01-26	GE Healthcare AS	Erhalt freien Iods bei der Herstellung von wässrigem Iodchlorid durch Zugabe von Iodid
US20110021833A1 (en) *	2009-07-21	2011-01-27	Ge Healthcare As	Crystallization of an intermediate for synthesizing non-ionic x-ray contrast agents
JP5754842B2 (ja) *	2011-03-02	2015-07-29	株式会社東邦アーステック	ｐ−ヨードフェノールの製造方法
US9382194B2 (en)	2011-10-31	2016-07-05	Imax Diagnostic Imaging Holding Limited	Iodination process for the preparation of 3, 5-disubstituted-2, 4, 6-triiodo aromatic amines compounds
CN103086915A (zh) *	2011-10-31	2013-05-08	上海海神化学生物科技有限公司	制备3,5-二取代-2,4,6-三碘代芳香胺类化合物的碘化方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3145197A (en) *	1961-06-26	1964-08-18	Mallinckrodt Chemical Works	5-acetamido-nu-alkyl-2, 4, 6-trhodoiso-phthalamic acid compounds
SE348727B (de) *	1969-07-08	1972-09-11	Pharmacia Ab
GB1466852A (en) *	1973-05-18	1977-03-09	Nyegaard & Co As	Iodination process
GB1548594A (en) *	1976-06-11	1979-07-18	Nyegaard & Co As	Triiodoisophthalic acid amides
US4125599A (en) *	1976-08-19	1978-11-14	Mallinckrodt, Inc.	X-ray contrast agents
FR2614299B1 (fr) *	1987-04-23	1989-08-18	Guerbet Sa	Composes diamino benzeniques iodes, leur procede de preparation et produits de contraste les contenant.
EP0408654B1 (de) *	1988-04-06	1995-05-24	Mallinckrodt, Inc.	Verfahren zur herstellung von 2,4,6-triiodo-5-amino-n-alkyl-isophthalsäure
US5013865A (en) *	1988-04-06	1991-05-07	Mallinckrodt, Inc.	Process for the preparation of 2,4,6-triiodo-5-amino-N-alkylisophthalamic acid and 2,4,6-triiodo-5-amino-isophthalamide compounds

1997
- 1997-05-23 GB GBGB9710725.4A patent/GB9710725D0/en active Pending
1998
- 1998-05-22 WO PCT/GB1998/001488 patent/WO1998052908A1/en not_active Ceased
- 1998-05-22 BR BR9809658-3A patent/BR9809658A/pt not_active IP Right Cessation
- 1998-05-22 EP EP98922944A patent/EP0984922B1/de not_active Expired - Lifetime
- 1998-05-22 CZ CZ0417299A patent/CZ296389B6/cs not_active IP Right Cessation
- 1998-05-22 IL IL13309998A patent/IL133099A0/xx unknown
- 1998-05-22 CN CNB988053209A patent/CN1152854C/zh not_active Expired - Lifetime
- 1998-05-22 AT AT98922944T patent/ATE221872T1/de not_active IP Right Cessation
- 1998-05-22 ES ES98922944T patent/ES2183366T3/es not_active Expired - Lifetime
- 1998-05-22 KR KR1019997010788A patent/KR100544932B1/ko not_active Expired - Lifetime
- 1998-05-22 CA CA002290529A patent/CA2290529A1/en not_active Abandoned
- 1998-05-22 JP JP55013798A patent/JP4039700B2/ja not_active Expired - Lifetime
- 1998-05-22 DE DE69807073T patent/DE69807073T2/de not_active Expired - Lifetime
- 1998-05-22 PT PT98922944T patent/PT984922E/pt unknown
- 1998-05-22 AU AU75404/98A patent/AU7540498A/en not_active Abandoned
1999
- 1999-11-12 US US09/432,632 patent/US6274762B1/en not_active Expired - Lifetime
- 1999-11-19 NO NO19995675A patent/NO327489B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
BR9809658A (pt)	2000-07-11
EP0984922A1 (de)	2000-03-15
ATE221872T1 (de)	2002-08-15
IL133099A0 (en)	2001-03-19
GB9710725D0 (en)	1997-07-16
US6274762B1 (en)	2001-08-14
EP0984922B1 (de)	2002-08-07
DE69807073D1 (de)	2002-09-12
CN1152854C (zh)	2004-06-09
CZ417299A3 (cs)	2000-05-17
WO1998052908A1 (en)	1998-11-26
KR100544932B1 (ko)	2006-01-24
AU7540498A (en)	1998-12-11
DE69807073T2 (de)	2003-10-09
ES2183366T3 (es)	2003-03-16
CA2290529A1 (en)	1998-11-26
PT984922E (pt)	2002-12-31
KR20010012824A (ko)	2001-02-26
JP2001526677A (ja)	2001-12-18
CZ296389B6 (cs)	2006-03-15
JP4039700B2 (ja)	2008-01-30
NO995675D0 (no)	1999-11-19
CN1257476A (zh)	2000-06-21
NO995675L (no)	1999-11-19

Legal Events

Date	Code	Title	Description
2018-06-11	MK1K	Patent expired

Publication	Publication Date	Title
NO327489B1 (no)	2009-07-13	Fremstilling av trijodbensen forbindelser
AU2013341615B2 (en)	2017-12-14	Preparation of intermediates of X-ray contrast agents
US5817861A (en)	1998-10-06	Process for the preparation of an intermediate useful in the synthesis of iodinated contrast media
US6137006A (en)	2000-10-24	Preparation of tri-iodo benzene compounds
CN102325748A (zh)	2012-01-18	制备三碘化羧酸芳香族衍生物的方法
CZ296230B6 (cs)	2006-02-15	Zpusob výroby N-alkylacylaminofenylkarboxylové kyseliny nebo derivátu karboxylové kyseliny
EP0794937A1 (de)	1997-09-17	Verfahren zur herstellung von 5-amino-2,4,6-triiodoisophthalsaüredischloride durch chlorierung des entprechenden saüre in gegenvert eines tertiären aminsalzes oder eines quaternären ammoniumsalzes
US5177261A (en)	1993-01-05	Synthesis of ioversol using chloroacetyl chloride
US5371278A (en)	1994-12-06	Synthesis of ioversol using a minimal excess of acetoxyacetylchloride
EP0983227B8 (de)	2006-10-25	Herstellung von tri-iodo-benzol-verbindungen
JPH11505234A (ja)	1999-05-18	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
EP2289870A1 (de)	2011-03-02	Verfahren zur Reinigung von 5-amino-N,N'-bis(2,3-dihydroxypropyl)-isophthalamid, ein Zwischenprodukt in der Herstellung von nichtionischen Röntgenkontrastmitteln
WO1993016981A1 (en)	1993-09-02	Synthesis of ioversol using a minimal excess of acetoxyacetylchloride
EP2277846A1 (de)	2011-01-26	Erhalt freien Iods bei der Herstellung von wässrigem Iodchlorid durch Zugabe von Iodid
KR20200032280A (ko)	2020-03-26	조영제 이오메프롤의 제조방법
KR20000075115A (ko)	2000-12-15	불순물 ｃ가 제거된 이오파미돌의 신규 제조방법