SK8897A3 - Process for the preparation of s-(-)-5-££2-(acetoxy)-1- -oxopropyl|amino|-2,4,6-triiodine-1,3-benzenedicarboxylic acid dichloride - Google Patents

Process for the preparation of s-(-)-5-££2-(acetoxy)-1- -oxopropyl|amino|-2,4,6-triiodine-1,3-benzenedicarboxylic acid dichloride Download PDF

Info

Publication number: SK8897A3
Authority: SK; Slovakia
Prior art keywords: amino; triiodo; benzenedicarboxylic acid; acetyloxy; oxopropyl
Prior art date: 1995-05-23

Application number

SK88-97A

Other languages

English (en)

Slovak (sk)

Inventor

Marina Mauro

Fabrizio Minoja

Carlo F Viscardi

Massimo Gatti

Nicola Desantis

Original Assignee

Fructamine 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

1996-05-17

Publication date

1997-08-06

1995-05-23 Priority claimed from ITMI951048A external-priority patent/IT1274550B/it

1995-08-04 Priority claimed from ITRM950548 external-priority patent/IT1281319B1/it

1996-05-17 Application filed by Fructamine Spa filed Critical Fructamine Spa

1997-08-06 Publication of SK8897A3 publication Critical patent/SK8897A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 28
238000002360 preparation method Methods 0.000 title claims abstract description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 title description 2
239000002904 solvent Substances 0.000 claims abstract description 30
238000006243 chemical reaction Methods 0.000 claims abstract description 17
239000002253 acid Substances 0.000 claims abstract description 8
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 claims abstract description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
239000000243 solution Substances 0.000 claims description 29
239000011541 reaction mixture Substances 0.000 claims description 21
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 14
238000000746 purification Methods 0.000 claims description 13
238000002955 isolation Methods 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
238000001556 precipitation Methods 0.000 claims description 5
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 claims description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
XMMFBEWONDCTLD-UHFFFAOYSA-N acetyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)C(C)=O XMMFBEWONDCTLD-UHFFFAOYSA-N 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
238000000605 extraction Methods 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 3
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
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
238000007865 diluting Methods 0.000 claims description 3
239000007789 gas Substances 0.000 claims description 3
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 description 2
230000003197 catalytic effect Effects 0.000 claims description 2
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 description 2
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
238000005192 partition Methods 0.000 claims description 2
229940090181 propyl acetate Drugs 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 2
WJXXCTSBMNYHHS-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarbonyl chloride Chemical compound NC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 WJXXCTSBMNYHHS-UHFFFAOYSA-N 0.000 claims 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
150000002168 ethanoic acid esters Chemical class 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
239000012433 hydrogen halide Substances 0.000 claims 1
229910000039 hydrogen halide Inorganic materials 0.000 claims 1
230000002083 iodinating effect Effects 0.000 claims 1
230000007935 neutral effect Effects 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract 1
239000000047 product Substances 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000003756 stirring Methods 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
239000012071 phase Substances 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
238000009413 insulation Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000002002 slurry Substances 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
229940126062 Compound A Drugs 0.000 description 2
230000005526 G1 to G0 transition Effects 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000000825 ultraviolet detection Methods 0.000 description 2
NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
229910006124 SOCl2 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
RGXHKACZQXJQIC-UHFFFAOYSA-N [1-[3-carbamoyl-5-(1,3-dihydroxypropan-2-ylcarbamoyl)-2,4,6-triiodoanilino]-1-oxopropan-2-yl] acetate Chemical compound CC(=O)OC(C)C(=O)NC1=C(I)C(C(N)=O)=C(I)C(C(=O)NC(CO)CO)=C1I RGXHKACZQXJQIC-UHFFFAOYSA-N 0.000 description 1
GFTWDQJSZPFMOZ-UHFFFAOYSA-N acetyl acetate Chemical compound CC(=O)OC(C)=O.CC(=O)OC(C)=O GFTWDQJSZPFMOZ-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
239000002872 contrast media Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
BONORRGKLJBGRV-UHFFFAOYSA-N methapyrilene hydrochloride Chemical group Cl.C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CS1 BONORRGKLJBGRV-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229940094933 n-dodecane Drugs 0.000 description 1
230000002572 peristaltic effect Effects 0.000 description 1
239000002279 physical standard Substances 0.000 description 1
YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
230000010349 pulsation Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polyamides (AREA)

SK88-97A 1995-05-23 1996-05-17 Process for the preparation of s-(-)-5-££2-(acetoxy)-1- -oxopropyl|amino|-2,4,6-triiodine-1,3-benzenedicarboxylic acid dichloride SK8897A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
ITMI951048A IT1274550B (it)	1995-05-23	1995-05-23	Processo per la preparazione del dicloruro dell'acido s-5-¬¬2- (acetilossi)-1-ossopropil\|ammino\|-2,4,6-triiodo-1,3- benzendicarbossilico
ITRM950548 IT1281319B1 (it)	1995-08-04	1995-08-04	Procedimento per la preparazione di dicloruro dell'acido s-5-<<2- (acetilossi)-1-ossopropil>ammino>-2,4,6-triiodo-1,3-benzendi-
PCT/EP1996/002104 WO1996037460A1 (en)	1995-05-23	1996-05-17	Process for the preparation of a dicarboxylic acid dichloride

Publications (1)

Publication Number	Publication Date
SK8897A3 true SK8897A3 (en)	1997-08-06

Family

ID=26331280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK88-97A SK8897A3 (en)	1995-05-23	1996-05-17	Process for the preparation of s-(-)-5-££2-(acetoxy)-1- -oxopropyl\|amino\|-2,4,6-triiodine-1,3-benzenedicarboxylic acid dichloride

Country Status (21)

Country	Link
US (1)	US5672735A (de)
EP (1)	EP0773925B1 (de)
JP (2)	JP4012567B2 (de)
KR (1)	KR100269080B1 (de)
CN (1)	CN1068582C (de)
AT (1)	ATE189674T1 (de)
AU (1)	AU698623B2 (de)
BR (1)	BR9606394A (de)
CA (1)	CA2195634C (de)
CZ (1)	CZ290363B6 (de)
DE (2)	DE773925T1 (de)
ES (1)	ES2103253T3 (de)
GR (1)	GR970300028T1 (de)
HU (1)	HU216537B (de)
IL (1)	IL118358A (de)
NO (1)	NO313697B1 (de)
PL (1)	PL187308B1 (de)
PT (1)	PT773925E (de)
SI (1)	SI9620010B (de)
SK (1)	SK8897A3 (de)
WO (1)	WO1996037460A1 (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1289519B1 (it) *	1996-12-24	1998-10-15	Zambon Spa	Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati
IT1289521B1 (it) *	1996-12-24	1998-10-15	Zambon Spa	Processo per la purificazione di un intermedio
IT1289520B1 (it) *	1996-12-24	1998-10-15	Zambon Spa	Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati
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
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
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
CN110023279B (zh)	2016-12-05	2022-03-11	伯拉考成像股份公司	放射照相剂中间体的机械化学合成
FR3062850B1 (fr)	2017-02-10	2020-01-31	Guerbet	Procede de preparation monotope de composes organo-iodes
FR3084668A1 (fr)	2018-08-02	2020-02-07	Guerbet	Procede de preparation monotope de composes organo-iodes intermediaires a la synthese du ioversol

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH608189A5 (de)	1974-12-13	1978-12-29	Savac Ag
CH626873A5 (de) *	1977-03-28	1981-12-15	Bracco Ind Chimica Spa
DE2909439A1 (de) *	1979-03-08	1980-09-18	Schering Ag	Neue nichtionische roentgenkontrastmittel
IT1256162B (it) *	1992-10-27	1995-11-29	Zambon Spa	Processo per la preparazione di un intermedio della sintesi organica
IT1274027B (it) *	1994-03-03	1997-07-14	Zambon Spa	Processo per la preparazione e purificazione di mezzi di contrasto iodurati

1996
- 1996-05-17 PT PT96919778T patent/PT773925E/pt unknown
- 1996-05-17 AU AU58188/96A patent/AU698623B2/en not_active Expired
- 1996-05-17 HU HU9700190A patent/HU216537B/hu unknown
- 1996-05-17 CZ CZ1997186A patent/CZ290363B6/cs not_active IP Right Cessation
- 1996-05-17 AT AT96919778T patent/ATE189674T1/de not_active IP Right Cessation
- 1996-05-17 BR BR9606394A patent/BR9606394A/pt not_active Application Discontinuation
- 1996-05-17 DE DE0773925T patent/DE773925T1/de active Pending
- 1996-05-17 SI SI9620010A patent/SI9620010B/sl unknown
- 1996-05-17 KR KR1019970700403A patent/KR100269080B1/ko not_active Expired - Lifetime
- 1996-05-17 SK SK88-97A patent/SK8897A3/sk unknown
- 1996-05-17 ES ES96919778T patent/ES2103253T3/es not_active Expired - Lifetime
- 1996-05-17 DE DE69606601T patent/DE69606601T2/de not_active Expired - Lifetime
- 1996-05-17 CN CN96190525A patent/CN1068582C/zh not_active Expired - Lifetime
- 1996-05-17 WO PCT/EP1996/002104 patent/WO1996037460A1/en not_active Ceased
- 1996-05-17 PL PL96318284A patent/PL187308B1/pl unknown
- 1996-05-17 EP EP96919778A patent/EP0773925B1/de not_active Expired - Lifetime
- 1996-05-17 JP JP53534696A patent/JP4012567B2/ja not_active Expired - Lifetime
- 1996-05-17 CA CA002195634A patent/CA2195634C/en not_active Expired - Lifetime
- 1996-05-21 US US08/651,474 patent/US5672735A/en not_active Expired - Lifetime
- 1996-05-22 IL IL11835896A patent/IL118358A/xx not_active IP Right Cessation
1997
- 1997-01-21 NO NO19970262A patent/NO313697B1/no not_active IP Right Cessation
- 1997-09-30 GR GR970300028T patent/GR970300028T1/el unknown
2007
- 2007-06-19 JP JP2007160804A patent/JP4675355B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU5818896A (en)	1996-12-11
NO970262D0 (no)	1997-01-21
BR9606394A (pt)	1997-10-28
DE773925T1 (de)	1997-12-18
PL318284A1 (en)	1997-06-09
JP4675355B2 (ja)	2011-04-20
ES2103253T3 (es)	2000-04-01
DE69606601D1 (de)	2000-03-16
SI9620010A (en)	1997-06-30
JPH10503529A (ja)	1998-03-31
CN1154690A (zh)	1997-07-16
NO313697B1 (no)	2002-11-18
AU698623B2 (en)	1998-11-05
ES2103253T1 (es)	1997-09-16
EP0773925B1 (de)	2000-02-09
CZ290363B6 (cs)	2002-07-17
CN1068582C (zh)	2001-07-18
NO970262L (no)	1997-03-24
PL187308B1 (pl)	2004-06-30
CA2195634A1 (en)	1996-11-28
HUP9700190A3 (en)	1998-03-02
PT773925E (pt)	2000-05-31
JP2007308503A (ja)	2007-11-29
SI9620010B (sl)	1998-08-31
JP4012567B2 (ja)	2007-11-21
IL118358A (en)	2000-10-31
KR100269080B1 (ko)	2000-10-16
DE69606601T2 (de)	2000-07-06
IL118358A0 (en)	1996-09-12
HUP9700190A1 (hu)	1998-01-28
US5672735A (en)	1997-09-30
GR970300028T1 (en)	1997-09-30
EP0773925A1 (de)	1997-05-21
HU216537B (hu)	1999-07-28
WO1996037460A1 (en)	1996-11-28
CZ18697A3 (en)	1997-07-16
CA2195634C (en)	2008-11-18
ATE189674T1 (de)	2000-02-15

Publication	Publication Date	Title
JP4675355B2 (ja)	2011-04-20	ジカルボン酸二塩化物の製造方法
JP3437584B2 (ja)	2003-08-18	５―［アセチル（２，３―ジヒドロキシプロピル）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―１，３―ベンゼンジカルボキシアミドの製造方法
EP1150943B1 (de)	2003-09-10	Herstellung von iodixanol
RU2614412C2 (ru)	2017-03-28	Непрерывный способ алкилирования циклических третичных аминов
KR101083147B1 (ko)	2011-11-11	요오헥솔의 제조 방법
JP2011509943A (ja)	2011-03-31	イオシメノールを調製するためのプロセス
JP2000517312A (ja)	2000-12-26	イオヘキソールの製法
EP0513063B1 (de)	1995-05-17	Verfahren zur herstellung von ioversol
EP4288413B1 (de)	2025-01-22	Verfahren zur herstellung eines stickoxidabgebenden prostaglandinanalogs
JP2001515496A (ja)	2001-09-18	５−アミノメチル−クロロピリジン類の製造方法
ES2729404T3 (es)	2019-11-04	Proceso de hidrocloruro de fingolimod
US20030139606A1 (en)	2003-07-24	Process for preparing 5-methylisoxazole-4-carboxylic- (4'-trifluoromethyl)-anilide
JP2001510178A (ja)	2001-07-31	３−ヒドロキシ−２−メチル安息香酸の製造方法
HK40102118A (zh)	2024-05-31	供给一氧化氮的前列腺素类似物的制备方法
ITRM950548A1 (it)	1997-02-04	Procedimento per la preparazione di ammidi
ITMI951048A1 (it)	1996-11-23	Processo per la preparazione del dicloruro dell'acido s-5-2- ( acetilossi ) - 1 - ossopropil ammino -2,4,6-triiodo-1,3-