NO313697B1 - Fremgangsmåte ved fremstilling av et dikarboksylsyre-diklorid - Google Patents

Fremgangsmåte ved fremstilling av et dikarboksylsyre-diklorid Download PDF

Info

Publication number: NO313697B1
Authority: NO; Norway
Prior art keywords: amino; triiodo; benzenedicarboxylic acid; solvent; acid
Prior art date: 1995-05-23

Application number

NO19970262A

Other languages

English (en)

Norwegian (no)

Other versions

NO970262D0 (no

NO970262L (no

Inventor

Marina Mauro

Carlo Felice Viscardi

Massimo Gatti

Nicola Desantis

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

2002-11-18

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

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

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

1997-01-21 Publication of NO970262D0 publication Critical patent/NO970262D0/no

1997-03-24 Publication of NO970262L publication Critical patent/NO970262L/no

2002-11-18 Publication of NO313697B1 publication Critical patent/NO313697B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 28
238000002360 preparation method Methods 0.000 title claims abstract description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title 1
239000002904 solvent Substances 0.000 claims abstract description 33
238000006243 chemical reaction Methods 0.000 claims abstract description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 8
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims abstract description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
239000000243 solution Substances 0.000 claims description 23
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 20
239000011541 reaction mixture Substances 0.000 claims description 19
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
238000010790 dilution Methods 0.000 claims description 10
239000012895 dilution Substances 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
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 description 8
239000000203 mixture Substances 0.000 claims description 8
238000000746 purification Methods 0.000 claims description 8
229910052757 nitrogen Inorganic materials 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
238000000605 extraction Methods 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
238000001556 precipitation Methods 0.000 claims description 5
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 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
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 4
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 3
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
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 2
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
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
229940090181 propyl acetate Drugs 0.000 claims description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
238000007865 diluting Methods 0.000 claims 4
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
239000012266 salt solution Substances 0.000 claims 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
238000005660 chlorination reaction Methods 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
230000026045 iodination Effects 0.000 claims 1
238000006192 iodination reaction Methods 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000007935 neutral effect Effects 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 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 abstract 1
239000000047 product Substances 0.000 description 35
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000003756 stirring Methods 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 5
239000012071 phase Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
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 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
238000002955 isolation Methods 0.000 description 4
230000003287 optical effect Effects 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000009413 insulation Methods 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000005406 washing Methods 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
GMPOMLNJZPYPGR-VKHMYHEASA-N [(2s)-1-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-1-oxopropan-2-yl] acetate Chemical compound CC(=O)O[C@@H](C)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I GMPOMLNJZPYPGR-VKHMYHEASA-N 0.000 description 2
XMMFBEWONDCTLD-UHFFFAOYSA-N acetyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)C(C)=O XMMFBEWONDCTLD-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002168 ethanoic acid esters Chemical class 0.000 description 2
229940094933 n-dodecane Drugs 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
-1 2-hydroxy -1-oxopropyl Chemical group 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 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
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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
239000007789 gas Substances 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
150000002500 ions Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000002572 peristaltic effect Effects 0.000 description 1
239000002279 physical standard Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000010349 pulsation Effects 0.000 description 1
150000003839 salts Chemical class 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
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000001540 sodium lactate Substances 0.000 description 1
235000011088 sodium lactate Nutrition 0.000 description 1
JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
238000000825 ultraviolet detection Methods 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)
Polyamides (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO19970262A 1995-05-23 1997-01-21 Fremgangsmåte ved fremstilling av et dikarboksylsyre-diklorid NO313697B1 (no)

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 (3)

Publication Number	Publication Date
NO970262D0 NO970262D0 (no)	1997-01-21
NO970262L NO970262L (no)	1997-03-24
NO313697B1 true NO313697B1 (no)	2002-11-18

Family

ID=26331280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19970262A NO313697B1 (no)	1995-05-23	1997-01-21	Fremgangsmåte ved fremstilling av et dikarboksylsyre-diklorid

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
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
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
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
LT2931696T (lt)	2012-12-11	2019-02-11	Bracco Imaging S.P.A.	Nepertraukiamas (s)-2-acetiloksipropiono rūgšties gamybos būdas
PT3066071T (pt)	2013-11-05	2018-06-25	Bracco Imaging Spa	Processo para a preparação de iopamidol
BR112016027507B1 (pt)	2014-06-10	2020-11-24	Bracco Imaging Spa	método para a preparação de ácido (s)-2-acetiloxipropiônico e seus derivados
JP7012722B2 (ja)	2016-12-05	2022-01-28	ブラッコ・イメージング・ソシエタ・ペル・アチオニ	放射線画像診断剤中間体の機械化学的合成
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 KR KR1019970700403A patent/KR100269080B1/ko not_active Expired - Lifetime
- 1996-05-17 CZ CZ1997186A patent/CZ290363B6/cs not_active IP Right Cessation
- 1996-05-17 BR BR9606394A patent/BR9606394A/pt not_active Application Discontinuation
- 1996-05-17 ES ES96919778T patent/ES2103253T3/es not_active Expired - Lifetime
- 1996-05-17 CA CA002195634A patent/CA2195634C/en not_active Expired - Lifetime
- 1996-05-17 DE DE0773925T patent/DE773925T1/de active Pending
- 1996-05-17 AU AU58188/96A patent/AU698623B2/en not_active Expired
- 1996-05-17 JP JP53534696A patent/JP4012567B2/ja not_active Expired - Lifetime
- 1996-05-17 PT PT96919778T patent/PT773925E/pt unknown
- 1996-05-17 CN CN96190525A patent/CN1068582C/zh not_active Expired - Lifetime
- 1996-05-17 AT AT96919778T patent/ATE189674T1/de not_active IP Right Cessation
- 1996-05-17 SK SK88-97A patent/SK8897A3/sk unknown
- 1996-05-17 SI SI9620010A patent/SI9620010B/sl unknown
- 1996-05-17 EP EP96919778A patent/EP0773925B1/de not_active Expired - Lifetime
- 1996-05-17 WO PCT/EP1996/002104 patent/WO1996037460A1/en not_active Ceased
- 1996-05-17 DE DE69606601T patent/DE69606601T2/de not_active Expired - Lifetime
- 1996-05-17 PL PL96318284A patent/PL187308B1/pl unknown
- 1996-05-17 HU HU9700190A patent/HU216537B/hu unknown
- 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
JP4012567B2 (ja)	2007-11-21
PL318284A1 (en)	1997-06-09
EP0773925A1 (de)	1997-05-21
SI9620010B (sl)	1998-08-31
DE69606601D1 (de)	2000-03-16
ES2103253T1 (es)	1997-09-16
PT773925E (pt)	2000-05-31
SI9620010A (en)	1997-06-30
GR970300028T1 (en)	1997-09-30
HUP9700190A1 (hu)	1998-01-28
JP4675355B2 (ja)	2011-04-20
ES2103253T3 (es)	2000-04-01
JPH10503529A (ja)	1998-03-31
CZ18697A3 (en)	1997-07-16
PL187308B1 (pl)	2004-06-30
WO1996037460A1 (en)	1996-11-28
CA2195634C (en)	2008-11-18
CN1154690A (zh)	1997-07-16
CA2195634A1 (en)	1996-11-28
US5672735A (en)	1997-09-30
BR9606394A (pt)	1997-10-28
NO970262D0 (no)	1997-01-21
ATE189674T1 (de)	2000-02-15
EP0773925B1 (de)	2000-02-09
AU5818896A (en)	1996-12-11
IL118358A (en)	2000-10-31
JP2007308503A (ja)	2007-11-29
CZ290363B6 (cs)	2002-07-17
SK8897A3 (en)	1997-08-06
CN1068582C (zh)	2001-07-18
DE773925T1 (de)	1997-12-18
AU698623B2 (en)	1998-11-05
IL118358A0 (en)	1996-09-12
KR100269080B1 (ko)	2000-10-16
HU216537B (hu)	1999-07-28
HUP9700190A3 (en)	1998-03-02
NO970262L (no)	1997-03-24
DE69606601T2 (de)	2000-07-06

Legal Events

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

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JP4675355B2 (ja)	2011-04-20	ジカルボン酸二塩化物の製造方法
US7655806B2 (en)	2010-02-02	Process for purification of anastrozole
NO323475B1 (no)	2007-05-21	Fremgangsmate ved fremstilling av 5-[acetyl(2,3-dihydroksypropyl)amino]-N,N'-bis(2,3-dihydroksypropyl)-2,4,6-triiod-1,3-benzendikarboksamid
CN106588741A (zh)	2017-04-26	一种布瓦西坦的制备方法
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