CN1195338A - 碘异肽醇制备中的一种中间体的纯化方法 - Google Patents
碘异肽醇制备中的一种中间体的纯化方法 Download PDFInfo
- Publication number
- CN1195338A CN1195338A CN97190690A CN97190690A CN1195338A CN 1195338 A CN1195338 A CN 1195338A CN 97190690 A CN97190690 A CN 97190690A CN 97190690 A CN97190690 A CN 97190690A CN 1195338 A CN1195338 A CN 1195338A
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- CN
- China
- Prior art keywords
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- method described
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims description 11
- 238000000746 purification Methods 0.000 title description 5
- 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 title description 3
- 229960004647 iopamidol Drugs 0.000 title description 3
- 229920005989 resin Polymers 0.000 claims abstract description 80
- 239000011347 resin Substances 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 21
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 18
- 150000002500 ions Chemical class 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000000129 anionic group Chemical group 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 238000004132 cross linking Methods 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 9
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 238000007667 floating Methods 0.000 claims description 6
- 230000003014 reinforcing effect Effects 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 239000002872 contrast media Substances 0.000 claims description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 238000010828 elution Methods 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000011097 chromatography purification Methods 0.000 abstract description 3
- -1 2-hydroxy-1-oxopropyl Chemical group 0.000 abstract description 2
- 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 abstract 1
- 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 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 230000003449 preventive effect Effects 0.000 abstract 1
- 229920001429 chelating resin Polymers 0.000 description 32
- 239000000243 solution Substances 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000011026 diafiltration Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VVCMQYAJSDFOLO-UHFFFAOYSA-N C(=C)C=CC1=CC=CC=C1.C(=C)C(=O)O Chemical compound C(=C)C=CC1=CC=CC=C1.C(=C)C(=O)O VVCMQYAJSDFOLO-UHFFFAOYSA-N 0.000 description 1
- QLDFBLTTYULMNF-UHFFFAOYSA-N C(C=1C(C(=O)OCCCCCCCC)=CC=CC1)(=O)OCCCCCCCC.IC=1C=CC=CC1 Chemical compound C(C=1C(C(=O)OCCCCCCCC)=CC=CC1)(=O)OCCCCCCCC.IC=1C=CC=CC1 QLDFBLTTYULMNF-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- UFNGEZFIBCOLBF-UHFFFAOYSA-N NC(=O)C1=CC=CC(C(N)=O)=C1I Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1I UFNGEZFIBCOLBF-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- 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)
- Removal Of Specific Substances (AREA)
- Carbon And Carbon Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims (20)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI96A001204 | 1996-06-13 | ||
IT96MI001204A IT1288114B1 (it) | 1996-06-13 | 1996-06-13 | Processo per la purificazione di un intermedio |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1195338A true CN1195338A (zh) | 1998-10-07 |
CN1089335C CN1089335C (zh) | 2002-08-21 |
Family
ID=11374420
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN97190690A Expired - Lifetime CN1089335C (zh) | 1996-06-13 | 1997-06-11 | 碘异肽醇制备中的一种中间体的纯化方法 |
Country Status (17)
Country | Link |
---|---|
US (1) | US5849953A (zh) |
EP (1) | EP0851854B1 (zh) |
JP (1) | JP4018751B2 (zh) |
CN (1) | CN1089335C (zh) |
AT (1) | ATE210630T1 (zh) |
AU (1) | AU3094597A (zh) |
CZ (1) | CZ293956B6 (zh) |
DE (1) | DE69709044T2 (zh) |
ES (1) | ES2165610T3 (zh) |
HU (1) | HU227980B1 (zh) |
IL (1) | IL123259A (zh) |
IN (1) | IN182809B (zh) |
IT (1) | IT1288114B1 (zh) |
NO (1) | NO324342B1 (zh) |
PT (1) | PT851854E (zh) |
WO (1) | WO1997047590A2 (zh) |
ZA (1) | ZA975203B (zh) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1299202B1 (it) * | 1998-05-08 | 2000-02-29 | Dibra Spa | Processo per la preparazione della s-n,n'-bis (2-idrossi-1- (idrossimetil)etil) -5-((2-idrossi-1-ossopropil)ammino)-2,4,6-triiodo |
IT1302200B1 (it) * | 1998-09-11 | 2000-07-31 | Dibra Spa | PROCESSO PER LA PREPARAZIONE DELLA S-N,N'-BIS°2-IDROSSI-1-(IDROSSIMETIL)ETILé-5-°(2-IDROSSI-1- |
DE102007053531B4 (de) * | 2007-11-09 | 2010-10-21 | Hs Genion Gmbh | Rolloeinrichtung |
EP2230227A1 (en) | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Process for the preparation of triiodinated carboxylic aromatic derivatives |
EP2243767A1 (en) | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Process for the iodination of aromatic compounds |
IT1403988B1 (it) * | 2010-07-15 | 2013-11-08 | Bracco Imaging Spa | Processo per la preparazione di agenti di contrasto. |
PL2931696T3 (pl) | 2012-12-11 | 2019-01-31 | Bracco Imaging S.P.A | Ciągły sposób otrzymywania kwasu (S)-2-acetyloksypropionowego |
CA2927706C (en) | 2013-11-05 | 2018-05-29 | Bracco Imaging Spa | Process for the preparation of iopamidol |
CA2949433C (en) | 2014-06-10 | 2022-05-03 | Bracco Imaging Spa | Method for the preparation of (s)-2-acetyloxypropionic acid and derivatives thereof |
PT108524B (pt) * | 2015-06-02 | 2017-12-15 | Hovione Farmaciência S A | Processo para a preparação de intermediários úteis na preparação de agentes de contraste não-iónicos |
WO2018104228A1 (en) | 2016-12-05 | 2018-06-14 | Bracco Imaging Spa | Mechanochemical synthesis of radiographic agents intermediates |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3324107A (en) * | 1964-03-27 | 1967-06-06 | Du Pont | Dialkylamide purification |
US3576870A (en) * | 1967-07-05 | 1971-04-27 | Du Pont | Process for purifying n,n-dimethylacetamide |
CH608189A5 (zh) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
CH616403A5 (en) * | 1975-10-29 | 1980-03-31 | Bracco Ind Chimica Spa | Process for the preparation of 2,4,6-triodoisophthalamides which are readily soluble in water. |
IT1193211B (it) * | 1979-08-09 | 1988-06-15 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono |
GB2088850B (en) * | 1980-12-09 | 1983-09-28 | Coal Industry Patents Ltd | Treatment of n-methyl pyrrolidone |
IT1256162B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
-
1996
- 1996-06-13 IT IT96MI001204A patent/IT1288114B1/it active IP Right Grant
-
1997
- 1997-06-11 EP EP97925993A patent/EP0851854B1/en not_active Expired - Lifetime
- 1997-06-11 PT PT97925993T patent/PT851854E/pt unknown
- 1997-06-11 ES ES97925993T patent/ES2165610T3/es not_active Expired - Lifetime
- 1997-06-11 HU HU9901631A patent/HU227980B1/hu unknown
- 1997-06-11 JP JP50119798A patent/JP4018751B2/ja not_active Expired - Lifetime
- 1997-06-11 AT AT97925993T patent/ATE210630T1/de not_active IP Right Cessation
- 1997-06-11 DE DE69709044T patent/DE69709044T2/de not_active Expired - Lifetime
- 1997-06-11 CZ CZ1998399A patent/CZ293956B6/cs not_active IP Right Cessation
- 1997-06-11 WO PCT/EP1997/003021 patent/WO1997047590A2/en active IP Right Grant
- 1997-06-11 AU AU30945/97A patent/AU3094597A/en not_active Abandoned
- 1997-06-11 IL IL12325997A patent/IL123259A/xx not_active IP Right Cessation
- 1997-06-11 CN CN97190690A patent/CN1089335C/zh not_active Expired - Lifetime
- 1997-06-12 ZA ZA9705203A patent/ZA975203B/xx unknown
- 1997-06-12 US US08/873,771 patent/US5849953A/en not_active Expired - Lifetime
- 1997-06-13 IN IN1291MA1997 patent/IN182809B/en unknown
-
1998
- 1998-02-11 NO NO19980594A patent/NO324342B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NO324342B1 (no) | 2007-09-24 |
EP0851854A2 (en) | 1998-07-08 |
JP4018751B2 (ja) | 2007-12-05 |
US5849953A (en) | 1998-12-15 |
HUP9901631A3 (en) | 2001-02-28 |
IT1288114B1 (it) | 1998-09-10 |
NO980594L (no) | 1998-04-07 |
WO1997047590A2 (en) | 1997-12-18 |
ITMI961204A0 (zh) | 1996-06-13 |
DE69709044D1 (de) | 2002-01-24 |
JPH11510827A (ja) | 1999-09-21 |
CZ39998A3 (cs) | 1998-07-15 |
ITMI961204A1 (it) | 1997-12-13 |
ATE210630T1 (de) | 2001-12-15 |
HU227980B1 (en) | 2012-07-30 |
PT851854E (pt) | 2002-06-28 |
ZA975203B (en) | 1998-01-20 |
HUP9901631A2 (hu) | 1999-08-30 |
DE69709044T2 (de) | 2002-08-22 |
IL123259A0 (en) | 1998-09-24 |
ES2165610T3 (es) | 2002-03-16 |
CZ293956B6 (cs) | 2004-08-18 |
CN1089335C (zh) | 2002-08-21 |
NO980594D0 (no) | 1998-02-11 |
AU3094597A (en) | 1998-01-07 |
IN182809B (zh) | 1999-07-24 |
EP0851854B1 (en) | 2001-12-12 |
IL123259A (en) | 2000-07-16 |
WO1997047590A3 (en) | 1998-04-02 |
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