IL127502A - Process for preparing 3-isochromanone - Google Patents
Process for preparing 3-isochromanoneInfo
- Publication number
- IL127502A IL127502A IL12750297A IL12750297A IL127502A IL 127502 A IL127502 A IL 127502A IL 12750297 A IL12750297 A IL 12750297A IL 12750297 A IL12750297 A IL 12750297A IL 127502 A IL127502 A IL 127502A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- fluorobenzene
- isochromanone
- strength
- process according
- Prior art date
Links
- ILHLUZUMRJQEAH-UHFFFAOYSA-N 1,4-dihydroisochromen-3-one Chemical compound C1=CC=C2COC(=O)CC2=C1 ILHLUZUMRJQEAH-UHFFFAOYSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title description 5
- RFYCQJHCAPCSTA-UHFFFAOYSA-N 2-[2-(chloromethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CCl RFYCQJHCAPCSTA-UHFFFAOYSA-N 0.000 claims abstract description 12
- RZWGTXHSYZGXKF-UHFFFAOYSA-N 2-(2-methylphenyl)acetic acid Chemical compound CC1=CC=CC=C1CC(O)=O RZWGTXHSYZGXKF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 7
- 150000003254 radicals Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- -1 alkali metal bicarbonate Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 abstract description 17
- 235000015497 potassium bicarbonate Nutrition 0.000 abstract description 16
- 229910000028 potassium bicarbonate Inorganic materials 0.000 abstract description 16
- 239000011736 potassium bicarbonate Substances 0.000 abstract description 16
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract description 10
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract description 4
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 abstract description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
- 238000007792 addition Methods 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000010533 azeotropic distillation Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- 101150041968 CDC13 gene Proteins 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- UKPMFGARCZOXDI-UHFFFAOYSA-N 2-(2-methoxy-2-oxoethyl)benzoic acid Chemical compound COC(=O)CC1=CC=CC=C1C(O)=O UKPMFGARCZOXDI-UHFFFAOYSA-N 0.000 description 1
- OWUUOJBKIIEHTJ-UHFFFAOYSA-N 2-[2-(bromomethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CBr OWUUOJBKIIEHTJ-UHFFFAOYSA-N 0.000 description 1
- JWOILLKILSILKB-UHFFFAOYSA-N 3,4-dihydro-1h-isochromen-3-ol Chemical compound C1=CC=C2COC(O)CC2=C1 JWOILLKILSILKB-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
- 238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 description 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 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9612623.0A GB9612623D0 (en) | 1996-06-17 | 1996-06-17 | Chemical process |
| PCT/GB1997/001391 WO1997048692A1 (en) | 1996-06-17 | 1997-05-21 | Process for preparing 3-isochromanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL127502A0 IL127502A0 (en) | 1999-10-28 |
| IL127502A true IL127502A (en) | 2002-03-10 |
Family
ID=10795412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12750297A IL127502A (en) | 1996-06-17 | 1997-05-21 | Process for preparing 3-isochromanone |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6008381A (enExample) |
| EP (1) | EP0906304B1 (enExample) |
| JP (1) | JP3830975B2 (enExample) |
| CN (1) | CN1102590C (enExample) |
| AT (1) | ATE203241T1 (enExample) |
| AU (1) | AU2908697A (enExample) |
| BR (1) | BR9709735A (enExample) |
| DE (1) | DE69705721T2 (enExample) |
| DK (1) | DK0906304T3 (enExample) |
| ES (1) | ES2158561T3 (enExample) |
| GB (1) | GB9612623D0 (enExample) |
| GR (1) | GR3036239T3 (enExample) |
| IL (1) | IL127502A (enExample) |
| IN (1) | IN186158B (enExample) |
| PT (1) | PT906304E (enExample) |
| TW (1) | TW505641B (enExample) |
| WO (1) | WO1997048692A1 (enExample) |
| ZA (1) | ZA974629B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL133288A (en) * | 1997-08-26 | 2003-05-29 | Zeneca Ltd | Process for preparing 3-isochromanone |
| JP3874925B2 (ja) * | 1998-04-22 | 2007-01-31 | イハラケミカル工業株式会社 | クロロメチルフェニル酢酸の製造方法 |
| DE19923548A1 (de) | 1999-05-21 | 2000-11-23 | Clariant Gmbh | Verfahren zur Herstellung von 3-Isochromanonen durch Cyclisierung von o-Chlormethylphenylessigsäuren |
| US6428654B1 (en) | 2000-04-05 | 2002-08-06 | Hercules Incorporated | Fungicidal method |
| GB0125473D0 (en) * | 2001-10-24 | 2001-12-12 | Syngenta Ltd | Chemical process |
| GB0210370D0 (en) * | 2002-05-07 | 2002-06-12 | Syngenta Ltd | Chemical process |
| CN102297924B (zh) * | 2011-06-21 | 2013-10-30 | 上海试四赫维化工有限公司 | 3-异苯并二氢吡喃酮中邻-甲基苯乙酸和2-氯甲基苯乙酸杂质含量的高效液相色谱分析方法 |
| CN109456295B (zh) * | 2018-12-11 | 2022-03-01 | 苏州华道生物药业股份有限公司 | 3-异苯并二氢吡喃酮的微通道法合成工艺 |
| CN109553601B (zh) * | 2019-01-31 | 2020-11-10 | 河南科技大学 | 一种无催化剂法制备5-溴异色满-4-酮的工艺方法 |
| CN112125876A (zh) * | 2020-08-25 | 2020-12-25 | 宁夏思科达生物科技有限公司 | 一种3-异色酮的合成方法 |
| CN115417849B (zh) * | 2022-10-10 | 2023-09-26 | 河南省化工研究所有限责任公司 | 一种催化合成3-异色酮的方法 |
| CN115772147B (zh) * | 2022-12-23 | 2024-03-22 | 长沙钰腾新材料有限公司 | 3-异色酮或其衍生物的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA804045A (en) * | 1969-01-14 | Tenneco Chemicals | Herbicidal compositions and methods | |
| CA802822A (en) * | 1968-12-31 | S. Newcomer Jack | 2,3,6-trichlorophenylacetic acid | |
| US3489784A (en) * | 1967-03-30 | 1970-01-13 | Hoffmann La Roche | (chlorinated alpha,alpha,alpha - trifluoro-m-tolyl)acetonitriles,acetamides and acetic acids |
| BE760968A (en) * | 1970-12-29 | 1971-06-29 | P R B En Neerlandais P R B N V | Opt 2,3-subst phenyl acetic acid and derivpl |
| DE4415681A1 (de) * | 1994-05-04 | 1995-11-16 | Hoechst Ag | Verfahren zur Herstellung von Arylessigsäurederivaten durch Carbonylierung von Arylmethylhalogeniden |
-
1996
- 1996-06-17 GB GBGB9612623.0A patent/GB9612623D0/en active Pending
-
1997
- 1997-05-21 US US09/202,401 patent/US6008381A/en not_active Expired - Lifetime
- 1997-05-21 PT PT97923223T patent/PT906304E/pt unknown
- 1997-05-21 BR BR9709735A patent/BR9709735A/pt not_active IP Right Cessation
- 1997-05-21 AT AT97923223T patent/ATE203241T1/de active
- 1997-05-21 CN CN97195508A patent/CN1102590C/zh not_active Expired - Fee Related
- 1997-05-21 ES ES97923223T patent/ES2158561T3/es not_active Expired - Lifetime
- 1997-05-21 IL IL12750297A patent/IL127502A/en not_active IP Right Cessation
- 1997-05-21 DK DK97923223T patent/DK0906304T3/da active
- 1997-05-21 AU AU29086/97A patent/AU2908697A/en not_active Abandoned
- 1997-05-21 WO PCT/GB1997/001391 patent/WO1997048692A1/en not_active Ceased
- 1997-05-21 JP JP50246598A patent/JP3830975B2/ja not_active Expired - Fee Related
- 1997-05-21 EP EP97923223A patent/EP0906304B1/en not_active Expired - Lifetime
- 1997-05-21 DE DE69705721T patent/DE69705721T2/de not_active Expired - Lifetime
- 1997-05-27 ZA ZA9704629A patent/ZA974629B/xx unknown
- 1997-05-30 TW TW086107409A patent/TW505641B/zh not_active IP Right Cessation
- 1997-06-02 IN IN1461DE1997 patent/IN186158B/en unknown
-
2001
- 2001-07-19 GR GR20010400125T patent/GR3036239T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT906304E (pt) | 2001-10-31 |
| ZA974629B (en) | 1997-12-17 |
| BR9709735A (pt) | 1999-08-10 |
| AU2908697A (en) | 1998-01-07 |
| JP2000512983A (ja) | 2000-10-03 |
| ES2158561T3 (es) | 2001-09-01 |
| DK0906304T3 (da) | 2001-09-24 |
| US6008381A (en) | 1999-12-28 |
| EP0906304A1 (en) | 1999-04-07 |
| CN1102590C (zh) | 2003-03-05 |
| GR3036239T3 (en) | 2001-10-31 |
| JP3830975B2 (ja) | 2006-10-11 |
| IN186158B (enExample) | 2001-06-30 |
| CN1222150A (zh) | 1999-07-07 |
| WO1997048692A1 (en) | 1997-12-24 |
| EP0906304B1 (en) | 2001-07-18 |
| GB9612623D0 (en) | 1996-08-21 |
| IL127502A0 (en) | 1999-10-28 |
| TW505641B (en) | 2002-10-11 |
| ATE203241T1 (de) | 2001-08-15 |
| DE69705721D1 (de) | 2001-08-23 |
| DE69705721T2 (de) | 2002-05-08 |
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