IL131208A - סינטזה של מיו-אינוזיטול פוספטים - Google Patents
סינטזה של מיו-אינוזיטול פוספטיםInfo
- Publication number
- IL131208A IL131208A IL13120898A IL13120898A IL131208A IL 131208 A IL131208 A IL 131208A IL 13120898 A IL13120898 A IL 13120898A IL 13120898 A IL13120898 A IL 13120898A IL 131208 A IL131208 A IL 131208A
- Authority
- IL
- Israel
- Prior art keywords
- inositol
- myo
- isopropylidene
- benzyl
- product
- Prior art date
Links
- 229960000367 inositol Drugs 0.000 title claims abstract description 112
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 230000015572 biosynthetic process Effects 0.000 title description 18
- 238000003786 synthesis reaction Methods 0.000 title description 18
- 229910019142 PO4 Inorganic materials 0.000 title description 5
- -1 myo-inositol phosphates Chemical class 0.000 title description 2
- 235000021317 phosphate Nutrition 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 39
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims abstract description 21
- 238000005574 benzylation reaction Methods 0.000 claims abstract description 8
- 238000002955 isolation Methods 0.000 claims abstract description 8
- 238000005797 stannylation reaction Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 40
- 239000007983 Tris buffer Substances 0.000 claims description 24
- HDFFVHSMHLDSLO-UHFFFAOYSA-M dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-M 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- MMWCIQZXVOZEGG-XJTPDSDZSA-N D-myo-Inositol 1,4,5-trisphosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H](O)[C@@H]1OP(O)(O)=O MMWCIQZXVOZEGG-XJTPDSDZSA-N 0.000 claims description 9
- 238000004587 chromatography analysis Methods 0.000 claims description 9
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 7
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
- 238000011065 in-situ storage Methods 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 230000020477 pH reduction Effects 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 238000005731 phosphitylation reaction Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 claims description 4
- 230000026731 phosphorylation Effects 0.000 claims description 4
- 238000006366 phosphorylation reaction Methods 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- KKSOKTQAWHCIMG-UHFFFAOYSA-N tert-butyl 4-bromo-2-methylbenzoate Chemical compound CC1=CC(Br)=CC=C1C(=O)OC(C)(C)C KKSOKTQAWHCIMG-UHFFFAOYSA-N 0.000 claims description 4
- KIUPCUCGVCGPPA-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) carbonochloridate Chemical compound CC(C)C1CCC(C)CC1OC(Cl)=O KIUPCUCGVCGPPA-UHFFFAOYSA-N 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims description 3
- SGECHWQKWQJBAO-UHFFFAOYSA-N n-bis(phenylmethoxy)phosphoryl-n-propan-2-ylpropan-2-amine Chemical compound C=1C=CC=CC=1COP(=O)(N(C(C)C)C(C)C)OCC1=CC=CC=C1 SGECHWQKWQJBAO-UHFFFAOYSA-N 0.000 claims description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
- 244000046052 Phaseolus vulgaris Species 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000004001 inositols Chemical class 0.000 description 5
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 230000011664 signaling Effects 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 101150037263 PIP2 gene Proteins 0.000 description 2
- 102000003923 Protein Kinase C Human genes 0.000 description 2
- 108090000315 Protein Kinase C Proteins 0.000 description 2
- 101100262439 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UBA2 gene Proteins 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001982 diacylglycerols Chemical class 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- FMNQRUKVXAQEAZ-JNRFBPFXSA-N (5z,8s,9r,10e,12s)-9,12-dihydroxy-8-[(1s)-1-hydroxy-3-oxopropyl]heptadeca-5,10-dienoic acid Chemical compound CCCCC[C@H](O)\C=C\[C@@H](O)[C@H]([C@@H](O)CC=O)C\C=C/CCCC(O)=O FMNQRUKVXAQEAZ-JNRFBPFXSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- CNWINRVXAYPOMW-FCNJXWMTSA-N 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(O)(=O)O[C@@H]1[C@H](O)[C@H](O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H]1O CNWINRVXAYPOMW-FCNJXWMTSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 208000037273 Pathologic Processes Diseases 0.000 description 1
- XNRNNGPBEPRNAR-UHFFFAOYSA-N Thromboxane B2 Natural products CCCCCC(O)C=CC1OC(O)CC(O)C1CC=CCCCC(O)=O XNRNNGPBEPRNAR-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000009134 cell regulation Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- DZFYOYRNBGNPJW-UHFFFAOYSA-N ethoxythallium Chemical compound [Tl+].CC[O-] DZFYOYRNBGNPJW-UHFFFAOYSA-N 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000006525 intracellular process Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 229940067626 phosphatidylinositols Drugs 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/794,957 US5756774A (en) | 1997-02-04 | 1997-02-04 | Synthesis of myo-inositol phosphates |
| PCT/US1998/002205 WO1998033790A1 (en) | 1997-02-04 | 1998-02-04 | Novel synthesis of myo-inositol phosphates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL131208A0 IL131208A0 (en) | 2001-01-28 |
| IL131208A true IL131208A (he) | 2002-11-10 |
Family
ID=25164196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13120898A IL131208A (he) | 1997-02-04 | 1998-02-04 | סינטזה של מיו-אינוזיטול פוספטים |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5756774A (he) |
| EP (1) | EP0975620A4 (he) |
| JP (1) | JP2002511839A (he) |
| KR (1) | KR20000070758A (he) |
| CN (1) | CN1122030C (he) |
| AU (1) | AU725427B2 (he) |
| BR (1) | BR9807656A (he) |
| CA (1) | CA2280132A1 (he) |
| CZ (1) | CZ278299A3 (he) |
| HU (1) | HUP0101018A3 (he) |
| IL (1) | IL131208A (he) |
| NO (1) | NO993754L (he) |
| NZ (1) | NZ337047A (he) |
| PL (1) | PL337604A1 (he) |
| SK (1) | SK283843B6 (he) |
| TR (1) | TR199901851T2 (he) |
| WO (1) | WO1998033790A1 (he) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6153736A (en) * | 1995-09-27 | 2000-11-28 | The Liposome Company, Inc. | Modified ether glyceroglycolipids |
| EP1341800A2 (en) | 2000-12-11 | 2003-09-10 | The Research Foundation Of the City university of New York | C-glucosyl ether lipids |
| WO2010057515A1 (en) * | 2008-11-21 | 2010-05-27 | Synthon B.V. | Levocetirizine by menthyl intermediate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5292913A (en) * | 1986-03-11 | 1994-03-08 | Mitsui Toatsu Chemicals, Incorporated | Myoinositol derivatives and preparation process thereof |
| US4873355A (en) * | 1987-05-29 | 1989-10-10 | E. I. Du Pont De Nemours And Company | Process for regioselectively preparing phosphorylated inositols and other cyclitols |
| ES2050592B1 (es) * | 1991-12-26 | 1994-12-16 | Europharma Sa | Metodo para preparar los precursores y productos intermedios para la sintesis de mio-inositolfosfatos y glucosil-fosfatidil-inositoles, asi como preparar estos. |
| US5260472A (en) * | 1992-01-29 | 1993-11-09 | The Board Of Governors For Higher Education State Of Rhode Island And Providence Plantations | Efficient chemoenzymatic synthesis of D-myo-inositol 1,4,5-triphosphate, D-myo-inositol 1,3,4-triphosphate, and D-myo-inositol 1,3,4,5-tetraphosphate |
-
1997
- 1997-02-04 US US08/794,957 patent/US5756774A/en not_active Expired - Fee Related
-
1998
- 1998-02-04 KR KR1019997007017A patent/KR20000070758A/ko not_active Ceased
- 1998-02-04 NZ NZ337047A patent/NZ337047A/xx unknown
- 1998-02-04 WO PCT/US1998/002205 patent/WO1998033790A1/en not_active Ceased
- 1998-02-04 HU HU0101018A patent/HUP0101018A3/hu unknown
- 1998-02-04 CA CA002280132A patent/CA2280132A1/en not_active Abandoned
- 1998-02-04 IL IL13120898A patent/IL131208A/he not_active IP Right Cessation
- 1998-02-04 JP JP52600098A patent/JP2002511839A/ja active Pending
- 1998-02-04 AU AU61456/98A patent/AU725427B2/en not_active Ceased
- 1998-02-04 CN CN98803739A patent/CN1122030C/zh not_active Expired - Fee Related
- 1998-02-04 CZ CZ992782A patent/CZ278299A3/cs unknown
- 1998-02-04 TR TR1999/01851T patent/TR199901851T2/xx unknown
- 1998-02-04 SK SK1061-99A patent/SK283843B6/sk unknown
- 1998-02-04 EP EP98906154A patent/EP0975620A4/en not_active Withdrawn
- 1998-02-04 BR BR9807656-6A patent/BR9807656A/pt not_active IP Right Cessation
- 1998-02-04 PL PL98337604A patent/PL337604A1/xx unknown
-
1999
- 1999-08-03 NO NO993754A patent/NO993754L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1122030C (zh) | 2003-09-24 |
| KR20000070758A (ko) | 2000-11-25 |
| AU6145698A (en) | 1998-08-25 |
| EP0975620A4 (en) | 2001-01-31 |
| NZ337047A (en) | 2002-09-27 |
| HUP0101018A2 (hu) | 2001-08-28 |
| AU725427B2 (en) | 2000-10-12 |
| CA2280132A1 (en) | 1998-08-06 |
| PL337604A1 (en) | 2000-08-28 |
| JP2002511839A (ja) | 2002-04-16 |
| HUP0101018A3 (en) | 2003-07-28 |
| IL131208A0 (en) | 2001-01-28 |
| BR9807656A (pt) | 2000-02-15 |
| CZ278299A3 (cs) | 1999-11-17 |
| EP0975620A1 (en) | 2000-02-02 |
| SK106199A3 (en) | 2000-06-12 |
| NO993754D0 (no) | 1999-08-03 |
| WO1998033790A1 (en) | 1998-08-06 |
| US5756774A (en) | 1998-05-26 |
| TR199901851T2 (xx) | 2001-03-21 |
| SK283843B6 (sk) | 2004-03-02 |
| CN1265105A (zh) | 2000-08-30 |
| NO993754L (no) | 1999-09-09 |
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