ES2012941A6 - Procedimiento para preparar derivados de 1,2-dioxetano - Google Patents
Procedimiento para preparar derivados de 1,2-dioxetanoInfo
- Publication number
- ES2012941A6 ES2012941A6 ES8804034A ES8804034A ES2012941A6 ES 2012941 A6 ES2012941 A6 ES 2012941A6 ES 8804034 A ES8804034 A ES 8804034A ES 8804034 A ES8804034 A ES 8804034A ES 2012941 A6 ES2012941 A6 ES 2012941A6
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compounds
- reacting
- compound
- produced
- 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.)
- Expired - Lifetime
Links
- BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical class C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- -1 alkali metal alkoxide Chemical class 0.000 abstract 2
- 238000003556 assay Methods 0.000 abstract 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 108020003215 DNA Probes Proteins 0.000 abstract 1
- 239000003298 DNA probe Substances 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 239000002879 Lewis base Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000003018 immunoassay Methods 0.000 abstract 1
- 150000007527 lewis bases Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
-
- 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
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
- C07F9/65512—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring condensed with carbocyclic rings or carbocyclic ring 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
- G01N21/76—Chemiluminescence; Bioluminescence
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/581—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with enzyme label (including co-enzymes, co-factors, enzyme inhibitors or substrates)
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Pathology (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- General Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Wood Science & Technology (AREA)
- Cell Biology (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plasma & Fusion (AREA)
- General Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Luminescent Compositions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
PROCEDIMIENTO PARA PREPARAR DERIVADOS DE 1,2-DIOXETANO DE FORMULA: FORMULA DONDE T ES POLICICLOALQUILIDENO, TAL COMO ADAMANT-2-ILIDENO, R Y R1 SON ALQUILO, ARILALQUILO O CICLOALQUILO C1-20, E Y ES UN CROMOFORO FLUORESCENTE, TAL COMO M-FENILENO. CONSISTE EN HACER REACCIONAR UN COMPUESTO DE FORMULA: FORMULA DONDE T, R1 E Y SON COMO ANTES, CON UN AGENTE R-ILANTE, TAL COMO R2SO4, EN PRESENCIA DE UN ALCOXIDO DE METAL ALCALINO Y EN EL SENO DE UN DISOLVENTE APROTICO POLAR. EXISTEN OTRAS VIAS PARA PREPARAR LOS DERIVADOS DE LA FORMULA INDICADA, QUE SE DESCRIBEN EN LA MEMORIA. LOS COMPUESTOS OBTENIDOS SON UTILES EN INMUNOANALISIS QUIMIOLUMINISCENTES, ANALISIS DE SONDAS DE ADN Y ANALISIS DIRECTOS DE ENZIMAS.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14019787A | 1987-12-31 | 1987-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2012941A6 true ES2012941A6 (es) | 1990-04-16 |
Family
ID=22490169
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES8804034A Expired - Lifetime ES2012941A6 (es) | 1987-12-31 | 1988-12-30 | Procedimiento para preparar derivados de 1,2-dioxetano |
Country Status (13)
Country | Link |
---|---|
US (1) | US6417380B1 (es) |
EP (2) | EP0368946B1 (es) |
JP (9) | JPH0731201B2 (es) |
AU (1) | AU2945189A (es) |
CA (1) | CA1341210C (es) |
DE (2) | DE68929060T2 (es) |
ES (1) | ES2012941A6 (es) |
GR (1) | GR1000118B (es) |
IL (1) | IL88798A (es) |
MX (1) | MX14411A (es) |
NZ (1) | NZ227525A (es) |
WO (1) | WO1989006226A1 (es) |
ZA (1) | ZA889659B (es) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5004565A (en) * | 1986-07-17 | 1991-04-02 | The Board Of Governors Of Wayne State University | Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes |
US4956477A (en) * | 1987-12-31 | 1990-09-11 | Tropix, Inc. | Synthesis of 1,2-dioxetanes |
US4978614A (en) * | 1988-10-26 | 1990-12-18 | Tropix, Inc. | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
US4952707A (en) * | 1988-06-30 | 1990-08-28 | Tropix, Inc. | Enzymatically-cleavable chemiluminescent fused polycyclic ring-containing 1,2-dioxetanes |
US4931569A (en) * | 1988-09-14 | 1990-06-05 | Tropix, Inc. | Purification of stable water-soluble dioxetanes |
US6022964A (en) * | 1989-07-17 | 2000-02-08 | Tropix, Inc. | Chemiluminescent 1,2-dioxetanes |
EP0441948A4 (en) * | 1989-09-06 | 1992-06-03 | Tropix, Inc. | Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor |
US5362916A (en) * | 1989-09-06 | 1994-11-08 | Tropix, Inc. | Synthesis of mercaptaryl or hydroxyaryl enol ether alkali metal salts |
US5225584A (en) * | 1989-09-06 | 1993-07-06 | Tropix, Inc. | Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor |
JP3464798B2 (ja) * | 1992-07-31 | 2003-11-10 | デイド・ベーリング・マルブルク・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 光活性化化学発光基質 |
KR0148439B1 (ko) * | 1994-03-11 | 1998-11-02 | 마사까쓰 마쓰모또 | 1,2-디옥세탄 유도체 |
US5631167A (en) * | 1995-07-31 | 1997-05-20 | Bayer Corporation | Capsule chemistry analytical methods employing dioxetane chemiluminescence |
US5777135A (en) * | 1995-07-31 | 1998-07-07 | Lumigen, Inc. | Di-substituted 1,2-dioxetane compounds having increased water solubility and assay compositions |
US5783381A (en) * | 1995-10-19 | 1998-07-21 | Tropix, Inc. | Chemiluminescent 1,2-dioxetanes |
US6355441B1 (en) * | 1998-07-28 | 2002-03-12 | Tropix, Inc. | Benzothiazole dioxetanes |
US6660529B2 (en) * | 1998-07-28 | 2003-12-09 | Pe Corporation | Heteroaryl substituted benzothiazole dioxetanes |
AU4342100A (en) * | 1999-04-16 | 2000-11-02 | Zymetx, Inc. | Viral detection method using viral encoded enzymes and chemiluminescent substrates |
AU2001281730A1 (en) * | 2000-07-26 | 2002-02-05 | Chemometec A/S | Spatially resolved enzyme-linked assay |
EP1342724B1 (en) | 2002-03-08 | 2016-01-06 | Tosoh Corporation | 1,2-dioxetane derivates and reagents employing them |
JP4259229B2 (ja) | 2003-08-28 | 2009-04-30 | 東ソー株式会社 | 1,2−ジオキセタンの化学発光方法および化学発光用組成物 |
JP2012140330A (ja) * | 2010-12-28 | 2012-07-26 | Tosoh Corp | 水溶性リン酸エステルの精製方法 |
EP2892900B1 (en) | 2012-09-10 | 2017-08-16 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
JP6475401B1 (ja) | 2017-10-13 | 2019-02-27 | 三菱エンジニアリングプラスチックス株式会社 | ポリカーボネート樹脂組成物 |
JP7007862B2 (ja) * | 2017-10-31 | 2022-01-25 | アークレイ株式会社 | 化学発光試薬組成物及び化学発光試薬キット |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2909557A (en) * | 1955-09-07 | 1959-10-20 | Bayer Ag | Thiophosphoric acid esters and their production |
DE1810343U (de) | 1960-02-29 | 1960-04-28 | Mak Maschb Kiel G M B H | Vorrichtung zum befestigen von achshaltertegen am rahmen von schienenfahrzeugen. |
NL6716437A (es) | 1967-12-02 | 1969-06-04 | ||
US3711556A (en) | 1968-06-13 | 1973-01-16 | Du Pont | 2-(bis(p-substituted phenyl)methylene)adamantanes |
GB1497109A (en) * | 1975-10-29 | 1978-01-05 | Beecham Group Ltd | Naphthalene derivatives |
JPS57159499A (en) * | 1981-03-26 | 1982-10-01 | Fuji Photo Film Co Ltd | Substrate for determining alkaline phosphatase and determining method |
JPS62176941A (ja) * | 1986-01-28 | 1987-08-03 | Sumitomo Electric Ind Ltd | 光フアイバ |
JPS639377A (ja) * | 1986-06-30 | 1988-01-16 | Sony Corp | マルチチヤンネル録画装置 |
US5707559A (en) * | 1986-07-17 | 1998-01-13 | Tropix, Inc. | Chemiluminescent 1,2-dioxetane compounds |
US4983779A (en) | 1986-07-17 | 1991-01-08 | The Board Of Governors Of Wayne State University | Process for the preparation of vinyl ethers |
JPH0521918A (ja) * | 1991-07-11 | 1993-01-29 | Nippon Cement Co Ltd | セラミツクス回路基板用導電パターン形成用粉末組成物 |
JP3217396B2 (ja) * | 1991-08-16 | 2001-10-09 | オリンパス光学工業株式会社 | 顕微鏡の粗微動機構 |
JPH0723989B2 (ja) * | 1992-08-03 | 1995-03-15 | ビソーディスプレイ株式会社 | スクリーン装置 |
JPH0733346A (ja) * | 1993-07-20 | 1995-02-03 | Hitachi Building Syst Eng & Service Co Ltd | エレベータの着床制御装置 |
DE4423811C1 (de) * | 1994-07-06 | 1996-01-18 | Fraunhofer Ges Forschung | Hydrolysierbare und polymerisierbare Silane, Verfahren zu deren Herstellung und deren Verwendung |
-
1988
- 1988-07-25 JP JP63185319A patent/JPH0731201B2/ja not_active Expired - Lifetime
- 1988-12-26 IL IL8879888A patent/IL88798A/en not_active IP Right Cessation
- 1988-12-28 ZA ZA889659A patent/ZA889659B/xx unknown
- 1988-12-29 GR GR880100867A patent/GR1000118B/el unknown
- 1988-12-30 MX MX1441188A patent/MX14411A/es unknown
- 1988-12-30 ES ES8804034A patent/ES2012941A6/es not_active Expired - Lifetime
-
1989
- 1989-01-03 CA CA000587441A patent/CA1341210C/en not_active Expired - Lifetime
- 1989-01-03 DE DE68929060T patent/DE68929060T2/de not_active Expired - Lifetime
- 1989-01-03 EP EP89901890A patent/EP0368946B1/en not_active Expired - Lifetime
- 1989-01-03 JP JP1501800A patent/JP3025280B2/ja not_active Expired - Lifetime
- 1989-01-03 WO PCT/US1989/000016 patent/WO1989006226A1/en active IP Right Grant
- 1989-01-03 DE DE68918230T patent/DE68918230T2/de not_active Expired - Lifetime
- 1989-01-03 EP EP93114829A patent/EP0582317B1/en not_active Expired - Lifetime
- 1989-01-03 AU AU29451/89A patent/AU2945189A/en not_active Abandoned
- 1989-01-05 NZ NZ227525A patent/NZ227525A/en unknown
-
1990
- 1990-02-14 JP JP2033599A patent/JPH03139298A/ja active Pending
- 1990-02-14 JP JP2033598A patent/JPH03123791A/ja active Granted
- 1990-02-14 JP JP2033597A patent/JPH0372489A/ja active Granted
-
1992
- 1992-11-11 JP JP4324674A patent/JPH0651708B2/ja not_active Expired - Lifetime
-
1993
- 1993-02-16 JP JP5026654A patent/JPH0733346B2/ja not_active Expired - Lifetime
-
1999
- 1999-04-20 JP JP11234599A patent/JP3280342B2/ja not_active Expired - Lifetime
- 1999-04-20 JP JP11112353A patent/JPH11335342A/ja active Pending
-
2000
- 2000-08-02 US US09/631,300 patent/US6417380B1/en not_active Expired - Fee Related
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