DK0516410T3 - Hidtil ukendt syntese af 19-nor-vitamin D-forbindelser - Google Patents
Hidtil ukendt syntese af 19-nor-vitamin D-forbindelserInfo
- Publication number
- DK0516410T3 DK0516410T3 DK92304837T DK92304837T DK0516410T3 DK 0516410 T3 DK0516410 T3 DK 0516410T3 DK 92304837 T DK92304837 T DK 92304837T DK 92304837 T DK92304837 T DK 92304837T DK 0516410 T3 DK0516410 T3 DK 0516410T3
- Authority
- DK
- Denmark
- Prior art keywords
- vitamin
- compounds
- synthesis
- hitherto unknown
- alpha
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000003786 synthesis reaction Methods 0.000 title abstract 4
- PKFBWEUIKKCWEW-WEZTXPJVSA-N (1r,3r)-5-[(2e)-2-[(1r,3as,7ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol Chemical class C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1C[C@@H](O)C[C@H](O)C1 PKFBWEUIKKCWEW-WEZTXPJVSA-N 0.000 title abstract 3
- -1 lithium anion Chemical class 0.000 abstract 2
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 abstract 1
- 239000011612 calcitriol Substances 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/532—Cycloaliphatic phosphine oxides or thioxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70591791A | 1991-05-28 | 1991-05-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
DK0516410T3 true DK0516410T3 (da) | 1998-10-26 |
Family
ID=24835479
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK92304837T DK0516410T3 (da) | 1991-05-28 | 1992-05-28 | Hidtil ukendt syntese af 19-nor-vitamin D-forbindelser |
Country Status (11)
Country | Link |
---|---|
US (7) | US5281731A (da) |
EP (1) | EP0516410B1 (da) |
JP (4) | JP2648845B2 (da) |
KR (3) | KR0160784B1 (da) |
AT (1) | ATE168996T1 (da) |
AU (2) | AU650751B2 (da) |
CA (2) | CA2191993C (da) |
DE (1) | DE69226402T2 (da) |
DK (1) | DK0516410T3 (da) |
ES (1) | ES2118794T3 (da) |
IE (1) | IE921700A1 (da) |
Families Citing this family (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1333616C (en) * | 1989-03-09 | 1994-12-20 | Hector F. Deluca | 19-nor-vitamin d compounds |
US5260290A (en) * | 1990-02-14 | 1993-11-09 | Wisconsin Alumni Research Foundation | Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives |
US20040009958A1 (en) * | 1991-01-08 | 2004-01-15 | Bone Care International, Inc. | Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2 |
US6538037B2 (en) | 1991-01-08 | 2003-03-25 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-dihydroxyvitamin D2 |
AU650751B2 (en) * | 1991-05-28 | 1994-06-30 | Wisconsin Alumni Research Foundation | Novel synthesis of 19-nor vitamin D compounds |
AU666563B2 (en) * | 1992-08-07 | 1996-02-15 | Wisconsin Alumni Research Foundation | Preparation of 19-nor-vitamin D compounds |
US5464866A (en) * | 1992-08-17 | 1995-11-07 | Alcon Laboratories, Inc. | Substituted hydrindanes for the treatment of angiogenesis-dependent diseases |
CA2096105A1 (en) * | 1992-10-07 | 1994-04-08 | Enrico Giuseppe Baggiolini (Deceased) | Vitamin d3 fluorinated analogs |
US5753638A (en) * | 1992-10-07 | 1998-05-19 | Hoffmann-La Roche Inc. | Method of treating hyperproliferative skin disease with Vitamin D3 fluorinated analogs |
DE69400495T2 (de) * | 1993-04-05 | 1997-04-30 | Wisconsin Alumni Res Found | 19-Nor-vitamin-D3-Verbindung mit einem Substituent an die 2. Stelle |
CA2166898C (en) * | 1993-07-09 | 2004-09-07 | Roger Bouillon | Novel structural analogues of vitamin d |
US5763429A (en) * | 1993-09-10 | 1998-06-09 | Bone Care International, Inc. | Method of treating prostatic diseases using active vitamin D analogues |
US5428029A (en) * | 1993-11-24 | 1995-06-27 | Hoffmann-La Roche Inc. | Vitamin D3 fluorinated analogs |
DE69507714D1 (de) * | 1994-11-21 | 1999-03-18 | Wisconsin Alumni Res Found | 18,19-dinor-vitamin-d-derivate |
US5597815A (en) * | 1995-07-13 | 1997-01-28 | Wisconsin Alumni Research Foundation | Prevention of hyperphosphatemia in kidney disorder patients |
US6573256B2 (en) | 1996-12-30 | 2003-06-03 | Bone Care International, Inc. | Method of inhibiting angiogenesis using active vitamin D analogues |
US20020128240A1 (en) * | 1996-12-30 | 2002-09-12 | Bone Care International, Inc. | Treatment of hyperproliferative diseases using active vitamin D analogues |
US6503893B2 (en) | 1996-12-30 | 2003-01-07 | Bone Care International, Inc. | Method of treating hyperproliferative diseases using active vitamin D analogues |
US6566353B2 (en) * | 1996-12-30 | 2003-05-20 | Bone Care International, Inc. | Method of treating malignancy associated hypercalcemia using active vitamin D analogues |
US5945410A (en) | 1997-03-17 | 1999-08-31 | Wisconsin Alumni Research Foundation | 2-alkyl-19-nor-vitamin D compounds |
US6306844B1 (en) | 1997-03-17 | 2001-10-23 | Wisconsin Alumni Research Foundation | Use of 2α-methyl-19-nor-20(S)-1α, 25-dihydroxyvitamin D3 to increase bone strength |
US6316642B1 (en) | 1997-03-17 | 2001-11-13 | Wisconsin Alumni Research Foundation | 26,27-Homologated-20-EPI-2alkyl-19-nor-vitamin D compounds |
US6392071B1 (en) | 1997-03-17 | 2002-05-21 | Wisconsin Alumni: Research Foundation | 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds |
US5843928A (en) * | 1997-03-17 | 1998-12-01 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin D compounds |
EP0983221B1 (en) * | 1997-05-23 | 2002-04-03 | Basilea Pharmaceutica AG | Cyclohexanediol derivatives |
US5936105A (en) * | 1997-06-13 | 1999-08-10 | Tetrionics, Inc. | 14-EPI-19-nor-vitamin D compounds and methods |
US6087350A (en) * | 1997-08-29 | 2000-07-11 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Use of pretreatment chemicals to enhance efficacy of cytotoxic agents |
AU762481C (en) * | 1998-03-27 | 2004-08-19 | Oregon Health Sciences University | Vitamin D and its analogs in the treatment of tumors and other hyperproliferative disorders |
US6080879A (en) * | 1998-05-19 | 2000-06-27 | Tetrionics, Inc. | Hexafluoro-vitamin synthesis and crystallization method, solvent and product |
US6114317A (en) | 1998-05-21 | 2000-09-05 | Wisconsin Alumni Research Foundation | Method of locking 1α-OH of vitamin D compounds in axial orientation |
US5962707A (en) * | 1998-08-18 | 1999-10-05 | Wisconsin Alumni Research Foundation | 19-nor-vitamin D3 compounds with calcemic activity |
US6603030B1 (en) | 1999-04-22 | 2003-08-05 | Hoffman-La Roche Inc. | Process for producing phosphineoxide vitamin D precursors |
US6310262B1 (en) | 1999-10-18 | 2001-10-30 | Basilea Pharmaceutica Ag | Process for preparing retiferol derivatives |
DE10019861A1 (de) * | 2000-04-18 | 2001-10-31 | Schering Ag | Neues Synthesezwischenprodukt, seine mikrobiologische Herstellung und Verwendung zur Synthese von Vitamin D-Derivaten |
WO2001092221A1 (en) | 2000-05-31 | 2001-12-06 | Wisconsin Alumni Research Foundation | 2-ethyl and 2-ethylidene-19-nor-vitamin d compounds |
JP4811547B2 (ja) * | 2000-10-24 | 2011-11-09 | 史衛 佐藤 | 光学活性シクロヘキセン化合物の製造法及びこの製造に用いる光学活性シクロヘキセン誘導体 |
US6683219B2 (en) * | 2001-07-30 | 2004-01-27 | Wisconsin Alumni Research Foundation | Synthesis of A-ring synthon of 19-nor-1α,25-dihydroxyvitamin D3 from (D)-glucose |
US20040258801A1 (en) * | 2001-09-27 | 2004-12-23 | Alvin Ling | Vitamin fortification of foodstuffs |
US6846811B2 (en) * | 2002-04-22 | 2005-01-25 | Wisconsin Alumni Research Foundation | (20S) 1α-hydroxy-2α-methyl and 2β-methyl-19-nor-vitamin D3 and their uses |
US7023347B2 (en) * | 2002-08-02 | 2006-04-04 | Symbol Technologies, Inc. | Method and system for forming a die frame and for transferring dies therewith |
US20060293291A1 (en) | 2003-04-10 | 2006-12-28 | Deluca Hector F | 2-Propylidene-19-nor-vitamin d compounds |
US20050005434A1 (en) * | 2003-06-12 | 2005-01-13 | Matrics, Inc. | Method, system, and apparatus for high volume transfer of dies |
US6894037B2 (en) | 2003-07-03 | 2005-05-17 | Wisconsin Alumni Research Foundation | 2-methylene-19-nor-20(S)-25-methyl-1α-hydroxycalciferol and its uses |
US7713951B2 (en) | 2004-04-09 | 2010-05-11 | Wisconsin Alumni Research Foundation | 2-alkylidene-18,19-dinor-vitamin D compounds |
WO2006012358A2 (en) * | 2004-06-29 | 2006-02-02 | Symbol Technologies, Inc. | Systems and methods for testing radio frequency identification tags |
US7094775B2 (en) * | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
US20060003950A1 (en) * | 2004-06-30 | 2006-01-05 | Bone Care International, Inc. | Method of treating prostatic diseases using a combination of vitamin D analogues and other agents |
US20060225273A1 (en) * | 2005-03-29 | 2006-10-12 | Symbol Technologies, Inc. | Transferring die(s) from an intermediate surface to a substrate |
CN101223135A (zh) * | 2005-07-18 | 2008-07-16 | 特瓦制药工业有限公司 | 帕立骨化醇的制备 |
US20070107186A1 (en) * | 2005-11-04 | 2007-05-17 | Symbol Technologies, Inc. | Method and system for high volume transfer of dies to substrates |
US20070131016A1 (en) * | 2005-12-13 | 2007-06-14 | Symbol Technologies, Inc. | Transferring die(s) from an intermediate surface to a substrate |
US20070139057A1 (en) * | 2005-12-15 | 2007-06-21 | Symbol Technologies, Inc. | System and method for radio frequency identification tag direct connection test |
WO2007105773A1 (ja) | 2006-03-15 | 2007-09-20 | Mercian Corporation | インデン誘導体の製造方法およびその製造中間体 |
NZ571896A (en) | 2006-04-05 | 2011-09-30 | Wisconsin Alumni Res Found | 1-Alpha.-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin D compounds and methods of making and use thereof |
US20070244657A1 (en) * | 2006-04-11 | 2007-10-18 | Drago Randall A | Methods and systems for testing radio frequency identification (RFID) tags having multiple antennas |
WO2008053961A1 (fr) | 2006-11-02 | 2008-05-08 | Mercian Corporation | Procédé et intermédiaire pour la fabrication du dérivé 1-hydroxy-19-norcyclovitamine d |
JP5480131B2 (ja) * | 2007-05-30 | 2014-04-23 | シトクロマ インコーポレイテッド | ホスフィンオキシドビタミンd前駆物質の製造方法 |
US8377913B2 (en) * | 2007-11-20 | 2013-02-19 | Abbvie Inc. | Vitamin D receptor activators and methods of making |
US20090275768A1 (en) | 2008-04-30 | 2009-11-05 | Formosa Laboratories, Inc. | Preparation of Paricalcitol |
CA2639477C (en) * | 2008-09-11 | 2016-03-22 | Alphora Research Inc. | Paricalcitol purification |
US8013176B2 (en) * | 2008-09-11 | 2011-09-06 | Alphora Research Inc. | Paricalcitol purification |
MX339746B (es) | 2009-01-27 | 2016-06-08 | Berg Llc | Vitamina d3 y análogos de la misma para aliviar efectos secundarios asociados con la quimioterapia. |
JP5978130B2 (ja) | 2009-08-14 | 2016-08-24 | バーグ エルエルシー | 脱毛症を治療するためのビタミンd3およびその類似体 |
CN101671288B (zh) * | 2009-10-14 | 2013-10-30 | 兰州大学 | 帕立骨化醇的中间体的制备方法 |
WO2014194133A1 (en) | 2013-05-29 | 2014-12-04 | Berg Llc | Preventing or mitigating chemotherapy induced alopecia using vitamin d |
CN107501317B (zh) * | 2017-09-13 | 2019-08-16 | 上海皓元医药股份有限公司 | 一种帕立骨化醇中间体的制备方法 |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4607118A (en) * | 1981-04-30 | 1986-08-19 | Philip Morris Incorporated | Flavor-release β-hydroxy-ester compositions |
DE3471928D1 (en) * | 1983-01-28 | 1988-07-14 | Hoffmann La Roche | Process for the preparation of cholecalciferol derivatives |
US4508651A (en) * | 1983-03-21 | 1985-04-02 | Hoffmann-La Roche Inc. | Synthesis of 1α,25-dihydroxyergocalciferol |
DE3476195D1 (en) * | 1983-05-18 | 1989-02-23 | Ciba Geigy Ag | Cyclohexanedione-carboxylic-acid derivatives having a herbicidal and plant growth regulating activity |
US4668817A (en) * | 1983-12-21 | 1987-05-26 | International Flavors & Fragrances Inc. | Alkyl substituted para-carboalkoxy cyclohexanones |
US4681976A (en) * | 1983-12-21 | 1987-07-21 | International Flavors & Fragrances Inc. | Process for preparing alkyl substituted and unsubstituted para-carboalkoxy cyclohexanones |
EP0154185B1 (en) * | 1984-02-08 | 1988-10-05 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Calciferol derivatives |
US4613594A (en) * | 1984-11-16 | 1986-09-23 | Hoffmann-La Roche Inc. | Fluorinated vitamin D3 compounds |
US4612308A (en) * | 1984-11-29 | 1986-09-16 | Hoffmann-La Roche Inc. | 25,26-Dehydro-1α,23(S,R)-dihydroxycholecalciferol and its epimers |
ZA859138B (en) * | 1984-12-19 | 1986-08-27 | Hoffmann La Roche | Cholecalciferol derivatives |
US4755329A (en) * | 1985-06-10 | 1988-07-05 | Wisconsin Alumni Research Foundation | Process and intermediates for preparing 1α-hydroxyvitamin D compounds |
AU603340B2 (en) * | 1985-08-02 | 1990-11-15 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Novel vitamin d analogues |
IL77668A (en) * | 1986-01-21 | 1989-03-31 | Teva Pharma | Production of cholecalciferol derivatives and novel intermediates used therefor |
ZA8923B (en) * | 1988-01-20 | 1989-09-27 | Hoffmann La Roche | 16-dehydro-vitamin d3-derivatives |
US4804502A (en) * | 1988-01-20 | 1989-02-14 | Hoffmann-La Roche Inc. | Vitamin D compounds |
US4847012A (en) * | 1988-04-29 | 1989-07-11 | Wisconsin Alumni Research Foundation | Vitamin D related compounds and processes for their preparation |
US5232836A (en) * | 1988-05-04 | 1993-08-03 | Ire-Medgenix S.A. | Vitamin D derivatives: therapeutic applications and applications to assays of metabolites of vitamin D |
FR2631025B1 (fr) * | 1988-05-04 | 1991-04-12 | Ire Medgenix Sa | Nouveaux derives de la vitamine d3 et application aux dosages des metabolites de la vitamine d3 |
GB8904153D0 (en) * | 1989-02-23 | 1989-04-05 | Leo Pharm Prod Ltd | Chemical compounds |
NZ232734A (en) * | 1989-03-09 | 1991-11-26 | Wisconsin Alumni Res Found | 19-nor vitamin d derivatives and pharmaceutical compositions |
AU650751B2 (en) * | 1991-05-28 | 1994-06-30 | Wisconsin Alumni Research Foundation | Novel synthesis of 19-nor vitamin D compounds |
US5086191A (en) * | 1991-05-28 | 1992-02-04 | Wisconsin Alumni Research Foundation | Intermediates for the synthesis of 19-nor vitamin D compounds |
-
1992
- 1992-05-22 AU AU17120/92A patent/AU650751B2/en not_active Expired
- 1992-05-25 CA CA002191993A patent/CA2191993C/en not_active Expired - Lifetime
- 1992-05-25 CA CA002069374A patent/CA2069374C/en not_active Expired - Lifetime
- 1992-05-27 KR KR1019920008983A patent/KR0160784B1/ko not_active IP Right Cessation
- 1992-05-28 AT AT92304837T patent/ATE168996T1/de active
- 1992-05-28 EP EP92304837A patent/EP0516410B1/en not_active Expired - Lifetime
- 1992-05-28 DK DK92304837T patent/DK0516410T3/da active
- 1992-05-28 ES ES92304837T patent/ES2118794T3/es not_active Expired - Lifetime
- 1992-05-28 DE DE69226402T patent/DE69226402T2/de not_active Expired - Lifetime
- 1992-05-28 JP JP4162101A patent/JP2648845B2/ja not_active Expired - Lifetime
- 1992-07-01 IE IE170092A patent/IE921700A1/en not_active IP Right Cessation
- 1992-11-20 US US07/979,482 patent/US5281731A/en not_active Expired - Lifetime
-
1994
- 1994-01-13 US US08/180,702 patent/US5391755A/en not_active Expired - Lifetime
- 1994-04-07 AU AU59325/94A patent/AU659774B2/en not_active Expired
- 1994-10-26 US US08/329,334 patent/US5486636A/en not_active Expired - Lifetime
-
1995
- 1995-05-16 US US08/441,966 patent/US5616759A/en not_active Expired - Lifetime
- 1995-05-16 US US08/441,991 patent/US5581006A/en not_active Expired - Lifetime
- 1995-05-16 US US08/441,878 patent/US5563286A/en not_active Expired - Lifetime
- 1995-05-16 US US08/442,508 patent/US5597932A/en not_active Expired - Lifetime
-
1996
- 1996-08-13 JP JP8231316A patent/JP2926008B2/ja not_active Expired - Lifetime
-
1998
- 1998-03-28 KR KR1019980010907A patent/KR0160937B1/ko not_active IP Right Cessation
- 1998-03-28 KR KR1019980010908A patent/KR0160936B1/ko not_active IP Right Cessation
- 1998-11-12 JP JP33849598A patent/JP3320025B2/ja not_active Expired - Fee Related
-
2001
- 2001-12-05 JP JP2001372049A patent/JP3494637B2/ja not_active Expired - Lifetime
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