FI91528B - Optiskt aktiva alkylarylketaler och förfarande för framställning av dessa - Google Patents
Optiskt aktiva alkylarylketaler och förfarande för framställning av dessa Download PDFInfo
- Publication number
- FI91528B FI91528B FI851318A FI851318A FI91528B FI 91528 B FI91528 B FI 91528B FI 851318 A FI851318 A FI 851318A FI 851318 A FI851318 A FI 851318A FI 91528 B FI91528 B FI 91528B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- methoxy
- naphthyl
- group
- ketal
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
-
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/32—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 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (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)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Steroid Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Claims (5)
1. Optiskt aktiva alkylarylketaler med formeln (I) R -CO H ς 1 \ * -:/ c-c7 h/L /“Λ Ar ' ^^CH-R 10 x väri Ar är 6-metoxi-2-naftyl eller 6-metoxi-5-brom-2-naf- tyl, R är CM-alkyl, Rt och R2 betecknar hydroxi eller en £ grupp 0"M+, OR3 eller-Nc^r4, i vilka M+ är en alkalimetall-katjon och R3, R4 och R3 oberoende av varandra betecknar 15 lägre alkyl, X är klor, brom, jod, hydroxi, acyloxi, al-kylsulfonyloxi eller arylsulfonyloxi, och de med asterisk indikerade C-atomerna har samtidigt antingen R- eller S-konf iguration.
2. Förfarande för framställning av optiskt aktiva 20 alkylarylketaler med formeln (I) R -CO H 1 \ * / C-c7 H / i C0-R2 -· 25 \ (I) Ar CH-R X väri Ar är 6-metoxi-2-naftyl eller 6-metoxi-5-brom-2-naf- tyl, R är CM-alkyl, R, och R2 betecknar hydroxi eller en R 30 grupp 0"M+, OR3 eller-Nc^r4 , i vilka M+ är en alkalimetall-katjon och R3, R4 och R5 oberoende av varandra betecknar lägre alkyl, X är klor, brom, jod, hydroxi, acyloxi, al-kylsulfonyloxi eller arylsulfonyloxi, och de med asterisk indikerade C-atomerna har samtidigt antingen R- eller S-35 konfiguration, kännetecknat därav, att L(+)- 91 528 36 eller D(-)-vinsyra eller ett derivat därav med formeln R -CO-CH-CH-CO-R»
1. I ^ OH OH 5 väri R, och R2 betecknar sanuna som ovan, omsätts (a) med en keton med formeln Ar-C-CH-R II I
10. X (II) eller (b) med en ketal med formeln
15 R8°\ /0R9 /\ Ar CjH-R (III) X 20 väri Ar, R och X betecknar samma som ovan och Rg och R, betecknar vartdera skilt för sig CM-alkyl eller tillsam-mans C^-alkylen, sä att de bildar en 5- eller 6-ledad ring ' 25 med gruppen O-c-O, och om sä önskas omvandlas en ketal med formeln I, väri R, och R2 betecknar en grupp 0R3, med hjälp av en stark bas till en ketal med formeln I, väri R, och/eller R2 är en grupp 0*M+, vari M+ betecknar samma som ovan, och om sk 30 önskas, omvandlas sistnämnda ketal med hjälp av en syra till en ketal med formeln I, väri R! och/eller R2 är OH, eller om sk önskas, omvandlas en ketal med formeln I, vari R, och R2 betecknar en grupp OR3, medelst aminbehandling till en ketal med formeln I, vari Rj och/eller R2 betecknar 3 5 en grupp NR^, vari R4 och R5 betecknar samma som ovan. II
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI911886A FI92688C (sv) | 1984-04-06 | 1991-04-18 | Förfarande för framställning av optiskt aktiva -arylalkankarboxylsyror |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT720484 | 1984-04-06 | ||
IT8407204A IT1214809B (it) | 1984-04-06 | 1984-04-06 | Intermedi utili per la sintesi di acidi carbossilici. |
IT07206/84A IT1199447B (it) | 1984-08-06 | 1984-08-06 | Intermedi utili per la sintesi di acidi carbossilici |
IT720784 | 1984-08-06 | ||
IT720684 | 1984-08-06 | ||
IT8407207A IT1207420B (it) | 1984-08-06 | 1984-08-06 | Acidi carbossilici. procedimento per la preparazione di |
Publications (4)
Publication Number | Publication Date |
---|---|
FI851318A0 FI851318A0 (sv) | 1985-04-02 |
FI851318L FI851318L (sv) | 1985-10-07 |
FI91528B true FI91528B (sv) | 1994-03-31 |
FI91528C FI91528C (sv) | 1994-07-11 |
Family
ID=27272674
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI851318A FI91528C (sv) | 1984-04-06 | 1985-04-02 | Optiskt aktiva alkylarylketaler och förfarande för framställning av dessa |
FI851317A FI91393C (sv) | 1984-04-06 | 1985-04-02 | Enantioselektivt förfarande för framställning av optiskt aktiva -arylalkankarboxylsyror |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI851317A FI91393C (sv) | 1984-04-06 | 1985-04-02 | Enantioselektivt förfarande för framställning av optiskt aktiva -arylalkankarboxylsyror |
Country Status (18)
Country | Link |
---|---|
US (4) | US4697036A (sv) |
EP (2) | EP0158255B1 (sv) |
JP (7) | JPH0784457B2 (sv) |
KR (2) | KR920007223B1 (sv) |
AT (2) | ATE35810T1 (sv) |
AU (2) | AU577362B2 (sv) |
CA (3) | CA1281029C (sv) |
DE (2) | DE3563848D1 (sv) |
DK (2) | DK166272C (sv) |
ES (5) | ES8701748A1 (sv) |
FI (2) | FI91528C (sv) |
GR (2) | GR850846B (sv) |
HU (2) | HU198439B (sv) |
IE (2) | IE58032B1 (sv) |
MX (1) | MX169453B (sv) |
NO (2) | NO169385C (sv) |
PT (2) | PT80243B (sv) |
YU (2) | YU43942B (sv) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE35810T1 (de) * | 1984-04-06 | 1988-08-15 | Zambon Spa | Verfahren zur herstellung von optisch aktiven alpha-arylalkansaeuren und ihre zwischenprodukte. |
IT1201443B (it) * | 1985-07-31 | 1989-02-02 | Zambon Spa | Intermedi per la sintesi di acidi carbossilici |
IT1190398B (it) * | 1985-10-04 | 1988-02-16 | Zambon Spa | Processo per la preparazione di alfa aloalchil-aril-chetoni otticamente attivi |
IT1190399B (it) * | 1985-10-04 | 1988-02-16 | Zambon Spa | Processo per la preparazione di composti carbonilici otticamente attivi |
IT1190436B (it) * | 1985-12-13 | 1988-02-16 | Zambon Spa | Processo stereoselettivo per la preparazione di composti carbonilici alfa,beta-disostituiti otticamente attivi |
IT1197800B (it) * | 1986-08-01 | 1988-12-06 | Zambon Spa | Processo per la sintesi di acidi carbossilici |
IT1198234B (it) * | 1986-12-23 | 1988-12-21 | Zambon Spa | Processo stereoconvergente per la preparazione di acidi carbossilici otticamente attivi |
US4912248A (en) * | 1987-05-18 | 1990-03-27 | The Procter & Gamble Company | Novel anti-inflammatory agents, pharmaceutical compositions and methods for reducing inflammation |
IT1227537B (it) * | 1987-07-28 | 1991-04-12 | Zambon Spa | Processo per la preparazione dell'acido s(+)-2-(6-metossi-2-naftil)- propionico |
CA2016887A1 (en) * | 1989-05-16 | 1990-11-16 | Henrich H. Paradies | Process for preparing optically active 2-aryl-alkanoic acids, in particular 2-aryl propionic acids |
US5266723A (en) * | 1989-05-16 | 1993-11-30 | Medice, Ltd., Chem.-Pharm. Fabrik Putter Gmbh & Co. Kg | Process for the preparation of optically active 2-aryl-alkanoic acids, especially 2-aryl-propionic acids |
FI94339C (sv) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Förfarande för framställning av farmaceutiskt användbar /R-(R*,R*)/-2-(4-fluorfenyl)- , -dihydroxi-5-(1-metyletyl)-3-fenyl-4-/(fenylamino)karbonyl/-1H-pyrrol-1-heptansyra och farmaceutiskt användbara salter därav |
US6194140B1 (en) | 1990-04-04 | 2001-02-27 | Chiron Corporation | HCV NS3 protein fragments having helicase activity and improved solubility |
IT1251958B (it) * | 1991-10-18 | 1995-05-27 | Zambon Spa | Processo per la dealogenazione di derivati del naftalene |
US5434302A (en) * | 1994-02-18 | 1995-07-18 | Paradies; H. Henrich | Method for the preparation of optically active 2-aryl alkyl aldehydes and formation of 2-aryl-alkanoic acids therefrom |
US5756851A (en) * | 1996-10-21 | 1998-05-26 | Albemarle Corporation | Production of nabumetone or precursors thereof |
US6080888A (en) * | 1997-01-08 | 2000-06-27 | Albemarle Corporation | Preparation of olefinic compounds and carboxylic derivatives thereof |
US5792886A (en) * | 1997-01-08 | 1998-08-11 | Albemarle Corporation | Production of racemic 2-(6-methoxy-2-naphthyl) propionic acid of precursors thereof |
US6096920A (en) * | 1997-01-08 | 2000-08-01 | Albemarle Corporation | Preparation of carboxylic compounds and their derivatives |
US5942527A (en) * | 1997-08-27 | 1999-08-24 | K & K Biosciences, Inc. | Hydrazones, hydrazines, semicarbazones and thiosemicarbazones derived from pyridyl ketones as anticonvulsant drugs and excitatory amino acid antagonists |
CA2376400A1 (en) | 1999-06-08 | 2000-12-14 | University Of Iowa Research Foundation | Compounds and methods to enhance raav transduction |
IT1315212B1 (it) * | 1999-07-26 | 2003-02-03 | Consiglio Nazionale Ricerche | Impiego di ortoesteri per la sintesi di acidi chirali in processi diesterificazione irreversibili biocatalizzati. |
AU2004227358B8 (en) | 2003-03-31 | 2009-12-10 | Targeted Genetics Corporation | Compounds and methods to enhance rAAV transduction |
JP4511809B2 (ja) * | 2003-06-19 | 2010-07-28 | 川口薬品株式会社 | ムスコンのアセタール付加体、その調製方法、並びに(±)−ムスコンの光学分割方法 |
GB0501237D0 (en) * | 2005-01-21 | 2005-03-02 | Givaudan Sa | Organic compounds |
DE102010063609A1 (de) | 2010-12-20 | 2012-06-21 | Awd.Pharma Gmbh & Co. Kg | Neue Multikomponentenkristalle aus ([2-Amino-6-(4-fluoro-benzylamino)-pyridin-3yl)-carbamidsäureethylester und einer Arylpropionsäure |
WO2017139381A1 (en) | 2016-02-08 | 2017-08-17 | University Of Iowa Research Foundation | Methods to produce chimeric adeno-associated virus/bocavirus parvovirus |
CA3198936A1 (en) | 2016-03-07 | 2017-09-14 | University Of Iowa Research Foundation | Aav-mediated expression using a synthetic promoter and enhancer |
US11142775B2 (en) | 2017-01-13 | 2021-10-12 | University Of Iowa Research Foundation | Bocaparvovirus small noncoding RNA and uses thereof |
CN110229069A (zh) * | 2019-07-16 | 2019-09-13 | 重庆医药高等专科学校 | 三甲基苯基三溴化铵的制备方法及萘普生生产中三甲基苯基三溴化铵的回收利用方法 |
CN114644554A (zh) * | 2020-12-21 | 2022-06-21 | 上海医药工业研究院 | (s)-氟比洛芬的制备方法及其中间体 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
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US2249519A (en) * | 1940-10-09 | 1941-07-15 | Eastman Kodak Co | Yarn conditioning process and compositions therefor |
US3247240A (en) * | 1962-01-05 | 1966-04-19 | Geigy Ag J R | Process for the preparation of carbonyl compounds containing a hindered phenol group |
SE367181B (sv) * | 1969-05-14 | 1974-05-20 | Takeda Chemical Industries Ltd | |
US4107439A (en) * | 1976-06-16 | 1978-08-15 | The Upjohn Company | Process for preparing arylalkanoic acid derivatives |
EP0034781B1 (de) * | 1980-02-21 | 1984-02-01 | BASF Aktiengesellschaft | Verfahren zur Herstellung von duktilen Verbundwerkstoffen |
IE50898B1 (en) * | 1980-02-26 | 1986-08-06 | Blaschim Spa | Process for preparing esters of 2-(6'-methoxy-2'-naphthyl)-propionic acid via rearrangement of new ketals of 2-halo-1-(6'-methoxy-2'-naphthyl)-propan-1-one |
JPS5810525A (ja) * | 1981-06-15 | 1983-01-21 | Sagami Chem Res Center | 光学活性な1−芳香族基置換−1−アルカノン類の製造方法 |
IT1190741B (it) * | 1982-03-22 | 1988-02-24 | Blaschim Spa | Procedimento per preparare esteri dell'acido 2-(6'-metossi-2'-naftil)-propionico |
US4623736A (en) * | 1982-07-09 | 1986-11-18 | The Upjohn Company | Arylalkanoic acid process improvement |
EP0101124B1 (en) * | 1982-08-06 | 1986-01-29 | ZAMBON S.p.A. | Process for preparing alpha arylalkanoic acids |
JPS6071271A (ja) * | 1983-09-29 | 1985-04-23 | Fuji Xerox Co Ltd | 感熱記録装置 |
ATE35810T1 (de) * | 1984-04-06 | 1988-08-15 | Zambon Spa | Verfahren zur herstellung von optisch aktiven alpha-arylalkansaeuren und ihre zwischenprodukte. |
JPH0585102A (ja) * | 1991-09-24 | 1993-04-06 | Nissan Motor Co Ltd | トルクチユーブ装置 |
-
1985
- 1985-04-01 AT AT85103906T patent/ATE35810T1/de not_active IP Right Cessation
- 1985-04-01 AT AT85103907T patent/ATE39691T1/de active
- 1985-04-01 DE DE8585103906T patent/DE3563848D1/de not_active Expired
- 1985-04-01 DE DE8585103907T patent/DE3567209D1/de not_active Expired
- 1985-04-01 EP EP85103907A patent/EP0158255B1/en not_active Expired
- 1985-04-01 EP EP85103906A patent/EP0158913B1/en not_active Expired
- 1985-04-02 DK DK149885A patent/DK166272C/da not_active Application Discontinuation
- 1985-04-02 DK DK149785A patent/DK166876B1/da not_active IP Right Cessation
- 1985-04-02 NO NO851349A patent/NO169385C/no not_active IP Right Cessation
- 1985-04-02 FI FI851318A patent/FI91528C/sv not_active IP Right Cessation
- 1985-04-02 FI FI851317A patent/FI91393C/sv not_active IP Right Cessation
- 1985-04-02 NO NO851350A patent/NO170685C/no unknown
- 1985-04-03 HU HU851281A patent/HU198439B/hu not_active IP Right Cessation
- 1985-04-03 HU HU851282A patent/HU197711B/hu unknown
- 1985-04-03 ES ES542641A patent/ES8701748A1/es not_active Expired
- 1985-04-03 ES ES542640A patent/ES8802295A1/es not_active Expired
- 1985-04-04 PT PT80243A patent/PT80243B/pt not_active IP Right Cessation
- 1985-04-04 IE IE87985A patent/IE58032B1/en not_active IP Right Cessation
- 1985-04-04 IE IE88085A patent/IE58258B1/en not_active IP Right Cessation
- 1985-04-04 AU AU40840/85A patent/AU577362B2/en not_active Ceased
- 1985-04-04 GR GR850846A patent/GR850846B/el unknown
- 1985-04-04 CA CA000478586A patent/CA1281029C/en not_active Expired - Fee Related
- 1985-04-04 PT PT80244A patent/PT80244B/pt not_active IP Right Cessation
- 1985-04-04 CA CA000478585A patent/CA1282410C/en not_active Expired - Fee Related
- 1985-04-04 AU AU40842/85A patent/AU575927B2/en not_active Ceased
- 1985-04-04 GR GR850847A patent/GR850847B/el unknown
- 1985-04-05 US US06/720,380 patent/US4697036A/en not_active Expired - Lifetime
- 1985-04-05 JP JP60071271A patent/JPH0784457B2/ja not_active Expired - Lifetime
- 1985-04-05 YU YU570/85A patent/YU43942B/xx unknown
- 1985-04-05 US US06/720,379 patent/US4734507A/en not_active Expired - Lifetime
- 1985-04-06 KR KR1019850002311A patent/KR920007223B1/ko not_active IP Right Cessation
- 1985-04-06 KR KR1019850002312A patent/KR920010927B1/ko not_active IP Right Cessation
- 1985-04-06 JP JP60073388A patent/JPH0791214B2/ja not_active Expired - Lifetime
- 1985-04-08 YU YU579/85A patent/YU43686B/xx unknown
- 1985-04-08 MX MX005727A patent/MX169453B/es unknown
-
1986
- 1986-01-31 ES ES551476A patent/ES8705415A1/es not_active Expired
- 1986-05-14 ES ES554936A patent/ES8706661A1/es not_active Expired
- 1986-08-01 ES ES557037A patent/ES8707490A1/es not_active Expired
-
1987
- 1987-08-05 US US07/082,196 patent/US4888433A/en not_active Expired - Lifetime
- 1987-12-17 US US07/134,197 patent/US4855464A/en not_active Expired - Lifetime
-
1989
- 1989-05-02 CA CA000598530A patent/CA1320495C/en not_active Expired - Fee Related
-
1993
- 1993-03-22 JP JP5085104A patent/JPH07107018B2/ja not_active Expired - Fee Related
- 1993-03-22 JP JP5085103A patent/JPH06100498A/ja active Pending
- 1993-03-22 JP JP5085102A patent/JPH0776193B2/ja not_active Expired - Lifetime
-
1995
- 1995-03-06 JP JP7045381A patent/JP2700024B2/ja not_active Expired - Lifetime
- 1995-03-06 JP JP7045380A patent/JP2700023B2/ja not_active Expired - Fee Related
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