ES2020030A6 - Procedimiento de preparacion de nuevos haluros del acido o-(3-amino-2-hidroxipropil)-hidroximico. - Google Patents
Procedimiento de preparacion de nuevos haluros del acido o-(3-amino-2-hidroxipropil)-hidroximico.Info
- Publication number
- ES2020030A6 ES2020030A6 ES8903542A ES8903542A ES2020030A6 ES 2020030 A6 ES2020030 A6 ES 2020030A6 ES 8903542 A ES8903542 A ES 8903542A ES 8903542 A ES8903542 A ES 8903542A ES 2020030 A6 ES2020030 A6 ES 2020030A6
- Authority
- ES
- Spain
- Prior art keywords
- hydrogen
- phenyl
- novel
- hydroximic acid
- same
- 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 - Fee Related
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 150000004820 halides Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 201000009101 diabetic angiopathy Diseases 0.000 abstract 1
- 201000002249 diabetic peripheral angiopathy Diseases 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/08—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
PROCEDIMIENTO DE PREPARACION DE NUEVOS HALUROS DEL ACIDO O-(3-AMINO-2-HIDROXIPROPIL)-HIDROXIMICO. LA INVENCION SE RELACIONA CON UN PROCEDIMIENTO DE PREPARACION DE NUEVOS DERIVADOS DEL ACIDO HIDROXIMIXO DE FORMULA GENERAL (I), EN LA QUE X ES HALOGENO, RSI1 ES HIDROGENO O ALQUILO, RSI2 ES ALQUILO CSI1-5 O CICLOALQUILO, O RSI1 Y RSI2 FORMAN CONJUNTAMENTE CON N UN HETEROANILLO, RSI3 ES HIDROGENO, FENILO, NAFTILO O PIRIDILO, RSI4 Y RSI5 SON HIDROGENO O FENILO, M Y N VARIAN DE 0 A 2, PROCEDIMIENTO CARACTERIZADO PORQUE SE HACE REACCIONAR UNA ALDOXIMA CON UNA N,N-(RSI1,RSI2)-HIDROXI-HALOAMINA O UNA N,N-(RSI1,RSI2)-EPOXIAMINA O EPICLORIDRINA Y UNA RSI1,RSI2-AMINA, PARA DAR LOS COMPUESTOS DE REFERENCIA TRAS TRATAMIENTO EVENTUAL CON PERHALOGENANTES Y POSTERIOR HIDROLISIS. EL PROCEDIMIENTO ES UTIL PARA LA SINTESIS DE LOS COMPUESTOS HALOGENADOS INTERMEDIOS. LOS COMPUESTOS ASI OBTENIDOS, TIENEN IMPORTANTES APLICACIONES TERAPEUTICAS EN LAS ANGIOPATIAS ASOCIADAS A DIABETES MELLITUS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU885405A HU207988B (en) | 1988-10-20 | 1988-10-20 | Process for producing halogenides of o-/3-amino-2-hydroxy-propyl/hydroximic acid and pharmaceutical compositions containing them as active components |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2020030A6 true ES2020030A6 (es) | 1991-07-16 |
Family
ID=10970243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES8903542A Expired - Fee Related ES2020030A6 (es) | 1988-10-20 | 1989-10-20 | Procedimiento de preparacion de nuevos haluros del acido o-(3-amino-2-hidroxipropil)-hidroximico. |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US5147879A (es) |
| EP (1) | EP0417210B1 (es) |
| JP (1) | JPH0819078B2 (es) |
| KR (1) | KR0154117B1 (es) |
| AU (1) | AU620460B2 (es) |
| CA (1) | CA2000830C (es) |
| DE (1) | DE68913737T2 (es) |
| DK (1) | DK175584B1 (es) |
| ES (1) | ES2020030A6 (es) |
| FI (1) | FI93214C (es) |
| GR (1) | GR1002253B (es) |
| HU (1) | HU207988B (es) |
| IE (1) | IE65113B1 (es) |
| IL (1) | IL92000A (es) |
| NO (1) | NO178148C (es) |
| PL (1) | PL164547B1 (es) |
| PT (1) | PT92041B (es) |
| RU (1) | RU2093508C1 (es) |
| UA (1) | UA34412C2 (es) |
| WO (1) | WO1990004584A1 (es) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ285151A (en) * | 1994-05-06 | 1998-09-24 | Biorex Kutato Fejlesztoe Kft | Hydroximic acid derivatives |
| US5665756A (en) * | 1994-08-03 | 1997-09-09 | Hoechst Marion Roussel, Inc. | Aminoalkyloximes useful in the treatment of depression and obsessive compulsive disorders |
| HU9502843D0 (en) * | 1995-09-29 | 1995-11-28 | Livigene Ltd | Pharmaceutical composition |
| HU222994B1 (hu) * | 1995-11-02 | 2004-01-28 | BIOREX Kutató és Fejlesztő Rt. | Hidroxilaminszármazékok és azok alkalmazása sejtek molekuláris chaperon-termelésének fokozására alkalmas gyógyszerkészítmények előállítására |
| AU745987B2 (en) * | 1995-12-22 | 2002-04-11 | N-Gene Research Laboratories Inc. | A cosmetic composition and a method for reducing the ageing processes of skin |
| US6884424B2 (en) | 1995-12-22 | 2005-04-26 | N-Gene Research Laboratories Inc. | Method for treating the pathological lesions of the skin that develop by ultraviolet radiation of the sunlight |
| HUT78139A (hu) * | 1995-12-22 | 2000-11-28 | BIOREX Kutató és Fejlesztő Rt. | Készítmény, különösen a bőr öregedési folyamatainak mérséklésére |
| US6458371B1 (en) | 1995-12-22 | 2002-10-01 | Medgene, Limited | Cosmetic composition and a method for the prevention and/or reduction of the photoaging processes of the skin |
| HUT78138A (hu) | 1995-12-22 | 2000-09-28 | BIOREX Kutató és Fejlesztő Rt | Hidroximsavszármazékot tartalmazó készítmény a növénytermesztés elősegítésére és alkalmazása |
| DE19607960A1 (de) * | 1996-03-01 | 1997-09-04 | Hoechst Schering Agrevo Gmbh | Verfahren zur Herstellung von Ketonoximether durch Boronsäurekupplung |
| GB9613339D0 (en) * | 1996-06-26 | 1996-08-28 | Kritzinger Ann C | Limp bookbinding assembly technique for two books in one pass |
| UA64716C2 (en) * | 1996-08-09 | 2004-03-15 | Pharmaceuticals for therapy or prevention of illnesses connected with dysfunction of vascular endothelial cells | |
| HU220971B1 (hu) * | 1997-04-03 | 2002-07-29 | BIOREX Kutató és Fejlesztő Rt. | Eljárás 0-(3-amino-2-hidroxi-propil)-hidroximsav-halogenidek előállítására |
| HU9701081D0 (en) | 1997-06-23 | 1997-08-28 | Gene Research Lab Inc N | Pharmaceutical composition of antitumoral activity |
| WO2000007580A2 (en) * | 1998-08-03 | 2000-02-17 | N-Gene Kutató Kft. | Pharmaceutical compositions against autoimmune diseases |
| HUP9900475D0 (en) * | 1999-02-26 | 1999-04-28 | Biorex Kutato Fejlesztoe Kft | O-(3-piperidino-2-hydroxy-1-propyl)-hiyroximic acid-halogenid derivative, it's use for treating insulin resistance, and pharmaceutical compositions containing them as active component |
| US6933104B1 (en) | 1999-04-23 | 2005-08-23 | Shiva Biomedical, Llc | Diagnosis and treatment of human kidney diseases |
| HUP0001583A2 (hu) * | 2000-04-18 | 2002-11-28 | BIOREX Kutató és Fejlesztő Rt. | Egy piridin-1-oxid-származék és eljárás annak átalakítására gyógyászati hatású vegyületekké |
| PT1408966E (pt) * | 2001-07-17 | 2008-05-02 | N Gene Res Lab Inc | Combinações farmacêuticas sinergísticas para a prevenção ou tratamento da diabetes |
| HUP0105205A2 (hu) * | 2001-11-29 | 2003-08-28 | BIOREX Kutató és Fejlesztő Rt. | Metformint és egy hidroxilaminszármazékot tartalmazó, gyógyászati készítmény |
| DE60224841T2 (de) * | 2001-12-21 | 2009-01-22 | Rhodia Inc. | Kombinierte stabile kationische und anionische tensidzusammensetzungen |
| JP2005514418A (ja) * | 2002-01-11 | 2005-05-19 | ビオレックス クタトー エス フェイレストェー アールテー. | カルボキサミジン誘導体及び血管疾患の治療におけるそれらの使用 |
| HUP0303584A3 (en) | 2003-10-30 | 2009-12-28 | Cytrx Corp | Use of a hydroximic acid halide derivative in the treatment of neurodegenerative diseases |
| DE10351448A1 (de) * | 2003-11-04 | 2005-06-09 | Bayer Healthcare Ag | Geschmackstoffhaltige Arzneimittelformulierungen mit verbesserten pharmazeutischen Eigenschaften |
| WO2008039514A1 (en) * | 2006-09-26 | 2008-04-03 | Cytrx Corporation | Pharmaceutical compositions and methods for treating diseases associated with neurodegeneration |
| US7763601B2 (en) * | 2006-11-02 | 2010-07-27 | N-Gene Research Laboratories, Inc. | Prevention and treatment of obesity |
| WO2010058779A1 (ja) | 2008-11-18 | 2010-05-27 | 参天製薬株式会社 | ピリジン-3-カルバルデヒド o-(ピペリジン-1-イル-プロピル)-オキシム誘導体を有効成分として含有する網脈絡膜変性疾患の治療剤 |
| HUP1100535A2 (en) | 2011-09-26 | 2013-04-29 | Bracelia Invest Ltd | Pharmaceutical composition for enhancement of stem cell treatment |
| HUP1100534A2 (en) | 2011-09-26 | 2013-04-29 | Balazs Dr Hazay | Pharmaceutical composition for the treatment of muscle atrophy |
| US20210145815A1 (en) | 2017-09-22 | 2021-05-20 | The University Of Adelaide | Methods and products for improving sperm quality |
| KR101995300B1 (ko) | 2018-03-30 | 2019-10-17 | 주식회사 아세아텍 | 다목적 관리기용 작업기 탈부착장치 |
| HUP1800298A1 (hu) | 2018-08-30 | 2020-05-28 | N Gene Res Laboratories Inc | Gyógyszerkombináció béta-receptor blokkolók hatásának módosítására és a mellékhatások csökkentésére |
| CN112174853B (zh) * | 2020-11-03 | 2023-07-25 | 湖南经世新材料有限责任公司 | 一种氨解法制备(z)-n-羟基苯脒的方法 |
| IL303026A (en) | 2020-11-19 | 2023-07-01 | Zevra Denmark As | Processes for preparing arimoclomol citrate and intermediates thereof |
| US20240383853A1 (en) * | 2021-09-28 | 2024-11-21 | Zevra Denmark A/S | Oximes and their use in treatment of gba-related diseases |
| AU2023454616A1 (en) | 2023-07-10 | 2026-01-22 | N-Gene Research Laboratories, Inc. | Increasing telomere length and/or suppressing telomere shortening |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670497C3 (de) * | 1967-06-06 | 1973-12-20 | Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt, Budapest | Isochinohnderivate und Verfahren zu deren Herstellung |
| HU177578B (en) * | 1976-08-27 | 1981-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new 0-/3-amino-2-hydroxy-propyl/-amidoxime derivatives |
| US4187220A (en) * | 1977-08-30 | 1980-02-05 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | New O-(3-amino-2-hydroxy-propyl)-amidoxime derivatives, process for the preparation thereof and pharmaceutical compositions containing same |
| US4308399A (en) * | 1977-08-30 | 1981-12-29 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | O-(3-Amino-2-hydroxy-propyl)-amidoxime derivatives, process for the preparation thereof and pharmaceutical compositions containing same |
| EP0369944A1 (de) * | 1988-11-18 | 1990-05-23 | Ciba-Geigy Ag | Substituierte Oxadiaminobutane |
| FR2639942B1 (fr) * | 1988-12-02 | 1991-03-29 | Sanofi Sa | Ethers oximes de propenone, procede pour leur preparation et compositions pharmaceutiques les contenant |
| HUT54347A (en) * | 1989-01-10 | 1991-02-28 | Chinoin Gyogyszer Es Vegyeszet | Improved process for producing amidoximes |
-
1988
- 1988-10-20 HU HU885405A patent/HU207988B/hu unknown
-
1989
- 1989-10-16 IL IL9200089A patent/IL92000A/en not_active IP Right Cessation
- 1989-10-17 CA CA002000830A patent/CA2000830C/en not_active Expired - Lifetime
- 1989-10-19 KR KR1019900701346A patent/KR0154117B1/ko not_active Expired - Fee Related
- 1989-10-19 AU AU44186/89A patent/AU620460B2/en not_active Expired
- 1989-10-19 GR GR890100669A patent/GR1002253B/el not_active IP Right Cessation
- 1989-10-19 WO PCT/HU1989/000048 patent/WO1990004584A1/en not_active Ceased
- 1989-10-19 IE IE336489A patent/IE65113B1/en not_active IP Right Cessation
- 1989-10-19 RU SU894830570A patent/RU2093508C1/ru active
- 1989-10-19 PT PT92041A patent/PT92041B/pt not_active IP Right Cessation
- 1989-10-19 PL PL89281898A patent/PL164547B1/pl unknown
- 1989-10-19 UA UA4830570A patent/UA34412C2/uk unknown
- 1989-10-19 DE DE68913737T patent/DE68913737T2/de not_active Expired - Lifetime
- 1989-10-19 JP JP1510821A patent/JPH0819078B2/ja not_active Expired - Fee Related
- 1989-10-19 EP EP89911590A patent/EP0417210B1/en not_active Expired - Lifetime
- 1989-10-19 US US07/499,318 patent/US5147879A/en not_active Expired - Lifetime
- 1989-10-20 ES ES8903542A patent/ES2020030A6/es not_active Expired - Fee Related
-
1990
- 1990-06-18 NO NO902703A patent/NO178148C/no unknown
- 1990-06-19 FI FI903075A patent/FI93214C/fi active IP Right Grant
- 1990-06-19 DK DK199001497A patent/DK175584B1/da not_active IP Right Cessation
-
1992
- 1992-07-01 US US07/906,402 patent/US5296606A/en not_active Expired - Lifetime
-
1993
- 1993-06-07 US US08/072,765 patent/US5328906A/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SA6 | Expiration date (snapshot 920101) |
Free format text: 2009-10-20 |
|
| PC1A | Transfer granted | ||
| FD1A | Patent lapsed |
Effective date: 20100616 |