ES8801280A1 - Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinas - Google Patents
Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinasInfo
- Publication number
- ES8801280A1 ES8801280A1 ES555528A ES555528A ES8801280A1 ES 8801280 A1 ES8801280 A1 ES 8801280A1 ES 555528 A ES555528 A ES 555528A ES 555528 A ES555528 A ES 555528A ES 8801280 A1 ES8801280 A1 ES 8801280A1
- Authority
- ES
- Spain
- Prior art keywords
- lower alkyl
- hydroxy
- mono
- amino
- acylamino
- 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
Links
- 150000003222 pyridines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
Abstract
PROCEDIMIENTO PARA LA OBTENCION DE BENZO(PIRANO Y TIOPIRANO)-PIRIDINAS, DE FORMULA GENERAL (I), Y DE SUS SALES FARMACEUTICAMENTE ACEPTABLES. CONSISTE EN REDUCIR UN COMPUESTO DE FORMULA GENERAL (II) CON UN AGENTE REDUCTOR DE HIDROGENACION SENCILLO O COMPLEJO, EN CASO DADO EN PRESENCIA DE UN ACIDO LEWIS. LA REDUCCION SE LLEVA A EFECTO BAJO PROTECCION INTERMEDIA DE LOS GRUPOS FUNCIONALES CAPACES DE REACCION, CUYA REACTIVIDAD PUDIERA REPERCUTIR DE MANERA PERTURBADORA. EL COMPUESTO DE FORMULA GENERAL (I) OBTENIDO SE AISLA DESPUES DE LA CORRESPONDIENTE DISOCIACION DE LOS GRUPOS PROTECTORES. DE APLICACION COMO MEDIOS NEUROLEPTICOS PARA EL TRATAMIENTO DE ESTADOS PSICOTICOS O COMO MEDIOS ANTIDEPRESIVOS PARA EL TRATAMIENTO DE DEPRESIONES.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60903784A | 1984-05-10 | 1984-05-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES555528A0 ES555528A0 (es) | 1988-01-01 |
| ES8801280A1 true ES8801280A1 (es) | 1988-01-01 |
Family
ID=24439108
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES542929A Expired ES8706687A1 (es) | 1984-05-10 | 1985-05-08 | Procedimiento para la obtencion de benzo-(pirano y tiopira- no)-piridinas |
| ES555529A Expired ES8801281A1 (es) | 1984-05-10 | 1986-05-30 | Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinas |
| ES555530A Expired ES8801282A1 (es) | 1984-05-10 | 1986-05-30 | Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinas |
| ES555528A Expired ES8801280A1 (es) | 1984-05-10 | 1986-05-30 | Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinas |
| ES555527A Expired ES8801279A1 (es) | 1984-05-10 | 1986-05-30 | Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinas |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES542929A Expired ES8706687A1 (es) | 1984-05-10 | 1985-05-08 | Procedimiento para la obtencion de benzo-(pirano y tiopira- no)-piridinas |
| ES555529A Expired ES8801281A1 (es) | 1984-05-10 | 1986-05-30 | Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinas |
| ES555530A Expired ES8801282A1 (es) | 1984-05-10 | 1986-05-30 | Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinas |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES555527A Expired ES8801279A1 (es) | 1984-05-10 | 1986-05-30 | Procedimiento para la obtencion de benzo-(pirano y tiopirano)-piridinas |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4604397A (es) |
| EP (1) | EP0161218B1 (es) |
| JP (1) | JPS60243090A (es) |
| AR (1) | AR243526A1 (es) |
| AT (1) | ATE64735T1 (es) |
| AU (1) | AU592308B2 (es) |
| CA (1) | CA1298582C (es) |
| DD (1) | DD235872A5 (es) |
| DE (1) | DE3583307D1 (es) |
| DK (1) | DK168571B1 (es) |
| ES (5) | ES8706687A1 (es) |
| FI (1) | FI83652C (es) |
| GR (1) | GR851116B (es) |
| HU (1) | HU199476B (es) |
| IE (1) | IE57978B1 (es) |
| IL (1) | IL75135A (es) |
| NO (1) | NO162860C (es) |
| NZ (1) | NZ212031A (es) |
| PT (1) | PT80415B (es) |
| ZA (1) | ZA853507B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8426584D0 (en) * | 1984-10-19 | 1984-11-28 | Beecham Group Plc | Compounds |
| US4666916A (en) * | 1985-11-08 | 1987-05-19 | Ciba-Geigy Corporation | Hexahydro-(1)-benzo-(pyrano and thiopyrano) (4,3-C)pyridines, useful as serotin-2 blocking agents |
| US4792548A (en) * | 1986-05-21 | 1988-12-20 | Warner-Lambert Company | Trans-benzopyran-(4,3-b)-1,4-oxazine derivatives, intermediates and pharmaceutical use |
| US4801605A (en) * | 1986-08-29 | 1989-01-31 | Ciba-Geigy Corporation | 3-amino-dihydro-[1]-benzopyrans and benzothiopyrans |
| FR2619112B1 (fr) * | 1987-08-07 | 1989-11-17 | Synthelabo | Derives de (piperidinyl-4)methyl-2 benzo(b)furo(2,3-c) pyridines, leur preparation et leur application en therapeutique |
| US4992465A (en) * | 1988-09-27 | 1991-02-12 | Ciba-Geigy Corporation | 3-amino-dihydro-(1)-benzopyrans |
| US5962463A (en) * | 1992-10-09 | 1999-10-05 | Massachusetts Institute Of Technology | Methods of stimulating non-amyloidogenic processing of the amyloid precursor protein |
| FR2721027B1 (fr) | 1994-06-08 | 1996-07-19 | Adir | Nouveaux dérivés tétracycliques de la 1,4-oxazine, leur procédé de préparation et les compositions pharmaceutiques les contenant. |
| FR2741074B1 (fr) | 1995-11-09 | 1997-12-19 | Adir | Nouveaux composes tetracycliques de la 1,4-oxazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6342533B1 (en) * | 1998-12-01 | 2002-01-29 | Sepracor, Inc. | Derivatives of (−)-venlafaxine and methods of preparing and using the same |
| DE60039132D1 (de) * | 1999-04-06 | 2008-07-17 | Sepracor Inc | O-Desmethylvenlafaxin-Succinat |
| WO2005032485A2 (en) * | 2003-10-03 | 2005-04-14 | Psychogenics, Inc. | Compounds and methods for the treatment of attention-deficit hyperactivity disorder |
| AU2006265008A1 (en) * | 2005-07-06 | 2007-01-11 | Sepracor Inc. | Combinations of eszopiclone and O-desmethylvenlafaxine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders |
| BRPI1003506B1 (pt) | 2010-09-24 | 2019-12-03 | Ache Int Bvi Ltd | composto alquil-piperazino-fenil-4(3h)quinazolinonas e uso do composto alquil-piperazino-fenil-4(3h)quinazolinonas associado aos receptores serotoninérgicos 5-ht1a e 5-ht2a |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143819A (es) * | 1965-09-27 | |||
| US3514464A (en) * | 1967-05-29 | 1970-05-26 | Little Inc A | 5-oxo-1,2,3,4-tetrahydro-5h-(1)benzopyrano(3,4-c)pyridines |
| US3689497A (en) * | 1971-03-09 | 1972-09-05 | Warner Lambert Co | Substituted benzopyrano (3,4-b) pyridines and process for their preparation |
| US3915996A (en) * | 1972-10-16 | 1975-10-28 | Abbott Lab | Process for making benzopyrans |
| US4025630A (en) * | 1973-09-19 | 1977-05-24 | Abbott Laboratories | Anesthesia methods using benzopyrans and esters thereof as pre-anesthesia medication |
| US4292316A (en) * | 1978-10-02 | 1981-09-29 | Abbott Laboratories | Antiglaucoma agents |
| US4210758A (en) * | 1979-03-21 | 1980-07-01 | Warner-Lambert Company | 1,5-Dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamides |
| US4198511A (en) * | 1979-03-21 | 1980-04-15 | Warner-Lambert Company | 1,5-Dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-3-carboxamides and process thereof |
| JPS5746903A (en) * | 1980-09-05 | 1982-03-17 | Mitsubishi Chem Ind Ltd | Agricultural and gardening fungicide |
| NL8005754A (nl) * | 1980-10-18 | 1982-05-17 | Akzo Nv | Benzo 4,5 pyrano 2,3-c pyrrool derivaten. |
| US4420480A (en) * | 1981-11-20 | 1983-12-13 | Merck & Co., Inc. | Hexahydronaphth[1,2-b]-1,4-oxazines |
| US4540691A (en) * | 1984-04-13 | 1985-09-10 | Nelson Research & Development Co. | Dopamine agonists and use thereof |
| US4666916A (en) * | 1985-11-08 | 1987-05-19 | Ciba-Geigy Corporation | Hexahydro-(1)-benzo-(pyrano and thiopyrano) (4,3-C)pyridines, useful as serotin-2 blocking agents |
-
1985
- 1985-05-06 DE DE8585810208T patent/DE3583307D1/de not_active Expired - Lifetime
- 1985-05-06 AT AT85810208T patent/ATE64735T1/de not_active IP Right Cessation
- 1985-05-06 EP EP85810208A patent/EP0161218B1/de not_active Expired - Lifetime
- 1985-05-07 DD DD85276081A patent/DD235872A5/de not_active IP Right Cessation
- 1985-05-08 IL IL75135A patent/IL75135A/xx unknown
- 1985-05-08 CA CA000481003A patent/CA1298582C/en not_active Expired - Lifetime
- 1985-05-08 PT PT80415A patent/PT80415B/pt not_active IP Right Cessation
- 1985-05-08 ES ES542929A patent/ES8706687A1/es not_active Expired
- 1985-05-08 FI FI851802A patent/FI83652C/fi not_active IP Right Cessation
- 1985-05-08 GR GR851116A patent/GR851116B/el unknown
- 1985-05-09 AU AU42248/85A patent/AU592308B2/en not_active Ceased
- 1985-05-09 HU HU851751A patent/HU199476B/hu not_active IP Right Cessation
- 1985-05-09 NZ NZ212031A patent/NZ212031A/xx unknown
- 1985-05-09 JP JP60096820A patent/JPS60243090A/ja active Granted
- 1985-05-09 DK DK205285A patent/DK168571B1/da not_active IP Right Cessation
- 1985-05-09 IE IE1155/85A patent/IE57978B1/en not_active IP Right Cessation
- 1985-05-09 NO NO851846A patent/NO162860C/no unknown
- 1985-05-09 ZA ZA853507A patent/ZA853507B/xx unknown
- 1985-05-10 AR AR85300343A patent/AR243526A1/es active
- 1985-09-03 US US06/771,934 patent/US4604397A/en not_active Expired - Lifetime
-
1986
- 1986-05-30 ES ES555529A patent/ES8801281A1/es not_active Expired
- 1986-05-30 ES ES555530A patent/ES8801282A1/es not_active Expired
- 1986-05-30 ES ES555528A patent/ES8801280A1/es not_active Expired
- 1986-05-30 ES ES555527A patent/ES8801279A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19970519 |