NO178927C - Analogifremgangsmåte for fremstilling av terapeutisk aktive benzimidazoler - Google Patents
Analogifremgangsmåte for fremstilling av terapeutisk aktive benzimidazolerInfo
- Publication number
- NO178927C NO178927C NO912859A NO912859A NO178927C NO 178927 C NO178927 C NO 178927C NO 912859 A NO912859 A NO 912859A NO 912859 A NO912859 A NO 912859A NO 178927 C NO178927 C NO 178927C
- Authority
- NO
- Norway
- Prior art keywords
- preparation
- therapeutically active
- analogous process
- benzimidazoles
- active benzimidazoles
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Toys (AREA)
- Instructional Devices (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4023369A DE4023369A1 (de) | 1990-07-23 | 1990-07-23 | Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4031287A DE4031287A1 (de) | 1990-07-23 | 1990-10-04 | Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4105324A DE4105324A1 (de) | 1990-07-23 | 1991-02-20 | Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO912859D0 NO912859D0 (no) | 1991-07-22 |
| NO912859L NO912859L (no) | 1992-01-24 |
| NO178927B NO178927B (no) | 1996-03-25 |
| NO178927C true NO178927C (no) | 1996-07-03 |
Family
ID=27201487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO912859A NO178927C (no) | 1990-07-23 | 1991-07-22 | Analogifremgangsmåte for fremstilling av terapeutisk aktive benzimidazoler |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0468470B1 (no) |
| JP (1) | JP2539113B2 (no) |
| AT (1) | ATE151766T1 (no) |
| AU (1) | AU640505B2 (no) |
| CA (1) | CA2047496C (no) |
| CS (1) | CS230491A3 (no) |
| DE (1) | DE59108658D1 (no) |
| DK (1) | DK0468470T3 (no) |
| ES (1) | ES2100907T3 (no) |
| FI (1) | FI105811B (no) |
| GR (1) | GR3024027T3 (no) |
| HU (1) | HUT58298A (no) |
| IE (1) | IE912563A1 (no) |
| IL (1) | IL98933A (no) |
| NO (1) | NO178927C (no) |
| NZ (1) | NZ239089A (no) |
| PT (1) | PT98414B (no) |
| RU (1) | RU1836357C (no) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8904174D0 (en) * | 1989-02-23 | 1989-04-05 | British Bio Technology | Compounds |
| NZ232785A (en) * | 1989-03-15 | 1991-03-26 | Janssen Pharmaceutica Nv | 5-(1,2 benzisoxazol-, benzimidazol and benzisothiazol-3- yl)-1h-benzimadazol-2-yl carbamic acid ester derivatives preparatory processes, intermediates and anthelmintic compositions |
| IE70593B1 (en) * | 1989-09-29 | 1996-12-11 | Eisai Co Ltd | Biphenylmethane derivative the use of it and pharmacological compositions containing same |
| SI9210098B (sl) * | 1991-02-06 | 2000-06-30 | Dr. Karl Thomae | Benzimidazoli, zdravila, ki te spojine vsebujejo, in postopek za njihovo pripravo |
| US5602127A (en) * | 1991-02-06 | 1997-02-11 | Karl Thomae Gmbh | (Alkanesultam-1-yl)-benzimidazol-1-yl)-1yl)-methyl-biphenyls useful as angiotensin-II antagonists |
| US5614519A (en) * | 1991-02-06 | 1997-03-25 | Karl Thomae Gmbh | (1-(2,3 or 4-N-morpholinoalkyl)-imidazol-4-yl)-benizimidazol-1-yl-methyl]-biphenyls useful as angiotensin-II antagonists |
| DE4225756A1 (de) * | 1992-01-22 | 1994-03-10 | Thomae Gmbh Dr K | Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE4224133A1 (de) * | 1992-07-22 | 1994-01-27 | Thomae Gmbh Dr K | Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US5594003A (en) * | 1991-02-06 | 1997-01-14 | Dr. Karl Thomae Gmbh | Tetrahydroimidazo[1,2-a]pyridin-2-yl-(benzimidazol-1-yl)-methyl-biphenyls useful as angiotensin-II antagonists |
| DE4224752A1 (de) * | 1992-04-11 | 1994-02-03 | Thomae Gmbh Dr K | Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US5798364A (en) * | 1992-03-26 | 1998-08-25 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Imidazopyridines |
| EP0531874A1 (en) * | 1991-09-10 | 1993-03-17 | Tanabe Seiyaku Co., Ltd. | Imidazopyridine derivatives and process for preparation thereof |
| EP0543263A3 (en) * | 1991-11-16 | 1993-08-25 | Dr. Karl Thomae Gmbh | Benziimidazoles, pharmaceuticals containing them and process for their preparation |
| DE4219534A1 (de) * | 1992-02-19 | 1993-12-16 | Thomae Gmbh Dr K | Substituierte Biphenylylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE4207904A1 (de) * | 1992-03-12 | 1993-09-16 | Thomae Gmbh Dr K | Substituierte benzimidazolylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US5612360A (en) * | 1992-06-03 | 1997-03-18 | Eli Lilly And Company | Angiotensin II antagonists |
| DE4237656A1 (de) * | 1992-06-13 | 1993-12-16 | Merck Patent Gmbh | Benzimidazolderivate |
| GB9218449D0 (en) | 1992-08-29 | 1992-10-14 | Boots Co Plc | Therapeutic agents |
| DE4304455A1 (de) * | 1993-02-15 | 1994-08-18 | Bayer Ag | Heterocyclisch substituierte Phenyl-cyclohexan-carbonsäurederivate |
| DE4408497A1 (de) * | 1994-03-14 | 1995-09-21 | Thomae Gmbh Dr K | Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US5753672A (en) * | 1994-04-19 | 1998-05-19 | Tanabe Seiyaku Co., Ltd. | Imidazopyridine derivatives and process for preparing the same |
| PL318199A1 (en) * | 1994-06-29 | 1997-05-26 | Smithkline Beecham Corp | Antagonists of vitronectin receptors |
| WO1997024334A1 (en) * | 1995-12-28 | 1997-07-10 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| TW453999B (en) | 1997-06-27 | 2001-09-11 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| SE9903028D0 (sv) | 1999-08-27 | 1999-08-27 | Astra Ab | New use |
| DE10314702A1 (de) * | 2003-03-31 | 2004-10-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung von Telmisartan |
| DE602004005488T2 (de) * | 2003-10-16 | 2007-11-29 | Teva Pharmaceutical Industries Ltd. | Verfahren zur herstellung von candesartan cilexetil |
| CN101039917A (zh) * | 2004-10-15 | 2007-09-19 | 特瓦制药工业有限公司 | 制备替米沙坦的方法 |
| US8034782B2 (en) | 2008-07-16 | 2011-10-11 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2008151257A2 (en) | 2007-06-04 | 2008-12-11 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| EP2810951B1 (en) | 2008-06-04 | 2017-03-15 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| AU2010253336A1 (en) | 2009-05-29 | 2011-12-08 | Sumitomo Chemical Company, Limited | Agent for treatment or prevention of diseases associated with activity of neurotrophic factors |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| CN105764916B (zh) | 2013-06-05 | 2021-05-18 | 博士医疗爱尔兰有限公司 | 鸟苷酸环化酶c的超纯激动剂、制备和使用所述激动剂的方法 |
| PL3010503T3 (pl) * | 2013-06-21 | 2020-08-24 | Zenith Epigenetics Ltd. | Nowe bicykliczne inhibitory bromodomen |
| WO2015004533A2 (en) | 2013-06-21 | 2015-01-15 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
| EP3027604B1 (en) | 2013-07-31 | 2019-02-20 | Zenith Epigenetics Ltd. | Novel quinazolinones as bromodomain inhibitors |
| EP3177604A1 (en) * | 2014-08-05 | 2017-06-14 | Bristol-Myers Squibb Company | Heterocyclic kinase inhibitors |
| US10710992B2 (en) | 2014-12-01 | 2020-07-14 | Zenith Epigenetics Ltd. | Substituted pyridinones as bromodomain inhibitors |
| CN107207474B (zh) | 2014-12-11 | 2021-05-07 | 恒翼生物医药科技(上海)有限公司 | 被取代的杂环作为溴结构域抑制剂 |
| US10231953B2 (en) | 2014-12-17 | 2019-03-19 | Zenith Epigenetics Ltd. | Inhibitors of bromodomains |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820843A (en) * | 1987-05-22 | 1989-04-11 | E. I. Du Pont De Nemours And Company | Tetrazole intermediates to antihypertensive compounds |
| US4880804A (en) * | 1988-01-07 | 1989-11-14 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking benzimidazoles |
| CA2016710A1 (en) * | 1989-05-15 | 1990-11-15 | Prasun K. Chakravarty | Substituted benzimidazoles as angiotensin ii antagonists |
| AU645022B2 (en) * | 1989-06-30 | 1994-01-06 | E.I. Du Pont De Nemours And Company | Fused-ring aryl substituted imidazoles |
| IE70593B1 (en) * | 1989-09-29 | 1996-12-11 | Eisai Co Ltd | Biphenylmethane derivative the use of it and pharmacological compositions containing same |
| IL95975A (en) * | 1989-10-24 | 1997-06-10 | Takeda Chemical Industries Ltd | N-benzyl- 2-alkylbenzimidazole derivatives, their production and pharmaceutical compositions containing them |
| IL96019A0 (en) * | 1989-10-31 | 1991-07-18 | Fujisawa Pharmaceutical Co | Imidazole derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
-
1991
- 1991-07-04 RU SU915001010A patent/RU1836357C/ru active
- 1991-07-22 AT AT91112404T patent/ATE151766T1/de not_active IP Right Cessation
- 1991-07-22 NO NO912859A patent/NO178927C/no not_active IP Right Cessation
- 1991-07-22 ES ES91112404T patent/ES2100907T3/es not_active Expired - Lifetime
- 1991-07-22 DE DE59108658T patent/DE59108658D1/de not_active Expired - Lifetime
- 1991-07-22 FI FI913503A patent/FI105811B/fi not_active IP Right Cessation
- 1991-07-22 DK DK91112404.8T patent/DK0468470T3/da active
- 1991-07-22 CA CA002047496A patent/CA2047496C/en not_active Expired - Lifetime
- 1991-07-22 HU HU912456A patent/HUT58298A/hu unknown
- 1991-07-22 JP JP3181033A patent/JP2539113B2/ja not_active Expired - Lifetime
- 1991-07-22 EP EP91112404A patent/EP0468470B1/de not_active Expired - Lifetime
- 1991-07-22 IE IE256391A patent/IE912563A1/en not_active IP Right Cessation
- 1991-07-22 PT PT98414A patent/PT98414B/pt not_active IP Right Cessation
- 1991-07-23 IL IL9893391A patent/IL98933A/en not_active IP Right Cessation
- 1991-07-23 AU AU81227/91A patent/AU640505B2/en not_active Expired
- 1991-07-23 NZ NZ23908991A patent/NZ239089A/en not_active IP Right Cessation
- 1991-07-23 CS CS912304A patent/CS230491A3/cs unknown
-
1997
- 1997-07-09 GR GR970401682T patent/GR3024027T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE912563A1 (en) | 1992-01-29 |
| AU640505B2 (en) | 1993-08-26 |
| FI105811B (fi) | 2000-10-13 |
| ES2100907T3 (es) | 1997-07-01 |
| AU8122791A (en) | 1992-01-30 |
| EP0468470B1 (de) | 1997-04-16 |
| FI913503A7 (fi) | 1992-01-24 |
| CA2047496C (en) | 2001-10-23 |
| NO178927B (no) | 1996-03-25 |
| DE59108658D1 (de) | 1997-05-22 |
| RU1836357C (ru) | 1993-08-23 |
| PT98414A (pt) | 1992-05-29 |
| IL98933A (en) | 1995-12-31 |
| CA2047496A1 (en) | 1992-01-24 |
| IL98933A0 (en) | 1992-07-15 |
| HUT58298A (en) | 1992-02-28 |
| EP0468470A1 (de) | 1992-01-29 |
| FI913503A0 (fi) | 1991-07-22 |
| PT98414B (pt) | 1999-01-29 |
| NZ239089A (en) | 1994-07-26 |
| NO912859L (no) | 1992-01-24 |
| JP2539113B2 (ja) | 1996-10-02 |
| HU912456D0 (en) | 1991-12-30 |
| ATE151766T1 (de) | 1997-05-15 |
| CS230491A3 (en) | 1992-02-19 |
| DK0468470T3 (da) | 1997-09-22 |
| GR3024027T3 (en) | 1997-10-31 |
| NO912859D0 (no) | 1991-07-22 |
| JPH04253966A (ja) | 1992-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |