NO992898L - Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler - Google Patents
Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midlerInfo
- Publication number
- NO992898L NO992898L NO992898A NO992898A NO992898L NO 992898 L NO992898 L NO 992898L NO 992898 A NO992898 A NO 992898A NO 992898 A NO992898 A NO 992898A NO 992898 L NO992898 L NO 992898L
- Authority
- NO
- Norway
- Prior art keywords
- nil
- unsubstituted
- saturated
- substituted
- alkyl
- Prior art date
Links
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract 4
- 230000003288 anthiarrhythmic effect Effects 0.000 title abstract 2
- 235000013877 carbamide Nutrition 0.000 title abstract 2
- 150000003672 ureas Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229920006395 saturated elastomer Polymers 0.000 abstract 4
- 125000004442 acylamino group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- -1 CH3SO2NH Chemical group 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000004404 heteroalkyl group Chemical group 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000006323 alkenyl amino group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005257 alkyl acyl group Chemical group 0.000 abstract 1
- 125000005277 alkyl imino group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
-
- 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
- C07D405/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74486791A | 1991-08-14 | 1991-08-14 | |
| PCT/US1992/006684 WO1993004061A1 (en) | 1991-08-14 | 1992-08-10 | Novel 4-oxocyclic ureas useful as antiarrhythmic and antifibrillatory agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO992898L true NO992898L (no) | 1994-02-14 |
| NO992898D0 NO992898D0 (no) | 1999-06-14 |
| NO310145B1 NO310145B1 (no) | 2001-05-28 |
Family
ID=24994275
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO940497A NO306676B1 (no) | 1991-08-14 | 1994-02-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
| NO19992900A NO310147B1 (no) | 1991-08-14 | 1999-06-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
| NO19992899A NO310146B1 (no) | 1991-08-14 | 1999-06-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
| NO19992898A NO310145B1 (no) | 1991-08-14 | 1999-06-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
| NO19992897A NO310148B1 (no) | 1991-08-14 | 1999-06-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO940497A NO306676B1 (no) | 1991-08-14 | 1994-02-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
| NO19992900A NO310147B1 (no) | 1991-08-14 | 1999-06-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
| NO19992899A NO310146B1 (no) | 1991-08-14 | 1999-06-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19992897A NO310148B1 (no) | 1991-08-14 | 1999-06-14 | Nye 4-oksocykliske urinstoffer som er nyttige som antiarytmiske og antifibrillatoriske midler |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5462940A (no) |
| EP (2) | EP1231208A3 (no) |
| JP (1) | JP3040473B2 (no) |
| KR (2) | KR100273605B1 (no) |
| AT (1) | ATE220675T1 (no) |
| AU (1) | AU668360B2 (no) |
| BR (1) | BR9206369A (no) |
| CA (1) | CA2115427C (no) |
| CZ (1) | CZ282368B6 (no) |
| DE (1) | DE69232681T2 (no) |
| DK (1) | DK0598061T3 (no) |
| ES (1) | ES2180537T3 (no) |
| FI (1) | FI109696B (no) |
| HK (1) | HK1048806A1 (no) |
| HU (1) | HU221317B1 (no) |
| IL (1) | IL102793A (no) |
| MX (1) | MX9204730A (no) |
| MY (1) | MY109205A (no) |
| NO (5) | NO306676B1 (no) |
| NZ (1) | NZ243938A (no) |
| PH (1) | PH31451A (no) |
| PL (2) | PL170961B1 (no) |
| PT (1) | PT100777B (no) |
| RU (2) | RU2221788C2 (no) |
| SK (1) | SK282656B6 (no) |
| TW (1) | TW232691B (no) |
| WO (1) | WO1993004061A1 (no) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6083945A (en) * | 1995-06-07 | 2000-07-04 | The Procter & Gamble Company | Cyclic ureas useful as antiarrhythmic and antifibrillatory agents |
| US6262068B1 (en) | 1997-02-21 | 2001-07-17 | Bristol-Myers Squibb Company | Lactam derivatives as antiarrhythmic agents |
| US6048877A (en) * | 1997-02-21 | 2000-04-11 | Bristol-Myers Squibb Company | Tetralone derivatives as antiarrhythmic agents |
| WO1998037068A1 (en) | 1997-02-21 | 1998-08-27 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
| US6664250B2 (en) | 1998-01-20 | 2003-12-16 | Bristol-Myers Squibb Co. | Lactam derivatives as antiarrhythmic agents |
| IL137917A0 (en) | 1998-02-20 | 2001-10-31 | Procter & Gamble | Solid phase synthesis of 1-aminohydantoins |
| RU2194706C2 (ru) | 1998-04-29 | 2002-12-20 | Дзе Проктер Энд Гэмбл Компани | Способ получения дигидрохлорида 1-[[[5-(4-хлорфенил)-2-фуранил]метилен]амино]-3-[4-(4-метил-1-пиперазинил) бутил]-2,4-имидазолидиндиона |
| HUP0101356A3 (en) | 1998-04-29 | 2003-08-28 | Procter & Gamble | Process for making 1,3-disubstituted-4-oxocyclic ureas |
| CN100443473C (zh) * | 2005-04-30 | 2008-12-17 | 中国药科大学 | 1-氨基-3-(氮杂环基烷基)-2,4-咪唑二酮的合成方法 |
| US20090023183A1 (en) * | 2005-10-18 | 2009-01-22 | Seoul National University Industry Foundation | Method For Preparing Recombinant Peptide From Spider Venom and Analgesic Composition Containing The Peptide |
| US20120178762A1 (en) | 2006-12-15 | 2012-07-12 | Warner Chilcott Company, Llc | Compositions of azimilide dihydrochloride |
| TW200840578A (en) * | 2006-12-15 | 2008-10-16 | Procter & Gamble | Compositions of azimilide dihydrochloride |
| CN101735203B (zh) * | 2009-12-17 | 2012-05-23 | 天津药物研究院 | 盐酸阿齐利特的晶型ⅱ及其制备方法和用途 |
| CN101735205B (zh) * | 2009-12-17 | 2013-05-15 | 天津药物研究院 | 盐酸阿齐利特的晶型ⅴ及其制备方法和用途 |
| CN101735202B (zh) * | 2009-12-17 | 2012-05-30 | 天津药物研究院 | 盐酸阿齐利特的晶型ⅰ及其制备方法和用途 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB939941A (en) * | 1959-04-14 | 1963-10-16 | Norwich Pharma Co | Improvements in or relating to the manufacture of derivatives of 5-nitrofuran |
| US3182058A (en) * | 1960-10-31 | 1965-05-04 | Pfizer & Co C | Nitrofuran derivatives |
| DE1202281B (de) * | 1960-11-21 | 1965-10-07 | Josef Klosa Dipl Chem Dr | Verfahren zur Herstellung von N-(5-Nitro-2-furfuryliden)-1-aminohydantoinen |
| FR1310188A (no) * | 1960-12-27 | 1963-03-06 | ||
| NL129329C (no) * | 1960-12-27 | 1900-01-01 | ||
| NL272960A (no) * | 1960-12-27 | |||
| FR1310187A (no) * | 1960-12-27 | 1963-03-06 | ||
| DE1201845B (de) * | 1962-07-14 | 1965-09-30 | Zambon Spa | Verfahren zur Herstellung von N-(5-Nitro-2-furfuryliden)-1-aminohydantoin |
| NL300307A (no) * | 1963-06-10 | |||
| US3415821A (en) * | 1965-09-07 | 1968-12-10 | Norwich Pharma Co | 1-(5-substituted)furfurylideneamino hydantoins and imidazolidinones |
| NL6900631A (no) * | 1968-01-26 | 1969-07-29 | ||
| JPS5032271B2 (no) * | 1973-06-06 | 1975-10-18 | ||
| US4001222A (en) * | 1975-10-14 | 1977-01-04 | Morton-Norwich Products, Inc. | 3-(Aminoacyl)-1-{[5-(substituted phenyl)furfurylidene]amino}hydantoins and process for their preparation thereof |
| US4775670A (en) * | 1980-09-29 | 1988-10-04 | E. R. Squibb & Sons, Inc. | 2-oxo-1-azetidinesulfonic acid salts |
| US4393204A (en) * | 1982-05-21 | 1983-07-12 | Norwich Eaton Pharmaceuticals, Inc. | 3-[[5-(4-Chlorophenyl)furfurylidene]amino]-5-(substituted)-2-oxazolidinones |
| JPS5913780A (ja) * | 1982-07-13 | 1984-01-24 | Takeda Chem Ind Ltd | フルオロウラシル誘導体および抗腫瘍剤 |
| US4543359A (en) * | 1982-10-01 | 1985-09-24 | Eaton Laboratories, Inc. | Treating cardiac arrhythmias with dantrolene sodium |
| FR2539412B1 (fr) * | 1983-01-13 | 1986-02-21 | Shoichiro Ozaki | Derives du 5-fluoruracile et leurs utilisations therapeutiques en tant qu'agents carcinostatiques |
| US4705799A (en) * | 1983-06-07 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents |
| US4581370A (en) * | 1983-07-12 | 1986-04-08 | Schering A.G. | Antiarrhythmic imidazoliums |
| US4720580A (en) * | 1984-09-21 | 1988-01-19 | American Home Products Corporation | N-(aminoalkylene)benzenesulfonamides |
| US4713382A (en) * | 1985-05-30 | 1987-12-15 | Syntex (U.S.A.) Inc. | N-phenyl-4-phenyl-1-piperazinecarboxamidines and related compounds as antiarrhythmic agents |
| US4707499A (en) * | 1985-12-02 | 1987-11-17 | G. D. Searle & Co. | 3-alkyl-5-(substituted amino)methyl)dihydro-3-phenyl-2(3H)-furanones and imino analogs thereof used for treatment of arrhythmia |
| GB8603120D0 (en) * | 1986-02-07 | 1986-03-12 | Pfizer Ltd | Anti-dysrhythmia agents |
| PH23283A (en) * | 1986-02-26 | 1989-06-30 | Eisai Co Ltd | Piperidine derivative, pharmaceutical composition containing the same and method of use thereof |
| US4804662A (en) * | 1987-05-05 | 1989-02-14 | Schering A.G. | Substituted 4-(1H-imidazol-1-yl)benzamides as antiarrhythmic agents |
| US4851526A (en) * | 1987-09-04 | 1989-07-25 | Schering A.G. | 1-(4-Substituted phenyl)-1H-imidazoles compounds |
| US4870095A (en) * | 1988-06-13 | 1989-09-26 | Sterling Drug, Inc. | 1H-pyrazole-1-alkanamides, antiarrhythmic compositions and use |
| JPH0276882A (ja) * | 1988-06-20 | 1990-03-16 | Eisai Co Ltd | 光学活性ヒダントイン誘導体 |
| CA2020813C (en) * | 1989-07-25 | 1995-08-01 | Frederick Dana Cazer | Nitrofurantoin crystals |
| US4966967A (en) * | 1989-09-15 | 1990-10-30 | Berlex Laboratories, Inc. | 3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonines as cardiovascular agents |
| US5032598A (en) * | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents |
| US4994459A (en) * | 1989-12-11 | 1991-02-19 | American Home Products Corporation | Aryloxypropane substituted piperazine derivatives with antiarrhythmic and antifibrillatory activity |
| US4963561A (en) * | 1990-02-28 | 1990-10-16 | Sterling Drug Inc. | Imidazopyridines, their preparation and use |
| CA2115029C (en) * | 1991-08-14 | 2002-03-26 | Stanford Salvatore Pelosi, Jr. | Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents |
| DK0598046T3 (da) * | 1991-08-14 | 1999-05-25 | Procter & Gamble Pharma | Hidtil ukendte urinstoffer egnede som antiarrytmi- og antifibrilleringsmidler |
-
1992
- 1992-08-10 CZ CZ94306A patent/CZ282368B6/cs not_active IP Right Cessation
- 1992-08-10 BR BR9206369A patent/BR9206369A/pt not_active Application Discontinuation
- 1992-08-10 DE DE69232681T patent/DE69232681T2/de not_active Expired - Lifetime
- 1992-08-10 EP EP02075117A patent/EP1231208A3/en not_active Withdrawn
- 1992-08-10 KR KR1019940700427A patent/KR100273605B1/ko not_active IP Right Cessation
- 1992-08-10 RU RU99101341/04A patent/RU2221788C2/ru not_active IP Right Cessation
- 1992-08-10 CA CA002115427A patent/CA2115427C/en not_active Expired - Lifetime
- 1992-08-10 HU HU9400396A patent/HU221317B1/hu unknown
- 1992-08-10 SK SK171-94A patent/SK282656B6/sk not_active IP Right Cessation
- 1992-08-10 JP JP5504376A patent/JP3040473B2/ja not_active Expired - Fee Related
- 1992-08-10 PL PL92302377A patent/PL170961B1/pl unknown
- 1992-08-10 EP EP92918467A patent/EP0598061B1/en not_active Expired - Lifetime
- 1992-08-10 AU AU24717/92A patent/AU668360B2/en not_active Expired
- 1992-08-10 PL PL92314009A patent/PL170984B1/pl unknown
- 1992-08-10 ES ES92918467T patent/ES2180537T3/es not_active Expired - Lifetime
- 1992-08-10 DK DK92918467T patent/DK0598061T3/da active
- 1992-08-10 AT AT92918467T patent/ATE220675T1/de active
- 1992-08-10 RU RU94015844A patent/RU2130935C1/ru not_active IP Right Cessation
- 1992-08-10 WO PCT/US1992/006684 patent/WO1993004061A1/en active IP Right Grant
- 1992-08-12 IL IL10279392A patent/IL102793A/en not_active IP Right Cessation
- 1992-08-12 PH PH44800A patent/PH31451A/en unknown
- 1992-08-13 NZ NZ243938A patent/NZ243938A/en unknown
- 1992-08-14 MX MX9204730A patent/MX9204730A/es unknown
- 1992-08-14 MY MYPI92001463A patent/MY109205A/en unknown
- 1992-08-14 PT PT100777A patent/PT100777B/pt not_active IP Right Cessation
- 1992-08-22 TW TW081106647A patent/TW232691B/zh not_active IP Right Cessation
-
1994
- 1994-02-11 FI FI940657A patent/FI109696B/fi not_active IP Right Cessation
- 1994-02-14 NO NO940497A patent/NO306676B1/no not_active IP Right Cessation
- 1994-06-03 US US08/275,461 patent/US5462940A/en not_active Expired - Lifetime
-
1999
- 1999-06-14 NO NO19992900A patent/NO310147B1/no not_active IP Right Cessation
- 1999-06-14 NO NO19992899A patent/NO310146B1/no not_active IP Right Cessation
- 1999-06-14 NO NO19992898A patent/NO310145B1/no not_active IP Right Cessation
- 1999-06-14 NO NO19992897A patent/NO310148B1/no not_active IP Right Cessation
- 1999-11-01 KR KR1019997010110A patent/KR100295946B1/ko not_active IP Right Cessation
-
2003
- 2003-01-30 HK HK03100753.4A patent/HK1048806A1/zh unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |