NO178067C - Analogifremgangsmåte til fremstilling av terapautisk aktive heterocykliske forbindelser - Google Patents
Analogifremgangsmåte til fremstilling av terapautisk aktive heterocykliske forbindelserInfo
- Publication number
- NO178067C NO178067C NO900336A NO900336A NO178067C NO 178067 C NO178067 C NO 178067C NO 900336 A NO900336 A NO 900336A NO 900336 A NO900336 A NO 900336A NO 178067 C NO178067 C NO 178067C
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- chem
- heterocyclic compounds
- alkyl group
- hydrogen
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Saccharide Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Detergent Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898903130A GB8903130D0 (en) | 1989-02-11 | 1989-02-11 | Substituted pyridazinones |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO900336D0 NO900336D0 (no) | 1990-01-24 |
| NO900336L NO900336L (no) | 1990-08-13 |
| NO178067B NO178067B (no) | 1995-10-09 |
| NO178067C true NO178067C (no) | 1996-01-17 |
Family
ID=10651554
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO900336A NO178067C (no) | 1989-02-11 | 1990-01-24 | Analogifremgangsmåte til fremstilling av terapautisk aktive heterocykliske forbindelser |
| NO2001020C NO2001020I1 (no) | 1989-02-11 | 2001-11-19 | Levosimendan |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2001020C NO2001020I1 (no) | 1989-02-11 | 2001-11-19 | Levosimendan |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5019575A (no) |
| EP (1) | EP0383449B1 (no) |
| JP (1) | JP3011955B2 (no) |
| CN (1) | CN1036265C (no) |
| AT (1) | ATE127456T1 (no) |
| AU (1) | AU619648B2 (no) |
| CA (1) | CA2009678C (no) |
| CZ (1) | CZ286036B6 (no) |
| DD (1) | DD293112A5 (no) |
| DE (1) | DE69022078T2 (no) |
| DK (1) | DK0383449T3 (no) |
| ES (1) | ES2078939T3 (no) |
| FI (1) | FI96511C (no) |
| GB (2) | GB8903130D0 (no) |
| GR (1) | GR3017510T3 (no) |
| HU (2) | HU206692B (no) |
| LT (1) | LT3769B (no) |
| LU (1) | LU90921I2 (no) |
| NO (2) | NO178067C (no) |
| NZ (1) | NZ232257A (no) |
| PT (1) | PT93111B (no) |
| RU (3) | RU2048467C1 (no) |
| SK (1) | SK55790A3 (no) |
| ZA (1) | ZA90681B (no) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8824458D0 (en) * | 1988-10-19 | 1988-11-23 | Orion Yhtymae Oy | Substituted pyridazinones |
| IE62890B1 (en) * | 1988-12-06 | 1995-03-08 | Hafslund Nycomed Pharma | New piperazinylalkyl-3(2h)-pyridazinones process for the preparation thereof and the use thereof as agents lowering blood pressure |
| GB8903130D0 (en) * | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
| GB2251615B (en) * | 1991-01-03 | 1995-02-08 | Orion Yhtymae Oy | (-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]pro panedinitrile |
| GB2266841A (en) * | 1992-05-06 | 1993-11-17 | Orion Yhtymae Oy | Compounds for use as anti-ischemic medicaments |
| DE4239540A1 (de) * | 1992-11-25 | 1994-05-26 | Asta Medica Ag | Neue heterocyclische Verbindungen mit antiasthmatischer/antiallergischer, entzündungshemmender, positiv inotroper und blutdrucksenkender Wirkung |
| TW309520B (no) * | 1994-04-26 | 1997-07-01 | Mitsubishi Chem Corp | |
| DE19514568A1 (de) | 1995-04-20 | 1996-10-24 | Merck Patent Gmbh | Arylalkyl-pyridazinone |
| GB9606474D0 (en) * | 1996-03-27 | 1996-06-05 | Orion Yhytmo Oy | Method for obtaining pure enantiomers of a pyridazinone derivative |
| GB9626472D0 (en) | 1996-12-20 | 1997-02-05 | Aperia Anita C | New use of comt inhibitors |
| FI973804A (fi) * | 1997-09-26 | 1999-03-27 | Orion Yhtymae Oy | Levosimendaanin oraalisia koostumuksia |
| FI980901A (fi) * | 1998-04-23 | 1999-10-24 | Orion Yhtymae Oyj | Levosimendaania säädellysti vapauttavia oraalisia koostumuksia |
| FI980902A (fi) | 1998-04-23 | 1999-10-24 | Orion Yhtymae Oyj | Levosimendaanin stabiileja koostumuksia |
| FI105389B (fi) * | 1998-04-23 | 2000-08-15 | Orion Yhtymae Oyj | Menetelmä levosimendaaniannon siedettävyyden seuraamiseksi |
| FI104718B (fi) | 1998-06-18 | 2000-03-31 | Orion Yhtymae Oyj | [[4-(2-atsido-3-metyyli-5-oksotetrahydrofuran-2-yyli)fenyyli]hydratsono]propaanidinitriili käytettäväksi referenssiaineena levosimendaanierien analyysissä |
| FI20000577A0 (fi) * | 2000-03-13 | 2000-03-13 | Orion Yhtymae Oy | Pyridatsinyylifenyylihydratsoneja |
| FI20002525A (fi) * | 2000-11-17 | 2002-05-18 | Orion Yhtymae Oyj | Tulehduksenvastaisia aineita |
| WO2002072099A1 (fr) * | 2001-03-14 | 2002-09-19 | Mitsubishi Pharma Corporation | Agent therapeutique et / ou prophylactique pour la cardiopathie ischemique diabetique |
| EP1612204A4 (en) * | 2003-03-31 | 2007-04-11 | Daiichi Seiyaku Co | HYDRAZONE DERIVATIVE |
| DE102004011512B4 (de) | 2004-03-08 | 2022-01-13 | Boehringer Ingelheim Vetmedica Gmbh | Pharmazeutische Zubereitung enthaltend Pimobendan |
| EP1579862A1 (en) | 2004-03-25 | 2005-09-28 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the reduction of heart size in mammals suffering from heart failure |
| US8980894B2 (en) | 2004-03-25 | 2015-03-17 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the treatment of asymptomatic (occult) heart failure |
| CA2568393A1 (en) * | 2004-05-28 | 2005-12-15 | Abbott Laboratories | Methods for treating a mammal before, during and after cardiac arrest |
| PL1951227T3 (pl) | 2005-11-14 | 2017-09-29 | Boehringer Ingelheim Vetmedica Gmbh | Zastosowania pimobendanu do leczenia bezobjawowej(utajonej) niewydolności serca |
| CA2858816A1 (en) | 2006-07-25 | 2008-01-31 | Cephalon, Inc. | Pyridizinone derivatives and uses thereof to treat diseases, disorders and/or conditions that may be mediated or modulated by inhibition of h3 receptors |
| EP1920785A1 (en) | 2006-11-07 | 2008-05-14 | Boehringer Ingelheim Vetmedica Gmbh | Liquid preparation comprising a complex of pimobendan and cyclodextrin |
| FR2917975B1 (fr) | 2007-06-26 | 2009-10-16 | Ceva Sante Animale Sa | Compositions et traitement de l'insuffisance cardiaque chez les animaux mammiferes non humains |
| CA2645772A1 (en) * | 2007-12-05 | 2009-06-05 | Tagawa Greenhouse Enterprises, Llc | Collapsible support apparatus and methods |
| MX2011005444A (es) | 2008-11-25 | 2011-06-09 | Boehringer Ingelheim Vetmed | Inhibidores de la fosfodiesterasa tipo iii (pde iii) o agentes sensibilizantes a iones de ca(2+) para el tratamiento de la cardiomiopatia hipertrofica. |
| EP2825159B1 (en) | 2012-03-15 | 2022-06-22 | Boehringer Ingelheim Vetmedica GmbH | Pharmaceutical tablet formulation for the veterinary medical sector, method of production and use thereof |
| EP3252049A1 (en) * | 2013-01-18 | 2017-12-06 | Bristol-Myers Squibb Company | Phthalazinones and isoquinolinones as rock inhibitors |
| WO2015007760A1 (en) | 2013-07-19 | 2015-01-22 | Boehringer Ingelheim Vetmedica Gmbh | Preserved etherified cyclodextrin derivatives containing liquid aqueous pharmaceutical composition |
| EP3106150B1 (en) | 2013-12-04 | 2021-07-28 | Boehringer Ingelheim Vetmedica GmbH | Improved pharmaceutical compositions of pimobendan |
| US10537570B2 (en) | 2016-04-06 | 2020-01-21 | Boehringer Ingelheim Vetmedica Gmbh | Use of pimobendan for the reduction of heart size and/or the delay of onset of clinical symptoms in patients with asymptomatic heart failure due to mitral valve disease |
| EP3424908A1 (en) | 2017-07-07 | 2019-01-09 | Melody Healthcare Pvt. Ltd. | Process for preparation of levosimendan |
| KR102128509B1 (ko) * | 2018-12-19 | 2020-07-01 | 한국과학기술연구원 | 말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체 및 이의 용도 |
| CN111548310B (zh) * | 2020-05-12 | 2021-07-02 | 成都欣捷高新技术开发股份有限公司 | 一种左西孟旦钠晶型及其制备方法 |
| US11760730B2 (en) | 2021-01-11 | 2023-09-19 | Navinta, Llc | Process for the preparation of high purity Levosimendan |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3432507A (en) * | 1963-12-04 | 1969-03-11 | Upjohn Co | Certain diazatricyclododecadienones and their preparation |
| EP0052442B1 (en) * | 1980-11-14 | 1985-09-11 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| US4353905A (en) * | 1981-09-17 | 1982-10-12 | Warner-Lambert Company | Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones |
| US4495185A (en) * | 1981-11-12 | 1985-01-22 | Imperial Chemical Industries, Plc | 1,2,4-Triazin-3(2H) ones |
| JPS58113180A (ja) * | 1981-12-28 | 1983-07-05 | Mitsui Toatsu Chem Inc | ピリダジノン誘導体 |
| US4581356A (en) * | 1983-03-22 | 1986-04-08 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
| GB8310435D0 (en) * | 1983-04-18 | 1983-05-25 | Fujisawa Pharmaceutical Co | Triazine derivatives |
| JPS59196874A (ja) * | 1983-04-22 | 1984-11-08 | Fujisawa Pharmaceut Co Ltd | トリアジン誘導体 |
| US4599332A (en) * | 1983-12-07 | 1986-07-08 | Warner-Lambert Company | 4,5-dihydro-6-[2-[4-(1H-imidazol-1-yl)phenyl]-ethenyl]-3(2H)-pyridazinones and related compounds |
| JPS61158969A (ja) * | 1984-12-24 | 1986-07-18 | ワーナー‐ランバート・コンパニー | ４，５‐ジヒドロ‐４，４‐ジアルキル‐６‐（置換）フエニル‐３（２ｈ）‐ピリダジノン類 |
| US4656170A (en) * | 1985-05-28 | 1987-04-07 | Warner-Lambert Company | N-[4-[2-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)ethenyl]phenyl]acetamide and related compounds |
| US4946842A (en) * | 1985-07-05 | 1990-08-07 | Smith Kline & French Laboratories Limited | Novel guanidino pyridazinones as cardiac stimulants |
| DE3531658A1 (de) | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Heterocyclisch substituierte indole, zwischenprodukte, verfahren zu ihrer herstellung und arzneimittel |
| GB8603780D0 (en) * | 1986-02-15 | 1986-03-19 | Smith Kline French Lab | Chemical compounds |
| US4898862A (en) * | 1986-03-20 | 1990-02-06 | Sankyo Company Limited | 1,2,4-triazinone derivatives, their preparation and use |
| IT1208003B (it) * | 1987-01-08 | 1989-06-01 | Isf Spa | Procedimento per preparare derivati alcossi alchiliden, idrazino, piridazinici. |
| DE3706427A1 (de) * | 1987-02-27 | 1988-09-08 | Boehringer Mannheim Gmbh | Neue substituierte 3h-indole, zwischenprodukte, verfahren zu ihrer herstellung sowie arzneimittel |
| DE3728491A1 (de) * | 1987-08-26 | 1989-03-09 | Heumann Pharma Gmbh & Co | Dihydropyridazinon-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| JP2717687B2 (ja) * | 1988-02-13 | 1998-02-18 | 日本曹達株式会社 | ピリダジノン誘導体及びその製造方法 |
| GB8903130D0 (en) * | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
-
1989
- 1989-02-11 GB GB898903130A patent/GB8903130D0/en active Pending
-
1990
- 1990-01-24 NO NO900336A patent/NO178067C/no not_active IP Right Cessation
- 1990-01-26 GB GB9001853A patent/GB2228004B/en not_active Expired - Lifetime
- 1990-01-26 NZ NZ232257A patent/NZ232257A/en unknown
- 1990-01-29 AT AT90300875T patent/ATE127456T1/de active
- 1990-01-29 ES ES90300875T patent/ES2078939T3/es not_active Expired - Lifetime
- 1990-01-29 EP EP90300875A patent/EP0383449B1/en not_active Expired - Lifetime
- 1990-01-29 DK DK90300875.3T patent/DK0383449T3/da active
- 1990-01-29 DE DE69022078T patent/DE69022078T2/de not_active Expired - Lifetime
- 1990-01-30 ZA ZA90681A patent/ZA90681B/xx unknown
- 1990-02-06 CZ CS90557A patent/CZ286036B6/cs not_active IP Right Cessation
- 1990-02-06 SK SK557-90A patent/SK55790A3/sk not_active IP Right Cessation
- 1990-02-08 FI FI900613A patent/FI96511C/fi active Protection Beyond IP Right Term
- 1990-02-08 AU AU49296/90A patent/AU619648B2/en not_active Expired
- 1990-02-09 RU SU904743235A patent/RU2048467C1/ru active
- 1990-02-09 DD DD90337728A patent/DD293112A5/de not_active IP Right Cessation
- 1990-02-09 US US07/477,530 patent/US5019575A/en not_active Expired - Lifetime
- 1990-02-09 HU HU913501D patent/HU206692B/hu unknown
- 1990-02-09 HU HU90747A patent/HU204797B/hu unknown
- 1990-02-09 JP JP2031339A patent/JP3011955B2/ja not_active Expired - Lifetime
- 1990-02-09 CA CA002009678A patent/CA2009678C/en not_active Expired - Lifetime
- 1990-02-09 PT PT93111A patent/PT93111B/pt not_active IP Right Cessation
- 1990-02-10 CN CN90100645A patent/CN1036265C/zh not_active Expired - Lifetime
-
1991
- 1991-03-15 US US07/670,338 patent/US5122524A/en not_active Expired - Lifetime
- 1991-05-05 RU SU914895242A patent/RU1836362C/ru active
-
1992
- 1992-06-29 RU SU925011896A patent/RU2068844C1/ru active
-
1993
- 1993-09-28 LT LTIP1233A patent/LT3769B/lt not_active IP Right Cessation
-
1995
- 1995-09-22 GR GR950402628T patent/GR3017510T3/el unknown
-
2001
- 2001-11-19 NO NO2001020C patent/NO2001020I1/no unknown
-
2002
- 2002-05-17 LU LU90921C patent/LU90921I2/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |