GB2286395B - Diketopiperazine derivatives and pharmaceutical uses thereof - Google Patents
Diketopiperazine derivatives and pharmaceutical uses thereofInfo
- Publication number
- GB2286395B GB2286395B GB9502874A GB9502874A GB2286395B GB 2286395 B GB2286395 B GB 2286395B GB 9502874 A GB9502874 A GB 9502874A GB 9502874 A GB9502874 A GB 9502874A GB 2286395 B GB2286395 B GB 2286395B
- Authority
- GB
- United Kingdom
- Prior art keywords
- pharmaceutical uses
- diketopiperazine derivatives
- diketopiperazine
- derivatives
- pharmaceutical
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- C07D403/06—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 only aliphatic 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9402807A GB9402807D0 (en) | 1994-02-14 | 1994-02-14 | Pharmaceutical compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9502874D0 GB9502874D0 (en) | 1995-04-05 |
| GB2286395A GB2286395A (en) | 1995-08-16 |
| GB2286395B true GB2286395B (en) | 1998-08-26 |
Family
ID=10750355
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9402807A Pending GB9402807D0 (en) | 1994-02-14 | 1994-02-14 | Pharmaceutical compounds |
| GB9502874A Expired - Fee Related GB2286395B (en) | 1994-02-14 | 1995-02-14 | Diketopiperazine derivatives and pharmaceutical uses thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9402807A Pending GB9402807D0 (en) | 1994-02-14 | 1994-02-14 | Pharmaceutical compounds |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0745070A1 (en) |
| JP (1) | JPH09509157A (en) |
| AU (1) | AU693159B2 (en) |
| CA (1) | CA2182877A1 (en) |
| GB (2) | GB9402807D0 (en) |
| IL (1) | IL112624A0 (en) |
| WO (1) | WO1995021832A1 (en) |
| ZA (1) | ZA951180B (en) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL112627A0 (en) * | 1994-02-14 | 1995-05-26 | Xenova Ltd | Diketopiperazines, their preparation and pharmaceutical or veterinary compositions containing them |
| GB9426090D0 (en) * | 1994-12-23 | 1995-02-22 | Xenova Ltd | Pharmaceutical compounds |
| GB9708805D0 (en) | 1997-05-01 | 1997-06-25 | Smithkline Beecham Plc | Compounds |
| PL336628A1 (en) | 1997-05-03 | 2000-07-03 | Smithkline Beecham Plc | Derivatives of tetrahydroisoquinoline as modulators of d3 dopamine receptors |
| EP1237376B1 (en) | 1997-06-09 | 2015-08-05 | Hitachi, Ltd. | Image information recording medium |
| GB9810876D0 (en) | 1998-05-20 | 1998-07-22 | Smithkline Beecham Plc | Compounds |
| ID28385A (en) | 1998-10-08 | 2001-05-17 | Smithkline Beecham Plc | TETRAHIDROBENZAZEPINA DECREASED USING AS DOPAMINA D3 RECEPTOR MODULATOR (ANTIPSICOTIC MATERIAL) |
| BR0017067A (en) * | 2000-01-18 | 2002-10-22 | Nereus Pharmaceuticals Inc | Cell division inhibitor, dehydrogenase, method for producing a cell division and compound inhibitor |
| NZ522680A (en) * | 2000-05-09 | 2005-08-26 | Adpharma Inc | Piperazinedione compounds |
| US6635649B2 (en) * | 2000-05-09 | 2003-10-21 | Che-Ming Teng | Piperazinedione compounds |
| US7288545B2 (en) | 2000-05-09 | 2007-10-30 | Angiorx Corporation | Piperazinedione compounds |
| EP1315777B1 (en) | 2000-09-06 | 2007-10-31 | AP Pharma, Inc. | Degradable polyacetal polymers |
| GB2372740A (en) * | 2001-01-17 | 2002-09-04 | Xenova Ltd | Diketopiperazines |
| TW591020B (en) * | 2001-06-20 | 2004-06-11 | Wyeth Corp | 6-(aryl-amido or aryl-amidomethyl)-naphthalen-2-yloxy-acidic derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1) |
| US7919497B2 (en) | 2002-08-02 | 2011-04-05 | Nereus Pharmaceuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| US7935704B2 (en) | 2003-08-01 | 2011-05-03 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| ES2295695T3 (en) * | 2002-08-02 | 2008-04-16 | Nereus Pharmaceuticals, Inc. | DEHYDROPHENYLHYSINAS AND ITS ANALOGS AND THE SYNTHESIS OF DEHYDROPHENYLHYTHINES AND THEIR ANALOGS. |
| CA2553630A1 (en) * | 2004-02-04 | 2005-08-25 | Nereus Pharmaceuticals, Inc. | Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof |
| TWI335816B (en) | 2004-05-26 | 2011-01-11 | Eisai R&D Man Co Ltd | Cinnamide compound |
| DE602005019602D1 (en) | 2004-10-26 | 2010-04-08 | Eisai R&D Man Co Ltd | AMORPHIC FORM OF A CINEMA ACID AMID CONNECTION |
| TWI370130B (en) | 2005-11-24 | 2012-08-11 | Eisai R&D Man Co Ltd | Two cyclic cinnamide compound |
| TWI378091B (en) | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| EP2072498A4 (en) | 2006-10-12 | 2012-07-18 | Inst Med Molecular Design Inc | N-PHENYLOXAMIDE ACID DERIVATIVE |
| JP5207972B2 (en) | 2006-10-12 | 2013-06-12 | 株式会社医薬分子設計研究所 | Carboxylic acid derivatives |
| US8129527B2 (en) | 2006-11-03 | 2012-03-06 | Nereus Pharmacuticals, Inc. | Analogs of dehydrophenylahistins and their therapeutic use |
| TW200848054A (en) | 2007-02-28 | 2008-12-16 | Eisai R&D Man Co Ltd | Two cyclic oxomorpholine derivatives |
| US7935815B2 (en) | 2007-08-31 | 2011-05-03 | Eisai R&D Management Co., Ltd. | Imidazoyl pyridine compounds and salts thereof |
| JP5433418B2 (en) | 2007-08-31 | 2014-03-05 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Polycyclic compound |
| BRPI0816560A2 (en) | 2007-10-23 | 2015-09-01 | Inst Med Molecular Design Inc | Parent-1 production inhibition method method for prevention or amelioration of a disease caused by over-production of parent-1 " |
| EP2272817A4 (en) | 2008-04-11 | 2011-12-14 | Inst Med Molecular Design Inc | INHIBITOR OF PAI-1 |
| EP2318379A1 (en) * | 2008-08-13 | 2011-05-11 | Basf Se | Method for preparation of piperazindione derivates |
| CN105452226B (en) * | 2012-12-21 | 2017-09-12 | Epizyme股份有限公司 | Tetrahydro- and dihydro-isoquinoline PRMT5 inhibitors and uses thereof |
| CN105272968B (en) * | 2014-06-10 | 2018-03-13 | 首都医科大学 | The diketone of (3S, 6R) 3,6 disubstituted piperazine 2,5, it is prepared and application |
| WO2016034671A1 (en) | 2014-09-03 | 2016-03-10 | Ctxt Pty Ltd | Aminoindane-, aminotetrahydronaphthalene- and aminobenzocyclobutane-derived prmt5-inhibitors |
| GB201415573D0 (en) | 2014-09-03 | 2014-10-15 | Cancer Therapeutics Crc Pty Ltd | Compounds |
| EP3189041B1 (en) | 2014-09-03 | 2021-04-28 | Ctxt Pty Ltd | Tetrahydroisoquinoline derived prmt5-inhibitors |
| RU2728796C2 (en) | 2015-03-06 | 2020-07-31 | Бейондспринг Фармасьютикалс, Инк. | Method for treating a brain tumor |
| JP6769982B2 (en) | 2015-03-06 | 2020-10-14 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | How to treat cancer associated with RAS mutations |
| KR102680823B1 (en) | 2015-07-13 | 2024-07-03 | 비욘드스프링 파마수티컬스, 인코포레이티드. | Plinabulin composition |
| BR112018016054A2 (en) | 2016-02-08 | 2019-02-12 | Beyondspring Pharmaceuticals, Inc. | pharmaceutical compositions and / or methods for treating cancer and / or for disrupting cancer-associated tumor vasculature in an individual |
| GB201604030D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604020D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604022D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604027D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604029D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604031D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| CN118304304A (en) | 2016-06-06 | 2024-07-09 | 大连万春布林医药有限公司 | Compositions and methods for reducing neutropenia |
| CN106565686B (en) * | 2016-10-11 | 2019-03-01 | 深圳海王医药科技研究院有限公司 | Antitubulin |
| US11633393B2 (en) | 2017-01-06 | 2023-04-25 | Beyondspring Pharmaceuticals, Inc. | Tubulin binding compounds and therapeutic use thereof |
| JP2020514412A (en) | 2017-02-01 | 2020-05-21 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | Methods for reducing neutropenia |
| CN111108105B (en) | 2017-09-22 | 2023-03-31 | 朱比兰特埃皮帕德有限公司 | Heterocyclic compounds as PAD inhibitors |
| PL3697785T3 (en) | 2017-10-18 | 2023-08-07 | Jubilant Epipad LLC | IMIDAZOPYRIDINE COMPOUNDS AS PAD INHIBITORS |
| KR20200085836A (en) | 2017-11-06 | 2020-07-15 | 주빌런트 프로델 엘엘씨 | Pyrimidine derivatives as PD1/PD-L1 activation inhibitors |
| DK3704120T3 (en) | 2017-11-24 | 2024-05-21 | Jubilant Episcribe Llc | HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS |
| EP3743074A4 (en) | 2018-01-24 | 2021-12-15 | Beyondspring Pharmaceuticals Inc. | COMPOSITION AND METHOD OF REDUCING THROMBOCYTOPENIA VIA PLINABULIN ADMINISTRATION |
| EP3765453A1 (en) | 2018-03-13 | 2021-01-20 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| US20240197723A1 (en) | 2021-04-09 | 2024-06-20 | Beyondspring Pharmaceuticals, Inc. | Therapeutic compositions and methods for treating tumors |
| CN116239578B (en) * | 2022-12-08 | 2024-09-13 | 中国海洋大学 | Piperazine dione ring compound, synthesis method thereof and application thereof in preparation of antitumor drugs |
| CN116400068B (en) * | 2023-02-13 | 2023-09-22 | 泉州圣源警用侦察设备有限公司 | A reagent and method for displaying potential biological traces containing DNA |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE621862C (en) * | 1932-07-01 | 1935-11-14 | Guenther Schiemann Dr | Process for the preparation of condensation products of nucleus fluorinated aryl aldehydes |
| GB9217331D0 (en) * | 1992-08-14 | 1992-09-30 | Xenova Ltd | Pharmaceutical compounds |
| JPH08247357A (en) * | 1995-03-13 | 1996-09-27 | Zexel Corp | Flange joint and forming method thereof |
-
1994
- 1994-02-14 GB GB9402807A patent/GB9402807D0/en active Pending
-
1995
- 1995-02-13 IL IL11262495A patent/IL112624A0/en unknown
- 1995-02-14 EP EP95908314A patent/EP0745070A1/en not_active Withdrawn
- 1995-02-14 WO PCT/GB1995/000302 patent/WO1995021832A1/en not_active Ceased
- 1995-02-14 JP JP7521082A patent/JPH09509157A/en not_active Ceased
- 1995-02-14 GB GB9502874A patent/GB2286395B/en not_active Expired - Fee Related
- 1995-02-14 ZA ZA951180A patent/ZA951180B/en unknown
- 1995-02-14 AU AU16677/95A patent/AU693159B2/en not_active Ceased
- 1995-02-14 CA CA002182877A patent/CA2182877A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts 65:16969e * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09509157A (en) | 1997-09-16 |
| AU1667795A (en) | 1995-08-29 |
| GB9502874D0 (en) | 1995-04-05 |
| AU693159B2 (en) | 1998-06-25 |
| GB2286395A (en) | 1995-08-16 |
| CA2182877A1 (en) | 1995-08-17 |
| GB9402807D0 (en) | 1994-04-06 |
| ZA951180B (en) | 1996-08-14 |
| WO1995021832A1 (en) | 1995-08-17 |
| IL112624A0 (en) | 1995-05-26 |
| EP0745070A1 (en) | 1996-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20050214 |