AR035366A1 - Derivados de la 2-fenoxi-1-(4-bencilpiperazin-1-il)-etan-1-ona, sus sales de monoclorhidrato y de diclorhidrato, un proceso para su preparacion, y un metodo de utilizacion de los mismos para la elaboracion de un producto radiofarmaceutico destinado al diagnóstico de la enfermedad de alzheimer en un - Google Patents
Derivados de la 2-fenoxi-1-(4-bencilpiperazin-1-il)-etan-1-ona, sus sales de monoclorhidrato y de diclorhidrato, un proceso para su preparacion, y un metodo de utilizacion de los mismos para la elaboracion de un producto radiofarmaceutico destinado al diagnóstico de la enfermedad de alzheimer en unInfo
- Publication number
- AR035366A1 AR035366A1 ARP010105127A ARP010105127A AR035366A1 AR 035366 A1 AR035366 A1 AR 035366A1 AR P010105127 A ARP010105127 A AR P010105127A AR P010105127 A ARP010105127 A AR P010105127A AR 035366 A1 AR035366 A1 AR 035366A1
- Authority
- AR
- Argentina
- Prior art keywords
- preparation
- alzheimer
- disease
- derivatives
- diagnosis
- Prior art date
Links
- 208000024827 Alzheimer disease Diseases 0.000 title abstract 3
- 239000012217 radiopharmaceutical Substances 0.000 title abstract 3
- 238000003745 diagnosis Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- VIHRRLFJXZKRDQ-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-2-phenoxyethanone Chemical class C1CN(CC=2C=CC=CC=2)CCN1C(=O)COC1=CC=CC=C1 VIHRRLFJXZKRDQ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229940121896 radiopharmaceutical Drugs 0.000 abstract 2
- 230000002799 radiopharmaceutical effect Effects 0.000 abstract 2
- 102000004500 CCR1 Receptors Human genes 0.000 abstract 1
- 108010017319 CCR1 Receptors Proteins 0.000 abstract 1
- HQMLIDZJXVVKCW-REOHCLBHSA-N L-alaninamide Chemical compound C[C@H](N)C(N)=O HQMLIDZJXVVKCW-REOHCLBHSA-N 0.000 abstract 1
- 101000655609 Streptomyces azureus Thiostrepton Proteins 0.000 abstract 1
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000008499 blood brain barrier function Effects 0.000 abstract 1
- 210000001218 blood-brain barrier Anatomy 0.000 abstract 1
- 210000005013 brain tissue Anatomy 0.000 abstract 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000002738 chelating agent Substances 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- -1 monoalkylamine Chemical group 0.000 abstract 1
- 230000002285 radioactive effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0459—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0478—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from non-cyclic ligands, e.g. EDTA, MAG3
-
- 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
- A61P25/28—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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Optics & Photonics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Derivados de la 2-fenoxi-1-(4-bencilpiperazin-1-il)-etan-1-ona, de fórmula (1), donde: X1 y X2 son cada uno, independientemente entre sí, halo; R1 y R2 son cada uno, independientemente entre sí, hidrógeno o alquilo, y R3 es hidrógeno, amina, monoalquilamina, dialquilamina, monoaralquilamina, alquilcarbonilamina, alquenilcarbonilamina, haloalquilcarbonilamina, arilcarbonilamina, alcoxialquilcarbonilamina, alcoxicarbonilalquilcarbonilamina, glicinamida, monoalquilglicinamida, arilcarbonilglicinamida, aminocarbonilglicinamida, (aminocarbonil)(alquil)-glicinamida, (alcoxialquilcarbonil)glicinamida, ureido, monoalquilureido, monoarilureido, monoaralquilureido, o alaninamido; y donde cualquiera de X1 o X2 se selecciona del grupo formado por 123I, 125I, 128I, 131I, 75Br, 80Br y 18F; o donde uno de los átomos de carbono en el compuesto es 11C; o una sal aceptable para uso farmacéutico de los mismos. También se describen derivados de la 2-fenoxi-1-(4-bencilpiperazin-1-il)-etan-1-ona, en los cuales R3 es un radical -N(R4)R5, siendo R4 hidrógeno y R5 un quelante capaz de unirse a un átomo de metal radioactivo seleccionado de 1 grupo formado por 99mTc, 186Re y 188Re. Los compuestos radiofarmacéuticos de fórmula (1) tienen la capacidad para atravesar la barrera hematoencefálica y unirse al receptor CCR1 presente en el tejido del cerebro que padecen la enfermedad de Alzheimer. Por consiguiente, son usados para la elaboración de productos radiofarmacéuticos destinados al diagnóstico de la enfermedad de Alzheimer en un ser humano.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24629900P | 2000-11-06 | 2000-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR035366A1 true AR035366A1 (es) | 2004-05-12 |
Family
ID=22930075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP010105127A AR035366A1 (es) | 2000-11-06 | 2001-11-02 | Derivados de la 2-fenoxi-1-(4-bencilpiperazin-1-il)-etan-1-ona, sus sales de monoclorhidrato y de diclorhidrato, un proceso para su preparacion, y un metodo de utilizacion de los mismos para la elaboracion de un producto radiofarmaceutico destinado al diagnóstico de la enfermedad de alzheimer en un |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6676926B2 (es) |
| EP (1) | EP1332138B1 (es) |
| JP (1) | JP4234425B2 (es) |
| KR (1) | KR20030045167A (es) |
| CN (1) | CN1473158A (es) |
| AR (1) | AR035366A1 (es) |
| AT (1) | ATE314354T1 (es) |
| AU (2) | AU2002214034B2 (es) |
| BG (1) | BG107762A (es) |
| BR (1) | BR0115150A (es) |
| CA (1) | CA2424598A1 (es) |
| DE (1) | DE60116365T2 (es) |
| EA (1) | EA006199B1 (es) |
| EE (1) | EE200300216A (es) |
| HR (1) | HRP20030459A2 (es) |
| HU (1) | HUP0301710A3 (es) |
| IL (1) | IL155191A0 (es) |
| JO (1) | JO2207B1 (es) |
| MX (1) | MXPA03003759A (es) |
| NO (1) | NO20032007L (es) |
| NZ (1) | NZ525303A (es) |
| PE (1) | PE20020531A1 (es) |
| PL (1) | PL361631A1 (es) |
| SK (1) | SK287495B6 (es) |
| TW (1) | TWI238820B (es) |
| UY (1) | UY27003A1 (es) |
| WO (1) | WO2002036581A1 (es) |
| YU (1) | YU33203A (es) |
| ZA (1) | ZA200304409B (es) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY27003A1 (es) * | 2000-11-06 | 2002-07-31 | Schering Ag | Productos radiofarmacéuticos para el diagnóstico de la enfermedad de alzheimer |
| DK1438298T3 (da) | 2001-10-22 | 2010-04-12 | Pfizer Prod Inc | Piperazin-derivater med CCR1 receptor-antagonist-aktivitet |
| US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| US7998986B2 (en) | 2001-12-21 | 2011-08-16 | Exelixis Patent Company Llc | Modulators of LXR |
| ES2305769T3 (es) * | 2003-05-07 | 2008-11-01 | Bayer Schering Pharma Aktiengesellschaft | Dispositivo y procedimiento para la fluoracion nucleofila. |
| US8257680B1 (en) | 2004-02-24 | 2012-09-04 | The General Hospital Corporation | Catalytic radiofluorination |
| US9017724B2 (en) | 2004-02-24 | 2015-04-28 | The General Hospital Corporation | Catalytic radiofluorination |
| EP2388017B1 (en) * | 2004-02-24 | 2014-12-24 | The General Hospital Corporation | Catalytic radiofluorination |
| GB0409236D0 (en) * | 2004-04-26 | 2004-05-26 | Novartis Ag | Organic compounds |
| US7833513B2 (en) | 2004-12-03 | 2010-11-16 | Rhode Island Hospital | Treatment of Alzheimer's Disease |
| KR100778888B1 (ko) * | 2005-11-29 | 2007-11-28 | 재단법인서울대학교산학협력재단 | 베타아밀로이드 펩타이드 플라크의 영상화를 위한벤질리덴아닐린 계열의 유도체 및 그의 방사성 동위원소표지화합물 |
| AU2007292874B2 (en) | 2006-09-08 | 2013-11-21 | Rhode Island Hospital | Treatment, prevention, and reversal of alcohol-induced liver disease |
| KR20090066289A (ko) | 2006-09-08 | 2009-06-23 | 로드아일랜드하스피틀 | 알코올 유발성 뇌 질환의 치료, 예방 및 역행 |
| GB0625523D0 (en) | 2006-12-21 | 2007-01-31 | Ge Healthcare Ltd | In vivo imaging agents |
| CN101563305A (zh) * | 2006-12-21 | 2009-10-21 | 哈默史密斯网上成像有限公司 | 放射性标记方法 |
| JP2011502966A (ja) * | 2007-10-31 | 2011-01-27 | アルセレス ファーマシューティカルズ， インコーポレイテッド | ドーパミントランスポーターレベルを評価することによるレビー小体型認知症の診断およびレビー小体型認知症の処置のモニタリングのための方法 |
| EP3231804B1 (en) | 2008-03-21 | 2021-03-03 | The General Hospital Corporation | Compounds and compositions for the detection and treatment of alzheimer's disease and related disorders |
| EP2161256A1 (en) * | 2008-09-08 | 2010-03-10 | Atomic Energy Council - Institute of Nuclear Energy Research | Compound containing carboxylate ester and N2S2 ligand bi-functional groups and manufacturing method thereof |
| EP2163541A1 (en) * | 2008-09-12 | 2010-03-17 | Bayer Schering Pharma Aktiengesellschaft | Piperazine derivatives for binding and imaging amyloid plaques and their use |
| WO2011041470A2 (en) * | 2009-09-30 | 2011-04-07 | Mallinckrodt Inc. | Sustained-release opiate and opiate derivative compositions |
| TW201201846A (en) * | 2010-02-08 | 2012-01-16 | Bayer Schering Pharma Ag | Iodo precursor for a PET imaging agent of amyloid plaques |
| WO2011110511A1 (en) * | 2010-03-11 | 2011-09-15 | Bayer Pharma Aktiengesellschaft | Spect imaging agents of amyloid plaques |
| US9572787B2 (en) | 2011-05-19 | 2017-02-21 | Rhode Island Hospital | Inhibition of renal fibrosis |
| US11623946B2 (en) | 2013-12-27 | 2023-04-11 | National University Corporation Tokyo Medical And Dental University | Diagnosis methods, diagnostic agents, and therapeutic agents against alzheimer's disease and frontotemporal lobar degeneration, and screening methods for these agents |
| AU2016315648B2 (en) * | 2015-08-28 | 2021-04-01 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0576611A4 (en) | 1991-03-13 | 1996-01-24 | Univ Minnesota | Radiopharmaceutical agents for the detection of alzheimer's disease |
| EP0524146A1 (de) | 1991-07-19 | 1993-01-20 | Ciba-Geigy Ag | Aminosubstituierte Piperazinderivate |
| GB9413772D0 (en) | 1994-07-08 | 1994-08-24 | Wyeth John & Brother Ltd | 5-HT1A ligands |
| US5919797A (en) * | 1996-04-24 | 1999-07-06 | Emory University | Halogenated naphthyl methoxy piperidines for mapping serotonin transporter sites |
| AU729415B2 (en) | 1996-07-12 | 2001-02-01 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| FR2758328B1 (fr) | 1997-01-15 | 1999-04-02 | Pf Medicament | Nouvelles amines aromatiques derivees d'amines cycliques utiles comme medicaments |
| US6207665B1 (en) * | 1997-06-12 | 2001-03-27 | Schering Aktiengesellschaft | Piperazine derivatives and their use as anti-inflammatory agents |
| AUPP278498A0 (en) * | 1998-04-03 | 1998-04-30 | Australian Nuclear Science & Technology Organisation | Peripheral benzodiazepine receptor binding agents |
| US6288083B1 (en) | 1998-09-04 | 2001-09-11 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| AUPP818099A0 (en) | 1999-01-14 | 1999-02-11 | Fujisawa Pharmaceutical Co., Ltd. | New n-containing heterocyclic compounds |
| PL350904A1 (en) | 1999-03-26 | 2003-02-10 | Astrazeneca Ab | Novel compounds |
| UY27003A1 (es) * | 2000-11-06 | 2002-07-31 | Schering Ag | Productos radiofarmacéuticos para el diagnóstico de la enfermedad de alzheimer |
-
2001
- 2001-10-31 UY UY27003A patent/UY27003A1/es not_active Application Discontinuation
- 2001-11-01 BR BR0115150-9A patent/BR0115150A/pt not_active IP Right Cessation
- 2001-11-01 AT AT01982450T patent/ATE314354T1/de not_active IP Right Cessation
- 2001-11-01 HU HU0301710A patent/HUP0301710A3/hu unknown
- 2001-11-01 NZ NZ525303A patent/NZ525303A/en unknown
- 2001-11-01 JP JP2002539340A patent/JP4234425B2/ja not_active Expired - Fee Related
- 2001-11-01 EP EP01982450A patent/EP1332138B1/en not_active Expired - Lifetime
- 2001-11-01 EE EEP200300216A patent/EE200300216A/xx unknown
- 2001-11-01 KR KR10-2003-7006187A patent/KR20030045167A/ko not_active Withdrawn
- 2001-11-01 IL IL15519101A patent/IL155191A0/xx unknown
- 2001-11-01 PL PL01361631A patent/PL361631A1/xx not_active Application Discontinuation
- 2001-11-01 SK SK547-2003A patent/SK287495B6/sk not_active IP Right Cessation
- 2001-11-01 EA EA200300507A patent/EA006199B1/ru not_active IP Right Cessation
- 2001-11-01 WO PCT/EP2001/012607 patent/WO2002036581A1/en not_active Ceased
- 2001-11-01 AU AU2002214034A patent/AU2002214034B2/en not_active Ceased
- 2001-11-01 CN CNA01818409XA patent/CN1473158A/zh active Pending
- 2001-11-01 CA CA002424598A patent/CA2424598A1/en not_active Abandoned
- 2001-11-01 DE DE60116365T patent/DE60116365T2/de not_active Expired - Lifetime
- 2001-11-01 AU AU1403402A patent/AU1403402A/xx active Pending
- 2001-11-01 YU YU33203A patent/YU33203A/sh unknown
- 2001-11-01 HR HR20030459A patent/HRP20030459A2/hr not_active Application Discontinuation
- 2001-11-01 MX MXPA03003759A patent/MXPA03003759A/es unknown
- 2001-11-02 AR ARP010105127A patent/AR035366A1/es unknown
- 2001-11-05 PE PE2001001092A patent/PE20020531A1/es not_active Application Discontinuation
- 2001-11-05 JO JO2001178A patent/JO2207B1/en active
- 2001-11-06 US US09/985,938 patent/US6676926B2/en not_active Expired - Fee Related
- 2001-11-06 TW TW090127552A patent/TWI238820B/zh not_active IP Right Cessation
-
2003
- 2003-04-25 BG BG107762A patent/BG107762A/xx unknown
- 2003-05-05 NO NO20032007A patent/NO20032007L/no unknown
- 2003-06-05 ZA ZA200304409A patent/ZA200304409B/en unknown
- 2003-07-25 US US10/626,725 patent/US6872381B1/en not_active Expired - Fee Related
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