BR9612099A - Processo para preparar um composto derivado de piperidina, regioisÈmero, processo para preparar um regioisÈmero, derivado de ácido 4-( alfa,alfa, di-substuìdo) toluico e 4- (alfa, alfa-di-não substitìdo) toluico. - Google Patents
Processo para preparar um composto derivado de piperidina, regioisÈmero, processo para preparar um regioisÈmero, derivado de ácido 4-( alfa,alfa, di-substuìdo) toluico e 4- (alfa, alfa-di-não substitìdo) toluico.Info
- Publication number
- BR9612099A BR9612099A BR9612099-1A BR9612099A BR9612099A BR 9612099 A BR9612099 A BR 9612099A BR 9612099 A BR9612099 A BR 9612099A BR 9612099 A BR9612099 A BR 9612099A
- Authority
- BR
- Brazil
- Prior art keywords
- alpha
- regioisomer
- preparing
- toluic acid
- derived
- Prior art date
Links
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 title 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/54—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
"PROCESSO PARA PREPARAR UM COMPOSTO DERIVADO DE PIPERIDINA, REGIOISÈMERO, PROCESSO PARA PREPARA UM REGIOISÈMERO, DERIVADO DE áCIDO 4-(<244>, <244>- DI-SUBSTITUìDO) TOLUICO E 4-(<244>, <244>- DI-NãO SUBSTITUìDO)TOLUICO". A presente invenção descreve o processo para preparar os compostos de derivado piperdina da fórmula (I) ou (II): em que n é 0 ou 1; R^ 1^ é hidrogênio ou hidroxi, R^ 2^ é hidrogênio; ou, quando n é 0, R^ 1^ e R^ 2^ tomados juntos formam uma segunda ligação entre os átomos de carbono contendo R^ 1^ e R^ 2^, desde que quando n é 1, R^ 1^ e R^ 2^ cada são hidrogênio; R^ 3^ é -COOH ou -COOR^ 4^, R^ 4^ é uma porção alquila ou arila; A, B, e D são os substituintes de seus anéis, cada podendo ser igual ao diferente, e são selecionados dentre o grupo consistindo de hidrogênio, halogênios, alquila, hidróxi, alcóxi, e outros substituintes. Um processo inclui prover um regioisómero da fórmula (III). em que Z é -CG^ 1^G^ 2^G^ 3^, (IV) ou (V):
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/575,344 US6201124B1 (en) | 1995-12-21 | 1995-12-21 | Process for production of piperidine derivatives |
PCT/US1996/020769 WO1997022344A1 (en) | 1995-12-21 | 1996-12-19 | Process for production of piperidine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
BR9612099A true BR9612099A (pt) | 1999-12-28 |
Family
ID=24299941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR9612099-1A BR9612099A (pt) | 1995-12-21 | 1996-12-19 | Processo para preparar um composto derivado de piperidina, regioisÈmero, processo para preparar um regioisÈmero, derivado de ácido 4-( alfa,alfa, di-substuìdo) toluico e 4- (alfa, alfa-di-não substitìdo) toluico. |
Country Status (16)
Country | Link |
---|---|
US (7) | US6201124B1 (pt) |
EP (2) | EP1362849A3 (pt) |
JP (2) | JP4865113B2 (pt) |
KR (2) | KR100591212B1 (pt) |
AT (1) | ATE335726T1 (pt) |
AU (1) | AU723759B2 (pt) |
BR (1) | BR9612099A (pt) |
CA (1) | CA2240735C (pt) |
DE (1) | DE69636439T2 (pt) |
DK (1) | DK0877733T3 (pt) |
ES (1) | ES2268715T3 (pt) |
HU (1) | HUP9900947A3 (pt) |
NO (1) | NO311718B1 (pt) |
NZ (1) | NZ326228A (pt) |
PT (1) | PT877733E (pt) |
WO (1) | WO1997022344A1 (pt) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2261207A1 (en) * | 1993-06-25 | 2010-12-15 | Aventisub II Inc. | Intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives |
US6153754A (en) * | 1995-12-21 | 2000-11-28 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
US6201124B1 (en) * | 1995-12-21 | 2001-03-13 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
ES2151442B1 (es) * | 1999-01-11 | 2001-07-01 | Espanola Prod Quimicos | Nuevo derivado del bencenoetanol. |
HUP0400299A2 (en) * | 2001-04-09 | 2007-08-28 | Teva Pharma | Polymorphs of fexofenadine hydrochloride |
US20030021849A1 (en) * | 2001-04-09 | 2003-01-30 | Ben-Zion Dolitzky | Polymorphs of fexofenadine hydrochloride |
ITRM20010260A1 (it) | 2001-05-17 | 2002-11-18 | Dinamite Dipharma S P A In For | Processo per la preparazione della fexofenadina o acido 4 1-idrossi-4-4- (idrossidifenilmetil)-1-piperidinil|-butil|-alfa,alfa-dimetilbenz |
AU2002357701A1 (en) * | 2001-11-08 | 2003-05-19 | Teva Pharmaceutical Industries Ltd. | Polymorphs of fexofenadine base |
ES2239554T1 (es) * | 2002-06-10 | 2005-10-01 | Teva Pharmaceutical Industries Ltd. | Forma xvi polimorfica de hidrocloruro de fexofenadina. |
US6949765B2 (en) | 2002-11-05 | 2005-09-27 | Chartered Semiconductor Manufacturing Ltd. | Padless structure design for easy identification of bridging defects in lines by passive voltage contrast |
TW200517114A (en) | 2003-10-15 | 2005-06-01 | Combinatorx Inc | Methods and reagents for the treatment of immunoinflammatory disorders |
JP2007532687A (ja) * | 2004-04-26 | 2007-11-15 | テバ ファーマシューティカル インダストリーズ リミティド | フェキソフェナジン塩酸塩の結晶形およびその製造方法 |
US7498345B2 (en) * | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
US7498443B2 (en) * | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of carebastine |
EP1685106A2 (en) * | 2004-09-28 | 2006-08-02 | Teva Pharmaceutical Industries, Inc. | Fexofendadine crystal form and processes for its preparation thereof |
EP1956906A4 (en) | 2005-11-09 | 2009-12-30 | Combinatorx Inc | METHODS, COMPOSITIONS AND KITS FOR THE TREATMENT OF PATHOLOGIES |
CN100443470C (zh) * | 2006-07-21 | 2008-12-17 | 杭州保灵有限公司 | 一种依巴斯汀的制备方法 |
ITMI20061491A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
ITMI20061492A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
ITMI20070987A1 (it) | 2007-05-16 | 2008-11-17 | Dipharma Francis Srl | Procedimento per la preparazione di composti chetonici |
WO2010021681A2 (en) * | 2008-08-18 | 2010-02-25 | Combinatorx (Singapore) Pte. Ltd. | Compositions and methods for treatment of viral diseases |
US20110130711A1 (en) * | 2009-11-19 | 2011-06-02 | Follica, Inc. | Hair growth treatment |
EP2371817A1 (en) * | 2010-04-01 | 2011-10-05 | Arevipharma GmbH | Process for the preparation of 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone and acid addition salts thereof |
CN105254579A (zh) * | 2015-09-19 | 2016-01-20 | 万全万特制药江苏有限公司 | 一种一锅法制备比拉斯汀中间体的方法 |
CN114621083A (zh) * | 2022-03-30 | 2022-06-14 | 西安万隆制药股份有限公司 | 一种抗组胺药物盐酸非索非那定杂质及其合成方法和应用 |
CN114671802B (zh) * | 2022-04-14 | 2024-05-17 | 江苏联环药业股份有限公司 | 一种高纯度依巴斯汀的制备方法 |
CN116375634A (zh) * | 2023-01-03 | 2023-07-04 | 成都施贝康生物医药科技有限公司 | 卡瑞斯汀对甲苯磺酸盐的晶型和无定型 |
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US4028404A (en) | 1967-07-31 | 1977-06-07 | Allen & Hanburys Limited | Acetic acid derivatives |
GB1242169A (en) | 1969-04-09 | 1971-08-11 | Ucb Sa | Piperidine derivatives |
US3839431A (en) | 1970-07-13 | 1974-10-01 | Squibb & Sons Inc | Cyclopropylmethylphenylacetic acids and derivatives |
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DD141422A5 (de) | 1978-01-27 | 1980-04-30 | Schering Ag | Verfahren zur herstellung von phenylessigsaeure-derivaten |
US4254129A (en) | 1979-04-10 | 1981-03-03 | Richardson-Merrell Inc. | Piperidine derivatives |
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US4285958A (en) | 1979-04-10 | 1981-08-25 | Richardson-Merrell Inc. | 1-Piperidine-alkylene ketones, pharmaceutical compositions thereof and method of use thereof |
US4285957A (en) | 1979-04-10 | 1981-08-25 | Richardson-Merrell Inc. | 1-Piperidine-alkanol derivatives, pharmaceutical compositions thereof, and method of use thereof |
GB8321157D0 (en) | 1983-08-05 | 1983-09-07 | Fordonal Sa | Piperidine derivatives |
US4742175A (en) | 1986-05-07 | 1988-05-03 | Merrell Dow Pharmaceuticals Inc. | Preparation of polymorphically pure terfenadine |
US5382600A (en) | 1988-01-22 | 1995-01-17 | Pharmacia Aktiebolag | 3,3-diphenylpropylamines and pharmaceutical compositions thereof |
FR2636946B1 (fr) | 1988-09-23 | 1990-11-02 | Lipha | ((diarylmethoxy)alcoyl)-1 pyrrolidines et piperidines, procedes de preparation et medicaments les contenant |
DE4034218A1 (de) | 1990-10-27 | 1992-04-30 | Merck Patent Gmbh | Verfahren zur herstellung von carebastin |
HU211019B (en) | 1991-12-02 | 1995-09-28 | Richter Gedeon Vegyeszet | Process for producing new 1,2,3,6-tetrahydropyridine and piperidine derivatives substituted with n-(hydroxylalkyl) group and compositions comprising such compounds |
HU226561B1 (en) | 1992-04-10 | 2009-04-28 | Merrell Dow Pharma | Process for preparation 4-diphenylmethyl piperidine derivatives and the novel intermediates thereof |
ES2284740T3 (es) | 1992-08-03 | 2007-11-16 | Sepracor Inc. | Carboxilato de terfenadina y el tratamiento de la irritacion cutanea. |
US20020007068A1 (en) * | 1999-07-16 | 2002-01-17 | D'ambra Thomas E. | Piperidine derivatives and process for their production |
DK1026147T3 (da) * | 1993-06-24 | 2004-03-22 | Albany Molecular Res Inc | Forbindelser, der er anvendelige som mellemprodukter i fremstillingen af piperidinderivater |
EP2261207A1 (en) * | 1993-06-25 | 2010-12-15 | Aventisub II Inc. | Intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives |
US6201124B1 (en) * | 1995-12-21 | 2001-03-13 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
US6153754A (en) * | 1995-12-21 | 2000-11-28 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
US5925761A (en) * | 1997-02-04 | 1999-07-20 | Sepracor Inc. | Synthesis of terfenadine and derivatives |
US7498345B2 (en) * | 2004-09-17 | 2009-03-03 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
-
1995
- 1995-12-21 US US08/575,344 patent/US6201124B1/en not_active Expired - Lifetime
-
1996
- 1996-12-19 NZ NZ326228A patent/NZ326228A/en not_active IP Right Cessation
- 1996-12-19 ES ES96945097T patent/ES2268715T3/es not_active Expired - Lifetime
- 1996-12-19 PT PT96945097T patent/PT877733E/pt unknown
- 1996-12-19 DK DK96945097T patent/DK0877733T3/da active
- 1996-12-19 HU HU9900947A patent/HUP9900947A3/hu unknown
- 1996-12-19 BR BR9612099-1A patent/BR9612099A/pt not_active IP Right Cessation
- 1996-12-19 AT AT96945097T patent/ATE335726T1/de active
- 1996-12-19 DE DE69636439T patent/DE69636439T2/de not_active Expired - Lifetime
- 1996-12-19 WO PCT/US1996/020769 patent/WO1997022344A1/en active IP Right Grant
- 1996-12-19 AU AU13547/97A patent/AU723759B2/en not_active Expired
- 1996-12-19 CA CA002240735A patent/CA2240735C/en not_active Expired - Lifetime
- 1996-12-19 EP EP03077248A patent/EP1362849A3/en not_active Withdrawn
- 1996-12-19 KR KR1020057009030A patent/KR100591212B1/ko not_active IP Right Cessation
- 1996-12-19 JP JP52309597A patent/JP4865113B2/ja not_active Expired - Lifetime
- 1996-12-19 EP EP96945097A patent/EP0877733B1/en not_active Expired - Lifetime
- 1996-12-19 KR KR10-1998-0704760A patent/KR100516869B1/ko not_active IP Right Cessation
-
1998
- 1998-06-18 NO NO19982806A patent/NO311718B1/no not_active IP Right Cessation
-
2000
- 2000-08-09 US US09/634,169 patent/US6452011B1/en not_active Expired - Lifetime
- 2000-08-09 US US09/634,775 patent/US6448406B1/en not_active Expired - Lifetime
-
2002
- 2002-08-05 US US10/212,854 patent/US6974872B2/en not_active Expired - Fee Related
-
2005
- 2005-05-06 US US11/123,275 patent/US7560561B2/en not_active Expired - Fee Related
-
2008
- 2008-09-04 JP JP2008227513A patent/JP2009019059A/ja active Pending
-
2009
- 2009-06-11 US US12/483,002 patent/US8022220B2/en not_active Expired - Fee Related
-
2011
- 2011-08-11 US US13/207,850 patent/US20110295014A1/en not_active Abandoned
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