AR031083A1 - UN COMPUESTO DERIVADO DE LA 4-PIRIDINIL-N-ACIL-L-FENILALANINA, SU USO, UNA COMPOSICION FARMACEUTICA QUE LO COMPRENDE, UN PROCEDIMIENTO PARA FABRICAR DICHA COMPOSICION, Y UN COMPUESTO uTIL COMO INTERMEDIO. - Google Patents
UN COMPUESTO DERIVADO DE LA 4-PIRIDINIL-N-ACIL-L-FENILALANINA, SU USO, UNA COMPOSICION FARMACEUTICA QUE LO COMPRENDE, UN PROCEDIMIENTO PARA FABRICAR DICHA COMPOSICION, Y UN COMPUESTO uTIL COMO INTERMEDIO.Info
- Publication number
- AR031083A1 AR031083A1 ARP000106416A ARP000106416A AR031083A1 AR 031083 A1 AR031083 A1 AR 031083A1 AR P000106416 A ARP000106416 A AR P000106416A AR P000106416 A ARP000106416 A AR P000106416A AR 031083 A1 AR031083 A1 AR 031083A1
- Authority
- AR
- Argentina
- Prior art keywords
- lower alkyl
- hydrogen
- aryl
- formula
- group
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Se describen compuestos de derivados de la 4-piridinil-N-acil-L-fenilalanina de formula (1) en la que R1 es un grupo de la formula Y-1 en la que R22 y R23, con independencia entre sí, son hidrogeno, alquilo inferior, alcoxi inferior, cicloalquilo, arilo, arilalquilo, nitro, ciano, (alquilo inferior)-tío, (alquilo inferior)-sulfinilo, (alquilo inferior)- sulfonilo, alcanoílo inferior, halogeno o perfluor-(alquilo inferior), y por lo menos uno de R22 y R23 es diferente del hidrogeno, y R24 es hidrogeno, alquilo inferior, alcoxi inferior, arilo, nitro, ciano, (alquilo inferior)ûsulfonilo o halogeno o bien R1 es un grupo de la formula Y-2 que es un anillo heteroaromático de cinco o seis eslabones, unido a través del átomo de carbono al carbonilo de la amida, dicho anillo contiene uno, dos o tres heteroátomos elegidos entre N, O y S y uno o dos átomos de dicho anillo están sustituidos con independencia entre sí por alquilo inferior, cicloalquilo, halogeno, ciano, perfluor-(alquilo inferior) o arilo y por lo menos uno de dichos átomos sustituidos está adyacente al átomo de carbono unido al carbonilo de la amida, o bien R1 es un grupo de la formula Y-3 que es un anillo de 3-7 eslabones en la que R25 es alquilo inferior, alquenilo inferior sin sustituir o sustituido con fluor, o un grupo de la formula R26-(CH2)e-, R26 es arilo, heteroarilo, azido, ciano, hidroxi, alcoxi inferior, (alcoxi inferior)-carbonilo, alcanoílo inferior, (alquilo inferior)-tío, (alquilo inferior) ûsulfonilo, (alquilo inferior)-sulfinilo, perfluor-(alcanoílo inferior), nitro o bien R26 es un grupo de la formula ûNR28R29, en la que R28 es hidrogeno o alquilo inferior, R29 es hidrogeno, alquilo inferior, (alcoxi inferior)-carbonilo, alcanoilo inferior, aroílo, perfluor-(alcanoílo inferior)-amino, (alquilo inferior) ûsulfonilo, (alquilo inferior)-aminocarbonilo, arilaminocarbonilo, o bien R28 y R29 junto con el átomo de nitrogeno al que están unidos forman un anillo heterocíclico saturado de 4, 5 o 6 eslabones que contiene un heteroátomo adicional, elegido entre O, S, y N-R40, Q es û(CH2)fO-, -(CH2)fS-, -(CH2)fN(R27)-, -(CH2)f-, R27 es H, alquilo inferior, arilo, alcanoílo inferior, aroílo o (alcoxi inferior)-carbonilo, R40 es H, alquilo inferior, arilo, alcanoílo inferior, aroílo o (alcoxi inferior)-carbonilo, los átomos de carbono del anillo están sin sustituir o sustituidos por alquilo inferior o halogeno, "e" es un numero entero de 0 a 4 y "f" es un numero entero de 0 a 3; R2 es hidrogeno o alquilo inferior, alquilo inferior sustituido, arilo o aril-(alquilo inferior); R3 es hidrogeno, halogeno, alquilo inferior o arilo y puede incluir además al trifluormetilo; R4 es hidrogeno, halogeno, alquilo inferior, o arilo; R5 es hidrogeno, alquilo inferior, alcoxi inferior, trifluormetilo u OH; R6 es hidrogeno, alquilo inferior, (alquilo inferior)-carboniloxi û (alquilo inferior) o bien R6 es un grupo de la formula P-3, en la que R32 es hidrogeno o alquilo inferior, R33 es hidrogeno, alquilo inferior o arilo, R34 es hidrogeno o alquilo inferior, "h" es un numero entero de 0 a 2, "g" es un numero entero de 0 a 2, la suma de h y g se situa entre 1 y 3; o bien R6 es un grupo de la formula P-4, en la que R32, g y h tienen los significados recién definidos , Q' es O, S, -(CH2)j û o un grupo de la formula N-R35, N35 es hidrogeno, alquilo inferior, alcanoílo inferior, (alcoxi inferior)-carbonilo, "j" es el numero 0, 1 o 2 y R7 es hidrogeno, cloro, alcoxi inferior o alquilo inferior; o bien las sales farmacéuticamente aceptables de los mismos. Estos compuestos son inhibidores de la union entre la molécula VCAM-1 y las células de expresion del antígeno VLA-4 y, por consiguiente, son utiles para el tratamiento de enfermedades cuyos síntomas y/o lesiones pueden atribuirse a la union de la molécula VCAM-1 con las células de expresion del VLA-4. En especial son utiles en el tratamiento de artritis reumatoidea, esclerosis multiple, enfermedades inflamatorias intestinales y asma. También se describen el uso del compuesto de formula (1) para fabricar un medicamento, una composicion farmacéutica que lo comprende, un procedimiento para fabricar una composicion farmacéutica y un compuesto util como intermedio.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16909099P | 1999-12-06 | 1999-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR031083A1 true AR031083A1 (es) | 2003-09-10 |
Family
ID=22614226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP000106416A AR031083A1 (es) | 1999-12-06 | 2000-12-04 | UN COMPUESTO DERIVADO DE LA 4-PIRIDINIL-N-ACIL-L-FENILALANINA, SU USO, UNA COMPOSICION FARMACEUTICA QUE LO COMPRENDE, UN PROCEDIMIENTO PARA FABRICAR DICHA COMPOSICION, Y UN COMPUESTO uTIL COMO INTERMEDIO. |
Country Status (34)
| Country | Link |
|---|---|
| EP (1) | EP1244625B1 (es) |
| JP (2) | JP2003516392A (es) |
| KR (1) | KR100492111B1 (es) |
| CN (1) | CN1196682C (es) |
| AR (1) | AR031083A1 (es) |
| AT (1) | ATE297895T1 (es) |
| AU (1) | AU779063B2 (es) |
| BR (1) | BR0016172A (es) |
| CA (1) | CA2392566A1 (es) |
| CO (1) | CO5080771A1 (es) |
| CZ (1) | CZ20022352A3 (es) |
| DE (1) | DE60020883T2 (es) |
| DK (1) | DK1244625T3 (es) |
| ES (1) | ES2243335T3 (es) |
| GC (1) | GC0000214A (es) |
| HK (1) | HK1053470A1 (es) |
| HR (1) | HRP20020467A2 (es) |
| HU (1) | HUP0203735A3 (es) |
| IL (2) | IL149622A0 (es) |
| JO (1) | JO2281B1 (es) |
| MA (1) | MA26849A1 (es) |
| MX (1) | MXPA02005240A (es) |
| MY (1) | MY128003A (es) |
| NO (1) | NO322910B1 (es) |
| NZ (1) | NZ518888A (es) |
| PE (1) | PE20010960A1 (es) |
| PL (1) | PL364814A1 (es) |
| PT (1) | PT1244625E (es) |
| RU (1) | RU2270193C2 (es) |
| TW (1) | TWI276629B (es) |
| UY (1) | UY26470A1 (es) |
| WO (1) | WO2001042215A1 (es) |
| YU (1) | YU40502A (es) |
| ZA (1) | ZA200203762B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6960597B2 (en) | 2000-06-30 | 2005-11-01 | Orth-Mcneil Pharmaceutical, Inc. | Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists |
| DE60143984D1 (de) | 2000-08-18 | 2011-03-17 | Ajinomoto Kk | Neue phenylalanin-derivate |
| WO2002028830A1 (fr) | 2000-09-29 | 2002-04-11 | Ajinomoto Co.,Inc. | Nouveaux derives de phenylalanine |
| EP1454898A4 (en) | 2001-12-13 | 2006-12-13 | Ajinomoto Kk | NEW PHENYL ALANIDE DERIVATIVES |
| US7998986B2 (en) | 2001-12-21 | 2011-08-16 | Exelixis Patent Company Llc | Modulators of LXR |
| US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| CN1917881B (zh) | 2003-12-22 | 2014-11-26 | 味之素株式会社 | 新型苯基丙氨酸衍生物 |
| US7618981B2 (en) * | 2004-05-06 | 2009-11-17 | Cytokinetics, Inc. | Imidazopyridinyl-benzamide anti-cancer agents |
| ATE430761T1 (de) * | 2004-08-16 | 2009-05-15 | Merck & Co Inc | Vla-4-antagonisten |
| JP4784224B2 (ja) | 2004-09-24 | 2011-10-05 | 味の素株式会社 | 糖鎖転移方法および糖鎖転移酵素 |
| JP2009531304A (ja) * | 2006-02-28 | 2009-09-03 | エラン ファーマシューティカルズ，インコーポレイテッド | α−４阻害剤化合物を用いて炎症性疾患および自己免疫疾患を治療する方法 |
| AR060901A1 (es) * | 2006-05-12 | 2008-07-23 | Jerini Ag | Compuestos heterociclicos para la inhibicion de integrinas y uso de estos |
| WO2008103378A2 (en) | 2007-02-20 | 2008-08-28 | Merrimack Pharmaceuticals, Inc. | Methods of treating multiple sclerosis by administration of alpha-fetoprotein in combination with an integrin antagonist |
| BRPI0911652A2 (pt) | 2008-04-11 | 2015-08-04 | Merrimack Pharmaceuticals Inc | Ligantes de albumina sérica humana e seus conjugados |
| ES2494465T3 (es) * | 2009-07-23 | 2014-09-15 | Bayer Cropscience Ag | Procedimiento para la preparación de alcoxienonas y enaminocetonas |
| US8877815B2 (en) | 2010-11-16 | 2014-11-04 | Novartis Ag | Substituted carbamoylcycloalkyl acetic acid derivatives as NEP |
| RU2624731C2 (ru) * | 2012-01-27 | 2017-07-06 | Ф. Хоффманн-Ля Рош Аг | Конъюгаты антагонистов интегрина для нацеленной доставки к клеткам, экспрессирующим vla-4 |
| JP6573604B2 (ja) * | 2013-06-11 | 2019-09-11 | セルジーン インターナショナル ツー エスエーアールエル | 新規なｇｌｐ−１レセプターモジュレーター |
| EA036432B1 (ru) | 2016-02-05 | 2020-11-10 | Эа Фарма Ко., Лтд. | Производные сульфонамида и содержащие их фармацевтические композиции |
| JP7214882B2 (ja) | 2018-10-30 | 2023-01-30 | ギリアード サイエンシーズ， インコーポレイテッド | アルファ４ベータ７インテグリン阻害剤としてのイミダゾピリジン誘導体 |
| US11179383B2 (en) | 2018-10-30 | 2021-11-23 | Gilead Sciences, Inc. | Compounds for inhibition of α4β7 integrin |
| JP7189368B2 (ja) | 2018-10-30 | 2022-12-13 | ギリアード サイエンシーズ， インコーポレイテッド | アルファ４ベータ７インテグリンの阻害のための化合物 |
| AU2019373240B2 (en) | 2018-10-30 | 2023-04-20 | Gilead Sciences, Inc. | Quinoline derivatives as alpha4beta7 integrin inhibitors |
| KR20220047323A (ko) | 2019-08-14 | 2022-04-15 | 길리애드 사이언시즈, 인코포레이티드 | 알파 4 베타 7 인테그린의 저해용 화합물 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002512625A (ja) * | 1997-05-29 | 2002-04-23 | メルク エンド カンパニー インコーポレーテッド | 細胞接着阻害薬としての複素環アミド化合物 |
| AU726585B2 (en) * | 1997-05-29 | 2000-11-09 | Merck & Co., Inc. | Biarylalkanoic acids as cell adhesion inhibitors |
| US6197794B1 (en) * | 1998-01-08 | 2001-03-06 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| MY153569A (en) * | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
| US6329372B1 (en) * | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| ES2226413T3 (es) * | 1998-02-26 | 2005-03-16 | Celltech Therapeutics Limited | Derivados de fenilalanina como inhibidores de alfa-4 integrinas. |
| GB9811159D0 (en) * | 1998-05-22 | 1998-07-22 | Celltech Therapeutics Ltd | Chemical compounds |
| ES2220140T3 (es) * | 1998-12-22 | 2004-12-01 | Tanabe Seiyaku Co., Ltd. | Inhibidores de la adhesion mediada de celulas por alfa 4 beta 1 (a4b1). |
| DE60021251D1 (de) * | 1999-01-22 | 2005-08-18 | Elan Pharm Inc | Multizyklische verbindungen zur hemmung der durch vla-4 vermittelten leukozytenadhäsion |
-
2000
- 2000-11-29 EP EP00985117A patent/EP1244625B1/en not_active Expired - Lifetime
- 2000-11-29 ES ES00985117T patent/ES2243335T3/es not_active Expired - Lifetime
- 2000-11-29 HU HU0203735A patent/HUP0203735A3/hu unknown
- 2000-11-29 YU YU40502A patent/YU40502A/sh unknown
- 2000-11-29 DE DE60020883T patent/DE60020883T2/de not_active Expired - Lifetime
- 2000-11-29 BR BR0016172-1A patent/BR0016172A/pt not_active Application Discontinuation
- 2000-11-29 IL IL14962200A patent/IL149622A0/xx active IP Right Grant
- 2000-11-29 WO PCT/EP2000/011979 patent/WO2001042215A1/en active IP Right Grant
- 2000-11-29 RU RU2002117419/04A patent/RU2270193C2/ru not_active IP Right Cessation
- 2000-11-29 AT AT00985117T patent/ATE297895T1/de not_active IP Right Cessation
- 2000-11-29 PT PT00985117T patent/PT1244625E/pt unknown
- 2000-11-29 JP JP2001543516A patent/JP2003516392A/ja active Pending
- 2000-11-29 KR KR10-2002-7007201A patent/KR100492111B1/ko not_active IP Right Cessation
- 2000-11-29 CZ CZ20022352A patent/CZ20022352A3/cs unknown
- 2000-11-29 CA CA002392566A patent/CA2392566A1/en not_active Abandoned
- 2000-11-29 JO JO2000189A patent/JO2281B1/en active
- 2000-11-29 PL PL00364814A patent/PL364814A1/xx not_active Application Discontinuation
- 2000-11-29 CN CNB008164800A patent/CN1196682C/zh not_active Expired - Fee Related
- 2000-11-29 DK DK00985117T patent/DK1244625T3/da active
- 2000-11-29 MX MXPA02005240A patent/MXPA02005240A/es active IP Right Grant
- 2000-11-29 AU AU21639/01A patent/AU779063B2/en not_active Ceased
- 2000-11-29 NZ NZ518888A patent/NZ518888A/en unknown
- 2000-12-02 GC GCP20001072 patent/GC0000214A/en active
- 2000-12-04 MY MYPI20005689A patent/MY128003A/en unknown
- 2000-12-04 AR ARP000106416A patent/AR031083A1/es not_active Application Discontinuation
- 2000-12-05 CO CO00092690A patent/CO5080771A1/es unknown
- 2000-12-05 TW TW089125889A patent/TWI276629B/zh not_active IP Right Cessation
- 2000-12-05 UY UY26470A patent/UY26470A1/es not_active Application Discontinuation
- 2000-12-06 PE PE2000001306A patent/PE20010960A1/es not_active Application Discontinuation
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2002
- 2002-05-10 ZA ZA200203762A patent/ZA200203762B/xx unknown
- 2002-05-13 IL IL149622A patent/IL149622A/en not_active IP Right Cessation
- 2002-05-28 HR HR20020467A patent/HRP20020467A2/xx not_active Application Discontinuation
- 2002-06-05 NO NO20022650A patent/NO322910B1/no unknown
- 2002-06-05 MA MA26672A patent/MA26849A1/fr unknown
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2003
- 2003-08-13 HK HK03105803A patent/HK1053470A1/xx not_active IP Right Cessation
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2007
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