RU2003131871A - Соединения, используемые в качестве промежуточных соединений - Google Patents
Соединения, используемые в качестве промежуточных соединений Download PDFInfo
- Publication number
- RU2003131871A RU2003131871A RU2003131871/04A RU2003131871A RU2003131871A RU 2003131871 A RU2003131871 A RU 2003131871A RU 2003131871/04 A RU2003131871/04 A RU 2003131871/04A RU 2003131871 A RU2003131871 A RU 2003131871A RU 2003131871 A RU2003131871 A RU 2003131871A
- Authority
- RU
- Russia
- Prior art keywords
- compound
- formula
- compounds
- benzyl
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000003446 ligand Substances 0.000 claims 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- -1 trifluoromethylbenzene compound Chemical class 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical group [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
- C07C271/64—Y being a hydrogen or a carbon atom, e.g. benzoylcarbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (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)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Claims (15)
1. Соединение формулы III,
2. Соединение формулы IV,
3. Соединение формулы VI,
где R выбирают из метила, бензила и замещенного бензила.
4. Соединение формулы VII,
где R выбирают из метила, бензила и замещенного бензила.
5. Соединение по п.3 или 4, где R выбирают из метила, бензила и бензила, замещенного одним или несколькими заместителями, каждый из которых независимо выбирают из (C1-C3)-алкила, (C1-C3)-алкилокси и галогена.
6. Способ получения соединения формулы III,
включающий сочетание трифторметилбензола, пара-замещенного галогеном или O-трифлатом, с соединением формулы II,
с образованием соединения формулы III.
7. Способ по п.6, где указанное соединение трифторметилбензола присоединяют к указанному соединению формулы II в присутствии фосфинового лиганда.
8. Способ по п.7, где указанный фосфиновый лиганд означает диалкилфосфинодифениловый лиганд.
9. Способ по п.8, где указанный фосфиновый лиганд выбирают из 2-дициклогексилфосфино-2'-(N,N-диметиламино)дифенила и 2-дициклогексилфосфино-2'-метилдифенила.
10. Способ по п.6, где указанное сочетание включает присоединение указанного соединения трифторметилбензола к указанному соединению формулы II в присутствии основания.
11. Способ получения соединения формулы IV,
включающий гидролиз соединения формулы III,
гидролизующим агентом, выбираемым из кислоты и основания, с образованием соединения формулы IV.
12. Способ получения соединения формулы VI,
включающий присоединение соединения формулы IV,
к соединению формулы V,
где R выбирают из метила, бензила и замещенного бензила, в присутствии основания, с образованием соединений формулы VI.
13. Способ по п.12, где указанное основание представляет собой трет-бутилат лития.
14. Способ получения соединения формулы VII.
включающий восстановление соединения формулы VI,
где R выбирают из метила, бензила и замещенного бензила, восстановителем с получением восстановленного соединения и циклизацию восстановленного соединения в кислотных условиях с получением соединения формулы VII.
15. Способ по п.14, где указанный восстановитель представляет собой борогидрид натрия в присутствии кислоты Льюиса.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28752201P | 2001-04-30 | 2001-04-30 | |
| US60/287,522 | 2001-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003131871A true RU2003131871A (ru) | 2005-04-10 |
| RU2265010C2 RU2265010C2 (ru) | 2005-11-27 |
Family
ID=23103272
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003131871/04A RU2265010C2 (ru) | 2001-04-30 | 2002-04-08 | Промежуточные соединения для ингибиторов cetp и способы их получения |
| RU2003131870/04A RU2259355C2 (ru) | 2001-04-30 | 2002-04-08 | Способ получения ингибитора сетр, промежуточное вещество и способ его получения |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003131870/04A RU2259355C2 (ru) | 2001-04-30 | 2002-04-08 | Способ получения ингибитора сетр, промежуточное вещество и способ его получения |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US6689897B2 (ru) |
| EP (2) | EP1383734B1 (ru) |
| JP (2) | JP3924250B2 (ru) |
| KR (2) | KR100639745B1 (ru) |
| CN (3) | CN100357265C (ru) |
| AR (3) | AR036331A1 (ru) |
| AT (2) | ATE321755T1 (ru) |
| AU (1) | AU2002253448B2 (ru) |
| BR (2) | BR0209291A (ru) |
| CA (2) | CA2445623A1 (ru) |
| CZ (2) | CZ20032898A3 (ru) |
| DE (2) | DE60210265T2 (ru) |
| DK (2) | DK1383734T3 (ru) |
| ES (2) | ES2256461T3 (ru) |
| HK (1) | HK1062294A1 (ru) |
| HU (2) | HUP0304039A3 (ru) |
| IL (2) | IL157544A0 (ru) |
| MX (2) | MXPA03009935A (ru) |
| PL (2) | PL366700A1 (ru) |
| PT (1) | PT1425270E (ru) |
| RU (2) | RU2265010C2 (ru) |
| TW (1) | TWI250974B (ru) |
| WO (2) | WO2002088069A2 (ru) |
| YU (2) | YU84303A (ru) |
| ZA (2) | ZA200306600B (ru) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6197786B1 (en) * | 1998-09-17 | 2001-03-06 | Pfizer Inc | 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines |
| US20040002615A1 (en) * | 2002-06-28 | 2004-01-01 | Allen David Robert | Preparation of chiral amino-nitriles |
| JP2006021999A (ja) * | 2002-07-12 | 2006-01-26 | Kaneka Corp | 光学活性β−アミノニトリル化合物およびその対掌体アミド化合物の製造方法 |
| US20090181966A1 (en) * | 2002-10-04 | 2009-07-16 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| US7504508B2 (en) | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| AU2003277285B2 (en) | 2002-10-04 | 2007-12-13 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| ATE461700T1 (de) | 2002-12-20 | 2010-04-15 | Pfizer Prod Inc | Dosierungsform enthaltend einen cetp-hemmer und einen hmg-coa reduktase hemmer |
| WO2004074255A2 (en) * | 2003-02-18 | 2004-09-02 | Takasago International Corporation | Method for producing an optically active tetrahydroquinoline |
| US7223859B2 (en) | 2003-03-17 | 2007-05-29 | Pfizer Inc. | Method for producing (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoic acid amide derivative |
| EP1604975A4 (en) * | 2003-03-17 | 2006-11-02 | Kaneka Corp | PROCESSES FOR PRODUCING (R) -3- 4- (TRIFLUOROMETHYL) -PHENYLAMINO-PENTANAMIDE DERIVATIVES |
| MXPA06003357A (es) | 2003-09-26 | 2006-06-08 | Japan Tobacco Inc | Metodo para inhibir la produccion de lipoproteina remanente. |
| JP4773969B2 (ja) * | 2003-10-08 | 2011-09-14 | イーライ リリー アンド カンパニー | 脂質代謝異常の治療ための化合物及び方法 |
| DE602004020649D1 (de) * | 2003-11-07 | 2009-05-28 | Jj Pharma Inc | Hdl-verstärkende kombinationstherapie-komplexe |
| CN101018770A (zh) * | 2004-04-07 | 2007-08-15 | 千禧药品公司 | 炎性疾病治疗用pgd2受体拮抗剂 |
| MXPA06014716A (es) * | 2004-06-24 | 2007-03-12 | Lilly Co Eli | Compuestos y metodos para el tratamiento de dislipidemia. |
| DE102004031656A1 (de) * | 2004-06-30 | 2006-01-19 | Merck Patent Gmbh | Tetrahydrochinoline |
| WO2006069162A1 (en) * | 2004-12-20 | 2006-06-29 | Reddy Us Therapeutics, Inc. | Novel heterocyclic compounds and their pharmaceutical compositions |
| UA90706C2 (ru) | 2005-02-24 | 2010-05-25 | Милленниум Фармасьютикалз, Инк. | Антагонисты рецептора pgd2 для лечения воспалительных заболеваний |
| KR20080016933A (ko) * | 2005-06-20 | 2008-02-22 | 아스트라제네카 아베 | (알콕시카보닐아미노)알킬 설포네이트의 제조 방법 |
| UY30244A1 (es) | 2006-03-30 | 2007-11-30 | Tanabe Seiyaku Co | Un proceso para preparar derivados de tetrahidroquinolina |
| DE102006031149A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
| DE102006032391A1 (de) * | 2006-07-04 | 2008-01-17 | Merck Patent Gmbh | Fluortenside |
| DE102006031151A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
| DE102006031143A1 (de) * | 2006-07-04 | 2008-01-24 | Merck Patent Gmbh | Fluortenside |
| DE102006031262A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
| TW200901959A (en) | 2007-03-09 | 2009-01-16 | Indigene Pharmaceuticals Inc | Combination of metformin R-(+) lipoate and antihyperlipidemic agents for the treatment of diabetic hyperglycemia and diabetic complications |
| JP2011256110A (ja) * | 2008-09-30 | 2011-12-22 | Takeda Chem Ind Ltd | ヘキサヒドロピロロキノリンの製造法 |
| AR077208A1 (es) | 2009-06-30 | 2011-08-10 | Lilly Co Eli | Derivados del acido trans-4-[[(5s)-5-[[[3,5-bis(trifluorometil) fenil] metil] (2-metil-2h-tetrazol-5-il) amino) -2,3,4,5-tetrahidro-7,9-dimetil-1h-1-benzazepin-1-il) metil)-ciclohexancarboxilico y sus formas cristalinas, composiciones farmaceuticas que los comprenden, su uso para preparar un medicam |
| US9371294B2 (en) | 2011-04-12 | 2016-06-21 | Chong Kun Dang Pharmaceutical Corp. | Cycloalkenyl aryl derivatives for CETP inhibitor |
| BR112014000333A2 (pt) | 2011-07-08 | 2017-02-07 | Novartis Ag | método de tratamento de aterosclerose em sujeitos com triglicerídeo alto |
| NZ708079A (en) | 2013-01-31 | 2016-07-29 | Chong Kun Dang Pharm Corp | Biaryl- or heterocyclic biaryl-substituted cyclohexene derivative compounds as cetp inhibitors |
| EP3039740B1 (en) * | 2013-11-11 | 2016-11-09 | Lonza Ltd | Method for preparation of cyano compounds of the 13th group with a lewis acid |
| EP4083022A1 (en) * | 2014-08-12 | 2022-11-02 | NewAmsterdam Pharma B.V. | Process for preparing synthetic intermediates for preparing tetrahydroquinoline derivatives |
| CN105294559B (zh) * | 2015-06-24 | 2017-11-14 | 厦门法茉维特动物药业有限公司 | 一种医药中间体4‑氨基喹啉类化合物的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1097158B1 (en) | 1998-07-10 | 2006-01-25 | Massachusetts Institute Of Technology | Ligands for metals and metal-catalyzed processes |
| GT199900147A (es) * | 1998-09-17 | 1999-09-06 | 1, 2, 3, 4- tetrahidroquinolinas 2-sustituidas 4-amino sustituidas. | |
| US6197786B1 (en) | 1998-09-17 | 2001-03-06 | Pfizer Inc | 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines |
-
2002
- 2002-04-08 JP JP2002585373A patent/JP3924250B2/ja not_active Expired - Fee Related
- 2002-04-08 IL IL15754402A patent/IL157544A0/xx unknown
- 2002-04-08 WO PCT/IB2002/001217 patent/WO2002088069A2/en active IP Right Grant
- 2002-04-08 RU RU2003131871/04A patent/RU2265010C2/ru not_active IP Right Cessation
- 2002-04-08 ES ES02722569T patent/ES2256461T3/es not_active Expired - Lifetime
- 2002-04-08 MX MXPA03009935A patent/MXPA03009935A/es active IP Right Grant
- 2002-04-08 CZ CZ20032898A patent/CZ20032898A3/cs unknown
- 2002-04-08 BR BR0209291-3A patent/BR0209291A/pt not_active IP Right Cessation
- 2002-04-08 DE DE60210265T patent/DE60210265T2/de not_active Expired - Fee Related
- 2002-04-08 YU YU84303A patent/YU84303A/sh unknown
- 2002-04-08 ES ES02722567T patent/ES2259080T3/es not_active Expired - Lifetime
- 2002-04-08 PL PL02366700A patent/PL366700A1/xx not_active Application Discontinuation
- 2002-04-08 CA CA002445623A patent/CA2445623A1/en not_active Abandoned
- 2002-04-08 DK DK02722569T patent/DK1383734T3/da active
- 2002-04-08 DE DE60209004T patent/DE60209004T2/de not_active Expired - Fee Related
- 2002-04-08 HU HU0304039A patent/HUP0304039A3/hu unknown
- 2002-04-08 DK DK02722567T patent/DK1425270T3/da active
- 2002-04-08 IL IL15754602A patent/IL157546A0/xx unknown
- 2002-04-08 EP EP02722569A patent/EP1383734B1/en not_active Expired - Lifetime
- 2002-04-08 KR KR1020037014134A patent/KR100639745B1/ko not_active IP Right Cessation
- 2002-04-08 BR BR0209238-7A patent/BR0209238A/pt not_active IP Right Cessation
- 2002-04-08 MX MXPA03009936A patent/MXPA03009936A/es active IP Right Grant
- 2002-04-08 CN CNB2005100529529A patent/CN100357265C/zh not_active Expired - Fee Related
- 2002-04-08 PT PT02722567T patent/PT1425270E/pt unknown
- 2002-04-08 CN CNB028091442A patent/CN1297541C/zh not_active Expired - Fee Related
- 2002-04-08 JP JP2002585387A patent/JP3924251B2/ja not_active Expired - Fee Related
- 2002-04-08 CN CNB028091663A patent/CN1267411C/zh not_active Expired - Fee Related
- 2002-04-08 CA CA002445693A patent/CA2445693A1/en not_active Abandoned
- 2002-04-08 RU RU2003131870/04A patent/RU2259355C2/ru not_active IP Right Cessation
- 2002-04-08 AU AU2002253448A patent/AU2002253448B2/en not_active Ceased
- 2002-04-08 AT AT02722567T patent/ATE321755T1/de not_active IP Right Cessation
- 2002-04-08 CZ CZ20032900A patent/CZ20032900A3/cs unknown
- 2002-04-08 AT AT02722569T patent/ATE316957T1/de not_active IP Right Cessation
- 2002-04-08 WO PCT/IB2002/001214 patent/WO2002088085A2/en active IP Right Grant
- 2002-04-08 KR KR1020037014135A patent/KR100591998B1/ko not_active IP Right Cessation
- 2002-04-08 PL PL02366584A patent/PL366584A1/xx not_active Application Discontinuation
- 2002-04-08 HU HU0304041A patent/HU225777B1/hu not_active IP Right Cessation
- 2002-04-08 YU YU84403A patent/YU84403A/sh unknown
- 2002-04-08 EP EP02722567A patent/EP1425270B1/en not_active Expired - Lifetime
- 2002-04-24 TW TW091108446A patent/TWI250974B/zh not_active IP Right Cessation
- 2002-04-29 AR ARP020101576A patent/AR036331A1/es unknown
- 2002-04-29 AR ARP020101575A patent/AR035963A1/es unknown
- 2002-04-30 US US10/137,314 patent/US6689897B2/en not_active Expired - Fee Related
- 2002-04-30 US US10/136,758 patent/US6600045B2/en not_active Expired - Fee Related
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2003
- 2003-04-18 US US10/418,821 patent/US6706881B2/en not_active Expired - Fee Related
- 2003-08-25 ZA ZA200306600A patent/ZA200306600B/en unknown
- 2003-08-25 ZA ZA200306599A patent/ZA200306599B/en unknown
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2004
- 2004-06-15 AR ARP040102071A patent/AR044706A2/es not_active Application Discontinuation
- 2004-07-19 HK HK04105255A patent/HK1062294A1/xx not_active IP Right Cessation
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