ZA200306599B - Methods for preparing CETP inhibitors. - Google Patents
Methods for preparing CETP inhibitors. Download PDFInfo
- Publication number
- ZA200306599B ZA200306599B ZA200306599A ZA200306599A ZA200306599B ZA 200306599 B ZA200306599 B ZA 200306599B ZA 200306599 A ZA200306599 A ZA 200306599A ZA 200306599 A ZA200306599 A ZA 200306599A ZA 200306599 B ZA200306599 B ZA 200306599B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- viia
- trifluoromethyl
- prepared
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 46
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 123
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- -1 3,5-bis(trifluoromethyl)benzyl halide Chemical class 0.000 claims description 12
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- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 230000003301 hydrolyzing effect Effects 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
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- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- 230000002596 correlated effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- AKCRYMMHDRQANK-SNVBAGLBSA-N methyl n-[(3r)-3-[4-(trifluoromethyl)anilino]pentanoyl]carbamate Chemical compound COC(=O)NC(=O)C[C@@H](CC)NC1=CC=C(C(F)(F)F)C=C1 AKCRYMMHDRQANK-SNVBAGLBSA-N 0.000 description 3
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- 238000006467 substitution reaction Methods 0.000 description 1
- ZOYXDRDJRPCCTD-UHFFFAOYSA-N tert-butyl n-(1-cyanobutan-2-yl)carbamate Chemical compound N#CCC(CC)NC(=O)OC(C)(C)C ZOYXDRDJRPCCTD-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 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)
- Obesity (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (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)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28752201P | 2001-04-30 | 2001-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200306599B true ZA200306599B (en) | 2004-10-22 |
Family
ID=23103272
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200306599A ZA200306599B (en) | 2001-04-30 | 2003-08-25 | Methods for preparing CETP inhibitors. |
| ZA200306600A ZA200306600B (en) | 2001-04-30 | 2003-08-25 | Compounds useful as intermediates for 4-aminoquinoline derivatives. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200306600A ZA200306600B (en) | 2001-04-30 | 2003-08-25 | Compounds useful as intermediates for 4-aminoquinoline derivatives. |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US6600045B2 (pt) |
| EP (2) | EP1425270B1 (pt) |
| JP (2) | JP3924250B2 (pt) |
| KR (2) | KR100639745B1 (pt) |
| CN (3) | CN100357265C (pt) |
| AR (3) | AR036331A1 (pt) |
| AT (2) | ATE321755T1 (pt) |
| AU (1) | AU2002253448B2 (pt) |
| BR (2) | BR0209238A (pt) |
| CA (2) | CA2445693A1 (pt) |
| CZ (2) | CZ20032898A3 (pt) |
| DE (2) | DE60210265T2 (pt) |
| DK (2) | DK1383734T3 (pt) |
| ES (2) | ES2259080T3 (pt) |
| HK (1) | HK1062294A1 (pt) |
| HU (2) | HU225777B1 (pt) |
| IL (2) | IL157544A0 (pt) |
| MX (2) | MXPA03009936A (pt) |
| PL (2) | PL366584A1 (pt) |
| PT (1) | PT1425270E (pt) |
| RU (2) | RU2265010C2 (pt) |
| TW (1) | TWI250974B (pt) |
| WO (2) | WO2002088085A2 (pt) |
| YU (2) | YU84303A (pt) |
| ZA (2) | ZA200306599B (pt) |
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 |
| MXPA05003456A (es) | 2002-10-04 | 2005-07-05 | Millennium Pharm Inc | Antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias. |
| US7504508B2 (en) | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| DE60323536D1 (de) | 2002-12-20 | 2008-10-23 | Pfizer Prod Inc | Dosierungsform enthaltend einen cetp-hemmer und einen hmg-coa reduktase hemmer |
| JP4644658B2 (ja) * | 2003-02-18 | 2011-03-02 | 高砂香料工業株式会社 | 光学活性テトラヒドロキノリン類の製造方法 |
| MXPA05009331A (es) * | 2003-03-17 | 2005-11-04 | Kaneka Corp | Metodo para producir un derivado de amida del acido (r)-3-[4-(trifluorometil)fenilamino]-pentanoico. |
| US7223859B2 (en) | 2003-03-17 | 2007-05-29 | Pfizer Inc. | Method for producing (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoic acid amide derivative |
| SG146695A1 (en) | 2003-09-26 | 2008-10-30 | Japan Tobacco Inc | Method of inhibiting remnant lipoprotein production |
| 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 |
| ATE428411T1 (de) * | 2003-11-07 | 2009-05-15 | Jj Pharma Inc | Hdl-verstärkende kombinationstherapie-komplexe |
| MXPA06011540A (es) * | 2004-04-07 | 2007-01-26 | Millennium Pharm Inc | Antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias. |
| US20080269284A1 (en) * | 2004-06-24 | 2008-10-30 | Eli Lilly And Company | Compounds and Methods for Treating Dyslipidemia |
| DE102004031656A1 (de) * | 2004-06-30 | 2006-01-19 | Merck Patent Gmbh | Tetrahydrochinoline |
| US7700774B2 (en) * | 2004-12-20 | 2010-04-20 | Dr. Reddy's Laboratories Ltd. | Heterocyclic compounds and their pharmaceutical compositions |
| JP2008543726A (ja) | 2005-02-24 | 2008-12-04 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 炎症性疾患の処置のためのｐｇｄ２受容体アンタゴニスト |
| EP1896402A4 (en) * | 2005-06-20 | 2010-07-28 | Astrazeneca Ab | PROCESS FOR THE SYNTHESIS OF (ALKOXYCARBONYLAMINO) ALKYLSULFONATES |
| TW200808731A (en) | 2006-03-30 | 2008-02-16 | Tanabe Seiyaku Co | A process for preparing tetrahydroquinoline derivatives |
| DE102006031151A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
| DE102006031149A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
| DE102006031143A1 (de) * | 2006-07-04 | 2008-01-24 | Merck Patent Gmbh | Fluortenside |
| DE102006032391A1 (de) * | 2006-07-04 | 2008-01-17 | Merck Patent Gmbh | Fluortenside |
| DE102006031262A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
| CL2008000684A1 (es) | 2007-03-09 | 2008-08-01 | Indigene Pharmaceuticals Inc | Composicion farmaceutica que comprende metformina r-(+) lipoato y un inhibidor de reductasa hmg-coa; formulacion de dosis unitaria; y uso en el tratamiento de una complicacion diabetica. |
| 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 |
| TWI450896B (zh) * | 2009-06-30 | 2014-09-01 | Lilly Co Eli | 反式－４－〔〔（５ｓ）－５－〔〔〔３，５－雙（三氟甲基）苯基〕甲基〕（２－甲基－２ｈ－四唑－５－基）胺基〕－２，３，４，５－四氫－７，９－二甲基－１ｈ－１－苯并氮呯－１－基〕甲基〕－環己基羧酸 |
| DK2697207T3 (en) | 2011-04-12 | 2017-03-27 | Chong Kun Dang Pharmaceutical Corp | 3- (2-ARYL-CYCLOALKENYLMETHYL) -OXAZOLIDIN-2-ON DERIVATIVES AS CHOLESTEROL ESTER-TRANSFER PROTEIN (CETP) INHIBITORS |
| TWI627167B (zh) | 2011-07-08 | 2018-06-21 | 諾華公司 | 用於高三酸甘油酯個體治療動脈粥狀硬化之方法 |
| NZ708079A (en) | 2013-01-31 | 2016-07-29 | Chong Kun Dang Pharm Corp | Biaryl- or heterocyclic biaryl-substituted cyclohexene derivative compounds as cetp inhibitors |
| JP2016535726A (ja) * | 2013-11-11 | 2016-11-17 | ロンザ・リミテッド | ルイス酸を用いて第１３族のシアノ化合物を調製するための方法 |
| BR112017002873B1 (pt) * | 2014-08-12 | 2023-03-28 | Newamsterdam Pharma B.V. | Processo para preparar intermediários sintéticos para preparar derivados de tetra-hidroquinolina |
| 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 |
|---|---|---|---|---|
| JP5035813B2 (ja) | 1998-07-10 | 2012-09-26 | マサチューセッツ インスティテュート オブ テクノロジー | 金属用のリガンドおよびそれらに基づいて改善された金属触媒法 |
| 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 |
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2002
- 2002-04-08 RU RU2003131871/04A patent/RU2265010C2/ru not_active IP Right Cessation
- 2002-04-08 DE DE60210265T patent/DE60210265T2/de not_active Expired - Fee Related
- 2002-04-08 PT PT02722567T patent/PT1425270E/pt unknown
- 2002-04-08 AU AU2002253448A patent/AU2002253448B2/en not_active Ceased
- 2002-04-08 KR KR1020037014134A patent/KR100639745B1/ko not_active IP Right Cessation
- 2002-04-08 WO PCT/IB2002/001214 patent/WO2002088085A2/en active IP Right Grant
- 2002-04-08 ES ES02722567T patent/ES2259080T3/es not_active Expired - Lifetime
- 2002-04-08 DK DK02722569T patent/DK1383734T3/da active
- 2002-04-08 MX MXPA03009936A patent/MXPA03009936A/es active IP Right Grant
- 2002-04-08 CZ CZ20032898A patent/CZ20032898A3/cs unknown
- 2002-04-08 KR KR1020037014135A patent/KR100591998B1/ko not_active IP Right Cessation
- 2002-04-08 HU HU0304041A patent/HU225777B1/hu not_active IP Right Cessation
- 2002-04-08 CN CNB2005100529529A patent/CN100357265C/zh not_active Expired - Fee Related
- 2002-04-08 BR BR0209238-7A patent/BR0209238A/pt not_active IP Right Cessation
- 2002-04-08 HU HU0304039A patent/HUP0304039A3/hu unknown
- 2002-04-08 AT AT02722567T patent/ATE321755T1/de not_active IP Right Cessation
- 2002-04-08 YU YU84303A patent/YU84303A/sh unknown
- 2002-04-08 MX MXPA03009935A patent/MXPA03009935A/es active IP Right Grant
- 2002-04-08 DK DK02722567T patent/DK1425270T3/da active
- 2002-04-08 DE DE60209004T patent/DE60209004T2/de not_active Expired - Fee Related
- 2002-04-08 CA CA002445693A patent/CA2445693A1/en not_active Abandoned
- 2002-04-08 WO PCT/IB2002/001217 patent/WO2002088069A2/en active IP Right Grant
- 2002-04-08 IL IL15754402A patent/IL157544A0/xx unknown
- 2002-04-08 EP EP02722567A patent/EP1425270B1/en not_active Expired - Lifetime
- 2002-04-08 CZ CZ20032900A patent/CZ20032900A3/cs unknown
- 2002-04-08 JP JP2002585373A patent/JP3924250B2/ja not_active Expired - Fee Related
- 2002-04-08 RU RU2003131870/04A patent/RU2259355C2/ru not_active IP Right Cessation
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- 2002-04-08 CN CNB028091442A patent/CN1297541C/zh not_active Expired - Fee Related
- 2002-04-08 ES ES02722569T patent/ES2256461T3/es not_active Expired - Lifetime
- 2002-04-08 CN CNB028091663A patent/CN1267411C/zh not_active Expired - Fee Related
- 2002-04-08 EP EP02722569A patent/EP1383734B1/en not_active Expired - Lifetime
- 2002-04-08 BR BR0209291-3A patent/BR0209291A/pt not_active IP Right Cessation
- 2002-04-08 PL PL02366584A patent/PL366584A1/xx not_active Application Discontinuation
- 2002-04-08 JP JP2002585387A patent/JP3924251B2/ja not_active Expired - Fee Related
- 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 AT AT02722569T patent/ATE316957T1/de not_active IP Right Cessation
- 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 US10/136,758 patent/US6600045B2/en not_active Expired - Fee Related
- 2002-04-30 US US10/137,314 patent/US6689897B2/en not_active Expired - Fee Related
-
2003
- 2003-04-18 US US10/418,821 patent/US6706881B2/en not_active Expired - Fee Related
- 2003-08-25 ZA ZA200306599A patent/ZA200306599B/en unknown
- 2003-08-25 ZA ZA200306600A patent/ZA200306600B/en unknown
-
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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