ES2194545T3 - Metodo para la preparacion de citolopram. - Google Patents
Metodo para la preparacion de citolopram.Info
- Publication number
- ES2194545T3 ES2194545T3 ES99968622T ES99968622T ES2194545T3 ES 2194545 T3 ES2194545 T3 ES 2194545T3 ES 99968622 T ES99968622 T ES 99968622T ES 99968622 T ES99968622 T ES 99968622T ES 2194545 T3 ES2194545 T3 ES 2194545T3
- Authority
- ES
- Spain
- Prior art keywords
- preparation
- citolopram
- palladium catalyst
- citalopram
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 2
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229960001653 citalopram Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- 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
- A61P25/24—Antidepressants
-
- 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]
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Materials Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
Abstract
Método para la preparación de citalopram, que comprende la reacción de un compuesto de Fórmula (IV), en donde R es halógeno, o -CF3 -(CF2) -SO2-, siendo n O a 8, con una fuente de cianuro, en presencia de un catalizador de paladio y una cantidad catalitica de Cu 0 Zn2+, o con Zn(CN)2 en presencia de un catalizador de paladio.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA199900920 | 1999-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2194545T3 true ES2194545T3 (es) | 2003-11-16 |
Family
ID=8099035
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200150011A Withdrawn ES2189699A1 (es) | 1999-06-25 | 1999-11-22 | Metodo de preparacion de citalopram. |
| ES99968622T Expired - Lifetime ES2194545T3 (es) | 1999-06-25 | 1999-11-22 | Metodo para la preparacion de citolopram. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200150011A Withdrawn ES2189699A1 (es) | 1999-06-25 | 1999-11-22 | Metodo de preparacion de citalopram. |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US20020077353A1 (es) |
| EP (1) | EP1159274B1 (es) |
| JP (1) | JP3447267B2 (es) |
| KR (1) | KR100491368B1 (es) |
| CN (2) | CN1140521C (es) |
| AR (1) | AR020863A1 (es) |
| AT (3) | ATE235478T1 (es) |
| AU (2) | AU1374500A (es) |
| BG (1) | BG65574B1 (es) |
| BR (1) | BR9917368B1 (es) |
| CA (2) | CA2475401A1 (es) |
| CH (1) | CH691305A5 (es) |
| CZ (1) | CZ292198B6 (es) |
| DE (2) | DE19983487C1 (es) |
| DK (2) | DK1159274T3 (es) |
| EA (1) | EA002560B1 (es) |
| ES (2) | ES2189699A1 (es) |
| FI (1) | FI108641B (es) |
| GB (2) | GB2357761B (es) |
| HK (1) | HK1049002B (es) |
| HU (1) | HUP0103235A3 (es) |
| IL (2) | IL145959A0 (es) |
| IS (1) | IS2343B (es) |
| IT (1) | ITMI991581A1 (es) |
| MX (1) | MXPA01010989A (es) |
| NO (1) | NO328542B1 (es) |
| NZ (1) | NZ514979A (es) |
| PL (1) | PL205579B1 (es) |
| PT (1) | PT1159274E (es) |
| SE (1) | SE516690C2 (es) |
| SI (1) | SI1159274T1 (es) |
| SK (1) | SK285813B6 (es) |
| TR (1) | TR200103702T2 (es) |
| UA (1) | UA63034C2 (es) |
| WO (1) | WO2000013648A2 (es) |
| ZA (1) | ZA200108854B (es) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL143422A0 (en) | 1998-12-23 | 2002-04-21 | Lundbeck & Co As H | Method for the preparation of 5-cyanophthalide |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| DK1173431T4 (da) | 1999-04-14 | 2010-01-04 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af citalopram |
| ITMI991579A1 (it) | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| HRP20020344B1 (hr) | 1999-10-25 | 2010-10-31 | H. Lundbeck A/S | Način priprave citaloprama |
| GB2360281B (en) | 1999-10-25 | 2002-01-16 | Lundbeck & Co As H | Method for the preparation of citalopram |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| HUP0203635A3 (en) | 1999-12-28 | 2005-02-28 | Lundbeck & Co As H | Method for the preparation of citalopram |
| PT1246813E (pt) | 1999-12-30 | 2004-02-27 | Lundbeck & Co As H | Metodo para a preparacao de citalopram |
| CN1195749C (zh) | 2000-01-14 | 2005-04-06 | H.隆德贝克有限公司 | 制备5－氰基2－苯并[c]呋喃酮的方法 |
| NL1017415C1 (nl) | 2000-02-24 | 2001-05-18 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| NL1017417C1 (nl) | 2000-03-03 | 2001-03-16 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| GB2357762B (en) * | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| CN1427835A (zh) | 2000-03-13 | 2003-07-02 | H·隆德贝克有限公司 | 5－取代的1－(4－氟苯基)－1,3－二氢异苯并呋喃的分步烷基化 |
| KR20020080481A (ko) | 2000-03-13 | 2002-10-23 | 하. 룬트벡 아크티에 셀스카브 | 시탈로프람의 제조 방법 |
| TR200202155T2 (tr) | 2000-03-14 | 2002-12-23 | H. Lundbeck A/S | Sitalopramin preparasyon metodu |
| DE10190485T1 (de) * | 2000-03-16 | 2002-03-21 | Lundbeck & Co As H | Verfahren zur Herstellung von 5-Cyano-1-(4-fluorphenyl)-1,3-dihydroisobenzofuranen |
| AR032455A1 (es) | 2000-05-12 | 2003-11-12 | Lundbeck & Co As H | Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva |
| CA2383963A1 (en) * | 2000-07-06 | 2002-01-17 | Eva Bolzonella | Method for the preparation of citalopram |
| CA2354877C (en) * | 2000-08-18 | 2006-05-02 | H. Lundbeck A/S | Method for the preparation of citalopram |
| WO2001045483A2 (en) * | 2000-12-22 | 2001-06-28 | H. Lundbeck A/S | Method for the preparation of pure citalopram |
| JP2003519121A (ja) * | 2000-12-28 | 2003-06-17 | ハー・ルンドベック・アクチエゼルスカベット | 純粋なシタロプラムの製造方法 |
| EP1355897A1 (en) | 2001-01-30 | 2003-10-29 | Orion Corporation Fermion | Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile |
| GB0105627D0 (en) * | 2001-03-07 | 2001-04-25 | Cipla Ltd | Preparation of phthalanes |
| JP2005500256A (ja) * | 2001-03-09 | 2005-01-06 | ランバクシー ラボラトリーズ リミテッド | シタロプラム製造方法 |
| US6967259B2 (en) * | 2001-09-24 | 2005-11-22 | Pharmachem Technologies Limited | Process for the preparation of Citalopram intermediate |
| US7148364B2 (en) * | 2002-01-07 | 2006-12-12 | Sun Pharmaceutical Industries | Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile |
| AR040970A1 (es) | 2002-08-12 | 2005-04-27 | Lundbeck & Co As H | Metodo para la separacion de intermediarios que pueden ser utilizados para la preparacion de escitalopram |
| WO2004085416A1 (en) * | 2003-03-24 | 2004-10-07 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
| US7019153B2 (en) | 2003-06-10 | 2006-03-28 | Sun Pharmaceutical Industries Limited | Process for hydrogenolysis of [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofuran acetamido-3-substituted-3-cephem-4-carboxylic acid |
| TWI339651B (en) | 2004-02-12 | 2011-04-01 | Lundbeck & Co As H | Method for the separation of intermediates which may be used for the preparation of escitalopram |
| ES2285972T1 (es) | 2004-08-23 | 2007-12-01 | Sun Pharmaceutical Industries Limited | Procedimiento de fabricacion de citalopram y enantiomeros. |
| TWI347942B (en) * | 2005-06-22 | 2011-09-01 | Lundbeck & Co As H | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| US7834201B2 (en) | 2005-06-22 | 2010-11-16 | H. Lundbeck A/S | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| EP2017271A1 (en) | 2007-07-06 | 2009-01-21 | Aurobindo Pharma Limited | Process for the preparation of escitalopram |
| CN114763343B (zh) * | 2021-01-14 | 2026-02-10 | 浙江华海药业股份有限公司 | 一种西酞普兰或s-西酞普兰的纯化方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143703A (es) * | 1965-03-18 | |||
| GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| GB8814057D0 (en) * | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
| US5296507A (en) * | 1990-09-06 | 1994-03-22 | H.Lundbeck A/S | Treatment of cerbrovascular disorders |
| DK213290D0 (da) * | 1990-09-06 | 1990-09-06 | Lundbeck & Co As H | Treatment of cerebrovascular disorders |
| DE19626659A1 (de) * | 1996-07-03 | 1998-01-08 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
| DE19627697A1 (de) * | 1996-07-10 | 1998-01-15 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
| ES2148120T3 (es) * | 1997-07-08 | 2002-01-16 | Lundbeck & Co As H | Metodo para la preparacion de citalopram. |
| UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| EA002770B1 (ru) * | 1997-11-11 | 2002-08-29 | Х.Лундбекк А/С | Способ получения циталопрама |
| PL199423B1 (pl) * | 1998-10-20 | 2008-09-30 | Lundbeck & Co As H | Sposób wytwarzania citalopramu |
| IL143422A0 (en) * | 1998-12-23 | 2002-04-21 | Lundbeck & Co As H | Method for the preparation of 5-cyanophthalide |
| AR022329A1 (es) * | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| DK1173431T4 (da) * | 1999-04-14 | 2010-01-04 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af citalopram |
| ITMI991579A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| GB2360281B (en) * | 1999-10-25 | 2002-01-16 | Lundbeck & Co As H | Method for the preparation of citalopram |
| AR026063A1 (es) * | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| IES20010143A2 (en) * | 2000-02-24 | 2001-07-25 | Lundbeck & Co As H | Method for the preparation of citalopram |
| NL1017415C1 (nl) * | 2000-02-24 | 2001-05-18 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| CA2354877C (en) * | 2000-08-18 | 2006-05-02 | H. Lundbeck A/S | Method for the preparation of citalopram |
| WO2001045483A2 (en) * | 2000-12-22 | 2001-06-28 | H. Lundbeck A/S | Method for the preparation of pure citalopram |
| JP2003519121A (ja) * | 2000-12-28 | 2003-06-17 | ハー・ルンドベック・アクチエゼルスカベット | 純粋なシタロプラムの製造方法 |
-
1999
- 1999-07-15 IT IT1999MI001581A patent/ITMI991581A1/it unknown
- 1999-11-22 CZ CZ2001320A patent/CZ292198B6/cs not_active IP Right Cessation
- 1999-11-22 HK HK03101234.1A patent/HK1049002B/zh not_active IP Right Cessation
- 1999-11-22 CA CA002475401A patent/CA2475401A1/en not_active Abandoned
- 1999-11-22 SK SK1840-2001A patent/SK285813B6/sk not_active IP Right Cessation
- 1999-11-22 GB GB0105182A patent/GB2357761B/en not_active Expired - Fee Related
- 1999-11-22 ES ES200150011A patent/ES2189699A1/es not_active Withdrawn
- 1999-11-22 EA EA200101072A patent/EA002560B1/ru not_active IP Right Cessation
- 1999-11-22 JP JP2000568457A patent/JP3447267B2/ja not_active Expired - Fee Related
- 1999-11-22 CA CA002290127A patent/CA2290127C/en not_active Expired - Fee Related
- 1999-11-22 NZ NZ514979A patent/NZ514979A/en not_active IP Right Cessation
- 1999-11-22 AU AU13745/00A patent/AU1374500A/en active Pending
- 1999-11-22 AU AU2001100440A patent/AU2001100440B4/en not_active Expired
- 1999-11-22 KR KR10-2001-7014053A patent/KR100491368B1/ko not_active Expired - Fee Related
- 1999-11-22 CH CH00308/01A patent/CH691305A5/de not_active IP Right Cessation
- 1999-11-22 SI SI9930276T patent/SI1159274T1/xx unknown
- 1999-11-22 DE DE19983487A patent/DE19983487C1/de not_active Expired - Fee Related
- 1999-11-22 GB GB0101504A patent/GB2354239B/en not_active Expired - Fee Related
- 1999-11-22 IL IL14595999A patent/IL145959A0/xx active IP Right Grant
- 1999-11-22 UA UA2001118041A patent/UA63034C2/uk unknown
- 1999-11-22 AT AT99968622T patent/ATE235478T1/de not_active IP Right Cessation
- 1999-11-22 DE DE69906389T patent/DE69906389T2/de not_active Expired - Lifetime
- 1999-11-22 MX MXPA01010989A patent/MXPA01010989A/es not_active IP Right Cessation
- 1999-11-22 PT PT99968622T patent/PT1159274E/pt unknown
- 1999-11-22 WO PCT/DK1999/000640 patent/WO2000013648A2/en not_active Ceased
- 1999-11-22 EP EP99968622A patent/EP1159274B1/en not_active Expired - Lifetime
- 1999-11-22 CN CNB998167517A patent/CN1140521C/zh not_active Expired - Fee Related
- 1999-11-22 PL PL346237A patent/PL205579B1/pl not_active IP Right Cessation
- 1999-11-22 CN CNA2003101187801A patent/CN1502616A/zh active Pending
- 1999-11-22 AT AT0904199A patent/AT409961B/de not_active IP Right Cessation
- 1999-11-22 HU HU0103235A patent/HUP0103235A3/hu unknown
- 1999-11-22 TR TR2001/03702T patent/TR200103702T2/xx unknown
- 1999-11-22 BR BRPI9917368-9A patent/BR9917368B1/pt not_active IP Right Cessation
- 1999-11-22 DK DK99968622T patent/DK1159274T3/da active
- 1999-11-22 ES ES99968622T patent/ES2194545T3/es not_active Expired - Lifetime
-
2000
- 2000-06-20 AR ARP000103055A patent/AR020863A1/es active IP Right Grant
-
2001
- 2001-01-15 DK DK200100060A patent/DK200100060A/da not_active Application Discontinuation
- 2001-01-19 NO NO20010319A patent/NO328542B1/no not_active IP Right Cessation
- 2001-01-24 SE SE0100193A patent/SE516690C2/sv not_active IP Right Cessation
- 2001-01-25 FI FI20010155A patent/FI108641B/fi not_active IP Right Cessation
- 2001-02-23 IS IS5861A patent/IS2343B/is unknown
- 2001-03-13 AT AT0018401U patent/AT4365U1/de not_active IP Right Cessation
- 2001-10-16 IL IL145959A patent/IL145959A/en not_active IP Right Cessation
- 2001-10-26 ZA ZA200108854A patent/ZA200108854B/xx unknown
- 2001-11-06 US US10/012,054 patent/US20020077353A1/en not_active Abandoned
- 2001-12-07 BG BG106191A patent/BG65574B1/bg unknown
-
2008
- 2008-12-08 US US12/329,750 patent/US20090088469A1/en not_active Abandoned
Also Published As
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