ZA200404294B - Novel benzothiazine and benzothiadiazine derivatives, method for preparing same and pharmaceutical compositions containing same. - Google Patents
Novel benzothiazine and benzothiadiazine derivatives, method for preparing same and pharmaceutical compositions containing same. Download PDFInfo
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- ZA200404294B ZA200404294B ZA200404294A ZA200404294A ZA200404294B ZA 200404294 B ZA200404294 B ZA 200404294B ZA 200404294 A ZA200404294 A ZA 200404294A ZA 200404294 A ZA200404294 A ZA 200404294A ZA 200404294 B ZA200404294 B ZA 200404294B
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- 238000000034 method Methods 0.000 title claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000007658 benzothiadiazines Chemical class 0.000 title description 4
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 97
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- -1 cyano, nitro, amino Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 230000009471 action Effects 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- OSXDHRVFRPBPBH-UHFFFAOYSA-N 7-(3-methylphenoxy)-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide Chemical compound CC1=CC=CC(OC=2C=C3S(=O)(=O)NC4CCCN4C3=CC=2)=C1 OSXDHRVFRPBPBH-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
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- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
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- 231100000252 nontoxic Toxicity 0.000 claims description 2
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- 150000002901 organomagnesium compounds Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
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- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims 1
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- QWAOZSRWNZGEOO-UHFFFAOYSA-N [3-[(5,5-dioxo-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenyl]-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)C1=CC=CC(OC=2C=C3S(=O)(=O)NC4CCCN4C3=CC=2)=C1 QWAOZSRWNZGEOO-UHFFFAOYSA-N 0.000 claims 1
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- 238000004452 microanalysis Methods 0.000 description 36
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- 239000000047 product Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- 239000000203 mixture Substances 0.000 description 12
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- 108020003175 receptors Proteins 0.000 description 4
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- GZDNYQLUOGPCDR-UHFFFAOYSA-N 7-(3-methoxyphenoxy)-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide Chemical compound COC1=CC=CC(OC=2C=C3S(=O)(=O)NC4CCCN4C3=CC=2)=C1 GZDNYQLUOGPCDR-UHFFFAOYSA-N 0.000 description 3
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- 229910021529 ammonia Inorganic materials 0.000 description 3
- HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 3
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- RZEDJEWRTBCQKC-UHFFFAOYSA-N 2-amino-3-methoxybenzenesulfonamide Chemical compound COC1=CC=CC(S(N)(=O)=O)=C1N RZEDJEWRTBCQKC-UHFFFAOYSA-N 0.000 description 1
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- 230000003993 interaction Effects 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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 |
|---|---|---|---|
| FR0116621A FR2833956B1 (fr) | 2001-12-21 | 2001-12-21 | Nouveaux derives de benzothiazine et de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200404294B true ZA200404294B (en) | 2005-06-01 |
Family
ID=8870809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200404294A ZA200404294B (en) | 2001-12-21 | 2004-06-01 | Novel benzothiazine and benzothiadiazine derivatives, method for preparing same and pharmaceutical compositions containing same. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7253161B2 (pt) |
| EP (1) | EP1480986A1 (pt) |
| JP (1) | JP2005518386A (pt) |
| KR (1) | KR100586685B1 (pt) |
| CN (1) | CN1289509C (pt) |
| AR (1) | AR038028A1 (pt) |
| AU (1) | AU2002364674B2 (pt) |
| BR (1) | BR0214973A (pt) |
| CA (1) | CA2471263A1 (pt) |
| EA (1) | EA007227B1 (pt) |
| FR (1) | FR2833956B1 (pt) |
| GE (1) | GEP20063759B (pt) |
| HK (1) | HK1071749A1 (pt) |
| HU (1) | HUP0402585A3 (pt) |
| MA (1) | MA27090A1 (pt) |
| MX (1) | MXPA04005837A (pt) |
| NO (1) | NO20042978L (pt) |
| NZ (1) | NZ533328A (pt) |
| PL (1) | PL370159A1 (pt) |
| UA (1) | UA77737C2 (pt) |
| WO (1) | WO2003053979A1 (pt) |
| ZA (1) | ZA200404294B (pt) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2856065B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2856064B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2877338B1 (fr) * | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2877342B1 (fr) * | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2879201B1 (fr) * | 2004-12-10 | 2007-02-16 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2955106B1 (fr) * | 2010-01-08 | 2011-12-23 | Servier Lab | Nouveaux derives de benzothiadiazines cyclopropylees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2013118845A1 (ja) * | 2012-02-08 | 2013-08-15 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| WO2019070044A1 (ja) | 2017-10-06 | 2019-04-11 | 武田薬品工業株式会社 | 複素環化合物 |
| CN107641197B (zh) * | 2017-10-30 | 2019-11-22 | 河南工程学院 | 一种以二氧化碳与环氧环己烷为单体的共聚反应催化剂 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2722502B1 (fr) * | 1994-07-12 | 1996-08-23 | Adir | Nouveau derive de benzothiadiazine, son procede depreparation et les compositions pharmaceutiques qui le contiennent |
| PL342843A1 (en) * | 1998-02-18 | 2001-07-16 | Neurosearch As | Novel compounds and their use as positive ampa receptor modulators |
| FR2812291B1 (fr) * | 2000-07-28 | 2002-12-13 | Adir | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2001
- 2001-12-21 FR FR0116621A patent/FR2833956B1/fr not_active Expired - Fee Related
-
2002
- 2002-12-18 AR ARP020104932A patent/AR038028A1/es unknown
- 2002-12-20 PL PL02370159A patent/PL370159A1/xx not_active Application Discontinuation
- 2002-12-20 GE GE5645A patent/GEP20063759B/en unknown
- 2002-12-20 JP JP2003554695A patent/JP2005518386A/ja active Pending
- 2002-12-20 KR KR1020047009302A patent/KR100586685B1/ko not_active IP Right Cessation
- 2002-12-20 WO PCT/FR2002/004485 patent/WO2003053979A1/fr active Application Filing
- 2002-12-20 CN CNB028258126A patent/CN1289509C/zh not_active Expired - Fee Related
- 2002-12-20 US US10/498,948 patent/US7253161B2/en not_active Expired - Fee Related
- 2002-12-20 HU HU0402585A patent/HUP0402585A3/hu unknown
- 2002-12-20 EA EA200400758A patent/EA007227B1/ru not_active IP Right Cessation
- 2002-12-20 AU AU2002364674A patent/AU2002364674B2/en not_active Ceased
- 2002-12-20 BR BR0214973-7A patent/BR0214973A/pt not_active IP Right Cessation
- 2002-12-20 MX MXPA04005837A patent/MXPA04005837A/es active IP Right Grant
- 2002-12-20 NZ NZ533328A patent/NZ533328A/en unknown
- 2002-12-20 EP EP02805408A patent/EP1480986A1/fr not_active Withdrawn
- 2002-12-20 CA CA002471263A patent/CA2471263A1/fr not_active Abandoned
- 2002-12-20 UA UA20040706011A patent/UA77737C2/uk unknown
-
2004
- 2004-06-01 ZA ZA200404294A patent/ZA200404294B/en unknown
- 2004-06-04 MA MA27719A patent/MA27090A1/fr unknown
- 2004-07-14 NO NO20042978A patent/NO20042978L/no not_active Application Discontinuation
-
2005
- 2005-05-30 HK HK05104494A patent/HK1071749A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GEP20063759B (en) | 2006-02-27 |
| HUP0402585A3 (en) | 2009-01-28 |
| NO20042978L (no) | 2004-07-14 |
| EP1480986A1 (fr) | 2004-12-01 |
| KR20040073480A (ko) | 2004-08-19 |
| FR2833956B1 (fr) | 2004-01-30 |
| CN1289509C (zh) | 2006-12-13 |
| MXPA04005837A (es) | 2004-09-10 |
| JP2005518386A (ja) | 2005-06-23 |
| NZ533328A (en) | 2006-10-27 |
| US20050124606A1 (en) | 2005-06-09 |
| US7253161B2 (en) | 2007-08-07 |
| PL370159A1 (en) | 2005-05-16 |
| EA007227B1 (ru) | 2006-08-25 |
| BR0214973A (pt) | 2004-12-14 |
| HUP0402585A2 (hu) | 2005-03-29 |
| UA77737C2 (en) | 2007-01-15 |
| CN1606560A (zh) | 2005-04-13 |
| EA200400758A1 (ru) | 2005-06-30 |
| AR038028A1 (es) | 2004-12-22 |
| FR2833956A1 (fr) | 2003-06-27 |
| AU2002364674B2 (en) | 2007-11-22 |
| MA27090A1 (fr) | 2004-12-20 |
| CA2471263A1 (fr) | 2003-07-03 |
| WO2003053979A1 (fr) | 2003-07-03 |
| AU2002364674A1 (en) | 2003-07-09 |
| HK1071749A1 (en) | 2005-07-29 |
| KR100586685B1 (ko) | 2006-06-08 |
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