KR20030017558A - 포스포디에스터라아제 Ｖ 억제 효과를 갖는5-아미노알킬피라졸로[4,3-ｄ]피리미딘 - Google Patents
포스포디에스터라아제 Ｖ 억제 효과를 갖는5-아미노알킬피라졸로[4,3-ｄ]피리미딘 Download PDFInfo
- Publication number
- KR20030017558A KR20030017558A KR1020027017571A KR20027017571A KR20030017558A KR 20030017558 A KR20030017558 A KR 20030017558A KR 1020027017571 A KR1020027017571 A KR 1020027017571A KR 20027017571 A KR20027017571 A KR 20027017571A KR 20030017558 A KR20030017558 A KR 20030017558A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- pyrazolo
- chloro
- propyl
- methoxybenzylamino
- 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.)
- Withdrawn
Links
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 5
- 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 title abstract 2
- 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 title abstract 2
- 150000003230 pyrimidines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 201000010099 disease Diseases 0.000 claims abstract description 5
- -1 propylene, butylene, pentylene, ethyleneoxy, methyleneoxy Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 6
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 claims description 5
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- VTBRRTSUVDZAIT-UHFFFAOYSA-N 2-[4-[[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]methyl]piperazin-1-yl]ethanol Chemical compound N1=C(CN2CCN(CCO)CC2)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 VTBRRTSUVDZAIT-UHFFFAOYSA-N 0.000 claims description 4
- DPYUKKSAOUEPMY-UHFFFAOYSA-N 2-[[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]methyl-ethylamino]ethanol Chemical compound N1=C(CN(CC)CCO)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 DPYUKKSAOUEPMY-UHFFFAOYSA-N 0.000 claims description 4
- LOFHIVCSHWBJTE-UHFFFAOYSA-N 2-[[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]methylamino]ethanol Chemical compound N1=C(CNCCO)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 LOFHIVCSHWBJTE-UHFFFAOYSA-N 0.000 claims description 4
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- ZTGOYVONMOSZMG-UHFFFAOYSA-N 5-[[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]methylamino]pentan-1-ol Chemical compound N1=C(CNCCCCCO)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 ZTGOYVONMOSZMG-UHFFFAOYSA-N 0.000 claims description 4
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
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- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
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- 229910021386 carbon form Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- LMDIIXFNJBXLSH-MBPAZGTNSA-N (2s,3s,4s,5r)-6-[[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]methyl-methylamino]hexane-1,2,3,4,5-pentol Chemical compound N1=C(CN(C)C[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 LMDIIXFNJBXLSH-MBPAZGTNSA-N 0.000 claims 3
- GZGLGTFVFTXVPN-UHFFFAOYSA-N 3-[[7-[(3-chloro-4-methoxyphenyl)methylamino]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-5-yl]methylamino]propan-1-ol Chemical compound N1=C(CNCCCO)N=C2C(CCC)=NN(C)C2=C1NCC1=CC=C(OC)C(Cl)=C1 GZGLGTFVFTXVPN-UHFFFAOYSA-N 0.000 claims 3
- AEUWLJSEFXGQHI-UHFFFAOYSA-N 1h-pyrazolo[4,3-d]pyrimidin-5-ylmethanamine Chemical compound NCC1=NC=C2NN=CC2=N1 AEUWLJSEFXGQHI-UHFFFAOYSA-N 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
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- 239000008194 pharmaceutical composition Substances 0.000 description 1
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- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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- DOTPSQVYOBAWPQ-UHFFFAOYSA-N pyrazolo[4,3-d]pyrimidin-3-one Chemical class N1=CN=C2C(=O)N=NC2=C1 DOTPSQVYOBAWPQ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10031584.4 | 2000-06-29 | ||
| DE10031584A DE10031584A1 (de) | 2000-06-29 | 2000-06-29 | 5-Aminoalkyl-pyrazolo[4,3-d]pyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20030017558A true KR20030017558A (ko) | 2003-03-03 |
Family
ID=7647151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027017571A Withdrawn KR20030017558A (ko) | 2000-06-29 | 2001-06-28 | 포스포디에스터라아제 Ｖ 억제 효과를 갖는5-아미노알킬피라졸로[4,3-ｄ]피리미딘 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7060823B2 (https=) |
| EP (1) | EP1296986B1 (https=) |
| JP (1) | JP4964388B2 (https=) |
| KR (1) | KR20030017558A (https=) |
| CN (1) | CN1439011A (https=) |
| AR (1) | AR028772A1 (https=) |
| AT (1) | ATE519761T1 (https=) |
| AU (2) | AU7970001A (https=) |
| BR (1) | BR0111915A (https=) |
| CA (1) | CA2410399C (https=) |
| CZ (1) | CZ20024054A3 (https=) |
| DE (1) | DE10031584A1 (https=) |
| ES (1) | ES2367704T3 (https=) |
| HU (1) | HUP0301587A3 (https=) |
| MX (1) | MXPA02012263A (https=) |
| NO (1) | NO20026247D0 (https=) |
| PL (1) | PL358551A1 (https=) |
| RU (1) | RU2271359C2 (https=) |
| SK (1) | SK17632002A3 (https=) |
| WO (1) | WO2002000660A1 (https=) |
| ZA (1) | ZA200209728B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19942474A1 (de) * | 1999-09-06 | 2001-03-15 | Merck Patent Gmbh | Pyrazolo[4,3-d]pyrimidine |
| DE10031585A1 (de) * | 2000-06-29 | 2002-01-10 | Merck Patent Gmbh | 2-Aminoalkyl-thieno[2,3-d]pyrimidine |
| DE10058662A1 (de) * | 2000-11-25 | 2002-05-29 | Merck Patent Gmbh | Verwendung von Pyrazolo[4,3-d]pyrimidinen |
| OA13050A (en) | 2003-04-29 | 2006-11-10 | Pfizer Ltd | 5,7-diaminopyrazolo [4,3-D] pyrimidines useful in the treatment of hypertension. |
| UA80871C2 (en) * | 2003-04-29 | 2007-11-12 | Pfizer Ltd | 5,7-diaminopyrazolo[4,3-d]pyrimidines useful in the treatment of hypertension |
| GB0327319D0 (en) * | 2003-11-24 | 2003-12-24 | Pfizer Ltd | Novel pharmaceuticals |
| GB0327323D0 (en) * | 2003-11-24 | 2003-12-31 | Pfizer Ltd | Novel pharmaceuticals |
| US7572799B2 (en) | 2003-11-24 | 2009-08-11 | Pfizer Inc | Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors |
| CA2562251C (en) * | 2004-04-07 | 2009-04-28 | Pfizer Inc. | Pyrazolo'4,3-d pyrimidines |
| EP1809632A2 (en) * | 2004-10-28 | 2007-07-25 | Pharmacia & Upjohn Company LLC | Pyrazolo[4,3-d]pyrimidine derivatives useful as pde-5 inhibitors |
| CA2608018C (en) | 2005-05-12 | 2010-07-13 | Pfizer Inc. | Anhydrous crystalline forms of n-[1-(2-ethoxyethyl)-5-(n-ethyl-n-methylamino)-7-(4-methylpyridin-2-yl-amino)-1h-pyrazolo[4,3-d]pyrimidine-3-carbonyl]methanesulfonamide |
| NL2000291C2 (nl) | 2005-11-10 | 2009-02-17 | Pfizer Prod Inc | 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H- pyrazool(4,3-d)pyrimidine-5-yl)piperidine-4-carbonzuur en zouten daarvan. |
| DE102012200360A1 (de) * | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte Triazine und ihre Verwendung |
| CA2782774A1 (en) * | 2012-07-06 | 2014-01-06 | Pharmascience Inc. | Protein kinase inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1739850A3 (ru) * | 1987-08-31 | 1992-06-07 | Такеда Кемикал Индастриз, Лтд (Фирма) | Способ получени конденсированных производных пиразоло[3,4- @ ]пиримидина |
| US5075310A (en) * | 1988-07-01 | 1991-12-24 | Smith Kline & French Laboratories, Ltd. | Pyrimidone derivatives as bronchodilators |
| GB9119704D0 (en) * | 1991-09-14 | 1991-10-30 | Pfizer Ltd | Therapeutic agents |
| JP2657760B2 (ja) | 1992-07-15 | 1997-09-24 | 小野薬品工業株式会社 | ４−アミノキナゾリン誘導体およびそれを含有する医薬品 |
| GB9311920D0 (en) * | 1993-06-09 | 1993-07-28 | Pfizer Ltd | Therapeutic agents |
| GB9423911D0 (en) | 1994-11-26 | 1995-01-11 | Pfizer Ltd | Therapeutic agents |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| DE19644228A1 (de) * | 1996-10-24 | 1998-04-30 | Merck Patent Gmbh | Thienopyrimidine |
| DE19752952A1 (de) * | 1997-11-28 | 1999-06-02 | Merck Patent Gmbh | Thienopyrimidine |
| DE19942474A1 (de) * | 1999-09-06 | 2001-03-15 | Merck Patent Gmbh | Pyrazolo[4,3-d]pyrimidine |
-
2000
- 2000-06-29 DE DE10031584A patent/DE10031584A1/de not_active Withdrawn
-
2001
- 2001-06-28 KR KR1020027017571A patent/KR20030017558A/ko not_active Withdrawn
- 2001-06-28 CN CN01811801A patent/CN1439011A/zh active Pending
- 2001-06-28 EP EP01957901A patent/EP1296986B1/de not_active Expired - Lifetime
- 2001-06-28 CA CA2410399A patent/CA2410399C/en not_active Expired - Fee Related
- 2001-06-28 MX MXPA02012263A patent/MXPA02012263A/es unknown
- 2001-06-28 HU HU0301587A patent/HUP0301587A3/hu unknown
- 2001-06-28 BR BR0111915-0A patent/BR0111915A/pt not_active IP Right Cessation
- 2001-06-28 SK SK1763-2002A patent/SK17632002A3/sk unknown
- 2001-06-28 AU AU7970001A patent/AU7970001A/xx active Pending
- 2001-06-28 RU RU2003100508/04A patent/RU2271359C2/ru not_active IP Right Cessation
- 2001-06-28 JP JP2002505784A patent/JP4964388B2/ja not_active Expired - Fee Related
- 2001-06-28 US US10/312,766 patent/US7060823B2/en not_active Expired - Fee Related
- 2001-06-28 AT AT01957901T patent/ATE519761T1/de active
- 2001-06-28 PL PL01358551A patent/PL358551A1/xx unknown
- 2001-06-28 ES ES01957901T patent/ES2367704T3/es not_active Expired - Lifetime
- 2001-06-28 CZ CZ20024054A patent/CZ20024054A3/cs unknown
- 2001-06-28 AU AU2001279700A patent/AU2001279700B2/en not_active Ceased
- 2001-06-28 WO PCT/EP2001/007378 patent/WO2002000660A1/de not_active Ceased
- 2001-06-29 AR ARP010103144A patent/AR028772A1/es unknown
-
2002
- 2002-11-29 ZA ZA200209728A patent/ZA200209728B/en unknown
- 2002-12-27 NO NO20026247A patent/NO20026247D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20040029900A1 (en) | 2004-02-12 |
| PL358551A1 (en) | 2004-08-09 |
| NO20026247L (no) | 2002-12-27 |
| ZA200209728B (en) | 2004-03-12 |
| MXPA02012263A (es) | 2003-04-25 |
| DE10031584A1 (de) | 2002-01-10 |
| AR028772A1 (es) | 2003-05-21 |
| NO20026247D0 (no) | 2002-12-27 |
| CZ20024054A3 (cs) | 2003-04-16 |
| JP2004501921A (ja) | 2004-01-22 |
| ES2367704T3 (es) | 2011-11-07 |
| EP1296986B1 (de) | 2011-08-10 |
| AU7970001A (en) | 2002-01-08 |
| CN1439011A (zh) | 2003-08-27 |
| SK17632002A3 (sk) | 2003-05-02 |
| CA2410399A1 (en) | 2002-01-03 |
| AU2001279700B2 (en) | 2006-08-24 |
| RU2271359C2 (ru) | 2006-03-10 |
| US7060823B2 (en) | 2006-06-13 |
| ATE519761T1 (de) | 2011-08-15 |
| JP4964388B2 (ja) | 2012-06-27 |
| BR0111915A (pt) | 2003-05-13 |
| WO2002000660A1 (de) | 2002-01-03 |
| HUP0301587A2 (hu) | 2003-09-29 |
| HUP0301587A3 (en) | 2005-11-28 |
| CA2410399C (en) | 2010-02-16 |
| EP1296986A1 (de) | 2003-04-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20021223 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |