NO317104B1 - Ftalimidoarylpiperaziner som <alfa> 1A reseptorantagonister anvendelige ved behandling av benign prostata hyperplasi, og farmasoytisk sammensetning innbefattende samme - Google Patents
Ftalimidoarylpiperaziner som <alfa> 1A reseptorantagonister anvendelige ved behandling av benign prostata hyperplasi, og farmasoytisk sammensetning innbefattende samme Download PDFInfo
- Publication number
- NO317104B1 NO317104B1 NO20004142A NO20004142A NO317104B1 NO 317104 B1 NO317104 B1 NO 317104B1 NO 20004142 A NO20004142 A NO 20004142A NO 20004142 A NO20004142 A NO 20004142A NO 317104 B1 NO317104 B1 NO 317104B1
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- hydroxy
- alkyl
- compound
- phenyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 title description 18
- 238000011282 treatment Methods 0.000 title description 16
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- CCJMGYBFMJJAIY-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-n-[2-hydroxy-3-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]propyl]-1,3-dioxoisoindole-5-carboxamide Chemical compound CC(C)OC1=CC=CC=C1N1CCN(CC(O)CNC(=O)C=2C=C3C(=O)N(C(=O)C3=CC=2)C=2C=CC(O)=CC=2)CC1 CCJMGYBFMJJAIY-UHFFFAOYSA-N 0.000 claims 1
- LQTJOPPTSIYEES-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-n-[2-hydroxy-3-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]propyl]-1,3-dioxoisoindole-5-carboxamide Chemical compound CC(C)OC1=CC=CC=C1N1CCN(CC(O)CNC(=O)C=2C=C3C(=O)N(C(=O)C3=CC=2)C=2C=CC(=CC=2)N(C)C)CC1 LQTJOPPTSIYEES-UHFFFAOYSA-N 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- IWGZAYZZRNFQRX-UHFFFAOYSA-N n-[2-hydroxy-3-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]propyl]-2-(3-methoxyphenyl)-1,3-dioxoisoindole-5-carboxamide Chemical compound COC1=CC=CC(N2C(C3=CC(=CC=C3C2=O)C(=O)NCC(O)CN2CCN(CC2)C=2C(=CC=CC=2)OC(C)C)=O)=C1 IWGZAYZZRNFQRX-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
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- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 6
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- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- GISJHCLTIVIGLX-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methoxy]pyridin-2-yl]-2-(2,6-difluorophenyl)acetamide Chemical compound FC1=CC=CC(F)=C1CC(=O)NC1=CC(OCC=2C=CC(Cl)=CC=2)=CC=N1 GISJHCLTIVIGLX-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000008008 oral excipient Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003906 phosphoinositides Chemical class 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 230000001144 postural effect Effects 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940072254 proscar Drugs 0.000 description 1
- 238000011471 prostatectomy Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003653 radioligand binding assay Methods 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 230000025102 vascular smooth muscle contraction Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7551098P | 1998-02-20 | 1998-02-20 | |
| PCT/US1999/003694 WO1999042445A1 (en) | 1998-02-20 | 1999-02-19 | Phtalimido arylpiperazines as alpha 1a receptor antagonists useful in the treatment of benign prostatic hyperplasia |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20004142D0 NO20004142D0 (no) | 2000-08-18 |
| NO20004142L NO20004142L (no) | 2000-10-19 |
| NO317104B1 true NO317104B1 (no) | 2004-08-09 |
Family
ID=22126243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20004142A NO317104B1 (no) | 1998-02-20 | 2000-08-18 | Ftalimidoarylpiperaziner som <alfa> 1A reseptorantagonister anvendelige ved behandling av benign prostata hyperplasi, og farmasoytisk sammensetning innbefattende samme |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US20020077476A1 (de) |
| EP (1) | EP1056720B1 (de) |
| JP (1) | JP2002503722A (de) |
| KR (1) | KR100608473B1 (de) |
| CN (1) | CN1172911C (de) |
| AR (1) | AR015521A1 (de) |
| AT (1) | ATE280156T1 (de) |
| AU (1) | AU766411B2 (de) |
| BR (1) | BR9908122A (de) |
| DE (1) | DE69921300T2 (de) |
| ES (1) | ES2233023T3 (de) |
| HK (1) | HK1031872A1 (de) |
| HU (1) | HUP0100704A3 (de) |
| IL (2) | IL137953A0 (de) |
| NO (1) | NO317104B1 (de) |
| NZ (1) | NZ506461A (de) |
| PL (1) | PL194649B1 (de) |
| PT (1) | PT1056720E (de) |
| TR (1) | TR200003224T2 (de) |
| WO (1) | WO1999042445A1 (de) |
| ZA (1) | ZA991319B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20010164A1 (it) * | 2001-01-30 | 2002-07-30 | Recordati Chem Pharm | Alfa 1 antagonisti selettivi a + d |
| CN103387531A (zh) * | 2012-05-10 | 2013-11-13 | 广州医学院 | 酰胺类芳基哌嗪衍生物及其制备方法和在抗良性前列腺增生中的应用 |
| HUP1400294A2 (hu) | 2014-06-13 | 2015-12-28 | Skillpharm Kft | Clopidogrel új alkalmazása |
| CN105061434B (zh) * | 2015-07-30 | 2017-07-21 | 新发药业有限公司 | 一种西他列汀磷酸盐的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1382742A (en) | 1972-09-19 | 1975-02-05 | Labaz | Benzofuran derivatives and process for preparing the same |
| CH585693A5 (de) | 1974-02-08 | 1977-03-15 | Ciba Geigy Ag | |
| HU177702B (en) | 1977-10-24 | 1981-12-28 | Noevenyvedelmi Kutato Intezet | Plant growth regulator and process for preparing the active materials |
| PT82077B (fr) * | 1985-02-26 | 1987-09-25 | Sanofi Sa | Procede pour l'obtention des derives aminoalcools peptidiques inhibiteurs de la renine et des proteases acides |
| FR2678271B1 (fr) * | 1991-06-27 | 1995-01-13 | Synthelabo | Derives de pyrimidine-4-carboxamide, leur preparation et leur application en therapeutique. |
| US5428037A (en) * | 1993-04-09 | 1995-06-27 | Syntex Pharmaceuticals, Ltd. | Heterocyclic derivatives in the treatment of Ischaemia and related diseases |
| EA001904B1 (ru) * | 1997-05-12 | 2001-10-22 | ОРТО МакНЕЙЛ ФАРМАСЬЮТИКАЛ, ИНК. | Арилзамещенные пиперазины для лечения доброкачественной гиперплазии простаты |
-
1999
- 1999-02-18 ZA ZA9901319A patent/ZA991319B/xx unknown
- 1999-02-19 KR KR1020007009159A patent/KR100608473B1/ko not_active IP Right Cessation
- 1999-02-19 WO PCT/US1999/003694 patent/WO1999042445A1/en active IP Right Grant
- 1999-02-19 PT PT99908303T patent/PT1056720E/pt unknown
- 1999-02-19 EP EP99908303A patent/EP1056720B1/de not_active Expired - Lifetime
- 1999-02-19 IL IL13795399A patent/IL137953A0/xx active IP Right Grant
- 1999-02-19 TR TR2000/03224T patent/TR200003224T2/xx unknown
- 1999-02-19 DE DE69921300T patent/DE69921300T2/de not_active Expired - Fee Related
- 1999-02-19 NZ NZ506461A patent/NZ506461A/en unknown
- 1999-02-19 PL PL99342357A patent/PL194649B1/pl not_active IP Right Cessation
- 1999-02-19 ES ES99908303T patent/ES2233023T3/es not_active Expired - Lifetime
- 1999-02-19 CN CNB998030260A patent/CN1172911C/zh not_active Expired - Fee Related
- 1999-02-19 AT AT99908303T patent/ATE280156T1/de not_active IP Right Cessation
- 1999-02-19 HU HU0100704A patent/HUP0100704A3/hu unknown
- 1999-02-19 JP JP2000532397A patent/JP2002503722A/ja not_active Withdrawn
- 1999-02-19 AU AU27765/99A patent/AU766411B2/en not_active Ceased
- 1999-02-19 BR BR9908122-9A patent/BR9908122A/pt not_active Application Discontinuation
- 1999-02-23 AR ARP990100676A patent/AR015521A1/es active IP Right Grant
-
2000
- 2000-08-18 IL IL137953A patent/IL137953A/en not_active IP Right Cessation
- 2000-08-18 NO NO20004142A patent/NO317104B1/no not_active IP Right Cessation
-
2001
- 2001-04-03 HK HK01102397A patent/HK1031872A1/xx not_active IP Right Cessation
- 2001-12-11 US US10/014,979 patent/US20020077476A1/en not_active Abandoned
-
2002
- 2002-07-29 US US10/207,473 patent/US6780994B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0100704A3 (en) | 2002-10-28 |
| HK1031872A1 (en) | 2001-06-29 |
| AU766411B2 (en) | 2003-10-16 |
| BR9908122A (pt) | 2001-11-13 |
| EP1056720B1 (de) | 2004-10-20 |
| CN1172911C (zh) | 2004-10-27 |
| JP2002503722A (ja) | 2002-02-05 |
| ZA991319B (en) | 2000-11-20 |
| DE69921300D1 (de) | 2004-11-25 |
| CN1291185A (zh) | 2001-04-11 |
| ATE280156T1 (de) | 2004-11-15 |
| KR100608473B1 (ko) | 2006-08-09 |
| PL342357A1 (en) | 2001-06-04 |
| PL194649B1 (pl) | 2007-06-29 |
| US20020077476A1 (en) | 2002-06-20 |
| KR20010041118A (ko) | 2001-05-15 |
| US20030088099A1 (en) | 2003-05-08 |
| WO1999042445A1 (en) | 1999-08-26 |
| NZ506461A (en) | 2003-08-29 |
| IL137953A0 (en) | 2001-10-31 |
| ES2233023T3 (es) | 2005-06-01 |
| EP1056720A1 (de) | 2000-12-06 |
| PT1056720E (pt) | 2005-02-28 |
| AU2776599A (en) | 1999-09-06 |
| NO20004142L (no) | 2000-10-19 |
| HUP0100704A2 (hu) | 2001-10-28 |
| TR200003224T2 (tr) | 2001-03-21 |
| NO20004142D0 (no) | 2000-08-18 |
| US6780994B2 (en) | 2004-08-24 |
| IL137953A (en) | 2006-12-31 |
| DE69921300T2 (de) | 2006-03-09 |
| AR015521A1 (es) | 2001-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |