UA70334C2 - BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS - Google Patents
BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS Download PDFInfo
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- UA70334C2 UA70334C2 UA2001031998A UA2001031998A UA70334C2 UA 70334 C2 UA70334 C2 UA 70334C2 UA 2001031998 A UA2001031998 A UA 2001031998A UA 2001031998 A UA2001031998 A UA 2001031998A UA 70334 C2 UA70334 C2 UA 70334C2
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- 239000005557 antagonist Substances 0.000 title description 5
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 4
- 150000003254 radicals Chemical class 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims description 4
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
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- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 238000010306 acid treatment Methods 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
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- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 abstract description 13
- 150000002431 hydrogen Chemical group 0.000 abstract description 6
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 239000000843 powder Substances 0.000 description 4
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- 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 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
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- BEKDZRXUWYOOPU-UHFFFAOYSA-N tert-butyl n-(4-chlorobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCl BEKDZRXUWYOOPU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P27/00—Drugs for disorders of the senses
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98203363 | 1998-10-06 | ||
| PCT/EP1999/007418 WO2000020422A1 (en) | 1998-10-06 | 1999-10-01 | BENZOTHIENO[3,2-c]PYRIDINES AS α2 ANTAGONISTS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA70334C2 true UA70334C2 (en) | 2004-10-15 |
Family
ID=8234188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001031998A UA70334C2 (en) | 1998-10-06 | 1999-01-10 | BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US6426350B1 (ru) |
| EP (1) | EP1117667B1 (ru) |
| JP (1) | JP4580555B2 (ru) |
| KR (1) | KR20010071828A (ru) |
| CN (1) | CN1158287C (ru) |
| AR (1) | AR023678A1 (ru) |
| AT (1) | ATE363485T1 (ru) |
| AU (1) | AU760226B2 (ru) |
| BG (1) | BG64625B1 (ru) |
| BR (1) | BR9913110A (ru) |
| CA (1) | CA2346084C (ru) |
| CZ (1) | CZ20011103A3 (ru) |
| DE (1) | DE69936219T2 (ru) |
| EE (1) | EE04835B1 (ru) |
| ES (1) | ES2288025T3 (ru) |
| HK (1) | HK1039113A1 (ru) |
| HU (1) | HUP0103612A3 (ru) |
| ID (1) | ID28280A (ru) |
| IL (2) | IL142442A0 (ru) |
| NO (1) | NO20011309L (ru) |
| NZ (1) | NZ509911A (ru) |
| PL (1) | PL347184A1 (ru) |
| RU (1) | RU2222542C2 (ru) |
| SK (1) | SK4312001A3 (ru) |
| TR (1) | TR200100954T2 (ru) |
| TW (1) | TWI251595B (ru) |
| UA (1) | UA70334C2 (ru) |
| WO (1) | WO2000020422A1 (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE494000T1 (de) * | 2002-03-08 | 2011-01-15 | Max Planck Gesellschaft | Verwendung von egfr transaktivierungsinhibitoren für menschlichen krebs |
| WO2003082825A1 (en) * | 2002-04-03 | 2003-10-09 | Orion Corporation | Use of an alfa2-adrenoreceptor antagonist for cns-related diseases |
| EP1757605A4 (en) | 2004-04-12 | 2007-12-19 | Taisho Pharmaceutical Co Ltd | CYCLIC AMINE COMPOUND |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3752820A (en) * | 1972-03-20 | 1973-08-14 | Colgate Palmolive Co | Substituted-1,2,3,4-tetrahydrobenzothieno(3,2-c)pyridine derivatives |
| FR2570701B1 (fr) * | 1984-09-27 | 1987-05-22 | Synthelabo | Derives de furo(3,2-c)pyridines, leur preparation et leur application en therapeutique |
| US4686226A (en) * | 1985-09-03 | 1987-08-11 | Merck & Co., Inc. | Substituted benzo[b]furo- and benzo[b]thieno quinolizines |
| JPH0256485A (ja) * | 1988-04-27 | 1990-02-26 | Glaxo Group Ltd | ラクタム誘導体 |
| US5100891A (en) * | 1991-01-18 | 1992-03-31 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[B]indoles and related compounds |
| ATE247114T1 (de) * | 1994-09-12 | 2003-08-15 | Lilly Co Eli | Serotonergische modulatoren |
| JP3274579B2 (ja) * | 1995-01-12 | 2002-04-15 | 住友製薬株式会社 | 脳血管障害に伴う精神症候治療剤 |
| UA52681C2 (ru) | 1997-04-08 | 2003-01-15 | Янссен Фармацевтика Н.В. | Производные 1,2,3,4-тетрагидро-бензофуро [3,2,-c] пиридина |
-
1999
- 1999-01-10 UA UA2001031998A patent/UA70334C2/uk unknown
- 1999-10-01 CZ CZ20011103A patent/CZ20011103A3/cs unknown
- 1999-10-01 JP JP2000574534A patent/JP4580555B2/ja not_active Expired - Fee Related
- 1999-10-01 EP EP99947469A patent/EP1117667B1/en not_active Expired - Lifetime
- 1999-10-01 TR TR2001/00954T patent/TR200100954T2/xx unknown
- 1999-10-01 TW TW088116899A patent/TWI251595B/zh not_active IP Right Cessation
- 1999-10-01 EE EEP200100206A patent/EE04835B1/xx not_active IP Right Cessation
- 1999-10-01 CN CNB998116777A patent/CN1158287C/zh not_active Expired - Fee Related
- 1999-10-01 AU AU60899/99A patent/AU760226B2/en not_active Ceased
- 1999-10-01 ID IDW20010781A patent/ID28280A/id unknown
- 1999-10-01 SK SK431-2001A patent/SK4312001A3/sk unknown
- 1999-10-01 PL PL99347184A patent/PL347184A1/xx not_active Application Discontinuation
- 1999-10-01 CA CA2346084A patent/CA2346084C/en not_active Expired - Fee Related
- 1999-10-01 ES ES99947469T patent/ES2288025T3/es not_active Expired - Lifetime
- 1999-10-01 DE DE69936219T patent/DE69936219T2/de not_active Expired - Lifetime
- 1999-10-01 KR KR1020017000400A patent/KR20010071828A/ko active Search and Examination
- 1999-10-01 US US09/806,432 patent/US6426350B1/en not_active Expired - Lifetime
- 1999-10-01 WO PCT/EP1999/007418 patent/WO2000020422A1/en active IP Right Grant
- 1999-10-01 RU RU2001111753/04A patent/RU2222542C2/ru not_active IP Right Cessation
- 1999-10-01 BR BR9913110-2A patent/BR9913110A/pt not_active Application Discontinuation
- 1999-10-01 IL IL14244299A patent/IL142442A0/xx active IP Right Grant
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- 1999-10-01 HU HU0103612A patent/HUP0103612A3/hu unknown
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- 1999-10-05 AR ARP990105039A patent/AR023678A1/es active IP Right Grant
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2001
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2002
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