DE69806411T2 - Neue antiarrythmische verbindungen - Google Patents
Neue antiarrythmische verbindungenInfo
- Publication number
- DE69806411T2 DE69806411T2 DE69806411T DE69806411T DE69806411T2 DE 69806411 T2 DE69806411 T2 DE 69806411T2 DE 69806411 T DE69806411 T DE 69806411T DE 69806411 T DE69806411 T DE 69806411T DE 69806411 T2 DE69806411 T2 DE 69806411T2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- compounds
- dimethylphenoxy
- ethyl
- methylethyl
- 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
- 230000003288 anthiarrhythmic effect Effects 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
- 150000004677 hydrates Chemical class 0.000 claims abstract description 3
- 239000002207 metabolite Substances 0.000 claims abstract description 3
- 239000000651 prodrug Substances 0.000 claims abstract description 3
- 229940002612 prodrug Drugs 0.000 claims abstract description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract 2
- 206010003119 arrhythmia Diseases 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 14
- IYIJFSQSQILPMZ-UHFFFAOYSA-N 4-[2-[1-(2,6-dimethylphenoxy)propan-2-yl-methylamino]ethyl]aniline Chemical compound C=1C=C(N)C=CC=1CCN(C)C(C)COC1=C(C)C=CC=C1C IYIJFSQSQILPMZ-UHFFFAOYSA-N 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
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- 229940126601 medicinal product Drugs 0.000 claims description 3
- LBRKPAVUKRQZLP-UHFFFAOYSA-N 1-[4-[2-[1-(2,6-dimethylphenoxy)propan-2-yl-methylamino]ethyl]phenyl]-3-methylthiourea Chemical compound C1=CC(NC(=S)NC)=CC=C1CCN(C)C(C)COC1=C(C)C=CC=C1C LBRKPAVUKRQZLP-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- OCULOLABMGTDLY-UHFFFAOYSA-N n-[4-[2-[1-(2,6-dimethylphenoxy)propan-2-yl-methylamino]ethyl]phenyl]acetamide Chemical compound C=1C=C(NC(C)=O)C=CC=1CCN(C)C(C)COC1=C(C)C=CC=C1C OCULOLABMGTDLY-UHFFFAOYSA-N 0.000 claims 1
- HUTQLLQMTLVQSP-UHFFFAOYSA-N n-[4-[2-[1-(2,6-dimethylphenoxy)propan-2-yl-methylamino]ethyl]phenyl]methanesulfonamide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)C(C)COC1=C(C)C=CC=C1C HUTQLLQMTLVQSP-UHFFFAOYSA-N 0.000 claims 1
- OPGZZMHCZHUKSZ-UHFFFAOYSA-N n-[4-[2-[1-(2,6-dimethylphenoxy)propan-2-ylamino]ethyl]phenyl]methanesulfonamide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCNC(C)COC1=C(C)C=CC=C1C OPGZZMHCZHUKSZ-UHFFFAOYSA-N 0.000 claims 1
- HUTQLLQMTLVQSP-GOSISDBHSA-N n-[4-[2-[[(2r)-1-(2,6-dimethylphenoxy)propan-2-yl]-methylamino]ethyl]phenyl]methanesulfonamide Chemical compound C([C@@H](C)N(C)CCC=1C=CC(NS(C)(=O)=O)=CC=1)OC1=C(C)C=CC=C1C HUTQLLQMTLVQSP-GOSISDBHSA-N 0.000 claims 1
- HUTQLLQMTLVQSP-SFHVURJKSA-N n-[4-[2-[[(2s)-1-(2,6-dimethylphenoxy)propan-2-yl]-methylamino]ethyl]phenyl]methanesulfonamide Chemical compound C([C@H](C)N(C)CCC=1C=CC(NS(C)(=O)=O)=CC=1)OC1=C(C)C=CC=C1C HUTQLLQMTLVQSP-SFHVURJKSA-N 0.000 claims 1
- INSYVJKBNYOJNR-UHFFFAOYSA-N n-[4-[2-[methyl-[2-(2-methylphenoxy)ethyl]amino]ethyl]phenyl]methanesulfonamide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=CC=C1C INSYVJKBNYOJNR-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 72
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
- 230000000694 effects Effects 0.000 description 30
- 239000007858 starting material Substances 0.000 description 29
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 125000006519 CCH3 Chemical group 0.000 description 19
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- 239000000126 substance Substances 0.000 description 12
- 239000003416 antiarrhythmic agent Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
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- 239000000047 product Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 230000001536 pro-arrhythmogenic effect Effects 0.000 description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- 229940126121 sodium channel inhibitor Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 229960002872 tocainide Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9702411A HUP9702411A2 (hu) | 1997-12-11 | 1997-12-11 | Fenoxi-alkil-amin-származékok és a vegyületeket tartalmazó antiaritmiás hatású gyógyszerkészítmények |
| PCT/HU1998/000101 WO1999029655A1 (en) | 1997-12-11 | 1998-12-10 | Novel antiarrhythmic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69806411D1 DE69806411D1 (de) | 2002-08-08 |
| DE69806411T2 true DE69806411T2 (de) | 2003-03-20 |
Family
ID=89995855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69806411T Expired - Lifetime DE69806411T2 (de) | 1997-12-11 | 1998-12-10 | Neue antiarrythmische verbindungen |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6265445B1 (https=) |
| EP (1) | EP1037871B1 (https=) |
| JP (1) | JP2001525388A (https=) |
| KR (1) | KR100576905B1 (https=) |
| CN (1) | CN1140498C (https=) |
| AT (1) | ATE220058T1 (https=) |
| AU (1) | AU738672B2 (https=) |
| BR (1) | BR9814270A (https=) |
| CA (1) | CA2313191A1 (https=) |
| DE (1) | DE69806411T2 (https=) |
| DK (1) | DK1037871T3 (https=) |
| ES (1) | ES2179547T3 (https=) |
| HU (1) | HUP9702411A2 (https=) |
| IL (1) | IL136659A (https=) |
| NO (1) | NO20002946L (https=) |
| NZ (1) | NZ504982A (https=) |
| PL (1) | PL190788B1 (https=) |
| PT (1) | PT1037871E (https=) |
| RU (1) | RU2193024C2 (https=) |
| SK (1) | SK284284B6 (https=) |
| UA (1) | UA61979C2 (https=) |
| WO (1) | WO1999029655A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19956786A1 (de) * | 1999-11-25 | 2001-05-31 | Basf Ag | Verfahren zur Herstellung optisch aktiver Amine |
| US20030119406A1 (en) | 2001-12-20 | 2003-06-26 | Abuto Francis Paul | Targeted on-line stabilized absorbent structures |
| AU2002357560A1 (en) * | 2002-04-26 | 2003-11-10 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Sulfamidophenylalkylamines and their production and use |
| CN102603543B (zh) * | 2012-04-09 | 2014-07-02 | 佛山普正医药科技有限公司 | 一种盐酸美西律的生产方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD146749A3 (de) * | 1977-12-01 | 1981-03-04 | Dieter Lehmann | Verfahren zur herstellung von phenoxyalkanolamin-derivaten |
| EG18188A (en) * | 1986-05-01 | 1992-09-30 | Pfizer Ltd | Process for preparation anti-arhythmia agents |
| NO179246C (no) * | 1991-11-20 | 1996-09-04 | Sankyo Co | Aromatiske amino-alkoholderivater og mellomprodukter til fremstilling derav |
| JPH06107614A (ja) * | 1992-09-26 | 1994-04-19 | Arakusu:Kk | アリールスルホン酸アミド類またはアリールカルボン酸アミド類及びそれらの薬剤として許容される酸付加塩及びその製造法並びにそれを有効成分とする抗消化性潰瘍剤 |
-
1997
- 1997-12-11 HU HU9702411A patent/HUP9702411A2/hu unknown
-
1998
- 1998-10-12 UA UA2000063362A patent/UA61979C2/uk unknown
- 1998-12-10 EP EP98961331A patent/EP1037871B1/en not_active Expired - Lifetime
- 1998-12-10 PT PT98961331T patent/PT1037871E/pt unknown
- 1998-12-10 DE DE69806411T patent/DE69806411T2/de not_active Expired - Lifetime
- 1998-12-10 WO PCT/HU1998/000101 patent/WO1999029655A1/en not_active Ceased
- 1998-12-10 US US09/555,602 patent/US6265445B1/en not_active Expired - Fee Related
- 1998-12-10 PL PL341107A patent/PL190788B1/pl not_active IP Right Cessation
- 1998-12-10 SK SK879-2000A patent/SK284284B6/sk not_active IP Right Cessation
- 1998-12-10 DK DK98961331T patent/DK1037871T3/da active
- 1998-12-10 CA CA002313191A patent/CA2313191A1/en not_active Abandoned
- 1998-12-10 JP JP2000524252A patent/JP2001525388A/ja active Pending
- 1998-12-10 AT AT98961331T patent/ATE220058T1/de not_active IP Right Cessation
- 1998-12-10 AU AU16789/99A patent/AU738672B2/en not_active Ceased
- 1998-12-10 IL IL13665998A patent/IL136659A/en not_active IP Right Cessation
- 1998-12-10 CN CNB988135779A patent/CN1140498C/zh not_active Expired - Fee Related
- 1998-12-10 RU RU2000118325/04A patent/RU2193024C2/ru not_active IP Right Cessation
- 1998-12-10 BR BR9814270-4A patent/BR9814270A/pt not_active Application Discontinuation
- 1998-12-10 NZ NZ504982A patent/NZ504982A/en unknown
- 1998-12-10 ES ES98961331T patent/ES2179547T3/es not_active Expired - Lifetime
- 1998-12-10 KR KR1020007006348A patent/KR100576905B1/ko not_active Expired - Fee Related
-
2000
- 2000-06-08 NO NO20002946A patent/NO20002946L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL136659A0 (en) | 2001-06-14 |
| CN1284941A (zh) | 2001-02-21 |
| KR100576905B1 (ko) | 2006-05-03 |
| CA2313191A1 (en) | 1999-06-17 |
| SK8792000A3 (en) | 2001-02-12 |
| IL136659A (en) | 2004-08-31 |
| HU9702411D0 (en) | 1998-03-02 |
| NO20002946L (no) | 2000-08-07 |
| HK1033937A1 (en) | 2001-10-05 |
| AU738672B2 (en) | 2001-09-20 |
| US6265445B1 (en) | 2001-07-24 |
| ES2179547T3 (es) | 2003-01-16 |
| JP2001525388A (ja) | 2001-12-11 |
| PT1037871E (pt) | 2002-11-29 |
| NO20002946D0 (no) | 2000-06-08 |
| WO1999029655A1 (en) | 1999-06-17 |
| DE69806411D1 (de) | 2002-08-08 |
| PL190788B1 (pl) | 2006-01-31 |
| BR9814270A (pt) | 2001-10-16 |
| RU2193024C2 (ru) | 2002-11-20 |
| NZ504982A (en) | 2002-07-26 |
| ATE220058T1 (de) | 2002-07-15 |
| CN1140498C (zh) | 2004-03-03 |
| KR20010032996A (ko) | 2001-04-25 |
| PL341107A1 (en) | 2001-03-26 |
| HUP9702411A2 (hu) | 2000-03-28 |
| EP1037871B1 (en) | 2002-07-03 |
| DK1037871T3 (da) | 2002-10-14 |
| EP1037871A1 (en) | 2000-09-27 |
| AU1678999A (en) | 1999-06-28 |
| SK284284B6 (sk) | 2005-01-03 |
| UA61979C2 (en) | 2003-12-15 |
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| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SZENT-GYOERGYI ALBERT ORVOSTUDOMANYI EGYETEM, SZEGE Owner name: IVAX DRUG RESEARCH INSTITUTE LTD., BUDAPEST, HU |