CZ285799B6 - Indolové deriváty, způsob jejich výroby, jejich použití pro výrobu farmaceutických prostředků a farmaceutické prostředky s jejich obsahem - Google Patents
Indolové deriváty, způsob jejich výroby, jejich použití pro výrobu farmaceutických prostředků a farmaceutické prostředky s jejich obsahem Download PDFInfo
- Publication number
- CZ285799B6 CZ285799B6 CZ942543A CZ254394A CZ285799B6 CZ 285799 B6 CZ285799 B6 CZ 285799B6 CZ 942543 A CZ942543 A CZ 942543A CZ 254394 A CZ254394 A CZ 254394A CZ 285799 B6 CZ285799 B6 CZ 285799B6
- Authority
- CZ
- Czechia
- Prior art keywords
- formula
- ethenyl
- dichloroindole
- group
- compound
- Prior art date
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- 150000002475 indoles Chemical class 0.000 title claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
- 229940054051 antipsychotic indole derivative Drugs 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims description 52
- 238000000034 method Methods 0.000 title claims description 27
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 150000002148 esters Chemical class 0.000 claims abstract description 30
- 230000000694 effects Effects 0.000 claims abstract description 10
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims abstract description 9
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims abstract description 9
- 230000002461 excitatory amino acid Effects 0.000 claims abstract description 9
- 239000003257 excitatory amino acid Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 141
- -1 hydroxy, methoxy, ethoxy Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
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- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 7
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
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- 125000006018 1-methyl-ethenyl group Chemical group 0.000 claims description 3
- GGFGLRLJUIGKJY-DUXPYHPUSA-N 4,6-dichloro-3-[(e)-3-(2,4-difluoroanilino)-3-oxoprop-1-enyl]-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC(Cl)=CC(Cl)=C2C=1\C=C\C(=O)NC1=CC=C(F)C=C1F GGFGLRLJUIGKJY-DUXPYHPUSA-N 0.000 claims description 3
- DHXISZKSSIWRLH-UHFFFAOYSA-N 4,6-dichloro-1h-indole-2-carboxylic acid Chemical compound C1=C(Cl)C=C2NC(C(=O)O)=CC2=C1Cl DHXISZKSSIWRLH-UHFFFAOYSA-N 0.000 claims description 2
- XLMJSBMZZPMBBS-BQYQJAHWSA-N 4,6-dichloro-3-[(e)-3-(4-ethoxyanilino)-3-oxoprop-1-enyl]-1h-indole-2-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1NC(=O)\C=C\C1=C(C(O)=O)NC2=CC(Cl)=CC(Cl)=C12 XLMJSBMZZPMBBS-BQYQJAHWSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001041 indolyl group Chemical group 0.000 claims description 2
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- 239000004471 Glycine Substances 0.000 abstract description 6
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 abstract description 6
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- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 5
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- DGXMYSHVJMOWMA-CMDGGOBGSA-N ethyl 3-[(e)-3-anilino-3-oxoprop-1-enyl]-4,6-dichloro-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC(Cl)=CC(Cl)=C2C=1\C=C\C(=O)NC1=CC=CC=C1 DGXMYSHVJMOWMA-CMDGGOBGSA-N 0.000 description 4
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Classifications
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- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
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- 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
- A61P25/28—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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929208492A GB9208492D0 (en) | 1992-04-16 | 1992-04-16 | Heterocyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ254394A3 CZ254394A3 (en) | 1995-07-12 |
| CZ285799B6 true CZ285799B6 (cs) | 1999-11-17 |
Family
ID=10714220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ942543A CZ285799B6 (cs) | 1992-04-16 | 1993-04-15 | Indolové deriváty, způsob jejich výroby, jejich použití pro výrobu farmaceutických prostředků a farmaceutické prostředky s jejich obsahem |
Country Status (41)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ300548B6 (cs) * | 1998-03-26 | 2009-06-10 | Astellas Pharma Inc. | Prostredek s prodlouženým uvolnením makrolidové slouceniny |
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| GB9304500D0 (en) * | 1993-03-05 | 1993-04-21 | Glaxo Spa | Heterocyclic compounds |
| KR100314482B1 (ko) * | 1993-05-27 | 2002-02-28 | 메렐 파마슈티칼스 인크. | 3-(인돌-3-일)프로페노산유도체 |
| US5519048A (en) * | 1993-05-27 | 1996-05-21 | Merrell Pharmaceuticals Inc. | 3-(indol-3-yl)-propenoic acid derivatives and pharmaceutical compositions thereof |
| GB9319243D0 (en) * | 1993-09-17 | 1993-11-03 | Glaxo Spa | Heterocyclic compounds |
| GB9321221D0 (en) * | 1993-10-14 | 1993-12-01 | Glaxo Spa | Heterocyclic compounds |
| TW280819B (enExample) * | 1993-11-17 | 1996-07-11 | Sumitomo Pharma | |
| US5563157B1 (en) | 1994-10-31 | 1999-02-02 | Hoecst Marion Roussel Inc | Heterocycle substituted propenoic acid derivatives and pharmaceutical compositions thereof |
| GB9502695D0 (en) * | 1995-02-11 | 1995-03-29 | Glaxo Spa | Pharmaceutical composition |
| GB9504361D0 (en) * | 1995-03-04 | 1995-04-26 | Glaxo Spa | Heterocyclic compounds |
| US6030968A (en) * | 1996-09-17 | 2000-02-29 | The Regents Of The University Of California | Positive AMPA receptor modulation to enhance brain neurotrophic factor expression |
| IL129187A0 (en) * | 1996-09-30 | 2000-02-17 | Hoechst Marion Roussel Inc | NMDA (N-methyl-D-aspartate) antagonists |
| US5922752A (en) * | 1997-06-11 | 1999-07-13 | Hoechst Marion Roussell, Inc. | NMDA (n-methyl-d-aspartate) antagonists |
| BR0112881A (pt) * | 2000-07-31 | 2003-07-01 | Dainippon Pharmaceutical Co | Remédios para demência contendo derivados de 2-aril-8-oxodihidropurina como o ingrediente ativo |
| US20030162825A1 (en) * | 2001-11-09 | 2003-08-28 | Sepracor Inc. | D-amino acid oxidase inhibitors for learning and memory |
| EP1463714A4 (en) * | 2001-12-10 | 2005-10-19 | Amgen Inc | VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS |
| PA8579701A1 (es) * | 2002-08-23 | 2005-05-24 | Pfizer Prod Inc | Profarmaco inhibidor de beta-lactamasa |
| DE10306202A1 (de) | 2003-02-13 | 2004-08-26 | Grünenthal GmbH | Arzneimittel enthaltend substituierte 2-Aryl-Aminoessigsäure-Verbindungen und/oder substituierte 2-Heteroaryl-Aminoessigsäure-Verbindungen |
| JP2006526612A (ja) * | 2003-06-05 | 2006-11-24 | ファイザー・プロダクツ・インク | ベータ−ラクタマーゼ阻害剤・プロドラッグ |
| RU2247563C1 (ru) * | 2003-06-16 | 2005-03-10 | Пятигорская государственная фармацевтическая академия | Способ получения твердой лекарственной формы, содержащей глюкозамина гидрохлорид |
| JP4864719B2 (ja) * | 2003-11-26 | 2012-02-01 | ファイザー・プロダクツ・インク | Ｇｓｋ−３インヒビターとしてのアミノピラゾール誘導体 |
| AU2004312530A1 (en) * | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole DAAO inhibitors |
| RU2281755C2 (ru) * | 2004-04-19 | 2006-08-20 | Пятигорская государственная фармацевтическая академия | Композиция - лекарственная форма противоартрозного средства глюкозамина гидрохлорида для ректального применения |
| US20060002999A1 (en) * | 2004-06-17 | 2006-01-05 | Forest Laboratories, Inc. | Immediate release formulations of 1-aminocyclohexane compounds, memantine and neramexane |
| WO2007006003A2 (en) | 2005-07-06 | 2007-01-11 | Sepracor Inc. | Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders |
| JP5438975B2 (ja) * | 2006-01-06 | 2014-03-12 | サノビオン ファーマシューティカルズ インク | テトラロン系モノアミン再取り込み阻害剤 |
| KR101294014B1 (ko) | 2006-01-06 | 2013-08-09 | 선오비온 파마슈티컬스 인코포레이티드 | 모노아민 재흡수 저해제로서의 시클로알킬아민 |
| CA2648121C (en) | 2006-03-31 | 2013-08-06 | Sepracor Inc. | Preparation of chiral amides and amines |
| US7884124B2 (en) * | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7579370B2 (en) * | 2006-06-30 | 2009-08-25 | Sepracor Inc. | Fused heterocycles |
| US20080082066A1 (en) * | 2006-10-02 | 2008-04-03 | Weyerhaeuser Co. | Crosslinked carboxyalkyl cellulose fibers having non-permanent and temporary crosslinks |
| EP1942104A1 (en) | 2006-12-20 | 2008-07-09 | sanofi-aventis | Heteroarylcyclopropanecarboxamides and their use as pharmaceuticals |
| MX2009007410A (es) | 2007-01-18 | 2009-09-09 | Sepracor Inc | Inhibidores de d-aminoacido oxidasa. |
| US7902252B2 (en) * | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| BRPI0811639A2 (pt) | 2007-05-31 | 2014-09-30 | Sepracor Inc | Cicloaquilaminas fenil substituídas como inibidores da recaptação de monoamina |
| WO2009151498A2 (en) * | 2008-03-28 | 2009-12-17 | Forest Laboratories Holdings Limited | Memantine formulations |
| WO2010017418A1 (en) * | 2008-08-07 | 2010-02-11 | Sepracor Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
| CA2755118A1 (en) * | 2009-03-10 | 2010-09-16 | Santen Pharmaceutical Co., Ltd. | Preventive or therapeutic agents for optic nerve disorders comprising 4,6-dichloro-1h-indole-2-carboxylic acid derivatives or salts thereof as active ingredients |
| WO2011017634A2 (en) * | 2009-08-07 | 2011-02-10 | Sepracore Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
| US9737531B2 (en) | 2012-07-12 | 2017-08-22 | Glytech, Llc | Composition and method for treatment of depression and psychosis in humans |
| US9868975B2 (en) | 2014-04-30 | 2018-01-16 | Yufeng Jane Tseng | Use of known compounds as D-amino acid oxidase inhibitors |
| CA3207747A1 (en) | 2016-09-14 | 2018-03-22 | Yufeng Jane Tseng | Novel substituted benzimidazole derivatives as d-amino acid oxidase (daao) inhibitors |
| RU2020100230A (ru) | 2017-06-12 | 2021-07-13 | Глитек Ллс. | Лечение депрессии антагонистами nmda и антагонистами d2/5-ht2a или селективными антагонистами 5-нт2a |
| CN112707874A (zh) * | 2020-12-29 | 2021-04-27 | 广东中科药物研究有限公司 | 一种抗病毒化合物及其制备方法 |
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| US3010971A (en) * | 1960-08-04 | 1961-11-28 | Smith Kline French Lab | Cyclopropylamine derivatives and processes for their preparation |
| DK500285A (da) * | 1984-11-02 | 1986-05-03 | Glaxo Group Ltd | Cephalosporinantibiotika |
| US4960786A (en) * | 1989-04-24 | 1990-10-02 | Merrell Dow Pharmaceuticals Inc. | Excitatory amino acid antagonists |
| JPH0347123A (ja) * | 1989-05-05 | 1991-02-28 | G D Searle & Co | インドール―２―カルボキシレート化合物類を含有するｃｎｓ疾患治療用組成物 |
| ES2088011T3 (es) * | 1990-07-16 | 1996-08-01 | Merrell Pharma Inc | Antagonistas de aminoacidos excitadores. |
| US5284862A (en) * | 1991-03-18 | 1994-02-08 | Warner-Lambert Company | Derivatives of 2-carboxyindoles having pharmaceutical activity |
| US5145845A (en) * | 1991-05-14 | 1992-09-08 | Warner-Lambert Co. | Substituted 2-carboxylindoles having pharmaceutical activity |
-
1992
- 1992-04-16 GB GB929208492A patent/GB9208492D0/en active Pending
-
1993
- 1993-04-14 ZA ZA932642A patent/ZA932642B/xx unknown
- 1993-04-15 AU AU36923/93A patent/AU666927B2/en not_active Ceased
- 1993-04-15 CN CN93105797A patent/CN1042331C/zh not_active Expired - Fee Related
- 1993-04-15 PL PL93305554A patent/PL176451B1/pl unknown
- 1993-04-15 BE BE9300371A patent/BE1006343A5/fr active
- 1993-04-15 MY MYPI93000690A patent/MY112232A/en unknown
- 1993-04-15 ES ES09300771A patent/ES2105924B1/es not_active Expired - Lifetime
- 1993-04-15 GB GB9307808A patent/GB2266091B/en not_active Expired - Fee Related
- 1993-04-15 MX MX9302195A patent/MX9302195A/es not_active IP Right Cessation
- 1993-04-15 US US08/047,429 patent/US5374648A/en not_active Expired - Fee Related
- 1993-04-15 CZ CZ942543A patent/CZ285799B6/cs not_active IP Right Cessation
- 1993-04-15 WO PCT/EP1993/000938 patent/WO1993021153A1/en not_active Ceased
- 1993-04-15 JP JP5517997A patent/JPH07505407A/ja active Pending
- 1993-04-15 NZ NZ247413A patent/NZ247413A/en unknown
- 1993-04-15 LU LU88248A patent/LU88248A1/fr unknown
- 1993-04-15 JP JP5088844A patent/JPH0649027A/ja active Pending
- 1993-04-15 CA CA002094073A patent/CA2094073A1/en not_active Abandoned
- 1993-04-15 KR KR1019940703668A patent/KR100264114B1/ko not_active Expired - Fee Related
- 1993-04-15 RU RU94045915A patent/RU2129544C1/ru active
- 1993-04-15 HU HU9402975A patent/HU217964B/hu not_active IP Right Cessation
- 1993-04-15 CH CH1133/93A patent/CH685630A5/fr not_active IP Right Cessation
- 1993-04-15 IS IS3994A patent/IS3994A/is unknown
- 1993-04-15 IT IT93RM000236A patent/IT1265325B1/it active IP Right Grant
- 1993-04-15 GR GR930100154A patent/GR1001619B/el not_active IP Right Cessation
- 1993-04-15 SK SK1241-94A patent/SK281941B6/sk unknown
- 1993-04-15 EP EP93201103A patent/EP0568136A1/en not_active Withdrawn
- 1993-04-15 IL IL105412A patent/IL105412A/en not_active IP Right Cessation
- 1993-04-15 US US08/046,947 patent/US5373018A/en not_active Expired - Fee Related
- 1993-04-15 FR FR9304452A patent/FR2690919B1/fr not_active Expired - Fee Related
- 1993-04-15 AT AT0075293A patent/AT403917B/de not_active IP Right Cessation
- 1993-04-15 RO RO94-01658A patent/RO113242B1/ro unknown
- 1993-04-15 DK DK043193A patent/DK169890B1/da active
- 1993-04-15 CA CA002094076A patent/CA2094076A1/en not_active Abandoned
- 1993-04-15 SE SE9301241A patent/SE504336C2/sv not_active IP Right Cessation
- 1993-04-15 US US08/047,430 patent/US5374649A/en not_active Expired - Fee Related
- 1993-04-15 CA CA002094075A patent/CA2094075A1/en not_active Abandoned
- 1993-04-16 AP APAP/P/1993/000524A patent/AP480A/en active
- 1993-04-16 GE GEAP19932602A patent/GEP19991704B/en unknown
- 1993-05-06 TW TW082103531A patent/TW224457B/zh active
-
1994
- 1994-10-10 OA OA60570A patent/OA10103A/en unknown
- 1994-10-12 FI FI944800A patent/FI106198B/fi active
- 1994-10-14 BG BG99111A patent/BG62136B1/bg unknown
- 1994-10-14 NO NO943913A patent/NO301879B1/no not_active IP Right Cessation
- 1994-12-08 US US08/351,762 patent/US5510367A/en not_active Expired - Fee Related
-
1995
- 1995-06-29 HU HU95P/P00538P patent/HU211826A9/hu unknown
-
1997
- 1997-04-22 BR BR1100323-5A patent/BR1100323A/pt active IP Right Grant
- 1997-06-26 HK HK95797A patent/HK95797A/xx not_active IP Right Cessation
-
1998
- 1998-04-30 CY CY9802038A patent/CY2038B1/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ300548B6 (cs) * | 1998-03-26 | 2009-06-10 | Astellas Pharma Inc. | Prostredek s prodlouženým uvolnením makrolidové slouceniny |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20020415 |