RU2004118423A - Производные бензотиазола в качестве лигандов рецептора аденозина - Google Patents
Производные бензотиазола в качестве лигандов рецептора аденозина Download PDFInfo
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- RU2004118423A RU2004118423A RU2004118423/04A RU2004118423A RU2004118423A RU 2004118423 A RU2004118423 A RU 2004118423A RU 2004118423/04 A RU2004118423/04 A RU 2004118423/04A RU 2004118423 A RU2004118423 A RU 2004118423A RU 2004118423 A RU2004118423 A RU 2004118423A
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- Prior art keywords
- compound
- compounds
- formula
- alkyl
- morpholin
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- 102000009346 Adenosine receptors Human genes 0.000 title claims 2
- 108050000203 Adenosine receptors Proteins 0.000 title claims 2
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- DOIKFFGWUPLXGA-UHFFFAOYSA-N 4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-amine Chemical compound C1=2SC(N)=NC=2C(OC)=CC=C1N1CCOCC1 DOIKFFGWUPLXGA-UHFFFAOYSA-N 0.000 claims 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 1
- NXKFBEPAUVJGMW-UHFFFAOYSA-N CCC(CN(C=CC(C(O)=O)=C1)C1=O)=O.COC(C1=C2SC(N)=N1)=CC=C2N1CCOCC1 Chemical class CCC(CN(C=CC(C(O)=O)=C1)C1=O)=O.COC(C1=C2SC(N)=N1)=CC=C2N1CCOCC1 NXKFBEPAUVJGMW-UHFFFAOYSA-N 0.000 claims 1
- MODUQJKJSBFFIW-UHFFFAOYSA-N COC(C1=C2SC(N)=N1)=CC=C2N1CCOCC1.OC(C(C=CN1CC(N2CCOCC2)=O)=CC1=O)=O Chemical compound COC(C1=C2SC(N)=N1)=CC=C2N1CCOCC1.OC(C(C=CN1CC(N2CCOCC2)=O)=CC1=O)=O MODUQJKJSBFFIW-UHFFFAOYSA-N 0.000 claims 1
- LWUOEKRGLCOSJJ-UHFFFAOYSA-N COC(C1=C2SC(N)=N1)=CC=C2N1CCOCC1.OC(C(C=CN1CC2=CC=CC=C2)=CC1=O)=O Chemical compound COC(C1=C2SC(N)=N1)=CC=C2N1CCOCC1.OC(C(C=CN1CC2=CC=CC=C2)=CC1=O)=O LWUOEKRGLCOSJJ-UHFFFAOYSA-N 0.000 claims 1
- HXUXPILGYZCSAZ-UHFFFAOYSA-N COC1=CC=C(C2=C1N=C(S2)C=2C(N(C=CC2C(=O)N)CC(N(C)C)=O)=O)N2CCOCC2 Chemical compound COC1=CC=C(C2=C1N=C(S2)C=2C(N(C=CC2C(=O)N)CC(N(C)C)=O)=O)N2CCOCC2 HXUXPILGYZCSAZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229960005305 adenosine Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- NHENNNNIWFADHU-UHFFFAOYSA-N ethyl 2-[4-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]-2-oxopyridin-1-yl]acetate Chemical compound O=C1N(CC(=O)OCC)C=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 NHENNNNIWFADHU-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/04—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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/18—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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Anesthesiology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (19)
1. Соединения общей формулы
где R означает фенил, пиридин-2-ил, -С(O)-O-(низш.)алкил, -С(O)-(низш.)алкил, -С(O)-морфолинил, -C(O)-NR'2, -(CH2)n-NR'2 или -(СН2)n-O-(низш.)алкил, а R' означает водород или (низш.)алкил, и их фармацевтически приемлемые кислотно-аддитивные соли.
2. Соединения формулы I по п.1, где R означает фенил.
3. Соединения формулы I по п.2, где соединение означает (4-метокси-7-морфолин-4-илбензотиазол-2-ил)амид 1-бензил-2-оксо-1,2-дигидропиридин-4-карбоновой кислоты.
4. Соединения по п.1, где R означает -С(O)O-(низш.)алкил.
5. Соединения по п.4, где соединение означает этиловый эфир [4-(4-метокси-7-морфолин-4-илбензотиазол-2-илкарбамоил)-2-оксо-2Н-пиридин-1-ил]уксусной кислоты.
6. Соединения по п.1, где R означает -С(O)-(низш,)алкил.
7. Соединения по п.6, где соединение означает (4-метокси-7-морфолин-4-илбензотиазол-2-ил)амид 2-оксо-1-(2-оксобутил)-1,2-дигидропиридин-4-карбоновой кислоты.
8. Соединения по п.1, где R означает пиридинил.
9. Соединения по п.8, где соединение означает (4-метокси-7-морфолин-4-илбензотиазол-2-ил)амид 2-оксо-1-ïиридин-2-илметил-1,2-дигидропиридин-4-карбоновой кислоты.
10. Соединения по п.1, где R означает -С(O)-морфолинил.
11. Соединения по п.10, где соединение означает (4-метокси-7-морфолин-4-илбензотиазол-2-ил)амид 1-(2-морфолин-4-ил-2-оксоэтил)-2-оксо-1,2-дигидропиридин-4-карбоновой кислоты.
12. Соединения по п.1, где R означает -C(O)-NR'2.
13. Соединения по п.12, где соединение означает (4-метокси-7-морфолин-4-илбензотиазол-2-ил)амид 1-диметилкарбамоилметил-2-оксо-1,2-дигидропиридин-4-карбоновой кислоты.
14. Способ получения соединения формулы I по пп.1-13, включающий
а) взаимодействие соединения формулы
с соединением формулы
с образованием соединения формулы
где R означает фенил, пиридил, -С(O)O-(низш.)алкил или -С(O)-(низш.)алкил, или
б) взаимодействие соединения формулы
с соединением формулы
с образованием соединения формулы
где R означает -С(O)-морфолинил, -(СН2)n-O-(низш.)алкил, -(CH2)nNR'2 или -C(O)NR'2, и
при необходимости превращение полученных соединений в фармацевтически приемлемые кислотно-аддитивные соли.
15. Соединение по любому из пп.1-13, полученное способом по п.14 или эквивалентным способом.
16. Лекарственное средство, содержащее одно или более соединений по любому из пп.1-13 и фармацевтически приемлемые эксципиенты.
17. Лекарственное средство по п.16 для лечения заболеваний, опосредованных рецептором аденозина.
18. Применение соединения по любому из пп.1-13 для лечения заболеваний.
19. Применение соединения по любому из пп.1-13 для получения соответствующих лекарственных препаратов, предназначенных для лечения заболеваний, опосредованных аденозиновым рецептором А2A.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01127313 | 2001-11-19 | ||
| EP01127313.3 | 2001-11-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004118423A true RU2004118423A (ru) | 2006-01-10 |
| RU2295523C2 RU2295523C2 (ru) | 2007-03-20 |
Family
ID=8179264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004118423/04A RU2295523C2 (ru) | 2001-11-19 | 2002-11-09 | Производные бензотиазола в качестве лигандов рецептора аденозина и лекарственное средство |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6599901B1 (ru) |
| EP (1) | EP1448196B1 (ru) |
| JP (1) | JP4216192B2 (ru) |
| KR (1) | KR100577109B1 (ru) |
| CN (1) | CN100346792C (ru) |
| AR (1) | AR037528A1 (ru) |
| AT (1) | ATE306265T1 (ru) |
| AU (1) | AU2002366194B8 (ru) |
| BR (1) | BR0214221A (ru) |
| CA (1) | CA2467551A1 (ru) |
| DE (1) | DE60206652T2 (ru) |
| ES (1) | ES2249639T3 (ru) |
| GT (1) | GT200200233A (ru) |
| MX (1) | MXPA04004683A (ru) |
| PA (1) | PA8557901A1 (ru) |
| PE (1) | PE20030715A1 (ru) |
| PL (1) | PL369470A1 (ru) |
| RU (1) | RU2295523C2 (ru) |
| TW (1) | TW200407137A (ru) |
| UY (1) | UY27543A1 (ru) |
| WO (1) | WO2003043634A1 (ru) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE521512C2 (sv) | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| US6727247B2 (en) * | 2001-12-10 | 2004-04-27 | Hoffman-La Roche Inc. | Substituted benzothiazole amide derivatives |
| ATE359075T1 (de) | 2002-12-20 | 2007-05-15 | Niconovum Ab | Chemisch und physikalisch stabiles teilchenförmiges material enthaltend nikotin und microcrystalline cellulose |
| RU2006112847A (ru) | 2003-09-19 | 2007-11-10 | Ф. Хоффманн-Ля Рош Аг (Ch) | Производные тиазолопиридина в качестве лигандов аденозинового рецептора |
| WO2005044793A2 (en) | 2003-10-31 | 2005-05-19 | Takeda Pharmaceutical Company Limited | Nitrogen-containing fused heterocyclic compounds |
| CN1989139B (zh) * | 2004-07-22 | 2010-05-12 | 弗·哈夫曼-拉罗切有限公司 | 苯并噻唑衍生物 |
| EP1773795A1 (en) * | 2004-07-22 | 2007-04-18 | F.Hoffmann-La Roche Ag | Substituted benzothiazoles |
| ES2273599B1 (es) * | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| AU2007224584A1 (en) | 2006-03-16 | 2007-09-20 | Niconovum Ab | Improved snuff composition |
| AU2007322269A1 (en) * | 2006-10-11 | 2008-05-29 | Alpharma Pharmaceuticals, Llc | Pharmaceutical compositions |
| SI2144905T1 (sl) * | 2007-04-04 | 2013-03-29 | Merck Sharp & Dohme Corp. | Terapevtska sredstva |
| US9549909B2 (en) | 2013-05-03 | 2017-01-24 | The Katholieke Universiteit Leuven | Method for the treatment of dravet syndrome |
| KR102688278B1 (ko) | 2015-12-22 | 2024-07-26 | 조게닉스 인터내셔널 리미티드 | 펜플루라민 조성물 및 그 제조 방법 |
| JP2019507111A (ja) | 2015-12-22 | 2019-03-14 | ゾゲニクス インターナショナル リミテッド | 代謝抵抗性フェンフルラミン類縁体およびその使用法 |
| CA3032996C (en) | 2016-08-24 | 2025-05-06 | Zogenix International Ltd | Formulation for inhibiting formation of 5-ht 2b agonists and methods of using same |
| US10682317B2 (en) | 2017-09-26 | 2020-06-16 | Zogenix International Limited | Ketogenic diet compatible fenfluramine formulation |
| CA3097335A1 (en) | 2018-05-11 | 2019-11-14 | Zogenix International Limited | Compositions and methods for treating seizure-induced sudden death |
| WO2019241005A1 (en) | 2018-06-14 | 2019-12-19 | Zogenix International Limited | Compositions and methods for treating respiratory depression with fenfluramine |
| AU2019384963B2 (en) | 2018-11-19 | 2022-05-26 | Zogenix International Limited | Methods of treating Rett syndrome using fenfluramine |
| DE102019110904B4 (de) | 2019-04-26 | 2022-01-20 | Helmholtz-Zentrum Dresden - Rossendorf E. V. | N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)-acetamid-Derivate und deren Verwendung |
| US11612574B2 (en) | 2020-07-17 | 2023-03-28 | Zogenix International Limited | Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0113219B1 (en) | 1982-12-21 | 1987-11-19 | Johnsen & Jorgensen (Plastics) Limited | Dispensing container |
| IL90337A0 (en) * | 1988-05-24 | 1989-12-15 | Pfizer | Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents |
| CN1234358C (zh) * | 2000-06-21 | 2006-01-04 | 弗·哈夫曼-拉罗切有限公司 | 苯并噻唑衍生物 |
-
2002
- 2002-11-05 US US10/288,531 patent/US6599901B1/en not_active Expired - Fee Related
- 2002-11-09 EP EP02803360A patent/EP1448196B1/en not_active Expired - Lifetime
- 2002-11-09 AT AT02803360T patent/ATE306265T1/de not_active IP Right Cessation
- 2002-11-09 PL PL02369470A patent/PL369470A1/xx not_active Application Discontinuation
- 2002-11-09 WO PCT/EP2002/012543 patent/WO2003043634A1/en not_active Ceased
- 2002-11-09 MX MXPA04004683A patent/MXPA04004683A/es active IP Right Grant
- 2002-11-09 DE DE60206652T patent/DE60206652T2/de not_active Expired - Fee Related
- 2002-11-09 CA CA002467551A patent/CA2467551A1/en not_active Abandoned
- 2002-11-09 ES ES02803360T patent/ES2249639T3/es not_active Expired - Lifetime
- 2002-11-09 BR BR0214221-0A patent/BR0214221A/pt not_active IP Right Cessation
- 2002-11-09 CN CNB028228901A patent/CN100346792C/zh not_active Expired - Fee Related
- 2002-11-09 KR KR1020047007646A patent/KR100577109B1/ko not_active Expired - Fee Related
- 2002-11-09 JP JP2003545315A patent/JP4216192B2/ja not_active Expired - Fee Related
- 2002-11-09 RU RU2004118423/04A patent/RU2295523C2/ru not_active IP Right Cessation
- 2002-11-09 AU AU2002366194A patent/AU2002366194B8/en not_active Ceased
- 2002-11-14 TW TW091133382A patent/TW200407137A/zh unknown
- 2002-11-14 PA PA20028557901A patent/PA8557901A1/es unknown
- 2002-11-15 AR ARP020104398A patent/AR037528A1/es not_active Application Discontinuation
- 2002-11-15 PE PE2002001103A patent/PE20030715A1/es not_active Application Discontinuation
- 2002-11-18 UY UY27543A patent/UY27543A1/es not_active Application Discontinuation
- 2002-11-18 GT GT200200233A patent/GT200200233A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR037528A1 (es) | 2004-11-17 |
| CN100346792C (zh) | 2007-11-07 |
| BR0214221A (pt) | 2004-09-21 |
| CN1589146A (zh) | 2005-03-02 |
| DE60206652D1 (de) | 2006-02-23 |
| US6599901B1 (en) | 2003-07-29 |
| ATE306265T1 (de) | 2005-10-15 |
| CA2467551A1 (en) | 2003-05-30 |
| WO2003043634A1 (en) | 2003-05-30 |
| DE60206652T2 (de) | 2006-06-22 |
| TW200407137A (en) | 2004-05-16 |
| PL369470A1 (en) | 2005-04-18 |
| MXPA04004683A (es) | 2004-08-12 |
| AU2002366194B8 (en) | 2006-11-16 |
| JP2005515980A (ja) | 2005-06-02 |
| JP4216192B2 (ja) | 2009-01-28 |
| AU2002366194B2 (en) | 2006-10-26 |
| UY27543A1 (es) | 2003-05-30 |
| ES2249639T3 (es) | 2006-04-01 |
| AU2002366194A1 (en) | 2003-06-10 |
| EP1448196A1 (en) | 2004-08-25 |
| PA8557901A1 (es) | 2003-06-30 |
| EP1448196B1 (en) | 2005-10-12 |
| RU2295523C2 (ru) | 2007-03-20 |
| KR20050044537A (ko) | 2005-05-12 |
| KR100577109B1 (ko) | 2006-05-10 |
| GT200200233A (es) | 2003-06-17 |
| PE20030715A1 (es) | 2003-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20091110 |