NO315704B1 - Heterocykliske forbindelser for inhibering av mavesyresekresjon, farmasöytiske preparater inneholdende slike forbindelser, fremgangsmåter forderes fremstilling, og deres anvendelse - Google Patents
Heterocykliske forbindelser for inhibering av mavesyresekresjon, farmasöytiske preparater inneholdende slike forbindelser, fremgangsmåter forderes fremstilling, og deres anvendelse Download PDFInfo
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- NO315704B1 NO315704B1 NO20002721A NO20002721A NO315704B1 NO 315704 B1 NO315704 B1 NO 315704B1 NO 20002721 A NO20002721 A NO 20002721A NO 20002721 A NO20002721 A NO 20002721A NO 315704 B1 NO315704 B1 NO 315704B1
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- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
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- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052816 inorganic phosphate Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
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- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
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- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 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
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9704404A SE9704404D0 (sv) | 1997-11-28 | 1997-11-28 | New compounds |
| PCT/SE1998/002091 WO1999028322A1 (en) | 1997-11-28 | 1998-11-18 | Heterocyclic compounds for inhibition of gastric acid secretion, processes for their preparation and pharmaceutical compositions thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20002721D0 NO20002721D0 (no) | 2000-05-26 |
| NO20002721L NO20002721L (no) | 2000-07-28 |
| NO315704B1 true NO315704B1 (no) | 2003-10-13 |
Family
ID=20409181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20002721A NO315704B1 (no) | 1997-11-28 | 2000-05-26 | Heterocykliske forbindelser for inhibering av mavesyresekresjon, farmasöytiske preparater inneholdende slike forbindelser, fremgangsmåter forderes fremstilling, og deres anvendelse |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6518270B1 (cs) |
| EP (1) | EP1042324B1 (cs) |
| JP (1) | JP2001525322A (cs) |
| KR (1) | KR20010032559A (cs) |
| CN (1) | CN1142933C (cs) |
| AR (1) | AR016972A1 (cs) |
| AT (1) | ATE233263T1 (cs) |
| AU (1) | AU752187C (cs) |
| BR (1) | BR9814755A (cs) |
| CA (1) | CA2311798A1 (cs) |
| CZ (1) | CZ292349B6 (cs) |
| DE (1) | DE69811735T2 (cs) |
| DK (1) | DK1042324T3 (cs) |
| EE (1) | EE04060B1 (cs) |
| ES (1) | ES2191356T3 (cs) |
| HU (1) | HUP0100601A3 (cs) |
| ID (1) | ID24730A (cs) |
| IL (1) | IL136145A0 (cs) |
| IS (1) | IS5486A (cs) |
| MY (1) | MY121032A (cs) |
| NO (1) | NO315704B1 (cs) |
| NZ (1) | NZ504355A (cs) |
| PL (1) | PL340920A1 (cs) |
| PT (1) | PT1042324E (cs) |
| RU (1) | RU2241000C2 (cs) |
| SE (1) | SE9704404D0 (cs) |
| SK (1) | SK283904B6 (cs) |
| TR (1) | TR200001530T2 (cs) |
| TW (1) | TW515798B (cs) |
| UA (1) | UA70932C2 (cs) |
| WO (1) | WO1999028322A1 (cs) |
| ZA (1) | ZA9810468B (cs) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2283012T3 (es) | 1996-01-04 | 2007-10-16 | Novartis Vaccines And Diagnostics, Inc. | Bacterioferritina de helicobacter pylori. |
| SE9704404D0 (sv) | 1997-11-28 | 1997-11-28 | Astra Ab | New compounds |
| PL201627B1 (pl) * | 1999-10-08 | 2009-04-30 | Affinium Pharmaceuticals | Nowa pochodna amidowa, zawierająca ją kompozycja farmaceutyczna oraz jej zastosowania |
| US7049310B2 (en) * | 2001-04-06 | 2006-05-23 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| JP2003119140A (ja) * | 2001-08-08 | 2003-04-23 | Sankyo Co Ltd | ピロロピリダジン化合物を含有する医薬 |
| JP2005530739A (ja) | 2002-04-19 | 2005-10-13 | セルラー ジェノミクス，インコーポレーテッド | イミダゾ［１，２−ａ］ピラジン−８−イルアミン、生成方法、および使用方法 |
| AU2003270489A1 (en) | 2002-09-09 | 2004-03-29 | Cellular Genomics, Inc. | 6-ARYL-IMIDAZO(1,2-a)PYRAZIN-8-YLAMINES, METHOD OF MAKING, AND METHOD OF USE THEREOF |
| AU2003266621A1 (en) * | 2002-09-25 | 2004-04-19 | Sankyo Company, Limited | Medicinal composition for treatment for or prevention of visceral pain |
| AU2003266622A1 (en) * | 2002-09-25 | 2004-04-19 | Sankyo Company, Limited | Medicinal composition for inhibiting increase in blood gastrin concentration |
| PT1575951E (pt) | 2002-12-06 | 2014-09-15 | Debiopharm Int Sa | Compostos heterocíclicos, métodos para os preparar e sua utilização em terapia |
| WO2004072081A1 (en) | 2003-02-10 | 2004-08-26 | Cellular Genomics, Inc. | Certain 8-heteroaryl-6-phenyl-imidazo[1,2-a]pyrazines as modulators of kinase activity |
| AR043002A1 (es) * | 2003-02-18 | 2005-07-13 | Altana Pharma Ag | Imidazopirazinas 6-substituidos |
| JP4880448B2 (ja) * | 2003-03-17 | 2012-02-22 | アフィナム ファーマシューティカルズ，インコーポレーテッド | 複数の抗生物質を含む組成物、及びそれを用いる方法 |
| WO2005014599A1 (en) | 2003-06-04 | 2005-02-17 | Cellular Genomics, Inc. | Imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of bruton’s tyrosine kinase by such compounds |
| WO2005005429A1 (en) | 2003-06-30 | 2005-01-20 | Cellular Genomics, Inc. | Certain heterocyclic substituted imidazo[1,2-a]pyrazin-8-ylamines and methods of inhibition of bruton’s tyrosine kinase by such compounds |
| US7259164B2 (en) | 2003-08-11 | 2007-08-21 | Cgi Pharmaceuticals, Inc. | Certain substituted imidazo[1,2-a]pyrazines, as modulators of kinase activity |
| CA2544325A1 (en) | 2003-11-03 | 2005-05-12 | Astrazeneca Ab | Imidazo [1,2-a] pyridine derivatives for the treatment of silent gastro-esophageal reflux |
| US8450307B2 (en) | 2004-06-04 | 2013-05-28 | Affinium Pharmaceuticals, Inc. | Therapeutic agents, and methods of making and using the same |
| WO2006011670A1 (ja) * | 2004-07-28 | 2006-02-02 | Takeda Pharmaceutical Company Limited | ピロロ［２，３－ｃ］ピリジン化合物、その製造方法および用途 |
| CA2575345A1 (en) * | 2004-08-02 | 2006-02-09 | Altana Pharma Ag | 5-substituted 1h-pyrrolo[3,2-b]pyridines |
| DK1784403T3 (da) * | 2004-09-03 | 2013-10-21 | Yuhan Corp | Pyrrolo[3,2-b]pyridinderivater samt fremgangsmåder til deres fremstilling |
| BRPI0514843A (pt) | 2004-09-03 | 2008-06-24 | Yuhan Corp | derivados de pirrolo[3,2-c] piridina e processos para a preparação dos mesmos |
| WO2006025716A1 (en) * | 2004-09-03 | 2006-03-09 | Yuhan Corporation | Pyrrolo[2,3-c]pyridine derivatives and processes for the preparation thereof |
| CA2579083C (en) * | 2004-09-03 | 2011-06-14 | Yuhan Corporation | Pyrrolo[3,2-c]pyridine derivatives and processes for the preparation thereof |
| US7777040B2 (en) | 2005-05-03 | 2010-08-17 | Cgi Pharmaceuticals, Inc. | Certain substituted ureas, as modulators of kinase activity |
| JP2009507032A (ja) | 2005-09-02 | 2009-02-19 | アボット・ラボラトリーズ | 新規なイミダゾ系複素環 |
| JP2009518399A (ja) * | 2005-12-05 | 2009-05-07 | アフィニウム ファーマシューティカルズ， インク． | Ｆａｂｉ阻害剤および抗菌剤としてのヘテロ環アクリルアミド化合物 |
| CN101516883A (zh) | 2006-06-06 | 2009-08-26 | 先灵公司 | 作为蛋白激酶抑制剂的咪唑并吡嗪化合物 |
| JP5468899B2 (ja) * | 2006-07-20 | 2014-04-09 | アフィニウム ファーマシューティカルズ， インク． | Ｆａｂｉインヒビターとしてのアクリルアミド誘導体 |
| US8263613B2 (en) * | 2007-02-16 | 2012-09-11 | Affinium Pharmaceuticals, Inc. | Salts, prodrugs and polymorphs of fab I inhibitors |
| NZ587039A (en) | 2008-02-13 | 2013-01-25 | Gilead Connecticut Inc | 6-aryl-imidazo[1, 2-a]pyrazine derivatives, method of making, and method of use thereof |
| US8450321B2 (en) | 2008-12-08 | 2013-05-28 | Gilead Connecticut, Inc. | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor |
| EP3552607A3 (en) | 2008-12-08 | 2020-01-15 | Gilead Connecticut, Inc. | Imidazopyrazine syk inhibitors |
| JP5567587B2 (ja) | 2008-12-08 | 2014-08-06 | ギリアード コネチカット， インコーポレイテッド | イミダゾピラジンＳｙｋ阻害剤 |
| KR101717809B1 (ko) | 2010-03-11 | 2017-03-17 | 질레드 코네티컷 인코포레이티드 | 이미다조피리딘 ｓｙｋ 억제제 |
| PL2861608T3 (pl) | 2012-06-19 | 2019-09-30 | Debiopharm International Sa | Pochodne prolekowe (e)-n-metylo-n-((3-metylobenzofuran-2-ylo)metylo)-3-(7-okso-5,6,7,8-tetrahydro-1,8-naftyrydyn-3-ylo)akryloamidu |
| PL3027171T3 (pl) | 2013-07-30 | 2020-08-24 | Gilead Connecticut, Inc. | Formulacja inhibitorów syk |
| CA2919661C (en) | 2013-07-30 | 2020-08-18 | Gilead Connecticut, Inc. | Polymorph of syk inhibitors |
| KR20160090903A (ko) | 2013-12-04 | 2016-08-01 | 길리애드 사이언시즈, 인코포레이티드 | 암을 치료하는 방법 |
| GB201321738D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic Agents |
| TWI735853B (zh) | 2013-12-23 | 2021-08-11 | 美商克洛諾斯生技有限公司 | 脾酪胺酸激酶抑制劑 |
| US9290505B2 (en) | 2013-12-23 | 2016-03-22 | Gilead Sciences, Inc. | Substituted imidazo[1,2-a]pyrazines as Syk inhibitors |
| JP6310144B2 (ja) | 2014-07-14 | 2018-04-18 | ギリアード サイエンシーズ， インコーポレイテッド | がんを処置するための組み合わせ |
| BR122023021456A2 (pt) | 2016-02-26 | 2024-02-20 | Debiopharm International S.A. | Uso de di-hidrogeno fosfato de {6- [(e)-3-{metil[(3-metil-1-benfofuran-2- iol)metil]amino)-3- oxopro-1-en-1-il]-2-oxo-3,4-di-hidro-1,8-naftiridin-1(2h)- il}metila para tratamento de osteomielite do pé diabético e composição farmacêutica |
| CN115028640A (zh) | 2017-08-25 | 2022-09-09 | 吉利德科学公司 | Syk抑制剂的多晶型物 |
| SMT202300138T1 (it) | 2019-02-14 | 2023-07-20 | Debiopharm Int Sa | Formulazione di afabicin, metodo per produrre la stessa |
| AU2020225455A1 (en) | 2019-02-22 | 2021-09-09 | Kronos Bio, Inc. | Solid forms of condensed pyrazines as Syk inhibitors |
| AU2020293635B2 (en) | 2019-06-14 | 2025-05-29 | Debiopharm International S.A. | Medicament and use thereof for treating bacterial infections involving biofilm |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507294A (en) * | 1982-03-08 | 1985-03-26 | Schering Corp. | Imidazo[1,2-a]pyrazines |
| EP0068378B1 (en) | 1981-06-26 | 1986-03-05 | Schering Corporation | Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them |
| US4725601A (en) | 1985-06-04 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers |
| PT97467A (pt) | 1990-04-27 | 1992-01-31 | Byk Gulden Lomberg Chem Fab | Processo para preparacao de novas piridazinas e de composicoes farmaceuticas que as contem |
| US5041442A (en) * | 1990-07-31 | 1991-08-20 | Syntex (U.S.A.) Inc. | Pyrrolo(1,2-a)pyrazines as inhibitors of gastric acid secretion |
| AU8712191A (en) * | 1990-10-15 | 1992-05-20 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New diazines |
| AU2870492A (en) * | 1991-10-25 | 1993-05-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pyrrolo-pyridazines with gastro-intestinal protective action |
| ES2185693T3 (es) * | 1994-01-19 | 2003-05-01 | Sankyo Co | Derivado de pirrolopiridacina. |
| SE9602286D0 (sv) | 1996-06-10 | 1996-06-10 | Astra Ab | New compounds |
| SE9700661D0 (sv) | 1997-02-25 | 1997-02-25 | Astra Ab | New compounds |
| SE9704404D0 (sv) | 1997-11-28 | 1997-11-28 | Astra Ab | New compounds |
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1997
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1998
- 1998-11-16 AR ARP980105799A patent/AR016972A1/es unknown
- 1998-11-16 TW TW087118942A patent/TW515798B/zh active
- 1998-11-16 ZA ZA9810468A patent/ZA9810468B/xx unknown
- 1998-11-17 MY MYPI98005216A patent/MY121032A/en unknown
- 1998-11-18 CZ CZ20001947A patent/CZ292349B6/cs not_active IP Right Cessation
- 1998-11-18 SK SK674-2000A patent/SK283904B6/sk unknown
- 1998-11-18 CN CNB98813344XA patent/CN1142933C/zh not_active Expired - Fee Related
- 1998-11-18 DE DE69811735T patent/DE69811735T2/de not_active Expired - Fee Related
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- 1998-11-18 CA CA002311798A patent/CA2311798A1/en not_active Abandoned
- 1998-11-18 NZ NZ504355A patent/NZ504355A/en unknown
- 1998-11-18 EP EP98957270A patent/EP1042324B1/en not_active Expired - Lifetime
- 1998-11-18 ID IDW20000987A patent/ID24730A/id unknown
- 1998-11-18 PL PL98340920A patent/PL340920A1/xx not_active Application Discontinuation
- 1998-11-18 HU HU0100601A patent/HUP0100601A3/hu unknown
- 1998-11-18 KR KR1020007005804A patent/KR20010032559A/ko not_active Ceased
- 1998-11-18 US US09/194,823 patent/US6518270B1/en not_active Expired - Lifetime
- 1998-11-18 UA UA2000052801A patent/UA70932C2/uk unknown
- 1998-11-18 AU AU13565/99A patent/AU752187C/en not_active Ceased
- 1998-11-18 DK DK98957270T patent/DK1042324T3/da active
- 1998-11-18 IL IL13614598A patent/IL136145A0/xx unknown
- 1998-11-18 JP JP2000523214A patent/JP2001525322A/ja active Pending
- 1998-11-18 ES ES98957270T patent/ES2191356T3/es not_active Expired - Lifetime
- 1998-11-18 AT AT98957270T patent/ATE233263T1/de not_active IP Right Cessation
- 1998-11-18 PT PT98957270T patent/PT1042324E/pt unknown
- 1998-11-18 WO PCT/SE1998/002091 patent/WO1999028322A1/en not_active Ceased
- 1998-11-18 RU RU2000113729/04A patent/RU2241000C2/ru not_active IP Right Cessation
- 1998-11-18 BR BR9814755-2A patent/BR9814755A/pt not_active Application Discontinuation
- 1998-11-18 TR TR2000/01530T patent/TR200001530T2/xx unknown
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2000
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