EA005377B1 - ТЕТРАГИДРОИМИДАЗО [1,2-h][1,7] НАФТИРИДИНОВЫЕ СОЕДИНЕНИЯ - Google Patents
ТЕТРАГИДРОИМИДАЗО [1,2-h][1,7] НАФТИРИДИНОВЫЕ СОЕДИНЕНИЯ Download PDFInfo
- Publication number
- EA005377B1 EA005377B1 EA200100315A EA200100315A EA005377B1 EA 005377 B1 EA005377 B1 EA 005377B1 EA 200100315 A EA200100315 A EA 200100315A EA 200100315 A EA200100315 A EA 200100315A EA 005377 B1 EA005377 B1 EA 005377B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- hydroxy
- tetrahydroimidazo
- dimethyl
- naphthyridine
- phenyl
- Prior art date
Links
- PIKFXKSSNMLKLP-UHFFFAOYSA-N 1,2,3,5-tetrahydroimidazo[1,2-h][1,7]naphthyridine Chemical class C1C=C2C=CC=NC2=C2N1CCN2 PIKFXKSSNMLKLP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 230000002265 prevention Effects 0.000 claims abstract description 6
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 3
- -1 hydroxy, methoxy, ethoxy, isopropoxy, methoxyethoxy Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- 239000013543 active substance Substances 0.000 description 7
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- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
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- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 3
- 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
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- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
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- BZGIPVGCJGXQTA-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] n,n-diphenylcarbamothioate Chemical compound C=1C=CC=CC=1N(C(=O)SCCN(CC)CC)C1=CC=CC=C1 BZGIPVGCJGXQTA-UHFFFAOYSA-N 0.000 description 2
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- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
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- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98117988 | 1998-09-23 | ||
| DE19843504 | 1998-09-23 | ||
| PCT/EP1999/006899 WO2000017200A1 (en) | 1998-09-23 | 1999-09-17 | Tetrahydropyridoethers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200100315A1 EA200100315A1 (ru) | 2001-10-22 |
| EA005377B1 true EA005377B1 (ru) | 2005-02-24 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200100315A EA005377B1 (ru) | 1998-09-23 | 1999-09-17 | ТЕТРАГИДРОИМИДАЗО [1,2-h][1,7] НАФТИРИДИНОВЫЕ СОЕДИНЕНИЯ |
Country Status (31)
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|---|---|
| US (4) | US6436953B1 (enExample) |
| EP (1) | EP1115725B1 (enExample) |
| JP (1) | JP4145492B2 (enExample) |
| KR (1) | KR100668400B1 (enExample) |
| CN (2) | CN1155598C (enExample) |
| AT (1) | ATE231862T1 (enExample) |
| AU (1) | AU763463B2 (enExample) |
| BG (1) | BG65195B1 (enExample) |
| BR (1) | BR9914044A (enExample) |
| CA (1) | CA2344251A1 (enExample) |
| CZ (1) | CZ292335B6 (enExample) |
| DE (1) | DE69905178T2 (enExample) |
| DK (1) | DK1115725T3 (enExample) |
| EA (1) | EA005377B1 (enExample) |
| EE (1) | EE04677B1 (enExample) |
| ES (1) | ES2191464T3 (enExample) |
| GE (1) | GEP20032926B (enExample) |
| HK (1) | HK1038360B (enExample) |
| HR (1) | HRP20010224A2 (enExample) |
| HU (1) | HUP0102990A3 (enExample) |
| ID (1) | ID28896A (enExample) |
| IL (2) | IL142063A0 (enExample) |
| NO (1) | NO317304B1 (enExample) |
| NZ (1) | NZ510610A (enExample) |
| PL (1) | PL193616B1 (enExample) |
| PT (1) | PT1115725E (enExample) |
| RS (1) | RS50145B (enExample) |
| SI (1) | SI1115725T1 (enExample) |
| SK (1) | SK285165B6 (enExample) |
| TR (1) | TR200100805T2 (enExample) |
| WO (1) | WO2000017200A1 (enExample) |
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| WO2000017200A1 (en) | 1998-09-23 | 2000-03-30 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyridoethers |
| AU3966600A (en) * | 1999-04-17 | 2000-11-02 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Haloalkoxy imidazonaphthyridines |
| CA2721484A1 (en) * | 1999-05-12 | 2000-11-12 | President And Fellows Of Harvard College | Dopamine transporter imaging agents |
| WO2001072757A1 (en) * | 2000-03-29 | 2001-10-04 | Altana Pharma Ag | Tricyclic imidazopyridines |
| JP2003528878A (ja) * | 2000-03-29 | 2003-09-30 | アルタナ ファルマ アクチエンゲゼルシャフト | イミダゾピリジン誘導体のプロドラッグ |
| AU2002210563B2 (en) * | 2000-10-25 | 2007-03-01 | Altana Pharma Ag | Polysubstituted imidazopyridines as gastric secretion inhibitors |
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| CZ20032398A3 (cs) * | 2001-03-08 | 2004-02-18 | Astrazeneca Ab | Nové použití derivátů 6-karboxamidoimidazo [1,2-a] pyridinu |
| ATE336493T1 (de) | 2001-08-02 | 2006-09-15 | Altana Pharma Ag | Tricyclische epoxide |
| CN1656096A (zh) * | 2001-08-03 | 2005-08-17 | 奥坦纳医药公司 | 用于治疗胃肠病症的烷基－取代的咪唑吡啶 |
| US20040235882A1 (en) * | 2001-08-03 | 2004-11-25 | Jorg Senn-Bilfinger | Amino-substituted imidazopyridines for the treatment of gastrointestial diseases |
| HRP20040834A2 (en) | 2002-02-15 | 2005-06-30 | Altana Pharma Ag | Tricyclic n-acyl compounds |
| MY140561A (en) * | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| WO2003094967A2 (en) * | 2002-05-07 | 2003-11-20 | Altana Pharma Ag | New combination of reversible proton pump inhibitors and airway therapeutics for treating airway disorders |
| HRP20050528A2 (en) | 2002-11-19 | 2006-06-30 | Altana Pharma Ag | 8-substituted imidazopyridines |
| ES2312844T3 (es) | 2002-12-12 | 2009-03-01 | Nycomed Gmbh | Medicamento de combinacion de r, r-formoterol y ciclesonida. |
| PL375933A1 (en) * | 2002-12-20 | 2005-12-12 | Altana Pharma Ag | 8-trialkylsiloxy-2-methyl-9-phenyl-7-oxo-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridines |
| BRPI0407541A (pt) * | 2003-02-17 | 2006-02-14 | Altana Pharma Ag | combinações e uso de compostos farmaceuticamente ativos selecionados |
| EA009985B1 (ru) | 2003-03-10 | 2008-04-28 | Никомед Гмбх | Новый способ получения рофлумиласта |
| TW200503783A (en) * | 2003-04-11 | 2005-02-01 | Altana Pharma Ag | Oral pharmaceutical preparation for proton pump antagonists |
| SA04250092B1 (ar) * | 2003-05-14 | 2008-05-04 | التانا فاروا ايه جي | مركب وسيط جديد لتحضير مركبات إيميدازوبيريدين imidazopyridines فعالة علاجياً |
| CA2526566A1 (en) * | 2003-05-27 | 2004-12-09 | Altana Pharma Ag | Pharmaceutical combinations of a proton pump inhibitor and a compound which modifies gastrointestinal motility |
| CA2537182A1 (en) * | 2003-08-29 | 2005-03-10 | Dynogen Pharmaceuticals, Inc. | Compositions useful for treating gastrointestinal motility disorders |
| WO2005025578A1 (en) | 2003-09-16 | 2005-03-24 | Altana Pharma Ag | Use of ciclesonide for the treatment of respiratory diseases |
| EP1682133A1 (en) * | 2003-11-03 | 2006-07-26 | AstraZeneca AB | Imidazo 1,2-a pyridine derivatives for the treatment of silent gastro-esophageal reflux |
| WO2005058894A1 (en) | 2003-12-19 | 2005-06-30 | Altana Pharma Ag | Intermediates for the preparation of tricyclic dihydropyrano -imidazo -pyridines derivatives |
| AR047605A1 (es) * | 2004-02-17 | 2006-01-25 | Altana Pharma Ag | Imidazopiridinas triciclicas e intermediarios en la sintesis de las mismas,sus procesos de preparacion,composiciones farmaceuticas que los contienen y usos. |
| DK1784404T3 (da) | 2004-09-03 | 2012-02-13 | Yuhan Corp | Pyrrolo[2,3-c]pyridinderivater samt fremgangsmåder til deres fremstilling |
| DK1784402T3 (da) | 2004-09-03 | 2011-11-14 | Yuhan Corp | Pyrrolo[3,2-c]pyridinderivater samt fremgangsmåder til deres fremstilling |
| ES2426920T3 (es) | 2004-09-03 | 2013-10-25 | Yuhan Corporation | Derivados de pirrolo[3,2-B]piridina y procesos para su preparación |
| ES2421916T3 (es) * | 2005-03-16 | 2013-09-06 | Nycomed Gmbh | Forma farmacéutica de sabor enmascarado que contiene roflumilast |
| EP2080513A1 (en) | 2008-01-16 | 2009-07-22 | Schraermeyer, Ulrich, Prof. Dr. rer. nat | Tetrahydropyridoethers for treatment of AMD |
| EP2452680B1 (en) | 2009-07-09 | 2019-12-18 | RaQualia Pharma Inc. | Acid pump antagonist for the treatment of diseases involved in abnormal gastrointestinal motility |
| WO2012027240A1 (en) * | 2010-08-23 | 2012-03-01 | Schering Corporation | Fused tricyclic inhibitors of mammalian target of rapamycin |
| BR112014031396B1 (pt) * | 2012-06-15 | 2019-11-26 | Bio Pharm Solutions Co Ltd | composto de sulfamato de fenilalquila e composição de relaxante muscular compreendendo o mesmo |
| US20160235724A1 (en) | 2013-10-08 | 2016-08-18 | Katairo Gmbh | Tetrahydropyridoethers for the treatment of stargardt's disease |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4468400A (en) * | 1982-12-20 | 1984-08-28 | Schering Corporation | Antiulcer tricyclic imidazo [1,2-a]pyridines |
| EP0299470A1 (de) * | 1987-07-16 | 1989-01-18 | Byk Gulden Lomberg Chemische Fabrik GmbH | Imidazo[1,2-a]pyridine |
| WO1995027714A1 (en) * | 1994-04-11 | 1995-10-19 | Astra Aktiebolag | Active compounds |
| WO1998042707A1 (en) * | 1997-03-24 | 1998-10-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyrido compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10505332A (ja) * | 1994-07-28 | 1998-05-26 | ビイク グルデン ロンベルク ヒェーミッシェ ファブリーク ゲゼルシャフト ミット ベシュレンクテル ハフツング | アシルイミダゾピリジン |
| BR9807883A (pt) * | 1997-03-24 | 2000-02-22 | Byk Gulden Lomberg Chem Fab | Compostos de tetraidropirido |
| WO2000017200A1 (en) | 1998-09-23 | 2000-03-30 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyridoethers |
-
1999
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4468400A (en) * | 1982-12-20 | 1984-08-28 | Schering Corporation | Antiulcer tricyclic imidazo [1,2-a]pyridines |
| EP0299470A1 (de) * | 1987-07-16 | 1989-01-18 | Byk Gulden Lomberg Chemische Fabrik GmbH | Imidazo[1,2-a]pyridine |
| WO1995027714A1 (en) * | 1994-04-11 | 1995-10-19 | Astra Aktiebolag | Active compounds |
| WO1998042707A1 (en) * | 1997-03-24 | 1998-10-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyrido compounds |
Non-Patent Citations (1)
| Title |
|---|
| J.J. KAMINSKI ET AL.: JOURNAL OF MEDICINAL CHEMISTRY, vol. 28, no. 7, 1985, pages 876-92, XP002094814, cited in the application, table IV * |
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