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)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843504 | 1998-09-23 | ||
| EP98117988 | 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 |
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|---|---|
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| EP (1) | EP1115725B1 (enExample) |
| JP (1) | JP4145492B2 (enExample) |
| KR (1) | KR100668400B1 (enExample) |
| CN (2) | CN100506821C (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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| US6436953B1 (en) * | 1998-09-23 | 2002-08-20 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyridoethers |
| AU3966600A (en) | 1999-04-17 | 2000-11-02 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Haloalkoxy imidazonaphthyridines |
| CA2285516C (en) * | 1999-05-12 | 2010-12-07 | President And Fellows Of Harvard College | Dopamine transporter imaging agents |
| PL365165A1 (en) * | 2000-03-29 | 2004-12-27 | Altana Pharma Ag | Tricyclic imidazopyridines |
| CZ20023194A3 (cs) * | 2000-03-29 | 2003-01-15 | Altana Pharma Ag | Prekursory imidazopyridinových derivátů |
| AU1056302A (en) * | 2000-10-25 | 2002-05-06 | Byk Gulden Lomberg Chem Fab | 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 |
| US20040082605A1 (en) * | 2001-03-08 | 2004-04-29 | Arne Eek | Use |
| CA2452802A1 (en) | 2001-08-02 | 2003-02-20 | Altana Pharma Ag | Tricyclic epoxides |
| MXPA04001048A (es) * | 2001-08-03 | 2004-05-20 | Altana Pharma Ag | Imidazopiridinas sustituidas con alquilo, para el tratamiento de trastornos gastrointestinales. |
| WO2003014120A1 (en) * | 2001-08-03 | 2003-02-20 | Altana Pharma Ag | Amino-substituted imidazopyridines for the treatment of gastrointestinal diseases |
| JP2005519933A (ja) | 2002-02-15 | 2005-07-07 | アルタナ ファルマ アクチエンゲゼルシャフト | 三環式ｎ−アシル化合物 |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| HRP20041160A2 (en) * | 2002-05-07 | 2005-08-31 | Altana Pharma Ag | Novel combination for the treatment of airway disorders |
| EA008304B1 (ru) | 2002-11-19 | 2007-04-27 | Алтана Фарма Аг | 8-замещённые имидазопиридины |
| WO2004052374A1 (en) | 2002-12-12 | 2004-06-24 | Altana Pharma Ag | Combination medicament |
| EA010107B1 (ru) * | 2002-12-20 | 2008-06-30 | Алтана Фарма Аг | Силиловые простые эфиры |
| RS20050603A (sr) * | 2003-02-17 | 2007-09-21 | Altana Pharma Ag., | NOVE KOMBINACIJE I NOVA PRIMENA FARMACEUTSKIH AKTIVNIH JEDINjENjA |
| ES2335498T3 (es) | 2003-03-10 | 2010-03-29 | Nycomed Gmbh | Nuevo proceso para la preparacion de reflumilast. |
| 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 |
| MXPA05012463A (es) * | 2003-05-27 | 2006-01-30 | Altana Pharma Ag | Combinaciones farmaceuticas de un inhibidor de bomba protonica y un compuesto que modifica la motilidad gastrointestinal. |
| JP2007507425A (ja) * | 2003-08-29 | 2007-03-29 | ダイノゲン ファーマシューティカルズ，インコーポレイテッド | 胃腸管運動障害を処置するために有用な組成物 |
| PL1670482T5 (pl) | 2003-09-16 | 2022-10-03 | Covis Pharma Gmbh | Zastosowanie cyklezonidu w leczeniu chorób układu oddechowego |
| CA2544325A1 (en) * | 2003-11-03 | 2005-05-12 | Astrazeneca Ab | Imidazo [1,2-a] pyridine derivatives for the treatment of silent gastro-esophageal reflux |
| EP1697358A1 (en) | 2003-12-19 | 2006-09-06 | 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. |
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| US4468400A (en) * | 1982-12-20 | 1984-08-28 | Schering Corporation | Antiulcer tricyclic imidazo [1,2-a]pyridines |
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