CN100506821C - 四氢吡啶醚化合物 - Google Patents
四氢吡啶醚化合物 Download PDFInfo
- Publication number
- CN100506821C CN100506821C CNB2004100384351A CN200410038435A CN100506821C CN 100506821 C CN100506821 C CN 100506821C CN B2004100384351 A CNB2004100384351 A CN B2004100384351A CN 200410038435 A CN200410038435 A CN 200410038435A CN 100506821 C CN100506821 C CN 100506821C
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- Prior art keywords
- sub
- imidazo
- dimethyl
- phenyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 tetrahydropyridine ether compound Chemical class 0.000 title description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 3
- 230000002265 prevention Effects 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000003814 drug Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- PFUDJBXGGYVENA-BHIYHBOVSA-N (7r,8r,9r)-7,8-dimethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine Chemical compound C1([C@@H]2[C@H]([C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)OC)=CC=CC=C1 PFUDJBXGGYVENA-BHIYHBOVSA-N 0.000 claims 1
- RJASEHFHFJEXPR-BHIYHBOVSA-N (7r,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-BHIYHBOVSA-N 0.000 claims 1
- GDQBYAHOQAFREY-KBAYOESNSA-N (7r,8r,9r)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-KBAYOESNSA-N 0.000 claims 1
- PWILYDZRJORZDR-YSIASYRMSA-N (7r,8s,9s)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-YSIASYRMSA-N 0.000 claims 1
- GDQBYAHOQAFREY-RYQLBKOJSA-N (7r,8s,9s)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-RYQLBKOJSA-N 0.000 claims 1
- LHJMQBVQSCNUMD-RLLQIKCJSA-N (7s,8r,9r)-2,3-dimethyl-9-phenyl-7-propan-2-yloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC(C)C)=CC=CC=C1 LHJMQBVQSCNUMD-RLLQIKCJSA-N 0.000 claims 1
- PWILYDZRJORZDR-RLLQIKCJSA-N (7s,8r,9r)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-RLLQIKCJSA-N 0.000 claims 1
- RJASEHFHFJEXPR-QRQLOZEOSA-N (7s,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-QRQLOZEOSA-N 0.000 claims 1
- GDQBYAHOQAFREY-NXHRZFHOSA-N (7s,8r,9r)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-NXHRZFHOSA-N 0.000 claims 1
- PWILYDZRJORZDR-IHPCNDPISA-N (7s,8s,9s)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-IHPCNDPISA-N 0.000 claims 1
- GDQBYAHOQAFREY-SZMVWBNQSA-N (7s,8s,9s)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-SZMVWBNQSA-N 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 description 38
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- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical class C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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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- LKQXJYDAALZCAF-UHFFFAOYSA-N imidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CN2C=CN=C12 LKQXJYDAALZCAF-UHFFFAOYSA-N 0.000 description 1
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- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
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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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- 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 1
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- 239000000932 sedative agent Substances 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843504 | 1998-09-23 | ||
| EP98117988 | 1998-09-23 | ||
| DE19843504.5 | 1998-09-23 | ||
| EP98117988.0 | 1998-09-23 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998112992A Division CN1155598C (zh) | 1998-09-23 | 1999-09-17 | 四氢吡啶醚化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1560055A CN1560055A (zh) | 2005-01-05 |
| CN100506821C true CN100506821C (zh) | 2009-07-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100384351A Expired - Fee Related CN100506821C (zh) | 1998-09-23 | 1999-09-17 | 四氢吡啶醚化合物 |
| CNB998112992A Expired - Fee Related CN1155598C (zh) | 1998-09-23 | 1999-09-17 | 四氢吡啶醚化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998112992A Expired - Fee Related CN1155598C (zh) | 1998-09-23 | 1999-09-17 | 四氢吡啶醚化合物 |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US6436953B1 (https=) |
| EP (1) | EP1115725B1 (https=) |
| JP (1) | JP4145492B2 (https=) |
| KR (1) | KR100668400B1 (https=) |
| CN (2) | CN100506821C (https=) |
| AT (1) | ATE231862T1 (https=) |
| AU (1) | AU763463B2 (https=) |
| BG (1) | BG65195B1 (https=) |
| BR (1) | BR9914044A (https=) |
| CA (1) | CA2344251A1 (https=) |
| CZ (1) | CZ292335B6 (https=) |
| DE (1) | DE69905178T2 (https=) |
| DK (1) | DK1115725T3 (https=) |
| EA (1) | EA005377B1 (https=) |
| EE (1) | EE04677B1 (https=) |
| ES (1) | ES2191464T3 (https=) |
| GE (1) | GEP20032926B (https=) |
| HK (1) | HK1038360B (https=) |
| HR (1) | HRP20010224A2 (https=) |
| HU (1) | HUP0102990A3 (https=) |
| ID (1) | ID28896A (https=) |
| IL (2) | IL142063A0 (https=) |
| NO (1) | NO317304B1 (https=) |
| NZ (1) | NZ510610A (https=) |
| PL (1) | PL193616B1 (https=) |
| PT (1) | PT1115725E (https=) |
| RS (1) | RS50145B (https=) |
| SI (1) | SI1115725T1 (https=) |
| SK (1) | SK285165B6 (https=) |
| TR (1) | TR200100805T2 (https=) |
| WO (1) | WO2000017200A1 (https=) |
Families Citing this family (36)
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| EE04677B1 (et) | 1998-09-23 | 2006-08-15 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahdropridoeetrid, nende kasutamine ja ravim |
| JP2002542248A (ja) * | 1999-04-17 | 2002-12-10 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | ハロアルコキシイミダゾナフチリジン |
| CA2721484A1 (en) * | 1999-05-12 | 2000-11-12 | President And Fellows Of Harvard College | Dopamine transporter imaging agents |
| MXPA02009549A (es) * | 2000-03-29 | 2004-05-14 | Altana Pharma Ag | Imidazopiridinas triciclicas. |
| KR100860627B1 (ko) * | 2000-03-29 | 2008-09-29 | 니코메드 게엠베하 | 이미다조피리딘 유도체의 프로드러그 |
| PL360412A1 (en) * | 2000-10-25 | 2004-09-06 | 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 |
| EP1370261A2 (en) * | 2001-03-08 | 2003-12-17 | AstraZeneca AB | New use |
| US6927292B2 (en) | 2001-08-02 | 2005-08-09 | Altana Pharma Ag | Tricyclic epoxides |
| NZ531433A (en) * | 2001-08-03 | 2005-09-30 | Altana Pharma Ag | Alkyl-substituted imidazopyridines for the treatment of gastrointestinal disorders |
| WO2003014120A1 (en) * | 2001-08-03 | 2003-02-20 | Altana Pharma Ag | Amino-substituted imidazopyridines for the treatment of gastrointestinal 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 |
| EP1506016A2 (en) * | 2002-05-07 | 2005-02-16 | ALTANA Pharma AG | New combination of reversible proton pump inhibitors and airway therapeutics for treating airway disorders |
| CA2506027A1 (en) | 2002-11-19 | 2004-06-03 | Altana Pharma Ag | 8-substituted imidazopyridines |
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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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| NZ290819A (en) * | 1994-07-28 | 1998-06-26 | Byk Gulden Lomberg Chem Fab | Acyl 8-benzyloxy- or 8-benzylaminoimidazopyridines |
| AU740578B2 (en) * | 1997-03-24 | 2001-11-08 | Altana Pharma Ag | Tetrahydropyrido compounds |
| EP0971922B1 (en) * | 1997-03-24 | 2004-04-28 | ALTANA Pharma AG | Tetrahydropyrido compounds |
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