CA2370231A1 - Haloalkoxy imidazonaphthyridines - Google Patents
Haloalkoxy imidazonaphthyridines Download PDFInfo
- Publication number
- CA2370231A1 CA2370231A1 CA002370231A CA2370231A CA2370231A1 CA 2370231 A1 CA2370231 A1 CA 2370231A1 CA 002370231 A CA002370231 A CA 002370231A CA 2370231 A CA2370231 A CA 2370231A CA 2370231 A1 CA2370231 A1 CA 2370231A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- alkoxy
- substituents
- alkyl
- substituted
- 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.)
- Abandoned
Links
- -1 Haloalkoxy imidazonaphthyridines Chemical class 0.000 title claims description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 3
- 230000002265 prevention Effects 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 102
- 229910052739 hydrogen Inorganic materials 0.000 claims description 102
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 61
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000004789 chlorodifluoromethoxy group Chemical class ClC(O*)(F)F 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 21
- 150000003254 radicals Chemical class 0.000 description 17
- 239000002904 solvent Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000002496 gastric effect Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
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- 210000002784 stomach Anatomy 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 108010079943 Pentagastrin Proteins 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
- 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 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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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- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 229960002626 clarithromycin Drugs 0.000 description 2
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 210000004211 gastric acid Anatomy 0.000 description 2
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- 150000004677 hydrates Chemical class 0.000 description 2
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- 230000005764 inhibitory process Effects 0.000 description 2
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- 238000001990 intravenous administration Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229960000282 metronidazole Drugs 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
- FHHGNULEXOWEKU-DJIMGWMZSA-N (7r,8r,9r)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine-7,8-diol Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3[C@@H](O)[C@@H]2O)C)C)=CC=CC=C1 FHHGNULEXOWEKU-DJIMGWMZSA-N 0.000 description 1
- HTPLUZLALDWDJK-KBAYOESNSA-N (7r,8r,9r)-2,3-dimethyl-9-phenyl-7-(2,2,2-trifluoroethoxy)-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3[C@@H](OCC(F)(F)F)[C@@H]2O)C)C)=CC=CC=C1 HTPLUZLALDWDJK-KBAYOESNSA-N 0.000 description 1
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- ZZXQWFQBPSUCAF-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-b][1,8]naphthyridine Chemical class N1C2=NC=CC=C2C=C2C1NCN2 ZZXQWFQBPSUCAF-UHFFFAOYSA-N 0.000 description 1
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- 235000012208 gluconic acid Nutrition 0.000 description 1
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- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 description 1
- 229960002182 imipenem Drugs 0.000 description 1
- GSOSVVULSKVSLQ-JJVRHELESA-N imipenem hydrate Chemical compound O.C1C(SCCNC=N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 GSOSVVULSKVSLQ-JJVRHELESA-N 0.000 description 1
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- YPBATNHYBCGSSN-VWPFQQQWSA-N mezlocillin Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC=CC=1)C(=O)N1CCN(S(C)(=O)=O)C1=O YPBATNHYBCGSSN-VWPFQQQWSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
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- 230000020477 pH reduction Effects 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
- 229960005019 pantoprazole Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 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
- 229960004633 pirenzepine Drugs 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 229960000620 ranitidine Drugs 0.000 description 1
- 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
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000018556 stomach disease Diseases 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
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- 229950004351 telenzepine Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Luminescent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99107688.6 | 1999-04-17 | ||
| EP99107688 | 1999-04-17 | ||
| PCT/EP2000/003388 WO2000063211A1 (en) | 1999-04-17 | 2000-04-14 | Haloalkoxy imidazonaphthyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2370231A1 true CA2370231A1 (en) | 2000-10-26 |
Family
ID=8237986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002370231A Abandoned CA2370231A1 (en) | 1999-04-17 | 2000-04-14 | Haloalkoxy imidazonaphthyridines |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6503923B1 (enExample) |
| EP (1) | EP1173439B1 (enExample) |
| JP (1) | JP2002542248A (enExample) |
| AT (1) | ATE240956T1 (enExample) |
| AU (1) | AU3966600A (enExample) |
| CA (1) | CA2370231A1 (enExample) |
| DE (1) | DE60002855T2 (enExample) |
| DK (1) | DK1173439T3 (enExample) |
| ES (1) | ES2199810T3 (enExample) |
| PT (1) | PT1173439E (enExample) |
| SI (1) | SI1173439T1 (enExample) |
| WO (1) | WO2000063211A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002034749A1 (en) | 2000-10-25 | 2002-05-02 | 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 |
| WO2002069968A1 (en) * | 2001-03-08 | 2002-09-12 | Astrazeneca Ab | New use |
| HUP0400379A3 (en) | 2001-08-02 | 2007-10-29 | Altana Pharma Ag | Tricyclic epoxides and their use for the preparation of pharmaceutically active agents |
| US20040235882A1 (en) * | 2001-08-03 | 2004-11-25 | Jorg Senn-Bilfinger | Amino-substituted imidazopyridines for the treatment of gastrointestial diseases |
| WO2003016310A1 (en) * | 2001-08-03 | 2003-02-27 | Altana Pharma Ag | Alkyl-substituted imidazopyridines for the treatment of gastrointestinal disorders |
| EA008375B1 (ru) | 2002-02-15 | 2007-04-27 | Алтана Фарма Аг | Трициклические n-ацильные соединения |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| CN100384842C (zh) | 2002-11-19 | 2008-04-30 | 奥坦纳医药公司 | 8-取代的咪唑并吡啶类化合物 |
| CN1747731A (zh) * | 2003-02-17 | 2006-03-15 | 艾塔那法玛公司 | 含有咪唑并吡啶的组合和其在治疗胃肠炎性病症中的用途 |
| RS52908B (sr) | 2003-03-10 | 2014-02-28 | Takeda Gmbh | Novi postupak za dobijanje roflumilasta |
| AU2004243444A1 (en) * | 2003-05-27 | 2004-12-09 | Altana Pharma Ag | Pharmaceutical combinations of a proton pump inhibitor and a compound which modifies gastrointestinal motility |
| CA2544325A1 (en) | 2003-11-03 | 2005-05-12 | Astrazeneca Ab | Imidazo [1,2-a] pyridine derivatives for the treatment of silent gastro-esophageal reflux |
| AR046893A1 (es) * | 2003-12-16 | 2005-12-28 | Altana Pharma Ag | Bencimidazoles triciclicos |
| 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. |
| US7931659B2 (en) * | 2004-09-10 | 2011-04-26 | Penumbra, Inc. | System and method for treating ischemic stroke |
| CA2582256A1 (en) * | 2004-10-01 | 2006-04-13 | Altana Pharma Ag | Substituted tricyclic benzimidazoles |
| CA2601250C (en) * | 2005-03-16 | 2014-10-28 | Nycomed Gmbh | Taste masked dosage form containing roflumilast |
Family Cites Families (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 |
| IL108520A (en) | 1993-02-15 | 1997-09-30 | Byk Gulden Lomberg Chem Fab | 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| HUP0001555A3 (en) | 1997-10-30 | 2001-01-29 | Altana Pharma Ag | Tetrahydro-imidazo-naphthyridine derivatives, pharmaceutical compositions thereof and process for their preparation |
| HUP0102990A3 (en) | 1998-09-23 | 2002-09-30 | Altana Pharma Ag | Tetrahydroimidazo-naphtyridine derivatives and pharmaceutical compositions thereof |
-
2000
- 2000-04-14 US US09/926,267 patent/US6503923B1/en not_active Expired - Fee Related
- 2000-04-14 AU AU39666/00A patent/AU3966600A/en not_active Abandoned
- 2000-04-14 DK DK00918882T patent/DK1173439T3/da active
- 2000-04-14 JP JP2000612301A patent/JP2002542248A/ja not_active Withdrawn
- 2000-04-14 ES ES00918882T patent/ES2199810T3/es not_active Expired - Lifetime
- 2000-04-14 SI SI200030157T patent/SI1173439T1/xx unknown
- 2000-04-14 AT AT00918882T patent/ATE240956T1/de not_active IP Right Cessation
- 2000-04-14 PT PT00918882T patent/PT1173439E/pt unknown
- 2000-04-14 DE DE60002855T patent/DE60002855T2/de not_active Expired - Fee Related
- 2000-04-14 EP EP00918882A patent/EP1173439B1/en not_active Expired - Lifetime
- 2000-04-14 CA CA002370231A patent/CA2370231A1/en not_active Abandoned
- 2000-04-14 WO PCT/EP2000/003388 patent/WO2000063211A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| PT1173439E (pt) | 2003-10-31 |
| JP2002542248A (ja) | 2002-12-10 |
| ES2199810T3 (es) | 2004-03-01 |
| AU3966600A (en) | 2000-11-02 |
| EP1173439A1 (en) | 2002-01-23 |
| SI1173439T1 (en) | 2003-10-31 |
| DK1173439T3 (da) | 2003-09-08 |
| US6503923B1 (en) | 2003-01-07 |
| DE60002855D1 (de) | 2003-06-26 |
| EP1173439B1 (en) | 2003-05-21 |
| DE60002855T2 (de) | 2004-05-06 |
| WO2000063211A1 (en) | 2000-10-26 |
| ATE240956T1 (de) | 2003-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |