HRP20020853A2 - Alkylated imidazopyridine derivatives - Google Patents
Alkylated imidazopyridine derivatives Download PDFInfo
- Publication number
- HRP20020853A2 HRP20020853A2 HR20020853A HRP20020853A HRP20020853A2 HR P20020853 A2 HRP20020853 A2 HR P20020853A2 HR 20020853 A HR20020853 A HR 20020853A HR P20020853 A HRP20020853 A HR P20020853A HR P20020853 A2 HRP20020853 A2 HR P20020853A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- hydrogen
- alkoxy
- radical
- substituents
- Prior art date
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- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 135
- 230000002265 prevention Effects 0.000 claims abstract description 10
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims description 133
- 229910052739 hydrogen Inorganic materials 0.000 claims description 133
- -1 2-7C-alkenyl Chemical group 0.000 claims description 123
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 73
- 125000001424 substituent group Chemical group 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 239000001301 oxygen Substances 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 239000000460 chlorine Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 6
- 229910006069 SO3H Inorganic materials 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 230000004962 physiological condition Effects 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 9
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
- 150000002431 hydrogen Chemical group 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 150000003254 radicals Chemical class 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000003480 eluent Substances 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000006264 debenzylation reaction Methods 0.000 description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 238000002483 medication Methods 0.000 description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- IYVLJJWENFDKKI-LMMKCTJWSA-N (7r,8s,9r)-2,3,8-trimethyl-9-phenyl-9,10-dihydro-7h-imidazo[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@]2(O)C)C)C)=CC=CC=C1 IYVLJJWENFDKKI-LMMKCTJWSA-N 0.000 description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 3
- ULOIAOPTGWSNHU-UHFFFAOYSA-N 2-butyl radical Chemical compound C[CH]CC ULOIAOPTGWSNHU-UHFFFAOYSA-N 0.000 description 3
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 3
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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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- XFZLCTUONFKKGV-UHFFFAOYSA-N ethyl 2,3-dimethyl-8-phenylmethoxyimidazo[1,2-a]pyridine-6-carboxylate Chemical compound C12=NC(C)=C(C)N2C=C(C(=O)OCC)C=C1OCC1=CC=CC=C1 XFZLCTUONFKKGV-UHFFFAOYSA-N 0.000 description 3
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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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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00106696 | 2000-03-29 | ||
| PCT/EP2001/003507 WO2001072754A1 (en) | 2000-03-29 | 2001-03-28 | Alkylated imidazopyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020853A2 true HRP20020853A2 (en) | 2005-02-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020853A HRP20020853A2 (en) | 2000-03-29 | 2002-10-28 | Alkylated imidazopyridine derivatives |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6916825B2 (xx) |
| EP (1) | EP1313739B1 (xx) |
| JP (1) | JP2003528876A (xx) |
| KR (1) | KR100823762B1 (xx) |
| CN (1) | CN1213049C (xx) |
| AT (1) | ATE332302T1 (xx) |
| AU (1) | AU783764B2 (xx) |
| BR (1) | BR0109542A (xx) |
| CA (1) | CA2404460A1 (xx) |
| CZ (1) | CZ20023116A3 (xx) |
| DE (1) | DE60121345T2 (xx) |
| EA (1) | EA005215B1 (xx) |
| ES (1) | ES2267737T3 (xx) |
| HK (1) | HK1056173A1 (xx) |
| HR (1) | HRP20020853A2 (xx) |
| HU (1) | HUP0300578A3 (xx) |
| IL (1) | IL151201A0 (xx) |
| MX (1) | MXPA02009552A (xx) |
| NO (1) | NO20024597L (xx) |
| NZ (1) | NZ520835A (xx) |
| PL (1) | PL357811A1 (xx) |
| SK (1) | SK13872002A3 (xx) |
| WO (1) | WO2001072754A1 (xx) |
| ZA (1) | ZA200207636B (xx) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030100578A1 (en) * | 2000-03-29 | 2003-05-29 | Senn Jorg Bilfinger | Pyrano[2,3-c]imidazo[-1,2-a]pyridine derivatives for the treatment of gastrointestinal disorders |
| NZ520837A (en) | 2000-03-29 | 2005-01-28 | Altana Pharma Ag | Prodrugs of imidazopyridine derivatives |
| CA2426616A1 (en) | 2000-10-25 | 2002-05-02 | Altana Pharma Ag | Polysubstituted imidazopyridines as gastric secretion inhibitors |
| MXPA04001048A (es) * | 2001-08-03 | 2004-05-20 | Altana Pharma Ag | Imidazopiridinas sustituidas con alquilo, para el tratamiento de trastornos gastrointestinales. |
| DE10145457A1 (de) * | 2001-09-14 | 2003-04-03 | Basf Ag | Substituierte Imidazo[1,2-a]-5,6,7,8-tetrahydropyridin-8-one, Verfahren zu ihrer Herstellung, sowie deren Verwendung zur Herstellung von Imidazo[1,2,-a]pyridinen |
| KR20040081204A (ko) | 2002-02-15 | 2004-09-20 | 알타나 파마 아게 | 트리시클릭 ｎ-아실 화합물 |
| EP1565465A1 (en) | 2002-11-19 | 2005-08-24 | ALTANA Pharma AG | 8-substituted imidazopyridines |
| MXPA05006349A (es) * | 2002-12-20 | 2005-08-26 | Altana Pharma Ag | 8-trialquisiloxi -2-metil -9-fenil -7- oxo-7, 8, 9, 10- tetrahidroimidazo [1, 2h] [1, 7]. |
| BRPI0407541A (pt) * | 2003-02-17 | 2006-02-14 | Altana Pharma Ag | combinações e uso de compostos farmaceuticamente ativos selecionados |
| AR044129A1 (es) | 2003-05-06 | 2005-08-24 | Altana Pharma Ag | Compuestos intermedios de imidazopiridina. proceso de preparacion. |
| WO2005041961A1 (en) | 2003-11-03 | 2005-05-12 | 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 |
| US7215655B2 (en) * | 2004-01-09 | 2007-05-08 | Interdigital Technology Corporation | Transport format combination selection in a wireless transmit/receive unit |
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| US4468400A (en) * | 1982-12-20 | 1984-08-28 | Schering Corporation | Antiulcer tricyclic imidazo [1,2-a]pyridines |
| SE9401197D0 (sv) | 1994-04-11 | 1994-04-11 | Astra Ab | Active compounds |
| PL190803B1 (pl) * | 1997-03-24 | 2006-02-28 | Altana Pharma Ag | Związki tetrahydropirydylowe, środki farmaceutyczne zawierające te związki oraz zastosowanie tych związków |
| EP0984969B1 (en) * | 1997-05-28 | 2008-07-09 | Nycomed GmbH | Fused dihydropyrans |
| HUP0001555A3 (en) * | 1997-10-30 | 2001-01-29 | Altana Pharma Ag | Tetrahydro-imidazo-naphthyridine derivatives, pharmaceutical compositions thereof and process for their preparation |
| US20030100578A1 (en) * | 2000-03-29 | 2003-05-29 | Senn Jorg Bilfinger | Pyrano[2,3-c]imidazo[-1,2-a]pyridine derivatives for the treatment of gastrointestinal disorders |
| AU783724B2 (en) * | 2000-03-29 | 2005-12-01 | Altana Pharma Ag | Tricyclic imidazopyridines |
| NZ520837A (en) * | 2000-03-29 | 2005-01-28 | Altana Pharma Ag | Prodrugs of imidazopyridine derivatives |
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