PH26967A - 5-substituted (4,5-c) imidazopyridine compounds which have useful platelet activating factor antagonistic activity - Google Patents
5-substituted (4,5-c) imidazopyridine compounds which have useful platelet activating factor antagonistic activity Download PDFInfo
- Publication number
- PH26967A PH26967A PH38328A PH38328A PH26967A PH 26967 A PH26967 A PH 26967A PH 38328 A PH38328 A PH 38328A PH 38328 A PH38328 A PH 38328A PH 26967 A PH26967 A PH 26967A
- Authority
- PH
- Philippines
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- compound according
- phenyl
- Prior art date
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- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 title claims abstract description 30
- 108010003541 Platelet Activating Factor Proteins 0.000 title claims abstract description 30
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title abstract 3
- 230000003042 antagnostic effect Effects 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 103
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 98
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 37
- 150000002367 halogens Chemical class 0.000 claims abstract description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 208000035475 disorder Diseases 0.000 claims abstract description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 112
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 25
- -1 1lworo Chemical group 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000005518 carboxamido group Chemical group 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- UOJMTSCORVQOHS-UHFFFAOYSA-N pachypodol Natural products COc1cc(ccc1O)C2=C(C)C(=O)c3c(O)cc(C)cc3O2 UOJMTSCORVQOHS-UHFFFAOYSA-N 0.000 claims description 2
- KUXZGRCCXVZOJT-UHFFFAOYSA-N imidazo[4,5-c]pyridine Chemical compound C1=N[CH]C2=NC=NC2=C1 KUXZGRCCXVZOJT-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 241000761389 Copa Species 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 241000219977 Vigna Species 0.000 claims 1
- 235000010726 Vigna sinensis Nutrition 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 235000012907 honey Nutrition 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 5
- 125000005358 mercaptoalkyl group Chemical group 0.000 abstract description 3
- 125000004001 thioalkyl group Chemical group 0.000 abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000003556 assay Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 235000002639 sodium chloride Nutrition 0.000 description 13
- 230000027455 binding Effects 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 11
- 239000000872 buffer Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 230000037396 body weight Effects 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 238000011534 incubation Methods 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- 231100000673 dose–response relationship Toxicity 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
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- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 4
- 229960003386 triazolam Drugs 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/167,671 US4914108A (en) | 1988-03-14 | 1988-03-14 | 5-substituted(4,5-c)imidazopyridine compounds which have useful platelet activating factor antagonistic activity |
| US07/317,871 US5019581A (en) | 1988-03-14 | 1989-03-06 | 5-substituted (4,5-c) imidazopyridine compounds which have useful platelet activating factor antagonistic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26967A true PH26967A (en) | 1992-12-28 |
Family
ID=26863369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH38328A PH26967A (en) | 1988-03-14 | 1989-03-14 | 5-substituted (4,5-c) imidazopyridine compounds which have useful platelet activating factor antagonistic activity |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5019581A (sv) |
| EP (1) | EP0344414B1 (sv) |
| JP (1) | JP2714426B2 (sv) |
| KR (1) | KR890014537A (sv) |
| AT (1) | ATE112774T1 (sv) |
| AU (1) | AU625058B2 (sv) |
| CA (1) | CA1337072C (sv) |
| DE (1) | DE68918755T2 (sv) |
| DK (1) | DK169872B1 (sv) |
| ES (1) | ES2061753T3 (sv) |
| FI (1) | FI91407C (sv) |
| IL (1) | IL89588A0 (sv) |
| NO (1) | NO169965C (sv) |
| NZ (1) | NZ228336A (sv) |
| PH (1) | PH26967A (sv) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5302601A (en) * | 1988-03-14 | 1994-04-12 | G. D. Searle & Co. | 5-substituted imidazo[4,5-c]pyridines |
| US5227384A (en) * | 1988-03-14 | 1993-07-13 | G. D. Searle & Co. | 5-substituted [4,5-c] imidazopyridines and pharmaceutical use thereof |
| US4990518A (en) * | 1989-09-13 | 1991-02-05 | G. D. Searle & Co. | Pharmacologically active heteroaryl substituted imidazo (4,5-c) pyridines |
| GB9116056D0 (en) * | 1991-07-24 | 1991-09-11 | British Bio Technology | Compounds |
| US5223539A (en) * | 1991-11-22 | 1993-06-29 | G. D. Searle & Co. | N,n-di-alkyl(phenoxy)benzamide derivatives |
| US5208242A (en) * | 1992-08-26 | 1993-05-04 | G. D. Searle & Co. | 5-substituted-4-phenyl-5H-imidazo[4,5-c]pyridine derivatives |
| US5262426A (en) * | 1993-01-22 | 1993-11-16 | G. D. Searle & Co. | N,N'-cycloalkyl/alkyl carboxamide 4H-imidazo-[4,5-b]pyridine compounds as PAF antagonists |
| US5360907A (en) * | 1993-06-14 | 1994-11-01 | G.D. Searle & Co. | Pyrrolo[3,2-B]pyridinylalkyl benzamide derivatives |
| US5496855A (en) * | 1995-01-27 | 1996-03-05 | Smithkline Beecham Corp. | Anti-inflammatory compounds |
| GB0215293D0 (en) * | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
| US7648998B2 (en) * | 2003-12-22 | 2010-01-19 | K.U. Leuven Research & Development | Imidazo 4,5-c pyridine compounds and methods of antiviral treatment |
| AU2005319167B2 (en) * | 2004-12-21 | 2011-09-29 | Gilead Sciences, Inc. | Imidazo[4,5-C]pyridine compound and method of antiviral treatment |
| TW200808695A (en) * | 2006-06-08 | 2008-02-16 | Amgen Inc | Benzamide derivatives and uses related thereto |
| WO2008005519A2 (en) * | 2006-07-07 | 2008-01-10 | Gilead Sciences, Inc. | Novel pyridazine compound and use thereof |
| UA99466C2 (en) | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4281005A (en) * | 1979-03-05 | 1981-07-28 | Merck & Co., Inc. | Novel 2-pyridylimidazole compounds |
| DE2927987A1 (de) * | 1979-07-11 | 1981-02-05 | Thomae Gmbh Dr K | Neue 2-alkoxyphenyl-imidazo eckige klammer auf 4,5-b eckige klammer zu pyridine, deren herstellung und deren verwendung als arzneimittel |
| ZA832938B (en) * | 1982-05-03 | 1984-12-24 | Lilly Co Eli | 2-phenylimidazo(4,5-c)pyridines |
| US4804658A (en) * | 1986-09-15 | 1989-02-14 | G. D. Searle & Co. | Imidazopyridine derivatives and pharmaceutical compositions |
-
1989
- 1989-03-06 US US07/317,871 patent/US5019581A/en not_active Expired - Lifetime
- 1989-03-13 IL IL89588A patent/IL89588A0/xx not_active IP Right Cessation
- 1989-03-13 DK DK121189A patent/DK169872B1/da not_active IP Right Cessation
- 1989-03-13 NO NO891058A patent/NO169965C/no unknown
- 1989-03-13 CA CA000593520A patent/CA1337072C/en not_active Expired - Fee Related
- 1989-03-14 FI FI891200A patent/FI91407C/sv not_active IP Right Cessation
- 1989-03-14 ES ES89104464T patent/ES2061753T3/es not_active Expired - Lifetime
- 1989-03-14 AT AT89104464T patent/ATE112774T1/de active
- 1989-03-14 EP EP89104464A patent/EP0344414B1/en not_active Expired - Lifetime
- 1989-03-14 JP JP1061979A patent/JP2714426B2/ja not_active Expired - Lifetime
- 1989-03-14 NZ NZ228336A patent/NZ228336A/en unknown
- 1989-03-14 DE DE68918755T patent/DE68918755T2/de not_active Expired - Fee Related
- 1989-03-14 KR KR1019890003132A patent/KR890014537A/ko not_active Application Discontinuation
- 1989-03-14 PH PH38328A patent/PH26967A/en unknown
- 1989-03-14 AU AU31270/89A patent/AU625058B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA1337072C (en) | 1995-09-19 |
| US5019581A (en) | 1991-05-28 |
| EP0344414A1 (en) | 1989-12-06 |
| ES2061753T3 (es) | 1994-12-16 |
| DK169872B1 (da) | 1995-03-20 |
| FI91407B (sv) | 1994-03-15 |
| DK121189A (da) | 1989-09-15 |
| NO891058L (no) | 1989-09-15 |
| ATE112774T1 (de) | 1994-10-15 |
| NZ228336A (en) | 1992-01-29 |
| EP0344414B1 (en) | 1994-10-12 |
| NO169965C (no) | 1992-08-26 |
| KR890014537A (ko) | 1989-10-24 |
| FI91407C (sv) | 1994-06-27 |
| DE68918755T2 (de) | 1995-03-09 |
| JP2714426B2 (ja) | 1998-02-16 |
| NO169965B (no) | 1992-05-18 |
| FI891200A0 (sv) | 1989-03-14 |
| AU625058B2 (en) | 1992-07-02 |
| JPH01316378A (ja) | 1989-12-21 |
| IL89588A0 (en) | 1989-09-10 |
| FI891200A (sv) | 1989-09-15 |
| DE68918755D1 (de) | 1994-11-17 |
| DK121189D0 (da) | 1989-03-13 |
| AU3127089A (en) | 1989-09-14 |
| NO891058D0 (no) | 1989-03-13 |
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