HRP20030719A2 - Triazolopyridines as anri-inflammatory agents - Google Patents
Triazolopyridines as anri-inflammatory agents Download PDFInfo
- Publication number
- HRP20030719A2 HRP20030719A2 HR20030719A HRP20030719A HRP20030719A2 HR P20030719 A2 HRP20030719 A2 HR P20030719A2 HR 20030719 A HR20030719 A HR 20030719A HR P20030719 A HRP20030719 A HR P20030719A HR P20030719 A2 HRP20030719 A2 HR P20030719A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- phenyl
- heteroaryl
- cycloalkyl
- heterocycle
- Prior art date
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- 150000008523 triazolopyridines Chemical class 0.000 title description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 581
- 150000001875 compounds Chemical class 0.000 claims description 385
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 158
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 127
- 125000000623 heterocyclic group Chemical group 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 113
- 239000001257 hydrogen Substances 0.000 claims description 111
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 110
- -1 phenyl- Chemical group 0.000 claims description 103
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 93
- 125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims description 88
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 82
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 80
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 75
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 62
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 60
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 50
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 201000010099 disease Diseases 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 241000124008 Mammalia Species 0.000 claims description 22
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 21
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 20
- 230000005764 inhibitory process Effects 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
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- 102000043136 MAP kinase family Human genes 0.000 claims description 10
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
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- QSVDXGHEPKIJAK-UHFFFAOYSA-N 2-methyl-4-phenyl-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC(C)=NC=1C1=CC=CC=C1 QSVDXGHEPKIJAK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
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- GGUWFBJTYKFSCP-UHFFFAOYSA-N 4-phenyl-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=CC=C1 GGUWFBJTYKFSCP-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 3
- LXNCCRGRUITJBS-UHFFFAOYSA-N 4-(3-methylphenyl)-5-(3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1,3-oxazole Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=CC(C)=C1 LXNCCRGRUITJBS-UHFFFAOYSA-N 0.000 claims description 3
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- JEJAABNZDXVBDR-UHFFFAOYSA-N 5-(3-ethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-(3-methylphenyl)-1,3-oxazole Chemical compound C=1N2C(CC)=NN=C2C=CC=1C=1OC=NC=1C1=CC=CC(C)=C1 JEJAABNZDXVBDR-UHFFFAOYSA-N 0.000 claims description 3
- HVGGHEUBVDQWKM-UHFFFAOYSA-N 5-(3-ethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-(4-fluorophenyl)-1,3-oxazole Chemical compound C=1N2C(CC)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 HVGGHEUBVDQWKM-UHFFFAOYSA-N 0.000 claims description 3
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- 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
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Landscapes
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US27484001P | 2001-03-09 | 2001-03-09 | |
PCT/IB2002/000424 WO2002072579A1 (en) | 2001-03-09 | 2002-02-08 | Triazolopyridines as anti-inflammatory agents |
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HRP20030719A2 true HRP20030719A2 (en) | 2005-04-30 |
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HR20030719A HRP20030719A2 (en) | 2001-03-09 | 2003-09-09 | Triazolopyridines as anri-inflammatory agents |
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DE (1) | DE60210755T2 (no) |
DO (1) | DOP2002000353A (no) |
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EC (1) | ECSP034762A (no) |
EE (1) | EE200300437A (no) |
ES (1) | ES2260415T3 (no) |
GT (1) | GT200200042A (no) |
HR (1) | HRP20030719A2 (no) |
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IL (1) | IL156567A0 (no) |
IS (1) | IS6858A (no) |
MA (1) | MA26991A1 (no) |
MX (1) | MXPA03008144A (no) |
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UY (1) | UY27199A1 (no) |
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GB0124933D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124931D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124934D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
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