KR20090026129A - 티아졸릴디하이드로인다졸 - Google Patents

Info

Publication number

KR20090026129A

KR20090026129A KR1020087027299A KR20087027299A KR20090026129A KR 20090026129 A KR20090026129 A KR 20090026129A KR 1020087027299 A KR1020087027299 A KR 1020087027299A KR 20087027299 A KR20087027299 A KR 20087027299A KR 20090026129 A KR20090026129 A KR 20090026129A

Authority

KR

South Korea

Prior art keywords

alkyl

cycloalkyl

formula

alkynyl

alkenyl

Prior art date

2006-04-06

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.)

Withdrawn

Links

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• 239000002253 acid Substances 0.000 claims abstract description 34
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• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 23
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 16
• 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 claims abstract description 13
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• 150000001875 compounds Chemical class 0.000 claims description 145
• -1 -C 6 -C 14 - aryl Chemical group 0.000 claims description 116
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 239000013543 active substance Substances 0.000 claims description 43
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 29
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
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• 229910052731 fluorine Inorganic materials 0.000 claims description 22
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• 230000000694 effects Effects 0.000 claims description 16
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• 229910052794 bromium Inorganic materials 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 14
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
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• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 7
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
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• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
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• 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 claims description 4
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• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
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• 206010046851 Uveitis Diseases 0.000 claims description 3
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• 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims description 3
• 229940125715 antihistaminic agent Drugs 0.000 claims description 3
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• 230000001580 bacterial effect Effects 0.000 claims description 3
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• 229960001334 corticosteroids Drugs 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 229940052760 dopamine agonists Drugs 0.000 claims description 3
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• 208000024963 hair loss Diseases 0.000 claims description 3
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• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
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• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
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