ES2921020T3 - Compuestos de indol sustituidos con [1,2,4]triazolo[4,3-a]piridinilo - Google Patents

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Publication number

ES2921020T3

ES2921020T3 ES18759464T ES18759464T ES2921020T3 ES 2921020 T3 ES2921020 T3 ES 2921020T3 ES 18759464 T ES18759464 T ES 18759464T ES 18759464 T ES18759464 T ES 18759464T ES 2921020 T3 ES2921020 T3 ES 2921020T3

Authority

ES

Spain

Prior art keywords

triazolo

indol

isopropyl

piperidin

pyridine

Prior art date

2017-08-04

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.)

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• -1 [1,2,4]triazolo[4,3-a]pyridinyl-substituted indole compounds Chemical class 0.000 title claims description 122
• 150000001875 compounds Chemical class 0.000 claims abstract description 139
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 96
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 39
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 25
• 239000012453 solvate Substances 0.000 claims description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 18
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 17
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 17
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 201000006417 multiple sclerosis Diseases 0.000 claims description 13
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 13
• 239000003937 drug carrier Substances 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
• NSOKIUUDFLTYEO-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CC(C)NC(C)C1)C1=CN2C=NN=C2C(C)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CC(C)NC(C)C1)C1=CN2C=NN=C2C(C)=C1C NSOKIUUDFLTYEO-UHFFFAOYSA-N 0.000 claims description 8
• 125000003566 oxetanyl group Chemical group 0.000 claims description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 4
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• SKXYTQIWDVBAHO-UHFFFAOYSA-N COCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2C=NN=C2C(C)=C1 Chemical compound COCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2C=NN=C2C(C)=C1 SKXYTQIWDVBAHO-UHFFFAOYSA-N 0.000 claims description 4
• XCAIHLXEHHIJGQ-UHFFFAOYSA-N N=1N=CN2C=1C=CC(=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)C)=O Chemical compound N=1N=CN2C=1C=CC(=C2)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CN(C)C)=O XCAIHLXEHHIJGQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
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• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
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