PH12014501947B1 - Serine/threonine kinase inhibitors - Google Patents

Info

Publication number

PH12014501947B1

PH12014501947B1 PH12014501947A PH12014501947A PH12014501947B1 PH 12014501947 B1 PH12014501947 B1 PH 12014501947B1 PH 12014501947 A PH12014501947 A PH 12014501947A PH 12014501947 A PH12014501947 A PH 12014501947A PH 12014501947 B1 PH12014501947 B1 PH 12014501947B1

Authority

PH

Philippines

Prior art keywords

optionally substituted

groups

methyl

certain embodiments

alkyl

Prior art date

2012-03-01

Links

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• 229940043355 kinase inhibitor Drugs 0.000 title description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 title description 2
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 227
• 150000003839 salts Chemical class 0.000 claims abstract description 60
• 229940002612 prodrug Drugs 0.000 claims abstract description 13
• 239000000651 prodrug Substances 0.000 claims abstract description 13
• -1 1-hydroxypropan- 2-yl Chemical group 0.000 claims description 1215
• 125000000217 alkyl group Chemical group 0.000 claims description 234
• 229910052736 halogen Inorganic materials 0.000 claims description 170
• 150000002367 halogens Chemical class 0.000 claims description 170
• 229910052757 nitrogen Inorganic materials 0.000 claims description 149
• 125000000623 heterocyclic group Chemical group 0.000 claims description 139
• 229910052717 sulfur Inorganic materials 0.000 claims description 139
• 125000005842 heteroatom Chemical group 0.000 claims description 136
• 229910052760 oxygen Inorganic materials 0.000 claims description 128
• 239000001257 hydrogen Substances 0.000 claims description 100
• 229910052739 hydrogen Inorganic materials 0.000 claims description 100
• 125000001072 heteroaryl group Chemical group 0.000 claims description 84
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 69
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 63
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
• 229910052799 carbon Inorganic materials 0.000 claims description 43
• 229920006395 saturated elastomer Polymers 0.000 claims description 38
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
• 150000002431 hydrogen Chemical group 0.000 claims description 18
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 11
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 11
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 11
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 11
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 11
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 11
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
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• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 9
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 9
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• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 7
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 7
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 7
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 7
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 7
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• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims 3
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