JP2011502958A5 - - Google Patents

Info

Publication number

JP2011502958A5

JP2011502958A5 JP2010513226A JP2010513226A JP2011502958A5 JP 2011502958 A5 JP2011502958 A5 JP 2011502958A5 JP 2010513226 A JP2010513226 A JP 2010513226A JP 2010513226 A JP2010513226 A JP 2010513226A JP 2011502958 A5 JP2011502958 A5 JP 2011502958A5

Authority

JP

Japan

Prior art keywords

optionally substituted

alkyl

substituted

alkoxy

membered

Prior art date

2008-06-18

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.)

Pending

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• 125000000217 alkyl group Chemical group 0.000 claims description 85
• 125000001424 substituent group Chemical group 0.000 claims description 83
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 56
• 125000003545 alkoxy group Chemical group 0.000 claims description 49
• 150000001875 compounds Chemical class 0.000 claims description 39
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 37
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 30
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
• 125000004122 cyclic group Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 21
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 11
• 239000011780 sodium chloride Substances 0.000 claims description 11
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 11
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 7
• 206010012601 Diabetes mellitus Diseases 0.000 claims description 6
• 102000019622 EC 2.7.1.2 Human genes 0.000 claims description 6
• 108010021582 EC 2.7.1.2 Proteins 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 235000020824 obesity Nutrition 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 239000000651 prodrug Substances 0.000 claims description 4
• 229940002612 prodrugs Drugs 0.000 claims description 4
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
• 230000003213 activating Effects 0.000 claims description 3
• 239000012190 activator Substances 0.000 claims description 3
• 230000003449 preventive Effects 0.000 claims description 3
• JWOBNEHDHYVFCE-UHFFFAOYSA-N 1-[3-[[5-(3-chloropyridin-2-yl)-7-(4-methylsulfonylphenoxy)-1H-indazol-3-yl]amino]pyrazol-1-yl]-3-methoxypropan-2-ol Chemical compound COCC(O)CN1C=CC(NC=2C3=CC(=CC(OC=4C=CC(=CC=4)S(C)(=O)=O)=C3NN=2)C=2C(=CC=CN=2)Cl)=N1 JWOBNEHDHYVFCE-UHFFFAOYSA-N 0.000 claims description 2
• QMNLFESRKFDJKN-UHFFFAOYSA-N 3-[3-[[5-(3-chloropyridin-2-yl)-7-(4-methylsulfonylphenoxy)-1H-indazol-3-yl]amino]pyrazol-1-yl]propane-1,2-diol Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1=CC(C=2C(=CC=CN=2)Cl)=CC2=C1NN=C2NC1=NN(CC(O)CO)C=C1 QMNLFESRKFDJKN-UHFFFAOYSA-N 0.000 claims description 2
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• XHRSNKXQNOEURE-QHCPKHFHSA-N 5-[5-[(2S)-2-amino-3-phenylpropoxy]-2-(furan-3-yl)pyridin-3-yl]-N-pyridin-4-yl-1H-indazol-3-amine Chemical compound C([C@@H](N)CC=1C=CC=CC=1)OC(C=C1C=2C=C3C(NC=4C=CN=CC=4)=NNC3=CC=2)=CN=C1C=1C=COC=1 XHRSNKXQNOEURE-QHCPKHFHSA-N 0.000 claims description 2
• DBWSCCYHZFYDPD-UHFFFAOYSA-N N-(1-methylpyrazol-3-yl)-7-(4-methylsulfonylphenoxy)-5-propan-2-yloxy-1H-indazol-3-amine Chemical compound C=12NN=C(NC3=NN(C)C=C3)C2=CC(OC(C)C)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 DBWSCCYHZFYDPD-UHFFFAOYSA-N 0.000 claims description 2
• JVWNHPQEHDJEAP-UHFFFAOYSA-N N-(1-methylpyrazol-3-yl)-7-(4-methylsulfonylphenoxy)-5-propan-2-ylsulfonyl-1H-indazol-3-amine Chemical compound C=12NN=C(NC3=NN(C)C=C3)C2=CC(S(=O)(=O)C(C)C)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 JVWNHPQEHDJEAP-UHFFFAOYSA-N 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
• -1 3-Chloropyridin-2-yl Chemical group 0.000 claims 3
• 238000004519 manufacturing process Methods 0.000 claims 2
• 150000001412 amines Chemical class 0.000 claims 1
• 230000000694 effects Effects 0.000 description 2
• APSKFKXHWBUQNE-UHFFFAOYSA-N 5-(3-chloropyridin-2-yl)-1-methyl-N-(1-methylpyrazol-3-yl)-7-(4-methylsulfonylphenoxy)indazol-3-amine Chemical compound CN1C=CC(NC=2C3=CC(=CC(OC=4C=CC(=CC=4)S(C)(=O)=O)=C3N(C)N=2)C=2C(=CC=CN=2)Cl)=N1 APSKFKXHWBUQNE-UHFFFAOYSA-N 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1