JP2018503695A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018503695A5 JP2018503695A5 JP2017559273A JP2017559273A JP2018503695A5 JP 2018503695 A5 JP2018503695 A5 JP 2018503695A5 JP 2017559273 A JP2017559273 A JP 2017559273A JP 2017559273 A JP2017559273 A JP 2017559273A JP 2018503695 A5 JP2018503695 A5 JP 2018503695A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfonylquinolin
- quinolin
- methyl
- hydroxy
- sulfonyl
- Prior art date
- 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.)
- Granted
Links
- -1 nitro, amino Chemical group 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000002252 acyl group Chemical group 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 102000006378 Catechol O-methyltransferase Human genes 0.000 claims 5
- 108020002739 Catechol O-methyltransferase Proteins 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- IEXDDOHFWPCFPN-UHFFFAOYSA-N 2-sulfonyl-1H-quinolin-8-ol Chemical compound C1=CC(=S(=O)=O)NC2=C1C=CC=C2O IEXDDOHFWPCFPN-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- ZFIPGDYMEOPFBO-UHFFFAOYSA-N 1-[1-(8-hydroxyquinolin-5-yl)sulfonyl-4-phenylpiperidin-4-yl]ethanone Chemical compound OC=1C=CC(=C2C=CC=NC=12)S(=O)(=O)N1CCC(CC1)(C1=CC=CC=C1)C(C)=O ZFIPGDYMEOPFBO-UHFFFAOYSA-N 0.000 claims 2
- DNSFGHSGVGDXEU-UHFFFAOYSA-N 2-[4-(8-hydroxyquinolin-5-yl)sulfonylpiperazin-1-yl]benzonitrile Chemical compound OC=1C=CC(=C2C=CC=NC=12)S(=O)(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 DNSFGHSGVGDXEU-UHFFFAOYSA-N 0.000 claims 2
- RIZHDDNLZFFZRL-UHFFFAOYSA-N 5-(1,3-dihydroisoindol-2-ylsulfonyl)quinolin-8-ol Chemical compound C1N(CC2=CC=CC=C12)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O RIZHDDNLZFFZRL-UHFFFAOYSA-N 0.000 claims 2
- NHQXGAHTSKJSET-UHFFFAOYSA-N 5-(2,4-dimethylphenyl)sulfonylquinolin-8-ol Chemical compound CC1=C(C=CC(=C1)C)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O NHQXGAHTSKJSET-UHFFFAOYSA-N 0.000 claims 2
- QAUBWXTZKQAPJV-UHFFFAOYSA-N 5-(2-benzylpyrrolidin-1-yl)sulfonylquinolin-8-ol Chemical compound C(C1=CC=CC=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O QAUBWXTZKQAPJV-UHFFFAOYSA-N 0.000 claims 2
- OTMPWXWGYKCOPL-UHFFFAOYSA-N 5-(2-cyclohexylpyrrolidin-1-yl)sulfonylquinolin-8-ol Chemical compound C1(CCCCC1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O OTMPWXWGYKCOPL-UHFFFAOYSA-N 0.000 claims 2
- HQCGUKNZFDEIGX-UHFFFAOYSA-N 5-(2-methylpiperazin-1-yl)sulfonylquinolin-8-ol Chemical compound CC1N(CCNC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O HQCGUKNZFDEIGX-UHFFFAOYSA-N 0.000 claims 2
- ZDUKBKIIVMGTRJ-UHFFFAOYSA-N 5-(2-methylpyrrolidin-1-yl)sulfonylquinolin-8-ol Chemical compound CC1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O ZDUKBKIIVMGTRJ-UHFFFAOYSA-N 0.000 claims 2
- OOKLCIGVNIRLKS-UHFFFAOYSA-N 5-(2-phenylpiperidin-1-yl)sulfonylquinolin-8-ol Chemical compound C1(=CC=CC=C1)C1N(CCCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O OOKLCIGVNIRLKS-UHFFFAOYSA-N 0.000 claims 2
- IPHCWHZPCCDKHI-UHFFFAOYSA-N 5-(2-phenylpyrrolidin-1-yl)sulfonylquinolin-8-ol Chemical compound C1(=CC=CC=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O IPHCWHZPCCDKHI-UHFFFAOYSA-N 0.000 claims 2
- ZLJILJFTRCBERB-UHFFFAOYSA-N 5-(2-propan-2-ylpyrrolidin-1-yl)sulfonylquinolin-8-ol Chemical compound C(C)(C)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O ZLJILJFTRCBERB-UHFFFAOYSA-N 0.000 claims 2
- QKXPTZQVFLQLSI-UHFFFAOYSA-N 5-(2-pyridin-2-ylpyrrolidin-1-yl)sulfonylquinolin-8-ol Chemical compound N1=C(C=CC=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O QKXPTZQVFLQLSI-UHFFFAOYSA-N 0.000 claims 2
- ODODNLVATSLLCU-UHFFFAOYSA-N 5-(2-pyridin-3-ylpyrrolidin-1-yl)sulfonylquinolin-8-ol Chemical compound N1=CC(=CC=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O ODODNLVATSLLCU-UHFFFAOYSA-N 0.000 claims 2
- CCBOOKWVGICORX-UHFFFAOYSA-N 5-(2-pyridin-4-ylpyrrolidin-1-yl)sulfonylquinolin-8-ol Chemical compound N1=CC=C(C=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O CCBOOKWVGICORX-UHFFFAOYSA-N 0.000 claims 2
- BCDSUNISTQCJAQ-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)sulfonylquinolin-8-ol Chemical compound ClC=1C=C(C=CC=1Cl)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O BCDSUNISTQCJAQ-UHFFFAOYSA-N 0.000 claims 2
- HEKZRCXBIXZYSL-UHFFFAOYSA-N 5-(3,4-dihydro-1H-isoquinolin-2-ylsulfonyl)quinolin-8-ol Chemical compound C1N(CCC2=CC=CC=C12)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O HEKZRCXBIXZYSL-UHFFFAOYSA-N 0.000 claims 2
- NFIJXJHJAKXVPQ-UHFFFAOYSA-N 5-(3,4-dimethylphenyl)sulfonylquinolin-8-ol Chemical compound CC=1C=C(C=CC=1C)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O NFIJXJHJAKXVPQ-UHFFFAOYSA-N 0.000 claims 2
- PYIUKACMZFDXCR-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)sulfonylquinolin-8-ol Chemical compound ClC=1C=C(C=C(C=1)Cl)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O PYIUKACMZFDXCR-UHFFFAOYSA-N 0.000 claims 2
- ZFFHTMWUBKRTPM-UHFFFAOYSA-N 5-(3,5-dimethylphenyl)sulfonylquinolin-8-ol Chemical compound CC=1C=C(C=C(C=1)C)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O ZFFHTMWUBKRTPM-UHFFFAOYSA-N 0.000 claims 2
- VAAPIZMCBLYZPS-UHFFFAOYSA-N 5-(3-azabicyclo[3.2.2]nonan-3-ylsulfonyl)quinolin-8-ol Chemical compound C12CN(CC(CC1)CC2)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O VAAPIZMCBLYZPS-UHFFFAOYSA-N 0.000 claims 2
- LXUBFOBOPVDEDU-UHFFFAOYSA-N 5-(3-chlorophenyl)sulfonylquinolin-8-ol Chemical compound ClC=1C=C(C=CC=1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O LXUBFOBOPVDEDU-UHFFFAOYSA-N 0.000 claims 2
- FCDNEHBEULNNQB-UHFFFAOYSA-N 5-(3-methylphenyl)sulfonylquinolin-8-ol Chemical compound C1(=CC(=CC=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)C FCDNEHBEULNNQB-UHFFFAOYSA-N 0.000 claims 2
- DMWDXZSGHLJQDY-UHFFFAOYSA-N 5-(3-methylpyridin-4-yl)sulfonylquinolin-8-ol Chemical compound CC=1C=NC=CC=1S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O DMWDXZSGHLJQDY-UHFFFAOYSA-N 0.000 claims 2
- DAQWAROHGUHDBX-UHFFFAOYSA-N 5-(3-phenylphenyl)sulfonylquinolin-8-ol Chemical compound C1(=CC=CC=C1)C=1C=C(C=CC=1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O DAQWAROHGUHDBX-UHFFFAOYSA-N 0.000 claims 2
- YRDKBSOFQIOXCM-UHFFFAOYSA-N 5-(3-phenylpiperidin-1-yl)sulfonylquinolin-8-ol Chemical compound C1(=CC=CC=C1)C1CN(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O YRDKBSOFQIOXCM-UHFFFAOYSA-N 0.000 claims 2
- HAJDUDDXPMXFTB-UHFFFAOYSA-N 5-(3-pyridin-4-ylphenyl)sulfonylquinolin-8-ol Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O HAJDUDDXPMXFTB-UHFFFAOYSA-N 0.000 claims 2
- NAQRVWDLPJFTBD-UHFFFAOYSA-N 5-(3-quinolin-5-ylphenyl)sulfonylquinolin-8-ol Chemical compound N1=CC=CC2=C(C=CC=C12)C=1C=C(C=CC=1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O NAQRVWDLPJFTBD-UHFFFAOYSA-N 0.000 claims 2
- UDRUPJVZCWIIJC-UHFFFAOYSA-N 5-(4-benzylpiperazin-1-yl)sulfonylquinolin-8-ol Chemical compound C(C1=CC=CC=C1)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O UDRUPJVZCWIIJC-UHFFFAOYSA-N 0.000 claims 2
- ICQCDLCQJRWZHD-UHFFFAOYSA-N 5-(4-benzylpiperidin-1-yl)sulfonylquinolin-8-ol Chemical compound C(C1=CC=CC=C1)C1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O ICQCDLCQJRWZHD-UHFFFAOYSA-N 0.000 claims 2
- GMHWNIXRWXIRLM-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonylquinolin-8-ol Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O GMHWNIXRWXIRLM-UHFFFAOYSA-N 0.000 claims 2
- BATFUFNHZGFLAH-UHFFFAOYSA-N 5-(4-fluoro-2-methylphenyl)sulfonylquinolin-8-ol Chemical compound FC1=CC(=C(C=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)C BATFUFNHZGFLAH-UHFFFAOYSA-N 0.000 claims 2
- LSIKCYXHYSPENC-UHFFFAOYSA-N 5-(4-fluorophenyl)sulfonylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O LSIKCYXHYSPENC-UHFFFAOYSA-N 0.000 claims 2
- RXKZVEKGWQCYMG-UHFFFAOYSA-N 5-(4-hydroxy-4-phenylpiperidin-1-yl)sulfonylquinolin-8-ol Chemical compound OC1(CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)C1=CC=CC=C1 RXKZVEKGWQCYMG-UHFFFAOYSA-N 0.000 claims 2
- LYYJBDBNQIZSSM-UHFFFAOYSA-N 5-(4-methylphenyl)sulfonyl-7-(trifluoromethyl)quinolin-8-ol Chemical compound C1(=CC=C(C=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C(=C1)C(F)(F)F)O)C LYYJBDBNQIZSSM-UHFFFAOYSA-N 0.000 claims 2
- QEBJHOCNVFTONG-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)sulfonylquinolin-8-ol Chemical compound CN1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O QEBJHOCNVFTONG-UHFFFAOYSA-N 0.000 claims 2
- OOZSATRKKKFSIB-UHFFFAOYSA-N 5-(4-phenylpiperazin-1-yl)sulfonylquinolin-8-ol Chemical compound C1(=CC=CC=C1)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O OOZSATRKKKFSIB-UHFFFAOYSA-N 0.000 claims 2
- GAIYYAIPEZIUPA-UHFFFAOYSA-N 5-(4-phenylpiperidin-1-yl)sulfonylquinolin-8-ol Chemical compound C1(=CC=CC=C1)C1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O GAIYYAIPEZIUPA-UHFFFAOYSA-N 0.000 claims 2
- YKJKZYCOQAHXMQ-UHFFFAOYSA-N 5-(4-tert-butylphenyl)sulfonylquinolin-8-ol Chemical compound C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O YKJKZYCOQAHXMQ-UHFFFAOYSA-N 0.000 claims 2
- IPAPQLTWQRFISK-UHFFFAOYSA-N 5-(6,8-dihydro-5H-1,7-naphthyridin-7-ylsulfonyl)quinolin-8-ol Chemical compound N1=CC=CC=2CCN(CC1=2)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O IPAPQLTWQRFISK-UHFFFAOYSA-N 0.000 claims 2
- XSPJEBKFJZFPKU-GHMZBOCLSA-N 5-[(3R,4R)-3,4-difluoropyrrolidin-1-yl]sulfonyl-7-methylquinolin-8-ol Chemical compound F[C@@H]1CN(C[C@H]1F)S(=O)(=O)C1=C2C=CC=NC2=C(C(=C1)C)O XSPJEBKFJZFPKU-GHMZBOCLSA-N 0.000 claims 2
- QXYIDPIZWCBFEW-NXEZZACHSA-N 5-[(3R,4R)-3,4-difluoropyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound F[C@@H]1CN(C[C@H]1F)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O QXYIDPIZWCBFEW-NXEZZACHSA-N 0.000 claims 2
- ZIOMWWMOYKFGTL-UHFFFAOYSA-N 5-[(4-methylphenyl)methylsulfonyl]quinolin-8-ol Chemical compound C1(=CC=C(C=C1)CS(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)C ZIOMWWMOYKFGTL-UHFFFAOYSA-N 0.000 claims 2
- QSQKLXQADABXOQ-UHFFFAOYSA-N 5-[1-(2,3-dimethylphenyl)piperidin-4-yl]sulfonylquinolin-8-ol Chemical compound CC1=C(C=CC=C1C)N1CCC(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O QSQKLXQADABXOQ-UHFFFAOYSA-N 0.000 claims 2
- YDDKUFRMCSJBHI-UHFFFAOYSA-N 5-[1-(4-fluorophenyl)piperidin-4-yl]sulfonylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)N1CCC(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O YDDKUFRMCSJBHI-UHFFFAOYSA-N 0.000 claims 2
- MWNLNLQINZMEQR-UHFFFAOYSA-N 5-[1-[(2,3-dichlorophenyl)methyl]piperidin-4-yl]sulfonylquinolin-8-ol Chemical compound ClC1=C(C=CC=C1Cl)CN1CCC(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O MWNLNLQINZMEQR-UHFFFAOYSA-N 0.000 claims 2
- LJTMIPLLHVALTJ-UHFFFAOYSA-N 5-[1-[(2-chlorophenyl)methyl]benzimidazol-4-yl]sulfonylquinolin-8-ol Chemical compound ClC1=C(C=CC=C1)CN1C=NC2=C1C=CC=C2S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O LJTMIPLLHVALTJ-UHFFFAOYSA-N 0.000 claims 2
- IGFGKPFDSPDZIU-UHFFFAOYSA-N 5-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]sulfonylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)CN1CCC(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O IGFGKPFDSPDZIU-UHFFFAOYSA-N 0.000 claims 2
- DDJMHXLHMBEUSK-UHFFFAOYSA-N 5-[2-(2-methylpropyl)pyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound C(C(C)C)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O DDJMHXLHMBEUSK-UHFFFAOYSA-N 0.000 claims 2
- XXVFKKGCSRRAQP-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)pyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O XXVFKKGCSRRAQP-UHFFFAOYSA-N 0.000 claims 2
- KVIBDRGTQXFYTK-UHFFFAOYSA-N 5-[2-(4-methoxyphenyl)pyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound COC1=CC=C(C=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O KVIBDRGTQXFYTK-UHFFFAOYSA-N 0.000 claims 2
- UUDYQHUODWGOAB-UHFFFAOYSA-N 5-[2-(4-methylphenyl)ethylsulfonyl]quinolin-8-ol Chemical compound C1(=CC=C(C=C1)CCS(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)C UUDYQHUODWGOAB-UHFFFAOYSA-N 0.000 claims 2
- AJSDWXILBJWIBH-UHFFFAOYSA-N 5-[2-(trifluoromethyl)phenyl]sulfonylquinolin-8-ol Chemical compound FC(C1=C(C=CC=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)(F)F AJSDWXILBJWIBH-UHFFFAOYSA-N 0.000 claims 2
- PRSNERMPJAWKJB-UHFFFAOYSA-N 5-[2-[2-(trifluoromethyl)phenyl]pyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound FC(C1=C(C=CC=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)(F)F PRSNERMPJAWKJB-UHFFFAOYSA-N 0.000 claims 2
- BPHQWOLJSMRPRQ-UHFFFAOYSA-N 5-[3-(1H-indazol-4-yl)phenyl]sulfonylquinolin-8-ol Chemical compound N1N=CC2=C(C=CC=C12)C=1C=C(C=CC=1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O BPHQWOLJSMRPRQ-UHFFFAOYSA-N 0.000 claims 2
- FHTJALIMYUERIE-UHFFFAOYSA-N 5-[3-(3-chloro-4-fluorophenyl)phenyl]sulfonylquinolin-8-ol Chemical compound ClC=1C=C(C=CC=1F)C=1C=C(C=CC=1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O FHTJALIMYUERIE-UHFFFAOYSA-N 0.000 claims 2
- CLSBPBKRROYZMM-UHFFFAOYSA-N 5-[3-(4-fluorophenyl)pyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)C1CN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O CLSBPBKRROYZMM-UHFFFAOYSA-N 0.000 claims 2
- AFRKEPQRXPFWOQ-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]sulfonylquinolin-8-ol Chemical compound FC(C=1C=C(C=CC=1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)(F)F AFRKEPQRXPFWOQ-UHFFFAOYSA-N 0.000 claims 2
- OOWQLDGQXCUUBB-UHFFFAOYSA-N 5-[3-[4-(trifluoromethoxy)phenoxy]azetidin-1-yl]sulfonylquinolin-8-ol Chemical compound FC(OC1=CC=C(OC2CN(C2)S(=O)(=O)C2=C3C=CC=NC3=C(C=C2)O)C=C1)(F)F OOWQLDGQXCUUBB-UHFFFAOYSA-N 0.000 claims 2
- ICGSOXWEMRTCKD-UHFFFAOYSA-N 5-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound S1N=C(C2=C1C=CC=C2)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O ICGSOXWEMRTCKD-UHFFFAOYSA-N 0.000 claims 2
- MQLMMHQXBVHLIE-UHFFFAOYSA-N 5-[4-(2,3-dichlorophenyl)piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound ClC1=C(C=CC=C1Cl)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O MQLMMHQXBVHLIE-UHFFFAOYSA-N 0.000 claims 2
- CJVZYEOSAJNRSQ-UHFFFAOYSA-N 5-[4-(2,3-dimethylphenyl)piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound CC1=C(C=CC=C1C)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O CJVZYEOSAJNRSQ-UHFFFAOYSA-N 0.000 claims 2
- IQIFWRJIZBTGER-UHFFFAOYSA-N 5-[4-(2,5-dimethylphenyl)piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound CC1=C(C=C(C=C1)C)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O IQIFWRJIZBTGER-UHFFFAOYSA-N 0.000 claims 2
- PEIMDPIKWOMNGC-UHFFFAOYSA-N 5-[4-(2-phenylphenyl)piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound C1(=CC=CC=C1)C1=C(C=CC=C1)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O PEIMDPIKWOMNGC-UHFFFAOYSA-N 0.000 claims 2
- LDAZRBBYTKRXKJ-UHFFFAOYSA-N 5-[4-(3-methoxypropyl)piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound COCCCN1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O LDAZRBBYTKRXKJ-UHFFFAOYSA-N 0.000 claims 2
- ATCKEPPWMBNBBD-UHFFFAOYSA-N 5-[4-(4-fluorophenyl)piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O ATCKEPPWMBNBBD-UHFFFAOYSA-N 0.000 claims 2
- AKLAPUMDVPBAOA-UHFFFAOYSA-N 5-[4-(5-chloropyridin-2-yl)piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound ClC=1C=CC(=NC=1)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O AKLAPUMDVPBAOA-UHFFFAOYSA-N 0.000 claims 2
- QZQSLHOKWGDYGA-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]sulfonylquinolin-8-ol Chemical compound FC(C1=CC=C(C=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)(F)F QZQSLHOKWGDYGA-UHFFFAOYSA-N 0.000 claims 2
- RWCMURLFQHFZLI-UHFFFAOYSA-N 5-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]sulfonyl-7-methylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)CN1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C(=C1)C)O RWCMURLFQHFZLI-UHFFFAOYSA-N 0.000 claims 2
- CRZXWYWJUKPFBT-UHFFFAOYSA-N 5-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)CN1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O CRZXWYWJUKPFBT-UHFFFAOYSA-N 0.000 claims 2
- HHSPIMDSWHCSLK-UHFFFAOYSA-N 5-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound FC(C1=CC=C(C=C1)N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)(F)F HHSPIMDSWHCSLK-UHFFFAOYSA-N 0.000 claims 2
- KAWNPSSQNBPDAB-UHFFFAOYSA-N 5-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound FC1=CC=C(C=C1)C(N1CCN(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)C1=CC=C(C=C1)F KAWNPSSQNBPDAB-UHFFFAOYSA-N 0.000 claims 2
- GRUAQHMZTJKOCA-UHFFFAOYSA-N 5-cyclohexylsulfonylquinolin-8-ol Chemical compound C1(CCCCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O GRUAQHMZTJKOCA-UHFFFAOYSA-N 0.000 claims 2
- MXZPWFQESQPBKT-UHFFFAOYSA-N 5-cyclopentylsulfonyl-7-(trifluoromethyl)quinolin-8-ol Chemical compound C1(CCCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C(=C1)C(F)(F)F)O MXZPWFQESQPBKT-UHFFFAOYSA-N 0.000 claims 2
- RRXFHJFZWNODIX-UHFFFAOYSA-N 5-cyclopentylsulfonylquinolin-8-ol Chemical compound C1(CCCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O RRXFHJFZWNODIX-UHFFFAOYSA-N 0.000 claims 2
- ZVIWFUADCRHDPT-UHFFFAOYSA-N 5-ethylsulfonylquinolin-8-ol Chemical compound C(C)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O ZVIWFUADCRHDPT-UHFFFAOYSA-N 0.000 claims 2
- JQXYICGFVXAWTQ-UHFFFAOYSA-N 5-naphthalen-2-ylsulfonylquinolin-8-ol Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O JQXYICGFVXAWTQ-UHFFFAOYSA-N 0.000 claims 2
- LWJXTYUDMCFARN-UHFFFAOYSA-N 5-piperazin-1-ylsulfonylquinolin-8-ol Chemical compound N1(CCNCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O LWJXTYUDMCFARN-UHFFFAOYSA-N 0.000 claims 2
- MBTFVARZIXJQSB-UHFFFAOYSA-N 5-piperidin-4-ylsulfonylquinolin-8-ol Chemical compound N1CCC(CC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O MBTFVARZIXJQSB-UHFFFAOYSA-N 0.000 claims 2
- PPSOCWRLVDEITN-UHFFFAOYSA-N 5-pyridin-2-ylsulfonylquinolin-8-ol Chemical compound N1=C(C=CC=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O PPSOCWRLVDEITN-UHFFFAOYSA-N 0.000 claims 2
- BOIHWFCLCMKIBY-UHFFFAOYSA-N 5-pyridin-3-ylsulfonylquinolin-8-ol Chemical compound N1=CC(=CC=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O BOIHWFCLCMKIBY-UHFFFAOYSA-N 0.000 claims 2
- YSOHRRHBVMWCJS-UHFFFAOYSA-N 5-pyridin-4-ylsulfonylquinolin-8-ol Chemical compound N1=CC=C(C=C1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O YSOHRRHBVMWCJS-UHFFFAOYSA-N 0.000 claims 2
- JTZCHFRFKIBKPT-UHFFFAOYSA-N 7-bromo-5-(4-methylphenyl)sulfonylquinolin-8-ol Chemical compound BrC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)C1=CC=C(C=C1)C JTZCHFRFKIBKPT-UHFFFAOYSA-N 0.000 claims 2
- OBSGEUGZFKKFHM-UHFFFAOYSA-N 7-bromo-5-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound BrC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)N1CCN(CC1)CC1=CC=C(C=C1)F OBSGEUGZFKKFHM-UHFFFAOYSA-N 0.000 claims 2
- ADMSKNRXIHLTJX-GFCCVEGCSA-N 7-bromo-8-hydroxy-N-methyl-N-[(1R)-1-phenylethyl]quinoline-5-sulfonamide Chemical compound BrC=1C=C(C=2C=CC=NC=2C=1O)S(=O)(=O)N([C@H](C)C1=CC=CC=C1)C ADMSKNRXIHLTJX-GFCCVEGCSA-N 0.000 claims 2
- KVRFOWUPRJDLSD-UHFFFAOYSA-N 7-chloro-5-(4-methylphenyl)sulfonylquinolin-8-ol Chemical compound ClC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)C1=CC=C(C=C1)C KVRFOWUPRJDLSD-UHFFFAOYSA-N 0.000 claims 2
- YVPSBJPWEYLUOZ-VIFPVBQESA-N 7-chloro-5-[(2S)-2-methylpyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound ClC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)N1[C@H](CCC1)C YVPSBJPWEYLUOZ-VIFPVBQESA-N 0.000 claims 2
- PQMFMSARNHGQIY-UHFFFAOYSA-N 7-chloro-5-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound ClC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)N1CCN(CC1)CC1=CC=C(C=C1)F PQMFMSARNHGQIY-UHFFFAOYSA-N 0.000 claims 2
- VCHNXVLBTUUCTB-GFCCVEGCSA-N 7-chloro-8-hydroxy-N-methyl-N-[(1R)-1-phenylethyl]quinoline-5-sulfonamide Chemical compound ClC=1C=C(C=2C=CC=NC=2C=1O)S(=O)(=O)N([C@H](C)C1=CC=CC=C1)C VCHNXVLBTUUCTB-GFCCVEGCSA-N 0.000 claims 2
- VRULDRRQTAPONR-UHFFFAOYSA-N 7-fluoro-5-(4-methylphenyl)sulfonylquinolin-8-ol Chemical compound FC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)C1=CC=C(C=C1)C VRULDRRQTAPONR-UHFFFAOYSA-N 0.000 claims 2
- WFUSUYCAIATMDK-UHFFFAOYSA-N 7-fluoro-5-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]sulfonylquinolin-8-ol Chemical compound FC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)N1CCN(CC1)CC1=CC=C(C=C1)F WFUSUYCAIATMDK-UHFFFAOYSA-N 0.000 claims 2
- HKRVLLQKYWVTID-UHFFFAOYSA-N 7-fluoro-5-pyrrolidin-1-ylsulfonylquinolin-8-ol Chemical compound FC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)N1CCCC1 HKRVLLQKYWVTID-UHFFFAOYSA-N 0.000 claims 2
- MDUAOVTZPSQZBE-GFCCVEGCSA-N 7-fluoro-8-hydroxy-N-methyl-N-[(1R)-1-phenylethyl]quinoline-5-sulfonamide Chemical compound FC=1C=C(C=2C=CC=NC=2C=1O)S(=O)(=O)N([C@H](C)C1=CC=CC=C1)C MDUAOVTZPSQZBE-GFCCVEGCSA-N 0.000 claims 2
- SRSRUSQJVVDJGM-UHFFFAOYSA-N 7-iodo-5-(4-methylphenyl)sulfonylquinolin-8-ol Chemical compound IC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)C1=CC=C(C=C1)C SRSRUSQJVVDJGM-UHFFFAOYSA-N 0.000 claims 2
- DTPZWHQTSZIFFP-UHFFFAOYSA-N 7-methyl-5-pyrrolidin-1-ylsulfonylquinolin-8-ol Chemical compound CC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)N1CCCC1 DTPZWHQTSZIFFP-UHFFFAOYSA-N 0.000 claims 2
- APWAJFHSGLWJDY-UHFFFAOYSA-N 8-(8-hydroxyquinolin-5-yl)sulfonyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound OC=1C=CC(=C2C=CC=NC=12)S(=O)(=O)N1CCC2(C(NCN2C2=CC=CC=C2)=O)CC1 APWAJFHSGLWJDY-UHFFFAOYSA-N 0.000 claims 2
- IODSITPDYKRLBM-CQSZACIVSA-N 8-hydroxy-N,7-dimethyl-N-[(1R)-1-phenylethyl]quinoline-5-sulfonamide Chemical compound OC1=C(C=C(C=2C=CC=NC1=2)S(=O)(=O)N([C@H](C)C1=CC=CC=C1)C)C IODSITPDYKRLBM-CQSZACIVSA-N 0.000 claims 2
- UHOVHABLVJBVJJ-UHFFFAOYSA-N 8-hydroxy-N-[(3-methoxyphenyl)methyl]-N-methylquinoline-5-sulfonamide Chemical compound OC1=CC=C(C=2C=CC=NC1=2)S(=O)(=O)N(C)CC1=CC(=CC=C1)OC UHOVHABLVJBVJJ-UHFFFAOYSA-N 0.000 claims 2
- LDYYTZXFTUGGBC-UHFFFAOYSA-N 8-hydroxy-N-methyl-N-(2-phenylethyl)quinoline-5-sulfonamide Chemical compound OC1=CC=C(C=2C=CC=NC1=2)S(=O)(=O)N(CCC1=CC=CC=C1)C LDYYTZXFTUGGBC-UHFFFAOYSA-N 0.000 claims 2
- JHMKMVKYPIMJRX-UHFFFAOYSA-N 8-hydroxy-N-methyl-N-(4-methylphenyl)quinoline-5-sulfonamide Chemical compound OC1=CC=C(C=2C=CC=NC1=2)S(=O)(=O)N(C)C1=CC=C(C=C1)C JHMKMVKYPIMJRX-UHFFFAOYSA-N 0.000 claims 2
- JQRULMYEJLRMMW-CYBMUJFWSA-N 8-hydroxy-N-methyl-N-[(1R)-1-phenylethyl]quinoline-5-sulfonamide Chemical compound OC1=CC=C(C=2C=CC=NC1=2)S(=O)(=O)N([C@H](C)C1=CC=CC=C1)C JQRULMYEJLRMMW-CYBMUJFWSA-N 0.000 claims 2
- JQRULMYEJLRMMW-ZDUSSCGKSA-N 8-hydroxy-N-methyl-N-[(1S)-1-phenylethyl]quinoline-5-sulfonamide Chemical compound OC1=CC=C(C=2C=CC=NC1=2)S(=O)(=O)N([C@@H](C)C1=CC=CC=C1)C JQRULMYEJLRMMW-ZDUSSCGKSA-N 0.000 claims 2
- JZRDZKJJEVQQRU-UHFFFAOYSA-N 8-hydroxy-N-methyl-N-[[4-(trifluoromethyl)phenyl]methyl]quinoline-5-sulfonamide Chemical compound FC(C1=CC=C(C=C1)CN(S(=O)(=O)C=1C=2C=CC=NC=2C(=CC=1)O)C)(F)F JZRDZKJJEVQQRU-UHFFFAOYSA-N 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- AVGRRZDOFCSBMM-UHFFFAOYSA-N N-[(2-fluorophenyl)methyl]-8-hydroxy-N-methylquinoline-5-sulfonamide Chemical compound FC1=C(C=CC=C1)CN(S(=O)(=O)C=1C=2C=CC=NC=2C(=CC=1)O)C AVGRRZDOFCSBMM-UHFFFAOYSA-N 0.000 claims 2
- GZKRSFBLZINCLA-UHFFFAOYSA-N N-[(3-chlorophenyl)methyl]-8-hydroxy-N-methylquinoline-5-sulfonamide Chemical compound ClC=1C=C(C=CC=1)CN(S(=O)(=O)C=1C=2C=CC=NC=2C(=CC=1)O)C GZKRSFBLZINCLA-UHFFFAOYSA-N 0.000 claims 2
- CVYQXPUGNKYKPO-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-8-hydroxy-N-methylquinoline-5-sulfonamide Chemical compound FC1=CC=C(C=C1)CN(S(=O)(=O)C=1C=2C=CC=NC=2C(=CC=1)O)C CVYQXPUGNKYKPO-UHFFFAOYSA-N 0.000 claims 2
- ZNVWTUWMJORNKF-UHFFFAOYSA-N N-benzyl-8-hydroxy-N-methylquinoline-5-sulfonamide Chemical compound CN(CC1=CC=CC=C1)S(=O)(=O)C1=C2C=CC=NC2=C(O)C=C1 ZNVWTUWMJORNKF-UHFFFAOYSA-N 0.000 claims 2
- IITMZWKCRAYEKS-UHFFFAOYSA-N N-benzyl-N-[2-(dimethylamino)ethyl]-8-hydroxyquinoline-5-sulfonamide Chemical compound C(C1=CC=CC=C1)N(S(=O)(=O)C=1C=2C=CC=NC=2C(=CC=1)O)CCN(C)C IITMZWKCRAYEKS-UHFFFAOYSA-N 0.000 claims 2
- BYUXLQLGJORZMZ-UHFFFAOYSA-N N-benzyl-N-ethyl-8-hydroxyquinoline-5-sulfonamide Chemical compound C(C1=CC=CC=C1)N(S(=O)(=O)C=1C=2C=CC=NC=2C(=CC=1)O)CC BYUXLQLGJORZMZ-UHFFFAOYSA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- FZCCHDPYMVRQFS-UHFFFAOYSA-N [1-(8-hydroxyquinolin-5-yl)sulfonylpiperidin-4-yl]-phenylmethanone Chemical compound OC=1C=CC(=C2C=CC=NC=12)S(=O)(=O)N1CCC(CC1)C(=O)C1=CC=CC=C1 FZCCHDPYMVRQFS-UHFFFAOYSA-N 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- MWVPQZRIWVPJCA-UHFFFAOYSA-N propylcyclopropane Chemical compound CCCC1CC1 MWVPQZRIWVPJCA-UHFFFAOYSA-N 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- ZHBSLKKTJCVEBO-UHFFFAOYSA-N tert-butyl 4-(8-hydroxyquinolin-5-yl)sulfonyl-3-methylpiperazine-1-carboxylate Chemical compound OC=1C=CC(=C2C=CC=NC=12)S(=O)(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)C ZHBSLKKTJCVEBO-UHFFFAOYSA-N 0.000 claims 2
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- 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 1
- RRUWBHNILFGCMO-UHFFFAOYSA-N 5-(4-methoxyphenyl)sulfonylquinolin-8-ol Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=CC=C(O)C2=NC=CC=C12 RRUWBHNILFGCMO-UHFFFAOYSA-N 0.000 claims 1
- ZCPYGPOWCHKHAR-UHFFFAOYSA-N 5-(4-methylphenyl)sulfonylquinolin-8-ol Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC=C(O)C2=NC=CC=C12 ZCPYGPOWCHKHAR-UHFFFAOYSA-N 0.000 claims 1
- VTJJCUYCRNLTNI-UHFFFAOYSA-N 5-(benzenesulfonyl)quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1S(=O)(=O)C1=CC=CC=C1 VTJJCUYCRNLTNI-UHFFFAOYSA-N 0.000 claims 1
- BURANDKWIDAPDU-UHFFFAOYSA-N 5-[2-(2-methylphenyl)pyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound C1(=C(C=CC=C1)C1N(CCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O)C BURANDKWIDAPDU-UHFFFAOYSA-N 0.000 claims 1
- RQWYQCNLAJJRFQ-UHFFFAOYSA-N 5-piperidin-1-ylsulfonylquinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1S(=O)(=O)N1CCCCC1 RQWYQCNLAJJRFQ-UHFFFAOYSA-N 0.000 claims 1
- YSJMMJFKKLXNQF-UHFFFAOYSA-N 5-pyrrolidin-1-ylsulfonylquinolin-8-ol Chemical compound N1(CCCC1)S(=O)(=O)C1=C2C=CC=NC2=C(C=C1)O YSJMMJFKKLXNQF-UHFFFAOYSA-N 0.000 claims 1
- YVPSBJPWEYLUOZ-SECBINFHSA-N 7-chloro-5-[(2R)-2-methylpyrrolidin-1-yl]sulfonylquinolin-8-ol Chemical compound ClC1=CC(=C2C=CC=NC2=C1O)S(=O)(=O)N1[C@@H](CCC1)C YVPSBJPWEYLUOZ-SECBINFHSA-N 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 208000030990 Impulse-control disease Diseases 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- 208000009668 Neurobehavioral Manifestations Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- RMMQSEUXENRTHV-UHFFFAOYSA-N n,n-diethyl-8-hydroxyquinoline-5-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N(CC)CC)=CC=C(O)C2=N1 RMMQSEUXENRTHV-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 150000003235 pyrrolidines Chemical class 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 201000006152 substance dependence Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562109954P | 2015-01-30 | 2015-01-30 | |
| US62/109,954 | 2015-01-30 | ||
| PCT/US2016/015832 WO2016123576A1 (en) | 2015-01-30 | 2016-01-29 | Comt inhibiting methods and compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018503695A JP2018503695A (ja) | 2018-02-08 |
| JP2018503695A5 true JP2018503695A5 (https=) | 2019-07-11 |
| JP6858712B2 JP6858712B2 (ja) | 2021-04-14 |
Family
ID=56544443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017559273A Active JP6858712B2 (ja) | 2015-01-30 | 2016-01-29 | Ｃｏｍｔ阻害方法及び組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US10035799B2 (https=) |
| EP (1) | EP3250209B1 (https=) |
| JP (1) | JP6858712B2 (https=) |
| CA (1) | CA2975398C (https=) |
| WO (1) | WO2016123576A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016123577A1 (en) | 2015-01-30 | 2016-08-04 | Lieber Institute For Brain Development | Comt inhibiting methods and compositions |
| US11021514B2 (en) | 2016-06-01 | 2021-06-01 | Athira Pharma, Inc. | Compounds |
| WO2018036498A1 (en) * | 2016-08-24 | 2018-03-01 | National Institute Of Biological Sciences, Beijing | Entacapone-related compounds to treat macular degeneration |
| JP2023533016A (ja) | 2020-07-11 | 2023-08-01 | ファイザー・インク | 抗ウイルス性ヘテロアリールケトン誘導体 |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
| AU2022314068A1 (en) | 2021-07-23 | 2024-01-18 | LeonaBio, Inc. | Methods of treating parkinson's disease and/or lewy body disease or disorder(s) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4997946A (en) | 1987-08-18 | 1991-03-05 | Eastman Kodak Company | Process for the iodination of hydroxyaromatic and aminoaromatic compounds |
| AU722662B2 (en) | 1996-05-20 | 2000-08-10 | Darwin Discovery Limited | Quinoline sulfonamides as TNF inhibitors and as PDE-IV inhibitors |
| GB0130696D0 (en) * | 2001-12-21 | 2002-02-06 | Smithkline Beecham Plc | Chemical Compounds |
| AU2002950217A0 (en) | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
| EA200600225A1 (ru) | 2003-08-14 | 2006-08-25 | Пфайзер Инк. | Производные пиперазина для лечения вич инфекций |
| BRPI0721213B1 (pt) | 2007-01-31 | 2021-11-09 | Bial - Portela & Ca, S.A. | Uso de nitrocatecóis substituídos, e embalagem |
| CN102149369B (zh) | 2008-04-18 | 2016-08-10 | 因泰克制药有限公司 | 卡比多巴/左旋多巴胃滞留给药 |
| EP2542076B1 (en) | 2010-03-04 | 2021-01-13 | Merck Sharp & Dohme Corp. | Inhibitors of catechol o-methyl transferase and their use in the treatment of psychotic disorders |
| GB201004372D0 (en) * | 2010-03-16 | 2010-04-28 | Almac Sciences Scotland Ltd | Compounds for purification |
| US20140186280A1 (en) * | 2010-08-13 | 2014-07-03 | Varinel Inc | Neuroprotective and neuro-restorative iron chelators and monoamine oxidase inhibitors and uses thereof |
| DK2620436T3 (en) | 2010-09-24 | 2018-07-30 | Shionogi & Co | Substituted polycyclic carbamoylpyridone derivative prodrug |
| WO2016123577A1 (en) | 2015-01-30 | 2016-08-04 | Lieber Institute For Brain Development | Comt inhibiting methods and compositions |
-
2016
- 2016-01-29 JP JP2017559273A patent/JP6858712B2/ja active Active
- 2016-01-29 US US15/011,353 patent/US10035799B2/en active Active
- 2016-01-29 WO PCT/US2016/015832 patent/WO2016123576A1/en not_active Ceased
- 2016-01-29 EP EP16744242.5A patent/EP3250209B1/en active Active
- 2016-01-29 CA CA2975398A patent/CA2975398C/en active Active
-
2018
- 2018-06-26 US US16/018,496 patent/US10479790B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018503695A5 (https=) | ||
| CN107108637B (zh) | 三唑并嘧啶化合物及其用途 | |
| US10968203B2 (en) | Pyrimidinyl-pyridyloxy-naphthyl compounds and methods of treating IRE1-related diseases and disorders | |
| EP3310779B1 (en) | Compounds and compositions for inhibiting the activity of shp2 | |
| JP6342393B2 (ja) | 置換型ピラゾロン化合物及び使用方法 | |
| AU2015365465B2 (en) | Amido thiadiazole derivatives as NADPH Oxidase inhibitors | |
| JP2020521730A5 (https=) | ||
| TW201819386A (zh) | Shp2磷酸酶抑制劑及其使用方法 | |
| CN110769822A (zh) | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 | |
| EP3710002A2 (en) | Degraders and degrons for targeted protein degradation | |
| RU2008137927A (ru) | Ингибиторы тирозинкиназ | |
| JP2015510938A5 (https=) | ||
| CA3071760A1 (en) | Combination of atr kinase inhibitors and pd-1/pd-l1 inhibitors | |
| JP2017530185A5 (https=) | ||
| CN107530430A (zh) | 用于预防和/或治疗肌萎缩性侧索硬化症的药剂 | |
| JP2017528515A5 (https=) | ||
| JP2014506590A5 (https=) | ||
| CN107667092A (zh) | 作为fgfr4抑制剂的甲酰化n‑杂环衍生物 | |
| JP2020503302A5 (https=) | ||
| RU2019123319A (ru) | Пиразолопиримидины и способы их применения | |
| JP2017526659A5 (https=) | ||
| JP2013529206A5 (https=) | ||
| CN109896997A (zh) | N－酰基苯胺类c－Met激酶抑制剂的制备方法及其用途 | |
| JP2019537581A5 (https=) | ||
| JP2018522062A5 (https=) |