JP2014506933A5 - - Google Patents
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- Publication number
- JP2014506933A5 JP2014506933A5 JP2013556883A JP2013556883A JP2014506933A5 JP 2014506933 A5 JP2014506933 A5 JP 2014506933A5 JP 2013556883 A JP2013556883 A JP 2013556883A JP 2013556883 A JP2013556883 A JP 2013556883A JP 2014506933 A5 JP2014506933 A5 JP 2014506933A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- quinoxaline
- methyl
- amino
- isopropyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 23
- 150000002431 hydrogen Chemical class 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000001072 heteroaryl group Chemical group 0.000 claims 19
- -1 stereoisomer Chemical class 0.000 claims 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 238000000034 method Methods 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 125000001188 haloalkyl group Chemical group 0.000 claims 7
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- ZVNLQQKGXZSVPV-UHFFFAOYSA-N 2-(6-methoxypyridin-3-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=NC(OC)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2N=C1N(C)C(C)C ZVNLQQKGXZSVPV-UHFFFAOYSA-N 0.000 claims 4
- NYGQXUZKDABDDD-UHFFFAOYSA-N 2-(furan-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=CO1 NYGQXUZKDABDDD-UHFFFAOYSA-N 0.000 claims 4
- 101000613563 Homo sapiens PAS domain-containing serine/threonine-protein kinase Proteins 0.000 claims 4
- 102100040902 PAS domain-containing serine/threonine-protein kinase Human genes 0.000 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 208000030159 metabolic disease Diseases 0.000 claims 3
- JGQDBVXRYDEWGM-UHFFFAOYSA-N quinoxaline-6-carboxylic acid Chemical compound N1=CC=NC2=CC(C(=O)O)=CC=C21 JGQDBVXRYDEWGM-UHFFFAOYSA-N 0.000 claims 3
- 150000003626 triacylglycerols Chemical class 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- HLFUXGUPGUREQZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-3-(3,4-dihydro-2h-quinolin-1-yl)quinoxaline-6-carboxylic acid Chemical compound C1CCC2=CC=CC=C2N1C1=NC2=CC(C(=O)O)=CC=C2N=C1C1=CC=C(OCO2)C2=C1 HLFUXGUPGUREQZ-UHFFFAOYSA-N 0.000 claims 2
- SEQCVAKNODWCHG-LBPRGKRZSA-N 2-(1,3-benzodioxol-5-yl)-3-[(2s)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid Chemical compound C[C@H]1CCCN1C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(OCO2)C2=C1 SEQCVAKNODWCHG-LBPRGKRZSA-N 0.000 claims 2
- YRKANMKKKIUCMP-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=C2OCOC2=CC(C2=NC3=CC=C(C=C3N=C2N(C)C(C)C)C(O)=O)=C1 YRKANMKKKIUCMP-UHFFFAOYSA-N 0.000 claims 2
- CFNMSJUXFABTQT-ZDUSSCGKSA-N 2-(1-benzofuran-2-yl)-3-[(2s)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid Chemical compound C[C@H]1CCCN1C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC2=CC=CC=C2O1 CFNMSJUXFABTQT-ZDUSSCGKSA-N 0.000 claims 2
- FHNMMCLPYZSVDZ-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-3-[cyclopropyl(methyl)amino]quinoxaline-6-carboxylic acid Chemical compound N=1C2=CC(C(O)=O)=CC=C2N=C(C=2OC3=CC=CC=C3C=2)C=1N(C)C1CC1 FHNMMCLPYZSVDZ-UHFFFAOYSA-N 0.000 claims 2
- CWSJBZCDRYNELY-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4N=C3N(C)C(C)C)C(O)=O)=CC2=C1 CWSJBZCDRYNELY-UHFFFAOYSA-N 0.000 claims 2
- LFCGWAMNIAAUGQ-UHFFFAOYSA-N 2-(1-methylindazol-6-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=C2C=NN(C)C2=CC(C2=NC3=CC=C(C=C3N=C2N(C)C(C)C)C(O)=O)=C1 LFCGWAMNIAAUGQ-UHFFFAOYSA-N 0.000 claims 2
- USZAZKRESYUUIE-UHFFFAOYSA-N 2-(1h-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=C2NN=CC2=CC(C2=NC3=CC=C(C=C3N=C2N(C)C(C)C)C(O)=O)=C1 USZAZKRESYUUIE-UHFFFAOYSA-N 0.000 claims 2
- JRCGWKOBBPLTDZ-UHFFFAOYSA-N 2-(1h-indazol-6-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=C2C=NNC2=CC(C2=NC3=CC=C(C=C3N=C2N(C)C(C)C)C(O)=O)=C1 JRCGWKOBBPLTDZ-UHFFFAOYSA-N 0.000 claims 2
- XGXRTSSELDTWTK-UHFFFAOYSA-N 2-(1h-indol-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=CC=C2NC(C3=NC4=CC=C(C=C4N=C3N(C)C(C)C)C(O)=O)=CC2=C1 XGXRTSSELDTWTK-UHFFFAOYSA-N 0.000 claims 2
- CNSXSBHPCWLUCI-UHFFFAOYSA-N 2-(1h-indol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=C2NC=CC2=CC(C2=NC3=CC=C(C=C3N=C2N(C)C(C)C)C(O)=O)=C1 CNSXSBHPCWLUCI-UHFFFAOYSA-N 0.000 claims 2
- ILQLSGSGRFZPHU-UHFFFAOYSA-N 2-(1h-indol-6-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=C2C=CNC2=CC(C2=NC3=CC=C(C=C3N=C2N(C)C(C)C)C(O)=O)=C1 ILQLSGSGRFZPHU-UHFFFAOYSA-N 0.000 claims 2
- RCCVMGLYQAFOIY-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound O1CCOC2=CC(C3=NC4=CC=C(C=C4N=C3N(C)C(C)C)C(O)=O)=CC=C21 RCCVMGLYQAFOIY-UHFFFAOYSA-N 0.000 claims 2
- KRZULGJBWBRGEQ-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CN=CC(Br)=C1 KRZULGJBWBRGEQ-UHFFFAOYSA-N 0.000 claims 2
- YGQKOJRXHPYFRY-UHFFFAOYSA-N 2-(5-cyanopyridin-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(C#N)C=N1 YGQKOJRXHPYFRY-UHFFFAOYSA-N 0.000 claims 2
- JANPZECAFMRBBL-UHFFFAOYSA-N 2-(5-fluoro-1-benzofuran-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound FC1=CC=C2OC(C3=NC4=CC=C(C=C4N=C3N(C)C(C)C)C(O)=O)=CC2=C1 JANPZECAFMRBBL-UHFFFAOYSA-N 0.000 claims 2
- GQOYPLTYLTWORC-UHFFFAOYSA-N 2-(5-fluoro-1h-indol-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound FC1=CC=C2NC(C3=NC4=CC=C(C=C4N=C3N(C)C(C)C)C(O)=O)=CC2=C1 GQOYPLTYLTWORC-UHFFFAOYSA-N 0.000 claims 2
- WWEVFFRIVAKHLD-UHFFFAOYSA-N 2-(5-fluoropyridin-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(F)C=N1 WWEVFFRIVAKHLD-UHFFFAOYSA-N 0.000 claims 2
- FERDABDGEUBFHB-UHFFFAOYSA-N 2-(5-methoxy-1h-indol-2-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2N=C(N(C)C(C)C)C(C=3NC4=CC=C(C=C4C=3)OC)=NC2=C1 FERDABDGEUBFHB-UHFFFAOYSA-N 0.000 claims 2
- YPQAIUIPIWEOLN-UHFFFAOYSA-N 2-(6-fluoropyridin-3-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(F)N=C1 YPQAIUIPIWEOLN-UHFFFAOYSA-N 0.000 claims 2
- KUPWMFCQISUHSP-UHFFFAOYSA-N 2-[5-methoxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2N=C(N(C)C(C)C)C(C=3N(C(=O)OC(C)(C)C)C4=CC=C(C=C4C=3)OC)=NC2=C1 KUPWMFCQISUHSP-UHFFFAOYSA-N 0.000 claims 2
- WBPJYDOVOKDDEU-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-6-yl-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=CC2=NC=CN2C=C1C1=NC2=CC=C(C(O)=O)C=C2N=C1N(C)C(C)C WBPJYDOVOKDDEU-UHFFFAOYSA-N 0.000 claims 2
- BLVMMHBXXZHNCN-UHFFFAOYSA-N 2-phenyl-3-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]quinoxaline-6-carboxylic acid Chemical compound C1CN(C=2C=CC(=CC=2)C(F)(F)F)CCN1C1=NC2=CC(C(=O)O)=CC=C2N=C1C1=CC=CC=C1 BLVMMHBXXZHNCN-UHFFFAOYSA-N 0.000 claims 2
- MODHPFWYLIVFGN-ZDUSSCGKSA-N 3-[(2s)-2-methylpyrrolidin-1-yl]-2-phenylquinoxaline-6-carboxylic acid Chemical compound C[C@H]1CCCN1C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=CC=C1 MODHPFWYLIVFGN-ZDUSSCGKSA-N 0.000 claims 2
- YHBOSGHZPVZHJA-UHFFFAOYSA-N 3-[butan-2-yl(methyl)amino]-2-(furan-3-yl)quinoxaline-6-carboxylic acid Chemical compound CCC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C=1C=COC=1 YHBOSGHZPVZHJA-UHFFFAOYSA-N 0.000 claims 2
- JRDQPIWWMSUIFP-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-(1h-pyrazol-4-yl)quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C=1C=NNC=1 JRDQPIWWMSUIFP-UHFFFAOYSA-N 0.000 claims 2
- GECQESOIABNQFL-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-(5-methylthiophen-2-yl)quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(C)S1 GECQESOIABNQFL-UHFFFAOYSA-N 0.000 claims 2
- RHPXGFFWAQKXLZ-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-(6-pyrrolidin-1-ylpyridin-3-yl)quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C(C=N1)=CC=C1N1CCCC1 RHPXGFFWAQKXLZ-UHFFFAOYSA-N 0.000 claims 2
- OEPYLQJBIZMUHC-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]quinoxaline-6-carboxylic acid Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C(C3=NC4=CC=C(C=C4N=C3N(C)C(C)C)C(O)=O)=CC2=C1 OEPYLQJBIZMUHC-UHFFFAOYSA-N 0.000 claims 2
- KCVSARQTGWRMQX-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-[5-(trifluoromethyl)-1h-pyrazol-4-yl]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CNN=C1C(F)(F)F KCVSARQTGWRMQX-UHFFFAOYSA-N 0.000 claims 2
- UBVFIAGJSKWPMP-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-[5-(trifluoromethyl)pyridin-2-yl]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(C(F)(F)F)C=N1 UBVFIAGJSKWPMP-UHFFFAOYSA-N 0.000 claims 2
- NJNMZMMUBCJUBI-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-[6-(trifluoromethyl)pyridin-3-yl]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(C(F)(F)F)N=C1 NJNMZMMUBCJUBI-UHFFFAOYSA-N 0.000 claims 2
- APEKBSGYHGDFKW-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-[6-[(2-methylpropan-2-yl)oxycarbonylamino]pyridin-3-yl]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(NC(=O)OC(C)(C)C)N=C1 APEKBSGYHGDFKW-UHFFFAOYSA-N 0.000 claims 2
- GGZSTHJCJLFQGE-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-pyridin-3-ylquinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=CN=C1 GGZSTHJCJLFQGE-UHFFFAOYSA-N 0.000 claims 2
- NBFBCBUZNAPMHI-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-pyridin-4-ylquinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=NC=C1 NBFBCBUZNAPMHI-UHFFFAOYSA-N 0.000 claims 2
- KSFBFGMTIZTXTJ-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-quinolin-3-ylquinoxaline-6-carboxylic acid Chemical compound C1=CC=CC2=CC(C3=NC4=CC=C(C=C4N=C3N(C)C(C)C)C(O)=O)=CN=C21 KSFBFGMTIZTXTJ-UHFFFAOYSA-N 0.000 claims 2
- LBVJIOYUNKVJGB-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-thiophen-2-ylquinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=CS1 LBVJIOYUNKVJGB-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- JXWYOCARONMUEH-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-6-(2h-tetrazol-5-yl)quinoxaline Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(C=3NN=NN=3)C=C2N=C1C1=CC=C(OC)C=C1 JXWYOCARONMUEH-UHFFFAOYSA-N 0.000 claims 1
- XKCVTJZYYCAGBO-UHFFFAOYSA-N 2,3-bis(4-phenylpiperidin-1-yl)quinoxaline-6-carboxylic acid Chemical compound C1CC(C=2C=CC=CC=2)CCN1C1=NC2=CC(C(=O)O)=CC=C2N=C1N(CC1)CCC1C1=CC=CC=C1 XKCVTJZYYCAGBO-UHFFFAOYSA-N 0.000 claims 1
- GKYXNXDROGWCFH-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-3-[butan-2-yl(methyl)amino]quinoxaline-6-carboxylic acid Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4N=C3N(C)C(C)CC)C(O)=O)=CC2=C1 GKYXNXDROGWCFH-UHFFFAOYSA-N 0.000 claims 1
- GNRXVCZFRPECGI-UHFFFAOYSA-N 2-(2-fluorophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=CC=C1F GNRXVCZFRPECGI-UHFFFAOYSA-N 0.000 claims 1
- ZWCJLTGYJAFRFZ-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(F)C(F)=C1 ZWCJLTGYJAFRFZ-UHFFFAOYSA-N 0.000 claims 1
- JMDMGVXBOASNDN-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=CC(F)=C1 JMDMGVXBOASNDN-UHFFFAOYSA-N 0.000 claims 1
- SAZXAYVKLHFVGW-UHFFFAOYSA-N 2-(3-methoxyphenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound COC1=CC=CC(C=2C(=NC3=CC(=CC=C3N=2)C(O)=O)N(C)C(C)C)=C1 SAZXAYVKLHFVGW-UHFFFAOYSA-N 0.000 claims 1
- PWGUMJNASSFPEW-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(Cl)C=C1 PWGUMJNASSFPEW-UHFFFAOYSA-N 0.000 claims 1
- NNIZYTUOCXKYCZ-UHFFFAOYSA-N 2-(4-cyanophenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(C#N)C=C1 NNIZYTUOCXKYCZ-UHFFFAOYSA-N 0.000 claims 1
- ZRGDEEHQBXOIQU-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(3-methylpiperidin-1-yl)quinoxaline-6-carboxylic acid Chemical compound C1C(C)CCCN1C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(F)C=C1 ZRGDEEHQBXOIQU-UHFFFAOYSA-N 0.000 claims 1
- JSWQYEUTVFKVSA-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(3-oxopiperazin-1-yl)quinoxaline-6-carboxylic acid Chemical compound C1CNC(=O)CN1C1=NC2=CC(C(=O)O)=CC=C2N=C1C1=CC=C(F)C=C1 JSWQYEUTVFKVSA-UHFFFAOYSA-N 0.000 claims 1
- KONRKDNGLRDGCS-MRXNPFEDSA-N 2-(4-fluorophenyl)-3-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]quinoxaline-6-carboxylic acid Chemical compound COC[C@H]1CCCN1C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(F)C=C1 KONRKDNGLRDGCS-MRXNPFEDSA-N 0.000 claims 1
- RNXGPLPQCMLPKK-INIZCTEOSA-N 2-(4-fluorophenyl)-3-[(2s)-2-methyl-4-pyridin-2-ylpiperazin-1-yl]quinoxaline-6-carboxylic acid Chemical compound C([C@@H]1C)N(C=2N=CC=CC=2)CCN1C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(F)C=C1 RNXGPLPQCMLPKK-INIZCTEOSA-N 0.000 claims 1
- BXYWNNBCTFBNED-ZDUSSCGKSA-N 2-(4-fluorophenyl)-3-[(2s)-2-methylpiperidin-1-yl]quinoxaline-6-carboxylic acid Chemical compound C[C@H]1CCCCN1C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(F)C=C1 BXYWNNBCTFBNED-ZDUSSCGKSA-N 0.000 claims 1
- DZRUCRKWBXDZRX-LBPRGKRZSA-N 2-(4-fluorophenyl)-3-[(2s)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylic acid Chemical compound C[C@H]1CCCN1C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(F)C=C1 DZRUCRKWBXDZRX-LBPRGKRZSA-N 0.000 claims 1
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- VBZITIJQDVOHQY-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-(4-morpholin-4-ylphenyl)quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C(C=C1)=CC=C1N1CCOCC1 VBZITIJQDVOHQY-UHFFFAOYSA-N 0.000 claims 1
- HUUWVMRTOMEUIK-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]-2-[4-(trifluoromethoxy)phenyl]quinoxaline-6-carboxylic acid Chemical compound CC(C)N(C)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=C(OC(F)(F)F)C=C1 HUUWVMRTOMEUIK-UHFFFAOYSA-N 0.000 claims 1
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- BAGVMYQIIZVDCW-INIZCTEOSA-N 3-[methyl-[(1s)-1-phenylethyl]amino]-2-phenylquinoxaline-6-carboxylic acid Chemical compound CN([C@@H](C)C=1C=CC=CC=1)C1=NC2=CC(C(O)=O)=CC=C2N=C1C1=CC=CC=C1 BAGVMYQIIZVDCW-INIZCTEOSA-N 0.000 claims 1
- OIRPGAZNLOQRDX-UHFFFAOYSA-N 3-indol-1-yl-2-phenylquinoxaline-6-carboxylic acid Chemical compound C1=CC2=CC=CC=C2N1C1=NC2=CC(C(=O)O)=CC=C2N=C1C1=CC=CC=C1 OIRPGAZNLOQRDX-UHFFFAOYSA-N 0.000 claims 1
- RVIHPCCTLCBNIH-UHFFFAOYSA-N 3-morpholin-4-yl-2-phenylquinoxaline-6-carboxylic acid Chemical compound C1COCCN1C1=NC2=CC(C(=O)O)=CC=C2N=C1C1=CC=CC=C1 RVIHPCCTLCBNIH-UHFFFAOYSA-N 0.000 claims 1
- VBOLZYIAZQWHMQ-UHFFFAOYSA-N 3-phenyl-2-piperidin-1-ylquinoxaline-6-carboxylic acid Chemical compound C=1C=CC=CC=1C1=NC2=CC(C(=O)O)=CC=C2N=C1N1CCCCC1 VBOLZYIAZQWHMQ-UHFFFAOYSA-N 0.000 claims 1
- 102000007513 Hemoglobin A Human genes 0.000 claims 1
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- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
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- IYWVRFMWSYCCTO-UHFFFAOYSA-N O(C)C1=CC=C(C=C1)C1=NC2=CC=C(C=C2N=C1)C(=O)O Chemical compound O(C)C1=CC=C(C=C1)C1=NC2=CC=C(C=C2N=C1)C(=O)O IYWVRFMWSYCCTO-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 241000270666 Testudines Species 0.000 claims 1
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- LNTSWYUOHQDHBB-UHFFFAOYSA-N butyl 2-(4-fluorophenyl)-3-piperidin-1-ylquinoxaline-6-carboxylate Chemical compound C1CCCCN1C1=NC2=CC(C(=O)OCCCC)=CC=C2N=C1C1=CC=C(F)C=C1 LNTSWYUOHQDHBB-UHFFFAOYSA-N 0.000 claims 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
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| PCT/US2012/027423 WO2012119046A2 (en) | 2011-03-02 | 2012-03-02 | Heterocyclic compounds for the inhibition of pask |
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| JP2014506933A JP2014506933A (ja) | 2014-03-20 |
| JP2014506933A5 true JP2014506933A5 (https=) | 2015-04-16 |
| JP6139415B2 JP6139415B2 (ja) | 2017-05-31 |
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| JP (1) | JP6139415B2 (https=) |
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| BR (1) | BR112013022147A2 (https=) |
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| PH12012500382A1 (en) * | 2009-09-03 | 2012-10-22 | Bioenergenix | Heterocyclic compounds for the inhibition of pask |
| JP2016507538A (ja) * | 2013-02-07 | 2016-03-10 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 置換キノキサリン誘導体およびｍＧｌｕＲ４の正のアロステリックモジュレーターとしてのそれらの使用 |
| US9936700B2 (en) | 2013-10-23 | 2018-04-10 | Bayer Cropscience Aktiengesellschaft | Substituted quinoxaline derivatives as pest control agent |
| US10144742B2 (en) | 2014-04-18 | 2018-12-04 | Millennium Pharmaceuticals, Inc. | Quinoxaline compounds and uses thereof |
| EP3247705B1 (en) | 2015-01-20 | 2019-11-20 | Millennium Pharmaceuticals, Inc. | Quinazoline and quinoline compounds and uses thereof as nampt inhibitors |
| EP3395803A1 (en) | 2017-04-28 | 2018-10-31 | Institut Pasteur | Imidazopyrazine derivatives, process for preparation thereof, and their uses as luciferins |
| CN107652278A (zh) * | 2017-08-09 | 2018-02-02 | 江苏工程职业技术学院 | 一种依帕列净的合成工艺 |
| CN112062687B (zh) * | 2020-09-02 | 2023-11-21 | 上海信谊万象药业股份有限公司 | 一种盐酸阿扎司琼中间体3-氨基-5-氯-2-羟基苯甲酸甲酯的合成方法 |
| CN115197155B (zh) * | 2022-07-25 | 2023-10-24 | 宝鸡文理学院 | 一种2-喹喔啉磺酸酯类化合物及其合成方法 |
| AU2024249981A1 (en) | 2023-04-06 | 2025-10-16 | Pfizer Inc. | Substituted indazole propionic acid derivative compounds and uses thereof as ampk activators |
Family Cites Families (24)
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| CH419399A (de) | 1962-07-18 | 1966-08-31 | Ciba Geigy | Verfahren zur Herstellung neuer Küpenfarbstoffe |
| HUT64023A (en) | 1991-03-22 | 1993-11-29 | Sandoz Ag | Process for producing aminoguanidine derivatives and pharmaceutical compositions comprising such compounds |
| US6331555B1 (en) | 1995-06-01 | 2001-12-18 | University Of California | Treatment of platelet derived growth factor related disorders such as cancers |
| WO1999042461A1 (en) * | 1998-02-23 | 1999-08-26 | Warner-Lambert Company | Substituted quinoxaline derivatives as interleukin-8 receptor antagonists |
| CO5150173A1 (es) | 1998-12-10 | 2002-04-29 | Novartis Ag | Compuestos n-(glicilo sustituido)-2-cianopirrolidinas inhibidores de peptidasa de dipeptidilo-iv (dpp-iv) los cuales son efectivos en el tratamiento de condiciones mediadas por la inhibicion de dpp-iv |
| JP2002534512A (ja) * | 1999-01-15 | 2002-10-15 | ノボ ノルディスク アクティーゼルスカブ | 非ペプチドｇｌｐ−１アゴニスト |
| DE10013318A1 (de) | 2000-03-17 | 2001-09-20 | Merck Patent Gmbh | Formulierung enthaltend Chinoxalinderivate |
| FR2816940A1 (fr) | 2000-11-23 | 2002-05-24 | Lipha | Derives de 4-(biphenylcarbonylamino)-piperidine, compositions les contenant et leur utilisation |
| US6319679B1 (en) | 2001-01-26 | 2001-11-20 | Board Of Regents, The University Of Texas System | PAS kinase |
| US7189724B2 (en) | 2003-04-15 | 2007-03-13 | Valeant Research And Development | Quinoxaline derivatives having antiviral activity |
| WO2005007099A2 (en) * | 2003-07-10 | 2005-01-27 | Imclone Systems Incorporated | Pkb inhibitors as anti-tumor agents |
| JP2008527002A (ja) | 2005-01-13 | 2008-07-24 | サートリス ファーマシューティカルズ， インコーポレイテッド | 神経変性障害および血液凝固障害を予防および処置するための新規組成物 |
| WO2006079021A2 (en) | 2005-01-20 | 2006-07-27 | Sirtris Pharmaceuticals, Inc. | Use of sirtuin-activating compounds for treating flushing and drug induced weight gain |
| CN101115479A (zh) | 2005-02-14 | 2008-01-30 | 默克公司 | Akt活性抑制剂 |
| WO2006138418A2 (en) | 2005-06-14 | 2006-12-28 | President And Fellows Of Harvard College | Improvement of cognitive performance with sirtuin activators |
| AU2006283846B2 (en) * | 2005-08-26 | 2012-04-05 | Merck Serono Sa | Pyrazine derivatives and use as PI3K inhibitors |
| EP2029734A4 (en) | 2006-06-08 | 2009-11-25 | Univ Utah Res Found | PAS KINASE AS ENERGY HOME GOST CONTROL |
| CA2752150A1 (en) | 2009-02-11 | 2010-08-19 | Reaction Biology Corp. | Selective kinase inhibitors |
| WO2010101230A1 (ja) * | 2009-03-05 | 2010-09-10 | アステラス製薬株式会社 | キノキサリン化合物 |
| SI2440547T1 (sl) | 2009-06-12 | 2023-05-31 | Abivax | Nove kemične molekule, ki zavirajo mehanizem spajanja za zdravljenje bolezni, ki so posledica napak pri spajanju |
| PH12012500382A1 (en) * | 2009-09-03 | 2012-10-22 | Bioenergenix | Heterocyclic compounds for the inhibition of pask |
| EP2661428B1 (en) * | 2010-12-23 | 2017-06-07 | Merck Sharp & Dohme Corp. | Quinoxalines and aza-quinoxalines as crth2 receptor modulators |
| CA2823753C (en) * | 2011-01-05 | 2019-03-12 | Bioenergenix Llc | Heterocyclic compounds for the inhibition of pask |
| US8916561B2 (en) * | 2011-03-02 | 2014-12-23 | Bioenergenix, Llc | Substituted quinoxaline compounds for the inhibition of PASK |
-
2012
- 2012-03-02 BR BR112013022147A patent/BR112013022147A2/pt not_active Application Discontinuation
- 2012-03-02 JP JP2013556883A patent/JP6139415B2/ja not_active Expired - Fee Related
- 2012-03-02 CA CA2828349A patent/CA2828349C/en active Active
- 2012-03-02 WO PCT/US2012/027423 patent/WO2012119046A2/en not_active Ceased
- 2012-03-02 AU AU2012223232A patent/AU2012223232B2/en not_active Ceased
- 2012-03-02 EP EP12751925.4A patent/EP2681207B1/en not_active Not-in-force
- 2012-03-02 CN CN201280016906.1A patent/CN103459382B/zh not_active Expired - Fee Related
- 2012-03-02 US US13/410,650 patent/US8912188B2/en active Active
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