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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| 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 |
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| KR101650981B1 (ko) | 2009-09-03 | 2016-08-24 | 바이오에너제닉스 | Ｐａｓｋ의 억제를 위한 복소환 화합물 |
| US20150374687A1 (en) * | 2013-02-07 | 2015-12-31 | Merck Patent Gmbh | Substituted quinoxaline derivatives and their use as positive allosteric modulators of mglur4 |
| EP3060557A1 (de) | 2013-10-23 | 2016-08-31 | Bayer CropScience Aktiengesellschaft | Substituierte chinoxalin-derivate als schädlingsbekämpfungsmittel |
| 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 |
| WO2000042026A1 (en) * | 1999-01-15 | 2000-07-20 | Novo Nordisk A/S | Non-peptide glp-1 agonists |
| 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 |
| AU2006204699B2 (en) | 2005-01-13 | 2012-04-26 | Sirtris Pharmaceuticals, Inc. | Novel compositions for preventing and treating neurodegenerative and blood coagulation disorders |
| WO2006079021A2 (en) | 2005-01-20 | 2006-07-27 | Sirtris Pharmaceuticals, Inc. | Use of sirtuin-activating compounds for treating flushing and drug induced weight gain |
| WO2006091395A2 (en) | 2005-02-14 | 2006-08-31 | Merck & Co., Inc. | Inhibitors of akt activity |
| WO2006138418A2 (en) | 2005-06-14 | 2006-12-28 | President And Fellows Of Harvard College | Improvement of cognitive performance with sirtuin activators |
| JP5226513B2 (ja) * | 2005-08-26 | 2013-07-03 | メルク セローノ ソシエテ アノニム | ピラジン誘導体及びその使用 |
| US20100256220A1 (en) | 2006-06-08 | 2010-10-07 | University Of Utah Research Foundation | PAS Kinase Regulates Energy Homeostasis |
| CA2752150A1 (en) | 2009-02-11 | 2010-08-19 | Reaction Biology Corp. | Selective kinase inhibitors |
| MX2011009314A (es) * | 2009-03-05 | 2011-10-11 | Astellas Pharma Inc | Compuesto de quinoxalina. |
| WO2010143169A2 (en) | 2009-06-12 | 2010-12-16 | Société Splicos | Compounds useful for treating aids |
| KR101650981B1 (ko) * | 2009-09-03 | 2016-08-24 | 바이오에너제닉스 | Ｐａｓｋ의 억제를 위한 복소환 화합물 |
| CN103702985B (zh) * | 2010-12-23 | 2016-02-17 | 默沙东公司 | 作为crth2受体调节剂的喹喔啉和氮杂喹喔啉 |
| JP5980812B2 (ja) * | 2011-01-05 | 2016-08-31 | バイオエナジェニックス | Ｐａｓｋの阻害のための複素環化合物 |
| US8916561B2 (en) * | 2011-03-02 | 2014-12-23 | Bioenergenix, Llc | Substituted quinoxaline compounds for the inhibition of PASK |
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- 2012-03-02 BR BR112013022147A patent/BR112013022147A2/pt not_active Application Discontinuation
- 2012-03-02 CA CA2828349A patent/CA2828349C/en active Active
- 2012-03-02 CN CN201280016906.1A patent/CN103459382B/zh not_active Expired - Fee Related
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- 2012-03-02 JP JP2013556883A patent/JP6139415B2/ja not_active Expired - Fee Related
- 2012-03-02 WO PCT/US2012/027423 patent/WO2012119046A2/en not_active Ceased
- 2012-03-02 AU AU2012223232A patent/AU2012223232B2/en not_active Ceased
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