JP2005516901A5 - - Google Patents
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- JP2005516901A5 JP2005516901A5 JP2003545655A JP2003545655A JP2005516901A5 JP 2005516901 A5 JP2005516901 A5 JP 2005516901A5 JP 2003545655 A JP2003545655 A JP 2003545655A JP 2003545655 A JP2003545655 A JP 2003545655A JP 2005516901 A5 JP2005516901 A5 JP 2005516901A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- pyrrolo
- pyridine
- carboxylic acid
- 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.)
- Pending
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- -1 hydroxy, cyano, amino Chemical group 0.000 claims 91
- 229910052736 halogen Inorganic materials 0.000 claims 75
- 150000002367 halogens Chemical class 0.000 claims 75
- 229910052739 hydrogen Inorganic materials 0.000 claims 60
- 239000001257 hydrogen Substances 0.000 claims 60
- 150000001875 compounds Chemical class 0.000 claims 53
- 150000003839 salts Chemical class 0.000 claims 42
- 150000002431 hydrogen Chemical class 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 125000006413 ring segment Chemical group 0.000 claims 32
- 125000003282 alkyl amino group Chemical group 0.000 claims 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 24
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 23
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 23
- 125000004432 carbon atom Chemical group C* 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 125000004043 oxo group Chemical group O=* 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000004076 pyridyl group Chemical group 0.000 claims 15
- 102000005962 receptors Human genes 0.000 claims 15
- 108020003175 receptors Proteins 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 14
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 14
- 125000004193 piperazinyl group Chemical group 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 11
- 238000000034 method Methods 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 239000001301 oxygen Substances 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- VFTNLQWTHUFIBV-UHFFFAOYSA-N 5-(1-methylpiperidin-4-yl)oxy-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1OC1=CC=C(NC=C2C(=O)NC=3N=CC=CC=3)C2=N1 VFTNLQWTHUFIBV-UHFFFAOYSA-N 0.000 claims 2
- 208000000044 Amnesia Diseases 0.000 claims 2
- 230000004075 alteration Effects 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 2
- 230000019491 signal transduction Effects 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- NXLQMIPOZVHJFK-UHFFFAOYSA-N 5-(1-methylazetidin-3-yl)oxy-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1N(C)CC1OC1=CC=C(NC=C2C(=O)NC3=NN(C)C=C3)C2=N1 NXLQMIPOZVHJFK-UHFFFAOYSA-N 0.000 claims 1
- ZWSJSDURDMBYLQ-UHFFFAOYSA-N 5-(1-methylpiperidin-4-yl)oxy-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1OC1=CC=C(NC=C2C(=O)NC3=NN(C)C=C3)C2=N1 ZWSJSDURDMBYLQ-UHFFFAOYSA-N 0.000 claims 1
- SXZKUSRTMZLERK-UHFFFAOYSA-N 5-(1-methylpiperidin-4-yl)oxy-n-pyridin-4-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1OC1=CC=C(NC=C2C(=O)NC=3C=CN=CC=3)C2=N1 SXZKUSRTMZLERK-UHFFFAOYSA-N 0.000 claims 1
- XDZIOWJQDMIWTP-UHFFFAOYSA-N 5-(1-methylpyrrolidin-3-yl)oxy-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1N(C)CCC1OC1=CC=C(NC=C2C(=O)NC=3N=CC=CC=3)C2=N1 XDZIOWJQDMIWTP-UHFFFAOYSA-N 0.000 claims 1
- YYWIRLPUXNJQJL-UHFFFAOYSA-N 5-(2-methoxyethoxy)-n-(3-methyl-1,2-oxazol-5-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCOC)=CC=C2NC=C1C(=O)NC1=CC(C)=NO1 YYWIRLPUXNJQJL-UHFFFAOYSA-N 0.000 claims 1
- RZXCFHINAJVRAA-UHFFFAOYSA-N 5-(2-methoxyethoxy)-n-(3-methyl-1,2-thiazol-5-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCOC)=CC=C2NC=C1C(=O)NC1=CC(C)=NS1 RZXCFHINAJVRAA-UHFFFAOYSA-N 0.000 claims 1
- BMLIEOARMJCOEO-UHFFFAOYSA-N 5-(2-methoxyethoxy)-n-(5-methyl-1,2-oxazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCOC)=CC=C2NC=C1C(=O)NC=1C=C(C)ON=1 BMLIEOARMJCOEO-UHFFFAOYSA-N 0.000 claims 1
- KRWIWZHIYZJUKQ-UHFFFAOYSA-N 5-(2-methoxyethoxy)-n-(5-methyl-1h-pyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCOC)=CC=C2NC=C1C(=O)NC=1C=C(C)NN=1 KRWIWZHIYZJUKQ-UHFFFAOYSA-N 0.000 claims 1
- WXCBYCXMAHBFQO-UHFFFAOYSA-N 5-(2-morpholin-4-ylethoxy)-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C=1NC2=CC=C(OCCN3CCOCC3)N=C2C=1C(=O)NC1=CC=CC=N1 WXCBYCXMAHBFQO-UHFFFAOYSA-N 0.000 claims 1
- VUVGOXLWIQWNHQ-UHFFFAOYSA-N 5-(3-hydroxy-3-methylbutoxy)-n-(6-methylpyridin-2-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C3=NC(OCCC(C)(C)O)=CC=C3NC=2)=N1 VUVGOXLWIQWNHQ-UHFFFAOYSA-N 0.000 claims 1
- XBNIAVQEDGQBME-UHFFFAOYSA-N 5-(3-hydroxy-3-methylbutoxy)-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCC(C)(O)C)=CC=C2NC=C1C(=O)NC1=CC=CC=N1 XBNIAVQEDGQBME-UHFFFAOYSA-N 0.000 claims 1
- CGAUNNBDSYXBOF-UHFFFAOYSA-N 5-(3-morpholin-4-ylpropoxy)-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C=1NC2=CC=C(OCCCN3CCOCC3)N=C2C=1C(=O)NC1=CC=CC=N1 CGAUNNBDSYXBOF-UHFFFAOYSA-N 0.000 claims 1
- XLJGAVFPNRWXCA-UHFFFAOYSA-N 5-(3-piperidin-1-ylpropoxy)-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C=1NC2=CC=C(OCCCN3CCCCC3)N=C2C=1C(=O)NC1=CC=CC=N1 XLJGAVFPNRWXCA-UHFFFAOYSA-N 0.000 claims 1
- QWNMDWWPDNRQMT-UHFFFAOYSA-N 5-(4-hydroxy-4-methylpentoxy)-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCC(C)(O)C)=CC=C2NC=C1C(=O)NC1=CC=CC=N1 QWNMDWWPDNRQMT-UHFFFAOYSA-N 0.000 claims 1
- KLCCIZNKKDBNDH-UHFFFAOYSA-N 5-(4-hydroxybutoxy)-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCCO)=CC=C2NC=C1C(=O)NC1=CC=CC=N1 KLCCIZNKKDBNDH-UHFFFAOYSA-N 0.000 claims 1
- QYWQLJIHKHPPFM-UHFFFAOYSA-N 5-(ethylamino)-n-(2-fluorophenyl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(NCC)=CC=C2NC=C1C(=O)NC1=CC=CC=C1F QYWQLJIHKHPPFM-UHFFFAOYSA-N 0.000 claims 1
- VPUMCDCOFJVPCI-UHFFFAOYSA-N 5-(ethylamino)-n-(4-methoxyphenyl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(NCC)=CC=C2NC=C1C(=O)NC1=CC=C(OC)C=C1 VPUMCDCOFJVPCI-UHFFFAOYSA-N 0.000 claims 1
- MTHDOPMSQCOXQE-UHFFFAOYSA-N 5-[2-(1-methylpyrrolidin-2-yl)ethoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound CN1CCCC1CCOC1=CC=C(NC=C2C(=O)NC=3N=CC=CC=3)C2=N1 MTHDOPMSQCOXQE-UHFFFAOYSA-N 0.000 claims 1
- RJSFOIHUTNRSJM-UHFFFAOYSA-N 5-[2-(4-methylpiperazin-1-yl)ethoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCOC1=CC=C(NC=C2C(=O)NC=3N=CC=CC=3)C2=N1 RJSFOIHUTNRSJM-UHFFFAOYSA-N 0.000 claims 1
- SXXRVDPSTHOEFS-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCN(CC)CC)=CC=C2NC=C1C(=O)NC=1C=CN(C)N=1 SXXRVDPSTHOEFS-UHFFFAOYSA-N 0.000 claims 1
- QQDABHSXACUVLG-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-n-(5-methyl-1,2-oxazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCN(CC)CC)=CC=C2NC=C1C(=O)NC=1C=C(C)ON=1 QQDABHSXACUVLG-UHFFFAOYSA-N 0.000 claims 1
- PEKRKGMBPFWCHH-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCN(CC)CC)=CC=C2NC=C1C(=O)NC1=CC=CC=N1 PEKRKGMBPFWCHH-UHFFFAOYSA-N 0.000 claims 1
- WJSRBXHTAJNOTA-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCN(C)C)=CC=C2NC=C1C(=O)NC=1C=CN(C)N=1 WJSRBXHTAJNOTA-UHFFFAOYSA-N 0.000 claims 1
- YHQZXVDLTYWIJU-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-(5-methyl-1,2-oxazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCN(C)C)=CC=C2NC=C1C(=O)NC=1C=C(C)ON=1 YHQZXVDLTYWIJU-UHFFFAOYSA-N 0.000 claims 1
- XYTNNYDOEDDGHU-UHFFFAOYSA-N 5-[2-(dimethylamino)ethoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCN(C)C)=CC=C2NC=C1C(=O)NC1=CC=CC=N1 XYTNNYDOEDDGHU-UHFFFAOYSA-N 0.000 claims 1
- ZDHMOJZRSYHGDD-UHFFFAOYSA-N 5-[3-(3-methylpiperidin-1-yl)propoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1C(C)CCCN1CCCOC1=CC=C(NC=C2C(=O)NC=3N=CC=CC=3)C2=N1 ZDHMOJZRSYHGDD-UHFFFAOYSA-N 0.000 claims 1
- CDEYRBWJRBNEJH-UHFFFAOYSA-N 5-[3-(4-methylpiperazin-1-yl)propoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCCOC1=CC=C(NC=C2C(=O)NC=3N=CC=CC=3)C2=N1 CDEYRBWJRBNEJH-UHFFFAOYSA-N 0.000 claims 1
- CFRBGXIYDHGZDS-UHFFFAOYSA-N 5-[3-(6-azabicyclo[3.2.2]nonan-6-yl)propoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound CN1C=CC(NC(=O)C=2C3=NC(OCCCN4C5CCC(CCC5)C4)=CC=C3NC=2)=N1 CFRBGXIYDHGZDS-UHFFFAOYSA-N 0.000 claims 1
- OIGVLUJBEKOPJM-UHFFFAOYSA-N 5-[3-(azetidin-1-yl)propoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound CN1C=CC(NC(=O)C=2C3=NC(OCCCN4CCC4)=CC=C3NC=2)=N1 OIGVLUJBEKOPJM-UHFFFAOYSA-N 0.000 claims 1
- YBTBULAXKLJUJR-UHFFFAOYSA-N 5-[3-(azetidin-1-yl)propoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C=1NC2=CC=C(OCCCN3CCC3)N=C2C=1C(=O)NC1=CC=CC=N1 YBTBULAXKLJUJR-UHFFFAOYSA-N 0.000 claims 1
- XLPLXNHFVDKLJQ-UHFFFAOYSA-N 5-[3-(diethylamino)propoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(CC)CC)=CC=C2NC=C1C(=O)NC=1C=CN(C)N=1 XLPLXNHFVDKLJQ-UHFFFAOYSA-N 0.000 claims 1
- LEWAYLXZGYPICP-UHFFFAOYSA-N 5-[3-(diethylamino)propoxy]-n-(6-ethylpyridin-2-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(CC)CC)=CC=C2NC=C1C(=O)NC1=CC=CC(CC)=N1 LEWAYLXZGYPICP-UHFFFAOYSA-N 0.000 claims 1
- WOSJATPBFFCUDR-UHFFFAOYSA-N 5-[3-(diethylamino)propoxy]-n-(6-methylpyridin-2-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(CC)CC)=CC=C2NC=C1C(=O)NC1=CC=CC(C)=N1 WOSJATPBFFCUDR-UHFFFAOYSA-N 0.000 claims 1
- SGISFWBOMVPOHY-UHFFFAOYSA-N 5-[3-(diethylamino)propoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(CC)CC)=CC=C2NC=C1C(=O)NC1=CC=CC=N1 SGISFWBOMVPOHY-UHFFFAOYSA-N 0.000 claims 1
- TWVMFAJFXQWSNZ-UHFFFAOYSA-N 5-[3-(dimethylamino)-2,2-dimethylpropoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCC(C)(C)CN(C)C)=CC=C2NC=C1C(=O)NC=1C=CN(C)N=1 TWVMFAJFXQWSNZ-UHFFFAOYSA-N 0.000 claims 1
- OPXNVNATDUCALK-UHFFFAOYSA-N 5-[3-(dimethylamino)-2,2-dimethylpropoxy]-n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCC(C)(C)CN(C)C)=CC=C2NC=C1C(=O)NC1=CC=CC=N1 OPXNVNATDUCALK-UHFFFAOYSA-N 0.000 claims 1
- CLUOOJXTIAQZKW-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]-n-(1-ethylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound CCN1C=CC(NC(=O)C=2C3=NC(OCCCN(C)C)=CC=C3NC=2)=N1 CLUOOJXTIAQZKW-UHFFFAOYSA-N 0.000 claims 1
- RDTZVCJWAYWZGO-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(C)C)=CC=C2NC=C1C(=O)NC=1C=CN(C)N=1 RDTZVCJWAYWZGO-UHFFFAOYSA-N 0.000 claims 1
- PACOXFCRZJTDCR-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]-n-(1-propylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound CCCN1C=CC(NC(=O)C=2C3=NC(OCCCN(C)C)=CC=C3NC=2)=N1 PACOXFCRZJTDCR-UHFFFAOYSA-N 0.000 claims 1
- GNPZSHUHJJOKPR-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]-n-(3-fluorophenyl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(C)C)=CC=C2NC=C1C(=O)NC1=CC=CC(F)=C1 GNPZSHUHJJOKPR-UHFFFAOYSA-N 0.000 claims 1
- CLGMAPDJGUGBAN-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]-n-(3-methyl-1,2-oxazol-5-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(C)C)=CC=C2NC=C1C(=O)NC1=CC(C)=NO1 CLGMAPDJGUGBAN-UHFFFAOYSA-N 0.000 claims 1
- SRSHRDDBRASUQK-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]-n-(4,6-dimethylpyridin-2-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(C)C)=CC=C2NC=C1C(=O)NC1=CC(C)=CC(C)=N1 SRSHRDDBRASUQK-UHFFFAOYSA-N 0.000 claims 1
- PBGGNZOJHZGKSI-UHFFFAOYSA-N 5-[3-(dimethylamino)propoxy]-n-(5-methyl-1,3,4-thiadiazol-2-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCCCN(C)C)=CC=C2NC=C1C(=O)NC1=NN=C(C)S1 PBGGNZOJHZGKSI-UHFFFAOYSA-N 0.000 claims 1
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- JEQBUHDIELBLHJ-UHFFFAOYSA-N n-(6-methoxypyrazin-2-yl)-5-(1-methylpiperidin-4-yl)oxy-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound COC1=CN=CC(NC(=O)C=2C3=NC(OC4CCN(C)CC4)=CC=C3NC=2)=N1 JEQBUHDIELBLHJ-UHFFFAOYSA-N 0.000 claims 1
- VRULZWPRUHOAPF-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethyl]phenyl]-5-ethoxy-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCC)=CC=C2NC=C1C(=O)NC1=CC=C(CCN(CC)CC)C=C1 VRULZWPRUHOAPF-UHFFFAOYSA-N 0.000 claims 1
- OWBKWZGQIBWMSS-UHFFFAOYSA-N n-[4-[3-(methanesulfonamido)propoxy]phenyl]-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1=CC(OCCCNS(=O)(=O)C)=CC=C1NC(=O)C1=CNC2=CC=CN=C12 OWBKWZGQIBWMSS-UHFFFAOYSA-N 0.000 claims 1
- VIEJWJLVFAMLTQ-UHFFFAOYSA-N n-[6-[3-(diethylamino)propoxy]pyridin-3-yl]-5-ethoxy-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCC)=CC=C2NC=C1C(=O)NC1=CC=C(OCCCN(CC)CC)N=C1 VIEJWJLVFAMLTQ-UHFFFAOYSA-N 0.000 claims 1
- OQZFULXWBKRMFK-UHFFFAOYSA-N n-[6-[3-(diethylamino)propoxy]pyridin-3-yl]-5-methoxy-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1=NC(OCCCN(CC)CC)=CC=C1NC(=O)C1=CNC2=CC=C(OC)N=C12 OQZFULXWBKRMFK-UHFFFAOYSA-N 0.000 claims 1
- RURXSDZKKASHSF-UHFFFAOYSA-N n-pyridin-2-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C=1NC2=CC=CN=C2C=1C(=O)NC1=CC=CC=N1 RURXSDZKKASHSF-UHFFFAOYSA-N 0.000 claims 1
- NFOMGXHFYLAQLO-UHFFFAOYSA-N n-pyridin-2-yl-5-(2-pyrrolidin-1-ylethoxy)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C=1NC2=CC=C(OCCN3CCCC3)N=C2C=1C(=O)NC1=CC=CC=N1 NFOMGXHFYLAQLO-UHFFFAOYSA-N 0.000 claims 1
- WOPNAAFEBYTKSQ-UHFFFAOYSA-N n-pyridin-2-yl-5-(3-pyridin-2-ylpropoxy)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C=1NC2=CC=C(OCCCC=3N=CC=CC=3)N=C2C=1C(=O)NC1=CC=CC=N1 WOPNAAFEBYTKSQ-UHFFFAOYSA-N 0.000 claims 1
- ABXKXRBQKXGMNS-UHFFFAOYSA-N n-pyridin-2-yl-5-(3-pyrrol-1-ylpropoxy)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C=1NC2=CC=C(OCCCN3C=CC=C3)N=C2C=1C(=O)NC1=CC=CC=N1 ABXKXRBQKXGMNS-UHFFFAOYSA-N 0.000 claims 1
- QZNPXKRALPFXPR-UHFFFAOYSA-N n-pyridin-2-ylpyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC1=CC=CC=N1 QZNPXKRALPFXPR-UHFFFAOYSA-N 0.000 claims 1
- WTTQCJZUJSVBJX-UHFFFAOYSA-N n-quinolin-8-yl-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1=CN=C2C(C(NC=3C4=NC=CC=C4C=CC=3)=O)=CNC2=C1 WTTQCJZUJSVBJX-UHFFFAOYSA-N 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 230000006403 short-term memory Effects 0.000 claims 1
- 230000007781 signaling event Effects 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33302701P | 2001-11-19 | 2001-11-19 | |
| PCT/US2002/037157 WO2003044018A1 (en) | 2001-11-19 | 2002-11-19 | 1h-pyrrolo[3,2-b]pyridine-3-carboxylic acid amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005516901A JP2005516901A (ja) | 2005-06-09 |
| JP2005516901A5 true JP2005516901A5 (enExample) | 2006-01-19 |
Family
ID=23300941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003545655A Pending JP2005516901A (ja) | 2001-11-19 | 2002-11-19 | １Ｈ−ピロロ［３，２−ｂ］ピリジン−３−カルボン酸アミド化合物 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1453831A1 (enExample) |
| JP (1) | JP2005516901A (enExample) |
| AU (1) | AU2002366092A1 (enExample) |
| BR (1) | BR0214301A (enExample) |
| CA (1) | CA2467542A1 (enExample) |
| MX (1) | MXPA04004711A (enExample) |
| WO (1) | WO2003044018A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2865208B1 (fr) * | 2004-01-16 | 2009-01-16 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo[3.2.1]octanecarboxmique, leur preparation et leur application en therapeutique |
| FR2890072A1 (fr) * | 2005-09-01 | 2007-03-02 | Fournier S A Sa Lab | Nouveaux composesde pyrrolopyridine |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| WO2014196793A1 (en) | 2013-06-05 | 2014-12-11 | C&C Research Laboratories | Heterocyclic derivatives and use thereof |
| GB201317363D0 (en) | 2013-10-01 | 2013-11-13 | Eisai Ltd | Novel compounds |
| CN116102549B (zh) * | 2021-11-09 | 2025-02-11 | 暨南大学 | 5-醛基杂环酰胺类化合物及其应用 |
| WO2023082044A1 (zh) * | 2021-11-09 | 2023-05-19 | 暨南大学 | 5-醛基杂环酰胺类化合物及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750702A (en) * | 1993-10-27 | 1998-05-12 | Neurogen Corporation | Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain receptor ligands |
-
2002
- 2002-11-19 JP JP2003545655A patent/JP2005516901A/ja active Pending
- 2002-11-19 CA CA002467542A patent/CA2467542A1/en not_active Abandoned
- 2002-11-19 AU AU2002366092A patent/AU2002366092A1/en not_active Abandoned
- 2002-11-19 MX MXPA04004711A patent/MXPA04004711A/es active IP Right Grant
- 2002-11-19 WO PCT/US2002/037157 patent/WO2003044018A1/en not_active Ceased
- 2002-11-19 EP EP02803679A patent/EP1453831A1/en not_active Withdrawn
- 2002-11-19 BR BR0214301-1A patent/BR0214301A/pt not_active IP Right Cessation
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