CA2467542A1 - 1h-pyrrolo[3,2-b]pyridine-3-carboxylic acid amides - Google Patents
1h-pyrrolo[3,2-b]pyridine-3-carboxylic acid amides Download PDFInfo
- Publication number
- CA2467542A1 CA2467542A1 CA002467542A CA2467542A CA2467542A1 CA 2467542 A1 CA2467542 A1 CA 2467542A1 CA 002467542 A CA002467542 A CA 002467542A CA 2467542 A CA2467542 A CA 2467542A CA 2467542 A1 CA2467542 A1 CA 2467542A1
- Authority
- CA
- Canada
- Prior art keywords
- c6alkyl
- 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.)
- Abandoned
Links
- PMBKVWCLVTYNAG-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical class C1=CN=C2C(C(=O)N)=CNC2=C1 PMBKVWCLVTYNAG-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 241
- 230000027455 binding Effects 0.000 claims abstract description 21
- 238000000338 in vitro Methods 0.000 claims abstract description 10
- -1 hydroxy, cyano, amino Chemical group 0.000 claims description 224
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 143
- 229910052736 halogen Inorganic materials 0.000 claims description 138
- 150000002367 halogens Chemical class 0.000 claims description 137
- 229910052739 hydrogen Inorganic materials 0.000 claims description 120
- 239000001257 hydrogen Substances 0.000 claims description 119
- 150000003839 salts Chemical class 0.000 claims description 88
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 73
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 60
- 125000006413 ring segment Chemical group 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 125000004043 oxo group Chemical group O=* 0.000 claims description 42
- 125000004076 pyridyl group Chemical group 0.000 claims description 41
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 40
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 39
- 125000003282 alkyl amino group Chemical group 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- 125000004193 piperazinyl group Chemical group 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 230000000694 effects Effects 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 102000005962 receptors Human genes 0.000 claims description 22
- 108020003175 receptors Proteins 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 241000282414 Homo sapiens Species 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 208000019901 Anxiety disease Diseases 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 230000036506 anxiety Effects 0.000 claims description 11
- 208000019116 sleep disease Diseases 0.000 claims description 11
- 238000003556 assay Methods 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 7
- 230000007831 electrophysiology Effects 0.000 claims description 7
- 238000002001 electrophysiology Methods 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 6
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 6
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 6
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 230000004075 alteration Effects 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 230000003389 potentiating effect Effects 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 208000020685 sleep-wake disease Diseases 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- 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 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000000376 autoradiography Methods 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005992 dihydrobenzisothiazinyl group Chemical group 0.000 claims description 3
- 125000005993 dihydrobenzisoxazinyl group Chemical group 0.000 claims description 3
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
- 125000005994 isobenzotetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000005995 isobenzotetrahydrothienyl group Chemical group 0.000 claims description 3
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 3
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003151 isocoumarinyl group Chemical group C1(=O)OC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 2
- 230000003834 intracellular effect Effects 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 230000006403 short-term memory Effects 0.000 claims description 2
- 102000004300 GABA-A Receptors Human genes 0.000 claims 14
- 108090000839 GABA-A Receptors Proteins 0.000 claims 14
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- FJRVIIDXTLOOFA-UHFFFAOYSA-N 5-ethoxy-1h-pyrrolo[3,2-b]pyridine-3-carboxylic acid Chemical compound CCOC1=CC=C2NC=C(C(O)=O)C2=N1 FJRVIIDXTLOOFA-UHFFFAOYSA-N 0.000 claims 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 208000000044 Amnesia Diseases 0.000 claims 2
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 2
- 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
- MXEUOZMPNWVBMS-UHFFFAOYSA-N 5-[2-(4-methylpiperazin-1-yl)ethoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCOC1=CC=C(NC=C2C(=O)NC3=NN(C)C=C3)C2=N1 MXEUOZMPNWVBMS-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
- QCXVLAUQHHKNRU-UHFFFAOYSA-N 5-[3-(3-methylpiperidin-1-yl)propoxy]-n-(1-methylpyrazol-3-yl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1C(C)CCCN1CCCOC1=CC=C(NC=C2C(=O)NC3=NN(C)C=C3)C2=N1 QCXVLAUQHHKNRU-UHFFFAOYSA-N 0.000 claims 1
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- PAOSNMHABBSWFH-UHFFFAOYSA-N ethyl 5-(1-methylpiperidin-4-yl)oxy-1h-pyrrolo[3,2-b]pyridine-3-carboxylate Chemical compound N1=C2C(C(=O)OCC)=CNC2=CC=C1OC1CCN(C)CC1 PAOSNMHABBSWFH-UHFFFAOYSA-N 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 239000010502 orange oil Substances 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
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- 239000000312 peanut oil Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33302701P | 2001-11-19 | 2001-11-19 | |
| US60/333,027 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2467542A1 true CA2467542A1 (en) | 2003-05-30 |
Family
ID=23300941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002467542A Abandoned CA2467542A1 (en) | 2001-11-19 | 2002-11-19 | 1h-pyrrolo[3,2-b]pyridine-3-carboxylic acid amides |
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
Also Published As
| Publication number | Publication date |
|---|---|
| EP1453831A1 (en) | 2004-09-08 |
| JP2005516901A (ja) | 2005-06-09 |
| WO2003044018A1 (en) | 2003-05-30 |
| MXPA04004711A (es) | 2005-08-16 |
| AU2002366092A1 (en) | 2003-06-10 |
| BR0214301A (pt) | 2004-10-13 |
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Effective date: 20111121 |