MXPA04004711A - Amidas del acido 1h-pirrolo(3,2-b(piridin-3-carboxilico. - Google Patents
Amidas del acido 1h-pirrolo(3,2-b(piridin-3-carboxilico.Info
- Publication number
- MXPA04004711A MXPA04004711A MXPA04004711A MXPA04004711A MXPA04004711A MX PA04004711 A MXPA04004711 A MX PA04004711A MX PA04004711 A MXPA04004711 A MX PA04004711A MX PA04004711 A MXPA04004711 A MX PA04004711A MX PA04004711 A MXPA04004711 A MX PA04004711A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- alkoxy
- pyrrolo
- carboxylic acid
- pyridin
- Prior art date
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 169
- 102000027484 GABAA receptors Human genes 0.000 claims abstract description 50
- 108091008681 GABAA receptors Proteins 0.000 claims abstract description 50
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 238000000338 in vitro Methods 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 209
- 125000003545 alkoxy group Chemical group 0.000 claims description 190
- -1 cyano, amino Chemical group 0.000 claims description 181
- 229910052736 halogen Inorganic materials 0.000 claims description 84
- 150000002367 halogens Chemical class 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 77
- 125000003282 alkyl amino group Chemical group 0.000 claims description 67
- 150000003839 salts Chemical class 0.000 claims description 61
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 38
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000004076 pyridyl group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 30
- 125000004193 piperazinyl group Chemical group 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000006413 ring segment Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 125000004043 oxo group Chemical group O=* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 102000005962 receptors Human genes 0.000 claims description 18
- 108020003175 receptors Proteins 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 235000001968 nicotinic acid Nutrition 0.000 claims description 14
- 239000011664 nicotinic acid Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 9
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 9
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 230000002463 transducing effect Effects 0.000 claims description 5
- VAQUJLYRUQNSEV-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-3-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CNC2=C1 VAQUJLYRUQNSEV-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 230000004075 alteration Effects 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 4
- 230000007831 electrophysiology Effects 0.000 claims description 4
- 238000002001 electrophysiology Methods 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 238000000159 protein binding assay Methods 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 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
- 125000004196 benzothienyl group Chemical group S1C(=CC2=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
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 3
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 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
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 230000019491 signal transduction Effects 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 238000000376 autoradiography Methods 0.000 claims description 2
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005995 isobenzotetrahydrothienyl group Chemical group 0.000 claims description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005412 pyrazyl group Chemical group 0.000 claims description 2
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 7
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 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 4
- 150000001204 N-oxides Chemical class 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- MOGQNVSKBCVIPW-UHFFFAOYSA-N 1-methylpyrazol-3-amine Chemical compound CN1C=CC(N)=N1 MOGQNVSKBCVIPW-UHFFFAOYSA-N 0.000 claims 3
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000006319 alkynyl amino group Chemical group 0.000 claims 2
- 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 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- OPFNZHIUHJBGEW-UHFFFAOYSA-N 1-hydroxyimidazole Chemical compound ON1C=CN=C1 OPFNZHIUHJBGEW-UHFFFAOYSA-N 0.000 claims 1
- LONOODCVABUHFO-UHFFFAOYSA-N 1-propylpyrazol-3-amine Chemical compound CCCN1C=CC(N)=N1 LONOODCVABUHFO-UHFFFAOYSA-N 0.000 claims 1
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 claims 1
- FNXYWHTZDAVRTB-UHFFFAOYSA-N 3-methyl-1,2-oxazol-5-amine Chemical compound CC=1C=C(N)ON=1 FNXYWHTZDAVRTB-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
- 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
- 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
- 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
- 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
- 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
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 claims 1
- LOKQCAQHPJAORD-UHFFFAOYSA-N 5-ethoxy-n-[3-(hydroxymethyl)phenyl]-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCC)=CC=C2NC=C1C(=O)NC1=CC=CC(CO)=C1 LOKQCAQHPJAORD-UHFFFAOYSA-N 0.000 claims 1
- ABSHGTKCNSLCGZ-UHFFFAOYSA-N 5-methoxy-1h-pyrrolo[3,2-b]pyridine-3-carboxylic acid Chemical compound COC1=CC=C2NC=C(C(O)=O)C2=N1 ABSHGTKCNSLCGZ-UHFFFAOYSA-N 0.000 claims 1
- VAXZDWVWPDAOOA-UHFFFAOYSA-N 5-methoxy-n-(4-methoxyphenyl)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CNC2=CC=C(OC)N=C12 VAXZDWVWPDAOOA-UHFFFAOYSA-N 0.000 claims 1
- FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 claims 1
- YFFHQSIIVNBIGD-UHFFFAOYSA-N 5-propoxypyridin-2-amine Chemical compound CCCOC1=CC=C(N)N=C1 YFFHQSIIVNBIGD-UHFFFAOYSA-N 0.000 claims 1
- 235000021513 Cinchona Nutrition 0.000 claims 1
- 241000157855 Cinchona Species 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- 101150079116 MT-CO1 gene Proteins 0.000 claims 1
- HCXNYCOVQIVDCW-UHFFFAOYSA-N N-(3-methyl-1,2-thiazol-5-yl)pyridine-3-carboxamide Chemical compound S1N=C(C)C=C1NC(=O)C1=CC=CN=C1 HCXNYCOVQIVDCW-UHFFFAOYSA-N 0.000 claims 1
- OKLZSCXLCKQRAU-UHFFFAOYSA-N N-[4-[3-(methanesulfonamido)propoxy]phenyl]pyridine-3-carboxamide Chemical compound CS(=O)(=O)NCCCOC1=CC=C(C=C1)NC(=O)C=1C=NC=CC=1 OKLZSCXLCKQRAU-UHFFFAOYSA-N 0.000 claims 1
- 235000013400 Quercus lobata Nutrition 0.000 claims 1
- 240000001749 Quercus lobata Species 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- RBPYMCCOFULESL-UHFFFAOYSA-N n-(1-methylpyrazol-3-yl)-5-(3-morpholin-4-ylpropoxy)-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound CN1C=CC(NC(=O)C=2C3=NC(OCCCN4CCOCC4)=CC=C3NC=2)=N1 RBPYMCCOFULESL-UHFFFAOYSA-N 0.000 claims 1
- VZOQCGLPGIOKHU-UHFFFAOYSA-N n-(2-fluorophenyl)-5-methoxy-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OC)=CC=C2NC=C1C(=O)NC1=CC=CC=C1F VZOQCGLPGIOKHU-UHFFFAOYSA-N 0.000 claims 1
- NFDGKRRKIIFBAB-UHFFFAOYSA-N n-(2-fluorophenyl)pyridine-3-carboxamide Chemical compound FC1=CC=CC=C1NC(=O)C1=CC=CN=C1 NFDGKRRKIIFBAB-UHFFFAOYSA-N 0.000 claims 1
- QPXBTYCQIUDAAZ-UHFFFAOYSA-N n-(6-bromopyridin-3-yl)-5-ethoxy-1h-pyrrolo[3,2-b]pyridine-3-carboxamide Chemical compound C12=NC(OCC)=CC=C2NC=C1C(=O)NC1=CC=C(Br)N=C1 QPXBTYCQIUDAAZ-UHFFFAOYSA-N 0.000 claims 1
- CXOYCQYEVSXBNT-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)pyridine-3-carboxamide Chemical compound C1=NC(OC)=CC=C1NC(=O)C1=CC=CN=C1 CXOYCQYEVSXBNT-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
- 239000006187 pill Substances 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 18
- 229940049706 benzodiazepine Drugs 0.000 abstract description 16
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 abstract description 13
- 241001465754 Metazoa Species 0.000 abstract description 10
- 210000003169 central nervous system Anatomy 0.000 abstract description 8
- 238000001727 in vivo Methods 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 4
- 244000144972 livestock Species 0.000 abstract description 2
- 150000002431 hydrogen Chemical group 0.000 description 32
- 239000000203 mixture Substances 0.000 description 23
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 22
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 20
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
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Classifications
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
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- 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
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- 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 (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 (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04004711A true MXPA04004711A (es) | 2005-08-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04004711A MXPA04004711A (es) | 2001-11-19 | 2002-11-19 | Amidas del acido 1h-pirrolo(3,2-b(piridin-3-carboxilico. |
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) |
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| 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 |
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-
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 |
| AU2002366092A1 (en) | 2003-06-10 |
| CA2467542A1 (en) | 2003-05-30 |
| BR0214301A (pt) | 2004-10-13 |
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| FG | Grant or registration |