HRP970385A2 - Certain fused pyrrolecarboxanilides; new class of gaba brain receptor ligands - Google Patents
Certain fused pyrrolecarboxanilides; new class of gaba brain receptor ligandsInfo
- Publication number
- HRP970385A2 HRP970385A2 HR08/683,066A HRP970385A HRP970385A2 HR P970385 A2 HRP970385 A2 HR P970385A2 HR P970385 A HRP970385 A HR P970385A HR P970385 A2 HRP970385 A2 HR P970385A2
- Authority
- HR
- Croatia
- Prior art keywords
- oxo
- carboxamide
- compound according
- alkyl
- chemical composition
- Prior art date
Links
- 210000004556 brain Anatomy 0.000 title description 11
- 239000003446 ligand Substances 0.000 title description 4
- MZPAQCAPWLAKSD-UHFFFAOYSA-N n-phenyl-1h-pyrrole-2-carboxamide Chemical class C=1C=CNC=1C(=O)NC1=CC=CC=C1 MZPAQCAPWLAKSD-UHFFFAOYSA-N 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 266
- 150000001875 compounds Chemical class 0.000 claims description 248
- 229910052739 hydrogen Inorganic materials 0.000 claims description 170
- 239000001257 hydrogen Chemical group 0.000 claims description 169
- 239000000203 mixture Substances 0.000 claims description 146
- 125000004432 carbon atom Chemical group C* 0.000 claims description 104
- 239000000126 substance Substances 0.000 claims description 95
- 229910052736 halogen Inorganic materials 0.000 claims description 68
- 150000002367 halogens Chemical group 0.000 claims description 67
- 125000003545 alkoxy group Chemical group 0.000 claims description 65
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- -1 hydroxy, nitro, amino Chemical group 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 39
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 31
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 27
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 27
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 27
- 231100000252 nontoxic Toxicity 0.000 claims description 25
- 230000003000 nontoxic effect Effects 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 21
- 101150047265 COR2 gene Proteins 0.000 claims description 15
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- PYYASPIHGYQLMC-UHFFFAOYSA-N 4-oxo-n-phenyl-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C=1NC=2CCCCC(=O)C=2C=1C(=O)NC1=CC=CC=C1 PYYASPIHGYQLMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- QCIKGTZGMLOQJD-UHFFFAOYSA-N n-(4-aminophenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 QCIKGTZGMLOQJD-UHFFFAOYSA-N 0.000 claims description 5
- BXWHPWMVTGDJJE-UHFFFAOYSA-N n-(4-ethoxyphenyl)-1-ethyl-4-oxo-6,7-dihydro-5h-indole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=CN(CC)C2=C1C(=O)CCC2 BXWHPWMVTGDJJE-UHFFFAOYSA-N 0.000 claims description 5
- XKIKAQMXQDSBFA-UHFFFAOYSA-N n-(4-fluorophenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 XKIKAQMXQDSBFA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- ZYTPCURSRRABAJ-UHFFFAOYSA-N n-(2-fluoro-4-hydroxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC(O)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 ZYTPCURSRRABAJ-UHFFFAOYSA-N 0.000 claims description 4
- OVIGGAOMLUKHDD-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 OVIGGAOMLUKHDD-UHFFFAOYSA-N 0.000 claims description 4
- ATTJYGQSUFHDFY-UHFFFAOYSA-N n-(2-fluoro-4-propan-2-yloxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC(OC(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 ATTJYGQSUFHDFY-UHFFFAOYSA-N 0.000 claims description 4
- MMRVYNWTXWYLEG-UHFFFAOYSA-N n-(3-ethoxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CCOC1=CC=CC(NC(=O)C=2C=3C(=O)CCCC=3NC=2)=C1 MMRVYNWTXWYLEG-UHFFFAOYSA-N 0.000 claims description 4
- NECIWLPHAXVOCU-UHFFFAOYSA-N n-(3-hydroxy-4-methoxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=C(O)C(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 NECIWLPHAXVOCU-UHFFFAOYSA-N 0.000 claims description 4
- UFSXEIXYYXGTEN-UHFFFAOYSA-N n-(3-methylphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C=3C(=O)CCCC=3NC=2)=C1 UFSXEIXYYXGTEN-UHFFFAOYSA-N 0.000 claims description 4
- CKIGCFHTDPSXFO-UHFFFAOYSA-N n-(4-ethoxy-2-fluorophenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound FC1=CC(OCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 CKIGCFHTDPSXFO-UHFFFAOYSA-N 0.000 claims description 4
- YIUQVWKFROAFAO-UHFFFAOYSA-N n-(4-ethoxyphenyl)-2-nitro-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=C([N+]([O-])=O)NC2=C1C(=O)CCC2 YIUQVWKFROAFAO-UHFFFAOYSA-N 0.000 claims description 4
- OFPARKKFNMCLNK-UHFFFAOYSA-N n-(4-ethoxyphenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 OFPARKKFNMCLNK-UHFFFAOYSA-N 0.000 claims description 4
- SQWZFXDHMUUZAM-UHFFFAOYSA-N n-(4-ethoxyphenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)C(C)(C)CC2 SQWZFXDHMUUZAM-UHFFFAOYSA-N 0.000 claims description 4
- GPAQDOTXIMCEMU-UHFFFAOYSA-N n-(4-fluorophenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 GPAQDOTXIMCEMU-UHFFFAOYSA-N 0.000 claims description 4
- QCWFEVMJQPXTBG-UHFFFAOYSA-N n-(4-fluorophenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=2C(=O)C(C)(C)CCC=2NC=C1C(=O)NC1=CC=C(F)C=C1 QCWFEVMJQPXTBG-UHFFFAOYSA-N 0.000 claims description 4
- YKWHXFSLAYIBQP-UHFFFAOYSA-N n-(4-hydroxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 YKWHXFSLAYIBQP-UHFFFAOYSA-N 0.000 claims description 4
- SBECLSXPLXGYPN-UHFFFAOYSA-N n-(4-methoxyphenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)C(C)(C)CC2 SBECLSXPLXGYPN-UHFFFAOYSA-N 0.000 claims description 4
- VKXRVCMFPRMSFX-UHFFFAOYSA-N n-(4-methylphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 VKXRVCMFPRMSFX-UHFFFAOYSA-N 0.000 claims description 4
- HYPYSFKXCLPAEJ-UHFFFAOYSA-N 4-oxo-n-phenyl-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CC=CC=C1 HYPYSFKXCLPAEJ-UHFFFAOYSA-N 0.000 claims description 3
- SIEGEZAGLWXLLC-UHFFFAOYSA-N 5,5-dimethyl-4-oxo-n-phenyl-6,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=2C(=O)C(C)(C)CCC=2NC=C1C(=O)NC1=CC=CC=C1 SIEGEZAGLWXLLC-UHFFFAOYSA-N 0.000 claims description 3
- YHUGZXJXRSRRTQ-UHFFFAOYSA-N 5,5-dimethyl-n-(3-methylphenyl)-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C=3C(=O)C(C)(C)CCC=3NC=2)=C1 YHUGZXJXRSRRTQ-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- PSDGJVYISKVNLI-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-4-phenylmethoxy-1h-indole-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=CNC2=CC=CC(OCC=3C=CC=CC=3)=C12 PSDGJVYISKVNLI-UHFFFAOYSA-N 0.000 claims description 3
- NABNRZXEDLVUIR-UHFFFAOYSA-N n-(2-fluoro-4-methylphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC(C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 NABNRZXEDLVUIR-UHFFFAOYSA-N 0.000 claims description 3
- RHCNIHOJZNUULS-UHFFFAOYSA-N n-(2-fluoro-5-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound COC1=CC=C(F)C(NC(=O)C=2C=3C(=O)CCCCC=3NC=2)=C1 RHCNIHOJZNUULS-UHFFFAOYSA-N 0.000 claims description 3
- GLDKKPMUZAOPPP-UHFFFAOYSA-N n-(2-fluorophenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 GLDKKPMUZAOPPP-UHFFFAOYSA-N 0.000 claims description 3
- LUOSTKNZGHERTG-UHFFFAOYSA-N n-(2-fluorophenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound FC1=CC=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 LUOSTKNZGHERTG-UHFFFAOYSA-N 0.000 claims description 3
- PLYSTZXCBKMGDD-UHFFFAOYSA-N n-(2-fluorophenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=2C(=O)C(C)(C)CCC=2NC=C1C(=O)NC1=CC=CC=C1F PLYSTZXCBKMGDD-UHFFFAOYSA-N 0.000 claims description 3
- FBNCYYCWVRBXLV-UHFFFAOYSA-N n-(3,4-dihydroxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=C(O)C(O)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 FBNCYYCWVRBXLV-UHFFFAOYSA-N 0.000 claims description 3
- VGQWVRUTLWYVDA-UHFFFAOYSA-N n-(3-fluorophenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound FC1=CC=CC(NC(=O)C=2C=3C(=O)CCCCC=3NC=2)=C1 VGQWVRUTLWYVDA-UHFFFAOYSA-N 0.000 claims description 3
- OOFZMLCXRPIXKS-UHFFFAOYSA-N n-(4-ethoxyphenyl)-2-methyl-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=C(C)NC2=C1C(=O)CCC2 OOFZMLCXRPIXKS-UHFFFAOYSA-N 0.000 claims description 3
- PBYJTTXYNCBECW-UHFFFAOYSA-N n-(4-fluoro-2-hydroxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound OC1=CC(F)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 PBYJTTXYNCBECW-UHFFFAOYSA-N 0.000 claims description 3
- QWZRQJOPLWQECM-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 QWZRQJOPLWQECM-UHFFFAOYSA-N 0.000 claims description 3
- NDHHUMAKIMJJPO-UHFFFAOYSA-N n-[4-(methylamino)phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(NC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 NDHHUMAKIMJJPO-UHFFFAOYSA-N 0.000 claims description 3
- OHISDDTWMUUIHW-UHFFFAOYSA-N 2-amino-n-(4-ethoxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=C(N)NC2=C1C(=O)CCC2 OHISDDTWMUUIHW-UHFFFAOYSA-N 0.000 claims description 2
- HBTSPXINGOJCIL-UHFFFAOYSA-N 2-bromo-n-(4-ethoxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=C(Br)NC2=C1C(=O)CCC2 HBTSPXINGOJCIL-UHFFFAOYSA-N 0.000 claims description 2
- LEFPXGYOTXQNRW-UHFFFAOYSA-N 2-chloro-n-(4-ethoxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=C(Cl)NC2=C1C(=O)CCC2 LEFPXGYOTXQNRW-UHFFFAOYSA-N 0.000 claims description 2
- BQCVEIMUGKYFPO-UHFFFAOYSA-N 4-oxo-n-(4-propan-2-yloxyphenyl)-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 BQCVEIMUGKYFPO-UHFFFAOYSA-N 0.000 claims description 2
- FVBJBRFZBVRNGR-UHFFFAOYSA-N 6,6-dimethyl-4-oxo-n-phenyl-5,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=2C(=O)CC(C)(C)CC=2NC=C1C(=O)NC1=CC=CC=C1 FVBJBRFZBVRNGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- WFNYOGNEPRNLLP-UHFFFAOYSA-N n-(2-amino-4-methylphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound NC1=CC(C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 WFNYOGNEPRNLLP-UHFFFAOYSA-N 0.000 claims description 2
- AHEVCVRSGULLIW-UHFFFAOYSA-N n-(2-fluoro-4-hydroxyphenyl)-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound FC1=CC(O)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 AHEVCVRSGULLIW-UHFFFAOYSA-N 0.000 claims description 2
- QBZQDEQDWGLWON-UHFFFAOYSA-N n-(2-fluoro-4-hydroxyphenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=2C(=O)C(C)(C)CCC=2NC=C1C(=O)NC1=CC=C(O)C=C1F QBZQDEQDWGLWON-UHFFFAOYSA-N 0.000 claims description 2
- KEMFFAOYGXDTDT-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)C(C)(C)CC2 KEMFFAOYGXDTDT-UHFFFAOYSA-N 0.000 claims description 2
- LXGLPFYNRBSCJA-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-6,6-dimethyl-4-oxo-5,7-dihydro-1h-indole-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CC(C)(C)C2 LXGLPFYNRBSCJA-UHFFFAOYSA-N 0.000 claims description 2
- LIUNBCDAAOZZBN-UHFFFAOYSA-N n-(2-fluoro-5-methoxyphenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound COC1=CC=C(F)C(NC(=O)C=2C=3C(=O)C(C)(C)CCC=3NC=2)=C1 LIUNBCDAAOZZBN-UHFFFAOYSA-N 0.000 claims description 2
- LWAPYMYVFBKDGC-UHFFFAOYSA-N n-(2-hydroxy-4-methylphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound OC1=CC(C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 LWAPYMYVFBKDGC-UHFFFAOYSA-N 0.000 claims description 2
- AHEWTJXJNYOQDP-UHFFFAOYSA-N n-(2-hydroxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound OC1=CC=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 AHEWTJXJNYOQDP-UHFFFAOYSA-N 0.000 claims description 2
- KSCYMEIPXDMHRD-UHFFFAOYSA-N n-(3-chlorophenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2C=3C(=O)CCCC=3NC=2)=C1 KSCYMEIPXDMHRD-UHFFFAOYSA-N 0.000 claims description 2
- PLMZGXXGFUXQPF-UHFFFAOYSA-N n-(3-fluoro-4-methoxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 PLMZGXXGFUXQPF-UHFFFAOYSA-N 0.000 claims description 2
- HFGBVJNPSPUDSR-UHFFFAOYSA-N n-(3-fluorophenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC=CC(NC(=O)C=2C=3C(=O)CCCC=3NC=2)=C1 HFGBVJNPSPUDSR-UHFFFAOYSA-N 0.000 claims description 2
- SWRGVMCNLFTUMC-UHFFFAOYSA-N n-(3-fluorophenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=2C(=O)C(C)(C)CCC=2NC=C1C(=O)NC1=CC=CC(F)=C1 SWRGVMCNLFTUMC-UHFFFAOYSA-N 0.000 claims description 2
- MAJDVJUSYGOCKR-UHFFFAOYSA-N n-(3-fluorophenyl)-6,6-dimethyl-4-oxo-5,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=2C(=O)CC(C)(C)CC=2NC=C1C(=O)NC1=CC=CC(F)=C1 MAJDVJUSYGOCKR-UHFFFAOYSA-N 0.000 claims description 2
- WKHZWRXRSJSVEC-UHFFFAOYSA-N n-(3-methoxyphenyl)-5,5-dimethyl-4-oxo-6,7-dihydro-1h-indole-3-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2C=3C(=O)C(C)(C)CCC=3NC=2)=C1 WKHZWRXRSJSVEC-UHFFFAOYSA-N 0.000 claims description 2
- MRGDWTWZCYRADO-UHFFFAOYSA-N n-(4-chloro-2-hydroxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound OC1=CC(Cl)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 MRGDWTWZCYRADO-UHFFFAOYSA-N 0.000 claims description 2
- SFLJHLAYAZCFGR-UHFFFAOYSA-N n-(4-ethoxy-2-fluorophenyl)-6,6-dimethyl-4-oxo-5,7-dihydro-1h-indole-3-carboxamide Chemical compound FC1=CC(OCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CC(C)(C)C2 SFLJHLAYAZCFGR-UHFFFAOYSA-N 0.000 claims description 2
- SRCTXUJXHZRLPT-UHFFFAOYSA-N n-(4-ethoxyphenyl)-6,6-dimethyl-4-oxo-5,7-dihydro-1h-indole-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CC(C)(C)C2 SRCTXUJXHZRLPT-UHFFFAOYSA-N 0.000 claims description 2
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- MFOFHBREHFKYLD-UHFFFAOYSA-N n-(2-fluoro-4-methoxyphenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 MFOFHBREHFKYLD-UHFFFAOYSA-N 0.000 description 1
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- STWILKGAVOVGDF-UHFFFAOYSA-N n-(4-chlorophenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 STWILKGAVOVGDF-UHFFFAOYSA-N 0.000 description 1
- KHUIAGZSJVROLE-UHFFFAOYSA-N n-(4-cyanophenyl)-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CC=C(C#N)C=C1 KHUIAGZSJVROLE-UHFFFAOYSA-N 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 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
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- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000004799 sedative–hypnotic effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
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- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229960003386 triazolam Drugs 0.000 description 1
- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Multicomponent Fibers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/683,066 US5750702A (en) | 1993-10-27 | 1996-07-16 | Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain receptor ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP970385A2 true HRP970385A2 (en) | 1998-08-31 |
Family
ID=24742434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR08/683,066A HRP970385A2 (en) | 1996-07-16 | 1997-07-16 | Certain fused pyrrolecarboxanilides; new class of gaba brain receptor ligands |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US5750702A (fr) |
| AU (2) | AU2832897A (fr) |
| CO (1) | CO4900050A1 (fr) |
| DZ (1) | DZ2271A1 (fr) |
| HR (1) | HRP970385A2 (fr) |
| MA (1) | MA27120A1 (fr) |
| PA (1) | PA8434101A1 (fr) |
| PE (1) | PE91798A1 (fr) |
| WO (2) | WO1998002433A1 (fr) |
| ZA (1) | ZA976244B (fr) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2218997A (en) | 1996-03-22 | 1997-10-10 | Neurogen Corporation | Certain fused pyrrolecarboxamides as gaba brain receptor ligands |
| IL135710A0 (en) | 1997-11-13 | 2001-05-20 | Pfizer Prod Inc | Method of synthesis of pyrrole amides |
| AU736227B2 (en) * | 1997-12-03 | 2001-07-26 | Nihon Nohyaku Co., Ltd. | Nitrogen-containing tetracyclic compounds |
| US6103903A (en) | 1998-02-26 | 2000-08-15 | Neurogen Corporation | 4-(4-piperidylmethyhlamino) substituted heteroaryl fused pyridines: GABA brain receptor ligands |
| ES2243046T3 (es) | 1998-02-26 | 2005-11-16 | Neurogen Corporation | Carboxamidas cicloalquil-4-oxonicotinicas sustituidas; ligandos de receptores gaba del cerebro. |
| JPH11279040A (ja) | 1998-03-27 | 1999-10-12 | Kao Corp | 皮膚外用剤 |
| GB9812038D0 (en) | 1998-06-04 | 1998-07-29 | Merck Sharp & Dohme | Therapeutic compound |
| JP2002544197A (ja) * | 1999-05-06 | 2002-12-24 | ニューロゲン コーポレイション | 置換4−オキソ−キノリン−3−カルボキサミド:gaba脳受容体リガンド |
| US6375948B1 (en) * | 1999-07-12 | 2002-04-23 | Kao Corporation | Treating method for suppressing hair growth |
| KR20020027613A (ko) * | 1999-08-31 | 2002-04-13 | 해피 페너 ; 해리 에이치. 페너 2세 | 접합된 피롤카르복스아미드:가바 뇌 수용체 리간드 |
| US20050014939A1 (en) * | 1999-08-31 | 2005-01-20 | Neurogen Corporation | Fused pyrrolecarboxamides: GABA brain receptor ligands |
| WO2001092257A1 (fr) * | 2000-05-26 | 2001-12-06 | Neurogen Corporation | Oxo-imidazopyrimidine-carboxamides et leur utilisation comme ligands des recepteurs cerebraux gaba |
| US7112594B2 (en) | 2000-08-09 | 2006-09-26 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| WO2002046155A1 (fr) * | 2000-12-04 | 2002-06-13 | Pfizer Products Inc. | Synthese de pyrrolescarboxamides fusionnes |
| US6861529B2 (en) * | 2001-07-06 | 2005-03-01 | Pfizer Inc | Cycloalkypyrrole-3-carboxylic acid derivatives and heterocycloalkylpyrrole-3-carboxylic acid derivatives |
| EP1430032A2 (fr) * | 2001-09-24 | 2004-06-23 | Elan Pharmaceuticals, Inc. | Amines substituees pour le traitement de la maladie d'alzheimer |
| US6673811B1 (en) * | 2001-11-19 | 2004-01-06 | Neurogen Corporation | 1H-pyrrolo [3,2-b] pyridine-3-carboxylic acid amines as GABAA receptor ligands |
| AU2002366092A1 (en) * | 2001-11-19 | 2003-06-10 | Pfizer Products, Inc. | 1h-pyrrolo(3,2-b)pyridine-3-carboxylic acid amides |
| JP2005525333A (ja) * | 2002-02-07 | 2005-08-25 | ニューロジェン コーポレイション | 置換縮合ピラゾールカルボン酸アリールアミド及び関連化合物 |
| US20040122218A1 (en) * | 2002-12-20 | 2004-06-24 | Sean Turner | Pyrrolopyridine potassium channel openers |
| EP2275095A3 (fr) | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenese par modulation des recepteurs muscariniques |
| EP2258359A3 (fr) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenèse par modulation des récepteurs muscariniques avec sabcomeline |
| AU2006304787A1 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| EP1942879A1 (fr) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Modulation de la neurogenese dont la mediation est assuree par recepteur gaba |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| JP2009536669A (ja) | 2006-05-09 | 2009-10-15 | ブレインセルス,インコーポレイティド | アンジオテンシン調節による神経新生 |
| MX2008014320A (es) | 2006-05-09 | 2009-03-25 | Braincells Inc | Neurogenesis mediada por el receptor de 5-hidroxitriptamina. |
| BRPI0716604A2 (pt) | 2006-09-08 | 2013-04-09 | Braincells Inc | combinaÇÕes contendo um derivado de 4-acilaminopiridina |
| JP5373613B2 (ja) | 2006-10-16 | 2013-12-18 | バイオノミクス リミテッド | 新規な抗不安薬化合物 |
| US10954231B2 (en) | 2006-10-16 | 2021-03-23 | Bionomics Limited | Anxiolytic compounds |
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| WO2020148679A1 (fr) * | 2019-01-17 | 2020-07-23 | ViiV Healthcare UK (No.4) Limited | Procédé de préparation de fostemsavir |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3455943A (en) * | 1966-10-21 | 1969-07-15 | American Cyanamid Co | Certain 5,8-dihydro-beta-carbolines |
| JPS57123180A (en) * | 1980-12-17 | 1982-07-31 | Schering Ag | 3-substituted beta-carboline, manufacture and psychotropic drug containing same |
| DE3335323A1 (de) * | 1983-09-27 | 1985-04-04 | Schering AG, 1000 Berlin und 4709 Bergkamen | Substituierte ss-carboline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3535927A1 (de) * | 1985-10-04 | 1987-04-09 | Schering Ag | 3-vinyl- und 3-ethinyl-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel |
| EP0738717A1 (fr) * | 1990-10-09 | 1996-10-23 | Neurogen Corporation | Pyrimidines substituées comme intermédiaires de préparation de cycloalkyl et azacycloalkyl pyrrolopyrimidines |
| US5243049A (en) * | 1992-01-22 | 1993-09-07 | Neurogen Corporation | Certain pyrroloquinolinones: a new class of GABA brain receptor ligands |
| US5266698A (en) * | 1992-04-30 | 1993-11-30 | Neurogen Corporation | Certain aryl and cycloalkyl fused imidazopyrazinediones; a new class of GABA brain receptor ligands |
| US5484944A (en) * | 1993-10-27 | 1996-01-16 | Neurogen Corporation | Certain fused pyrrolecarboxanilides and their use as GABA brain receptor ligands |
| US5804686A (en) * | 1996-01-19 | 1998-09-08 | Neurogen Corporation | fused pyrrolecarboxamides; a new class of GABA brain receptor ligands |
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1996
- 1996-07-16 US US08/683,066 patent/US5750702A/en not_active Expired - Fee Related
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1997
- 1997-05-09 WO PCT/US1997/007830 patent/WO1998002433A1/fr not_active Ceased
- 1997-05-09 AU AU28328/97A patent/AU2832897A/en not_active Abandoned
- 1997-07-14 AU AU36604/97A patent/AU3660497A/en not_active Abandoned
- 1997-07-14 WO PCT/US1997/012153 patent/WO1998002420A1/fr not_active Ceased
- 1997-07-15 ZA ZA976244A patent/ZA976244B/xx unknown
- 1997-07-16 CO CO97040267A patent/CO4900050A1/es unknown
- 1997-07-16 PA PA19978434101A patent/PA8434101A1/es unknown
- 1997-07-16 MA MA24720A patent/MA27120A1/fr unknown
- 1997-07-16 PE PE1997000632A patent/PE91798A1/es not_active Application Discontinuation
- 1997-07-16 DZ DZ970121A patent/DZ2271A1/fr active
- 1997-07-16 HR HR08/683,066A patent/HRP970385A2/hr not_active Application Discontinuation
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1998
- 1998-05-05 US US09/073,030 patent/US5925770A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CO4900050A1 (es) | 2000-03-27 |
| PA8434101A1 (es) | 2000-05-24 |
| WO1998002433A1 (fr) | 1998-01-22 |
| AU2832897A (en) | 1998-02-09 |
| ZA976244B (en) | 1999-01-21 |
| AU3660497A (en) | 1998-02-09 |
| PE91798A1 (es) | 1999-01-07 |
| US5925770A (en) | 1999-07-20 |
| US5750702A (en) | 1998-05-12 |
| MA27120A1 (fr) | 2005-01-03 |
| DZ2271A1 (fr) | 2002-12-18 |
| WO1998002420A1 (fr) | 1998-01-22 |
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