CA2464888A1 - Pyridine derivatives as nmda-receptor subtype blockers - Google Patents
Pyridine derivatives as nmda-receptor subtype blockers Download PDFInfo
- Publication number
- CA2464888A1 CA2464888A1 CA002464888A CA2464888A CA2464888A1 CA 2464888 A1 CA2464888 A1 CA 2464888A1 CA 002464888 A CA002464888 A CA 002464888A CA 2464888 A CA2464888 A CA 2464888A CA 2464888 A1 CA2464888 A1 CA 2464888A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- formula
- amine
- dihydro
- compound
- 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
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 title claims description 8
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 title claims description 8
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 196
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
- VZOYVGQAPOCCMI-UHFFFAOYSA-N 6-(2-phenylethenyl)pyridin-2-amine Chemical compound NC1=CC=CC(C=CC=2C=CC=CC=2)=N1 VZOYVGQAPOCCMI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 201000010099 disease Diseases 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 15
- 230000004770 neurodegeneration Effects 0.000 claims description 10
- FFNZJRVGBNIAGP-UHFFFAOYSA-N [N-]=[N+]=NP(=O)(N=[N+]=[N-])N=[N+]=[N-].C1=CC=CC=C1C1=CC=CC=C1 Chemical compound [N-]=[N+]=NP(=O)(N=[N+]=[N-])N=[N+]=[N-].C1=CC=CC=C1C1=CC=CC=C1 FFNZJRVGBNIAGP-UHFFFAOYSA-N 0.000 claims description 8
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 8
- 230000001684 chronic effect Effects 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- KGFGDIMGKWUXPR-UHFFFAOYSA-N 2-(3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound NC1=CC=NC(C=2CCC3=CC=CC=C3C=2)=C1 KGFGDIMGKWUXPR-UHFFFAOYSA-N 0.000 claims description 3
- HROXYBXSZXJQQN-VOTSOKGWSA-N 2-[(e)-2-phenylethenyl]pyridin-4-amine Chemical compound NC1=CC=NC(\C=C\C=2C=CC=CC=2)=C1 HROXYBXSZXJQQN-VOTSOKGWSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- BALMNUYDNZTRGL-UHFFFAOYSA-N 2-(3,4-dihydronaphthalen-2-yl)-6-methylpyridin-4-amine Chemical compound CC1=CC(N)=CC(C=2CCC3=CC=CC=C3C=2)=N1 BALMNUYDNZTRGL-UHFFFAOYSA-N 0.000 claims description 2
- SNKWOEPQIIAWDS-UHFFFAOYSA-N 2-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound C=1C2=CC=CC=C2C(C)CC=1C1=CC(N)=CC=N1 SNKWOEPQIIAWDS-UHFFFAOYSA-N 0.000 claims description 2
- DLGPEZQGUDCXJM-UHFFFAOYSA-N 2-(5,7-dimethyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound C=1C2=CC(C)=CC(C)=C2CCC=1C1=CC(N)=CC=N1 DLGPEZQGUDCXJM-UHFFFAOYSA-N 0.000 claims description 2
- QVQQJPQHCUCAOD-UHFFFAOYSA-N 2-(6,7-dihydro-1-benzothiophen-5-yl)-5-methylpyridin-4-amine Chemical compound C1=C(N)C(C)=CN=C1C(CC1)=CC2=C1SC=C2 QVQQJPQHCUCAOD-UHFFFAOYSA-N 0.000 claims description 2
- VPEVEVRKQIKMEA-UHFFFAOYSA-N 2-(6,7-dihydro-1-benzothiophen-5-yl)pyridin-4-amine Chemical compound NC1=CC=NC(C=2CCC=3SC=CC=3C=2)=C1 VPEVEVRKQIKMEA-UHFFFAOYSA-N 0.000 claims description 2
- ZHMNZUJREAWPIV-UHFFFAOYSA-N 2-(7-chloro-3,4-dihydronaphthalen-2-yl)-6-methylpyridin-4-amine Chemical compound CC1=CC(N)=CC(C=2CCC3=CC=C(Cl)C=C3C=2)=N1 ZHMNZUJREAWPIV-UHFFFAOYSA-N 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 2
- GNTNYOIAUFZGPK-UHFFFAOYSA-N 2-methyl-6-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound C=1C2=CC=CC=C2C(C)CC=1C1=CC(N)=CC(C)=N1 GNTNYOIAUFZGPK-UHFFFAOYSA-N 0.000 claims description 2
- MBKZSODXPUTTHT-UHFFFAOYSA-N 5-methyl-2-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound C=1C2=CC=CC=C2C(C)CC=1C1=CC(N)=C(C)C=N1 MBKZSODXPUTTHT-UHFFFAOYSA-N 0.000 claims description 2
- XHUQFKUYBTVYNB-BQYQJAHWSA-N 6-methyl-4-[(e)-2-phenylethenyl]pyridin-2-amine Chemical compound NC1=NC(C)=CC(\C=C\C=2C=CC=CC=2)=C1 XHUQFKUYBTVYNB-BQYQJAHWSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- IMJOZNZWAXXSQG-MDZDMXLPSA-N [6-[(e)-2-phenylethenyl]pyridin-2-yl]methanamine Chemical compound NCC1=CC=CC(\C=C\C=2C=CC=CC=2)=N1 IMJOZNZWAXXSQG-MDZDMXLPSA-N 0.000 claims description 2
- VXARDGMDMUMINC-UHFFFAOYSA-N 2-(2-phenylethenyl)pyridin-3-amine Chemical compound NC1=CC=CN=C1C=CC1=CC=CC=C1 VXARDGMDMUMINC-UHFFFAOYSA-N 0.000 claims 2
- WLDMSTVZYSHYAN-UHFFFAOYSA-N 4-(2-phenylethenyl)pyridin-2-amine Chemical compound C1=NC(N)=CC(C=CC=2C=CC=CC=2)=C1 WLDMSTVZYSHYAN-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- POZGKKTZKLMMIG-UHFFFAOYSA-N [4-amino-6-(3,4-dihydronaphthalen-2-yl)pyridin-2-yl]methanol Chemical compound NC1=CC(CO)=NC(C=2CCC3=CC=CC=C3C=2)=C1 POZGKKTZKLMMIG-UHFFFAOYSA-N 0.000 claims 1
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- 238000007429 general method Methods 0.000 description 66
- 239000002178 crystalline material Substances 0.000 description 54
- 239000000243 solution Substances 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 32
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 29
- 238000002425 crystallisation Methods 0.000 description 28
- 230000008025 crystallization Effects 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 238000000605 extraction Methods 0.000 description 23
- 239000012458 free base Substances 0.000 description 23
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 17
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- XPXMEYHPXJQPHD-UHFFFAOYSA-N 3,4-dihydronaphthalen-2-ylboronic acid Chemical compound C1=CC=C2CCC(B(O)O)=CC2=C1 XPXMEYHPXJQPHD-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 229910052681 coesite Inorganic materials 0.000 description 14
- 229910052906 cristobalite Inorganic materials 0.000 description 14
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 14
- 239000011343 solid material Substances 0.000 description 14
- 229910052682 stishovite Inorganic materials 0.000 description 14
- 229910052905 tridymite Inorganic materials 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 12
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
- 238000010626 work up procedure Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 10
- CFZKDDTWZYUZKS-UHFFFAOYSA-N picoline N-oxide Chemical compound CC1=CC=CC=[N+]1[O-] CFZKDDTWZYUZKS-UHFFFAOYSA-N 0.000 description 10
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 10
- GNTGEMWEXKBWBX-UHFFFAOYSA-N 2-bromopyridin-4-amine Chemical compound NC1=CC=NC(Br)=C1 GNTGEMWEXKBWBX-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 7
- RQRVBAKTSNWUCG-UHFFFAOYSA-N (4-methyl-3,4-dihydronaphthalen-2-yl)boronic acid Chemical compound C1=CC=C2C(C)CC(B(O)O)=CC2=C1 RQRVBAKTSNWUCG-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 229910017974 NH40H Inorganic materials 0.000 description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PQLQHLYTDHTKMA-UHFFFAOYSA-N (7-chloro-3,4-dihydronaphthalen-2-yl)boronic acid Chemical compound ClC1=CC=C2CCC(B(O)O)=CC2=C1 PQLQHLYTDHTKMA-UHFFFAOYSA-N 0.000 description 4
- NZTRUPUDUVCDTC-UHFFFAOYSA-N 2-bromo-5-methylpyridin-4-amine Chemical compound CC1=CN=C(Br)C=C1N NZTRUPUDUVCDTC-UHFFFAOYSA-N 0.000 description 4
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- -1 N-substituted pyridones Chemical class 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- GKNGDJAGDPAQHO-UHFFFAOYSA-N 2-bromo-6-methylpyridin-4-amine Chemical compound CC1=CC(N)=CC(Br)=N1 GKNGDJAGDPAQHO-UHFFFAOYSA-N 0.000 description 3
- AGCRAAGEEVNBDW-UHFFFAOYSA-N 3-bromo-1,2-dihydronaphthalene Chemical compound C1=CC=C2CCC(Br)=CC2=C1 AGCRAAGEEVNBDW-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- FTLLNKOZZWBNGQ-UHFFFAOYSA-N (4-amino-6-bromopyridin-2-yl)methanol Chemical compound NC1=CC(Br)=NC(CO)=C1 FTLLNKOZZWBNGQ-UHFFFAOYSA-N 0.000 description 2
- LJPUFILQQPNRIZ-UHFFFAOYSA-N (5,8-dimethyl-3,4-dihydronaphthalen-2-yl)boronic acid Chemical compound C1=C(B(O)O)CCC2=C1C(C)=CC=C2C LJPUFILQQPNRIZ-UHFFFAOYSA-N 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- ZIWURGNJCPGIHH-UHFFFAOYSA-N 2-(3,4-dihydronaphthalen-2-yl)-n-methylpyridin-4-amine Chemical compound CNC1=CC=NC(C=2CCC3=CC=CC=C3C=2)=C1 ZIWURGNJCPGIHH-UHFFFAOYSA-N 0.000 description 2
- LLQYEOURPDWIBV-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethenyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1C=CC1=CC=C(F)C=C1 LLQYEOURPDWIBV-UHFFFAOYSA-N 0.000 description 2
- KUENSPFFYCYXPO-UHFFFAOYSA-N 2-bromo-6-ethyl-4-nitro-1-oxidopyridin-1-ium Chemical compound CCC1=CC([N+]([O-])=O)=CC(Br)=[N+]1[O-] KUENSPFFYCYXPO-UHFFFAOYSA-N 0.000 description 2
- WMGGGRSAPQTRAA-UHFFFAOYSA-N 2-bromo-6-ethylpyridin-4-amine Chemical compound CCC1=CC(N)=CC(Br)=N1 WMGGGRSAPQTRAA-UHFFFAOYSA-N 0.000 description 2
- MMKZTFKQWMVBTI-UHFFFAOYSA-N 3-bromo-1-methyl-1,2-dihydronaphthalene Chemical compound C1=CC=C2C(C)CC(Br)=CC2=C1 MMKZTFKQWMVBTI-UHFFFAOYSA-N 0.000 description 2
- RCJVLYIMTGSSSH-UHFFFAOYSA-N 3-bromo-6-chloro-1,2-dihydronaphthalene Chemical compound C1CC(Br)=CC2=CC(Cl)=CC=C21 RCJVLYIMTGSSSH-UHFFFAOYSA-N 0.000 description 2
- JJRLJTJZVTWBQX-UHFFFAOYSA-N 3-bromo-6-methoxy-1,2-dihydronaphthalene Chemical compound C1CC(Br)=CC2=CC(OC)=CC=C21 JJRLJTJZVTWBQX-UHFFFAOYSA-N 0.000 description 2
- UQRDDFPHSHBPAQ-UHFFFAOYSA-N 3-bromo-8-methoxy-1,2-dihydronaphthalene Chemical compound C1=C(Br)CCC2=C1C=CC=C2OC UQRDDFPHSHBPAQ-UHFFFAOYSA-N 0.000 description 2
- CKHDIIKCMLOVRM-UHFFFAOYSA-N 6,7-dihydro-1-benzothiophen-5-ylboronic acid Chemical compound C1CC(B(O)O)=CC2=C1SC=C2 CKHDIIKCMLOVRM-UHFFFAOYSA-N 0.000 description 2
- GRAJXPFMPCDPSP-UHFFFAOYSA-N 6-[2-(2-fluorophenyl)ethenyl]pyridine-2-carbonitrile Chemical compound FC1=CC=CC=C1C=CC1=CC=CC(C#N)=N1 GRAJXPFMPCDPSP-UHFFFAOYSA-N 0.000 description 2
- NIENSBMFUDXTJJ-UHFFFAOYSA-N 6-[2-(4-methylphenyl)ethenyl]pyridine-2-carbonitrile Chemical compound C1=CC(C)=CC=C1C=CC1=CC=CC(C#N)=N1 NIENSBMFUDXTJJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229960003887 dichlorophen Drugs 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 230000007996 neuronal plasticity Effects 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical class [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 2
- 239000012256 powdered iron Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- SENXCDRAXNPDOK-UHFFFAOYSA-N tributyl-[(z)-2-phenylethenyl]stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=CC1=CC=CC=C1 SENXCDRAXNPDOK-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- HIRUPRSVCWQXAA-UHFFFAOYSA-N (5,7-dimethyl-3,4-dihydronaphthalen-2-yl)boronic acid Chemical compound C1CC(B(O)O)=CC2=CC(C)=CC(C)=C21 HIRUPRSVCWQXAA-UHFFFAOYSA-N 0.000 description 1
- YNSYNSOXGQDKCL-UHFFFAOYSA-N (5-methoxy-3,4-dihydronaphthalen-2-yl)boronic acid Chemical compound C1=C(B(O)O)CCC2=C1C=CC=C2OC YNSYNSOXGQDKCL-UHFFFAOYSA-N 0.000 description 1
- XDDGKNRSCDEWBR-UHFFFAOYSA-N (6-bromopyridin-2-yl)methanol Chemical compound OCC1=CC=CC(Br)=N1 XDDGKNRSCDEWBR-UHFFFAOYSA-N 0.000 description 1
- TXDWKJBVOZWHQN-UHFFFAOYSA-N (7-methoxy-3,4-dihydronaphthalen-2-yl)boronic acid Chemical compound C1CC(B(O)O)=CC2=CC(OC)=CC=C21 TXDWKJBVOZWHQN-UHFFFAOYSA-N 0.000 description 1
- RKCXHCWADUKCPU-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(3,4-dihydronaphthalen-2-yl)-5-methylpyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C1=C(N)C(C)=CN=C1C1=CC2=CC=CC=C2CC1 RKCXHCWADUKCPU-WLHGVMLRSA-N 0.000 description 1
- DMHMNGPUZZJYCB-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(3,4-dihydronaphthalen-2-yl)-6-ethylpyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.CCC1=CC(N)=CC(C=2CCC3=CC=CC=C3C=2)=N1 DMHMNGPUZZJYCB-WLHGVMLRSA-N 0.000 description 1
- MRMCMFDXFRFCLU-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(3,4-dihydronaphthalen-2-yl)-6-methylpyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.CC1=CC(N)=CC(C=2CCC3=CC=CC=C3C=2)=N1 MRMCMFDXFRFCLU-WLHGVMLRSA-N 0.000 description 1
- UWBPWKFYOQUGFJ-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(3,4-dihydronaphthalen-2-yl)-n-methylpyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.CNC1=CC=NC(C=2CCC3=CC=CC=C3C=2)=C1 UWBPWKFYOQUGFJ-WLHGVMLRSA-N 0.000 description 1
- OKIHTIHVPHLEAU-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C2=CC=CC=C2C(C)CC=1C1=CC(N)=CC=N1 OKIHTIHVPHLEAU-WLHGVMLRSA-N 0.000 description 1
- BSQTZNKHGVJKSH-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(5,7-dimethyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C2=CC(C)=CC(C)=C2CCC=1C1=CC(N)=CC=N1 BSQTZNKHGVJKSH-WLHGVMLRSA-N 0.000 description 1
- PFHHZCJFTXLCEG-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(5,8-dimethyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C1CC=2C(C)=CC=C(C)C=2C=C1C1=CC(N)=CC=N1 PFHHZCJFTXLCEG-WLHGVMLRSA-N 0.000 description 1
- RWGPVNVQTILFAS-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(5-methoxy-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C1CC=2C(OC)=CC=CC=2C=C1C1=CC(N)=CC=N1 RWGPVNVQTILFAS-WLHGVMLRSA-N 0.000 description 1
- HSPUONHQYYYOHI-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(6,7-dihydro-1-benzothiophen-5-yl)-5-methylpyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C1=C(N)C(C)=CN=C1C(CC1)=CC2=C1SC=C2 HSPUONHQYYYOHI-WLHGVMLRSA-N 0.000 description 1
- JBAYATIPCPQJKK-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(6,7-dihydro-1-benzothiophen-5-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.NC1=CC=NC(C=2CCC=3SC=CC=3C=2)=C1 JBAYATIPCPQJKK-WLHGVMLRSA-N 0.000 description 1
- AUXVYTNSRCLOFL-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(7-chloro-3,4-dihydronaphthalen-2-yl)-5-methylpyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C1=C(N)C(C)=CN=C1C1=CC2=CC(Cl)=CC=C2CC1 AUXVYTNSRCLOFL-WLHGVMLRSA-N 0.000 description 1
- XJDLPDIYHHLRDF-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(7-chloro-3,4-dihydronaphthalen-2-yl)-6-ethylpyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.CCC1=CC(N)=CC(C=2CCC3=CC=C(Cl)C=C3C=2)=N1 XJDLPDIYHHLRDF-WLHGVMLRSA-N 0.000 description 1
- RZQPVICHXQKTHU-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(7-chloro-3,4-dihydronaphthalen-2-yl)-6-methylpyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.CC1=CC(N)=CC(C=2CCC3=CC=C(Cl)C=C3C=2)=N1 RZQPVICHXQKTHU-WLHGVMLRSA-N 0.000 description 1
- GRVAWUNYMHOYPC-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(7-chloro-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.NC1=CC=NC(C=2CCC3=CC=C(Cl)C=C3C=2)=C1 GRVAWUNYMHOYPC-WLHGVMLRSA-N 0.000 description 1
- GDAOYGZIDCOJAV-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(7-methoxy-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C2=CC(OC)=CC=C2CCC=1C1=CC(N)=CC=N1 GDAOYGZIDCOJAV-WLHGVMLRSA-N 0.000 description 1
- LKMCTZFOQRRWSY-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-methyl-6-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C2=CC=CC=C2C(C)CC=1C1=CC(N)=CC(C)=N1 LKMCTZFOQRRWSY-WLHGVMLRSA-N 0.000 description 1
- FLPPDSFZDJVYIJ-WLHGVMLRSA-N (e)-but-2-enedioic acid;5-methyl-2-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C2=CC=CC=C2C(C)CC=1C1=CC(N)=C(C)C=N1 FLPPDSFZDJVYIJ-WLHGVMLRSA-N 0.000 description 1
- FPBKHNKBYUUOPI-WLHGVMLRSA-N (e)-but-2-enedioic acid;6-(3,4-dihydronaphthalen-2-yl)-4-methylpyridin-2-amine Chemical compound OC(=O)\C=C\C(O)=O.CC1=CC(N)=NC(C=2CCC3=CC=CC=C3C=2)=C1 FPBKHNKBYUUOPI-WLHGVMLRSA-N 0.000 description 1
- HIYGCTIBKTVXPY-WLHGVMLRSA-N (e)-but-2-enedioic acid;6-(3,4-dihydronaphthalen-2-yl)pyridin-2-amine Chemical compound OC(=O)\C=C\C(O)=O.NC1=CC=CC(C=2CCC3=CC=CC=C3C=2)=N1 HIYGCTIBKTVXPY-WLHGVMLRSA-N 0.000 description 1
- KMQVCYOPBMKRKH-UHFFFAOYSA-N 2,4-dimethyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=[N+]([O-])C(C)=C1 KMQVCYOPBMKRKH-UHFFFAOYSA-N 0.000 description 1
- BCWOWGNFAOJMGM-UHFFFAOYSA-N 2-(3,4-dihydronaphthalen-2-yl)-3-methylpyridin-4-amine Chemical compound CC1=C(N)C=CN=C1C1=CC2=CC=CC=C2CC1 BCWOWGNFAOJMGM-UHFFFAOYSA-N 0.000 description 1
- LPXNFVPRKGVHJB-UHFFFAOYSA-N 2-(3,4-dihydronaphthalen-2-yl)-5-methylpyridin-4-amine Chemical compound C1=C(N)C(C)=CN=C1C1=CC2=CC=CC=C2CC1 LPXNFVPRKGVHJB-UHFFFAOYSA-N 0.000 description 1
- LSSGJUXIMALCFZ-UHFFFAOYSA-N 2-(3,4-dihydronaphthalen-2-yl)-6-ethylpyridin-4-amine Chemical compound CCC1=CC(N)=CC(C=2CCC3=CC=CC=C3C=2)=N1 LSSGJUXIMALCFZ-UHFFFAOYSA-N 0.000 description 1
- FPENVWUCIPJDRP-UHFFFAOYSA-N 2-(3,4-dihydronaphthalen-2-yl)pyridin-4-amine;hydrochloride Chemical compound Cl.NC1=CC=NC(C=2CCC3=CC=CC=C3C=2)=C1 FPENVWUCIPJDRP-UHFFFAOYSA-N 0.000 description 1
- BKJZTWUBLZGNON-UHFFFAOYSA-N 2-(7-chloro-3,4-dihydronaphthalen-2-yl)-5-methylpyridin-4-amine Chemical compound C1=C(N)C(C)=CN=C1C1=CC2=CC(Cl)=CC=C2CC1 BKJZTWUBLZGNON-UHFFFAOYSA-N 0.000 description 1
- MTXVPTXXMDUOII-UHFFFAOYSA-N 2-(7-chloro-3,4-dihydronaphthalen-2-yl)-6-ethylpyridin-4-amine Chemical compound CCC1=CC(N)=CC(C=2CCC3=CC=C(Cl)C=C3C=2)=N1 MTXVPTXXMDUOII-UHFFFAOYSA-N 0.000 description 1
- KADSWFSQJACMOT-UHFFFAOYSA-N 2-(7-chloro-3,4-dihydronaphthalen-2-yl)pyridin-4-amine Chemical compound NC1=CC=NC(C=2CCC3=CC=C(Cl)C=C3C=2)=C1 KADSWFSQJACMOT-UHFFFAOYSA-N 0.000 description 1
- ONODUURCSWSVKT-UHFFFAOYSA-N 2-[(6-bromopyridin-2-yl)methyl]isoindole-1,3-dione Chemical compound BrC1=CC=CC(CN2C(C3=CC=CC=C3C2=O)=O)=N1 ONODUURCSWSVKT-UHFFFAOYSA-N 0.000 description 1
- BFXQIZCNGSXRLA-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)ethenyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1C=CC1=CC=CC=C1F BFXQIZCNGSXRLA-UHFFFAOYSA-N 0.000 description 1
- MHLMXXDAJZNDDG-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)ethenyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1C=CC1=CC=C(Cl)C(Cl)=C1 MHLMXXDAJZNDDG-UHFFFAOYSA-N 0.000 description 1
- IFKHUPULJFNXFV-UHFFFAOYSA-N 2-[2-(3-fluorophenyl)ethenyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1C=CC1=CC=CC(F)=C1 IFKHUPULJFNXFV-UHFFFAOYSA-N 0.000 description 1
- BNHVOHNUYOWMMU-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)ethenyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1C=CC1=CC=C(Cl)C=C1 BNHVOHNUYOWMMU-UHFFFAOYSA-N 0.000 description 1
- JAQHCTLLLPXFKE-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)ethenyl]-1-oxidopyridin-1-ium Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=CC=[N+]1[O-] JAQHCTLLLPXFKE-UHFFFAOYSA-N 0.000 description 1
- RHLSANBIICWEOF-UHFFFAOYSA-N 2-[2-(4-methylphenyl)ethenyl]-1-oxidopyridin-1-ium Chemical compound C1=CC(C)=CC=C1C=CC1=CC=CC=[N+]1[O-] RHLSANBIICWEOF-UHFFFAOYSA-N 0.000 description 1
- FOALETLLNZOGBX-UHFFFAOYSA-N 2-[[6-(3,4-dihydronaphthalen-2-yl)pyridin-2-yl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC=CC(C=2CCC3=CC=CC=C3C=2)=N1 FOALETLLNZOGBX-UHFFFAOYSA-N 0.000 description 1
- NYMGGRYETCRBSP-UHFFFAOYSA-N 2-bromo-3-methylpyridin-4-amine Chemical compound CC1=C(N)C=CN=C1Br NYMGGRYETCRBSP-UHFFFAOYSA-N 0.000 description 1
- RYMSPPQBKBRUQJ-UHFFFAOYSA-N 2-bromo-6-ethyl-1-oxidopyridin-1-ium Chemical compound CCC1=CC=CC(Br)=[N+]1[O-] RYMSPPQBKBRUQJ-UHFFFAOYSA-N 0.000 description 1
- TYOSQEKDQKYBLX-UHFFFAOYSA-N 2-bromo-6-ethylpyridine Chemical compound CCC1=CC=CC(Br)=N1 TYOSQEKDQKYBLX-UHFFFAOYSA-N 0.000 description 1
- BVBRVPXLHHOEMP-UHFFFAOYSA-N 2-bromo-6-methyl-4-nitropyridine Chemical compound CC1=CC([N+]([O-])=O)=CC(Br)=N1 BVBRVPXLHHOEMP-UHFFFAOYSA-N 0.000 description 1
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- QGFSOFXRHCBDOR-UHFFFAOYSA-N 2-methyl-1-oxido-4-(2-phenylethenyl)pyridin-1-ium Chemical compound C1=[N+]([O-])C(C)=CC(C=CC=2C=CC=CC=2)=C1 QGFSOFXRHCBDOR-UHFFFAOYSA-N 0.000 description 1
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- JKPQFURLBLYFEI-UHFFFAOYSA-N 3-bromo-5,8-dimethyl-1,2-dihydronaphthalene Chemical compound C1=C(Br)CCC2=C1C(C)=CC=C2C JKPQFURLBLYFEI-UHFFFAOYSA-N 0.000 description 1
- RXOWUUMYGRPGCN-UHFFFAOYSA-N 3-bromo-6,8-dimethyl-1,2-dihydronaphthalene Chemical compound C1CC(Br)=CC2=CC(C)=CC(C)=C21 RXOWUUMYGRPGCN-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WLDMSTVZYSHYAN-VOTSOKGWSA-N 4-[(e)-2-phenylethenyl]pyridin-2-amine Chemical compound C1=NC(N)=CC(\C=C\C=2C=CC=CC=2)=C1 WLDMSTVZYSHYAN-VOTSOKGWSA-N 0.000 description 1
- LOHVGTALVAZTLI-UHFFFAOYSA-N 4-[2-(6-aminopyridin-2-yl)ethenyl]phenol Chemical compound NC1=CC=CC(C=CC=2C=CC(O)=CC=2)=N1 LOHVGTALVAZTLI-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- HFMSNWKTEBOFMB-UHFFFAOYSA-N 4-methyl-1-oxido-2-(2-phenylethenyl)pyridin-1-ium Chemical compound CC1=CC=[N+]([O-])C(C=CC=2C=CC=CC=2)=C1 HFMSNWKTEBOFMB-UHFFFAOYSA-N 0.000 description 1
- IWYYIZOHWPCALJ-UHFFFAOYSA-N 4-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=[N+]([O-])C=C1 IWYYIZOHWPCALJ-UHFFFAOYSA-N 0.000 description 1
- SRLHDEROUKFEMJ-UHFFFAOYSA-N 4-methyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(C)CCC(=O)C2=C1 SRLHDEROUKFEMJ-UHFFFAOYSA-N 0.000 description 1
- JNKAKPOJAADXPI-BQYQJAHWSA-N 4-methyl-6-[(e)-2-phenylethenyl]pyridin-2-amine Chemical compound CC1=CC(N)=NC(\C=C\C=2C=CC=CC=2)=C1 JNKAKPOJAADXPI-BQYQJAHWSA-N 0.000 description 1
- UYJCNOMEGPDXMV-UHFFFAOYSA-N 5,7-dimethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(C)=CC(C)=C21 UYJCNOMEGPDXMV-UHFFFAOYSA-N 0.000 description 1
- ZSMGKPHICFZGQU-UHFFFAOYSA-N 5,8-dimethyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=C1C(C)=CC=C2C ZSMGKPHICFZGQU-UHFFFAOYSA-N 0.000 description 1
- OZMWCXRDJTYBLE-UHFFFAOYSA-N 5-bromo-6,7-dihydro-1-benzothiophene Chemical compound C1CC(Br)=CC2=C1SC=C2 OZMWCXRDJTYBLE-UHFFFAOYSA-N 0.000 description 1
- BRCPWISABURVIH-UHFFFAOYSA-N 5-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=C1C=CC=C2OC BRCPWISABURVIH-UHFFFAOYSA-N 0.000 description 1
- GJEKNELSXNSYAQ-UHFFFAOYSA-N 6,7-dihydro-5h-1-benzothiophen-4-one Chemical compound O=C1CCCC2=C1C=CS2 GJEKNELSXNSYAQ-UHFFFAOYSA-N 0.000 description 1
- FQBMHRIQMFLSCR-UHFFFAOYSA-N 6-(2-phenylethenyl)pyridin-2-amine;hydrochloride Chemical compound Cl.NC1=CC=CC(C=CC=2C=CC=CC=2)=N1 FQBMHRIQMFLSCR-UHFFFAOYSA-N 0.000 description 1
- MXYRHLHQIBBEKY-UHFFFAOYSA-N 6-(2-phenylethenyl)pyridine-2-carbonitrile Chemical compound N#CC1=CC=CC(C=CC=2C=CC=CC=2)=N1 MXYRHLHQIBBEKY-UHFFFAOYSA-N 0.000 description 1
- BBMJIGBFGVZQBX-UHFFFAOYSA-N 6-[2-(2-fluorophenyl)ethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.NC1=CC=CC(C=CC=2C(=CC=CC=2)F)=N1 BBMJIGBFGVZQBX-UHFFFAOYSA-N 0.000 description 1
- FZBFCIYICUCTII-UHFFFAOYSA-N 6-[2-(2-fluorophenyl)ethenyl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C=CC=2C(=CC=CC=2)F)=N1 FZBFCIYICUCTII-UHFFFAOYSA-N 0.000 description 1
- FSNQLSWSVKHVAV-UHFFFAOYSA-N 6-[2-(3,4-dichlorophenyl)ethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.NC1=CC=CC(C=CC=2C=C(Cl)C(Cl)=CC=2)=N1 FSNQLSWSVKHVAV-UHFFFAOYSA-N 0.000 description 1
- ZORTYILIABFKGB-UHFFFAOYSA-N 6-[2-(3,4-dichlorophenyl)ethenyl]pyridine-2-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1C=CC1=CC=CC(C#N)=N1 ZORTYILIABFKGB-UHFFFAOYSA-N 0.000 description 1
- NZBIYQHWJOAGNH-UHFFFAOYSA-N 6-[2-(3,4-dichlorophenyl)ethenyl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C=CC=2C=C(Cl)C(Cl)=CC=2)=N1 NZBIYQHWJOAGNH-UHFFFAOYSA-N 0.000 description 1
- SJOPVKLOSCZRGI-UHFFFAOYSA-N 6-[2-(3-chlorophenyl)ethenyl]pyridine-2-carbonitrile Chemical compound ClC1=CC=CC(C=CC=2N=C(C=CC=2)C#N)=C1 SJOPVKLOSCZRGI-UHFFFAOYSA-N 0.000 description 1
- JFHOTMHHVOFUCW-UHFFFAOYSA-N 6-[2-(3-fluorophenyl)ethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.NC1=CC=CC(C=CC=2C=C(F)C=CC=2)=N1 JFHOTMHHVOFUCW-UHFFFAOYSA-N 0.000 description 1
- MVMOSYRXGGAGOB-UHFFFAOYSA-N 6-[2-(3-fluorophenyl)ethenyl]pyridine-2-carbonitrile Chemical compound FC1=CC=CC(C=CC=2N=C(C=CC=2)C#N)=C1 MVMOSYRXGGAGOB-UHFFFAOYSA-N 0.000 description 1
- UKCWRKJJRUJSNH-UHFFFAOYSA-N 6-[2-(3-fluorophenyl)ethenyl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C=CC=2C=C(F)C=CC=2)=N1 UKCWRKJJRUJSNH-UHFFFAOYSA-N 0.000 description 1
- WLSBFJRESJAPDC-UHFFFAOYSA-N 6-[2-(4-chlorophenyl)ethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.NC1=CC=CC(C=CC=2C=CC(Cl)=CC=2)=N1 WLSBFJRESJAPDC-UHFFFAOYSA-N 0.000 description 1
- PPQLMEUBYGAJQW-UHFFFAOYSA-N 6-[2-(4-chlorophenyl)ethenyl]pyridine-2-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C=CC1=CC=CC(C#N)=N1 PPQLMEUBYGAJQW-UHFFFAOYSA-N 0.000 description 1
- ODFRJVDOBDCUHW-UHFFFAOYSA-N 6-[2-(4-chlorophenyl)ethenyl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C=CC=2C=CC(Cl)=CC=2)=N1 ODFRJVDOBDCUHW-UHFFFAOYSA-N 0.000 description 1
- UWPOKFAPMLSDRT-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)ethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.NC1=CC=CC(C=CC=2C=CC(F)=CC=2)=N1 UWPOKFAPMLSDRT-UHFFFAOYSA-N 0.000 description 1
- IIZAXWMAYSQFSZ-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)ethenyl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C=CC=2C=CC(F)=CC=2)=N1 IIZAXWMAYSQFSZ-UHFFFAOYSA-N 0.000 description 1
- ZFWHTXJTDFTNIS-UHFFFAOYSA-N 6-[2-(4-methoxyphenyl)ethenyl]pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=CC(N)=N1 ZFWHTXJTDFTNIS-UHFFFAOYSA-N 0.000 description 1
- RATRZBSLWQBWIK-UHFFFAOYSA-N 6-[2-(4-methoxyphenyl)ethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C=CC1=CC=CC(N)=N1 RATRZBSLWQBWIK-UHFFFAOYSA-N 0.000 description 1
- MUBMUBOOWQULMM-UHFFFAOYSA-N 6-[2-(4-methoxyphenyl)ethenyl]pyridine-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=CC(C#N)=N1 MUBMUBOOWQULMM-UHFFFAOYSA-N 0.000 description 1
- HINVAJDIKQJSBE-UHFFFAOYSA-N 6-[2-(4-methylphenyl)ethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C=CC1=CC=CC(N)=N1 HINVAJDIKQJSBE-UHFFFAOYSA-N 0.000 description 1
- ADYVUKHHXFOQJK-UHFFFAOYSA-N 6-[2-[3-(trifluoromethyl)phenyl]ethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.NC1=CC=CC(C=CC=2C=C(C=CC=2)C(F)(F)F)=N1 ADYVUKHHXFOQJK-UHFFFAOYSA-N 0.000 description 1
- VCFURLNJKATQCY-UHFFFAOYSA-N 6-[2-[3-(trifluoromethyl)phenyl]ethenyl]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C=CC=2C=C(C=CC=2)C(F)(F)F)=N1 VCFURLNJKATQCY-UHFFFAOYSA-N 0.000 description 1
- ABYCTYJDRLQBMT-UHFFFAOYSA-N 6-bromo-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(Br)=C1 ABYCTYJDRLQBMT-UHFFFAOYSA-N 0.000 description 1
- YQBRMUXRAFVSPK-UHFFFAOYSA-N 6-bromo-4-nitropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC(Br)=N1 YQBRMUXRAFVSPK-UHFFFAOYSA-N 0.000 description 1
- BKLJUYPLUWUEOQ-UHFFFAOYSA-N 6-bromopyridin-2-amine Chemical compound NC1=CC=CC(Br)=N1 BKLJUYPLUWUEOQ-UHFFFAOYSA-N 0.000 description 1
- ZUZAVIPYHCABAA-UHFFFAOYSA-N 6-methyl-4-(2-phenylethenyl)pyridine-2-carbonitrile Chemical compound N#CC1=NC(C)=CC(C=CC=2C=CC=CC=2)=C1 ZUZAVIPYHCABAA-UHFFFAOYSA-N 0.000 description 1
- IUQRUYCOADRUEF-UHFFFAOYSA-N 6-methyl-4-(2-phenylethenyl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC(C)=CC(C=CC=2C=CC=CC=2)=C1 IUQRUYCOADRUEF-UHFFFAOYSA-N 0.000 description 1
- ZUZAVIPYHCABAA-BQYQJAHWSA-N 6-methyl-4-[(e)-2-phenylethenyl]pyridine-2-carbonitrile Chemical compound N#CC1=NC(C)=CC(\C=C\C=2C=CC=CC=2)=C1 ZUZAVIPYHCABAA-BQYQJAHWSA-N 0.000 description 1
- IIMAYXKDBHTQHC-UHFFFAOYSA-N 7-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(Cl)=CC=C21 IIMAYXKDBHTQHC-UHFFFAOYSA-N 0.000 description 1
- GABLTKRIYDNDIN-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(OC)=CC=C21 GABLTKRIYDNDIN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
- PYINEKIHSSJIKP-UHFFFAOYSA-N C1=CC=C2C(B(O)O)=CCCC2=C1 Chemical compound C1=CC=C2C(B(O)O)=CCCC2=C1 PYINEKIHSSJIKP-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- LHSDOMCUBHPPKJ-WLHGVMLRSA-N [4-amino-6-(3,4-dihydronaphthalen-2-yl)pyridin-2-yl]methanol;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.NC1=CC(CO)=NC(C=2CCC3=CC=CC=C3C=2)=C1 LHSDOMCUBHPPKJ-WLHGVMLRSA-N 0.000 description 1
- BNYSGUPEXJGGNC-RRABGKBLSA-N [6-[(e)-2-phenylethenyl]pyridin-2-yl]methanamine;hydrochloride Chemical compound Cl.NCC1=CC=CC(\C=C\C=2C=CC=CC=2)=N1 BNYSGUPEXJGGNC-RRABGKBLSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000001638 cerebellum Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- GNFNHAOQTZKBBX-UHFFFAOYSA-N ethyl 2-[[2-(3,4-dihydronaphthalen-2-yl)pyridin-4-yl]amino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC=NC(C=2CCC3=CC=CC=C3C=2)=C1 GNFNHAOQTZKBBX-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 210000001767 medulla oblongata Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PBWWZVWCSUOPTQ-ASTDGNLGSA-N n-methyl-6-[(e)-2-phenylethenyl]pyridin-2-amine;hydrochloride Chemical compound Cl.CNC1=CC=CC(\C=C\C=2C=CC=CC=2)=N1 PBWWZVWCSUOPTQ-ASTDGNLGSA-N 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01125765 | 2001-10-29 | ||
| EP01125765.6 | 2001-10-29 | ||
| PCT/EP2002/011782 WO2003037333A1 (en) | 2001-10-29 | 2002-10-22 | Pyridine derivatives as nmda-receptor subtype blockers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2464888A1 true CA2464888A1 (en) | 2003-05-08 |
Family
ID=8179103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002464888A Abandoned CA2464888A1 (en) | 2001-10-29 | 2002-10-22 | Pyridine derivatives as nmda-receptor subtype blockers |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US6951875B2 (enExample) |
| EP (1) | EP1443926A1 (enExample) |
| JP (1) | JP2005511559A (enExample) |
| KR (1) | KR100591935B1 (enExample) |
| CN (2) | CN1578662A (enExample) |
| AR (1) | AR037249A1 (enExample) |
| BR (1) | BR0213572A (enExample) |
| CA (1) | CA2464888A1 (enExample) |
| MX (1) | MXPA04003935A (enExample) |
| PL (1) | PL370693A1 (enExample) |
| RU (1) | RU2004116473A (enExample) |
| WO (1) | WO2003037333A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04000695A (es) * | 2001-07-23 | 2005-08-26 | Galileo Pharmaceuticals Inc | Compuestos citoprotectores, formulaciones farmaceuticas y cosmeticas y metodos. |
| EP1802587A4 (en) * | 2004-10-15 | 2010-02-17 | Astrazeneca Ab | SUBSTITUTED AMINO BINDINGS AND THEIR APPLICATIONS |
| WO2006041405A1 (en) * | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Substituted amino-pyrimidones and uses thereof |
| US20080287399A1 (en) * | 2004-12-14 | 2008-11-20 | Astrazeneca Ab | Substituted Aminopyridines and Uses Thereof |
| CN101360720A (zh) * | 2005-11-15 | 2009-02-04 | 阿斯利康(瑞典)有限公司 | 新颖的2-氨基嘧啶酮衍生物及其用途 |
| CN101360721A (zh) * | 2005-11-15 | 2009-02-04 | 阿斯利康(瑞典)有限公司 | 新颖的2-氨基嘧啶酮衍生物或2-氨基吡啶酮衍生物及其用途 |
| AR058381A1 (es) * | 2005-12-19 | 2008-01-30 | Astrazeneca Ab | Compuestos derivados de 2-aminopiridin-4-onas y una composicion farmaceutica |
| CN101460480A (zh) * | 2006-04-05 | 2009-06-17 | 阿斯利康(瑞典)有限公司 | 2-氨基嘧啶-4-酮类化合物及其用于治疗或预防Aβ相关病理的用途 |
| US8340014B2 (en) | 2007-12-26 | 2012-12-25 | Lg Electronics Inc. | Method for transmitting and receiving signals using multi-band radio frequencies |
| CN105622431A (zh) * | 2011-01-28 | 2016-06-01 | 肯塔基大学研究基金会 | 茋类似物和治疗癌症的方法 |
| US8993258B2 (en) * | 2012-06-12 | 2015-03-31 | The University Of Connecticut | Fluorinated voltage sensitive dyes, preparation thereof, and optical methods of use |
| CR20170462A (es) * | 2015-04-15 | 2018-02-01 | Hoffmann La Roche | Piridopirimidinonas y utilización de las mismas como moduladores de receptores nmda |
| US10300155B2 (en) | 2015-12-31 | 2019-05-28 | Washington University | Alpha-synuclein ligands |
| US10449186B2 (en) | 2017-06-21 | 2019-10-22 | University Of Kentucky Research Foundation | Phenylethynyl-substituted benzenes and heterocycles for the treatment of cancer |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5648369A (en) | 1991-11-20 | 1997-07-15 | University Of Kentucky Research Foundation | Aminoalkylpyridine compounds which are useful as anitconvulsant drugs, excitatory amino acid inhibitors and NMDA sigma receptor antagonists |
| PT754682E (pt) * | 1994-04-06 | 2002-03-28 | Nippon Shinyaku Co Ltd | Derivado de aminostilbazol e medicamento |
| PT885004E (pt) | 1996-03-08 | 2002-08-30 | Hoffmann La Roche | Utilizacao de derivados de 4-fenil-3,6-di-hidro-2h-piridilo como bloqueadores dos subtipos dos receptores nmda |
| US5869676A (en) | 1997-05-15 | 1999-02-09 | Vion Pharmaceuticals, Inc. | Process for the synthesis of ribonucleotide reductase inhibitors 3-AP and 3-AMP |
| TW544448B (en) * | 1997-07-11 | 2003-08-01 | Novartis Ag | Pyridine derivatives |
| TWI254043B (en) | 1999-06-08 | 2006-05-01 | Hoffmann La Roche | Ethanesulfonyl-piperidine derivatives having good affinity to N-methyl-D-aspartate (NMDA) receptor |
| ES2211420T3 (es) | 1999-07-21 | 2004-07-16 | F. Hoffmann-La Roche Ag | Derivados de triazol. |
| EP1088818B1 (en) | 1999-10-01 | 2004-11-03 | F. Hoffmann-La Roche Ag | Quinolin-4-yl derivatives |
-
2002
- 2002-10-21 US US10/277,002 patent/US6951875B2/en not_active Expired - Fee Related
- 2002-10-22 KR KR1020047006334A patent/KR100591935B1/ko not_active Expired - Fee Related
- 2002-10-22 RU RU2004116473/04A patent/RU2004116473A/ru not_active Application Discontinuation
- 2002-10-22 CN CNA028214242A patent/CN1578662A/zh active Pending
- 2002-10-22 BR BR0213572-8A patent/BR0213572A/pt not_active IP Right Cessation
- 2002-10-22 CA CA002464888A patent/CA2464888A1/en not_active Abandoned
- 2002-10-22 EP EP02782972A patent/EP1443926A1/en not_active Withdrawn
- 2002-10-22 JP JP2003539677A patent/JP2005511559A/ja active Pending
- 2002-10-22 PL PL02370693A patent/PL370693A1/xx not_active Application Discontinuation
- 2002-10-22 CN CNA2006100670615A patent/CN1837195A/zh active Pending
- 2002-10-22 MX MXPA04003935A patent/MXPA04003935A/es unknown
- 2002-10-22 WO PCT/EP2002/011782 patent/WO2003037333A1/en not_active Ceased
- 2002-10-25 AR ARP020104048A patent/AR037249A1/es not_active Application Discontinuation
-
2003
- 2003-09-26 US US10/672,950 patent/US7034044B2/en not_active Expired - Fee Related
-
2005
- 2005-10-21 US US11/255,526 patent/US20060058354A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AR037249A1 (es) | 2004-11-03 |
| US6951875B2 (en) | 2005-10-04 |
| US20040068118A1 (en) | 2004-04-08 |
| EP1443926A1 (en) | 2004-08-11 |
| WO2003037333A1 (en) | 2003-05-08 |
| PL370693A1 (en) | 2005-05-30 |
| JP2005511559A (ja) | 2005-04-28 |
| MXPA04003935A (es) | 2004-06-18 |
| CN1578662A (zh) | 2005-02-09 |
| RU2004116473A (ru) | 2005-11-10 |
| US7034044B2 (en) | 2006-04-25 |
| BR0213572A (pt) | 2004-10-26 |
| US20060058354A1 (en) | 2006-03-16 |
| KR100591935B1 (ko) | 2006-06-22 |
| US20030144525A1 (en) | 2003-07-31 |
| KR20050039710A (ko) | 2005-04-29 |
| CN1837195A (zh) | 2006-09-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2464888A1 (en) | Pyridine derivatives as nmda-receptor subtype blockers | |
| CA2273479C (en) | 6-phenylpyridyl-2-amine derivatives useful as nos inhibitors | |
| DE69112061T2 (de) | Bis-benzo oder Benzopyrido-cyclohepta piperiden-piperidyliden, piperazinderivate als PAF Antagonisten, und Zusammensetzungen. | |
| US2739968A (en) | Substituted piperidines | |
| CA2474578C (en) | Novel pyridin- and pyrimidin-derivatives | |
| CA2485926C (en) | (imidazol-1-yl-methyl)-pyridazine as nmda receptor blocker | |
| NO174390B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyridinyl-methyl-substituerte aromater og heteroaromater | |
| CZ303639B6 (cs) | N-Oxid derivátu 4-fenylpyridinu, zpusob jeho prípravy a lécivo s jeho obsahem | |
| AU2005297570A1 (en) | 3,6-substituted 5-arylamino-1H-pyridine-2-one derivatives and related compounds as poly(ADP-ribose)polymerase (PARP) inhibitors in the treatment of tissue damage or disease caused by necrosis or apoptosis | |
| TW200524872A (en) | Process for preparation of pyridine derivatives | |
| EP1448547B1 (en) | Pyridine derivatives as nmda receptor ligands | |
| AU2002351816A1 (en) | Pyridine Substituted Isoquinoline Derivatives | |
| AU9748498A (en) | 3-substituted tetrahydropyridopyrimidinone derivatives, method for producing the same, and their use | |
| EP1409460B1 (en) | Novel synthesis of heteroarylamine intermediate compounds | |
| US2970149A (en) | Certain 1-[(2-pyridyl)-lower alkyl]-2-(tertamino-lower alkyl)-indan-1-ols, and acid addition salts | |
| DE60221251T2 (de) | Bis(2-aryl-5-pyridyl)-derivative | |
| CN104557671B (zh) | 一种非索非那定及中间体的合成方法 | |
| EP0094422B1 (en) | Substituted pyridines | |
| AU2002349396A1 (en) | Pyridine derivatives as NMDA-receptor subtype blockers | |
| RU2330020C2 (ru) | НОВЫЕ ПРОИЗВОДНЫЕ АМИНОПИРИДИНА В КАЧЕСТВЕ АНТАГОНИСТОВ mGIuR5 | |
| CA2648892A1 (en) | Heterocyclic compounds suitable for treating disorders that respond to modulation of the serotonin 5ht6 receptor | |
| US3154556A (en) | Nu-pyridylethyl-2:3-polymethyleneindoles | |
| US4524210A (en) | 2,6-Di(t-butyl)-4-hydroxy-4-pyridyl-2,5-cyclohexadien-1-one intermediates | |
| PL44430B1 (enExample) | ||
| MXPA00002601A (en) | 3-substituted tetrahydropyridopyrimidinone derivatives, method for producing the same, and their use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |