CN101935322A - 二氮杂二环中枢神经系统活性剂 - Google Patents

Info

Publication number

CN101935322A

CN101935322A CN2010102450796A CN201010245079A CN101935322A CN 101935322 A CN101935322 A CN 101935322A CN 2010102450796 A CN2010102450796 A CN 2010102450796A CN 201010245079 A CN201010245079 A CN 201010245079A CN 101935322 A CN101935322 A CN 101935322A

Authority

CN

China

Prior art keywords

pyridyl

compound

diazabicylo

cis

pyrroles

Prior art date

2000-04-27

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

• Espacenet
• Global Dossier
• Discuss

• 210000003169 central nervous system Anatomy 0.000 title abstract description 12
• 239000013543 active substance Substances 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 506
• 241000124008 Mammalia Species 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 295
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 200
• -1 alkyl-carbonyl oxygen Chemical compound 0.000 claims description 198
• 238000000034 method Methods 0.000 claims description 93
• 229910052739 hydrogen Inorganic materials 0.000 claims description 69
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 68
• 239000001257 hydrogen Substances 0.000 claims description 67
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000003545 alkoxy group Chemical group 0.000 claims description 49
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
• YKPJEYXZEBLYCI-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole Chemical class C1=NC=C2C=NC=C21 YKPJEYXZEBLYCI-UHFFFAOYSA-N 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 35
• OWOIOZSALARIEF-UHFFFAOYSA-N pyrrolo[2,3-c]pyrrole Chemical class N1=CC2=CC=NC2=C1 OWOIOZSALARIEF-UHFFFAOYSA-N 0.000 claims description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
• 201000010099 disease Diseases 0.000 claims description 29
• 208000002193 Pain Diseases 0.000 claims description 28
• 230000036407 pain Effects 0.000 claims description 28
• 239000000651 prodrug Substances 0.000 claims description 25
• 229940002612 prodrug Drugs 0.000 claims description 25
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 239000001301 oxygen Substances 0.000 claims description 22
• 239000002858 neurotransmitter agent Substances 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 239000003937 drug carrier Substances 0.000 claims description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 7
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 7
• CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 7
• DQHQCRQWOJTKBG-SCZZXKLOSA-N (3ar,6ar)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class C1=NC(Cl)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 DQHQCRQWOJTKBG-SCZZXKLOSA-N 0.000 claims description 6
• DWTZVDYZXFFTFH-SKDRFNHKSA-N (3ar,6ar)-5-[6-bromo-5-(methoxymethyl)pyridin-3-yl]-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class N1=C(Br)C(COC)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 DWTZVDYZXFFTFH-SKDRFNHKSA-N 0.000 claims description 6
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
• 208000018737 Parkinson disease Diseases 0.000 claims description 6
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
• ZJLSTXGOFNDPFN-YPMHNXCESA-N (3ar,6ar)-5-(5-ethenylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class C=CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 ZJLSTXGOFNDPFN-YPMHNXCESA-N 0.000 claims description 5
• KWZWPEDWONELEI-YPMHNXCESA-N (3ar,6ar)-5-(5-ethylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class CCC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 KWZWPEDWONELEI-YPMHNXCESA-N 0.000 claims description 5
• OUNUIZLSDCKVGG-PWSUYJOCSA-N (3ar,6ar)-5-(5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 OUNUIZLSDCKVGG-PWSUYJOCSA-N 0.000 claims description 5
• JCSPUVOHNHERBJ-PWSUYJOCSA-N (3ar,6ar)-5-(6-bromo-5-ethenylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class C1=C(C=C)C(Br)=NC=C1N1C[C@@H]2NCC[C@@H]2C1 JCSPUVOHNHERBJ-PWSUYJOCSA-N 0.000 claims description 5
• KEKVMZXOMNEOQP-KOLCDFICSA-N (3ar,6ar)-5-(6-bromo-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class N1=C(Br)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 KEKVMZXOMNEOQP-KOLCDFICSA-N 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• FZHVWHFLHSHANF-SCZZXKLOSA-N (3ar,6ar)-1-(6-chloropyridin-3-yl)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical class C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2CC1 FZHVWHFLHSHANF-SCZZXKLOSA-N 0.000 claims description 4
• SUMBPLBCXUNGMO-KCJUWKMLSA-N (3ar,6ar)-5-(5-bromopyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class BrC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 SUMBPLBCXUNGMO-KCJUWKMLSA-N 0.000 claims description 4
• FDUANQGPNHRGGA-YPMHNXCESA-N (3ar,6ar)-5-(5-ethynylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class C#CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 FDUANQGPNHRGGA-YPMHNXCESA-N 0.000 claims description 4
• RUEPBFNTOSWZAB-KOLCDFICSA-N (3ar,6ar)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class N1=C(Cl)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 RUEPBFNTOSWZAB-KOLCDFICSA-N 0.000 claims description 4
• HMWDILXJWAOEJT-KOLCDFICSA-N (3ar,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class C([C@H]1CCN[C@H]1C1)N1C1=CC=CN=C1 HMWDILXJWAOEJT-KOLCDFICSA-N 0.000 claims description 4
• SUMBPLBCXUNGMO-GZMMTYOYSA-N (3as,6as)-5-(5-bromopyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class BrC1=CN=CC(N2C[C@H]3NCC[C@H]3C2)=C1 SUMBPLBCXUNGMO-GZMMTYOYSA-N 0.000 claims description 4
• RUEPBFNTOSWZAB-GXSJLCMTSA-N (3as,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3C2)=C1 RUEPBFNTOSWZAB-GXSJLCMTSA-N 0.000 claims description 4
• DQHQCRQWOJTKBG-WCBMZHEXSA-N (3as,6as)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2C1 DQHQCRQWOJTKBG-WCBMZHEXSA-N 0.000 claims description 4
• HMWDILXJWAOEJT-GXSJLCMTSA-N (3as,6as)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class C([C@@H]1CCN[C@@H]1C1)N1C1=CC=CN=C1 HMWDILXJWAOEJT-GXSJLCMTSA-N 0.000 claims description 4
• 206010057315 Daydreaming Diseases 0.000 claims description 4
• 239000001961 anticonvulsive agent Substances 0.000 claims description 4
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• 230000005586 smoking cessation Effects 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• ZCIPXINQRZWYCD-XCBNKYQSSA-N (3ar,6ar)-5-(6-bromo-5-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical class N1=C(Br)C(Cl)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 ZCIPXINQRZWYCD-XCBNKYQSSA-N 0.000 claims description 3
• 208000035475 disorder Diseases 0.000 claims description 3
• 208000024732 dysthymic disease Diseases 0.000 claims description 3
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
• NBPGBNNVEWLKEW-KOLCDFICSA-N (3ar,6ar)-1-pyridin-3-yl-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical class C([C@@H]1CNC[C@@H]11)CN1C1=CC=CN=C1 NBPGBNNVEWLKEW-KOLCDFICSA-N 0.000 claims description 2
• UBQWFBOLOFJCDH-PHIMTYICSA-N (3ar,6as)-2-methyl-5-pyridin-3-yl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole Chemical class C([C@@H]1CN(C[C@@H]1C1)C)N1C1=CC=CN=C1 UBQWFBOLOFJCDH-PHIMTYICSA-N 0.000 claims description 2
• OHWQUEIYHPZQPN-TXEJJXNPSA-N (3ar,6as)-5-(5-propoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical class CCCOC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 OHWQUEIYHPZQPN-TXEJJXNPSA-N 0.000 claims description 2
• GGWINWDBVWLKNK-AOOOYVTPSA-N (3ar,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical class N1=C(Cl)C(C)=CC(N2C[C@H]3CNC[C@H]3C2)=C1 GGWINWDBVWLKNK-AOOOYVTPSA-N 0.000 claims description 2
• WNQHCICGYPNPJA-DTORHVGOSA-N (3as,6ar)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical class C1=NC(Cl)=CC=C1N1C[C@H]2CNC[C@H]2C1 WNQHCICGYPNPJA-DTORHVGOSA-N 0.000 claims description 2
• QZPCTRNKBFDOCH-AOOOYVTPSA-N (3as,6ar)-5-(6-chloropyridin-3-yl)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole Chemical class C([C@@H]1CN(C[C@@H]1C1)C)N1C1=CC=C(Cl)N=C1 QZPCTRNKBFDOCH-AOOOYVTPSA-N 0.000 claims description 2
• KOMXDDRATCALPT-AOOOYVTPSA-N (3as,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical class C([C@H]1CNC[C@H]1C1)N1C1=CC=CN=C1 KOMXDDRATCALPT-AOOOYVTPSA-N 0.000 claims description 2
• FZHVWHFLHSHANF-WCBMZHEXSA-N (3as,6as)-1-(6-chloropyridin-3-yl)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical class C1=NC(Cl)=CC=C1N1[C@@H]2CNC[C@@H]2CC1 FZHVWHFLHSHANF-WCBMZHEXSA-N 0.000 claims description 2
• NBPGBNNVEWLKEW-GXSJLCMTSA-N (3as,6as)-1-pyridin-3-yl-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical class C([C@H]1CNC[C@H]11)CN1C1=CC=CN=C1 NBPGBNNVEWLKEW-GXSJLCMTSA-N 0.000 claims description 2
• YEUYAIVZZOYQGC-KOLCDFICSA-N (4ar,7ar)-6-(6-chloropyridin-3-yl)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NCCC[C@@H]2C1 YEUYAIVZZOYQGC-KOLCDFICSA-N 0.000 claims description 2
• ZRDHUIBTFTYXSF-PWSUYJOCSA-N (4ar,7ar)-6-pyridin-3-yl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C([C@@H]1NCCC[C@@H]1C1)N1C1=CC=CN=C1 ZRDHUIBTFTYXSF-PWSUYJOCSA-N 0.000 claims description 2
• KLNHDAVAIWEDTG-BETUJISGSA-N 3-[(3ar,6as)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]quinoline Chemical class C1=CC=CC2=CC(N3C[C@H]4CNC[C@H]4C3)=CN=C21 KLNHDAVAIWEDTG-BETUJISGSA-N 0.000 claims description 2
• VUGNXGAJCUBYBO-DTORHVGOSA-N 5-[(3as,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]pyridin-3-ol Chemical class OC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 VUGNXGAJCUBYBO-DTORHVGOSA-N 0.000 claims description 2
• IZNGUHXSMKBUJT-GZMMTYOYSA-N 5-[(3as,6as)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrol-1-yl]pyridin-3-ol Chemical class OC1=CN=CC(N2[C@@H]3CNC[C@@H]3CC2)=C1 IZNGUHXSMKBUJT-GZMMTYOYSA-N 0.000 claims description 2
• WZWFSJDVABFXKU-CMPLNLGQSA-N C([C@@H]1CCN[C@@H]1C1)CN1C1=CC=CN=C1 Chemical group C([C@@H]1CCN[C@@H]1C1)CN1C1=CC=CN=C1 WZWFSJDVABFXKU-CMPLNLGQSA-N 0.000 claims description 2
• GZQLLEREELILKV-KOLCDFICSA-N C([C@@H]1CN(C[C@@H]11)C)CN1C1=CC=C(Cl)N=C1 Chemical class C([C@@H]1CN(C[C@@H]11)C)CN1C1=CC=C(Cl)N=C1 GZQLLEREELILKV-KOLCDFICSA-N 0.000 claims description 2
• 239000000203 mixture Substances 0.000 abstract description 178
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 abstract description 23
• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 abstract description 23
• 239000003446 ligand Substances 0.000 abstract description 6
• 230000005062 synaptic transmission Effects 0.000 abstract description 2
• 239000000047 product Substances 0.000 description 238
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 173
• 239000000243 solution Substances 0.000 description 169
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 136
• 230000002829 reductive effect Effects 0.000 description 120
• 239000000460 chlorine Substances 0.000 description 99
• 229910004298 SiO 2 Inorganic materials 0.000 description 94
• 238000004587 chromatography analysis Methods 0.000 description 93
• 229920002554 vinyl polymer Polymers 0.000 description 89
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 88
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 88
• 239000000178 monomer Substances 0.000 description 86
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
• 239000007787 solid Substances 0.000 description 83
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
• 238000005160 1H NMR spectroscopy Methods 0.000 description 75
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
• 239000003921 oil Substances 0.000 description 69
• 235000019198 oils Nutrition 0.000 description 69
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 68
• 238000003756 stirring Methods 0.000 description 68
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 66
• 239000002585 base Substances 0.000 description 62
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
• 238000005481 NMR spectroscopy Methods 0.000 description 57
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
• 229960004756 ethanol Drugs 0.000 description 55
• 238000012545 processing Methods 0.000 description 53
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• 239000000706 filtrate Substances 0.000 description 50
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 44
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 238000002360 preparation method Methods 0.000 description 41
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 40
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 40
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• 238000000605 extraction Methods 0.000 description 36
• 238000000746 purification Methods 0.000 description 36
• 238000005406 washing Methods 0.000 description 36
• 239000003814 drug Substances 0.000 description 33
• 238000010438 heat treatment Methods 0.000 description 33
• BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 32
• 238000001914 filtration Methods 0.000 description 29
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• 239000012299 nitrogen atmosphere Substances 0.000 description 27
• 239000003795 chemical substances by application Substances 0.000 description 26
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 25
• 229910052799 carbon Inorganic materials 0.000 description 24
• 239000003513 alkali Substances 0.000 description 23
• 239000012043 crude product Substances 0.000 description 23
• 239000001530 fumaric acid Substances 0.000 description 23
• JSZIERUELMKQRO-WLHGVMLRSA-N (e)-but-2-enedioic acid;heptane Chemical compound CCCCCCC.OC(=O)\C=C\C(O)=O JSZIERUELMKQRO-WLHGVMLRSA-N 0.000 description 22
• 229910052731 fluorine Inorganic materials 0.000 description 22
• 239000012141 concentrate Substances 0.000 description 21
• 235000008504 concentrate Nutrition 0.000 description 21
• 239000011737 fluorine Substances 0.000 description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
• 229910052763 palladium Inorganic materials 0.000 description 21
• 230000000694 effects Effects 0.000 description 20
• 150000002148 esters Chemical class 0.000 description 20
• 239000011734 sodium Substances 0.000 description 20
• 150000001335 aliphatic alkanes Chemical class 0.000 description 19
• 239000007864 aqueous solution Substances 0.000 description 18
• 238000001035 drying Methods 0.000 description 18
• 239000012074 organic phase Substances 0.000 description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
• 239000007788 liquid Substances 0.000 description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
• 239000002253 acid Substances 0.000 description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
• 150000004985 diamines Chemical class 0.000 description 16
• 239000012266 salt solution Substances 0.000 description 16
• 239000000126 substance Substances 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• DZAHXNNEQCZPGJ-UHFFFAOYSA-N CCCCOC(OC)=O.COC(O)=O Chemical class CCCCOC(OC)=O.COC(O)=O DZAHXNNEQCZPGJ-UHFFFAOYSA-N 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
• 239000012044 organic layer Substances 0.000 description 15
• 210000004027 cell Anatomy 0.000 description 14
• 230000006837 decompression Effects 0.000 description 14
• 229940079593 drug Drugs 0.000 description 14
• NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 13
• 239000003054 catalyst Substances 0.000 description 13
• 235000019439 ethyl acetate Nutrition 0.000 description 13
• 239000010410 layer Substances 0.000 description 13
• 150000002825 nitriles Chemical class 0.000 description 13
• 238000001556 precipitation Methods 0.000 description 13
• 238000003786 synthesis reaction Methods 0.000 description 13
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 12
• 239000007924 injection Substances 0.000 description 12
• 238000002347 injection Methods 0.000 description 12
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 12
• 238000010992 reflux Methods 0.000 description 11
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 10
• PEAOEIWYQVXZMB-UHFFFAOYSA-N 5-bromo-2-chloropyridine Chemical compound ClC1=CC=C(Br)C=N1 PEAOEIWYQVXZMB-UHFFFAOYSA-N 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 10
• 125000003118 aryl group Chemical group 0.000 description 10
• 150000001721 carbon Chemical group 0.000 description 10
• 239000003153 chemical reaction reagent Substances 0.000 description 10
• 125000004122 cyclic group Chemical group 0.000 description 10
• 238000010790 dilution Methods 0.000 description 10
• 239000012895 dilution Substances 0.000 description 10
• 229960002715 nicotine Drugs 0.000 description 10
• 230000001242 postsynaptic effect Effects 0.000 description 10
• 238000001953 recrystallisation Methods 0.000 description 10
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 10
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 9
• 238000002425 crystallisation Methods 0.000 description 9
• 230000008025 crystallization Effects 0.000 description 9
• 238000002474 experimental method Methods 0.000 description 9
• 229910052740 iodine Inorganic materials 0.000 description 9
• 239000011630 iodine Substances 0.000 description 9
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 9
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 9
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 9
• 229960001866 silicon dioxide Drugs 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
• 238000001311 chemical methods and process Methods 0.000 description 8
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 230000001537 neural effect Effects 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 230000008569 process Effects 0.000 description 8
• 210000000225 synapse Anatomy 0.000 description 8
• KSCPLKVBWDOSAI-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCCC2CNCC21 KSCPLKVBWDOSAI-UHFFFAOYSA-N 0.000 description 7
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
• 239000000730 antalgic agent Substances 0.000 description 7
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 239000002502 liposome Substances 0.000 description 7
• 239000012280 lithium aluminium hydride Substances 0.000 description 7
• 239000012528 membrane Substances 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 238000000926 separation method Methods 0.000 description 7
• FQJRZOYTUCCBQR-UHFFFAOYSA-N tert-butyl 2-methylheptanoate Chemical compound CCCCCC(C)C(=O)OC(C)(C)C FQJRZOYTUCCBQR-UHFFFAOYSA-N 0.000 description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 239000004215 Carbon black (E152) Substances 0.000 description 6
• CTENFNNZBMHDDG-UHFFFAOYSA-N Dopamine hydrochloride Chemical compound Cl.NCCC1=CC=C(O)C(O)=C1 CTENFNNZBMHDDG-UHFFFAOYSA-N 0.000 description 6
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 238000002441 X-ray diffraction Methods 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 125000000623 heterocyclic group Chemical group 0.000 description 6
• 229930195733 hydrocarbon Natural products 0.000 description 6
• 150000002430 hydrocarbons Chemical class 0.000 description 6
• GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 6
• FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 6
• OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 6
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
• 102000005962 receptors Human genes 0.000 description 6
• 108020003175 receptors Proteins 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• 230000001225 therapeutic effect Effects 0.000 description 6
• 239000003981 vehicle Substances 0.000 description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
• 108091006146 Channels Proteins 0.000 description 5
• 206010012289 Dementia Diseases 0.000 description 5
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
• 241000700159 Rattus Species 0.000 description 5
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 230000031018 biological processes and functions Effects 0.000 description 5
• 230000005540 biological transmission Effects 0.000 description 5
• 210000004556 brain Anatomy 0.000 description 5
• 239000013078 crystal Substances 0.000 description 5
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
• 239000012065 filter cake Substances 0.000 description 5
• 238000011010 flushing procedure Methods 0.000 description 5
• 239000006260 foam Substances 0.000 description 5
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
• 150000002500 ions Chemical class 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• 235000012239 silicon dioxide Nutrition 0.000 description 5
• 229960002317 succinimide Drugs 0.000 description 5
• OEQJOYQHIGIVTN-UHFFFAOYSA-N tert-butyl nonanoate Chemical compound CCCCCCCCC(=O)OC(C)(C)C OEQJOYQHIGIVTN-UHFFFAOYSA-N 0.000 description 5
• OSANFONRYANBRD-WLHGVMLRSA-N (e)-but-2-enedioic acid;octane Chemical compound CCCCCCCC.OC(=O)\C=C\C(O)=O OSANFONRYANBRD-WLHGVMLRSA-N 0.000 description 4
• IJVGODUTGYOVKR-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,2-b]pyridine Chemical compound N1CCCC2NCCC21 IJVGODUTGYOVKR-UHFFFAOYSA-N 0.000 description 4
• JMWPSCUIQIMVQH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,4-c]pyridine Chemical compound C1NCCC2CNCC21 JMWPSCUIQIMVQH-UHFFFAOYSA-N 0.000 description 4
• 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 4
• YTSKHJMMNFPBBZ-UHFFFAOYSA-N 5-bromo-2-chloro-3-methylpyridine Chemical compound CC1=CC(Br)=CN=C1Cl YTSKHJMMNFPBBZ-UHFFFAOYSA-N 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 4
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 150000001414 amino alcohols Chemical class 0.000 description 4
• 239000012298 atmosphere Substances 0.000 description 4
• 150000003851 azoles Chemical class 0.000 description 4
• 230000027455 binding Effects 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 230000001713 cholinergic effect Effects 0.000 description 4
• 238000013016 damping Methods 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 239000000284 extract Substances 0.000 description 4
• 239000012530 fluid Substances 0.000 description 4
• 235000019253 formic acid Nutrition 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• 150000004678 hydrides Chemical class 0.000 description 4
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 238000007912 intraperitoneal administration Methods 0.000 description 4
• 230000014759 maintenance of location Effects 0.000 description 4
• 229960002510 mandelic acid Drugs 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 238000006386 neutralization reaction Methods 0.000 description 4
• 229940127240 opiate Drugs 0.000 description 4
• 230000035699 permeability Effects 0.000 description 4
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
• 230000003518 presynaptic effect Effects 0.000 description 4
• 239000000377 silicon dioxide Substances 0.000 description 4
• 201000009032 substance abuse Diseases 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
• 239000000080 wetting agent Substances 0.000 description 4
• QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 3
• LATHDVDCFBYVBB-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[2,3-c]pyridine Chemical compound C1CNCC2NCCC21 LATHDVDCFBYVBB-UHFFFAOYSA-N 0.000 description 3
• UWQVPLPJLRBXRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,2-c]pyridine Chemical compound C1NCCC2NCCC21 UWQVPLPJLRBXRH-UHFFFAOYSA-N 0.000 description 3
• SSNMISUJOQAFRR-UHFFFAOYSA-N 2,6-naphthyridine Chemical class N1=CC=C2C=NC=CC2=C1 SSNMISUJOQAFRR-UHFFFAOYSA-N 0.000 description 3
• FZWUIWQMJFAWJW-UHFFFAOYSA-N 3-bromo-5-methoxypyridine Chemical compound COC1=CN=CC(Br)=C1 FZWUIWQMJFAWJW-UHFFFAOYSA-N 0.000 description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
• FTFFHWWIPOQCBC-UHFFFAOYSA-N 5-bromopyridine-3-carbonitrile Chemical compound BrC1=CN=CC(C#N)=C1 FTFFHWWIPOQCBC-UHFFFAOYSA-N 0.000 description 3
• 208000030507 AIDS Diseases 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• 208000019901 Anxiety disease Diseases 0.000 description 3
• 101100477360 Arabidopsis thaliana IPSP gene Proteins 0.000 description 3
• 102000009660 Cholinergic Receptors Human genes 0.000 description 3
• 108010009685 Cholinergic Receptors Proteins 0.000 description 3
• 208000030814 Eating disease Diseases 0.000 description 3
• 208000019454 Feeding and Eating disease Diseases 0.000 description 3
• 206010016825 Flushing Diseases 0.000 description 3
• KOTOUBGHZHWCCJ-UHFFFAOYSA-N IPSP Chemical compound CCS(=O)CSP(=S)(OC(C)C)OC(C)C KOTOUBGHZHWCCJ-UHFFFAOYSA-N 0.000 description 3
• 206010061218 Inflammation Diseases 0.000 description 3
• 206010026749 Mania Diseases 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 208000019695 Migraine disease Diseases 0.000 description 3
• 241000237502 Ostreidae Species 0.000 description 3
• 206010036618 Premenstrual syndrome Diseases 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 206010046543 Urinary incontinence Diseases 0.000 description 3
• 208000027418 Wounds and injury Diseases 0.000 description 3
• 235000010443 alginic acid Nutrition 0.000 description 3
• 229920000615 alginic acid Polymers 0.000 description 3
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 230000008859 change Effects 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 239000004567 concrete Substances 0.000 description 3
• 235000014632 disordered eating Nutrition 0.000 description 3
• 239000003995 emulsifying agent Substances 0.000 description 3
• 206010015037 epilepsy Diseases 0.000 description 3
• 238000003818 flash chromatography Methods 0.000 description 3
• 229960002870 gabapentin Drugs 0.000 description 3
• 235000011187 glycerol Nutrition 0.000 description 3
• 230000036541 health Effects 0.000 description 3
• 230000004054 inflammatory process Effects 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 150000002632 lipids Chemical class 0.000 description 3
• 230000033001 locomotion Effects 0.000 description 3
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
• 235000019341 magnesium sulphate Nutrition 0.000 description 3
• 239000011159 matrix material Substances 0.000 description 3
• 230000007074 memory dysfunction Effects 0.000 description 3
• 206010027599 migraine Diseases 0.000 description 3
• 229960005181 morphine Drugs 0.000 description 3
• 150000005054 naphthyridines Chemical class 0.000 description 3
• 230000004770 neurodegeneration Effects 0.000 description 3
• 230000000324 neuroprotective effect Effects 0.000 description 3
• 231100000956 nontoxicity Toxicity 0.000 description 3
• 125000000160 oxazolidinyl group Chemical group 0.000 description 3
• 235000020636 oyster Nutrition 0.000 description 3
• 230000000144 pharmacologic effect Effects 0.000 description 3
• 239000006187 pill Substances 0.000 description 3
• 230000001737 promoting effect Effects 0.000 description 3
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 3
• 125000004076 pyridyl group Chemical group 0.000 description 3
• 150000003233 pyrroles Chemical class 0.000 description 3
• 210000000664 rectum Anatomy 0.000 description 3
• 238000011160 research Methods 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 230000007958 sleep Effects 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
• 235000017550 sodium carbonate Nutrition 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• 231100000736 substance abuse Toxicity 0.000 description 3
• 208000011117 substance-related disease Diseases 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• UWNNZXDNLPNGQJ-UHFFFAOYSA-N tert-butyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(C)(C)C UWNNZXDNLPNGQJ-UHFFFAOYSA-N 0.000 description 3
• UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
• 229910052727 yttrium Inorganic materials 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 2
• JZAWBDIRCFFJBI-UHFFFAOYSA-N 2-(4-oxocyclohexyl)acetic acid Chemical compound OC(=O)CC1CCC(=O)CC1 JZAWBDIRCFFJBI-UHFFFAOYSA-N 0.000 description 2
• OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
• GGRLKHMFMUXIOG-UHFFFAOYSA-M 2-acetyloxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CC(=O)OCC[N+](C)(C)C GGRLKHMFMUXIOG-UHFFFAOYSA-M 0.000 description 2
• IMYYCZADDHYKLF-UHFFFAOYSA-N 2-azaniumyl-2-(4-hydroxycyclohexyl)acetate Chemical compound OC(=O)C(N)C1CCC(O)CC1 IMYYCZADDHYKLF-UHFFFAOYSA-N 0.000 description 2
• WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 description 2
• FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• 206010001497 Agitation Diseases 0.000 description 2
• 108010087765 Antipain Proteins 0.000 description 2
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• RPMDJTWHVFWJGQ-UHFFFAOYSA-N Cl.C(C)(C)(C)OC(C=C)=O Chemical compound Cl.C(C)(C)(C)OC(C=C)=O RPMDJTWHVFWJGQ-UHFFFAOYSA-N 0.000 description 2
• TZULSCLUWZPFLT-VWXHXBRYSA-N Cl.Cl.C([C@@H]1CCN[C@@H]1C1)CN1C1=CC=CN=C1 Chemical compound Cl.Cl.C([C@@H]1CCN[C@@H]1C1)CN1C1=CC=CN=C1 TZULSCLUWZPFLT-VWXHXBRYSA-N 0.000 description 2
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
• 241000557626 Corvus corax Species 0.000 description 2
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
• ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical class N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• 102000004190 Enzymes Human genes 0.000 description 2
• 108090000790 Enzymes Proteins 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 241000206672 Gelidium Species 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 244000061176 Nicotiana tabacum Species 0.000 description 2
• 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
• 241000336896 Numata Species 0.000 description 2
• 239000008896 Opium Substances 0.000 description 2
• 101150003085 Pdcl gene Proteins 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• 102000004659 Presynaptic Receptors Human genes 0.000 description 2
• 108010003717 Presynaptic Receptors Proteins 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• 239000005864 Sulphur Substances 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
• 229960004373 acetylcholine Drugs 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 230000036982 action potential Effects 0.000 description 2
• 235000010419 agar Nutrition 0.000 description 2
• 229940072056 alginate Drugs 0.000 description 2
• 150000001336 alkenes Chemical class 0.000 description 2
• 150000001345 alkine derivatives Chemical class 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• 238000005804 alkylation reaction Methods 0.000 description 2
• 230000005260 alpha ray Effects 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 230000036592 analgesia Effects 0.000 description 2
• 230000000202 analgesic effect Effects 0.000 description 2
• SDNYTAYICBFYFH-TUFLPTIASA-N antipain Chemical compound NC(N)=NCCC[C@@H](C=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 SDNYTAYICBFYFH-TUFLPTIASA-N 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 2
• CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• 235000012216 bentonite Nutrition 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
• 239000004327 boric acid Substances 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 208000015114 central nervous system disease Diseases 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 238000011097 chromatography purification Methods 0.000 description 2
• 235000009508 confectionery Nutrition 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 238000002447 crystallographic data Methods 0.000 description 2
• 125000000753 cycloalkyl group Chemical group 0.000 description 2
• 230000006378 damage Effects 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
• 230000000857 drug effect Effects 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 125000004494 ethyl ester group Chemical group 0.000 description 2
• 239000008098 formaldehyde solution Substances 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 239000000413 hydrolysate Substances 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 238000005462 in vivo assay Methods 0.000 description 2
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 2
• 239000003701 inert diluent Substances 0.000 description 2
• 230000002757 inflammatory effect Effects 0.000 description 2
• 208000014674 injury Diseases 0.000 description 2
• 125000005956 isoquinolyl group Chemical group 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• 239000008297 liquid dosage form Substances 0.000 description 2
• 239000006210 lotion Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
• 239000003094 microcapsule Substances 0.000 description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 210000001640 nerve ending Anatomy 0.000 description 2
• 230000003957 neurotransmitter release Effects 0.000 description 2
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• 229960001027 opium Drugs 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 210000002220 organoid Anatomy 0.000 description 2
• 125000001979 organolithium group Chemical group 0.000 description 2
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 235000015320 potassium carbonate Nutrition 0.000 description 2
• AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 2
• 229960001233 pregabalin Drugs 0.000 description 2
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 235000019633 pungent taste Nutrition 0.000 description 2
• 238000010926 purge Methods 0.000 description 2
• KAYMJTJKPNRIHC-UHFFFAOYSA-N pyrrolo[2,3-c]azepine Chemical compound C1=CN=CC2=NC=CC2=C1 KAYMJTJKPNRIHC-UHFFFAOYSA-N 0.000 description 2
• FDVAFZGRSKEVGR-UHFFFAOYSA-N pyrrolo[2,3-d]azepine Chemical compound C1=NC=CC2=NC=CC2=C1 FDVAFZGRSKEVGR-UHFFFAOYSA-N 0.000 description 2
• 239000000376 reactant Substances 0.000 description 2
• 239000000018 receptor agonist Substances 0.000 description 2
• 229940044601 receptor agonist Drugs 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 210000002027 skeletal muscle Anatomy 0.000 description 2
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 239000012453 solvate Chemical group 0.000 description 2
• 239000000600 sorbitol Substances 0.000 description 2
• 235000014347 soups Nutrition 0.000 description 2
• 230000000638 stimulation Effects 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 2
• 229940124530 sulfonamide Drugs 0.000 description 2
• 238000006277 sulfonation reaction Methods 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 210000002182 synaptic membrane Anatomy 0.000 description 2
• RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 2
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• 238000012546 transfer Methods 0.000 description 2
• 230000009466 transformation Effects 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 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 2
• RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
• 238000009834 vaporization Methods 0.000 description 2
• 230000008016 vaporization Effects 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 1
• LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
• RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
• RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
• MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
• JLDHXHPQMBNKMC-BQBZGAKWSA-N (2s,3s)-3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC[C@H](O)[C@H]1C(O)=O JLDHXHPQMBNKMC-BQBZGAKWSA-N 0.000 description 1
• MXQPYUGJHDHNBG-DTORHVGOSA-N (3ar,6as)-5-(5-fluoropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical class FC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 MXQPYUGJHDHNBG-DTORHVGOSA-N 0.000 description 1
• FISPSGRYTNKFIR-PHIMTYICSA-N (3ar,6as)-5-(6-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical class C1=NC(C)=CC=C1N1C[C@H]2CNC[C@H]2C1 FISPSGRYTNKFIR-PHIMTYICSA-N 0.000 description 1
• RWSWISZCTDWWBO-VXGBXAGGSA-N (3ar,7ar)-4-(5-fluoropyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound FC1=CN=CC(N2[C@@H]3CCN[C@@H]3CCC2)=C1 RWSWISZCTDWWBO-VXGBXAGGSA-N 0.000 description 1
• IIOLSYQMSNRKBK-GHMZBOCLSA-N (3ar,7ar)-4-(6-chloro-5-fluoropyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound N1=C(Cl)C(F)=CC(N2[C@@H]3CCN[C@@H]3CCC2)=C1 IIOLSYQMSNRKBK-GHMZBOCLSA-N 0.000 description 1
• XPLNLPRRNKYWAZ-VXGBXAGGSA-N (3ar,7ar)-4-(6-chloro-5-methylpyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound N1=C(Cl)C(C)=CC(N2[C@@H]3CCN[C@@H]3CCC2)=C1 XPLNLPRRNKYWAZ-VXGBXAGGSA-N 0.000 description 1
• SISOZSQETXBELK-GHMZBOCLSA-N (3ar,7ar)-4-(6-chloropyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CCN[C@@H]2CCC1 SISOZSQETXBELK-GHMZBOCLSA-N 0.000 description 1
• GWQBVFJNCPLJTI-CHWSQXEVSA-N (3ar,7ar)-4-(6-methylpyridin-3-yl)-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound C1=NC(C)=CC=C1N1[C@@H]2CCN[C@@H]2CCC1 GWQBVFJNCPLJTI-CHWSQXEVSA-N 0.000 description 1
• MSGSLDBBIVJNAI-VXGBXAGGSA-N (3ar,7ar)-4-pyridin-3-yl-1,2,3,3a,5,6,7,7a-octahydropyrrolo[3,2-b]pyridine Chemical compound C([C@@H]1[C@H]2CCN1)CCN2C1=CC=CN=C1 MSGSLDBBIVJNAI-VXGBXAGGSA-N 0.000 description 1
• NTMCUPPKVJWWSP-ZWNOBZJWSA-N (3ar,8as)-7-(5-fluoropyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound FC1=CN=CC(N2C[C@H]3NCC[C@H]3CCC2)=C1 NTMCUPPKVJWWSP-ZWNOBZJWSA-N 0.000 description 1
• PYYGTBIEVCBRAC-BXKDBHETSA-N (3ar,8as)-7-(6-chloro-5-fluoropyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound N1=C(Cl)C(F)=CC(N2C[C@H]3NCC[C@H]3CCC2)=C1 PYYGTBIEVCBRAC-BXKDBHETSA-N 0.000 description 1
• HHZXLUJZWCPALE-DGCLKSJQSA-N (3ar,8as)-7-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3CCC2)=C1 HHZXLUJZWCPALE-DGCLKSJQSA-N 0.000 description 1
• UCKZTIZEMVTGGU-ZYHUDNBSSA-N (3ar,8as)-7-(6-chloropyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2CCC1 UCKZTIZEMVTGGU-ZYHUDNBSSA-N 0.000 description 1
• FYGMDRKVDIHRGZ-TZMCWYRMSA-N (3ar,8as)-7-(6-methylpyridin-3-yl)-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound C1=NC(C)=CC=C1N1C[C@H]2NCC[C@H]2CCC1 FYGMDRKVDIHRGZ-TZMCWYRMSA-N 0.000 description 1
• MZYLXNDLYJNWNL-DGCLKSJQSA-N (3ar,8as)-7-pyridin-3-yl-2,3,3a,4,5,6,8,8a-octahydro-1h-pyrrolo[2,3-c]azepine Chemical compound C([C@@H]1CCN[C@@H]1C1)CCN1C1=CC=CN=C1 MZYLXNDLYJNWNL-DGCLKSJQSA-N 0.000 description 1
• GSMPEMQHEGWOHE-JOYOIKCWSA-N (3as,7ar)-5-(5-fluoropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound FC1=CN=CC(N2C[C@@H]3CCN[C@@H]3CC2)=C1 GSMPEMQHEGWOHE-JOYOIKCWSA-N 0.000 description 1
• DVWMQQLOIAODGU-UWVGGRQHSA-N (3as,7ar)-5-(5-fluoropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound FC1=CN=CC(N2C[C@@H]3CNC[C@@H]3CC2)=C1 DVWMQQLOIAODGU-UWVGGRQHSA-N 0.000 description 1
• WSYFMYKZOLWLSD-GZMMTYOYSA-N (3as,7ar)-5-(6-chloro-5-fluoropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound N1=C(Cl)C(F)=CC(N2C[C@@H]3CCN[C@@H]3CC2)=C1 WSYFMYKZOLWLSD-GZMMTYOYSA-N 0.000 description 1
• DHYKAKGWYYCJMC-IUCAKERBSA-N (3as,7ar)-5-(6-chloro-5-fluoropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound N1=C(Cl)C(F)=CC(N2C[C@@H]3CNC[C@@H]3CC2)=C1 DHYKAKGWYYCJMC-IUCAKERBSA-N 0.000 description 1
• VAVFCDBRWCRUOC-CMPLNLGQSA-N (3as,7ar)-5-(6-chloro-5-methylpyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3CCN[C@@H]3CC2)=C1 VAVFCDBRWCRUOC-CMPLNLGQSA-N 0.000 description 1
• QYRBHWSSAMDGHP-QWRGUYRKSA-N (3as,7ar)-5-(6-chloro-5-methylpyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3CNC[C@@H]3CC2)=C1 QYRBHWSSAMDGHP-QWRGUYRKSA-N 0.000 description 1
• DVKQABJHRNBSDE-GXSJLCMTSA-N (3as,7ar)-5-(6-chloropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2CCN[C@@H]2CC1 DVKQABJHRNBSDE-GXSJLCMTSA-N 0.000 description 1
• ANLNMDONIHDNAT-UWVGGRQHSA-N (3as,7ar)-5-(6-chloropyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2CNC[C@@H]2CC1 ANLNMDONIHDNAT-UWVGGRQHSA-N 0.000 description 1
• LNBVLMANTHIXBV-WCQYABFASA-N (3as,7ar)-5-(6-methylpyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound C1=NC(C)=CC=C1N1C[C@@H]2CCN[C@@H]2CC1 LNBVLMANTHIXBV-WCQYABFASA-N 0.000 description 1
• MPBWQGNSOFEQIN-RYUDHWBXSA-N (3as,7ar)-5-(6-methylpyridin-3-yl)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound C1=NC(C)=CC=C1N1C[C@@H]2CNC[C@@H]2CC1 MPBWQGNSOFEQIN-RYUDHWBXSA-N 0.000 description 1
• SRIQRGIGQGVSLC-CMPLNLGQSA-N (3as,7ar)-5-pyridin-3-yl-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridine Chemical compound C([C@@H]1CCN[C@@H]1CC1)N1C1=CC=CN=C1 SRIQRGIGQGVSLC-CMPLNLGQSA-N 0.000 description 1
• LVTBJDSIVXNLOV-QWRGUYRKSA-N (3as,7ar)-5-pyridin-3-yl-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound C([C@@H]1CNC[C@@H]1CC1)N1C1=CC=CN=C1 LVTBJDSIVXNLOV-QWRGUYRKSA-N 0.000 description 1
• UNSSLKPFSTVODC-GXFFZTMASA-N (3as,8ar)-6-(5-fluoropyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound FC1=CN=CC(N2CC[C@H]3NCC[C@H]3CC2)=C1 UNSSLKPFSTVODC-GXFFZTMASA-N 0.000 description 1
• BZFNONWLZJYWAQ-JOYOIKCWSA-N (3as,8ar)-6-(6-chloro-5-fluoropyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound N1=C(Cl)C(F)=CC(N2CC[C@H]3NCC[C@H]3CC2)=C1 BZFNONWLZJYWAQ-JOYOIKCWSA-N 0.000 description 1
• UKPNNHOZLBQFDV-WCQYABFASA-N (3as,8ar)-6-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound N1=C(Cl)C(C)=CC(N2CC[C@H]3NCC[C@H]3CC2)=C1 UKPNNHOZLBQFDV-WCQYABFASA-N 0.000 description 1
• WWZXCKXCPNFNPS-CMPLNLGQSA-N (3as,8ar)-6-(6-chloropyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound C1=NC(Cl)=CC=C1N1CC[C@H]2NCC[C@H]2CC1 WWZXCKXCPNFNPS-CMPLNLGQSA-N 0.000 description 1
• ISCKSCKSRNGERF-GXTWGEPZSA-N (3as,8ar)-6-(6-methylpyridin-3-yl)-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound C1=NC(C)=CC=C1N1CC[C@H]2NCC[C@H]2CC1 ISCKSCKSRNGERF-GXTWGEPZSA-N 0.000 description 1
• DNYVCGHKEGTDNQ-WCQYABFASA-N (3as,8ar)-6-pyridin-3-yl-2,3,3a,4,5,7,8,8a-octahydro-1h-pyrrolo[2,3-d]azepine Chemical compound C([C@@H]1CCN[C@@H]1CC1)CN1C1=CC=CN=C1 DNYVCGHKEGTDNQ-WCQYABFASA-N 0.000 description 1
• PYXNQNJNAGBBCK-SKDRFNHKSA-N (4ar,7ar)-1-(5-fluoropyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound FC1=CN=CC(N2[C@H]3CNC[C@H]3CCC2)=C1 PYXNQNJNAGBBCK-SKDRFNHKSA-N 0.000 description 1
• ZJMVACHVQVNKOA-KCJUWKMLSA-N (4ar,7ar)-1-(6-chloro-5-fluoropyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound N1=C(Cl)C(F)=CC(N2[C@H]3CNC[C@H]3CCC2)=C1 ZJMVACHVQVNKOA-KCJUWKMLSA-N 0.000 description 1
• VDDGZOKRYUPHEA-PWSUYJOCSA-N (4ar,7ar)-1-(6-chloro-5-methylpyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound N1=C(Cl)C(C)=CC(N2[C@H]3CNC[C@H]3CCC2)=C1 VDDGZOKRYUPHEA-PWSUYJOCSA-N 0.000 description 1
• XKBATZFRVPAUPF-KOLCDFICSA-N (4ar,7ar)-1-(6-chloropyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2CCC1 XKBATZFRVPAUPF-KOLCDFICSA-N 0.000 description 1
• XQTPMJANKMYKPS-YPMHNXCESA-N (4ar,7ar)-1-(6-methylpyridin-3-yl)-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1=NC(C)=CC=C1N1[C@H]2CNC[C@H]2CCC1 XQTPMJANKMYKPS-YPMHNXCESA-N 0.000 description 1
• MFHAOMBSDYEWTK-PWSUYJOCSA-N (4ar,7ar)-1-pyridin-3-yl-2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C([C@H]1[C@@H]2CNC1)CCN2C1=CC=CN=C1 MFHAOMBSDYEWTK-PWSUYJOCSA-N 0.000 description 1
• IWYDHOAUDWTVEP-SSDOTTSWSA-M (R)-mandelate Chemical compound [O-]C(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-M 0.000 description 1
• IWYDHOAUDWTVEP-ZETCQYMHSA-M (S)-mandelate Chemical compound [O-]C(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-M 0.000 description 1
• 229930182840 (S)-nicotine Natural products 0.000 description 1
• GVRWIAHBVAYKIZ-FNORWQNLSA-N (e)-dec-3-ene Chemical compound CCCCCC\C=C\CC GVRWIAHBVAYKIZ-FNORWQNLSA-N 0.000 description 1
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
• FTUSZJTUFHXUPG-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydropyrrolo[2,3-c]pyrrole Chemical class C1NC=C2NCCC21 FTUSZJTUFHXUPG-UHFFFAOYSA-N 0.000 description 1
• HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical compound C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 description 1
• HWUGBMMPIAIJJC-UHFFFAOYSA-N 1,2,3,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole Chemical class N1CC2CNCC2=C1 HWUGBMMPIAIJJC-UHFFFAOYSA-N 0.000 description 1
• MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 1
• CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 description 1
• VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical class C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 description 1
• MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
• CZSGAUHCBIGJQA-UHFFFAOYSA-N 1-benzyl-3-oxopiperidine-4-carboxylic acid Chemical compound C1C(=O)C(C(=O)O)CCN1CC1=CC=CC=C1 CZSGAUHCBIGJQA-UHFFFAOYSA-N 0.000 description 1
• VNBFUGOVQMFIRN-UHFFFAOYSA-N 1-chlorobutan-2-ol Chemical compound CCC(O)CCl VNBFUGOVQMFIRN-UHFFFAOYSA-N 0.000 description 1
• VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• XLKDJOPOOHHZAN-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine Chemical compound C1=NC=C2NC=CC2=C1 XLKDJOPOOHHZAN-UHFFFAOYSA-N 0.000 description 1
• SRSKXJVMVSSSHB-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine Chemical compound N1=CC=C2NC=CC2=C1 SRSKXJVMVSSSHB-UHFFFAOYSA-N 0.000 description 1
• QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 1
• ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
• BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
• WBIYGACFBGCOKV-PWSUYJOCSA-N 2-[5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-2-bromopyridin-3-yl]acetonitrile Chemical class C1=C(CC#N)C(Br)=NC=C1N1C[C@@H]2NCC[C@@H]2C1 WBIYGACFBGCOKV-PWSUYJOCSA-N 0.000 description 1
• 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
• JHARVUVBTAAPLA-UHFFFAOYSA-N 2-chloro-4-methyl-3-nitropyridine Chemical compound CC1=CC=NC(Cl)=C1[N+]([O-])=O JHARVUVBTAAPLA-UHFFFAOYSA-N 0.000 description 1
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
• 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
• 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
• UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
• SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 description 1
• LQOBMKYCRQDMTN-UHFFFAOYSA-N 3-(2-ethylphenyl)pentan-3-amine;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1C(N)(CC)CC LQOBMKYCRQDMTN-UHFFFAOYSA-N 0.000 description 1
• FYUMRYNAZSTXJV-UHFFFAOYSA-N 3-bromo-5-ethoxypyridine Chemical compound CCOC1=CN=CC(Br)=C1 FYUMRYNAZSTXJV-UHFFFAOYSA-N 0.000 description 1
• YSHKYZAWTWKQKK-UHFFFAOYSA-N 3-bromo-5-phenylmethoxypyridine Chemical compound BrC1=CN=CC(OCC=2C=CC=CC=2)=C1 YSHKYZAWTWKQKK-UHFFFAOYSA-N 0.000 description 1
• RPZVZCUMJDFFTE-UHFFFAOYSA-N 3-bromo-5-propoxypyridine Chemical compound CCCOC1=CN=CC(Br)=C1 RPZVZCUMJDFFTE-UHFFFAOYSA-N 0.000 description 1
• ZGIKWINFUGEQEO-UHFFFAOYSA-N 3-bromoquinoline Chemical compound C1=CC=CC2=CC(Br)=CN=C21 ZGIKWINFUGEQEO-UHFFFAOYSA-N 0.000 description 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
• 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
• GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 1
• WEDKTMOIKOKBSH-UHFFFAOYSA-N 4,5-dihydrothiadiazole Chemical compound C1CN=NS1 WEDKTMOIKOKBSH-UHFFFAOYSA-N 0.000 description 1
• LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 1
• IBKMZYWDWWIWEL-UHFFFAOYSA-N 4-methylpyridin-3-amine Chemical compound CC1=CC=NC=C1N IBKMZYWDWWIWEL-UHFFFAOYSA-N 0.000 description 1
• JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
• GFJMOZYIDADKLJ-UHFFFAOYSA-N 5-bromo-2-chloro-3-methoxypyridine Chemical compound COC1=CC(Br)=CN=C1Cl GFJMOZYIDADKLJ-UHFFFAOYSA-N 0.000 description 1
• HXPMRPRBABWPKL-UHFFFAOYSA-N 5-bromo-3-methyl-1h-pyridin-2-one Chemical compound CC1=CC(Br)=CN=C1O HXPMRPRBABWPKL-UHFFFAOYSA-N 0.000 description 1
• KBLGGRWUEVCNPY-UHFFFAOYSA-N 5-bromo-3-methylpyridin-2-amine Chemical compound CC1=CC(Br)=CN=C1N KBLGGRWUEVCNPY-UHFFFAOYSA-N 0.000 description 1
• WZASNGSXCLIJCD-UHFFFAOYSA-N 5-bromo-4H-pyridin-3-one Chemical compound BrC1=CN=CC(C1)=O WZASNGSXCLIJCD-UHFFFAOYSA-N 0.000 description 1
• 125000006043 5-hexenyl group Chemical group 0.000 description 1
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
• PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
• 206010000087 Abdominal pain upper Diseases 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 235000006491 Acacia senegal Nutrition 0.000 description 1
• 208000007848 Alcoholism Diseases 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 206010002198 Anaphylactic reaction Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 102000007527 Autoreceptors Human genes 0.000 description 1
• 108010071131 Autoreceptors Proteins 0.000 description 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
• KVMMLUBIRJIEHK-UHFFFAOYSA-N BrC1=CC(C(N=C1)Cl)=O Chemical compound BrC1=CC(C(N=C1)Cl)=O KVMMLUBIRJIEHK-UHFFFAOYSA-N 0.000 description 1
• AZQBPXDZPZPTQP-VXGBXAGGSA-N C([C@H]1CCNC[C@H]1CC1)N1C1=CC=CN=C1 Chemical class C([C@H]1CCNC[C@H]1CC1)N1C1=CC=CN=C1 AZQBPXDZPZPTQP-VXGBXAGGSA-N 0.000 description 1
• YTJLRSUNQSRYPV-PWSUYJOCSA-N C1=NC(C)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 Chemical class C1=NC(C)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 YTJLRSUNQSRYPV-PWSUYJOCSA-N 0.000 description 1
• TZSDAJRMFREETH-CHWSQXEVSA-N C1=NC(C)=CC=C1N1C[C@H]2CCNC[C@H]2CC1 Chemical class C1=NC(C)=CC=C1N1C[C@H]2CCNC[C@H]2CC1 TZSDAJRMFREETH-CHWSQXEVSA-N 0.000 description 1
• VEKXUTMWUGWABO-WCQYABFASA-N C1=NC(C)=CC=C1N1C[C@H]2NCC[C@H]2CC1 Chemical compound C1=NC(C)=CC=C1N1C[C@H]2NCC[C@H]2CC1 VEKXUTMWUGWABO-WCQYABFASA-N 0.000 description 1
• RRSWMWSQRRLIIS-PWSUYJOCSA-N C1=NC(C)=CC=C1N1[C@H]2CNC[C@H]2CC1 Chemical class C1=NC(C)=CC=C1N1[C@H]2CNC[C@H]2CC1 RRSWMWSQRRLIIS-PWSUYJOCSA-N 0.000 description 1
• LOAOMRSCWAUOLL-GHMZBOCLSA-N C1=NC(Cl)=CC=C1N1C[C@H]2CCNC[C@H]2CC1 Chemical class C1=NC(Cl)=CC=C1N1C[C@H]2CCNC[C@H]2CC1 LOAOMRSCWAUOLL-GHMZBOCLSA-N 0.000 description 1
• BVFIBUJCNCDDNR-GXSJLCMTSA-N C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2CC1 Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2NCC[C@H]2CC1 BVFIBUJCNCDDNR-GXSJLCMTSA-N 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 241001111317 Chondrodendron tomentosum Species 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 206010011224 Cough Diseases 0.000 description 1
• 239000008709 Curare Substances 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 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
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
• 206010052804 Drug tolerance Diseases 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 208000004232 Enteritis Diseases 0.000 description 1
• KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 1
• KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
• YHDUAHJZENXNEP-KCJUWKMLSA-N FC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 Chemical class FC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 YHDUAHJZENXNEP-KCJUWKMLSA-N 0.000 description 1
• QCSLHKBLBSQXIY-GHMZBOCLSA-N FC1=CN=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 Chemical class FC1=CN=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 QCSLHKBLBSQXIY-GHMZBOCLSA-N 0.000 description 1
• JUXGUNVOLPMFNG-JOYOIKCWSA-N FC1=CN=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 Chemical compound FC1=CN=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 JUXGUNVOLPMFNG-JOYOIKCWSA-N 0.000 description 1
• RINRLWOMLQDAEG-KCJUWKMLSA-N FC1=CN=CC(N2[C@H]3CNC[C@H]3CC2)=C1 Chemical class FC1=CN=CC(N2[C@H]3CNC[C@H]3CC2)=C1 RINRLWOMLQDAEG-KCJUWKMLSA-N 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 239000007818 Grignard reagent Substances 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
• 102000004310 Ion Channels Human genes 0.000 description 1
• 108090000862 Ion Channels Proteins 0.000 description 1
• 239000003810 Jones reagent Substances 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• 241000337544 Limnoriidae Species 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
• VKHOXRYUAOQHRN-VXGBXAGGSA-N N1=C(Cl)C(C)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 Chemical class N1=C(Cl)C(C)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 VKHOXRYUAOQHRN-VXGBXAGGSA-N 0.000 description 1
• FULBMGFQPTYUEV-CMPLNLGQSA-N N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 FULBMGFQPTYUEV-CMPLNLGQSA-N 0.000 description 1
• LTNVMIPLNNLUDU-KOLCDFICSA-N N1=C(Cl)C(C)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 Chemical class N1=C(Cl)C(C)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 LTNVMIPLNNLUDU-KOLCDFICSA-N 0.000 description 1
• TVLILICOWPMJEF-XCBNKYQSSA-N N1=C(Cl)C(F)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 Chemical class N1=C(Cl)C(F)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 TVLILICOWPMJEF-XCBNKYQSSA-N 0.000 description 1
• ACIIZSOLSIYIOG-NXEZZACHSA-N N1=C(Cl)C(F)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 Chemical class N1=C(Cl)C(F)=CC(N2C[C@H]3CCNC[C@H]3CC2)=C1 ACIIZSOLSIYIOG-NXEZZACHSA-N 0.000 description 1
• WFTAKVMVZVYDAD-GZMMTYOYSA-N N1=C(Cl)C(F)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 Chemical compound N1=C(Cl)C(F)=CC(N2C[C@H]3NCC[C@H]3CC2)=C1 WFTAKVMVZVYDAD-GZMMTYOYSA-N 0.000 description 1
• MBGYBSKNPANADU-XCBNKYQSSA-N N1=C(Cl)C(F)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 Chemical class N1=C(Cl)C(F)=CC(N2[C@H]3CNC[C@H]3CC2)=C1 MBGYBSKNPANADU-XCBNKYQSSA-N 0.000 description 1
• 229910019093 NaOCl Inorganic materials 0.000 description 1
• 241001274216 Naso Species 0.000 description 1
• 208000028389 Nerve injury Diseases 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
• 102000003840 Opioid Receptors Human genes 0.000 description 1
• 108090000137 Opioid Receptors Proteins 0.000 description 1
• BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 229920002230 Pectic acid Polymers 0.000 description 1
• 244000025272 Persea americana Species 0.000 description 1
• 235000008673 Persea americana Nutrition 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 229920001710 Polyorthoester Polymers 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 206010070834 Sensitisation Diseases 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 239000004141 Sodium laurylsulphate Substances 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
• 208000007107 Stomach Ulcer Diseases 0.000 description 1
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
• 208000001871 Tachycardia Diseases 0.000 description 1
• NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
• 240000006474 Theobroma bicolor Species 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 206010044565 Tremor Diseases 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
• WADIUSKZZWETGD-KCJUWKMLSA-N [5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-2-bromopyridin-3-yl]methanol Chemical compound N1=C(Br)C(CO)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 WADIUSKZZWETGD-KCJUWKMLSA-N 0.000 description 1
• DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
• ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical group CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 238000010306 acid treatment Methods 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 230000008484 agonism Effects 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
• AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
• 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 159000000013 aluminium salts Chemical class 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 229940035676 analgesics Drugs 0.000 description 1
• 230000036783 anaphylactic response Effects 0.000 description 1
• 208000003455 anaphylaxis Diseases 0.000 description 1
• 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
• 230000001430 anti-depressive effect Effects 0.000 description 1
• 229940125681 anticonvulsant agent Drugs 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 229910052728 basic metal Inorganic materials 0.000 description 1
• 150000003818 basic metals Chemical class 0.000 description 1
• 238000010009 beating Methods 0.000 description 1
• 230000006399 behavior Effects 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
• 229940050390 benzoate Drugs 0.000 description 1
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• 235000019445 benzyl alcohol Nutrition 0.000 description 1
• 229960004217 benzyl alcohol Drugs 0.000 description 1
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 230000036760 body temperature Effects 0.000 description 1
• 229910000085 borane Inorganic materials 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 0.000 description 1
• 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
• DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 229950005953 camsilate Drugs 0.000 description 1
• 125000004623 carbolinyl group Chemical group 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 150000001733 carboxylic acid esters Chemical class 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 238000005352 clarification Methods 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 229910052681 coesite Inorganic materials 0.000 description 1
• 230000003920 cognitive function Effects 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 239000002131 composite material Substances 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 230000001276 controlling effect Effects 0.000 description 1
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 238000005859 coupling reaction Methods 0.000 description 1
• 229940111134 coxibs Drugs 0.000 description 1
• 229910052906 cristobalite Inorganic materials 0.000 description 1
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
• 230000001086 cytosolic effect Effects 0.000 description 1
• 230000013872 defecation Effects 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 239000000645 desinfectant Substances 0.000 description 1
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
• 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
• WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
• LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
• 125000005594 diketone group Chemical group 0.000 description 1
• FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
• GAFRWLVTHPVQGK-UHFFFAOYSA-N dipentyl sulfate Chemical compound CCCCCOS(=O)(=O)OCCCCC GAFRWLVTHPVQGK-UHFFFAOYSA-N 0.000 description 1
• GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229960003638 dopamine Drugs 0.000 description 1
• 231100000673 dose–response relationship Toxicity 0.000 description 1
• 239000006196 drop Substances 0.000 description 1
• 239000000890 drug combination Substances 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 239000012039 electrophile Substances 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• 238000007046 ethoxylation reaction Methods 0.000 description 1
• 238000003810 ethyl acetate extraction Methods 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 230000005284 excitation Effects 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 239000003885 eye ointment Substances 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
• 235000013312 flour Nutrition 0.000 description 1
• FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
• 230000008014 freezing Effects 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 201000005917 gastric ulcer Diseases 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 210000004907 gland Anatomy 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• ZDXPYRJPNDTMRX-UHFFFAOYSA-M glutaminate Chemical compound [O-]C(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-M 0.000 description 1
• 229940075507 glyceryl monostearate Drugs 0.000 description 1
• 150000002334 glycols Chemical class 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 230000026781 habituation Effects 0.000 description 1
• 125000001475 halogen functional group Chemical group 0.000 description 1
• 210000002064 heart cell Anatomy 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 230000036571 hydration Effects 0.000 description 1
• 238000006703 hydration reaction Methods 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 230000002102 hyperpolarization Effects 0.000 description 1
• 230000002631 hypothermal effect Effects 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 230000036734 inhibitory postsynaptic potential Effects 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 229940102223 injectable solution Drugs 0.000 description 1
• 239000000976 ink Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• 125000005990 isobenzothienyl group Chemical group 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
• 238000002386 leaching Methods 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 208000024714 major depressive disease Diseases 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 238000010907 mechanical stirring Methods 0.000 description 1
• 230000028161 membrane depolarization Effects 0.000 description 1
• 230000003340 mental effect Effects 0.000 description 1
• IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 150000001457 metallic cations Chemical class 0.000 description 1
• 238000001465 metallisation Methods 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
• 239000004530 micro-emulsion Substances 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
• 230000002969 morbid Effects 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 210000000214 mouth Anatomy 0.000 description 1
• 230000002107 myocardial effect Effects 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
• RPZAAFUKDPKTKP-UHFFFAOYSA-N n-(methoxymethyl)-1-phenyl-n-(trimethylsilylmethyl)methanamine Chemical compound COCN(C[Si](C)(C)C)CC1=CC=CC=C1 RPZAAFUKDPKTKP-UHFFFAOYSA-N 0.000 description 1
• 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 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
• 230000008764 nerve damage Effects 0.000 description 1
• 239000000842 neuromuscular blocking agent Substances 0.000 description 1
• 210000002569 neuron Anatomy 0.000 description 1
• 235000005152 nicotinamide Nutrition 0.000 description 1
• 239000011570 nicotinamide Substances 0.000 description 1
• 229960003966 nicotinamide Drugs 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• UMXFLYFLTOUBPY-UHFFFAOYSA-N nitrobenzene;sulfuryl dichloride Chemical class ClS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 UMXFLYFLTOUBPY-UHFFFAOYSA-N 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 239000000820 nonprescription drug Substances 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 229940069265 ophthalmic ointment Drugs 0.000 description 1
• 210000003463 organelle Anatomy 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 239000002304 perfume Substances 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
• JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
• 150000003016 phosphoric acids Chemical class 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 150000003053 piperidines Chemical class 0.000 description 1
• 125000005936 piperidyl group Chemical group 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
• 229950010765 pivalate Drugs 0.000 description 1
• 239000002745 poly(ortho ester) Substances 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 238000007639 printing Methods 0.000 description 1
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
• 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
• 150000003180 prostaglandins Chemical class 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000000452 restraining effect Effects 0.000 description 1
• 238000007790 scraping Methods 0.000 description 1
• 150000003333 secondary alcohols Chemical class 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 230000003248 secreting effect Effects 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• 210000000582 semen Anatomy 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 230000008313 sensitization Effects 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 230000008054 signal transmission Effects 0.000 description 1
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
• 238000004088 simulation Methods 0.000 description 1
• 238000010572 single replacement reaction Methods 0.000 description 1
• 230000000391 smoking effect Effects 0.000 description 1
• 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
• AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
• 238000002791 soaking Methods 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical class [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 230000000392 somatic effect Effects 0.000 description 1
• 239000002594 sorbent Substances 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 210000000278 spinal cord Anatomy 0.000 description 1
• 238000013222 sprague-dawley male rat Methods 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 210000001562 sternum Anatomy 0.000 description 1
• 229910052682 stishovite Inorganic materials 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• AXOIZCJOOAYSMI-UHFFFAOYSA-N succinylcholine Chemical compound C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C AXOIZCJOOAYSMI-UHFFFAOYSA-N 0.000 description 1
• 229940032712 succinylcholine Drugs 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 230000006794 tachycardia Effects 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• GIIDZEBNRLNGMS-SFYZADRCSA-N tert-butyl (2r,3s)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](O)[C@H]1CO GIIDZEBNRLNGMS-SFYZADRCSA-N 0.000 description 1
• LRCPRHFAAYJMHG-RKDXNWHRSA-N tert-butyl (3s,4s)-3-amino-4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](CO)[C@H](N)C1 LRCPRHFAAYJMHG-RKDXNWHRSA-N 0.000 description 1
• CXJWLLXWCAVZNN-UHFFFAOYSA-N tert-butyl 2,3-dihydropyrrolo[2,3-c]pyridine-1-carboxylate Chemical compound C1=NC=C2N(C(=O)OC(C)(C)C)CCC2=C1 CXJWLLXWCAVZNN-UHFFFAOYSA-N 0.000 description 1
• HSXLTLXVJGPLHG-UHFFFAOYSA-N tert-butyl 2-hydroxy-2,3-dihydropyrrolo[2,3-c]pyridine-1-carboxylate Chemical compound C1=NC=C2N(C(=O)OC(C)(C)C)C(O)CC2=C1 HSXLTLXVJGPLHG-UHFFFAOYSA-N 0.000 description 1
• MUDQBZKZJHBWPG-UHFFFAOYSA-N tert-butyl 6-pyridin-3-yl-3,3a,4,5,7,7a-hexahydro-2h-pyrrolo[2,3-c]pyridine-1-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CCC2CCN1C1=CC=CN=C1 MUDQBZKZJHBWPG-UHFFFAOYSA-N 0.000 description 1
• ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
• VDJQDKIUIIFWJD-UHFFFAOYSA-N tert-butyl pyrrolo[2,3-c]pyridine-1-carboxylate Chemical compound C1=NC=C2N(C(=O)OC(C)(C)C)C=CC2=C1 VDJQDKIUIIFWJD-UHFFFAOYSA-N 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
• BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
• 125000002769 thiazolinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
• HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
• 239000004408 titanium dioxide Substances 0.000 description 1
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
• 235000015149 toffees Nutrition 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 229950004288 tosilate Drugs 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 229910052723 transition metal Inorganic materials 0.000 description 1
• 150000003624 transition metals Chemical class 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
• 229910052905 tridymite Inorganic materials 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
• 229940038773 trisodium citrate Drugs 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 231100000397 ulcer Toxicity 0.000 description 1
• 210000001215 vagina Anatomy 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 235000013311 vegetables Nutrition 0.000 description 1
• 239000010497 wheat germ oil Substances 0.000 description 1
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1