TW201020244A - New compounds - Google Patents

Info

Publication number

TW201020244A

TW201020244A TW098138485A TW98138485A TW201020244A TW 201020244 A TW201020244 A TW 201020244A TW 098138485 A TW098138485 A TW 098138485A TW 98138485 A TW98138485 A TW 98138485A TW 201020244 A TW201020244 A TW 201020244A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

phenyl

fluoro

pyridyl

Prior art date

2008-11-14

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 281
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 102
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 72
• 206010012289 Dementia Diseases 0.000 claims abstract description 67
• 201000010099 disease Diseases 0.000 claims abstract description 65
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 31
• 238000011282 treatment Methods 0.000 claims abstract description 29
• 208000024891 symptom Diseases 0.000 claims abstract description 20
• 230000003412 degenerative effect Effects 0.000 claims abstract description 19
• 230000001054 cortical effect Effects 0.000 claims abstract description 18
• 208000000044 Amnesia Diseases 0.000 claims abstract description 17
• 208000026139 Memory disease Diseases 0.000 claims abstract description 17
• 230000007850 degeneration Effects 0.000 claims abstract description 17
• 230000006984 memory degeneration Effects 0.000 claims abstract description 17
• 208000023060 memory loss Diseases 0.000 claims abstract description 17
• 206010008111 Cerebral haemorrhage Diseases 0.000 claims abstract description 16
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 15
• 206010059245 Angiopathy Diseases 0.000 claims abstract description 13
• 230000002265 prevention Effects 0.000 claims abstract description 13
• 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims abstract description 10
• 230000006735 deficit Effects 0.000 claims abstract description 10
• 201000010374 Down Syndrome Diseases 0.000 claims abstract description 9
• 206010044688 Trisomy 21 Diseases 0.000 claims abstract description 9
• 230000007170 pathology Effects 0.000 claims abstract description 8
• 208000035475 disorder Diseases 0.000 claims abstract description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• 230000002792 vascular Effects 0.000 claims abstract description 7
• -1 C2-6 Chemical group 0.000 claims description 294
• 125000000217 alkyl group Chemical group 0.000 claims description 289
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 125
• 125000001072 heteroaryl group Chemical group 0.000 claims description 97
• 125000003118 aryl group Chemical group 0.000 claims description 87
• 150000003839 salts Chemical class 0.000 claims description 69
• 239000002585 base Substances 0.000 claims description 66
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
• 125000000623 heterocyclic group Chemical group 0.000 claims description 57
• 229910052736 halogen Inorganic materials 0.000 claims description 54
• 125000004076 pyridyl group Chemical group 0.000 claims description 50
• 125000003545 alkoxy group Chemical group 0.000 claims description 46
• 150000001412 amines Chemical class 0.000 claims description 45
• 238000000034 method Methods 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 239000003814 drug Substances 0.000 claims description 36
• 239000007789 gas Substances 0.000 claims description 36
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 36
• 150000002431 hydrogen Chemical group 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 35
• 230000001575 pathological effect Effects 0.000 claims description 35
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 30
• 125000001188 haloalkyl group Chemical group 0.000 claims description 28
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 26
• 230000006999 cognitive decline Effects 0.000 claims description 24
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• 241000124008 Mammalia Species 0.000 claims description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
• 125000001153 fluoro group Chemical group F* 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• TXQAZWIBPGKHOX-UHFFFAOYSA-N Indole-3-amine Natural products C1=CC=C2C(N)=CNC2=C1 TXQAZWIBPGKHOX-UHFFFAOYSA-N 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
• 125000004429 atom Chemical group 0.000 claims description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 230000000750 progressive effect Effects 0.000 claims description 16
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000002837 carbocyclic group Chemical group 0.000 claims description 15
• 150000002825 nitriles Chemical class 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 230000032683 aging Effects 0.000 claims description 11
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 208000011580 syndromic disease Diseases 0.000 claims description 10
• 208000003251 Pruritus Diseases 0.000 claims description 9
• 210000004556 brain Anatomy 0.000 claims description 9
• 239000002475 cognitive enhancer Substances 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 9
• 239000003695 memory enhancer Substances 0.000 claims description 9
• 238000012360 testing method Methods 0.000 claims description 9
• 206010036790 Productive cough Diseases 0.000 claims description 8
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
• 210000003802 sputum Anatomy 0.000 claims description 8
• 208000024794 sputum Diseases 0.000 claims description 8
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 7
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 206010033799 Paralysis Diseases 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 150000002923 oximes Chemical class 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 239000012458 free base Substances 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 claims description 3
• SPSYMWKHDUJABD-UHFFFAOYSA-N 2h-isoindol-1-amine Chemical compound C1=CC=CC2=C(N)NC=C21 SPSYMWKHDUJABD-UHFFFAOYSA-N 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• 239000003513 alkali Substances 0.000 claims description 3
• 125000006612 decyloxy group Chemical group 0.000 claims description 3
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• PMCOWOCKUQWYRL-UHFFFAOYSA-N 2,4-dimethylpyrimidine Chemical compound CC1=CC=NC(C)=N1 PMCOWOCKUQWYRL-UHFFFAOYSA-N 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
• 101800001586 Ghrelin Proteins 0.000 claims description 2
• 102000012004 Ghrelin Human genes 0.000 claims description 2
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 2
• 229910052802 copper Inorganic materials 0.000 claims description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 210000004268 dentin Anatomy 0.000 claims description 2
• 239000002532 enzyme inhibitor Substances 0.000 claims description 2
• 229940125532 enzyme inhibitor Drugs 0.000 claims description 2
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
• GNKDKYIHGQKHHM-RJKLHVOGSA-N ghrelin Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)CN)COC(=O)CCCCCCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C1=CC=CC=C1 GNKDKYIHGQKHHM-RJKLHVOGSA-N 0.000 claims description 2
• 230000007803 itching Effects 0.000 claims description 2
• 239000001814 pectin Substances 0.000 claims description 2
• 235000010987 pectin Nutrition 0.000 claims description 2
• 229920001277 pectin Polymers 0.000 claims description 2
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 2
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 2
• 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• MHHCQOHRMSGYSG-UHFFFAOYSA-N 5-(1h-pyrrol-2-yl)pyrimidine Chemical compound C1=CNC(C=2C=NC=NC=2)=C1 MHHCQOHRMSGYSG-UHFFFAOYSA-N 0.000 claims 1
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
• 206010028980 Neoplasm Diseases 0.000 claims 1
• 241000253387 Rhodobiaceae Species 0.000 claims 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 201000011510 cancer Diseases 0.000 claims 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
• 125000002944 cyanoaryl group Chemical group 0.000 claims 1
• 150000001925 cycloalkenes Chemical class 0.000 claims 1
• 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 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• 239000012433 hydrogen halide Substances 0.000 claims 1
• 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
• 125000004043 oxo group Chemical group O=* 0.000 claims 1
• 150000003254 radicals Chemical class 0.000 claims 1
• 238000004513 sizing Methods 0.000 claims 1
• 239000002689 soil Substances 0.000 claims 1
• 208000018737 Parkinson disease Diseases 0.000 abstract description 13
• 208000028698 Cognitive impairment Diseases 0.000 abstract description 5
• 238000002560 therapeutic procedure Methods 0.000 abstract description 4
• 201000002212 progressive supranuclear palsy Diseases 0.000 abstract description 3
• 206010039966 Senile dementia Diseases 0.000 abstract description 2
• 208000027061 mild cognitive impairment Diseases 0.000 abstract description 2
• 102000013455 Amyloid beta-Peptides Human genes 0.000 abstract 1
• 108010090849 Amyloid beta-Peptides Proteins 0.000 abstract 1
• 206010036631 Presenile dementia Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 257
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 131
• 235000019439 ethyl acetate Nutrition 0.000 description 121
• 239000000203 mixture Substances 0.000 description 115
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 110
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 101
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 88
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
• 239000000243 solution Substances 0.000 description 55
• 238000005481 NMR spectroscopy Methods 0.000 description 52
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
• 238000005160 1H NMR spectroscopy Methods 0.000 description 43
• 101150041968 CDC13 gene Proteins 0.000 description 38
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
• 238000006243 chemical reaction Methods 0.000 description 34
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 32
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• 239000002207 metabolite Substances 0.000 description 23
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 22
• 238000004949 mass spectrometry Methods 0.000 description 22
• HZFPPBMKGYINDF-UHFFFAOYSA-N pyrimidin-5-ylboronic acid Chemical compound OB(O)C1=CN=CN=C1 HZFPPBMKGYINDF-UHFFFAOYSA-N 0.000 description 21
• 229920006395 saturated elastomer Polymers 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
• 102100021257 Beta-secretase 1 Human genes 0.000 description 18
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• 239000010949 copper Substances 0.000 description 18
• 230000002829 reductive effect Effects 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 108090000623 proteins and genes Proteins 0.000 description 16
• 239000012300 argon atmosphere Substances 0.000 description 15
• 125000004432 carbon atom Chemical group C* 0.000 description 15
• 239000003112 inhibitor Substances 0.000 description 15
• 239000012074 organic phase Substances 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 239000000460 chlorine Substances 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 238000002953 preparative HPLC Methods 0.000 description 14
• 235000018102 proteins Nutrition 0.000 description 14
• 102000004169 proteins and genes Human genes 0.000 description 14
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 13
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
• 239000007864 aqueous solution Substances 0.000 description 13
• 239000012267 brine Substances 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 13
• 239000003795 chemical substances by application Substances 0.000 description 13
• 238000003818 flash chromatography Methods 0.000 description 13
• 229910052763 palladium Inorganic materials 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
• 239000003643 water by type Substances 0.000 description 13
• IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 102000004190 Enzymes Human genes 0.000 description 12
• 108090000790 Enzymes Proteins 0.000 description 12
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 230000015572 biosynthetic process Effects 0.000 description 12
• 229940088598 enzyme Drugs 0.000 description 12
• 229910052742 iron Inorganic materials 0.000 description 12
• 238000004519 manufacturing process Methods 0.000 description 12
• 239000012071 phase Substances 0.000 description 12
• 239000000523 sample Substances 0.000 description 12
• 229910052938 sodium sulfate Inorganic materials 0.000 description 12
• 235000011152 sodium sulphate Nutrition 0.000 description 12
• 238000003786 synthesis reaction Methods 0.000 description 12
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
• 229910052796 boron Inorganic materials 0.000 description 11
• 238000001816 cooling Methods 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• 208000019553 vascular disease Diseases 0.000 description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 10
• KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 238000001514 detection method Methods 0.000 description 9
• 125000005842 heteroatom Chemical group 0.000 description 9
• 150000002500 ions Chemical class 0.000 description 9
• 239000011777 magnesium Substances 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 8
• 210000004204 blood vessel Anatomy 0.000 description 8
• ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 238000002309 gasification Methods 0.000 description 8
• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
• 229960005017 olanzapine Drugs 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• 239000007832 Na2SO4 Substances 0.000 description 7
• 239000003693 atypical antipsychotic agent Substances 0.000 description 7
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
• 239000000544 cholinesterase inhibitor Substances 0.000 description 7
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
• 239000002243 precursor Substances 0.000 description 7
• 238000006467 substitution reaction Methods 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 238000004458 analytical method Methods 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• 239000012634 fragment Substances 0.000 description 6
• 229960002870 gabapentin Drugs 0.000 description 6
• 238000004128 high performance liquid chromatography Methods 0.000 description 6
• 238000001727 in vivo Methods 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
• LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 6
• 239000011368 organic material Substances 0.000 description 6
• 229960004431 quetiapine Drugs 0.000 description 6
• URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 6
• RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 6
• UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229940124597 therapeutic agent Drugs 0.000 description 6
• MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 6
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 5
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 5
• HJCMDXDYPOUFDY-WHFBIAKZSA-N Ala-Gln Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CCC(N)=O HJCMDXDYPOUFDY-WHFBIAKZSA-N 0.000 description 5
• 239000005695 Ammonium acetate Substances 0.000 description 5
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 5
• 239000007983 Tris buffer Substances 0.000 description 5
• 150000001336 alkenes Chemical class 0.000 description 5
• 235000019257 ammonium acetate Nutrition 0.000 description 5
• 229940043376 ammonium acetate Drugs 0.000 description 5
• 238000003556 assay Methods 0.000 description 5
• 229940127236 atypical antipsychotics Drugs 0.000 description 5
• 238000000451 chemical ionisation Methods 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• XFVGXQSSXWIWIO-UHFFFAOYSA-N chloro hypochlorite;titanium Chemical compound [Ti].ClOCl XFVGXQSSXWIWIO-UHFFFAOYSA-N 0.000 description 5
• QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 5
• 230000001149 cognitive effect Effects 0.000 description 5
• 230000008021 deposition Effects 0.000 description 5
• 125000003963 dichloro group Chemical group Cl* 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 239000003797 essential amino acid Substances 0.000 description 5
• 235000020776 essential amino acid Nutrition 0.000 description 5
• 239000000284 extract Substances 0.000 description 5
• 125000001207 fluorophenyl group Chemical group 0.000 description 5
• ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 5
• 150000002576 ketones Chemical class 0.000 description 5
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 5
• 238000000926 separation method Methods 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• 238000004704 ultra performance liquid chromatography Methods 0.000 description 5
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 4
• ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 4
• 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 4
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• 238000004293 19F NMR spectroscopy Methods 0.000 description 4
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 4
• QHLLEZOPZRBCOY-UHFFFAOYSA-N 4-bromo-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(Br)=CC=N1 QHLLEZOPZRBCOY-UHFFFAOYSA-N 0.000 description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• 229940122041 Cholinesterase inhibitor Drugs 0.000 description 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• YLXDSYKOBKBWJQ-LBPRGKRZSA-N N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e]benzofuran-8-yl]ethyl]propanamide Chemical compound C1=C2OCCC2=C2[C@H](CCNC(=O)CC)CCC2=C1 YLXDSYKOBKBWJQ-LBPRGKRZSA-N 0.000 description 4
• 150000001204 N-oxides Chemical class 0.000 description 4
• 208000002193 Pain Diseases 0.000 description 4
• 229910002666 PdCl2 Inorganic materials 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
• 229960002629 agomelatine Drugs 0.000 description 4
• YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 description 4
• 125000001931 aliphatic group Chemical group 0.000 description 4
• 125000003277 amino group Chemical group 0.000 description 4
• VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical compound CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 description 4
• 229960004372 aripiprazole Drugs 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical group OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 4
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
• 238000011161 development Methods 0.000 description 4
• 230000018109 developmental process Effects 0.000 description 4
• 229960002866 duloxetine Drugs 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 229960002464 fluoxetine Drugs 0.000 description 4
• ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
• 229910052740 iodine Inorganic materials 0.000 description 4
• 229960001848 lamotrigine Drugs 0.000 description 4
• PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
• 229960004640 memantine Drugs 0.000 description 4
• 230000002503 metabolic effect Effects 0.000 description 4
• 229960002715 nicotine Drugs 0.000 description 4
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 4
• 239000012299 nitrogen atmosphere Substances 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• 229910052760 oxygen Inorganic materials 0.000 description 4
• 239000001301 oxygen Substances 0.000 description 4
• WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
• FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 229960001150 ramelteon Drugs 0.000 description 4
• 229960001534 risperidone Drugs 0.000 description 4
• MQTUXRKNJYPMCG-CYBMUJFWSA-N robalzotan Chemical compound C1CCC1N([C@H]1COC=2C(F)=CC=C(C=2C1)C(=O)N)C1CCC1 MQTUXRKNJYPMCG-CYBMUJFWSA-N 0.000 description 4
• 229950003023 robalzotan Drugs 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• 238000001228 spectrum Methods 0.000 description 4
• 229910052717 sulfur Inorganic materials 0.000 description 4
• 229960001685 tacrine Drugs 0.000 description 4
• YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 4
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
• 229910052725 zinc Inorganic materials 0.000 description 4
• 239000011701 zinc Substances 0.000 description 4
• 229960000607 ziprasidone Drugs 0.000 description 4
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 3
• 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 229960002319 barbital Drugs 0.000 description 3
• FTOAOBMCPZCFFF-UHFFFAOYSA-N barbitone sodium Natural products CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 3
• 229940049706 benzodiazepine Drugs 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
• 229910000024 caesium carbonate Inorganic materials 0.000 description 3
• 206010008129 cerebral palsy Diseases 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
• 238000003776 cleavage reaction Methods 0.000 description 3
• 229960004170 clozapine Drugs 0.000 description 3
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
• 238000004807 desolvation Methods 0.000 description 3
• 229960003530 donepezil Drugs 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
• 230000002401 inhibitory effect Effects 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 239000011630 iodine Substances 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• 229910052749 magnesium Inorganic materials 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 description 3
• MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
• 229960005489 paracetamol Drugs 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 238000002360 preparation method Methods 0.000 description 3
• 108090000765 processed proteins & peptides Proteins 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 230000007017 scission Effects 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• 238000010257 thawing Methods 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• 238000012546 transfer Methods 0.000 description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
• MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 3
• 229960000604 valproic acid Drugs 0.000 description 3
• AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 2
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
• JCKZNMSBFBPDPM-UHFFFAOYSA-N (2-fluoro-3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1F JCKZNMSBFBPDPM-UHFFFAOYSA-N 0.000 description 2
• LHYMPSWMHXUWSK-STZFKDTASA-N (2z)-4-(3,4-dichlorophenyl)-2-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]thiomorpholin-3-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1\C=C/1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)CCS\1 LHYMPSWMHXUWSK-STZFKDTASA-N 0.000 description 2
• DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 2
• CYEXXDYQJPRMIQ-UHFFFAOYSA-N (5-cyanopyridin-3-yl)boronic acid Chemical compound OB(O)C1=CN=CC(C#N)=C1 CYEXXDYQJPRMIQ-UHFFFAOYSA-N 0.000 description 2
• GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 description 2
• ICPHJSKVAZMKIV-QGZVFWFLSA-N (5r)-7,8-dimethoxy-3-methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1([C@H]2CN(C)CCC=3C=C(C(=CC=32)OC)OC)=CC=CC=C1 ICPHJSKVAZMKIV-QGZVFWFLSA-N 0.000 description 2
• WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 2
• VSWBSWWIRNCQIJ-GJZGRUSLSA-N (R,R)-asenapine Chemical compound O1C2=CC=CC=C2[C@@H]2CN(C)C[C@H]2C2=CC(Cl)=CC=C21 VSWBSWWIRNCQIJ-GJZGRUSLSA-N 0.000 description 2
• BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 2
• ZEHYJZXQEQOSON-AATRIKPKSA-N (e)-1-chloro-3-ethylpent-1-en-4-yn-3-ol Chemical compound CCC(O)(C#C)\C=C\Cl ZEHYJZXQEQOSON-AATRIKPKSA-N 0.000 description 2
• QECAKYKTTYQVKX-RMKNXTFCSA-N (e)-3-(2,5-dihydropyrrol-1-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)\C=C\N2CC=CC2)=C1 QECAKYKTTYQVKX-RMKNXTFCSA-N 0.000 description 2
• TZJUVVIWVWFLCD-UHFFFAOYSA-N 1,1-dioxo-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-1,2-benzothiazol-3-one Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 TZJUVVIWVWFLCD-UHFFFAOYSA-N 0.000 description 2
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
• OEAJNZQFAHZXAB-UHFFFAOYSA-N 1,4-dioxane;methane Chemical compound C.C1COCCO1 OEAJNZQFAHZXAB-UHFFFAOYSA-N 0.000 description 2
• UNFQKKSADLVQJE-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea;hydrate Chemical compound O.CN1CC(=O)N=C1NC(=O)NC1=CC=CC(Cl)=C1 UNFQKKSADLVQJE-UHFFFAOYSA-N 0.000 description 2
• GELASUFEZONUHG-UHFFFAOYSA-N 1-(sulfinylamino)decane Chemical compound CCCCCCCCCCN=S=O GELASUFEZONUHG-UHFFFAOYSA-N 0.000 description 2
• QEMSVZNTSXPFJA-HNAYVOBHSA-N 1-[(1s,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]-4-phenylpiperidin-4-ol Chemical compound C1([C@H](O)[C@H](C)N2CCC(O)(CC2)C=2C=CC=CC=2)=CC=C(O)C=C1 QEMSVZNTSXPFJA-HNAYVOBHSA-N 0.000 description 2
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
• KYWMWUUMCDZISK-UHFFFAOYSA-N 2,2,5,5-tetrakis(trifluoromethyl)-1h-imidazol-4-amine Chemical compound NC1=NC(C(F)(F)F)(C(F)(F)F)NC1(C(F)(F)F)C(F)(F)F KYWMWUUMCDZISK-UHFFFAOYSA-N 0.000 description 2
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
• SPCKHVPPRJWQRZ-UHFFFAOYSA-N 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 SPCKHVPPRJWQRZ-UHFFFAOYSA-N 0.000 description 2
• PYEQXZOIQJWYAH-UHFFFAOYSA-N 2-bromocyclohexa-2,5-diene-1,4-dione Chemical compound BrC1=CC(=O)C=CC1=O PYEQXZOIQJWYAH-UHFFFAOYSA-N 0.000 description 2
• GTFCXOTXJVOQOJ-UHFFFAOYSA-N 2-trimethylstannylpyridine-4-carbonitrile Chemical compound C[Sn](C)(C)C1=CC(C#N)=CC=N1 GTFCXOTXJVOQOJ-UHFFFAOYSA-N 0.000 description 2
• FXZJKVODWNYPKK-UHFFFAOYSA-N 3-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-1h-quinazoline-2,4-dione Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(C4=CC=CC=C4NC3=O)=O)CC2)=C1 FXZJKVODWNYPKK-UHFFFAOYSA-N 0.000 description 2
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
• PMXMIIMHBWHSKN-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCC(O)C4=NC=3C)=NOC2=C1 PMXMIIMHBWHSKN-UHFFFAOYSA-N 0.000 description 2
• PCTRYMLLRKWXGF-UHFFFAOYSA-N 4-(butylamino)-1-ethyl-6-methyl-5-pyrazolo[3,4-b]pyridinecarboxylic acid ethyl ester Chemical compound CCCCNC1=C(C(=O)OCC)C(C)=NC2=C1C=NN2CC PCTRYMLLRKWXGF-UHFFFAOYSA-N 0.000 description 2
• QYFHCFNBYQZGKW-BDQAORGHSA-N 8-[4-[[(3s)-5-methoxy-3,4-dihydro-2h-chromen-3-yl]-propylamino]butyl]-8-azaspiro[4.5]decane-7,9-dione;hydrochloride Chemical compound Cl.CCCN([C@H]1CC2=C(OC)C=CC=C2OC1)CCCCN(C(C1)=O)C(=O)CC21CCCC2 QYFHCFNBYQZGKW-BDQAORGHSA-N 0.000 description 2
• WKEMJKQOLOHJLZ-UHFFFAOYSA-N Almogran Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CS(=O)(=O)N1CCCC1 WKEMJKQOLOHJLZ-UHFFFAOYSA-N 0.000 description 2
• 102100028116 Amine oxidase [flavin-containing] B Human genes 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 208000037259 Amyloid Plaque Diseases 0.000 description 2
• 102000009091 Amyloidogenic Proteins Human genes 0.000 description 2
• 108010048112 Amyloidogenic Proteins Proteins 0.000 description 2
• 241000683250 Argentinidae Species 0.000 description 2
• 101710150192 Beta-secretase 1 Proteins 0.000 description 2
• CYGODHVAJQTCBG-UHFFFAOYSA-N Bifeprunox Chemical compound C=12OC(=O)NC2=CC=CC=1N(CC1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 CYGODHVAJQTCBG-UHFFFAOYSA-N 0.000 description 2
• KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
• GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 2
• HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 2
• 108010057987 Desmodus rotundus salivary plasminogen activator alpha 1 Proteins 0.000 description 2
• XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 2
• NCSLXGIFBLJQFW-UHFFFAOYSA-N FC1=CC=CC([Zn])=C1C#N Chemical compound FC1=CC=CC([Zn])=C1C#N NCSLXGIFBLJQFW-UHFFFAOYSA-N 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• 101000768078 Homo sapiens Amine oxidase [flavin-containing] B Proteins 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
• WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
• NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
• 102000003960 Ligases Human genes 0.000 description 2
• 108090000364 Ligases Proteins 0.000 description 2
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
• YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 2
• JEYCTXHKTXCGPB-UHFFFAOYSA-N Methaqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C JEYCTXHKTXCGPB-UHFFFAOYSA-N 0.000 description 2
• 208000019695 Migraine disease Diseases 0.000 description 2
• HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
• RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 description 2
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
• CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
• 208000001294 Nociceptive Pain Diseases 0.000 description 2
• PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 2
• 235000021314 Palmitic acid Nutrition 0.000 description 2
• AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 2
• 108090000284 Pepsin A Proteins 0.000 description 2
• 102000057297 Pepsin A Human genes 0.000 description 2
• PWRPUAKXMQAFCJ-UHFFFAOYSA-N Perlapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2CC2=CC=CC=C12 PWRPUAKXMQAFCJ-UHFFFAOYSA-N 0.000 description 2
• RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 2
• MWQCHHACWWAQLJ-UHFFFAOYSA-N Prazepam Chemical compound O=C1CN=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CC1 MWQCHHACWWAQLJ-UHFFFAOYSA-N 0.000 description 2
• QPCVHQBVMYCJOM-UHFFFAOYSA-N Propiverine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(=O)OC1CCN(C)CC1 QPCVHQBVMYCJOM-UHFFFAOYSA-N 0.000 description 2
• IKMPWMZBZSAONZ-UHFFFAOYSA-N Quazepam Chemical compound FC1=CC=CC=C1C1=NCC(=S)N(CC(F)(F)F)C2=CC=C(Cl)C=C12 IKMPWMZBZSAONZ-UHFFFAOYSA-N 0.000 description 2
• LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
• BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 description 2
• XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 2
• PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 2
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 2
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
• SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 2
• 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 2
• 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 2
• 206010046543 Urinary incontinence Diseases 0.000 description 2
• 241000607479 Yersinia pestis Species 0.000 description 2
• GDSCFOSHSOWNDL-UHFFFAOYSA-N Zolasepam Chemical compound N=1CC(=O)N(C)C(N(N=C2C)C)=C2C=1C1=CC=CC=C1F GDSCFOSHSOWNDL-UHFFFAOYSA-N 0.000 description 2
• 229960000446 abciximab Drugs 0.000 description 2
• 229940056213 abilify Drugs 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 229940099983 activase Drugs 0.000 description 2
• GJSLOMWRLALDCT-UHFFFAOYSA-N adinazolam Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 GJSLOMWRLALDCT-UHFFFAOYSA-N 0.000 description 2
• 229960003148 adinazolam Drugs 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 229960002133 almotriptan Drugs 0.000 description 2
• 229950000420 alnespirone Drugs 0.000 description 2
• 229960003805 amantadine Drugs 0.000 description 2
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 2
• 229960003036 amisulpride Drugs 0.000 description 2
• NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 description 2
• KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
• 229960000836 amitriptyline Drugs 0.000 description 2
• 229960001301 amobarbital Drugs 0.000 description 2
• QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 description 2
• 229960002519 amoxapine Drugs 0.000 description 2
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
• 239000005557 antagonist Substances 0.000 description 2
• 229940121363 anti-inflammatory agent Drugs 0.000 description 2
• 239000002260 anti-inflammatory agent Substances 0.000 description 2
• 229940125681 anticonvulsant agent Drugs 0.000 description 2
• 239000001961 anticonvulsive agent Substances 0.000 description 2
• 239000000164 antipsychotic agent Substances 0.000 description 2
• 229940005529 antipsychotics Drugs 0.000 description 2
• 239000002249 anxiolytic agent Substances 0.000 description 2
• 229910052786 argon Inorganic materials 0.000 description 2
• 229960005245 asenapine Drugs 0.000 description 2
• 229940125717 barbiturate Drugs 0.000 description 2
• AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
• AIZFEOPQVZBNGH-UHFFFAOYSA-N bentazepam Chemical compound C1=2C=3CCCCC=3SC=2NC(=O)CN=C1C1=CC=CC=C1 AIZFEOPQVZBNGH-UHFFFAOYSA-N 0.000 description 2
• 229950001957 bentazepam Drugs 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• 125000005605 benzo group Chemical group 0.000 description 2
• GNRXCIONJWKSEA-UHFFFAOYSA-N benzoctamine Chemical compound C12=CC=CC=C2C2(CNC)C3=CC=CC=C3C1CC2 GNRXCIONJWKSEA-UHFFFAOYSA-N 0.000 description 2
• 229960001303 benzoctamine Drugs 0.000 description 2
• 150000001557 benzodiazepines Chemical class 0.000 description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
• 229950009087 bifeprunox Drugs 0.000 description 2
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
• 230000000903 blocking effect Effects 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
• QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 2
• 229960002495 buspirone Drugs 0.000 description 2
• 229960004596 cabergoline Drugs 0.000 description 2
• HLSLSXBFTXUKCY-UHFFFAOYSA-N capuride Chemical compound CCC(C)C(CC)C(=O)NC(N)=O HLSLSXBFTXUKCY-UHFFFAOYSA-N 0.000 description 2
• 229950003152 capuride Drugs 0.000 description 2
• 235000011089 carbon dioxide Nutrition 0.000 description 2
• 229910002091 carbon monoxide Inorganic materials 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 229960000590 celecoxib Drugs 0.000 description 2
• RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 2
• 239000006143 cell culture medium Substances 0.000 description 2
• 210000000170 cell membrane Anatomy 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 210000000349 chromosome Anatomy 0.000 description 2
• 229960001653 citalopram Drugs 0.000 description 2
• 229960004606 clomipramine Drugs 0.000 description 2
• DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 2
• 229960003120 clonazepam Drugs 0.000 description 2
• 229950000551 cloperidone Drugs 0.000 description 2
• 229960004362 clorazepate Drugs 0.000 description 2
• XDDJGVMJFWAHJX-UHFFFAOYSA-N clorazepic acid Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(C(=O)O)N=C1C1=CC=CC=C1 XDDJGVMJFWAHJX-UHFFFAOYSA-N 0.000 description 2
• 239000013066 combination product Substances 0.000 description 2
• 229940127555 combination product Drugs 0.000 description 2
• 239000002299 complementary DNA Substances 0.000 description 2
• 238000011254 conventional chemotherapy Methods 0.000 description 2
• QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
• 238000011262 co‐therapy Methods 0.000 description 2
• 239000013058 crude material Substances 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• 230000001086 cytosolic effect Effects 0.000 description 2
• 231100000135 cytotoxicity Toxicity 0.000 description 2
• 230000003013 cytotoxicity Effects 0.000 description 2
• 229960003914 desipramine Drugs 0.000 description 2
• 229950001282 desmoteplase Drugs 0.000 description 2
• UPMOVJBGNREKJV-CQOQZXRMSA-N dexclamol Chemical compound C12=CC=CC=C2CCC2=CC=CC3=C2[C@@H]1CN1CC[C@@](C(C)C)(O)C[C@@H]13 UPMOVJBGNREKJV-CQOQZXRMSA-N 0.000 description 2
• 229950005215 dexclamol Drugs 0.000 description 2
• ATKXDQOHNICLQW-UHFFFAOYSA-N dichloralphenazone Chemical compound OC(O)C(Cl)(Cl)Cl.OC(O)C(Cl)(Cl)Cl.CN1C(C)=CC(=O)N1C1=CC=CC=C1 ATKXDQOHNICLQW-UHFFFAOYSA-N 0.000 description 2
• 229960005422 dichloralphenazone Drugs 0.000 description 2
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 2
• 229960001259 diclofenac Drugs 0.000 description 2
• QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
• RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
• MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
• 229960000520 diphenhydramine Drugs 0.000 description 2
• XLZOVRYBVCMCGL-BPNVQINPSA-L disodium;4-[(z)-[tert-butyl(oxido)azaniumylidene]methyl]benzene-1,3-disulfonate Chemical compound [Na+].[Na+].CC(C)(C)[N+](\[O-])=C\C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O XLZOVRYBVCMCGL-BPNVQINPSA-L 0.000 description 2
• 150000004141 diterpene derivatives Chemical class 0.000 description 2
• 229940052760 dopamine agonists Drugs 0.000 description 2
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
• 239000000221 dopamine uptake inhibitor Substances 0.000 description 2
• 229960005426 doxepin Drugs 0.000 description 2
• ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 2
• 229960002472 eletriptan Drugs 0.000 description 2
• PWVXXGRKLHYWKM-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 PWVXXGRKLHYWKM-LJQANCHMSA-N 0.000 description 2
• 229950007566 elzasonan Drugs 0.000 description 2
• WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 description 2
• 229960004341 escitalopram Drugs 0.000 description 2
• CDCHDCWJMGXXRH-UHFFFAOYSA-N estazolam Chemical compound C=1C(Cl)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=C1 CDCHDCWJMGXXRH-UHFFFAOYSA-N 0.000 description 2
• 229960002336 estazolam Drugs 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• GBBSUAFBMRNDJC-INIZCTEOSA-N eszopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-INIZCTEOSA-N 0.000 description 2
• 229960001578 eszopiclone Drugs 0.000 description 2
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
• 229960004447 ethchlorvynol Drugs 0.000 description 2
• MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 2
• 229960004945 etoricoxib Drugs 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 229950002489 fenobam Drugs 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 229960002200 flunitrazepam Drugs 0.000 description 2
• 229960003528 flurazepam Drugs 0.000 description 2
• SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 description 2
• 230000002431 foraging effect Effects 0.000 description 2
• 229960002284 frovatriptan Drugs 0.000 description 2
• SIBNYOSJIXCDRI-SECBINFHSA-N frovatriptan Chemical compound C1=C(C(N)=O)[CH]C2=C(C[C@H](NC)CC3)C3=NC2=C1 SIBNYOSJIXCDRI-SECBINFHSA-N 0.000 description 2
• 229940003380 geodon Drugs 0.000 description 2
• QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 description 2
• 229960000647 gepirone Drugs 0.000 description 2
• 239000011521 glass Substances 0.000 description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
• ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 description 2
• 229960000930 hydroxyzine Drugs 0.000 description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 description 2
• 206010022437 insomnia Diseases 0.000 description 2
• 238000007914 intraventricular administration Methods 0.000 description 2
• 229950003599 ipsapirone Drugs 0.000 description 2
• 235000013847 iso-butane Nutrition 0.000 description 2
• NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 229940060977 lidoderm Drugs 0.000 description 2
• 229960003587 lisuride Drugs 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 229960004391 lorazepam Drugs 0.000 description 2
• 229960000423 loxapine Drugs 0.000 description 2
• YQZBAXDVDZTKEQ-UHFFFAOYSA-N loxapine succinate Chemical compound [H+].[H+].[O-]C(=O)CCC([O-])=O.C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 YQZBAXDVDZTKEQ-UHFFFAOYSA-N 0.000 description 2
• 229960002373 loxoprofen Drugs 0.000 description 2
• BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 2
• 229960000994 lumiracoxib Drugs 0.000 description 2
• KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 description 2
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
• 229960004090 maprotiline Drugs 0.000 description 2
• QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 229960003987 melatonin Drugs 0.000 description 2
• DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 2
• ALARQZQTBTVLJV-UHFFFAOYSA-N mephobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)N(C)C1=O ALARQZQTBTVLJV-UHFFFAOYSA-N 0.000 description 2
• SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 description 2
• 229960000300 mesoridazine Drugs 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 229960002803 methaqualone Drugs 0.000 description 2
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 2
• 229960001703 methylphenobarbital Drugs 0.000 description 2
• 229950010642 midaflur Drugs 0.000 description 2
• DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 description 2
• 229960003793 midazolam Drugs 0.000 description 2
• 206010027599 migraine Diseases 0.000 description 2
• 235000010755 mineral Nutrition 0.000 description 2
• 239000011707 mineral Substances 0.000 description 2
• 229940101972 mirapex Drugs 0.000 description 2
• 239000004050 mood stabilizer Substances 0.000 description 2
• 229940127237 mood stabilizer Drugs 0.000 description 2
• 230000004899 motility Effects 0.000 description 2
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
• NDVZIUGCCMZHLG-UHFFFAOYSA-N n-methyl-3-(2-methylsulfanylphenoxy)-3-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1SC NDVZIUGCCMZHLG-UHFFFAOYSA-N 0.000 description 2
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
• 229960002009 naproxen Drugs 0.000 description 2
• 229960005254 naratriptan Drugs 0.000 description 2
• AMKVXSZCKVJAGH-UHFFFAOYSA-N naratriptan Chemical compound C12=CC(CCS(=O)(=O)NC)=CC=C2NC=C1C1CCN(C)CC1 AMKVXSZCKVJAGH-UHFFFAOYSA-N 0.000 description 2
• 229960001800 nefazodone Drugs 0.000 description 2
• VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 description 2
• 230000001537 neural effect Effects 0.000 description 2
• CBDPCXYQNVDTMW-UHFFFAOYSA-N nisobamate Chemical compound NC(=O)OCC(C)(C(C)CC)COC(=O)NC(C)C CBDPCXYQNVDTMW-UHFFFAOYSA-N 0.000 description 2
• 229950008643 nisobamate Drugs 0.000 description 2
• 229960001454 nitrazepam Drugs 0.000 description 2
• KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 2
• 229960001158 nortriptyline Drugs 0.000 description 2
• 210000004940 nucleus Anatomy 0.000 description 2
• 125000002524 organometallic group Chemical group 0.000 description 2
• 229960004535 oxazepam Drugs 0.000 description 2
• ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 2
• 229960005434 oxybutynin Drugs 0.000 description 2
• 229960001057 paliperidone Drugs 0.000 description 2
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
• 229960002296 paroxetine Drugs 0.000 description 2
• 230000037361 pathway Effects 0.000 description 2
• 229960001412 pentobarbital Drugs 0.000 description 2
• 229960004851 pergolide Drugs 0.000 description 2
• YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 2
• 229950009253 perlapine Drugs 0.000 description 2
• 229960000762 perphenazine Drugs 0.000 description 2
• DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
• 229960002695 phenobarbital Drugs 0.000 description 2
• KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
• YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 description 2
• 229960003634 pimozide Drugs 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 229960003089 pramipexole Drugs 0.000 description 2
• 229960004856 prazepam Drugs 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
• 238000004237 preparative chromatography Methods 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 2
• 229960003111 prochlorperazine Drugs 0.000 description 2
• KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
• 229960003510 propiverine Drugs 0.000 description 2
• OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 2
• 229960002601 protriptyline Drugs 0.000 description 2
• BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
• 229960001964 quazepam Drugs 0.000 description 2
• ZTHJULTYCAQOIJ-WXXKFALUSA-N quetiapine fumarate Chemical compound [H+].[H+].[O-]C(=O)\C=C\C([O-])=O.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 ZTHJULTYCAQOIJ-WXXKFALUSA-N 0.000 description 2
• 238000009790 rate-determining step (RDS) Methods 0.000 description 2
• 239000011535 reaction buffer Substances 0.000 description 2
• 229960003770 reboxetine Drugs 0.000 description 2
• CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 description 2
• YGYBFMRFXNDIPO-QGZVFWFLSA-N repinotan Chemical compound O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCNC[C@@H]1OC2=CC=CC=C2CC1 YGYBFMRFXNDIPO-QGZVFWFLSA-N 0.000 description 2
• 229950009693 repinotan Drugs 0.000 description 2
• 229940113775 requip Drugs 0.000 description 2
• 229940106887 risperdal Drugs 0.000 description 2
• 229960000425 rizatriptan Drugs 0.000 description 2
• TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 description 2
• 229960000371 rofecoxib Drugs 0.000 description 2
• RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 2
• 229950004692 roletamide Drugs 0.000 description 2
• 229960001879 ropinirole Drugs 0.000 description 2
• IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
• KQPKPCNLIDLUMF-UHFFFAOYSA-N secobarbital Chemical compound CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O KQPKPCNLIDLUMF-UHFFFAOYSA-N 0.000 description 2
• 229960002060 secobarbital Drugs 0.000 description 2
• 230000003248 secreting effect Effects 0.000 description 2
• MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 2
• 229940035004 seroquel Drugs 0.000 description 2
• GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 2
• 229960000652 sertindole Drugs 0.000 description 2
• 229960002073 sertraline Drugs 0.000 description 2
• VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 2
• 229960004425 sibutramine Drugs 0.000 description 2
• UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 2
• 238000010898 silica gel chromatography Methods 0.000 description 2
• 239000000779 smoke Substances 0.000 description 2
• APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
• FBOUYBDGKBSUES-VXKWHMMOSA-N solifenacin Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-VXKWHMMOSA-N 0.000 description 2
• 229960003855 solifenacin Drugs 0.000 description 2
• 239000002594 sorbent Substances 0.000 description 2
• 230000006641 stabilisation Effects 0.000 description 2
• 238000011105 stabilization Methods 0.000 description 2
• 238000010561 standard procedure Methods 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
• 235000021286 stilbenes Nutrition 0.000 description 2
• 239000011550 stock solution Substances 0.000 description 2
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
• 229960004940 sulpiride Drugs 0.000 description 2
• 229960003708 sumatriptan Drugs 0.000 description 2
• KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 2
• IBAUKGNDWVSETP-UHFFFAOYSA-N suproclone Chemical compound C1CN(C(=O)CC)CCN1C(=O)OC1C(SCCS2)=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 IBAUKGNDWVSETP-UHFFFAOYSA-N 0.000 description 2
• 229950003877 suproclone Drugs 0.000 description 2
• 229940034173 symbyax Drugs 0.000 description 2
• 230000002194 synthesizing effect Effects 0.000 description 2
• 229940000238 tasmar Drugs 0.000 description 2
• 229960003188 temazepam Drugs 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• 238000003971 tillage Methods 0.000 description 2
• OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
• MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 2
• OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 2
• 229960004045 tolterodine Drugs 0.000 description 2
• 229950002859 tracazolate Drugs 0.000 description 2
• 229910052723 transition metal Inorganic materials 0.000 description 2
• 150000003624 transition metals Chemical class 0.000 description 2
• 229950005135 traxoprodil Drugs 0.000 description 2
• 229960003991 trazodone Drugs 0.000 description 2
• PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 2
• 229950002464 trepipam Drugs 0.000 description 2
• QGAMJEFMDAVSKL-UHFFFAOYSA-N tributyl-(4-methoxypyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC(OC)=CC=N1 QGAMJEFMDAVSKL-UHFFFAOYSA-N 0.000 description 2
• ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 2
• 229960002324 trifluoperazine Drugs 0.000 description 2
• DTMPGSXFUXZBDK-UHFFFAOYSA-N uldazepam Chemical compound C12=CC(Cl)=CC=C2N=C(NOCC=C)CN=C1C1=CC=CC=C1Cl DTMPGSXFUXZBDK-UHFFFAOYSA-N 0.000 description 2
• 229950004526 uldazepam Drugs 0.000 description 2
• LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 2
• 229960002004 valdecoxib Drugs 0.000 description 2
• BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 2
• 229960004688 venlafaxine Drugs 0.000 description 2
• PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 2
• 229960001722 verapamil Drugs 0.000 description 2
• 239000011534 wash buffer Substances 0.000 description 2
• 210000002268 wool Anatomy 0.000 description 2
• 229960004010 zaleplon Drugs 0.000 description 2
• HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 2
• 229960001366 zolazepam Drugs 0.000 description 2
• 229960001360 zolmitriptan Drugs 0.000 description 2
• ULSDMUVEXKOYBU-ZDUSSCGKSA-N zolmitriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C[C@H]1COC(=O)N1 ULSDMUVEXKOYBU-ZDUSSCGKSA-N 0.000 description 2
• 229960001475 zolpidem Drugs 0.000 description 2
• ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 2
• 229960000820 zopiclone Drugs 0.000 description 2
• HDOZVRUNCMBHFH-UHFFFAOYSA-N zotepine Chemical compound CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12 HDOZVRUNCMBHFH-UHFFFAOYSA-N 0.000 description 2
• 229960004496 zotepine Drugs 0.000 description 2
• 229940039925 zyprexa Drugs 0.000 description 2
• XLDINQIAJJIHLB-UHFFFAOYSA-N (2-bromophenyl) formate Chemical compound BrC1=CC=CC=C1OC=O XLDINQIAJJIHLB-UHFFFAOYSA-N 0.000 description 1
• MWDNZMWVENFVHT-UHFFFAOYSA-L (2-decoxy-2-oxoethyl)-[2-[2-[(2-decoxy-2-oxoethyl)-dimethylazaniumyl]ethylsulfanyl]ethyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCOC(=O)C[N+](C)(C)CCSCC[N+](C)(C)CC(=O)OCCCCCCCCCC MWDNZMWVENFVHT-UHFFFAOYSA-L 0.000 description 1
• GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
• FJIKWRGCXUCUIG-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound O=C([C@H](O)N=1)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl FJIKWRGCXUCUIG-HNNXBMFYSA-N 0.000 description 1
• FVEDGBRHTGXPOK-UHFFFAOYSA-N (5-fluoropyridin-3-yl)boronic acid Chemical compound OB(O)C1=CN=CC(F)=C1 FVEDGBRHTGXPOK-UHFFFAOYSA-N 0.000 description 1
• PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
• UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
• ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
• OTBHDFWQZHPNPU-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CCCC2 OTBHDFWQZHPNPU-UHFFFAOYSA-N 0.000 description 1
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
• WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
• VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
• 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
• QVZXBANNBNDOFW-UHFFFAOYSA-N 1-(4-phenylbutyl)piperidine Chemical compound C1CCCCN1CCCCC1=CC=CC=C1 QVZXBANNBNDOFW-UHFFFAOYSA-N 0.000 description 1
• 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
• HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
• LFHLEABTNIQIQO-UHFFFAOYSA-N 1H-isoindole Chemical compound C1=CC=C2CN=CC2=C1 LFHLEABTNIQIQO-UHFFFAOYSA-N 0.000 description 1
• SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
• OAIYSDSCHLMYFF-UHFFFAOYSA-N 2,2,3,3-tetramethyldodecane Chemical compound CCCCCCCCCC(C)(C)C(C)(C)C OAIYSDSCHLMYFF-UHFFFAOYSA-N 0.000 description 1
• JOWBFITYYIZBFK-UHFFFAOYSA-N 2,2-bis(sulfanyl)acetamide Chemical compound NC(=O)C(S)S JOWBFITYYIZBFK-UHFFFAOYSA-N 0.000 description 1
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
• PCMMSLVJMKQWMQ-UHFFFAOYSA-N 2,4-dibromopyridine Chemical compound BrC1=CC=NC(Br)=C1 PCMMSLVJMKQWMQ-UHFFFAOYSA-N 0.000 description 1
• YOLWXYGTOQALFW-UHFFFAOYSA-N 2,4-dimethylpyridin-3-ol Chemical compound CC1=CC=NC(C)=C1O YOLWXYGTOQALFW-UHFFFAOYSA-N 0.000 description 1
• SGXOSZYAPUYDCF-UHFFFAOYSA-N 2-(2-bromopyridine-4-carbonyl)-6-fluorobenzonitrile Chemical compound FC1=CC=CC(C(=O)C=2C=C(Br)N=CC=2)=C1C#N SGXOSZYAPUYDCF-UHFFFAOYSA-N 0.000 description 1
• LZESGXVBLUWGEF-UHFFFAOYSA-N 2-bromo-5-fluorocyclohexa-2,5-diene-1,4-dione Chemical compound BrC=1C(C=C(C(C=1)=O)F)=O LZESGXVBLUWGEF-UHFFFAOYSA-N 0.000 description 1
• SUHYUUVUQGJUJC-UHFFFAOYSA-N 2-cyclopropylpyridine Chemical compound C1CC1C1=CC=CC=N1 SUHYUUVUQGJUJC-UHFFFAOYSA-N 0.000 description 1
• QWKKIWGATLDTLF-UHFFFAOYSA-N 2-decylpyridine Chemical compound CCCCCCCCCCC1=CC=CC=N1 QWKKIWGATLDTLF-UHFFFAOYSA-N 0.000 description 1
• VARNVZNSCHNTJI-UHFFFAOYSA-N 2-fluoro-1-methoxy-3-phenylbenzene Chemical group COC1=CC=CC(C=2C=CC=CC=2)=C1F VARNVZNSCHNTJI-UHFFFAOYSA-N 0.000 description 1
• DVJGNSPCQJBLRV-UHFFFAOYSA-N 2-fluoro-6-(2-methoxypyridine-4-carbonyl)benzonitrile Chemical compound C1=NC(OC)=CC(C(=O)C=2C(=C(F)C=CC=2)C#N)=C1 DVJGNSPCQJBLRV-UHFFFAOYSA-N 0.000 description 1
• GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 description 1
• SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
• FSTPMFASNVISBU-UHFFFAOYSA-N 2-methoxybenzonitrile Chemical compound COC1=CC=CC=C1C#N FSTPMFASNVISBU-UHFFFAOYSA-N 0.000 description 1
• RMHQDKYZXJVCME-UHFFFAOYSA-N 2-pyridin-4-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=NC=C1 RMHQDKYZXJVCME-UHFFFAOYSA-N 0.000 description 1
• HDBQZGJWHMCXIL-UHFFFAOYSA-N 3,7-dihydropurine-2-thione Chemical compound SC1=NC=C2NC=NC2=N1 HDBQZGJWHMCXIL-UHFFFAOYSA-N 0.000 description 1
• FQVHUXLJUAYVIU-UHFFFAOYSA-N 3-bromo-4-fluorobenzohydrazide Chemical compound NNC(=O)C1=CC=C(F)C(Br)=C1 FQVHUXLJUAYVIU-UHFFFAOYSA-N 0.000 description 1
• BBPZABXVRBFWGD-UHFFFAOYSA-N 3-bromo-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1Br BBPZABXVRBFWGD-UHFFFAOYSA-N 0.000 description 1
• YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
• CYWHLOXWVAWMFO-UHFFFAOYSA-N 3-sulfanyl-1h-pyridine-2-thione Chemical compound SC1=CC=CN=C1S CYWHLOXWVAWMFO-UHFFFAOYSA-N 0.000 description 1
• MTKKGHVQPVOXIL-UHFFFAOYSA-N 3h-isoindol-1-amine Chemical compound C1=CC=C2C(N)=NCC2=C1 MTKKGHVQPVOXIL-UHFFFAOYSA-N 0.000 description 1
• KCHQXPGUJBVNTN-UHFFFAOYSA-N 4,4-diphenylbut-3-en-2-one Chemical compound C=1C=CC=CC=1C(=CC(=O)C)C1=CC=CC=C1 KCHQXPGUJBVNTN-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• ZDFDINMHFLFYGQ-UHFFFAOYSA-N 4-(4-aminophenyl)-2-methoxyaniline Chemical compound C1=C(N)C(OC)=CC(C=2C=CC(N)=CC=2)=C1 ZDFDINMHFLFYGQ-UHFFFAOYSA-N 0.000 description 1
• NPUZZKZKHYZOEJ-UHFFFAOYSA-N 4-bromo-2-cyclopropylpyridine Chemical compound BrC1=CC=NC(C2CC2)=C1 NPUZZKZKHYZOEJ-UHFFFAOYSA-N 0.000 description 1
• JFBMFWHEXBLFCR-UHFFFAOYSA-N 4-bromo-2-methylpyridine Chemical compound CC1=CC(Br)=CC=N1 JFBMFWHEXBLFCR-UHFFFAOYSA-N 0.000 description 1
• SCOXFIBXWCCICG-UHFFFAOYSA-N 4-bromo-2-pyridin-2-ylpyridine Chemical compound BrC1=CC=NC(C=2N=CC=CC=2)=C1 SCOXFIBXWCCICG-UHFFFAOYSA-N 0.000 description 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
• OXUCGUHGNJQWMT-UHFFFAOYSA-N 4-methoxy-2-phenylpyridine Chemical compound COC1=CC=NC(C=2C=CC=CC=2)=C1 OXUCGUHGNJQWMT-UHFFFAOYSA-N 0.000 description 1
• MAGQVUXQRXLNGB-UHFFFAOYSA-N 5-bromo-2-fluorobenzamide Chemical compound NC(=O)C1=CC(Br)=CC=C1F MAGQVUXQRXLNGB-UHFFFAOYSA-N 0.000 description 1
• PEXAZYDITWXYNJ-UHFFFAOYSA-N 5-bromo-2-fluorobenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1F PEXAZYDITWXYNJ-UHFFFAOYSA-N 0.000 description 1
• GYCPLYCTMDTEPU-UHFFFAOYSA-N 5-bromopyrimidine Chemical compound BrC1=CN=CN=C1 GYCPLYCTMDTEPU-UHFFFAOYSA-N 0.000 description 1
• GEFRKIIMQLBMSS-UHFFFAOYSA-N 5-butyl-5-propylnonane Chemical compound CCCCC(CCC)(CCCC)CCCC GEFRKIIMQLBMSS-UHFFFAOYSA-N 0.000 description 1
• GLMXOYJTFKWRKZ-UHFFFAOYSA-N 6-bromo-2,4-dimethylpyridin-3-ol Chemical compound CC1=CC(Br)=NC(C)=C1O GLMXOYJTFKWRKZ-UHFFFAOYSA-N 0.000 description 1
• 231100000582 ATP assay Toxicity 0.000 description 1
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
• 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 1
• 241000254032 Acrididae Species 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 244000144730 Amygdalus persica Species 0.000 description 1
• 240000002900 Arthrospira platensis Species 0.000 description 1
• 235000016425 Arthrospira platensis Nutrition 0.000 description 1
• 101150058765 BACE1 gene Proteins 0.000 description 1
• VCCBCXVFGHTDQN-UODBTFMRSA-N BIII-890CL Chemical compound O([C@H](CN1[C@@H]2CC3=C(O)C=CC=C3[C@](C2(C)C)(C)CC1)C)CC1=CC=CC=C1 VCCBCXVFGHTDQN-UODBTFMRSA-N 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• WCAIAKXLBZFAEB-UHFFFAOYSA-N BrC1(NC=CC=C1)C1=C2C=CNC2=CC=C1 Chemical compound BrC1(NC=CC=C1)C1=C2C=CNC2=CC=C1 WCAIAKXLBZFAEB-UHFFFAOYSA-N 0.000 description 1
• GLGQQAGGCHHGRD-UHFFFAOYSA-N BrC1=NC(=NC(=C1)S)S Chemical compound BrC1=NC(=NC(=C1)S)S GLGQQAGGCHHGRD-UHFFFAOYSA-N 0.000 description 1
• 101100128142 Brevibacillus parabrevis lgrC gene Proteins 0.000 description 1
• UMSGKTJDUHERQW-UHFFFAOYSA-N Brotizolam Chemical compound C1=2C=C(Br)SC=2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl UMSGKTJDUHERQW-UHFFFAOYSA-N 0.000 description 1
• RZEUEZJTPYLEGF-UHFFFAOYSA-N C(CCCCC=S=O)CCCCN Chemical compound C(CCCCC=S=O)CCCCN RZEUEZJTPYLEGF-UHFFFAOYSA-N 0.000 description 1
• WOCMYYQHKOYUQW-UHFFFAOYSA-N C(CCCCCCCCC)C=1C=C(C=NC1)B(O)O Chemical compound C(CCCCCCCCC)C=1C=C(C=NC1)B(O)O WOCMYYQHKOYUQW-UHFFFAOYSA-N 0.000 description 1
• QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
• JTHFSYMKMQNMPX-UHFFFAOYSA-N CS1(S(NC=CC=C1)(C)(C)C)(C)C Chemical compound CS1(S(NC=CC=C1)(C)(C)C)(C)C JTHFSYMKMQNMPX-UHFFFAOYSA-N 0.000 description 1
• 101100279442 Caenorhabditis elegans egg-6 gene Proteins 0.000 description 1
• 101000898643 Candida albicans Vacuolar aspartic protease Proteins 0.000 description 1
• 101000898783 Candida tropicalis Candidapepsin Proteins 0.000 description 1
• 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
• 241000282994 Cervidae Species 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 235000001258 Cinchona calisaya Nutrition 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
• 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
• 101000898784 Cryphonectria parasitica Endothiapepsin Proteins 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical group C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
• 102000018832 Cytochromes Human genes 0.000 description 1
• 108010052832 Cytochromes Proteins 0.000 description 1
• 238000005361 D2 NMR spectroscopy Methods 0.000 description 1
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
• 241000042812 Divales Species 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 239000007818 Grignard reagent Substances 0.000 description 1
• WYCLKVQLVUQKNZ-UHFFFAOYSA-N Halazepam Chemical compound N=1CC(=O)N(CC(F)(F)F)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 WYCLKVQLVUQKNZ-UHFFFAOYSA-N 0.000 description 1
• 241000405147 Hermes Species 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010020850 Hyperthyroidism Diseases 0.000 description 1
• WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical compound O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 1
• 108010022337 Leucine Enkephalin Proteins 0.000 description 1
• 239000002841 Lewis acid Substances 0.000 description 1
• 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
• HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
• PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
• FHFZEKYDSVTYLL-UHFFFAOYSA-N Methomidate Chemical compound COC(=O)C1=CN=CN1C(C)C1=CC=CC=C1 FHFZEKYDSVTYLL-UHFFFAOYSA-N 0.000 description 1
• XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 1
• 229940123134 Nitric oxide inhibitor Drugs 0.000 description 1
• BZXAGHNXYKXHAK-UHFFFAOYSA-N O1CCOCC1.[Rh] Chemical compound O1CCOCC1.[Rh] BZXAGHNXYKXHAK-UHFFFAOYSA-N 0.000 description 1
• 244000131316 Panax pseudoginseng Species 0.000 description 1
• 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
• 235000003140 Panax quinquefolius Nutrition 0.000 description 1
• SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
• RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 1
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
• 235000006040 Prunus persica var persica Nutrition 0.000 description 1
• 244000097202 Rathbunia alamosensis Species 0.000 description 1
• 235000009776 Rathbunia alamosensis Nutrition 0.000 description 1
• 101000933133 Rhizopus niveus Rhizopuspepsin-1 Proteins 0.000 description 1
• 101000910082 Rhizopus niveus Rhizopuspepsin-2 Proteins 0.000 description 1
• 101000910079 Rhizopus niveus Rhizopuspepsin-3 Proteins 0.000 description 1
• 101000910086 Rhizopus niveus Rhizopuspepsin-4 Proteins 0.000 description 1
• 101000910088 Rhizopus niveus Rhizopuspepsin-5 Proteins 0.000 description 1
• 101000898773 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Saccharopepsin Proteins 0.000 description 1
• 241000239226 Scorpiones Species 0.000 description 1
• FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 239000005864 Sulphur Substances 0.000 description 1
• 239000004098 Tetracycline Substances 0.000 description 1
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
• LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
• 208000030886 Traumatic Brain injury Diseases 0.000 description 1
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
• 229920004890 Triton X-100 Polymers 0.000 description 1
• 239000013504 Triton X-100 Substances 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
• OBTZHKFZVSDGIF-UHFFFAOYSA-N [Bi].C1=CC=C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Bi].C1=CC=C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 OBTZHKFZVSDGIF-UHFFFAOYSA-N 0.000 description 1
• WFMRQEPYKQVDKS-UHFFFAOYSA-N [IH]1CCCCCCCC1 Chemical compound [IH]1CCCCCCCC1 WFMRQEPYKQVDKS-UHFFFAOYSA-N 0.000 description 1
• VJZSTRLBFHZZRR-UHFFFAOYSA-N [N].CCCCC Chemical compound [N].CCCCC VJZSTRLBFHZZRR-UHFFFAOYSA-N 0.000 description 1
• JUETYIBPJYYYRR-UHFFFAOYSA-N [Zn]C1CC1 Chemical class [Zn]C1CC1 JUETYIBPJYYYRR-UHFFFAOYSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
• 229960005164 acesulfame Drugs 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000012042 active reagent Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• BSKHPKMHTQYZBB-UHFFFAOYSA-N alpha-methylpyridine Natural products CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 230000002205 anti-dementic effect Effects 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 101150031224 app gene Proteins 0.000 description 1
• 229940059720 apra Drugs 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 229940039856 aricept Drugs 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• 229910001570 bauxite Inorganic materials 0.000 description 1
• 230000003796 beauty Effects 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000002619 bicyclic group Chemical group 0.000 description 1
• 210000000941 bile Anatomy 0.000 description 1
• IEPBPSSCIZTJIF-UHFFFAOYSA-N bis(2,2,2-trichloroethyl) carbonate Chemical compound ClC(Cl)(Cl)COC(=O)OCC(Cl)(Cl)Cl IEPBPSSCIZTJIF-UHFFFAOYSA-N 0.000 description 1
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
• 229910052797 bismuth Inorganic materials 0.000 description 1
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 229910021538 borax Inorganic materials 0.000 description 1
• 210000005013 brain tissue Anatomy 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 229960002802 bromocriptine Drugs 0.000 description 1
• OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
• CHIWXYAWZYPFJS-UHFFFAOYSA-N bromomethoxybenzene Chemical compound BrCOC1=CC=CC=C1 CHIWXYAWZYPFJS-UHFFFAOYSA-N 0.000 description 1
• 125000004799 bromophenyl group Chemical group 0.000 description 1
• 229960003051 brotizolam Drugs 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• WTURIZHKIYDUAN-UHFFFAOYSA-N butane-2-sulfinic acid Chemical compound CCC(C)S(O)=O WTURIZHKIYDUAN-UHFFFAOYSA-N 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
• 210000004899 c-terminal region Anatomy 0.000 description 1
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
• 150000001721 carbon Chemical group 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 125000002091 cationic group Chemical group 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 239000006285 cell suspension Substances 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 230000002490 cerebral effect Effects 0.000 description 1
• 210000003467 cheek Anatomy 0.000 description 1
• SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
• 238000012822 chemical development Methods 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 238000005660 chlorination reaction Methods 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
• 229960001076 chlorpromazine Drugs 0.000 description 1
• LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 238000004140 cleaning Methods 0.000 description 1
• 229940068796 clozaril Drugs 0.000 description 1
• 238000011278 co-treatment Methods 0.000 description 1
• 230000019771 cognition Effects 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 230000001609 comparable effect Effects 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 238000012790 confirmation Methods 0.000 description 1
• 238000011443 conventional therapy Methods 0.000 description 1
• 150000004696 coordination complex Chemical class 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
• 229950005056 crobenetine Drugs 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 239000011903 deuterated solvents‎ Substances 0.000 description 1
• 238000003745 diagnosis Methods 0.000 description 1
• DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 1
• LCSNDSFWVKMJCT-UHFFFAOYSA-N dicyclohexyl-(2-phenylphenyl)phosphane Chemical group C1CCCCC1P(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 LCSNDSFWVKMJCT-UHFFFAOYSA-N 0.000 description 1
• 150000001993 dienes Chemical class 0.000 description 1
• 235000019820 disodium diphosphate Nutrition 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 229930004069 diterpene Natural products 0.000 description 1
• 125000000567 diterpene group Chemical group 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 238000003182 dose-response assay Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 235000013399 edible fruits Nutrition 0.000 description 1
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 150000002085 enols Chemical class 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• HJOIHNLVBSAZKR-UHFFFAOYSA-N ethanamine;propan-2-ol Chemical compound CCN.CC(C)O HJOIHNLVBSAZKR-UHFFFAOYSA-N 0.000 description 1
• NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
• 229960001690 etomidate Drugs 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 230000005284 excitation Effects 0.000 description 1
• 229940108366 exelon Drugs 0.000 description 1
• 239000013604 expression vector Substances 0.000 description 1
• 238000009313 farming Methods 0.000 description 1
• 238000004401 flow injection analysis Methods 0.000 description 1
• 238000002866 fluorescence resonance energy transfer Methods 0.000 description 1
• 238000003682 fluorination reaction Methods 0.000 description 1
• 229960004038 fluvoxamine Drugs 0.000 description 1
• CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 229960003980 galantamine Drugs 0.000 description 1
• ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 235000008434 ginseng Nutrition 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 229960004198 guanidine Drugs 0.000 description 1
• ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 1
• 229960002158 halazepam Drugs 0.000 description 1
• 125000004404 heteroalkyl group Chemical group 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
• 238000005286 illumination Methods 0.000 description 1
• XMXHEBAFVSFQEX-UHFFFAOYSA-N iloperidone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 XMXHEBAFVSFQEX-UHFFFAOYSA-N 0.000 description 1
• 229960003162 iloperidone Drugs 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 239000003999 initiator Substances 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 238000007689 inspection Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
• 210000003127 knee Anatomy 0.000 description 1
• URLZCHNOLZSCCA-UHFFFAOYSA-N leu-enkephalin Chemical compound C=1C=C(O)C=CC=1CC(N)C(=O)NCC(=O)NCC(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=CC=C1 URLZCHNOLZSCCA-UHFFFAOYSA-N 0.000 description 1
• 150000007517 lewis acids Chemical class 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 125000005647 linker group Chemical group 0.000 description 1
• 239000007791 liquid phase Substances 0.000 description 1
• 229910000103 lithium hydride Inorganic materials 0.000 description 1
• 229910001416 lithium ion Inorganic materials 0.000 description 1
• OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
• 229960004033 lormetazepam Drugs 0.000 description 1
• 238000004020 luminiscence type Methods 0.000 description 1
• 230000002934 lysing effect Effects 0.000 description 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
• 229910052748 manganese Inorganic materials 0.000 description 1
• 239000011572 manganese Substances 0.000 description 1
• 230000008774 maternal effect Effects 0.000 description 1
• 230000003340 mental effect Effects 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 230000029052 metamorphosis Effects 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
• IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
• 229960002047 metomidate Drugs 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
• YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
• DZCCLNYLUGNUKQ-UHFFFAOYSA-N n-(4-nitrosophenyl)hydroxylamine Chemical compound ONC1=CC=C(N=O)C=C1 DZCCLNYLUGNUKQ-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229940033872 namenda Drugs 0.000 description 1
• 210000005036 nerve Anatomy 0.000 description 1
• 208000004296 neuralgia Diseases 0.000 description 1
• 208000021722 neuropathic pain Diseases 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 125000002347 octyl 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])[H] 0.000 description 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 150000002940 palladium Chemical class 0.000 description 1
• UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
• 229940098695 palmitic acid Drugs 0.000 description 1
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
• 230000001717 pathogenic effect Effects 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 125000005981 pentynyl group Chemical group 0.000 description 1
• 229940111202 pepsin Drugs 0.000 description 1
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
• 150000004965 peroxy acids Chemical class 0.000 description 1
• 239000002831 pharmacologic agent Substances 0.000 description 1
• 238000005191 phase separation Methods 0.000 description 1
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
• 229960000964 phenelzine Drugs 0.000 description 1
• 229960005382 phenolphthalein Drugs 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 238000007747 plating Methods 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 230000003449 preventive effect Effects 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 230000037452 priming Effects 0.000 description 1
• RIZGKEIRSQLIBK-UHFFFAOYSA-N prop-1-ene-1-thiol Chemical compound CC=CS RIZGKEIRSQLIBK-UHFFFAOYSA-N 0.000 description 1
• 230000000644 propagated effect Effects 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
• ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
• GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 238000005956 quaternization reaction Methods 0.000 description 1
• 229960000948 quinine Drugs 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 238000000163 radioactive labelling Methods 0.000 description 1
• RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 description 1
• 229960000245 rasagiline Drugs 0.000 description 1
• 229940051845 razadyne Drugs 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• MQGIGGJUPITZSE-UHFFFAOYSA-N reclazepam Chemical compound C12=CC(Cl)=CC=C2N(C=2OCC(=O)N=2)CCN=C1C1=CC=CC=C1Cl MQGIGGJUPITZSE-UHFFFAOYSA-N 0.000 description 1
• 229950004797 reclazepam Drugs 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 239000012925 reference material Substances 0.000 description 1
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 229960004136 rivastigmine Drugs 0.000 description 1
• VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 1
• 239000000932 sedative agent Substances 0.000 description 1
• 230000001624 sedative effect Effects 0.000 description 1
• 230000035807 sensation Effects 0.000 description 1
• 238000011125 single therapy Methods 0.000 description 1
• 229910001415 sodium ion Inorganic materials 0.000 description 1
• 239000004328 sodium tetraborate Substances 0.000 description 1
• 235000010339 sodium tetraborate Nutrition 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 238000001179 sorption measurement Methods 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 229940082787 spirulina Drugs 0.000 description 1
• KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
• 229910000080 stannane Inorganic materials 0.000 description 1
• 239000004575 stone Substances 0.000 description 1
• 239000012089 stop solution Substances 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 229960002317 succinimide Drugs 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 125000004434 sulfur atom Chemical group 0.000 description 1
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical class O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
• 235000018553 tannin Nutrition 0.000 description 1
• 239000001648 tannin Substances 0.000 description 1
• 229920001864 tannin Polymers 0.000 description 1
• 238000003419 tautomerization reaction Methods 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 229960002180 tetracycline Drugs 0.000 description 1
• 229930101283 tetracycline Natural products 0.000 description 1
• 235000019364 tetracycline Nutrition 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• 239000010936 titanium Substances 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 230000009261 transgenic effect Effects 0.000 description 1
• 108091005703 transmembrane proteins Proteins 0.000 description 1
• 102000035160 transmembrane proteins Human genes 0.000 description 1
• 230000009529 traumatic brain injury Effects 0.000 description 1
• GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
• UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
• 229960002415 trichloroethylene Drugs 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
• IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
• 229960001082 trimethoprim Drugs 0.000 description 1
• 229930191535 trisporin Natural products 0.000 description 1
• 210000001215 vagina Anatomy 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 239000000052 vinegar Substances 0.000 description 1
• 235000021419 vinegar Nutrition 0.000 description 1
• 239000002699 waste material Substances 0.000 description 1
• 229910052727 yttrium Inorganic materials 0.000 description 1
• VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
• IQIGRZVNRAMNTC-UHFFFAOYSA-M zinc;2-fluorobenzene-6-ide-1-carbonitrile;iodide Chemical compound I[Zn+].FC1=CC=C[C-]=C1C#N IQIGRZVNRAMNTC-UHFFFAOYSA-M 0.000 description 1