TW200845969A - Inhibitors of ion channels - Google Patents

Info

Publication number

TW200845969A

TW200845969A TW097110261A TW97110261A TW200845969A TW 200845969 A TW200845969 A TW 200845969A TW 097110261 A TW097110261 A TW 097110261A TW 97110261 A TW97110261 A TW 97110261A TW 200845969 A TW200845969 A TW 200845969A

Authority

TW

Taiwan

Prior art keywords

group

substituted

unsubstituted

compound

fluoro

Prior art date

2007-03-23

Links

• Espacenet
• Global Dossier
• Discuss

• 102000004310 Ion Channels Human genes 0.000 title description 6
• 239000003112 inhibitor Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 341
• 208000002193 Pain Diseases 0.000 claims abstract description 129
• 230000036407 pain Effects 0.000 claims abstract description 111
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
• 238000011282 treatment Methods 0.000 claims abstract description 34
• 201000010099 disease Diseases 0.000 claims abstract description 30
• 229940124530 sulfonamide Drugs 0.000 claims abstract description 17
• -1 cyano, hydroxy Chemical group 0.000 claims description 788
• 201000006417 multiple sclerosis Diseases 0.000 claims description 394
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 193
• 125000000217 alkyl group Chemical group 0.000 claims description 180
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 131
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 108
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 99
• 238000002360 preparation method Methods 0.000 claims description 93
• 150000003839 salts Chemical class 0.000 claims description 71
• 125000003118 aryl group Chemical group 0.000 claims description 65
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 65
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 55
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 50
• 239000012453 solvate Substances 0.000 claims description 49
• 150000001412 amines Chemical class 0.000 claims description 47
• 125000003545 alkoxy group Chemical group 0.000 claims description 46
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 37
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 35
• 208000024891 symptom Diseases 0.000 claims description 35
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
• 239000007789 gas Substances 0.000 claims description 32
• 125000001153 fluoro group Chemical group F* 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• 125000005843 halogen group Chemical group 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 125000004429 atom Chemical group 0.000 claims description 23
• 239000000126 substance Substances 0.000 claims description 23
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 23
• 239000000460 chlorine Substances 0.000 claims description 22
• 206010015037 epilepsy Diseases 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
• 208000011231 Crohn disease Diseases 0.000 claims description 18
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 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 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 208000020925 Bipolar disease Diseases 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 150000003456 sulfonamides Chemical class 0.000 claims description 16
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
• 208000028683 bipolar I disease Diseases 0.000 claims description 15
• 208000025307 bipolar depression Diseases 0.000 claims description 15
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 14
• 150000002923 oximes Chemical class 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 125000001475 halogen functional group Chemical group 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 13
• 239000011593 sulfur Substances 0.000 claims description 13
• 208000011580 syndromic disease Diseases 0.000 claims description 13
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 12
• 230000000622 irritating effect Effects 0.000 claims description 11
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 229910052707 ruthenium Inorganic materials 0.000 claims description 8
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
• 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims description 7
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 7
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 230000001568 sexual effect Effects 0.000 claims description 7
• ZVIQXFUBNNGOJY-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)benzaldehyde Chemical group FC1=CC(C=O)=CC=C1C(F)(F)F ZVIQXFUBNNGOJY-UHFFFAOYSA-N 0.000 claims description 6
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• 230000009172 bursting Effects 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000006612 decyloxy group Chemical group 0.000 claims description 6
• 230000007794 irritation Effects 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 5
• ILWFNKLXPUKLEP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)-2-fluorobenzene Chemical group FC1=CC(CCl)=CC=C1Cl ILWFNKLXPUKLEP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
• 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 5
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 5
• 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
• 229940077388 benzenesulfonate Drugs 0.000 claims description 5
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 5
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 4
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 4
• 125000006500 3-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC(F)(F)F)=C1[H])C([H])([H])* 0.000 claims description 4
• 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 4
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 4
• XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• 150000001454 anthracenes Chemical class 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
• 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
• 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 3
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
• 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 3
• 150000002545 isoxazoles Chemical class 0.000 claims description 3
• 238000005304 joining Methods 0.000 claims description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 3
• 150000003852 triazoles Chemical class 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 2
• OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical group C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
• 125000006185 3,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical compound CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 claims description 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
• 208000034189 Sclerosis Diseases 0.000 claims description 2
• 210000003296 saliva Anatomy 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
• 150000003573 thiols Chemical class 0.000 claims 4
• WGZYVHFXLPDNDL-UHFFFAOYSA-N 4-benzoyl-2-phenylpyrazole-3-carbonitrile Chemical compound C=1C=CC=CC=1C(=O)C(=C1C#N)C=NN1C1=CC=CC=C1 WGZYVHFXLPDNDL-UHFFFAOYSA-N 0.000 claims 3
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 2
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims 1
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims 1
• VCZQYTJRWNRPHF-UHFFFAOYSA-N 1,2-dioxin Chemical group O1OC=CC=C1 VCZQYTJRWNRPHF-UHFFFAOYSA-N 0.000 claims 1
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
• OFQXVHPYWBHEMD-UHFFFAOYSA-N 1-phenyl-3,7-dihydropurine-2,6-dione Chemical compound O=C1NC=2N=CNC=2C(=O)N1C1=CC=CC=C1 OFQXVHPYWBHEMD-UHFFFAOYSA-N 0.000 claims 1
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical group C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 1
• AKUSZFPCJFNRSZ-UHFFFAOYSA-N 3,4-dimethyl-1,2-oxazole Chemical compound CC1=CON=C1C AKUSZFPCJFNRSZ-UHFFFAOYSA-N 0.000 claims 1
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 1
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
• 125000005427 anthranyl group Chemical group 0.000 claims 1
• 125000001769 aryl amino group Chemical group 0.000 claims 1
• 125000005110 aryl thio group Chemical group 0.000 claims 1
• 125000003943 azolyl group Chemical group 0.000 claims 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
• 238000010367 cloning Methods 0.000 claims 1
• 125000004311 dioxin-2-yl group Chemical group [H]C1=C([H])OC(*)=C([H])O1 0.000 claims 1
• 125000005241 heteroarylamino group Chemical group 0.000 claims 1
• 125000005368 heteroarylthio group Chemical group 0.000 claims 1
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
• 125000006178 methyl benzyl group Chemical group 0.000 claims 1
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
• 229910052762 osmium Inorganic materials 0.000 claims 1
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
• 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
• 125000001701 trimethoxybenzyl group Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 212
• 239000000203 mixture Substances 0.000 abstract description 39
• 108010052164 Sodium Channels Proteins 0.000 abstract description 30
• 102000018674 Sodium Channels Human genes 0.000 abstract description 30
• 230000004907 flux Effects 0.000 abstract description 18
• 208000004296 neuralgia Diseases 0.000 abstract description 16
• 150000002500 ions Chemical class 0.000 abstract description 15
• 208000021722 neuropathic pain Diseases 0.000 abstract description 14
• 206010065390 Inflammatory pain Diseases 0.000 abstract description 11
• 208000000094 Chronic Pain Diseases 0.000 abstract description 8
• 108010053752 Voltage-Gated Sodium Channels Proteins 0.000 abstract description 7
• 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 abstract description 7
• 230000005764 inhibitory process Effects 0.000 abstract description 7
• 125000003107 substituted aryl group Chemical group 0.000 abstract description 3
• FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 abstract description 2
• 230000000903 blocking effect Effects 0.000 abstract description 2
• 229910001415 sodium ion Inorganic materials 0.000 abstract description 2
• 208000015114 central nervous system disease Diseases 0.000 abstract 1
• 230000002981 neuropathic effect Effects 0.000 abstract 1
• 208000027232 peripheral nervous system disease Diseases 0.000 abstract 1
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 260
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 67
• 235000019439 ethyl acetate Nutrition 0.000 description 61
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 51
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• 239000000243 solution Substances 0.000 description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
• 125000001041 indolyl group Chemical group 0.000 description 37
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
• 239000002904 solvent Substances 0.000 description 29
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 26
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 26
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 25
• 238000002953 preparative HPLC Methods 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 108091006146 Channels Proteins 0.000 description 23
• 230000000694 effects Effects 0.000 description 23
• 238000005160 1H NMR spectroscopy Methods 0.000 description 22
• 230000006378 damage Effects 0.000 description 22
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 20
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 20
• 239000002253 acid Substances 0.000 description 20
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• 239000005711 Benzoic acid Substances 0.000 description 16
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 16
• 206010036790 Productive cough Diseases 0.000 description 16
• 235000010233 benzoic acid Nutrition 0.000 description 16
• 229960004365 benzoic acid Drugs 0.000 description 16
• 208000014674 injury Diseases 0.000 description 16
• 210000003802 sputum Anatomy 0.000 description 16
• 208000024794 sputum Diseases 0.000 description 16
• 208000027418 Wounds and injury Diseases 0.000 description 15
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
• 229910052796 boron Inorganic materials 0.000 description 14
• 210000003169 central nervous system Anatomy 0.000 description 14
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 13
• 239000013058 crude material Substances 0.000 description 13
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 13
• 125000006239 protecting group Chemical group 0.000 description 13
• 229910052938 sodium sulfate Inorganic materials 0.000 description 13
• 235000011152 sodium sulphate Nutrition 0.000 description 13
• GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 12
• 238000004128 high performance liquid chromatography Methods 0.000 description 12
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 12
• 239000007787 solid Substances 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• 239000007864 aqueous solution Substances 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• 239000000651 prodrug Substances 0.000 description 11
• 229940002612 prodrug Drugs 0.000 description 11
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 229910052805 deuterium Inorganic materials 0.000 description 10
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 10
• 125000005842 heteroatom Chemical group 0.000 description 10
• 238000001727 in vivo Methods 0.000 description 10
• 230000000968 intestinal effect Effects 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 208000033808 peripheral neuropathy Diseases 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 241000894007 species Species 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 239000002090 nanochannel Substances 0.000 description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 description 9
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 9
• 229940067157 phenylhydrazine Drugs 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 239000012317 TBTU Substances 0.000 description 8
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 8
• 230000001154 acute effect Effects 0.000 description 8
• 208000005298 acute pain Diseases 0.000 description 8
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 8
• 201000001119 neuropathy Diseases 0.000 description 8
• 230000007823 neuropathy Effects 0.000 description 8
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 8
• 239000002244 precipitate Substances 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 239000003195 sodium channel blocking agent Substances 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 7
• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 7
• 208000008035 Back Pain Diseases 0.000 description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 7
• 230000004913 activation Effects 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 239000002775 capsule Substances 0.000 description 7
• 230000008859 change Effects 0.000 description 7
• 230000002757 inflammatory effect Effects 0.000 description 7
• 230000002401 inhibitory effect Effects 0.000 description 7
• 108090000623 proteins and genes Proteins 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
• 208000009935 visceral pain Diseases 0.000 description 7
• OIAPUNRSVALLCM-UHFFFAOYSA-N 4-(trifluoromethyl)decan-1-amine Chemical compound FC(C(CCCN)CCCCCC)(F)F OIAPUNRSVALLCM-UHFFFAOYSA-N 0.000 description 6
• PZOUSPYUWWUPPK-UHFFFAOYSA-N 4-methyl-1h-indole Chemical compound CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 206010058019 Cancer Pain Diseases 0.000 description 6
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
• 230000002378 acidificating effect Effects 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 230000006399 behavior Effects 0.000 description 6
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 6
• 125000004803 chlorobenzyl group Chemical group 0.000 description 6
• 230000001684 chronic effect Effects 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 208000035475 disorder Diseases 0.000 description 6
• 235000019441 ethanol Nutrition 0.000 description 6
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
• 125000000524 functional group Chemical group 0.000 description 6
• 238000002347 injection Methods 0.000 description 6
• 239000007924 injection Substances 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 239000002609 medium Substances 0.000 description 6
• 210000003205 muscle Anatomy 0.000 description 6
• 230000003040 nociceptive effect Effects 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 238000005191 phase separation Methods 0.000 description 6
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
• 230000035945 sensitivity Effects 0.000 description 6
• 210000001044 sensory neuron Anatomy 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• XXMFJKNOJSDQBM-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrate Chemical compound [OH3+].[O-]C(=O)C(F)(F)F XXMFJKNOJSDQBM-UHFFFAOYSA-N 0.000 description 5
• YUFAKSTVWOCFPO-UHFFFAOYSA-N 3-pyrazol-1-ylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(N2N=CC=C2)=C1 YUFAKSTVWOCFPO-UHFFFAOYSA-N 0.000 description 5
• 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 5
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• 206010019233 Headaches Diseases 0.000 description 5
• 108090000862 Ion Channels Proteins 0.000 description 5
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
• 229910021529 ammonia Inorganic materials 0.000 description 5
• 125000003710 aryl alkyl group Chemical group 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 238000004440 column chromatography Methods 0.000 description 5
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 206010012601 diabetes mellitus Diseases 0.000 description 5
• 239000000284 extract Substances 0.000 description 5
• 239000000835 fiber Substances 0.000 description 5
• 235000019253 formic acid Nutrition 0.000 description 5
• 230000006870 function Effects 0.000 description 5
• 230000002068 genetic effect Effects 0.000 description 5
• 231100000869 headache Toxicity 0.000 description 5
• 238000000338 in vitro Methods 0.000 description 5
• 230000001965 increasing effect Effects 0.000 description 5
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
• 210000002569 neuron Anatomy 0.000 description 5
• 230000001473 noxious effect Effects 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 201000008482 osteoarthritis Diseases 0.000 description 5
• 239000002245 particle Substances 0.000 description 5
• 230000002093 peripheral effect Effects 0.000 description 5
• 210000001428 peripheral nervous system Anatomy 0.000 description 5
• 230000004044 response Effects 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 5
• 210000001519 tissue Anatomy 0.000 description 5
• GVSMQKKMAYLKMM-UHFFFAOYSA-N 3-chloro-1h-indole Chemical group C1=CC=C2C(Cl)=CNC2=C1 GVSMQKKMAYLKMM-UHFFFAOYSA-N 0.000 description 4
• 241000282412 Homo Species 0.000 description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 4
• 208000019695 Migraine disease Diseases 0.000 description 4
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
• 241000699670 Mus sp. Species 0.000 description 4
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
• 102100031374 Sodium channel protein type 10 subunit alpha Human genes 0.000 description 4
• 102100033974 Sodium channel protein type 11 subunit alpha Human genes 0.000 description 4
• 102100031367 Sodium channel protein type 9 subunit alpha Human genes 0.000 description 4
• 239000007983 Tris buffer Substances 0.000 description 4
• 238000010521 absorption reaction Methods 0.000 description 4
• 230000009471 action Effects 0.000 description 4
• 206010003246 arthritis Diseases 0.000 description 4
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 4
• 239000007844 bleaching agent Substances 0.000 description 4
• 238000001514 detection method Methods 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 4
• 150000002431 hydrogen Chemical class 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 230000007246 mechanism Effects 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
• 239000011733 molybdenum Substances 0.000 description 4
• 229910052750 molybdenum Inorganic materials 0.000 description 4
• 210000005036 nerve Anatomy 0.000 description 4
• 210000000653 nervous system Anatomy 0.000 description 4
• 239000011347 resin Substances 0.000 description 4
• 229920005989 resin Polymers 0.000 description 4
• 230000001953 sensory effect Effects 0.000 description 4
• 230000002269 spontaneous effect Effects 0.000 description 4
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 4
• 210000001835 viscera Anatomy 0.000 description 4
• 229940075420 xanthine Drugs 0.000 description 4
• IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 3
• PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 3
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
• XAGZJIQIVXSURR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical group C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCCC1 XAGZJIQIVXSURR-UHFFFAOYSA-N 0.000 description 3
• XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
• BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• 101000654356 Homo sapiens Sodium channel protein type 10 subunit alpha Proteins 0.000 description 3
• 101000654386 Homo sapiens Sodium channel protein type 9 subunit alpha Proteins 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 206010028980 Neoplasm Diseases 0.000 description 3
• 208000005890 Neuroma Diseases 0.000 description 3
• 208000004550 Postoperative Pain Diseases 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• 229910000831 Steel Inorganic materials 0.000 description 3
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
• XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 3
• 230000002159 abnormal effect Effects 0.000 description 3
• 150000001413 amino acids Chemical class 0.000 description 3
• 235000011114 ammonium hydroxide Nutrition 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 206010003119 arrhythmia Diseases 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• 230000004071 biological effect Effects 0.000 description 3
• 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 3
• 229910052797 bismuth Inorganic materials 0.000 description 3
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
• 239000012267 brine Substances 0.000 description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 201000011510 cancer Diseases 0.000 description 3
• 235000013877 carbamide Nutrition 0.000 description 3
• 150000001721 carbon Chemical group 0.000 description 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 238000002512 chemotherapy Methods 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• 210000003414 extremity Anatomy 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 239000000796 flavoring agent Substances 0.000 description 3
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 3
• 235000013355 food flavoring agent Nutrition 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
• 239000011777 magnesium Substances 0.000 description 3
• 206010027599 migraine Diseases 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 210000004126 nerve fiber Anatomy 0.000 description 3
• 230000001537 neural effect Effects 0.000 description 3
• 230000004770 neurodegeneration Effects 0.000 description 3
• 230000000926 neurological effect Effects 0.000 description 3
• 230000007935 neutral effect Effects 0.000 description 3
• 210000000929 nociceptor Anatomy 0.000 description 3
• 210000000056 organ Anatomy 0.000 description 3
• IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 3
• AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 description 3
• 150000003254 radicals Chemical class 0.000 description 3
• 230000002285 radioactive effect Effects 0.000 description 3
• 230000009467 reduction Effects 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 230000033764 rhythmic process Effects 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 229940125794 sodium channel blocker Drugs 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
• 208000020431 spinal cord injury Diseases 0.000 description 3
• 239000010959 steel Substances 0.000 description 3
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
• 235000021286 stilbenes Nutrition 0.000 description 3
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 3
• 235000010269 sulphur dioxide Nutrition 0.000 description 3
• 238000001356 surgical procedure Methods 0.000 description 3
• CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 3
• 229950010357 tetrodotoxin Drugs 0.000 description 3
• CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 description 3
• 238000004809 thin layer chromatography Methods 0.000 description 3
• 125000004149 thio group Chemical group *S* 0.000 description 3
• 230000008733 trauma Effects 0.000 description 3
• IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
• RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
• UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
• PHLZUDXEBCQHKM-UHFFFAOYSA-N (3,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C(F)=C1 PHLZUDXEBCQHKM-UHFFFAOYSA-N 0.000 description 2
• HSNPBYKCCNMQNA-UHFFFAOYSA-N (4-chloro-3-fluorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(F)=C1 HSNPBYKCCNMQNA-UHFFFAOYSA-N 0.000 description 2
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 2
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
• FRUWMYWEARDNTC-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole Chemical compound C1C=CC=C2NCCC21 FRUWMYWEARDNTC-UHFFFAOYSA-N 0.000 description 2
• SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
• VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
• UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 description 2
• RXYADXXKYFJGHH-UHFFFAOYSA-N 2-(1,3-oxazol-2-yl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C1=NC=CO1 RXYADXXKYFJGHH-UHFFFAOYSA-N 0.000 description 2
• UTQSRYBPOURTOH-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C1=NC=CS1 UTQSRYBPOURTOH-UHFFFAOYSA-N 0.000 description 2
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
• GAWDUZDZORARJX-UHFFFAOYSA-N 3-(1,3-oxazol-2-yl)benzenesulfonamide Chemical compound O1C(=NC=C1)C=1C=C(C=CC=1)S(=O)(=O)N GAWDUZDZORARJX-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
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
• YBGBTGGBNZEUJS-UHFFFAOYSA-N 5-chloro-1,3-thiazole Chemical compound ClC1=CN=CS1 YBGBTGGBNZEUJS-UHFFFAOYSA-N 0.000 description 2
• MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 description 2
• 208000004998 Abdominal Pain Diseases 0.000 description 2
• 208000007848 Alcoholism Diseases 0.000 description 2
• 208000037157 Azotemia Diseases 0.000 description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
• XNLAILAJPGOCCH-UHFFFAOYSA-N CCCCCCCC(CCN)C(F)(F)F Chemical compound CCCCCCCC(CCN)C(F)(F)F XNLAILAJPGOCCH-UHFFFAOYSA-N 0.000 description 2
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
• 239000007821 HATU Substances 0.000 description 2
• 101000640020 Homo sapiens Sodium channel protein type 11 subunit alpha Proteins 0.000 description 2
• 101000684820 Homo sapiens Sodium channel protein type 3 subunit alpha Proteins 0.000 description 2
• 101000694017 Homo sapiens Sodium channel protein type 5 subunit alpha Proteins 0.000 description 2
• 101000654381 Homo sapiens Sodium channel protein type 8 subunit alpha Proteins 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• 208000004454 Hyperalgesia Diseases 0.000 description 2
• 208000035154 Hyperesthesia Diseases 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• 241000699666 Mus <mouse, genus> Species 0.000 description 2
• 208000000112 Myalgia Diseases 0.000 description 2
• 238000005481 NMR spectroscopy Methods 0.000 description 2
• 208000001294 Nociceptive Pain Diseases 0.000 description 2
• 241000283973 Oryctolagus cuniculus Species 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• 206010033645 Pancreatitis Diseases 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• 108010039918 Polylysine Proteins 0.000 description 2
• 206010036376 Postherpetic Neuralgia Diseases 0.000 description 2
• 208000025747 Rheumatic disease Diseases 0.000 description 2
• 101150080511 Scn9a gene Proteins 0.000 description 2
• 229910007161 Si(CH3)3 Inorganic materials 0.000 description 2
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
• 102100023720 Sodium channel protein type 3 subunit alpha Human genes 0.000 description 2
• 102100031371 Sodium channel protein type 8 subunit alpha Human genes 0.000 description 2
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
• 229910052770 Uranium Inorganic materials 0.000 description 2
• LKKOOHKPOMOOAI-UHFFFAOYSA-N [3-fluoro-4-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=C(OC(F)(F)F)C(F)=C1 LKKOOHKPOMOOAI-UHFFFAOYSA-N 0.000 description 2
• DBGROTRFYBSUTR-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=C(OC(F)(F)F)C=C1 DBGROTRFYBSUTR-UHFFFAOYSA-N 0.000 description 2
• PRDBLLIPPDOICK-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=C(C(F)(F)F)C=C1 PRDBLLIPPDOICK-UHFFFAOYSA-N 0.000 description 2
• 230000005856 abnormality Effects 0.000 description 2
• 230000036982 action potential Effects 0.000 description 2
• 230000006978 adaptation Effects 0.000 description 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 125000005037 alkyl phenyl group Chemical group 0.000 description 2
• 125000000304 alkynyl group Chemical group 0.000 description 2
• 230000000172 allergic effect Effects 0.000 description 2
• 239000000908 ammonium hydroxide Substances 0.000 description 2
• 230000006793 arrhythmia Effects 0.000 description 2
• 208000010668 atopic eczema Diseases 0.000 description 2
• 210000003050 axon Anatomy 0.000 description 2
• 230000003376 axonal effect Effects 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 2
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
• 239000012964 benzotriazole Substances 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
• 208000003295 carpal tunnel syndrome Diseases 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 210000000170 cell membrane Anatomy 0.000 description 2
• XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• 239000013068 control sample Substances 0.000 description 2
• MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 2
• 239000007822 coupling agent Substances 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• 230000001419 dependent effect Effects 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 239000012973 diazabicyclooctane Substances 0.000 description 2
• 125000006287 difluorobenzyl group Chemical group 0.000 description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
• 125000004212 difluorophenyl group Chemical group 0.000 description 2
• 239000000539 dimer Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 2
• 238000009826 distribution Methods 0.000 description 2
• 238000000132 electrospray ionisation Methods 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
• 238000003818 flash chromatography Methods 0.000 description 2
• 125000004175 fluorobenzyl group Chemical group 0.000 description 2
• 238000002309 gasification Methods 0.000 description 2
• 125000006277 halobenzyl group Chemical group 0.000 description 2
• 125000005059 halophenyl group Chemical group 0.000 description 2
• 238000013537 high throughput screening Methods 0.000 description 2
• 150000002429 hydrazines Chemical class 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• 208000003532 hypothyroidism Diseases 0.000 description 2
• 230000002989 hypothyroidism Effects 0.000 description 2
• 238000000099 in vitro assay Methods 0.000 description 2
• 230000004054 inflammatory process Effects 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• ZCYVEMRRCGMTRW-YPZZEJLDSA-N iodine-125 Chemical compound [125I] ZCYVEMRRCGMTRW-YPZZEJLDSA-N 0.000 description 2
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 2
• 125000000468 ketone group Chemical group 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 230000002045 lasting effect Effects 0.000 description 2
• 239000010410 layer Substances 0.000 description 2
• 125000005647 linker group Chemical group 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 239000003589 local anesthetic agent Substances 0.000 description 2
• 230000033001 locomotion Effects 0.000 description 2
• 239000007937 lozenge Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 238000004949 mass spectrometry Methods 0.000 description 2
• 229920000609 methyl cellulose Polymers 0.000 description 2
• 239000001923 methylcellulose Substances 0.000 description 2
• 235000010981 methylcellulose Nutrition 0.000 description 2
• 230000004048 modification Effects 0.000 description 2
• 238000012986 modification Methods 0.000 description 2
• 208000010125 myocardial infarction Diseases 0.000 description 2
• 108091008700 nociceptors Proteins 0.000 description 2
• ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
• 230000001717 pathogenic effect Effects 0.000 description 2
• 230000001575 pathological effect Effects 0.000 description 2
• 210000000578 peripheral nerve Anatomy 0.000 description 2
• 239000010452 phosphate Substances 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
• 239000006187 pill Substances 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 229920000656 polylysine Polymers 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 239000001294 propane Substances 0.000 description 2
• 230000001681 protective effect Effects 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 description 2
• 239000000523 sample Substances 0.000 description 2
• 210000002027 skeletal muscle Anatomy 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 210000000278 spinal cord Anatomy 0.000 description 2
• 239000003381 stabilizer Substances 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 230000001629 suppression Effects 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
• 229940124597 therapeutic agent Drugs 0.000 description 2
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 2
• 239000002562 thickening agent Substances 0.000 description 2
• 125000005309 thioalkoxy group Chemical group 0.000 description 2
• XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 2
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
• 230000000451 tissue damage Effects 0.000 description 2
• 231100000827 tissue damage Toxicity 0.000 description 2
• 239000003053 toxin Substances 0.000 description 2
• 231100000765 toxin Toxicity 0.000 description 2
• 108700012359 toxins Proteins 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000026683 transduction Effects 0.000 description 2
• 238000010361 transduction Methods 0.000 description 2
• 125000004360 trifluorophenyl group Chemical group 0.000 description 2
• 210000001170 unmyelinated nerve fiber Anatomy 0.000 description 2
• 208000009852 uremia Diseases 0.000 description 2
• 150000003673 urethanes Chemical class 0.000 description 2
• 239000002023 wood Substances 0.000 description 2
• RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
• GBLRQXKSCRCLBZ-YVQAASCFSA-N (1R,2S,1'R,2'S)-doxacurium Chemical compound COC1=C(OC)C(OC)=CC(C[C@H]2[N@+](CCC3=C2C(=C(OC)C(OC)=C3)OC)(C)CCCOC(=O)CCC(=O)OCCC[N@@+]2(C)[C@@H](C3=C(OC)C(OC)=C(OC)C=C3CC2)CC=2C=C(OC)C(OC)=C(OC)C=2)=C1 GBLRQXKSCRCLBZ-YVQAASCFSA-N 0.000 description 1
• AELCINSCMGFISI-BDAKNGLRSA-N (1S,2R)-tranylcypromine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1 AELCINSCMGFISI-BDAKNGLRSA-N 0.000 description 1
• ZPEFMSTTZXJOTM-RJUBDTSPSA-N (1S,2R)-tranylcypromine hydrochloride Chemical compound Cl.N[C@H]1C[C@@H]1C1=CC=CC=C1 ZPEFMSTTZXJOTM-RJUBDTSPSA-N 0.000 description 1
• KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 description 1
• PQCUDKMMPTXMAL-UHFFFAOYSA-N (2,6-difluorophenyl)methanamine Chemical compound NCC1=C(F)C=CC=C1F PQCUDKMMPTXMAL-UHFFFAOYSA-N 0.000 description 1
• VLPIATFUUWWMKC-SNVBAGLBSA-N (2r)-1-(2,6-dimethylphenoxy)propan-2-amine Chemical compound C[C@@H](N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-SNVBAGLBSA-N 0.000 description 1
• TWZJJFDOOZXNRO-SNVBAGLBSA-N (2s)-2-(ethylamino)-2-phenylethanol Chemical compound CCN[C@H](CO)C1=CC=CC=C1 TWZJJFDOOZXNRO-SNVBAGLBSA-N 0.000 description 1
• FREHVNZJGKCGSM-PPHPATTJSA-N (2s)-2-[(3-chlorophenoxy)methyl]pyrrolidine;hydrochloride Chemical compound Cl.ClC1=CC=CC(OC[C@H]2NCCC2)=C1 FREHVNZJGKCGSM-PPHPATTJSA-N 0.000 description 1
• VJNGGOMRUHYAMC-UHFFFAOYSA-N (3,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC(F)=C1 VJNGGOMRUHYAMC-UHFFFAOYSA-N 0.000 description 1
• WSHINYARADCBCP-NXEZZACHSA-N (3s,4r)-4-(4-fluorophenyl)oxolan-3-amine Chemical compound N[C@@H]1COC[C@@H]1C1=CC=C(F)C=C1 WSHINYARADCBCP-NXEZZACHSA-N 0.000 description 1
• HGRWHBQLRXWSLV-DEOSSOPVSA-N (4s)-3'-(3,6-dihydro-2h-pyran-5-yl)-1'-fluoro-7'-(3-fluoropyridin-2-yl)spiro[5h-1,3-oxazole-4,5'-chromeno[2,3-c]pyridine]-2-amine Chemical compound C1OC(N)=N[C@]21C1=CC(C=3COCCC=3)=NC(F)=C1OC1=CC=C(C=3C(=CC=CN=3)F)C=C12 HGRWHBQLRXWSLV-DEOSSOPVSA-N 0.000 description 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
• 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• DHBZRQXIRAEMRO-UHFFFAOYSA-N 1,1,2,2-tetramethylhydrazine Chemical compound CN(C)N(C)C DHBZRQXIRAEMRO-UHFFFAOYSA-N 0.000 description 1
• OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 1
• VJHTZTZXOKVQRN-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine Chemical compound NC1=NC=NS1 VJHTZTZXOKVQRN-UHFFFAOYSA-N 0.000 description 1
• YDVARACJVYZWSP-UHFFFAOYSA-N 1,2-oxazole-3-thione Chemical compound SC=1C=CON=1 YDVARACJVYZWSP-UHFFFAOYSA-N 0.000 description 1
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
• QHHHLHCCVDMOJI-UHFFFAOYSA-N 1,3-thiazol-4-amine Chemical compound NC1=CSC=N1 QHHHLHCCVDMOJI-UHFFFAOYSA-N 0.000 description 1
• KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
• QGCLEUGNYRXBMZ-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanamine Chemical compound CC(N)C1=CC=C(F)C=C1 QGCLEUGNYRXBMZ-UHFFFAOYSA-N 0.000 description 1
• ANCAJMAPVNINSB-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclopropan-1-amine Chemical compound C1=CC(OC)=CC=C1C1(N)CC1 ANCAJMAPVNINSB-UHFFFAOYSA-N 0.000 description 1
• FCSNJJHQKOTHIX-UHFFFAOYSA-N 1-chloroethyl formate Chemical compound CC(Cl)OC=O FCSNJJHQKOTHIX-UHFFFAOYSA-N 0.000 description 1
• KVGOXGQSTGQXDD-UHFFFAOYSA-N 1-decane-sulfonic-acid Chemical compound CCCCCCCCCCS(O)(=O)=O KVGOXGQSTGQXDD-UHFFFAOYSA-N 0.000 description 1
• 125000006039 1-hexenyl group Chemical group 0.000 description 1
• ROEYDCSPRIEHFH-UHFFFAOYSA-N 1-hydroxy-7-nitrobenzotriazole Chemical compound C1=CC([N+]([O-])=O)=C2N(O)N=NC2=C1 ROEYDCSPRIEHFH-UHFFFAOYSA-N 0.000 description 1
• CNSCXLZIKKHZND-UHFFFAOYSA-N 1-methyl-1,2,4-triazol-3-amine Chemical compound CN1C=NC(N)=N1 CNSCXLZIKKHZND-UHFFFAOYSA-N 0.000 description 1
• OKIDBHHMCXAYLN-UHFFFAOYSA-N 1-phenyl-n-(trifluoromethoxy)methanamine Chemical compound FC(F)(F)ONCC1=CC=CC=C1 OKIDBHHMCXAYLN-UHFFFAOYSA-N 0.000 description 1
• OYRBDGKUVUVWRI-UHFFFAOYSA-N 1-phenylcyclopropan-1-amine Chemical compound C=1C=CC=CC=1C1(N)CC1 OYRBDGKUVUVWRI-UHFFFAOYSA-N 0.000 description 1
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
• AXINVSXSGNSVLV-UHFFFAOYSA-N 1h-pyrazol-4-amine Chemical compound NC=1C=NNC=1 AXINVSXSGNSVLV-UHFFFAOYSA-N 0.000 description 1
• IANXAXNUNBAWBA-UHFFFAOYSA-N 2,2,3-trimethylundecane Chemical compound CCCCCCCCC(C)C(C)(C)C IANXAXNUNBAWBA-UHFFFAOYSA-N 0.000 description 1
• LMJDWRWZTXQWTI-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-indole Chemical compound C1CCC=C2NCCC21 LMJDWRWZTXQWTI-UHFFFAOYSA-N 0.000 description 1
• UKZJZMLGGSGZMI-UHFFFAOYSA-N 2,3,4,7,8,9-hexahydro-1h-purine Chemical compound N1CNC=C2NCNC21 UKZJZMLGGSGZMI-UHFFFAOYSA-N 0.000 description 1
• PNFJZLFNBKNFDT-UHFFFAOYSA-N 2,3-dimethyldecan-1-amine Chemical compound CCCCCCCC(C)C(C)CN PNFJZLFNBKNFDT-UHFFFAOYSA-N 0.000 description 1
• GXIWMXAAPLZOBY-UHFFFAOYSA-N 2-(1-phenylethylamino)ethanol Chemical compound OCCNC(C)C1=CC=CC=C1 GXIWMXAAPLZOBY-UHFFFAOYSA-N 0.000 description 1
• RZBOMSOHMOVUES-UHFFFAOYSA-N 2-(2-chlorophenyl)ethanamine Chemical compound NCCC1=CC=CC=C1Cl RZBOMSOHMOVUES-UHFFFAOYSA-N 0.000 description 1
• 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• SYNYZEPTKJHAMT-UHFFFAOYSA-N 2-(2-chlorophenyl)thiomorpholine Chemical compound ClC1=CC=CC=C1C1SCCNC1 SYNYZEPTKJHAMT-UHFFFAOYSA-N 0.000 description 1
• RIKUOLJPJNVTEP-UHFFFAOYSA-N 2-(2-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC=C1F RIKUOLJPJNVTEP-UHFFFAOYSA-N 0.000 description 1
• NOJCVVKIBLHAGW-UHFFFAOYSA-N 2-(2-fluorophenyl)pyrrolidine Chemical compound FC1=CC=CC=C1C1NCCC1 NOJCVVKIBLHAGW-UHFFFAOYSA-N 0.000 description 1
• RPCKHOCCYPQVAF-UHFFFAOYSA-N 2-(2-methoxyphenyl)morpholine Chemical compound COC1=CC=CC=C1C1OCCNC1 RPCKHOCCYPQVAF-UHFFFAOYSA-N 0.000 description 1
• TVSLNRQODQRVJZ-UHFFFAOYSA-N 2-(3,4,5-trifluorophenyl)acetonitrile Chemical group FC1=CC(CC#N)=CC(F)=C1F TVSLNRQODQRVJZ-UHFFFAOYSA-N 0.000 description 1
• QCIVXXIYXGRXBO-UHFFFAOYSA-N 2-(3,5-difluorophenyl)propan-2-amine;hydrochloride Chemical compound Cl.CC(C)(N)C1=CC(F)=CC(F)=C1 QCIVXXIYXGRXBO-UHFFFAOYSA-N 0.000 description 1
• NRHVNPYOTNGECT-UHFFFAOYSA-N 2-(3-chlorophenyl)ethanamine Chemical compound NCCC1=CC=CC(Cl)=C1 NRHVNPYOTNGECT-UHFFFAOYSA-N 0.000 description 1
• 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• RJFOLCUYDLFKFW-UHFFFAOYSA-N 2-(3-chlorophenyl)propan-2-amine Chemical compound CC(C)(N)C1=CC=CC(Cl)=C1 RJFOLCUYDLFKFW-UHFFFAOYSA-N 0.000 description 1
• AUCVZEYHEFAWHO-UHFFFAOYSA-N 2-(3-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC(F)=C1 AUCVZEYHEFAWHO-UHFFFAOYSA-N 0.000 description 1
• KSHXAAXEJWSEND-UHFFFAOYSA-N 2-(4-chlorophenoxy)ethanamine Chemical compound NCCOC1=CC=C(Cl)C=C1 KSHXAAXEJWSEND-UHFFFAOYSA-N 0.000 description 1
• SRXFXCKTIGELTI-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C=C1 SRXFXCKTIGELTI-UHFFFAOYSA-N 0.000 description 1
• FLACJAGRDZAFJF-UHFFFAOYSA-N 2-(4-chlorophenyl)propan-1-amine Chemical compound NCC(C)C1=CC=C(Cl)C=C1 FLACJAGRDZAFJF-UHFFFAOYSA-N 0.000 description 1
• JCUUNSQUTQELEZ-UHFFFAOYSA-N 2-(4-chlorophenyl)propan-2-amine Chemical compound CC(C)(N)C1=CC=C(Cl)C=C1 JCUUNSQUTQELEZ-UHFFFAOYSA-N 0.000 description 1
• CKLFJWXRWIQYOC-UHFFFAOYSA-N 2-(4-fluorophenyl)ethanamine Chemical compound NCCC1=CC=C(F)C=C1 CKLFJWXRWIQYOC-UHFFFAOYSA-N 0.000 description 1
• JNUNUMZEQFUFAM-UHFFFAOYSA-N 2-(decylamino)-1-phenylethanol Chemical compound CCCCCCCCCCNCC(O)C1=CC=CC=C1 JNUNUMZEQFUFAM-UHFFFAOYSA-N 0.000 description 1
• QBMFPMWNMHUVNH-UHFFFAOYSA-N 2-(piperidin-2-ylmethyl)pyridine Chemical compound C=1C=CC=NC=1CC1CCCCN1 QBMFPMWNMHUVNH-UHFFFAOYSA-N 0.000 description 1
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 description 1
• BPVYCXMGJPKOTQ-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]ethanamine Chemical compound NCCC1=CC=CC(C(F)(F)F)=C1 BPVYCXMGJPKOTQ-UHFFFAOYSA-N 0.000 description 1
• YEGWNHBRMASMGR-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]propan-2-amine Chemical compound CC(C)(N)C1=CC=CC(C(F)(F)F)=C1 YEGWNHBRMASMGR-UHFFFAOYSA-N 0.000 description 1
• BZZQAWGDEQZOOF-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]propan-2-amine Chemical compound CC(C)(N)C1=CC=C(C(F)(F)F)C=C1 BZZQAWGDEQZOOF-UHFFFAOYSA-N 0.000 description 1
• HALZSHRJUMADMG-UHFFFAOYSA-N 2-amino-2-(2-chlorophenyl)ethanol Chemical compound OCC(N)C1=CC=CC=C1Cl HALZSHRJUMADMG-UHFFFAOYSA-N 0.000 description 1
• JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
• VFHNHXVFSOEFFS-UHFFFAOYSA-N 2-ethyltriazol-4-amine Chemical compound CCN1N=CC(N)=N1 VFHNHXVFSOEFFS-UHFFFAOYSA-N 0.000 description 1
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
• IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 1
• LQZDYPHFVGRHKD-UHFFFAOYSA-N 2-methyl-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(C)=CC=C3C=CC2=C1 LQZDYPHFVGRHKD-UHFFFAOYSA-N 0.000 description 1
• VRESBNUEIKZECD-UHFFFAOYSA-N 2-methyltetrazole Chemical compound CN1N=CN=N1 VRESBNUEIKZECD-UHFFFAOYSA-N 0.000 description 1
• RQCBPOPQTLHDFC-UHFFFAOYSA-N 2-phenyl-1,3-oxazole Chemical compound C1=COC(C=2C=CC=CC=2)=N1 RQCBPOPQTLHDFC-UHFFFAOYSA-N 0.000 description 1
• KDFDOINBXBEOLZ-UHFFFAOYSA-N 2-phenylpropan-2-amine Chemical compound CC(C)(N)C1=CC=CC=C1 KDFDOINBXBEOLZ-UHFFFAOYSA-N 0.000 description 1
• QLDFMNWSPWEFIM-UHFFFAOYSA-N 2-phenyltetrazole Chemical compound N1=CN=NN1C1=CC=CC=C1 QLDFMNWSPWEFIM-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• DETCGQNBWKHTCQ-UHFFFAOYSA-N 3,4-difluoro-1h-indole Chemical compound C1=CC(F)=C2C(F)=CNC2=C1 DETCGQNBWKHTCQ-UHFFFAOYSA-N 0.000 description 1
• FICAQKBMCKEFDI-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole Chemical compound CC=1C=C(C)ON=1 FICAQKBMCKEFDI-UHFFFAOYSA-N 0.000 description 1
• NLDDLJBGRZJASZ-UHFFFAOYSA-N 3,5-dimethylpyridin-2-amine Chemical compound CC1=CN=C(N)C(C)=C1 NLDDLJBGRZJASZ-UHFFFAOYSA-N 0.000 description 1
• SSACMSYHGWVIKW-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C=2SC=CN=2)=C1 SSACMSYHGWVIKW-UHFFFAOYSA-N 0.000 description 1
• UKMRAVXQTUEGJX-UHFFFAOYSA-N 3-(4-fluorophenyl)thiomorpholine Chemical compound C1=CC(F)=CC=C1C1NCCSC1 UKMRAVXQTUEGJX-UHFFFAOYSA-N 0.000 description 1
• XLKBIUMAMUGELV-UHFFFAOYSA-N 3-(4-methylphenoxy)piperidine Chemical compound C1=CC(C)=CC=C1OC1CNCCC1 XLKBIUMAMUGELV-UHFFFAOYSA-N 0.000 description 1
• QUMLOVQFWVLNPX-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methyl]piperidine Chemical compound COC1=CC=CC=C1CC1CNCCC1 QUMLOVQFWVLNPX-UHFFFAOYSA-N 0.000 description 1
• UHJDGPCDHSTOCO-UHFFFAOYSA-N 3-[(3,5-difluorophenoxy)methyl]piperidine Chemical compound FC1=CC(F)=CC(OCC2CNCCC2)=C1 UHJDGPCDHSTOCO-UHFFFAOYSA-N 0.000 description 1
• MRDVNADGYFVSME-UHFFFAOYSA-N 3-[(4-fluorophenoxy)methyl]piperidine Chemical compound C1=CC(F)=CC=C1OCC1CNCCC1 MRDVNADGYFVSME-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• HFBLCYZEOGXHDP-UHFFFAOYSA-N 3-benzylpyrrolidine Chemical compound C=1C=CC=CC=1CC1CCNC1 HFBLCYZEOGXHDP-UHFFFAOYSA-N 0.000 description 1
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
• HGPUJQWMCPURNO-UHFFFAOYSA-N 3-ethyl-1,2,4-oxadiazol-5-amine Chemical compound CCC1=NOC(N)=N1 HGPUJQWMCPURNO-UHFFFAOYSA-N 0.000 description 1
• SCAHQZJCMQKAMD-UHFFFAOYSA-N 3-fluoro-2-hydrazinylbenzoic acid Chemical compound NNC1=C(F)C=CC=C1C(O)=O SCAHQZJCMQKAMD-UHFFFAOYSA-N 0.000 description 1
• MXNBDFWNYRNIBH-UHFFFAOYSA-N 3-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1 MXNBDFWNYRNIBH-UHFFFAOYSA-N 0.000 description 1
• BWKPANKVZIXCJJ-UHFFFAOYSA-N 3-fluorodecan-1-amine Chemical compound CCCCCCCC(F)CCN BWKPANKVZIXCJJ-UHFFFAOYSA-N 0.000 description 1
• CKDZUORTXOCQNI-UHFFFAOYSA-N 3-methoxy-1h-indole Chemical compound C1=CC=C2C(OC)=CNC2=C1 CKDZUORTXOCQNI-UHFFFAOYSA-N 0.000 description 1
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
• QDPNIJKUTWDGMV-UHFFFAOYSA-N 3-phenoxypiperidine Chemical compound C1CCNCC1OC1=CC=CC=C1 QDPNIJKUTWDGMV-UHFFFAOYSA-N 0.000 description 1
• VOMPAGYWXGOKBB-UHFFFAOYSA-N 3-propan-2-yloxy-1h-indole Chemical compound C1=CC=C2C(OC(C)C)=CNC2=C1 VOMPAGYWXGOKBB-UHFFFAOYSA-N 0.000 description 1
• 101150033839 4 gene Proteins 0.000 description 1
• DPKGMSYVZIXXBO-UHFFFAOYSA-N 4-(morpholine-4-carbonyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)N1CCOCC1 DPKGMSYVZIXXBO-UHFFFAOYSA-N 0.000 description 1
• YTVBZSLUNRYKID-UHFFFAOYSA-N 4-(trifluoromethyl)-1h-indole Chemical compound FC(F)(F)C1=CC=CC2=C1C=CN2 YTVBZSLUNRYKID-UHFFFAOYSA-N 0.000 description 1
• WEJHBEDHLLBJFW-UHFFFAOYSA-N 4-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=C(C(F)(F)F)C=C1 WEJHBEDHLLBJFW-UHFFFAOYSA-N 0.000 description 1
• FZGADESLAXNRDF-UHFFFAOYSA-N 4-(trifluoromethyl)pyrazol-1-amine Chemical compound NN1C=C(C(F)(F)F)C=N1 FZGADESLAXNRDF-UHFFFAOYSA-N 0.000 description 1
• SVLZRCRXNHITBY-UHFFFAOYSA-N 4-chloro-1h-indole Chemical compound ClC1=CC=CC2=C1C=CN2 SVLZRCRXNHITBY-UHFFFAOYSA-N 0.000 description 1
• RNOVGJWJVRESAA-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)phenol Chemical group OC1=CC=C(F)C=C1C(F)(F)F RNOVGJWJVRESAA-UHFFFAOYSA-N 0.000 description 1
• DGXWNDGLEOIEGT-UHFFFAOYSA-N 4-fluoroamphetamine Chemical compound CC(N)CC1=CC=C(F)C=C1 DGXWNDGLEOIEGT-UHFFFAOYSA-N 0.000 description 1
• HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 1
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
• ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• YCYWVZWDUQSUKY-UHFFFAOYSA-N 5-[(5-chloro-1,3-thiazol-2-yl)sulfamoyl]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1S(=O)(=O)NC1=NC=C(Cl)S1 YCYWVZWDUQSUKY-UHFFFAOYSA-N 0.000 description 1
• XCUGBJROAUARFC-UHFFFAOYSA-N 5-chloro-1,3-oxazole Chemical compound ClC1=CN=CO1 XCUGBJROAUARFC-UHFFFAOYSA-N 0.000 description 1
• FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 description 1
• HNOVETPPRHXNDM-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridin-2-amine Chemical compound NC1=CC=C2CCCC2=N1 HNOVETPPRHXNDM-UHFFFAOYSA-N 0.000 description 1
• VMMWPAGWAQYGPI-UHFFFAOYSA-N 6-decoxypyridin-3-amine Chemical compound CCCCCCCCCCOC1=CC=C(N)C=N1 VMMWPAGWAQYGPI-UHFFFAOYSA-N 0.000 description 1
• QVEUMXILHQDFLT-UHFFFAOYSA-N 6-sulfanyl-1h-pyridine-2-thione Chemical compound SC1=CC=CC(=S)N1 QVEUMXILHQDFLT-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
• FNEHAOQZWPHONV-UHFFFAOYSA-N 9h-carbazole;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C3=CC=CC=C3NC2=C1 FNEHAOQZWPHONV-UHFFFAOYSA-N 0.000 description 1
• 241000254032 Acrididae Species 0.000 description 1
• 206010000599 Acromegaly Diseases 0.000 description 1
• TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
• 201000004384 Alopecia Diseases 0.000 description 1
• 101710092462 Alpha-hemolysin Proteins 0.000 description 1
• 101710197219 Alpha-toxin Proteins 0.000 description 1
• KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 208000000044 Amnesia Diseases 0.000 description 1
• 208000019901 Anxiety disease Diseases 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
• 208000000412 Avitaminosis Diseases 0.000 description 1
• 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
• 235000017491 Bambusa tulda Nutrition 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 206010006002 Bone pain Diseases 0.000 description 1
• 206010048962 Brain oedema Diseases 0.000 description 1
• HUXRFEIFIFFWRF-UHFFFAOYSA-N C(=O)(O)[Mo](C(=O)O)(C(=O)O)(C(=O)O)(C(=O)O)C(=O)O Chemical compound C(=O)(O)[Mo](C(=O)O)(C(=O)O)(C(=O)O)(C(=O)O)C(=O)O HUXRFEIFIFFWRF-UHFFFAOYSA-N 0.000 description 1
• MVMYEPOVZHRLNS-UHFFFAOYSA-N C1=C2C(N=CN2)(N(C=N1)Cl)Cl Chemical compound C1=C2C(N=CN2)(N(C=N1)Cl)Cl MVMYEPOVZHRLNS-UHFFFAOYSA-N 0.000 description 1
• RYFJJBARKFEKOJ-UHFFFAOYSA-N CN(C1OC(=C(C(=C1C)C)C)C)C Chemical compound CN(C1OC(=C(C(=C1C)C)C)C)C RYFJJBARKFEKOJ-UHFFFAOYSA-N 0.000 description 1
• 101150010802 CVC2 gene Proteins 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 208000020597 Cardiac conduction disease Diseases 0.000 description 1
• 102100021391 Cationic amino acid transporter 3 Human genes 0.000 description 1
• 206010064012 Central pain syndrome Diseases 0.000 description 1
• 102000034573 Channels Human genes 0.000 description 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
• 208000017667 Chronic Disease Diseases 0.000 description 1
• GNSIIFXHKZWTFX-UHFFFAOYSA-N Cl.NC1=CC=2NC3=CC=CC(=C3C2C=C1)Cl Chemical compound Cl.NC1=CC=2NC3=CC=CC(=C3C2C=C1)Cl GNSIIFXHKZWTFX-UHFFFAOYSA-N 0.000 description 1
• VMEIIRWVUXZMCZ-UHFFFAOYSA-N ClC(CCCN)CCCCCC Chemical compound ClC(CCCN)CCCCCC VMEIIRWVUXZMCZ-UHFFFAOYSA-N 0.000 description 1
• MQWYDQZPAXCYNQ-UHFFFAOYSA-N ClC(CCN)CCCCCCC Chemical group ClC(CCN)CCCCCCC MQWYDQZPAXCYNQ-UHFFFAOYSA-N 0.000 description 1
• VQSCZZWYLMUTSH-UHFFFAOYSA-N ClC(CN)CCCCCCCC Chemical compound ClC(CN)CCCCCCCC VQSCZZWYLMUTSH-UHFFFAOYSA-N 0.000 description 1
• 208000006561 Cluster Headache Diseases 0.000 description 1
• 208000002881 Colic Diseases 0.000 description 1
• 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 1
• 206010011469 Crying Diseases 0.000 description 1
• 206010063057 Cystitis noninfective Diseases 0.000 description 1
• 241000238557 Decapoda Species 0.000 description 1
• 206010012218 Delirium Diseases 0.000 description 1
• 206010012289 Dementia Diseases 0.000 description 1
• 229920002307 Dextran Polymers 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical class CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
• 239000012594 Earle’s Balanced Salt Solution Substances 0.000 description 1
• 208000027534 Emotional disease Diseases 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 208000010201 Exanthema Diseases 0.000 description 1
• 206010016059 Facial pain Diseases 0.000 description 1
• 208000001640 Fibromyalgia Diseases 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 208000003078 Generalized Epilepsy Diseases 0.000 description 1
• 102000034615 Glial cell line-derived neurotrophic factor Human genes 0.000 description 1
• 108091010837 Glial cell line-derived neurotrophic factor Proteins 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
• 208000028782 Hereditary disease Diseases 0.000 description 1
• 208000029433 Herpesviridae infectious disease Diseases 0.000 description 1
• 101000631760 Homo sapiens Sodium channel protein type 1 subunit alpha Proteins 0.000 description 1
• 101000684826 Homo sapiens Sodium channel protein type 2 subunit alpha Proteins 0.000 description 1
• 101000693993 Homo sapiens Sodium channel protein type 4 subunit alpha Proteins 0.000 description 1
• 208000023105 Huntington disease Diseases 0.000 description 1
• 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• 206010021135 Hypovitaminosis Diseases 0.000 description 1
• 206010061216 Infarction Diseases 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
• 206010058031 Joint adhesion Diseases 0.000 description 1
• 208000012659 Joint disease Diseases 0.000 description 1
• 239000005909 Kieselgur Substances 0.000 description 1
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
• 229920000877 Melamine resin Polymers 0.000 description 1
• 208000026139 Memory disease Diseases 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• 208000019022 Mood disease Diseases 0.000 description 1
• 208000016285 Movement disease Diseases 0.000 description 1
• 208000010428 Muscle Weakness Diseases 0.000 description 1
• 206010028289 Muscle atrophy Diseases 0.000 description 1
• 206010049816 Muscle tightness Diseases 0.000 description 1
• 206010028372 Muscular weakness Diseases 0.000 description 1
• 208000036572 Myoclonic epilepsy Diseases 0.000 description 1
• 201000002481 Myositis Diseases 0.000 description 1
• 206010061533 Myotonia Diseases 0.000 description 1
• KKFGZKBFBZYLJH-UHFFFAOYSA-N N-ethyl-N-propan-2-ylpropan-2-amine hydrazine Chemical compound C(C)(C)N(CC)C(C)C.NN KKFGZKBFBZYLJH-UHFFFAOYSA-N 0.000 description 1
• QZKZOGYMVIALSK-UHFFFAOYSA-N N1C(=O)NC=2N=CNC2C1=O.C(C1=CC=CC=C1)(=O)O Chemical compound N1C(=O)NC=2N=CNC2C1=O.C(C1=CC=CC=C1)(=O)O QZKZOGYMVIALSK-UHFFFAOYSA-N 0.000 description 1
• IBKJLTXTNGQXQK-UHFFFAOYSA-N N1C(CC2CC=CC=C12)S Chemical compound N1C(CC2CC=CC=C12)S IBKJLTXTNGQXQK-UHFFFAOYSA-N 0.000 description 1
• WXRIYKLUJOBGKZ-UHFFFAOYSA-N N1C(N)NC(=O)C2NCCN=C12 Chemical compound N1C(N)NC(=O)C2NCCN=C12 WXRIYKLUJOBGKZ-UHFFFAOYSA-N 0.000 description 1
• SZFBVEOEDKZTQM-UHFFFAOYSA-N NC1=C(C(=NO1)S)S Chemical compound NC1=C(C(=NO1)S)S SZFBVEOEDKZTQM-UHFFFAOYSA-N 0.000 description 1
• 208000028389 Nerve injury Diseases 0.000 description 1
• 208000001738 Nervous System Trauma Diseases 0.000 description 1
• 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• CHIFTAQVXHNVRW-UHFFFAOYSA-N Nitrile-1H-Indole-3-carboxylic acid Natural products C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 description 1
• IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
• IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
• JHLJFDNKUFVMLV-UHFFFAOYSA-N OC1=CC=CC=2NN=NC21.NN Chemical compound OC1=CC=CC=2NN=NC21.NN JHLJFDNKUFVMLV-UHFFFAOYSA-N 0.000 description 1
• 208000008589 Obesity Diseases 0.000 description 1
• 206010068106 Occipital neuralgia Diseases 0.000 description 1
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
• LSGKMZLPZFPAIN-UHFFFAOYSA-N Oxime-1H-Indole-3-carboxaldehyde Natural products C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 description 1
• 208000000114 Pain Threshold Diseases 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
• 206010033647 Pancreatitis acute Diseases 0.000 description 1
• 206010033799 Paralysis Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 208000031481 Pathologic Constriction Diseases 0.000 description 1
• 208000000450 Pelvic Pain Diseases 0.000 description 1
• CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
• 208000004983 Phantom Limb Diseases 0.000 description 1
• 206010056238 Phantom pain Diseases 0.000 description 1
• 101710124951 Phospholipase C Proteins 0.000 description 1
• 244000082204 Phyllostachys viridis Species 0.000 description 1
• 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
• BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 229920002873 Polyethylenimine Polymers 0.000 description 1
• 239000004793 Polystyrene Substances 0.000 description 1
• 206010065016 Post-traumatic pain Diseases 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 208000003251 Pruritus Diseases 0.000 description 1
• 208000028017 Psychotic disease Diseases 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• 208000012322 Raynaud phenomenon Diseases 0.000 description 1
• 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 description 1
• 206010038419 Renal colic Diseases 0.000 description 1
• 101150110009 SCN11A gene Proteins 0.000 description 1
• 101150020107 SCN8A gene Proteins 0.000 description 1
• 108091006230 SLC7A3 Proteins 0.000 description 1
• ACZJRIUEWJQIRU-UHFFFAOYSA-N SN1N=C(N=N1)N Chemical compound SN1N=C(N=N1)N ACZJRIUEWJQIRU-UHFFFAOYSA-N 0.000 description 1
• 241000277284 Salvelinus fontinalis Species 0.000 description 1
• 240000000513 Santalum album Species 0.000 description 1
• 235000008632 Santalum album Nutrition 0.000 description 1
• 241000555745 Sciuridae Species 0.000 description 1
• 206010039710 Scleroderma Diseases 0.000 description 1
• 241000207929 Scutellaria Species 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• 206010070834 Sensitisation Diseases 0.000 description 1
• 208000019802 Sexually transmitted disease Diseases 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 102100028910 Sodium channel protein type 1 subunit alpha Human genes 0.000 description 1
• 101710134422 Sodium channel protein type 10 subunit alpha Proteins 0.000 description 1
• 101710102203 Sodium channel protein type 11 subunit alpha Proteins 0.000 description 1
• 102100023150 Sodium channel protein type 2 subunit alpha Human genes 0.000 description 1
• 102100027195 Sodium channel protein type 4 subunit alpha Human genes 0.000 description 1
• 102100027198 Sodium channel protein type 5 subunit alpha Human genes 0.000 description 1
• 101710097939 Sodium channel protein type 9 subunit alpha Proteins 0.000 description 1
• 239000005708 Sodium hypochlorite Substances 0.000 description 1
• 201000002661 Spondylitis Diseases 0.000 description 1
• 208000010040 Sprains and Strains Diseases 0.000 description 1
• 229930182558 Sterol Natural products 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 240000004460 Tanacetum coccineum Species 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 206010043269 Tension headache Diseases 0.000 description 1
• 208000008548 Tension-Type Headache Diseases 0.000 description 1
• 241000270666 Testudines Species 0.000 description 1
• HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 1
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
• 208000030886 Traumatic Brain injury Diseases 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
• 206010045171 Tumour pain Diseases 0.000 description 1
• 206010047095 Vascular pain Diseases 0.000 description 1
• 206010047115 Vasculitis Diseases 0.000 description 1
• 206010047571 Visual impairment Diseases 0.000 description 1
• ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
• TUPUHSXMDIWJQT-UHFFFAOYSA-N [3-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=CC(OC(F)(F)F)=C1 TUPUHSXMDIWJQT-UHFFFAOYSA-N 0.000 description 1
• YKNZTUQUXUXTLE-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(C(F)(F)F)=C1 YKNZTUQUXUXTLE-UHFFFAOYSA-N 0.000 description 1
• XYWYEOHNURYGGP-UHFFFAOYSA-N [3-fluoro-4-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=C(C(F)(F)F)C(F)=C1 XYWYEOHNURYGGP-UHFFFAOYSA-N 0.000 description 1
• HZDVQEUISWBXPV-UHFFFAOYSA-N [4-fluoro-3-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=C(F)C(C(F)(F)F)=C1 HZDVQEUISWBXPV-UHFFFAOYSA-N 0.000 description 1
• MCNHVBWLINLGIB-UHFFFAOYSA-N [Li].CC(CCCCCCCCCNCCCCCCCCCC(C)(C)C)(C)C Chemical compound [Li].CC(CCCCCCCCCNCCCCCCCCCC(C)(C)C)(C)C MCNHVBWLINLGIB-UHFFFAOYSA-N 0.000 description 1
• XSWALQKVYPLUJA-UHFFFAOYSA-N [Ru].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Ru].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 XSWALQKVYPLUJA-UHFFFAOYSA-N 0.000 description 1
• PMUIBVMKQVKHBE-UHFFFAOYSA-N [S].NC(N)=O Chemical compound [S].NC(N)=O PMUIBVMKQVKHBE-UHFFFAOYSA-N 0.000 description 1
• 210000000683 abdominal cavity Anatomy 0.000 description 1
• PMZXXNPJQYDFJX-UHFFFAOYSA-N acetonitrile;2,2,2-trifluoroacetic acid Chemical compound CC#N.OC(=O)C(F)(F)F PMZXXNPJQYDFJX-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 201000003229 acute pancreatitis Diseases 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229930013930 alkaloid Natural products 0.000 description 1
• 150000003797 alkaloid derivatives Chemical class 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 125000001118 alkylidene group Chemical group 0.000 description 1
• BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 1
• 239000002776 alpha toxin Substances 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 238000002266 amputation Methods 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 230000036506 anxiety Effects 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 230000002917 arthritic effect Effects 0.000 description 1
• 235000021311 artificial sweeteners Nutrition 0.000 description 1
• 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 239000003855 balanced salt solution Substances 0.000 description 1
• 239000011425 bamboo Substances 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 229960000686 benzalkonium chloride Drugs 0.000 description 1
• XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 description 1
• QQEXMHVHLWKOQT-UHFFFAOYSA-N benzene;formamide Chemical compound NC=O.C1=CC=CC=C1 QQEXMHVHLWKOQT-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
• 230000027455 binding Effects 0.000 description 1
• 238000002306 biochemical method Methods 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 230000005540 biological transmission Effects 0.000 description 1
• 238000001574 biopsy Methods 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000001124 body fluid Anatomy 0.000 description 1
• 239000010839 body fluid Substances 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 208000006752 brain edema Diseases 0.000 description 1
• 210000000133 brain stem Anatomy 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 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
• 125000004554 carbazol-2-yl group Chemical group C1=C(C=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
• MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 239000000679 carrageenan Substances 0.000 description 1
• 235000010418 carrageenan Nutrition 0.000 description 1
• 229920001525 carrageenan Polymers 0.000 description 1
• 229940113118 carrageenan Drugs 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 230000010261 cell growth Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 230000019522 cellular metabolic process Effects 0.000 description 1
• 210000001638 cerebellum Anatomy 0.000 description 1
• 239000007810 chemical reaction solvent Substances 0.000 description 1
• 238000005660 chlorination reaction Methods 0.000 description 1
• FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
• 229940106681 chloroacetic acid Drugs 0.000 description 1
• 239000011651 chromium Substances 0.000 description 1
• XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 208000018912 cluster headache syndrome Diseases 0.000 description 1
• 206010009887 colitis Diseases 0.000 description 1
• 238000002485 combustion reaction Methods 0.000 description 1
• 238000004891 communication Methods 0.000 description 1
• 238000010835 comparative analysis Methods 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 230000001276 controlling effect Effects 0.000 description 1
• 238000012937 correction Methods 0.000 description 1
• 239000006184 cosolvent Substances 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
• 150000004292 cyclic ethers Chemical class 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 150000001924 cycloalkanes Chemical class 0.000 description 1
• 125000000392 cycloalkenyl group Chemical group 0.000 description 1
• TXGVDTJWMZUNMP-UHFFFAOYSA-N cyclodecanamine Chemical compound NC1CCCCCCCCC1 TXGVDTJWMZUNMP-UHFFFAOYSA-N 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
• FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
• NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
• 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 230000006735 deficit Effects 0.000 description 1
• 238000012217 deletion Methods 0.000 description 1
• 230000037430 deletion Effects 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 238000001212 derivatisation Methods 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 150000004985 diamines Chemical class 0.000 description 1
• RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
• 229910000071 diazene Inorganic materials 0.000 description 1
• 239000012954 diazonium Substances 0.000 description 1
• 150000001989 diazonium salts Chemical class 0.000 description 1
• 238000006193 diazotization reaction Methods 0.000 description 1
• 125000006286 dichlorobenzyl group Chemical group 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 230000001079 digestive effect Effects 0.000 description 1
• 150000004683 dihydrates Chemical class 0.000 description 1
• 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 230000002222 downregulating effect Effects 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 201000006549 dyspepsia Diseases 0.000 description 1
• 201000009028 early myoclonic encephalopathy Diseases 0.000 description 1
• 229920001971 elastomer Polymers 0.000 description 1
• 238000003372 electrophysiological method Methods 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• 230000007613 environmental effect Effects 0.000 description 1
• 208000002854 epidermolysis bullosa simplex superficialis Diseases 0.000 description 1
• 230000034964 establishment of cell polarity Effects 0.000 description 1
• 238000010931 ester hydrolysis Methods 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 238000000105 evaporative light scattering detection Methods 0.000 description 1
• 201000005884 exanthem Diseases 0.000 description 1
• 210000003195 fascia Anatomy 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 210000003608 fece Anatomy 0.000 description 1
• 239000003337 fertilizer Substances 0.000 description 1
• 238000011049 filling Methods 0.000 description 1
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
• 238000001917 fluorescence detection Methods 0.000 description 1
• 239000007850 fluorescent dye Substances 0.000 description 1
• NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
• 125000001207 fluorophenyl group Chemical group 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 238000007306 functionalization reaction Methods 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 229960002870 gabapentin Drugs 0.000 description 1
• 229930182830 galactose Natural products 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 208000013069 generalized epilepsy with febrile seizures plus 1 Diseases 0.000 description 1
• 208000014204 generalized epilepsy with febrile seizures plus 2 Diseases 0.000 description 1
• 235000008434 ginseng Nutrition 0.000 description 1
• 230000002430 glycogenolytic effect Effects 0.000 description 1
• 125000003147 glycosyl group Chemical group 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 229920000591 gum Polymers 0.000 description 1
• JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
• 208000024963 hair loss Diseases 0.000 description 1
• 230000003676 hair loss Effects 0.000 description 1
• 125000004438 haloalkoxy group Chemical group 0.000 description 1
• 125000001188 haloalkyl group Chemical group 0.000 description 1
• 230000035876 healing Effects 0.000 description 1
• 208000016354 hearing loss disease Diseases 0.000 description 1
• 210000005003 heart tissue Anatomy 0.000 description 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
• 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
• 239000000833 heterodimer Substances 0.000 description 1
• 210000004394 hip joint Anatomy 0.000 description 1
• PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 238000001794 hormone therapy Methods 0.000 description 1
• 102000053391 human F Human genes 0.000 description 1
• 108700031895 human F Proteins 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
• 229940050526 hydroxyethylstarch Drugs 0.000 description 1
• 208000013403 hyperactivity Diseases 0.000 description 1
• 201000001993 idiopathic generalized epilepsy Diseases 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 230000036039 immunity Effects 0.000 description 1
• 238000009169 immunotherapy Methods 0.000 description 1
• 238000005462 in vivo assay Methods 0.000 description 1
• 230000007574 infarction Effects 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 230000000977 initiatory effect Effects 0.000 description 1
• 238000007917 intracranial administration 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
• 229940044173 iodine-125 Drugs 0.000 description 1
• 229940126181 ion channel inhibitor Drugs 0.000 description 1
• 235000000396 iron Nutrition 0.000 description 1
• 239000002085 irritant Substances 0.000 description 1
• 231100000021 irritant Toxicity 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
• OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• 230000000155 isotopic effect Effects 0.000 description 1
• 230000007803 itching Effects 0.000 description 1
• 210000001503 joint Anatomy 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229910052747 lanthanoid Inorganic materials 0.000 description 1
• 150000002602 lanthanoids Chemical class 0.000 description 1
• 229910052746 lanthanum Inorganic materials 0.000 description 1
• FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
• ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 1
• 201000010901 lateral sclerosis Diseases 0.000 description 1
• JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 description 1
• 230000013016 learning Effects 0.000 description 1
• 210000002414 leg Anatomy 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 231100000225 lethality Toxicity 0.000 description 1
• 229960004194 lidocaine Drugs 0.000 description 1
• 229910000103 lithium hydride Inorganic materials 0.000 description 1
• 229960005015 local anesthetics Drugs 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
• 239000001095 magnesium carbonate Substances 0.000 description 1
• 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• 230000006984 memory degeneration Effects 0.000 description 1
• 208000023060 memory loss Diseases 0.000 description 1
• 230000002175 menstrual effect Effects 0.000 description 1
• 229960001428 mercaptopurine Drugs 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 230000001394 metastastic effect Effects 0.000 description 1
• 208000037819 metastatic cancer Diseases 0.000 description 1
• 208000011575 metastatic malignant neoplasm Diseases 0.000 description 1
• 206010061289 metastatic neoplasm Diseases 0.000 description 1
• HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 1
• 229940102396 methyl bromide Drugs 0.000 description 1
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
• 125000006393 methylpyrimidinyl group Chemical group 0.000 description 1
• VLPIATFUUWWMKC-UHFFFAOYSA-N mexiletine Chemical compound CC(N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-UHFFFAOYSA-N 0.000 description 1
• 229960003404 mexiletine Drugs 0.000 description 1
• 230000003278 mimic effect Effects 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 210000002161 motor neuron Anatomy 0.000 description 1
• 208000005264 motor neuron disease Diseases 0.000 description 1
• 230000020763 muscle atrophy Effects 0.000 description 1
• 210000000663 muscle cell Anatomy 0.000 description 1
• 208000013465 muscle pain Diseases 0.000 description 1
• 201000000585 muscular atrophy Diseases 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 210000003007 myelin sheath Anatomy 0.000 description 1
• 230000003274 myotonic effect Effects 0.000 description 1
• BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 1
• DSWNRHCOGVRDOE-UHFFFAOYSA-N n,n-dimethylmethanimidamide Chemical compound CN(C)C=N DSWNRHCOGVRDOE-UHFFFAOYSA-N 0.000 description 1
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
• BRYXRHVIYJOZTE-UHFFFAOYSA-N n-(1,3-oxazol-2-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=NC=CO1 BRYXRHVIYJOZTE-UHFFFAOYSA-N 0.000 description 1
• AJWNYPNPXLNRAO-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=NC=CS1 AJWNYPNPXLNRAO-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
• 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• GNMNPHPUCWQGJK-UHFFFAOYSA-N n-methyl-1,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(NC)CC1=CC=CC=C1 GNMNPHPUCWQGJK-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 235000021096 natural sweeteners Nutrition 0.000 description 1
• 230000008764 nerve damage Effects 0.000 description 1
• 208000028412 nervous system injury Diseases 0.000 description 1
• 230000008904 neural response Effects 0.000 description 1
• 210000002241 neurite Anatomy 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 150000002828 nitro derivatives Chemical class 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• 239000002773 nucleotide Substances 0.000 description 1
• 125000003729 nucleotide group Chemical group 0.000 description 1
• OTTPWWFPWBCJBS-UHFFFAOYSA-N o-(trifluoromethyl)hydroxylamine Chemical compound NOC(F)(F)F OTTPWWFPWBCJBS-UHFFFAOYSA-N 0.000 description 1
• 235000020824 obesity Nutrition 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
• 239000003921 oil Substances 0.000 description 1
• 238000011275 oncology therapy Methods 0.000 description 1
• 229940127240 opiate Drugs 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000006186 oral dosage form Substances 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 230000008052 pain pathway Effects 0.000 description 1
• 230000037324 pain perception Effects 0.000 description 1
• 230000008058 pain sensation Effects 0.000 description 1
• 230000037040 pain threshold Effects 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
• 229940055076 parasympathomimetics choline ester Drugs 0.000 description 1
• 239000006201 parenteral dosage form Substances 0.000 description 1
• 208000035824 paresthesia Diseases 0.000 description 1
• 230000001314 paroxysmal effect Effects 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 230000007310 pathophysiology Effects 0.000 description 1
• 239000001814 pectin Substances 0.000 description 1
• 235000010987 pectin Nutrition 0.000 description 1
• 229920001277 pectin Polymers 0.000 description 1
• 208000008494 pericarditis Diseases 0.000 description 1
• 210000002856 peripheral neuron Anatomy 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 210000003800 pharynx Anatomy 0.000 description 1
• 125000004344 phenylpropyl group Chemical group 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 230000003863 physical function Effects 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 1
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
• 239000002798 polar solvent Substances 0.000 description 1
• 230000010287 polarization Effects 0.000 description 1
• 229920000768 polyamine Polymers 0.000 description 1
• 125000003367 polycyclic group Chemical group 0.000 description 1
• 229920000570 polyether Polymers 0.000 description 1
• 208000005987 polymyositis Diseases 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• 229920001451 polypropylene glycol Polymers 0.000 description 1
• 229920002223 polystyrene Polymers 0.000 description 1
• 239000011148 porous material Substances 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 229960003975 potassium Drugs 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
• 239000012286 potassium permanganate Substances 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• 230000000750 progressive effect Effects 0.000 description 1
• 230000000644 propagated effect Effects 0.000 description 1
• CDQXHVDVGLVACE-UHFFFAOYSA-N propan-2-amine Chemical compound [CH2]C(C)N CDQXHVDVGLVACE-UHFFFAOYSA-N 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
• 230000009979 protective mechanism Effects 0.000 description 1
• 238000000159 protein binding assay Methods 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 208000020016 psychiatric disease Diseases 0.000 description 1
• 230000005180 public health Effects 0.000 description 1
• NYIGEYYREVRXES-UHFFFAOYSA-N pyrazol-1-amine Chemical compound NN1C=CC=N1 NYIGEYYREVRXES-UHFFFAOYSA-N 0.000 description 1
• 150000003217 pyrazoles Chemical class 0.000 description 1
• 125000005412 pyrazyl group Chemical group 0.000 description 1
• 229940015367 pyrethrum Drugs 0.000 description 1
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
• 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
• 229960002026 pyrithione Drugs 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 150000003248 quinolines Chemical class 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 239000000700 radioactive tracer Substances 0.000 description 1
• 238000001959 radiotherapy Methods 0.000 description 1
• 206010037844 rash Diseases 0.000 description 1
• 238000011552 rat model Methods 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000008439 repair process Effects 0.000 description 1
• 230000000241 respiratory effect Effects 0.000 description 1
• 230000000717 retained effect Effects 0.000 description 1
• 238000004007 reversed phase HPLC Methods 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 230000000552 rheumatic effect Effects 0.000 description 1
• 238000011808 rodent model Methods 0.000 description 1
• 150000003303 ruthenium Chemical class 0.000 description 1
• 239000004576 sand Substances 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 201000000980 schizophrenia Diseases 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 210000000582 semen Anatomy 0.000 description 1
• 230000035807 sensation Effects 0.000 description 1
• 230000008313 sensitization Effects 0.000 description 1
• 230000020341 sensory perception of pain Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 125000005630 sialyl group Chemical group 0.000 description 1
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
• 229940126121 sodium channel inhibitor Drugs 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• LNDCCSBWZAQAAW-UHFFFAOYSA-M sodium hydrogen sulfate sulfuric acid Chemical compound [Na+].OS(O)(=O)=O.OS([O-])(=O)=O LNDCCSBWZAQAAW-UHFFFAOYSA-M 0.000 description 1
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 229940074404 sodium succinate Drugs 0.000 description 1
• ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
• 239000007909 solid dosage form Substances 0.000 description 1
• 238000000935 solvent evaporation Methods 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 210000003594 spinal ganglia Anatomy 0.000 description 1
• 210000001032 spinal nerve Anatomy 0.000 description 1
• 238000013125 spirometry Methods 0.000 description 1
• 210000000952 spleen Anatomy 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000036262 stenosis Effects 0.000 description 1
• 208000037804 stenosis Diseases 0.000 description 1
• 150000003432 sterols Chemical class 0.000 description 1
• 235000003702 sterols Nutrition 0.000 description 1
• 230000000638 stimulation Effects 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• 159000000008 strontium salts Chemical class 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000005750 substituted cyclic group Chemical group 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• OCKIJXFPIAVYSS-UHFFFAOYSA-N sulfanium;benzene;chloride Chemical compound [SH3+].[Cl-].C1=CC=CC=C1 OCKIJXFPIAVYSS-UHFFFAOYSA-N 0.000 description 1
• 125000004964 sulfoalkyl group Chemical group 0.000 description 1
• 125000000565 sulfonamide group Chemical group 0.000 description 1
• 239000004291 sulphur dioxide Substances 0.000 description 1
• 239000013589 supplement Substances 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 230000008961 swelling Effects 0.000 description 1
• 230000002889 sympathetic effect Effects 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 229940066765 systemic antihistamines substituted ethylene diamines Drugs 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 210000001138 tear Anatomy 0.000 description 1
• ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
• 229960002372 tetracaine Drugs 0.000 description 1
• TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 1
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• 210000001103 thalamus Anatomy 0.000 description 1
• 229940126585 therapeutic drug Drugs 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
• 150000003557 thiazoles Chemical class 0.000 description 1
• FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 230000001256 tonic effect Effects 0.000 description 1
• 208000004371 toothache Diseases 0.000 description 1
• 239000006208 topical dosage form Substances 0.000 description 1
• 230000024033 toxin binding Effects 0.000 description 1
• 230000002103 transcriptional effect Effects 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• 206010044652 trigeminal neuralgia Diseases 0.000 description 1
• 239000013638 trimer Substances 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1
• 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• 210000002700 urine Anatomy 0.000 description 1
• 208000019553 vascular disease Diseases 0.000 description 1
• 235000021419 vinegar Nutrition 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 230000009278 visceral effect Effects 0.000 description 1
• 239000011345 viscous material Substances 0.000 description 1
• 208000029257 vision disease Diseases 0.000 description 1
• 230000004393 visual impairment Effects 0.000 description 1
• 208000030401 vitamin deficiency disease Diseases 0.000 description 1
• 208000037975 work-related injury Diseases 0.000 description 1
• UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
• AXORVIZLPOGIRG-UHFFFAOYSA-N β-methylphenethylamine Chemical group NCC(C)C1=CC=CC=C1 AXORVIZLPOGIRG-UHFFFAOYSA-N 0.000 description 1