TW201444844A

TW201444844A - 經取代之黃嘌呤及使用其之方法

經取代之黃嘌呤及使用其之方法 Download PDF

Info

Publication number: TW201444844A
Authority: TW; Taiwan
Prior art keywords: dimethyl; compound; indole; lcms; alkyl
Prior art date: 2013-03-14

Application number

TW103108996A

Other languages

English (en)

Chinese (zh)

Inventor

Bertrand Chenard

Spencer David Kimball

Randall Gallaschun

Original Assignee

Hydra Biosciences Inc

Priority date

2013-03-14

Filing date

2014-03-13

Publication date

2014-12-01

2014-03-13 Application filed by Hydra Biosciences Inc filed Critical Hydra Biosciences Inc

2014-12-01 Publication of TW201444844A publication Critical patent/TW201444844A/zh

Links

238000000034 method Methods 0.000 title claims abstract description 102
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title description 7
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 392
239000000203 mixture Substances 0.000 claims abstract description 224
102000003621 TRPC5 Human genes 0.000 claims abstract description 80
101150042815 TRPC5 gene Proteins 0.000 claims abstract description 80
-1 C 1 -C 6 Alkoxy Chemical group 0.000 claims description 47
150000003839 salts Chemical class 0.000 claims description 47
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
125000001072 heteroaryl group Chemical group 0.000 claims description 25
230000001404 mediated effect Effects 0.000 claims description 20
125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 17
125000004104 aryloxy group Chemical group 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 14
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 12
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000004754 (C2-C12) dialkylamino group Chemical group 0.000 claims description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
208000015122 neurodegenerative disease Diseases 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
YHULXGUCQZFROV-UHFFFAOYSA-N sulfane;urea Chemical compound S.NC(N)=O YHULXGUCQZFROV-UHFFFAOYSA-N 0.000 claims description 5
125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
239000004202 carbamide Substances 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
206010015037 epilepsy Diseases 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
208000017169 kidney disease Diseases 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
KUADEFMPWIXDPI-UHFFFAOYSA-N 2-(sulfonylamino)guanidine Chemical compound S(=O)(=O)=NNC(=N)N KUADEFMPWIXDPI-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
VWDGQROCXXQAIF-UHFFFAOYSA-N S(=O)(=O)=NN(C(=O)N)NCCCCCCCCCC Chemical compound S(=O)(=O)=NN(C(=O)N)NCCCCCCCCCC VWDGQROCXXQAIF-UHFFFAOYSA-N 0.000 claims description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
125000004799 bromophenyl group Chemical group 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
229940124530 sulfonamide Drugs 0.000 claims description 2
150000003456 sulfonamides Chemical class 0.000 claims description 2
125000005864 sulfonamidyl group Chemical group 0.000 claims 1
102000004310 Ion Channels Human genes 0.000 abstract description 22
230000002401 inhibitory effect Effects 0.000 abstract description 7
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 478
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 344
230000014759 maintenance of location Effects 0.000 description 221
239000007787 solid Substances 0.000 description 183
235000019439 ethyl acetate Nutrition 0.000 description 143
239000000543 intermediate Substances 0.000 description 127
239000000243 solution Substances 0.000 description 96
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
208000002193 Pain Diseases 0.000 description 60
230000036407 pain Effects 0.000 description 56
238000006243 chemical reaction Methods 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 42
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
239000012044 organic layer Substances 0.000 description 36
239000000047 product Substances 0.000 description 34
239000003921 oil Substances 0.000 description 32
235000019198 oils Nutrition 0.000 description 32
230000000694 effects Effects 0.000 description 31
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
229910052938 sodium sulfate Inorganic materials 0.000 description 27
235000011152 sodium sulphate Nutrition 0.000 description 27
239000012043 crude product Substances 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 22
108090000862 Ion Channels Proteins 0.000 description 21
210000004027 cell Anatomy 0.000 description 21
229910000027 potassium carbonate Inorganic materials 0.000 description 21
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 20
125000000217 alkyl group Chemical group 0.000 description 18
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 18
201000010099 disease Diseases 0.000 description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
229920006395 saturated elastomer Polymers 0.000 description 18
239000011575 calcium Substances 0.000 description 17
238000002953 preparative HPLC Methods 0.000 description 17
230000002829 reductive effect Effects 0.000 description 17
238000011282 treatment Methods 0.000 description 17
230000006870 function Effects 0.000 description 16
239000002904 solvent Substances 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000003814 drug Substances 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
238000000746 purification Methods 0.000 description 14
238000010898 silica gel chromatography Methods 0.000 description 14
239000012267 brine Substances 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 12
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 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
239000000284 extract Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000011734 sodium Substances 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 11
241001465754 Metazoa Species 0.000 description 11
239000002253 acid Substances 0.000 description 11
229910052791 calcium Inorganic materials 0.000 description 11
230000006378 damage Effects 0.000 description 11
208000014674 injury Diseases 0.000 description 11
150000002500 ions Chemical class 0.000 description 11
239000012299 nitrogen atmosphere Substances 0.000 description 11
208000024891 symptom Diseases 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
235000019270 ammonium chloride Nutrition 0.000 description 10
239000013058 crude material Substances 0.000 description 10
229940079593 drug Drugs 0.000 description 10
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
150000002576 ketones Chemical class 0.000 description 10
239000012071 phase Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
208000027418 Wounds and injury Diseases 0.000 description 9
239000005557 antagonist Substances 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
239000012065 filter cake Substances 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
230000003834 intracellular effect Effects 0.000 description 8
239000000463 material Substances 0.000 description 8
210000001087 myotubule Anatomy 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
230000002265 prevention Effects 0.000 description 8
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
108091006146 Channels Proteins 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
229940122657 TRPC5 antagonist Drugs 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
229910052796 boron Inorganic materials 0.000 description 7
239000013078 crystal Substances 0.000 description 7
239000002552 dosage form Substances 0.000 description 7
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 7
239000010931 gold Substances 0.000 description 7
229910052737 gold Inorganic materials 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
ZHAKAIBZKYHXJS-UHFFFAOYSA-N 2-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=NC=CS1 ZHAKAIBZKYHXJS-UHFFFAOYSA-N 0.000 description 6
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
208000024827 Alzheimer disease Diseases 0.000 description 6
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
206010031009 Oral pain Diseases 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
238000009472 formulation Methods 0.000 description 6
230000014509 gene expression Effects 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
238000001727 in vivo Methods 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000000546 pharmaceutical excipient Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
239000012265 solid product Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
238000012360 testing method Methods 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
BAYTZPDBXASXLK-UHFFFAOYSA-N 2-chloro-5-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C(C=O)=C1 BAYTZPDBXASXLK-UHFFFAOYSA-N 0.000 description 5
BGQNOPFTJROKJE-UHFFFAOYSA-N 5,6-diamino-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(N)=C(N)C(=O)N(C)C1=O BGQNOPFTJROKJE-UHFFFAOYSA-N 0.000 description 5
208000000044 Amnesia Diseases 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 5
206010010904 Convulsion Diseases 0.000 description 5
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 5
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000002168 alkylating agent Substances 0.000 description 5
229940100198 alkylating agent Drugs 0.000 description 5
201000011510 cancer Diseases 0.000 description 5
125000005594 diketone group Chemical group 0.000 description 5
WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 5
210000003414 extremity Anatomy 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
230000004907 flux Effects 0.000 description 5
239000005457 ice water Substances 0.000 description 5
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239000000651 prodrug Substances 0.000 description 5
229940002612 prodrug Drugs 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
208000011580 syndromic disease Diseases 0.000 description 5
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 4
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
UJAFGNAOINNEKQ-UHFFFAOYSA-N 4-chloro-3-hydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC=C1Cl UJAFGNAOINNEKQ-UHFFFAOYSA-N 0.000 description 4
208000019901 Anxiety disease Diseases 0.000 description 4
108091005462 Cation channels Proteins 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
208000004454 Hyperalgesia Diseases 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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