SK287673B6 - Derivát N-alkoxyalkyl-N,N-dialkylamínu, liečivo obsahujúce tento derivát a jeho použitie - Google Patents
Derivát N-alkoxyalkyl-N,N-dialkylamínu, liečivo obsahujúce tento derivát a jeho použitie Download PDFInfo
- Publication number
- SK287673B6 SK287673B6 SK1781-2001A SK17812001A SK287673B6 SK 287673 B6 SK287673 B6 SK 287673B6 SK 17812001 A SK17812001 A SK 17812001A SK 287673 B6 SK287673 B6 SK 287673B6
- Authority
- SK
- Slovakia
- Prior art keywords
- ethyl
- thiophen
- benzo
- compound
- formula
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- -1 amino, hydroxyl Chemical group 0.000 claims description 459
- 229910052757 nitrogen Inorganic materials 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 abstract description 10
- 230000008929 regeneration Effects 0.000 abstract description 10
- 238000011069 regeneration method Methods 0.000 abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
- 230000000141 anti-hypoxic effect Effects 0.000 abstract description 5
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 206010056677 Nerve degeneration Diseases 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 473
- 150000001875 compounds Chemical class 0.000 description 301
- 239000000203 mixture Substances 0.000 description 189
- 239000000243 solution Substances 0.000 description 188
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 131
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 130
- 239000012044 organic layer Substances 0.000 description 130
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 124
- 238000006243 chemical reaction Methods 0.000 description 106
- 239000002904 solvent Substances 0.000 description 106
- 238000000034 method Methods 0.000 description 102
- 235000002639 sodium chloride Nutrition 0.000 description 98
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 86
- 230000002829 reductive effect Effects 0.000 description 86
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 84
- 239000011541 reaction mixture Substances 0.000 description 80
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 79
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 75
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 68
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 67
- 229920006395 saturated elastomer Polymers 0.000 description 67
- 238000004519 manufacturing process Methods 0.000 description 65
- 239000011780 sodium chloride Substances 0.000 description 64
- 239000000047 product Substances 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- 238000004440 column chromatography Methods 0.000 description 48
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 46
- 239000003480 eluent Substances 0.000 description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 45
- 239000003921 oil Substances 0.000 description 45
- 235000019198 oils Nutrition 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
- 238000001816 cooling Methods 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
- 101100020289 Xenopus laevis koza gene Proteins 0.000 description 34
- 238000001914 filtration Methods 0.000 description 34
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
- 239000013078 crystal Substances 0.000 description 33
- 239000000126 substance Substances 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000002585 base Substances 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
- 238000006722 reduction reaction Methods 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 238000003756 stirring Methods 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 125000005605 benzo group Chemical group 0.000 description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 235000006408 oxalic acid Nutrition 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 229910000027 potassium carbonate Inorganic materials 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 210000002569 neuron Anatomy 0.000 description 15
- JVJFIQYAHPMBBX-FNORWQNLSA-N (E)-4-hydroxynon-2-enal Chemical compound CCCCCC(O)\C=C\C=O JVJFIQYAHPMBBX-FNORWQNLSA-N 0.000 description 14
- JVJFIQYAHPMBBX-UHFFFAOYSA-N 4-hydroxynonenal Chemical compound CCCCCC(O)C=CC=O JVJFIQYAHPMBBX-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- HSTMOQBQLSNAHS-UHFFFAOYSA-N 2-[2-(1-benzothiophen-7-yl)ethoxy]-1-piperidin-1-ylethanone Chemical compound C=1C=CC=2C=CSC=2C=1CCOCC(=O)N1CCCCC1 HSTMOQBQLSNAHS-UHFFFAOYSA-N 0.000 description 13
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-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
- 235000011054 acetic acid Nutrition 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- 230000030833 cell death Effects 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- KZHKDMHZEZRBNG-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound OCCN(C)CCOCCC1=CC=C2SC=CC2=C1 KZHKDMHZEZRBNG-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 150000002902 organometallic compounds Chemical class 0.000 description 9
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 150000003462 sulfoxides Chemical class 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- 108010025020 Nerve Growth Factor Proteins 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 8
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 8
- 210000004556 brain Anatomy 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000008103 glucose Substances 0.000 description 8
- 150000008282 halocarbons Chemical class 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Chemical group 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 229960004592 isopropanol Drugs 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- 208000024827 Alzheimer disease Diseases 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 210000004027 cell Anatomy 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
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 150000002390 heteroarenes Chemical class 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 229940032147 starch Drugs 0.000 description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
- 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 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 230000002140 halogenating effect Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 210000003497 sciatic nerve Anatomy 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- IWOUGNGMKHMFEY-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]acetic acid Chemical compound OC(=O)COCCC1=CC=C2SC=CC2=C1 IWOUGNGMKHMFEY-UHFFFAOYSA-N 0.000 description 4
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- SNDVQGFYCMPWHB-UHFFFAOYSA-N 3-[2-(1-benzothiophen-5-yl)ethoxy]-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCOCCC1=CC=C2SC=CC2=C1 SNDVQGFYCMPWHB-UHFFFAOYSA-N 0.000 description 4
- 206010012289 Dementia Diseases 0.000 description 4
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 102000015336 Nerve Growth Factor Human genes 0.000 description 4
- 102000007072 Nerve Growth Factors Human genes 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 210000001161 mammalian embryo Anatomy 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229940053128 nerve growth factor Drugs 0.000 description 4
- 239000003900 neurotrophic factor Substances 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- BKMCUGFGPQNYHG-RSAXXLAASA-N (1r)-1-(1-benzothiophen-5-yl)-2-[2-(diethylamino)ethoxy]ethanol;hydrochloride Chemical compound Cl.CCN(CC)CCOC[C@H](O)C1=CC=C2SC=CC2=C1 BKMCUGFGPQNYHG-RSAXXLAASA-N 0.000 description 3
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 3
- DSZAQLDIEKUEMB-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)ethanol Chemical compound OCCC1=CC=C2SC=CC2=C1 DSZAQLDIEKUEMB-UHFFFAOYSA-N 0.000 description 3
- 125000000681 2-(2-naphthyl)ethoxy group Chemical group [H]C1=C([H])C2=C(C([H])=C1[H])C([H])=C(C([H])=C2[H])C([H])([H])C([H])([H])O* 0.000 description 3
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 3
- XKOOWVWWNGFALN-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOCCC1=CC=C2SC=CC2=C1 XKOOWVWWNGFALN-UHFFFAOYSA-N 0.000 description 3
- RNMBQTDSBURPAX-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCOCCC1=CC=C2SC=CC2=C1 RNMBQTDSBURPAX-UHFFFAOYSA-N 0.000 description 3
- QRWRBWWZPLBRFW-UHFFFAOYSA-N 2-[2-[2-(2-fluoro-1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound OCCN(C)CCOCCC1=CC=C2SC(F)=CC2=C1 QRWRBWWZPLBRFW-UHFFFAOYSA-N 0.000 description 3
- YOGDADIOTVLDRK-UHFFFAOYSA-N 2-[2-[2-(6-fluoro-1-benzothiophen-7-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound OCCN(C)CCOCCC1=C(F)C=CC2=C1SC=C2 YOGDADIOTVLDRK-UHFFFAOYSA-N 0.000 description 3
- SMMTXNBSKDZJOH-UHFFFAOYSA-N 2-[2-[2-(6-methoxy-1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound C1=C(CCOCCN(C)CCO)C(OC)=CC2=C1C=CS2 SMMTXNBSKDZJOH-UHFFFAOYSA-N 0.000 description 3
- VZHMWHUWPOQCSD-UHFFFAOYSA-N 2-[methyl-[2-(2-quinoxalin-6-ylethoxy)ethyl]amino]ethanol Chemical compound N1=CC=NC2=CC(CCOCCN(CCO)C)=CC=C21 VZHMWHUWPOQCSD-UHFFFAOYSA-N 0.000 description 3
- WDGHDAWIKLQWGF-UHFFFAOYSA-N 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene Chemical compound ClCCCOCCC1=CC=C2SC=CC2=C1 WDGHDAWIKLQWGF-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229940124532 absorption promoter Drugs 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 230000003925 brain function Effects 0.000 description 3
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 201000010901 lateral sclerosis Diseases 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 208000005264 motor neuron disease Diseases 0.000 description 3
- 201000001119 neuropathy Diseases 0.000 description 3
- 230000007823 neuropathy Effects 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 208000033808 peripheral neuropathy Diseases 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229960004029 silicic acid Drugs 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000003509 tertiary alcohols Chemical class 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 2
- YXFOZOTYCKVYJD-UHFFFAOYSA-N 1-[2-(1-benzothiophen-5-yl)ethoxy]propan-2-one Chemical compound CC(=O)COCCC1=CC=C2SC=CC2=C1 YXFOZOTYCKVYJD-UHFFFAOYSA-N 0.000 description 2
- OBAAOEHJZGBUHP-UHFFFAOYSA-N 1-[2-(1-benzothiophen-5-yl)ethoxy]propan-2-yl methanesulfonate Chemical compound CS(=O)(=O)OC(C)COCCC1=CC=C2SC=CC2=C1 OBAAOEHJZGBUHP-UHFFFAOYSA-N 0.000 description 2
- HSVTZSKCODYSAC-UHFFFAOYSA-N 1-[5-[2-[2-(diethylamino)ethoxy]ethyl]-2-methoxyphenyl]ethanone Chemical compound CCN(CC)CCOCCC1=CC=C(OC)C(C(C)=O)=C1 HSVTZSKCODYSAC-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- NANZJLLIORBGBU-UHFFFAOYSA-N 2-(1-benzothiophen-6-yl)ethanol Chemical compound OCCC1=CC=C2C=CSC2=C1 NANZJLLIORBGBU-UHFFFAOYSA-N 0.000 description 2
- DBNJNULROFTWED-UHFFFAOYSA-N 2-(2-quinoxalin-6-ylethoxy)ethanol Chemical compound N1=CC=NC2=CC(CCOCCO)=CC=C21 DBNJNULROFTWED-UHFFFAOYSA-N 0.000 description 2
- PYIHMQLSWPMEDY-UHFFFAOYSA-N 2-(3-acetyl-4-methoxyphenyl)ethyl acetate Chemical compound COC1=CC=C(CCOC(C)=O)C=C1C(C)=O PYIHMQLSWPMEDY-UHFFFAOYSA-N 0.000 description 2
- RJLOOVKANNAFQX-UHFFFAOYSA-N 2-(6-fluoro-7-methoxy-1-benzothiophen-5-yl)acetic acid Chemical compound COC1=C(F)C(CC(O)=O)=CC2=C1SC=C2 RJLOOVKANNAFQX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VECFHDYTJJOJEA-UHFFFAOYSA-N 2-[1-[2-(1-benzothiophen-5-yl)ethoxy]propan-2-yl-methylamino]ethanol Chemical compound OCCN(C)C(C)COCCC1=CC=C2SC=CC2=C1 VECFHDYTJJOJEA-UHFFFAOYSA-N 0.000 description 2
- KTMFDJUGBZNYFM-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOCCC1=CC=C2OCOC2=C1 KTMFDJUGBZNYFM-UHFFFAOYSA-N 0.000 description 2
- VPHNBXPSROZWHG-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCC1=CC=C2OCOC2=C1 VPHNBXPSROZWHG-UHFFFAOYSA-N 0.000 description 2
- HDWVUWQAOATTEJ-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethoxy]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCOCCC1=CC=C2OCOC2=C1 HDWVUWQAOATTEJ-UHFFFAOYSA-N 0.000 description 2
- DLGRIBUCZODISL-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-1-piperidin-1-ylethanone Chemical compound C=1C=C2SC=CC2=CC=1CCOCC(=O)N1CCCCC1 DLGRIBUCZODISL-UHFFFAOYSA-N 0.000 description 2
- LQDFKWZQZBEFPY-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCC1=CC=C2SC=CC2=C1 LQDFKWZQZBEFPY-UHFFFAOYSA-N 0.000 description 2
- UZOVPAVVQNIHLV-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-benzyl-n-methylethanamine Chemical compound C=1C=C2SC=CC2=CC=1CCOCCN(C)CC1=CC=CC=C1 UZOVPAVVQNIHLV-UHFFFAOYSA-N 0.000 description 2
- FNVOIVCAFYAOCA-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]ethanol Chemical compound OCCOCCC1=CC=C2SC=CC2=C1 FNVOIVCAFYAOCA-UHFFFAOYSA-N 0.000 description 2
- FJDCDFVKRLXOOC-UHFFFAOYSA-N 2-[2-(1-benzothiophen-7-yl)ethoxy]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)COCCC1=CC=CC2=C1SC=C2 FJDCDFVKRLXOOC-UHFFFAOYSA-N 0.000 description 2
- WIYWOLAPTFMVDU-UHFFFAOYSA-N 2-[2-(1-benzothiophen-7-yl)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCC1=CC=CC2=C1SC=C2 WIYWOLAPTFMVDU-UHFFFAOYSA-N 0.000 description 2
- PFAUMRKDUPVGNL-UHFFFAOYSA-N 2-[2-(1-benzothiophen-7-yl)ethoxy]acetic acid Chemical compound OC(=O)COCCC1=CC=CC2=C1SC=C2 PFAUMRKDUPVGNL-UHFFFAOYSA-N 0.000 description 2
- BMKMKOPQFYUNMU-UHFFFAOYSA-N 2-[2-(3,4-diaminophenyl)ethoxy]ethanol Chemical compound NC1=CC=C(CCOCCO)C=C1N BMKMKOPQFYUNMU-UHFFFAOYSA-N 0.000 description 2
- IRUQVCZQBJZCAO-UHFFFAOYSA-N 2-[2-(6-fluoro-1-benzothiophen-5-yl)ethoxy]acetic acid Chemical compound C1=C(F)C(CCOCC(=O)O)=CC2=C1SC=C2 IRUQVCZQBJZCAO-UHFFFAOYSA-N 0.000 description 2
- QUZUMEWVJCHZGM-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-4-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound OCCN(C)CCOCCC1=CC=CC2=C1C=CS2 QUZUMEWVJCHZGM-UHFFFAOYSA-N 0.000 description 2
- ODTFLKMHCGOKDE-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CCOCCC1=CC=C2SC=CC2=C1 ODTFLKMHCGOKDE-UHFFFAOYSA-N 0.000 description 2
- TUTGISTWBPGFMO-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]ethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCN(C)CCOCCC1=CC=C2SC=CC2=C1 TUTGISTWBPGFMO-UHFFFAOYSA-N 0.000 description 2
- BBBXRHNCMVAXFQ-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]ethyl acetate Chemical compound CC(=O)OCCN(C)CCOCCC1=CC=C2SC=CC2=C1 BBBXRHNCMVAXFQ-UHFFFAOYSA-N 0.000 description 2
- ZGNCMBXBNLDLMF-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]propan-1-ol Chemical compound OCC(C)N(C)CCOCCC1=CC=C2SC=CC2=C1 ZGNCMBXBNLDLMF-UHFFFAOYSA-N 0.000 description 2
- YJFGQHCDMAPJFY-UHFFFAOYSA-N 2-[3-[2-(1-benzothiophen-5-yl)ethoxy]propyl-methylamino]ethanol Chemical compound OCCN(C)CCCOCCC1=CC=C2SC=CC2=C1 YJFGQHCDMAPJFY-UHFFFAOYSA-N 0.000 description 2
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 2
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 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 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- SHNHONHOIPJYCP-UHFFFAOYSA-N 5-[2-(1-benzothiophen-5-yl)ethoxy]-n,n-diethylpentan-1-amine Chemical compound CCN(CC)CCCCCOCCC1=CC=C2SC=CC2=C1 SHNHONHOIPJYCP-UHFFFAOYSA-N 0.000 description 2
- XVAHJUJSOJPKMW-UHFFFAOYSA-N 5-[2-[2-(diethylamino)ethoxy]ethyl]-1-benzothiophene-2-carboxylic acid Chemical compound CCN(CC)CCOCCC1=CC=C2SC(C(O)=O)=CC2=C1 XVAHJUJSOJPKMW-UHFFFAOYSA-N 0.000 description 2
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 2
- PUQFLJUNVNKBLN-UHFFFAOYSA-N 6-[2-[2-(dimethylamino)ethoxy]ethyl]chromen-4-one Chemical compound O1C=CC(=O)C2=CC(CCOCCN(C)C)=CC=C21 PUQFLJUNVNKBLN-UHFFFAOYSA-N 0.000 description 2
- UTAWAMOKCMTVID-UHFFFAOYSA-N 6-fluoro-7-methoxy-1-benzothiophene-5-carboxylic acid Chemical compound COC1=C(F)C(C(O)=O)=CC2=C1SC=C2 UTAWAMOKCMTVID-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical group CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 238000000134 MTT assay Methods 0.000 description 2
- 231100000002 MTT assay Toxicity 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- YCXHBZODUOVOMP-UHFFFAOYSA-N [5-[2-[2-(diethylamino)ethoxy]ethyl]-1-benzothiophen-2-yl]boronic acid Chemical compound C(C)N(CCOCCC1=CC2=C(SC(=C2)B(O)O)C=C1)CC YCXHBZODUOVOMP-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000000181 anti-adherent effect Effects 0.000 description 2
- 239000007798 antifreeze agent Substances 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229960005069 calcium Drugs 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 239000012050 conventional carrier Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 235000019700 dicalcium phosphate Nutrition 0.000 description 2
- 229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- VCLNFSRRLSQTDG-UHFFFAOYSA-N ethyl 2-(5,7-difluoro-1-benzothiophen-6-yl)acetate Chemical compound CCOC(=O)CC1=C(F)C=C2C=CSC2=C1F VCLNFSRRLSQTDG-UHFFFAOYSA-N 0.000 description 2
- HVNZXVCPORLSSE-UHFFFAOYSA-N ethyl 4-(2-ethoxy-2-oxoethyl)-2,3,5-trifluorobenzoate Chemical compound CCOC(=O)CC1=C(F)C=C(C(=O)OCC)C(F)=C1F HVNZXVCPORLSSE-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 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 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 229910052622 kaolinite Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- ZLUJWKOWCPXHHL-UHFFFAOYSA-N methyl 4-(2,2-diethoxyethylsulfanyl)-2-fluoro-3-methoxybenzoate Chemical compound CCOC(OCC)CSC1=CC=C(C(=O)OC)C(F)=C1OC ZLUJWKOWCPXHHL-UHFFFAOYSA-N 0.000 description 2
- HHCWEEQNMZDSPO-UHFFFAOYSA-N methyl 6-fluoro-1-benzothiophene-5-carboxylate Chemical compound C1=C(F)C(C(=O)OC)=CC2=C1SC=C2 HHCWEEQNMZDSPO-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- GMYWULGPRXPGMF-UHFFFAOYSA-N n,n-diethyl-2-[2-(6-fluoro-1-benzothiophen-5-yl)ethoxy]ethanamine Chemical compound C1=C(F)C(CCOCCN(CC)CC)=CC2=C1SC=C2 GMYWULGPRXPGMF-UHFFFAOYSA-N 0.000 description 2
- NYPXWGJACZKKMK-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]-n-(1-hydroxypropan-2-yl)formamide Chemical compound OCC(C)N(C=O)CCOCCC1=CC=C2SC=CC2=C1 NYPXWGJACZKKMK-UHFFFAOYSA-N 0.000 description 2
- IQIUEINUJCTTIF-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]-n-benzylprop-2-yn-1-amine Chemical compound C=1C=C2SC=CC2=CC=1CCOCCN(CC#C)CC1=CC=CC=C1 IQIUEINUJCTTIF-UHFFFAOYSA-N 0.000 description 2
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 2
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000000626 neurodegenerative effect Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008137 solubility enhancer Substances 0.000 description 2
- 210000000278 spinal cord Anatomy 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 2
- 210000001519 tissue Anatomy 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
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 230000006269 (delayed) early viral mRNA transcription Effects 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical group C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- MUZIZEZCKKMZRT-UHFFFAOYSA-N 1,2-dithiolane Chemical group C1CSSC1 MUZIZEZCKKMZRT-UHFFFAOYSA-N 0.000 description 1
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical group C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical group C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 1
- 125000000166 1,3-dioxalanyl group Chemical group 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
- CYBYTFKEZYTFLH-UHFFFAOYSA-N 1-(1-benzothiophen-5-yl)propan-2-ol Chemical compound CC(O)CC1=CC=C2SC=CC2=C1 CYBYTFKEZYTFLH-UHFFFAOYSA-N 0.000 description 1
- UCGIMEFPSQVFLY-UHFFFAOYSA-N 1-(1-benzothiophen-5-yl)propan-2-one Chemical compound CC(=O)CC1=CC=C2SC=CC2=C1 UCGIMEFPSQVFLY-UHFFFAOYSA-N 0.000 description 1
- NYLOSPOOCOREQT-UHFFFAOYSA-N 1-(2,2-diethoxyethylsulfanyl)-3-methylbenzene Chemical compound CCOC(OCC)CSC1=CC=CC(C)=C1 NYLOSPOOCOREQT-UHFFFAOYSA-N 0.000 description 1
- KBHSGGYTTRTFRN-UHFFFAOYSA-N 1-[2-(1-benzothiophen-5-yl)ethoxy]-n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)COCCC1=CC=C2SC=CC2=C1 KBHSGGYTTRTFRN-UHFFFAOYSA-N 0.000 description 1
- RWHIBUDYLSNFPQ-UHFFFAOYSA-N 1-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]propan-2-ol;oxalic acid Chemical compound OC(=O)C(O)=O.CC(O)CN(C)CCOCCC1=CC=C2SC=CC2=C1 RWHIBUDYLSNFPQ-UHFFFAOYSA-N 0.000 description 1
- PMUXAPWBDFLFGF-UHFFFAOYSA-N 1-[5-(2-hydroxyethyl)-2-methoxyphenyl]ethanone Chemical compound COC1=CC=C(CCO)C=C1C(C)=O PMUXAPWBDFLFGF-UHFFFAOYSA-N 0.000 description 1
- QJNKBVMFYZBGCI-UHFFFAOYSA-N 1-[5-[2-[2-(diethylamino)ethoxy]ethyl]-2-hydroxyphenyl]ethanone Chemical compound CCN(CC)CCOCCC1=CC=C(O)C(C(C)=O)=C1 QJNKBVMFYZBGCI-UHFFFAOYSA-N 0.000 description 1
- HOPOWIYNQUFRTR-UHFFFAOYSA-N 1-benzothiophene-6-carbaldehyde Chemical compound O=CC1=CC=C2C=CSC2=C1 HOPOWIYNQUFRTR-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical class CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- RRQHLOZQFPWDCA-UHFFFAOYSA-N 1-n,1-n-dimethylpropane-1,2-diamine Chemical compound CC(N)CN(C)C RRQHLOZQFPWDCA-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- SFKRXQKJTIYUAG-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(F)=C1F SFKRXQKJTIYUAG-UHFFFAOYSA-N 0.000 description 1
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 1
- IVXBSWKWQNONLI-UHFFFAOYSA-N 2-(1-benzothiophen-4-yl)acetaldehyde Chemical compound O=CCC1=CC=CC2=C1C=CS2 IVXBSWKWQNONLI-UHFFFAOYSA-N 0.000 description 1
- GQCRCVDVQURUBR-UHFFFAOYSA-N 2-(1-benzothiophen-4-yl)ethanol Chemical compound OCCC1=CC=CC2=C1C=CS2 GQCRCVDVQURUBR-UHFFFAOYSA-N 0.000 description 1
- QLJRRWJMXAZYOH-UHFFFAOYSA-N 2-(2-fluoro-1-benzothiophen-5-yl)ethanol Chemical compound OCCC1=CC=C2SC(F)=CC2=C1 QLJRRWJMXAZYOH-UHFFFAOYSA-N 0.000 description 1
- LMONEXCPVOBHAU-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-5-yl)ethanol Chemical compound OCCC1=CC=C2SC(C)=NC2=C1 LMONEXCPVOBHAU-UHFFFAOYSA-N 0.000 description 1
- HNXSGOGLJYZKHM-UHFFFAOYSA-N 2-(4-chloro-1-benzothiophen-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2SC=CC2=C1Cl HNXSGOGLJYZKHM-UHFFFAOYSA-N 0.000 description 1
- VZAJNCWQXOHYQM-UHFFFAOYSA-N 2-(4-chloro-1-benzothiophen-5-yl)ethanol Chemical compound OCCC1=CC=C2SC=CC2=C1Cl VZAJNCWQXOHYQM-UHFFFAOYSA-N 0.000 description 1
- WBUVEXNUFXSFJI-UHFFFAOYSA-N 2-(4-fluoro-1-benzothiophen-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2SC=CC2=C1F WBUVEXNUFXSFJI-UHFFFAOYSA-N 0.000 description 1
- FDYLJPBFVRLHOP-UHFFFAOYSA-N 2-(4-fluoro-1-benzothiophen-7-yl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C2=C1SC=C2 FDYLJPBFVRLHOP-UHFFFAOYSA-N 0.000 description 1
- KJIQHWSKMGAQLD-UHFFFAOYSA-N 2-(4-fluoro-1-benzothiophen-7-yl)ethanol Chemical compound OCCC1=CC=C(F)C2=C1SC=C2 KJIQHWSKMGAQLD-UHFFFAOYSA-N 0.000 description 1
- OBGXWJYYWCNXIT-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethyl acetate Chemical compound COC1=CC=C(CCOC(C)=O)C=C1 OBGXWJYYWCNXIT-UHFFFAOYSA-N 0.000 description 1
- QWAQEZVXNSMIHM-UHFFFAOYSA-N 2-(5,7-difluoro-1-benzothiophen-6-yl)ethanol Chemical compound OCCC1=C(F)C=C2C=CSC2=C1F QWAQEZVXNSMIHM-UHFFFAOYSA-N 0.000 description 1
- MJHIAPAUUMFIIV-UHFFFAOYSA-N 2-(6-chloro-1-benzothiophen-5-yl)acetic acid Chemical compound C1=C(Cl)C(CC(=O)O)=CC2=C1SC=C2 MJHIAPAUUMFIIV-UHFFFAOYSA-N 0.000 description 1
- KHNYVMIENQYRTF-UHFFFAOYSA-N 2-(6-fluoro-1-benzothiophen-5-yl)acetic acid Chemical compound C1=C(F)C(CC(=O)O)=CC2=C1SC=C2 KHNYVMIENQYRTF-UHFFFAOYSA-N 0.000 description 1
- JQXYXLUDBFLOHF-UHFFFAOYSA-N 2-(6-fluoro-1-benzothiophen-5-yl)ethanol Chemical compound C1=C(F)C(CCO)=CC2=C1SC=C2 JQXYXLUDBFLOHF-UHFFFAOYSA-N 0.000 description 1
- DYZDDAHNZHJBQU-UHFFFAOYSA-N 2-(6-fluoro-1-benzothiophen-7-yl)acetic acid Chemical compound OC(=O)CC1=C(F)C=CC2=C1SC=C2 DYZDDAHNZHJBQU-UHFFFAOYSA-N 0.000 description 1
- GDSNXYVMHPIABL-UHFFFAOYSA-N 2-(6-fluoro-1-benzothiophen-7-yl)ethanol Chemical compound OCCC1=C(F)C=CC2=C1SC=C2 GDSNXYVMHPIABL-UHFFFAOYSA-N 0.000 description 1
- IHNFZFYNBQRPPT-UHFFFAOYSA-N 2-(6-fluoro-7-methoxy-1-benzothiophen-5-yl)ethanol Chemical compound COC1=C(F)C(CCO)=CC2=C1SC=C2 IHNFZFYNBQRPPT-UHFFFAOYSA-N 0.000 description 1
- VBCPXCMPFRRKAO-UHFFFAOYSA-N 2-(6-fluoro-7-methyl-1-benzothiophen-5-yl)acetic acid Chemical compound CC1=C(F)C(CC(O)=O)=CC2=C1SC=C2 VBCPXCMPFRRKAO-UHFFFAOYSA-N 0.000 description 1
- IDEWRDORZDHERL-UHFFFAOYSA-N 2-(6-fluoro-7-methyl-1-benzothiophen-5-yl)ethanol Chemical compound CC1=C(F)C(CCO)=CC2=C1SC=C2 IDEWRDORZDHERL-UHFFFAOYSA-N 0.000 description 1
- VTSRKHKVRNFMPV-UHFFFAOYSA-N 2-(6-fluoro-7-methylsulfanyl-1-benzothiophen-5-yl)acetic acid Chemical compound CSC1=C(F)C(CC(O)=O)=CC2=C1SC=C2 VTSRKHKVRNFMPV-UHFFFAOYSA-N 0.000 description 1
- CYVBWHZTAQLJOX-UHFFFAOYSA-N 2-(6-fluoro-7-methylsulfanyl-1-benzothiophen-5-yl)ethanol Chemical compound CSC1=C(F)C(CCO)=CC2=C1SC=C2 CYVBWHZTAQLJOX-UHFFFAOYSA-N 0.000 description 1
- MHFFTHLDXCBJGU-UHFFFAOYSA-N 2-(6-methoxy-1-benzothiophen-5-yl)acetic acid Chemical compound C1=C(CC(O)=O)C(OC)=CC2=C1C=CS2 MHFFTHLDXCBJGU-UHFFFAOYSA-N 0.000 description 1
- AXVVSCHPBHBZSS-UHFFFAOYSA-N 2-(6-methoxy-1-benzothiophen-5-yl)ethanol Chemical compound C1=C(CCO)C(OC)=CC2=C1C=CS2 AXVVSCHPBHBZSS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 1
- DYYGGKYMLNBFPK-UHFFFAOYSA-N 2-[1-(1-benzothiophen-5-yl)propan-2-yloxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC(C)CC1=CC=C2SC=CC2=C1 DYYGGKYMLNBFPK-UHFFFAOYSA-N 0.000 description 1
- MSSQOQPKGAMUSY-LEAFIULHSA-N 2-[1-[2-[(4r,6s)-8-chloro-6-(2,3-dimethoxyphenyl)-4,6-dihydropyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]piperidin-4-yl]acetic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N3C=CC=C3[C@@H](CC(=O)N3CCC(CC(O)=O)CC3)O2)=C1OC MSSQOQPKGAMUSY-LEAFIULHSA-N 0.000 description 1
- XEPVVMWQYQIJLE-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethoxy]-1-piperidin-1-ylethanone Chemical compound C=1C=C2OCOC2=CC=1CCOCC(=O)N1CCCCC1 XEPVVMWQYQIJLE-UHFFFAOYSA-N 0.000 description 1
- GJPXQEGBBWEJFG-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethoxy]-n,n-dimethylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCOCCC1=CC=C2OCOC2=C1 GJPXQEGBBWEJFG-UHFFFAOYSA-N 0.000 description 1
- PBYDMZAXKLIECB-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethoxy]acetic acid Chemical compound OC(=O)COCCC1=CC=C2OCOC2=C1 PBYDMZAXKLIECB-UHFFFAOYSA-N 0.000 description 1
- RKVXPMPYRRNEOK-UHFFFAOYSA-N 2-[2-(1-benzofuran-5-yl)ethoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOCCC1=CC=C2OC=CC2=C1 RKVXPMPYRRNEOK-UHFFFAOYSA-N 0.000 description 1
- ZAVZXIDTUODQPL-UHFFFAOYSA-N 2-[2-(1-benzofuran-5-yl)ethoxy]-n,n-diethylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.CCN(CC)CCOCCC1=CC=C2OC=CC2=C1 ZAVZXIDTUODQPL-UHFFFAOYSA-N 0.000 description 1
- NJSWGJQTEJUFGJ-UHFFFAOYSA-N 2-[2-(1-benzofuran-5-yl)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCC1=CC=C2OC=CC2=C1 NJSWGJQTEJUFGJ-UHFFFAOYSA-N 0.000 description 1
- HVIQAAIBFAUTEH-UHFFFAOYSA-N 2-[2-(1-benzothiophen-4-yl)ethoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOCCC1=CC=CC2=C1C=CS2 HVIQAAIBFAUTEH-UHFFFAOYSA-N 0.000 description 1
- WWTNBSJYQVFQLO-UHFFFAOYSA-N 2-[2-(1-benzothiophen-4-yl)ethoxy]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)COCCC1=CC=CC2=C1C=CS2 WWTNBSJYQVFQLO-UHFFFAOYSA-N 0.000 description 1
- LFPGQZQVPDZHOV-UHFFFAOYSA-N 2-[2-(1-benzothiophen-4-yl)ethoxy]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.CN(C)CCOCCC1=CC=CC2=C1C=CS2 LFPGQZQVPDZHOV-UHFFFAOYSA-N 0.000 description 1
- XOTUESPUWZZHED-UHFFFAOYSA-N 2-[2-(1-benzothiophen-4-yl)ethoxy]acetic acid Chemical compound OC(=O)COCCC1=CC=CC2=C1C=CS2 XOTUESPUWZZHED-UHFFFAOYSA-N 0.000 description 1
- VUCCWLFUUCADFN-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.CN(C)CCOCCC1=CC=C2SC=CC2=C1 VUCCWLFUUCADFN-UHFFFAOYSA-N 0.000 description 1
- HAYURPJODICEDJ-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-[(4-fluorophenyl)methyl]-n-methylethanamine Chemical compound C=1C=C2SC=CC2=CC=1CCOCCN(C)CC1=CC=C(F)C=C1 HAYURPJODICEDJ-UHFFFAOYSA-N 0.000 description 1
- YHUSHAFCQULDBN-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-[(4-fluorophenyl)methyl]-n-methylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C2SC=CC2=CC=1CCOCCN(C)CC1=CC=C(F)C=C1 YHUSHAFCQULDBN-UHFFFAOYSA-N 0.000 description 1
- BHTWRERHMUEQNH-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-[(4-methoxyphenyl)methyl]-n-methylethanamine Chemical compound C1=CC(OC)=CC=C1CN(C)CCOCCC1=CC=C(SC=C2)C2=C1 BHTWRERHMUEQNH-UHFFFAOYSA-N 0.000 description 1
- PTSCTBFKDGCVJX-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-[(4-methoxyphenyl)methyl]-n-methylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OC)=CC=C1CN(C)CCOCCC1=CC=C(SC=C2)C2=C1 PTSCTBFKDGCVJX-UHFFFAOYSA-N 0.000 description 1
- XCHBWLYWGHOJLP-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-benzyl-n-(2-hydroxyethyl)acetamide Chemical compound C=1C=C2SC=CC2=CC=1CCOCC(=O)N(CCO)CC1=CC=CC=C1 XCHBWLYWGHOJLP-UHFFFAOYSA-N 0.000 description 1
- ZECVWCUMIPNLCN-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-benzyl-n-methylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C2SC=CC2=CC=1CCOCCN(C)CC1=CC=CC=C1 ZECVWCUMIPNLCN-UHFFFAOYSA-N 0.000 description 1
- KOKJLSMXADIGGX-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-ethyl-n-methylethanamine Chemical compound CCN(C)CCOCCC1=CC=C2SC=CC2=C1 KOKJLSMXADIGGX-UHFFFAOYSA-N 0.000 description 1
- GHKWAMNTQYHWRU-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-ethyl-n-methylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.CCN(C)CCOCCC1=CC=C2SC=CC2=C1 GHKWAMNTQYHWRU-UHFFFAOYSA-N 0.000 description 1
- VLDWODKBNIDRIB-UHFFFAOYSA-N 2-[2-(1-benzothiophen-5-yl)ethoxy]-n-methylethanamine Chemical compound CNCCOCCC1=CC=C2SC=CC2=C1 VLDWODKBNIDRIB-UHFFFAOYSA-N 0.000 description 1
- ZZVLIEIGANRBAX-UHFFFAOYSA-N 2-[2-(1-benzothiophen-6-yl)ethoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOCCC1=CC=C2C=CSC2=C1 ZZVLIEIGANRBAX-UHFFFAOYSA-N 0.000 description 1
- FHSSMKQSBHROES-UHFFFAOYSA-N 2-[2-(1-benzothiophen-6-yl)ethoxy]-n,n-diethylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.CCN(CC)CCOCCC1=CC=C2C=CSC2=C1 FHSSMKQSBHROES-UHFFFAOYSA-N 0.000 description 1
- JNABGYUJJOHIHU-UHFFFAOYSA-N 2-[2-(1-benzothiophen-6-yl)ethoxy]acetic acid Chemical compound OC(=O)COCCC1=CC=C2C=CSC2=C1 JNABGYUJJOHIHU-UHFFFAOYSA-N 0.000 description 1
- FUDHFSMHOKZQLP-UHFFFAOYSA-N 2-[2-(1-benzothiophen-7-yl)ethoxy]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.CN(C)CCOCCC1=CC=CC2=C1SC=C2 FUDHFSMHOKZQLP-UHFFFAOYSA-N 0.000 description 1
- CKPDKOUGZUUQDS-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethoxy]-1-piperazin-1-ylethanone Chemical compound C=1C=C2OCCOC2=CC=1CCOCC(=O)N1CCNCC1 CKPDKOUGZUUQDS-UHFFFAOYSA-N 0.000 description 1
- AXZJKGRREFGMBU-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethoxy]-N,N-diethylethanamine hydrochloride Chemical compound Cl.O1CCOC2=CC(CCOCCN(CC)CC)=CC=C21 AXZJKGRREFGMBU-UHFFFAOYSA-N 0.000 description 1
- RFYDWCVVKRWWCJ-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethoxy]-n,n-diethylacetamide Chemical compound O1CCOC2=CC(CCOCC(=O)N(CC)CC)=CC=C21 RFYDWCVVKRWWCJ-UHFFFAOYSA-N 0.000 description 1
- GXRACXIEWNMMAZ-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethoxy]-n,n-diethylethanamine Chemical compound O1CCOC2=CC(CCOCCN(CC)CC)=CC=C21 GXRACXIEWNMMAZ-UHFFFAOYSA-N 0.000 description 1
- DENVBDKAXYSPRI-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethoxy]acetic acid Chemical compound O1CCOC2=CC(CCOCC(=O)O)=CC=C21 DENVBDKAXYSPRI-UHFFFAOYSA-N 0.000 description 1
- TZYSOUFOJMPYEN-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1h-inden-5-yl)ethoxy]-1-piperazin-1-ylethanone Chemical compound C=1C=C2CCCC2=CC=1CCOCC(=O)N1CCNCC1 TZYSOUFOJMPYEN-UHFFFAOYSA-N 0.000 description 1
- IAWLNBSVEXHSPB-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1h-inden-5-yl)ethoxy]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)COCCC1=CC=C2CCCC2=C1 IAWLNBSVEXHSPB-UHFFFAOYSA-N 0.000 description 1
- OCCDIPBKMSQBLI-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1h-inden-5-yl)ethoxy]-n,n-diethylethanamine;hydrochloride Chemical compound Cl.CCN(CC)CCOCCC1=CC=C2CCCC2=C1 OCCDIPBKMSQBLI-UHFFFAOYSA-N 0.000 description 1
- GRXODDJHQJQFGI-UHFFFAOYSA-N 2-[2-(2-methyl-1,3-benzothiazol-5-yl)ethoxy]acetic acid Chemical compound OC(=O)COCCC1=CC=C2SC(C)=NC2=C1 GRXODDJHQJQFGI-UHFFFAOYSA-N 0.000 description 1
- NDNQXLKHSAMXBL-UHFFFAOYSA-N 2-[2-(2-methyl-1-benzothiophen-5-yl)ethoxy]acetic acid Chemical compound OC(=O)COCCC1=CC=C2SC(C)=CC2=C1 NDNQXLKHSAMXBL-UHFFFAOYSA-N 0.000 description 1
- IJFICPWRPPQURG-UHFFFAOYSA-N 2-[2-(2-phenyl-1-benzothiophen-5-yl)ethoxy]-1-piperidin-1-ylethanone Chemical compound C1CCCCN1C(=O)COCCC(C=C1C=2)=CC=C1SC=2C1=CC=CC=C1 IJFICPWRPPQURG-UHFFFAOYSA-N 0.000 description 1
- DVOGSTYSTPATSQ-UHFFFAOYSA-N 2-[2-(2-phenyl-1-benzothiophen-5-yl)ethoxy]acetic acid Chemical compound C=1C2=CC(CCOCC(=O)O)=CC=C2SC=1C1=CC=CC=C1 DVOGSTYSTPATSQ-UHFFFAOYSA-N 0.000 description 1
- CVYYTRKMBYMKKY-UHFFFAOYSA-N 2-[2-(2-phenyl-1-benzothiophen-5-yl)ethoxy]ethanol Chemical compound C=1C2=CC(CCOCCO)=CC=C2SC=1C1=CC=CC=C1 CVYYTRKMBYMKKY-UHFFFAOYSA-N 0.000 description 1
- ANVGEJKBFOQCAR-UHFFFAOYSA-N 2-[2-(2-phenyl-1-benzothiophen-5-yl)ethoxy]ethyl methanesulfonate Chemical compound C=1C2=CC(CCOCCOS(=O)(=O)C)=CC=C2SC=1C1=CC=CC=C1 ANVGEJKBFOQCAR-UHFFFAOYSA-N 0.000 description 1
- FDUOPRMKXLRAPR-UHFFFAOYSA-N 2-[2-(4-chloro-1-benzothiophen-5-yl)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCC1=CC=C2SC=CC2=C1Cl FDUOPRMKXLRAPR-UHFFFAOYSA-N 0.000 description 1
- BRTIGITWNRLWGS-UHFFFAOYSA-N 2-[2-(4-fluoro-1-benzothiophen-5-yl)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCC1=CC=C2SC=CC2=C1F BRTIGITWNRLWGS-UHFFFAOYSA-N 0.000 description 1
- DAQGBIPARKVQJE-UHFFFAOYSA-N 2-[2-(4-fluoro-1-benzothiophen-5-yl)ethoxy]-n,n-dimethylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCOCCC1=CC=C2SC=CC2=C1F DAQGBIPARKVQJE-UHFFFAOYSA-N 0.000 description 1
- ILOIQKBOLZROFA-UHFFFAOYSA-N 2-[2-(4-fluoro-1-benzothiophen-7-yl)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCC1=CC=C(F)C2=C1SC=C2 ILOIQKBOLZROFA-UHFFFAOYSA-N 0.000 description 1
- UDDHRKRLCACEAK-UHFFFAOYSA-N 2-[2-(5,7-difluoro-1-benzothiophen-6-yl)ethoxy]-n,n-diethylethanamine;hydrochloride Chemical compound Cl.CCN(CC)CCOCCC1=C(F)C=C2C=CSC2=C1F UDDHRKRLCACEAK-UHFFFAOYSA-N 0.000 description 1
- GBVKILOIRYJSHB-UHFFFAOYSA-N 2-[2-(6-fluoro-1-benzothiophen-5-yl)ethoxy]-1-piperidin-1-ylethanone Chemical compound FC1=CC=2SC=CC=2C=C1CCOCC(=O)N1CCCCC1 GBVKILOIRYJSHB-UHFFFAOYSA-N 0.000 description 1
- UDRBUNUYTVDZGK-UHFFFAOYSA-N 2-[2-(6-fluoro-1-benzothiophen-7-yl)ethoxy]-n-(2-hydroxyethyl)-n-methylacetamide Chemical compound OCCN(C)C(=O)COCCC1=C(F)C=CC2=C1SC=C2 UDRBUNUYTVDZGK-UHFFFAOYSA-N 0.000 description 1
- OGYMIYNDXZQWEG-UHFFFAOYSA-N 2-[2-(6-methoxy-1-benzothiophen-5-yl)ethoxy]-1-piperazin-1-ylethanone Chemical compound COC1=C(CCOCC(=O)N2CCNCC2)C=C2C=CSC2=C1 OGYMIYNDXZQWEG-UHFFFAOYSA-N 0.000 description 1
- WZCDDEAELNVAEO-UHFFFAOYSA-N 2-[2-(6-methoxy-1-benzothiophen-5-yl)ethoxy]acetic acid Chemical compound C1=C(CCOCC(O)=O)C(OC)=CC2=C1C=CS2 WZCDDEAELNVAEO-UHFFFAOYSA-N 0.000 description 1
- YNNUSGIPVFPVBX-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC(C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-UHFFFAOYSA-N 0.000 description 1
- WSFWIDYAIIZBKT-UHFFFAOYSA-N 2-[2-[2-(1-benzofuran-5-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound OCCN(C)CCOCCC1=CC=C2OC=CC2=C1 WSFWIDYAIIZBKT-UHFFFAOYSA-N 0.000 description 1
- JKMMAZFNPDTBIW-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-benzylamino]ethanol Chemical compound C=1C=C2SC=CC2=CC=1CCOCCN(CCO)CC1=CC=CC=C1 JKMMAZFNPDTBIW-UHFFFAOYSA-N 0.000 description 1
- SDYSHBXDQIGOQJ-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-benzylamino]ethanol;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C2SC=CC2=CC=1CCOCCN(CCO)CC1=CC=CC=C1 SDYSHBXDQIGOQJ-UHFFFAOYSA-N 0.000 description 1
- SZTZCXJBJLYFCL-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-ethylamino]ethanol Chemical compound OCCN(CC)CCOCCC1=CC=C2SC=CC2=C1 SZTZCXJBJLYFCL-UHFFFAOYSA-N 0.000 description 1
- BQEAYBXALCRIFX-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-ethylamino]ethanol;oxalic acid Chemical compound OC(=O)C(O)=O.OCCN(CC)CCOCCC1=CC=C2SC=CC2=C1 BQEAYBXALCRIFX-UHFFFAOYSA-N 0.000 description 1
- YRTHOUOOWVVGDL-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]ethanol;oxalic acid Chemical compound OC(=O)C(O)=O.OCCN(C)CCOCCC1=CC=C2SC=CC2=C1 YRTHOUOOWVVGDL-UHFFFAOYSA-N 0.000 description 1
- UWJNRCOKEUNYMZ-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]propan-1-ol;oxalic acid Chemical compound OC(=O)C(O)=O.OCC(C)N(C)CCOCCC1=CC=C2SC=CC2=C1 UWJNRCOKEUNYMZ-UHFFFAOYSA-N 0.000 description 1
- NARGAGILTLAOKM-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethylamino]propan-1-ol Chemical compound OCC(C)NCCOCCC1=CC=C2SC=CC2=C1 NARGAGILTLAOKM-UHFFFAOYSA-N 0.000 description 1
- MIJXWNMESVPLKE-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-6-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound OCCN(C)CCOCCC1=CC=C2C=CSC2=C1 MIJXWNMESVPLKE-UHFFFAOYSA-N 0.000 description 1
- JSFDCMIAWILFKB-UHFFFAOYSA-N 2-[2-[2-(1-benzothiophen-7-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound OCCN(C)CCOCCC1=CC=CC2=C1SC=C2 JSFDCMIAWILFKB-UHFFFAOYSA-N 0.000 description 1
- LXHKOTWXDWBXRM-UHFFFAOYSA-N 2-[2-[2-(5,7-difluoro-1-benzothiophen-6-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound OCCN(C)CCOCCC1=C(F)C=C2C=CSC2=C1F LXHKOTWXDWBXRM-UHFFFAOYSA-N 0.000 description 1
- AFQYETVFZLLFED-UHFFFAOYSA-N 2-[2-[2-(5-methoxy-1-benzofuran-6-yl)ethoxy]ethyl-methylamino]ethanol;hydrochloride Chemical compound Cl.C1=C(CCOCCN(C)CCO)C(OC)=CC2=C1OC=C2 AFQYETVFZLLFED-UHFFFAOYSA-N 0.000 description 1
- CQLWFEGOPQYWJS-UHFFFAOYSA-N 2-[2-[2-(6-fluoro-1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]ethanol;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(F)C(CCOCCN(CCO)C)=CC2=C1SC=C2 CQLWFEGOPQYWJS-UHFFFAOYSA-N 0.000 description 1
- YDEGHLUYASXOGM-UHFFFAOYSA-N 2-[2-[2-(6-fluoro-7-methoxy-1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]ethanol Chemical compound COC1=C(F)C(CCOCCN(C)CCO)=CC2=C1SC=C2 YDEGHLUYASXOGM-UHFFFAOYSA-N 0.000 description 1
- MOLPFXVMEUMWPY-UHFFFAOYSA-N 2-[3-(1-benzothiophen-5-yl)propoxy]acetic acid Chemical compound OC(=O)COCCCC1=CC=C2SC=CC2=C1 MOLPFXVMEUMWPY-UHFFFAOYSA-N 0.000 description 1
- VPWWYSSVWLNAMZ-UHFFFAOYSA-N 2-[3-[2-(1-benzothiophen-5-yl)ethoxy]propyl-methylamino]ethanol;oxalic acid Chemical compound OC(=O)C(O)=O.OCCN(C)CCCOCCC1=CC=C2SC=CC2=C1 VPWWYSSVWLNAMZ-UHFFFAOYSA-N 0.000 description 1
- XDDFCIMENWOUCD-UHFFFAOYSA-N 2-[5-(1-benzothiophen-5-yl)pentyl-methylamino]ethanol Chemical compound OCCN(C)CCCCCC1=CC=C2SC=CC2=C1 XDDFCIMENWOUCD-UHFFFAOYSA-N 0.000 description 1
- YZPUFJQXPMXRFG-UHFFFAOYSA-N 2-[5-(1-benzothiophen-5-yl)pentyl-methylamino]ethanol;oxalic acid Chemical compound OC(=O)C(O)=O.OCCN(C)CCCCCC1=CC=C2SC=CC2=C1 YZPUFJQXPMXRFG-UHFFFAOYSA-N 0.000 description 1
- WMGHXROLUCFYJX-UHFFFAOYSA-N 2-[5-[2-(1-benzothiophen-5-yl)ethoxy]pentyl-methylamino]ethanol Chemical compound OCCN(C)CCCCCOCCC1=CC=C2SC=CC2=C1 WMGHXROLUCFYJX-UHFFFAOYSA-N 0.000 description 1
- VQKKVQWTOUDRFE-UHFFFAOYSA-N 2-[5-[2-(1-benzothiophen-5-yl)ethoxy]pentyl-methylamino]ethanol;oxalic acid Chemical compound OC(=O)C(O)=O.OCCN(C)CCCCCOCCC1=CC=C2SC=CC2=C1 VQKKVQWTOUDRFE-UHFFFAOYSA-N 0.000 description 1
- BSAPOXZSZNPOMR-UHFFFAOYSA-N 2-[methyl-[2-(2-naphthalen-1-ylethoxy)ethyl]amino]ethanol Chemical compound C1=CC=C2C(CCOCCN(CCO)C)=CC=CC2=C1 BSAPOXZSZNPOMR-UHFFFAOYSA-N 0.000 description 1
- SAAWVHOUDJRBCN-UHFFFAOYSA-N 2-[methyl-[2-[2-(2-methyl-1,3-benzothiazol-5-yl)ethoxy]ethyl]amino]ethanol Chemical compound OCCN(C)CCOCCC1=CC=C2SC(C)=NC2=C1 SAAWVHOUDJRBCN-UHFFFAOYSA-N 0.000 description 1
- YRWNTURPCOCHKD-UHFFFAOYSA-N 2-[methyl-[2-[2-(2-methyl-1-benzothiophen-5-yl)ethoxy]ethyl]amino]ethanol;oxalic acid Chemical compound OC(=O)C(O)=O.OCCN(C)CCOCCC1=CC=C2SC(C)=CC2=C1 YRWNTURPCOCHKD-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- RXWNCMHRJCOWDK-UHFFFAOYSA-N 2-naphthalen-1-ylethanol Chemical compound C1=CC=C2C(CCO)=CC=CC2=C1 RXWNCMHRJCOWDK-UHFFFAOYSA-N 0.000 description 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-M 2-oxobutanoate Chemical compound CCC(=O)C([O-])=O TYEYBOSBBBHJIV-UHFFFAOYSA-M 0.000 description 1
- 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 1
- SLXRRBLVHWIRJH-UHFFFAOYSA-N 3-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]propan-1-ol Chemical compound OCCCN(C)CCOCCC1=CC=C2SC=CC2=C1 SLXRRBLVHWIRJH-UHFFFAOYSA-N 0.000 description 1
- BSAAEUCBNNLPND-UHFFFAOYSA-N 3-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl-methylamino]propan-1-ol;oxalic acid Chemical compound OC(=O)C(O)=O.OCCCN(C)CCOCCC1=CC=C2SC=CC2=C1 BSAAEUCBNNLPND-UHFFFAOYSA-N 0.000 description 1
- HNFMVVHMKGFCMB-UHFFFAOYSA-N 3-[3-[4-(1-aminocyclobutyl)phenyl]-5-phenylimidazo[4,5-b]pyridin-2-yl]pyridin-2-amine Chemical compound NC1=NC=CC=C1C1=NC2=CC=C(C=3C=CC=CC=3)N=C2N1C1=CC=C(C2(N)CCC2)C=C1 HNFMVVHMKGFCMB-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
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
- OCOBFMZGRJOSOU-UHFFFAOYSA-N 3-o-tert-butyl 1-o-ethyl propanedioate Chemical compound CCOC(=O)CC(=O)OC(C)(C)C OCOBFMZGRJOSOU-UHFFFAOYSA-N 0.000 description 1
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- MMNUGEVICOPLAW-UHFFFAOYSA-N 4-chloro-1-benzothiophene-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC=CC2=C1Cl MMNUGEVICOPLAW-UHFFFAOYSA-N 0.000 description 1
- PNHACIGGFQCRCB-UHFFFAOYSA-N 4-fluoro-1-benzothiophene-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC=CC2=C1F PNHACIGGFQCRCB-UHFFFAOYSA-N 0.000 description 1
- SOPRMFWHAPJXKL-UHFFFAOYSA-N 4-fluoro-1-benzothiophene-7-carboxylic acid Chemical compound OC(=O)C1=CC=C(F)C2=C1SC=C2 SOPRMFWHAPJXKL-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- QHNUYBXBPYFESF-UHFFFAOYSA-N 5-(1-benzothiophen-5-yl)-n,n-diethylpentan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.CCN(CC)CCCCCC1=CC=C2SC=CC2=C1 QHNUYBXBPYFESF-UHFFFAOYSA-N 0.000 description 1
- KGWHJJGMLYFIDK-UHFFFAOYSA-N 5-[2-(1-benzothiophen-5-yl)ethoxy]-n,n-diethylpentan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CCCCCOCCC1=CC=C2SC=CC2=C1 KGWHJJGMLYFIDK-UHFFFAOYSA-N 0.000 description 1
- GYNUJGSVGYBGQA-UHFFFAOYSA-N 5-[2-(5-chloropentoxy)ethyl]-1-benzothiophene Chemical compound ClCCCCCOCCC1=CC=C2SC=CC2=C1 GYNUJGSVGYBGQA-UHFFFAOYSA-N 0.000 description 1
- PUKRNGLOAQXGKW-UHFFFAOYSA-N 5-[2-[2-(diethylamino)ethoxy]ethyl]-1-benzothiophene-2-carboxamide Chemical compound CCN(CC)CCOCCC1=CC=C2SC(C(N)=O)=CC2=C1 PUKRNGLOAQXGKW-UHFFFAOYSA-N 0.000 description 1
- RHSXKYOBLFOWFW-UHFFFAOYSA-N 5-[2-[2-(diethylamino)ethoxy]ethyl]-1-benzothiophene-2-carboxylic acid;hydrochloride Chemical compound Cl.CCN(CC)CCOCCC1=CC=C2SC(C(O)=O)=CC2=C1 RHSXKYOBLFOWFW-UHFFFAOYSA-N 0.000 description 1
- XMLQMYCSMZBNAD-UHFFFAOYSA-N 6-[2-(2-chloroethoxy)ethyl]quinoxaline;hydrochloride Chemical compound Cl.N1=CC=NC2=CC(CCOCCCl)=CC=C21 XMLQMYCSMZBNAD-UHFFFAOYSA-N 0.000 description 1
- QPWORIRNXXNOMD-UHFFFAOYSA-N 6-[2-[2-(diethylamino)ethoxy]ethyl]chromen-4-one Chemical compound O1C=CC(=O)C2=CC(CCOCCN(CC)CC)=CC=C21 QPWORIRNXXNOMD-UHFFFAOYSA-N 0.000 description 1
- WZXXDRVZDMDPQP-UHFFFAOYSA-N 6-[2-[2-(diethylamino)ethoxy]ethyl]chromen-4-one;hydrochloride Chemical compound Cl.O1C=CC(=O)C2=CC(CCOCCN(CC)CC)=CC=C21 WZXXDRVZDMDPQP-UHFFFAOYSA-N 0.000 description 1
- OUWIZTMUPNEDND-UHFFFAOYSA-N 6-chloro-1-benzothiophene-5-carboxylic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC2=C1SC=C2 OUWIZTMUPNEDND-UHFFFAOYSA-N 0.000 description 1
- JVDWOZRFTYLMBP-UHFFFAOYSA-N 6-fluoro-1-benzothiophene-5-carboxylic acid Chemical compound C1=C(F)C(C(=O)O)=CC2=C1SC=C2 JVDWOZRFTYLMBP-UHFFFAOYSA-N 0.000 description 1
- ZWSREUHMESJJFY-UHFFFAOYSA-N 6-fluoro-1-benzothiophene-7-carboxylic acid Chemical compound OC(=O)C1=C(F)C=CC2=C1SC=C2 ZWSREUHMESJJFY-UHFFFAOYSA-N 0.000 description 1
- DEDJVLHYOMVPQJ-UHFFFAOYSA-N 6-fluoro-5-[2-[2-[2-hydroxyethyl(methyl)amino]ethoxy]ethyl]-1-benzothiophen-7-ol Chemical compound OC1=C(F)C(CCOCCN(CCO)C)=CC2=C1SC=C2 DEDJVLHYOMVPQJ-UHFFFAOYSA-N 0.000 description 1
- UVGPPFPJAQSQJA-UHFFFAOYSA-N 6-fluoro-7-methyl-1-benzothiophene-5-carboxylic acid Chemical compound CC1=C(F)C(C(O)=O)=CC2=C1SC=C2 UVGPPFPJAQSQJA-UHFFFAOYSA-N 0.000 description 1
- YGEGQTPCLUUYDQ-UHFFFAOYSA-N 6-fluoro-7-methylsulfanyl-1-benzothiophene-5-carboxylic acid Chemical compound CSC1=C(F)C(C(O)=O)=CC2=C1SC=C2 YGEGQTPCLUUYDQ-UHFFFAOYSA-N 0.000 description 1
- JAVYCOVKZHFDID-UHFFFAOYSA-N 6-methoxy-1-benzothiophene-5-carboxylic acid Chemical compound C1=C(C(O)=O)C(OC)=CC2=C1C=CS2 JAVYCOVKZHFDID-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000037259 Amyloid Plaque Diseases 0.000 description 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- NMNKKDHSOFUYBE-UHFFFAOYSA-N COc1cc(cc2cc(F)sc12)C(O)=O Chemical compound COc1cc(cc2cc(F)sc12)C(O)=O NMNKKDHSOFUYBE-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 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
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical class COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical group C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- FHDUPBGLSPKGEY-UHFFFAOYSA-N S1C=CC(=C1)C(C=C)OC(C=1C=CSC1)C=C Chemical compound S1C=CC(=C1)C(C=C)OC(C=1C=CSC1)C=C FHDUPBGLSPKGEY-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 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
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical group C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- PXFMNBBYUKYHML-UHFFFAOYSA-N [Na].C(C)(C)(C)OC(CC(=O)OC(C)(C)C)=O Chemical compound [Na].C(C)(C)(C)OC(CC(=O)OC(C)(C)C)=O PXFMNBBYUKYHML-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940023476 agar Drugs 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000001980 alanyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- HZVVJJIYJKGMFL-UHFFFAOYSA-N almasilate Chemical compound O.[Mg+2].[Al+3].[Al+3].O[Si](O)=O.O[Si](O)=O HZVVJJIYJKGMFL-UHFFFAOYSA-N 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
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000002862 amidating effect Effects 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-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
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004227 calcium gluconate Substances 0.000 description 1
- 235000013927 calcium gluconate Nutrition 0.000 description 1
- 229960004494 calcium gluconate Drugs 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 208000013677 cerebrovascular dementia Diseases 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- FLGZHHJNRZUPIL-UHFFFAOYSA-N chromene-4-thione Chemical class C1=CC=C2C(=S)C=COC2=C1 FLGZHHJNRZUPIL-UHFFFAOYSA-N 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940125876 compound 15a Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000003635 deoxygenating effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000005332 diethylamines Chemical class 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 1
- 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000006437 ethyl cyclopropyl group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical group C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000002075 main ingredient Substances 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
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- SUOVHDGBKPOZBF-UHFFFAOYSA-N methyl 2,4-difluoro-3-methoxybenzoate Chemical compound COC(=O)C1=CC=C(F)C(OC)=C1F SUOVHDGBKPOZBF-UHFFFAOYSA-N 0.000 description 1
- NQBWNCJNCKDXDE-UHFFFAOYSA-N methyl 2-(2,2-diethoxyethylsulfanyl)-4-fluorobenzoate Chemical compound CCOC(OCC)CSC1=CC(F)=CC=C1C(=O)OC NQBWNCJNCKDXDE-UHFFFAOYSA-N 0.000 description 1
- AYKWIVDARGXSMT-UHFFFAOYSA-N methyl 2-(2,2-diethoxyethylsulfanyl)-6-fluorobenzoate Chemical compound CCOC(OCC)CSC1=CC=CC(F)=C1C(=O)OC AYKWIVDARGXSMT-UHFFFAOYSA-N 0.000 description 1
- BNFXUUAGIHRNBC-UHFFFAOYSA-N methyl 2-(6-fluoro-7-methoxy-1-benzothiophen-5-yl)acetate Chemical compound COC1=C(F)C(CC(=O)OC)=CC2=C1SC=C2 BNFXUUAGIHRNBC-UHFFFAOYSA-N 0.000 description 1
- VUAHRBHEHSBYHD-UHFFFAOYSA-N methyl 4-(2,2-diethoxyethylsulfanyl)-2-fluoro-3-methylbenzoate Chemical compound CCOC(OCC)CSC1=CC=C(C(=O)OC)C(F)=C1C VUAHRBHEHSBYHD-UHFFFAOYSA-N 0.000 description 1
- CXEYXKIMUKELDM-UHFFFAOYSA-N methyl 4-(2,2-diethoxyethylsulfanyl)-2-fluorobenzoate Chemical compound CCOC(OCC)CSC1=CC=C(C(=O)OC)C(F)=C1 CXEYXKIMUKELDM-UHFFFAOYSA-N 0.000 description 1
- ZDNXYHXKMGTECY-UHFFFAOYSA-N methyl 4-chloro-1-benzothiophene-5-carboxylate Chemical compound COC(=O)C1=CC=C2SC=CC2=C1Cl ZDNXYHXKMGTECY-UHFFFAOYSA-N 0.000 description 1
- HPSXXBUIMSUNGM-UHFFFAOYSA-N methyl 4-fluoro-1-benzothiophene-5-carboxylate Chemical compound COC(=O)C1=CC=C2SC=CC2=C1F HPSXXBUIMSUNGM-UHFFFAOYSA-N 0.000 description 1
- GIGPHQFRZHWBND-UHFFFAOYSA-N methyl 4-fluoro-1-benzothiophene-7-carboxylate Chemical compound COC(=O)C1=CC=C(F)C2=C1SC=C2 GIGPHQFRZHWBND-UHFFFAOYSA-N 0.000 description 1
- DCFKBOAFODDZKL-UHFFFAOYSA-N methyl 6-chloro-1-benzothiophene-5-carboxylate Chemical compound C1=C(Cl)C(C(=O)OC)=CC2=C1SC=C2 DCFKBOAFODDZKL-UHFFFAOYSA-N 0.000 description 1
- HQLDWQRBOUYLOS-UHFFFAOYSA-N methyl 6-fluoro-7-methoxy-1-benzothiophene-5-carboxylate Chemical compound COC1=C(F)C(C(=O)OC)=CC2=C1SC=C2 HQLDWQRBOUYLOS-UHFFFAOYSA-N 0.000 description 1
- AHVIUZDXYRNTCY-UHFFFAOYSA-N methyl 6-fluoro-7-methyl-1-benzothiophene-5-carboxylate Chemical compound CC1=C(F)C(C(=O)OC)=CC2=C1SC=C2 AHVIUZDXYRNTCY-UHFFFAOYSA-N 0.000 description 1
- SSRJDJFYBJOOON-UHFFFAOYSA-N methyl 6-methoxy-1-benzothiophene-5-carboxylate Chemical compound C1=C(OC)C(C(=O)OC)=CC2=C1SC=C2 SSRJDJFYBJOOON-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000002406 microsurgery Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000001087 myotubule Anatomy 0.000 description 1
- DMHPLPRGMTXUAV-UHFFFAOYSA-N n,n-diethyl-2-(2-naphthalen-1-ylethoxy)ethanamine Chemical compound C1=CC=C2C(CCOCCN(CC)CC)=CC=CC2=C1 DMHPLPRGMTXUAV-UHFFFAOYSA-N 0.000 description 1
- LWMXNDOZEAGCFC-UHFFFAOYSA-N n,n-diethyl-2-(2-naphthalen-1-ylethoxy)ethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC=C2C(CCOCCN(CC)CC)=CC=CC2=C1 LWMXNDOZEAGCFC-UHFFFAOYSA-N 0.000 description 1
- QKXXNRQLFGLDSB-UHFFFAOYSA-N n,n-diethyl-2-(2-naphthalen-2-ylethoxy)ethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC=CC2=CC(CCOCCN(CC)CC)=CC=C21 QKXXNRQLFGLDSB-UHFFFAOYSA-N 0.000 description 1
- KQTOCGLGEGEJKF-UHFFFAOYSA-N n,n-diethyl-2-[2-(6-fluoro-1-benzothiophen-5-yl)ethoxy]acetamide Chemical compound C1=C(F)C(CCOCC(=O)N(CC)CC)=CC2=C1SC=C2 KQTOCGLGEGEJKF-UHFFFAOYSA-N 0.000 description 1
- KUNHCGYGRWZRGO-UHFFFAOYSA-N n,n-dimethyl-2-(2-naphthalen-1-ylethoxy)ethanamine Chemical compound C1=CC=C2C(CCOCCN(C)C)=CC=CC2=C1 KUNHCGYGRWZRGO-UHFFFAOYSA-N 0.000 description 1
- UNRVLHQKEGKBAZ-UHFFFAOYSA-N n,n-dimethyl-2-(2-naphthalen-1-ylethoxy)ethanamine;hydrochloride Chemical compound Cl.C1=CC=C2C(CCOCCN(C)C)=CC=CC2=C1 UNRVLHQKEGKBAZ-UHFFFAOYSA-N 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- HGEKDLQMMHESNL-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]-2-methoxy-n-methylethanamine Chemical compound COCCN(C)CCOCCC1=CC=C2SC=CC2=C1 HGEKDLQMMHESNL-UHFFFAOYSA-N 0.000 description 1
- GJRIMXZBCMVUTE-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]-n-benzylcyclopropanamine Chemical compound C=1C=C2SC=CC2=CC=1CCOCCN(C1CC1)CC1=CC=CC=C1 GJRIMXZBCMVUTE-UHFFFAOYSA-N 0.000 description 1
- WYCOQUSVIJJHLP-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]-n-benzylprop-2-yn-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C2SC=CC2=CC=1CCOCCN(CC#C)CC1=CC=CC=C1 WYCOQUSVIJJHLP-UHFFFAOYSA-N 0.000 description 1
- FXUABPKQFPSFLF-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]-n-methylcyclopropanamine;hydrochloride Chemical compound Cl.C=1C=C2SC=CC2=CC=1CCOCCN(C)C1CC1 FXUABPKQFPSFLF-UHFFFAOYSA-N 0.000 description 1
- TYJWRKBPZLSOJR-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCOCCC1=CC=C2SC=CC2=C1 TYJWRKBPZLSOJR-UHFFFAOYSA-N 0.000 description 1
- HPGARIDBQVLLBR-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]-n-propan-2-ylpropan-2-amine;hydrochloride Chemical compound Cl.CC(C)N(C(C)C)CCOCCC1=CC=C2SC=CC2=C1 HPGARIDBQVLLBR-UHFFFAOYSA-N 0.000 description 1
- VTYQJRVQDYKCKH-UHFFFAOYSA-N n-[2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl]prop-2-yn-1-amine Chemical compound C#CCNCCOCCC1=CC=C2SC=CC2=C1 VTYQJRVQDYKCKH-UHFFFAOYSA-N 0.000 description 1
- LIOWKXYXSUMWNO-UHFFFAOYSA-N n-benzyl-2-[2-(6-fluoro-1-benzothiophen-5-yl)ethoxy]-n-methylethanamine Chemical compound C=1C=2C=CSC=2C=C(F)C=1CCOCCN(C)CC1=CC=CC=C1 LIOWKXYXSUMWNO-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
- 230000007830 nerve conduction Effects 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 230000000508 neurotrophic effect Effects 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- IVMHDOBGNQOUHO-UHFFFAOYSA-N oxathiane Chemical group C1CCSOC1 IVMHDOBGNQOUHO-UHFFFAOYSA-N 0.000 description 1
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical group C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 208000027232 peripheral nervous system disease Diseases 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- CGIRHIYXKARDEI-UHFFFAOYSA-M sodium;hydrogen carbonate;oxaldehyde Chemical compound [Na+].OC([O-])=O.O=CC=O CGIRHIYXKARDEI-UHFFFAOYSA-M 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- KUYMVWXKHQSIAS-UHFFFAOYSA-N tert-butyl 2-chloroacetate Chemical compound CC(C)(C)OC(=O)CCl KUYMVWXKHQSIAS-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical group C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
- C07C217/10—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16587999 | 1999-06-11 | ||
PCT/JP2000/003748 WO2000076957A1 (fr) | 1999-06-11 | 2000-06-09 | Derives de n-alkoxyalkyl, n-dialkylamine ou leurs sels et remedes contre les maladies a degenerescence nerveuse, qui les contiennent |
Publications (2)
Publication Number | Publication Date |
---|---|
SK17812001A3 SK17812001A3 (sk) | 2002-11-06 |
SK287673B6 true SK287673B6 (sk) | 2011-05-06 |
Family
ID=15820725
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1781-2001A SK287673B6 (sk) | 1999-06-11 | 2000-06-09 | Derivát N-alkoxyalkyl-N,N-dialkylamínu, liečivo obsahujúce tento derivát a jeho použitie |
Country Status (24)
Country | Link |
---|---|
US (1) | US6797726B1 (el) |
EP (1) | EP1186594B1 (el) |
JP (1) | JP4782961B2 (el) |
KR (1) | KR100641352B1 (el) |
CN (1) | CN1155558C (el) |
AT (1) | ATE438614T1 (el) |
AU (1) | AU770234B2 (el) |
BR (1) | BR0011505A (el) |
CA (1) | CA2374659C (el) |
CY (1) | CY1109334T1 (el) |
CZ (1) | CZ302083B6 (el) |
DE (1) | DE60042686D1 (el) |
DK (1) | DK1186594T3 (el) |
ES (1) | ES2329003T3 (el) |
HU (1) | HU229250B1 (el) |
MX (1) | MXPA01012627A (el) |
NO (1) | NO322473B1 (el) |
NZ (1) | NZ515706A (el) |
PL (1) | PL196773B1 (el) |
PT (1) | PT1186594E (el) |
RO (1) | RO122361B1 (el) |
SK (1) | SK287673B6 (el) |
WO (1) | WO2000076957A1 (el) |
ZA (1) | ZA200109699B (el) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100956990B1 (ko) | 2001-10-19 | 2010-05-11 | 토야마 케미칼 컴퍼니 리미티드 | 알킬에테르유도체 또는 그 염 |
ES2379948T3 (es) * | 2002-06-14 | 2012-05-07 | Toyama Chemical Co., Ltd. | Composición medicinal que comprende Tacrine o Donepezil para mejorar la función cerebral |
EP1707203A1 (en) * | 2005-04-01 | 2006-10-04 | Bioprojet | Treatment of parkinson's disease obstructive sleep apnea, dementia with lewy bodies, vascular dementia with non-imidazole alkylamines histamine H3- receptor ligands |
JP4902247B2 (ja) * | 2005-04-08 | 2012-03-21 | 富山化学工業株式会社 | 2−(1−ベンゾチオフェン−5−イル)エタノールの新規製造法およびその中間体 |
JP2006328058A (ja) * | 2005-04-27 | 2006-12-07 | Toyama Chem Co Ltd | 2−(1−ベンゾチオフェン−5−イル)エタノールの新規製造法およびその中間体 |
US8119625B2 (en) * | 2006-04-26 | 2012-02-21 | Toyama Chemical Co., Ltd. | Neurogenesis inducer or neuropathy therapeutic agent comprising alkyl ether derivative or salt thereof |
PL2011796T3 (pl) * | 2006-04-26 | 2015-03-31 | Toyama Chemical Co Ltd | Induktor neurogenezy lub środek terapeutyczny do stosowania w neuropatii zawierający pochodną eteru alkilowego lub jej sól |
FR2933977B1 (fr) * | 2008-07-18 | 2013-04-26 | Centre Nat Rech Scient | Derives heterocycliques utiles dans le traitement des maladies neurodegeneratives |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2820817A (en) * | 1954-02-04 | 1958-01-21 | Mcneilab Inc | Oxygenated indan compounds and method of making the same |
US5280032A (en) | 1989-02-14 | 1994-01-18 | Toyama Chemical Co., Ltd. | 1,2-ethanediol derivative and salt thereof, process for producing the same, and cerebral function-improving agent comprising the same |
JP2887492B2 (ja) * | 1990-02-05 | 1999-04-26 | 富山化学工業株式会社 | 1,2―エタンジオール誘導体およびその塩 |
JP3044055B2 (ja) * | 1990-08-09 | 2000-05-22 | 富山化学工業株式会社 | 1,2―エタンジオール誘導体およびその塩 |
JP2873898B2 (ja) * | 1992-04-13 | 1999-03-24 | 富山化学工業株式会社 | ベンゾ[b]チオフェン−5−イル誘導体もしくはその光学活性体またはそれらの塩並びにそれらの製造法 |
WO1995019336A1 (de) * | 1994-01-12 | 1995-07-20 | Iovis Biomedical And Pharmaceutical Consultants | Phenylethanolaminether und ihre verwendung als beta-adrenorezeptor-agonisten |
EP0790246B1 (en) * | 1994-10-25 | 2002-01-16 | Toyama Chemical Co., Ltd. | Potentiator for nerve growth factor activity containing 1,2-ethanediol derivative or salt thereof |
WO1999031056A1 (fr) | 1997-12-12 | 1999-06-24 | Toyama Chemical Co., Ltd. | Derives d'ether alcoylique ou leurs sels, et antagonistes du calcium les contenant |
-
2000
- 2000-06-09 US US09/926,739 patent/US6797726B1/en not_active Expired - Fee Related
- 2000-06-09 SK SK1781-2001A patent/SK287673B6/sk not_active IP Right Cessation
- 2000-06-09 KR KR1020017015388A patent/KR100641352B1/ko not_active IP Right Cessation
- 2000-06-09 MX MXPA01012627A patent/MXPA01012627A/es active IP Right Grant
- 2000-06-09 WO PCT/JP2000/003748 patent/WO2000076957A1/ja active IP Right Grant
- 2000-06-09 JP JP2001503817A patent/JP4782961B2/ja not_active Expired - Fee Related
- 2000-06-09 NZ NZ515706A patent/NZ515706A/en not_active IP Right Cessation
- 2000-06-09 CZ CZ20014331A patent/CZ302083B6/cs not_active IP Right Cessation
- 2000-06-09 AT AT00935600T patent/ATE438614T1/de active
- 2000-06-09 PT PT00935600T patent/PT1186594E/pt unknown
- 2000-06-09 DK DK00935600T patent/DK1186594T3/da active
- 2000-06-09 CN CNB008095337A patent/CN1155558C/zh not_active Expired - Fee Related
- 2000-06-09 EP EP00935600A patent/EP1186594B1/en not_active Expired - Lifetime
- 2000-06-09 ES ES00935600T patent/ES2329003T3/es not_active Expired - Lifetime
- 2000-06-09 RO ROA200101327A patent/RO122361B1/ro unknown
- 2000-06-09 AU AU51072/00A patent/AU770234B2/en not_active Ceased
- 2000-06-09 DE DE60042686T patent/DE60042686D1/de not_active Expired - Lifetime
- 2000-06-09 HU HU0204177A patent/HU229250B1/hu not_active IP Right Cessation
- 2000-06-09 BR BR0011505-3A patent/BR0011505A/pt not_active IP Right Cessation
- 2000-06-09 PL PL352172A patent/PL196773B1/pl not_active IP Right Cessation
- 2000-06-09 CA CA2374659A patent/CA2374659C/en not_active Expired - Fee Related
-
2001
- 2001-11-26 ZA ZA200109699A patent/ZA200109699B/en unknown
- 2001-12-10 NO NO20016029A patent/NO322473B1/no not_active IP Right Cessation
-
2009
- 2009-09-01 CY CY20091100909T patent/CY1109334T1/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7468443B2 (en) | Alkyl ether derivatives or salts thereof | |
CA2452596C (en) | Benzo-fused 5-membered heterocyclic compounds, their production and use | |
US9409864B2 (en) | Sulfonamide TRPA1 receptor antagonists | |
JP4642657B2 (ja) | アルキルエーテル誘導体またはその塩を含有する網膜神経疾患の予防・治療剤 | |
SK287673B6 (sk) | Derivát N-alkoxyalkyl-N,N-dialkylamínu, liečivo obsahujúce tento derivát a jeho použitie | |
DE69828522T2 (de) | Antithrombotische mittel | |
WO1999031056A1 (fr) | Derives d'ether alcoylique ou leurs sels, et antagonistes du calcium les contenant | |
JP4549452B2 (ja) | アルキルエーテル誘導体またはその塩並びにそれらを含有するカルシウム拮抗剤 | |
JP4061059B2 (ja) | N−アルコキシアルキル−n−アルキルアミン誘導体またはその塩 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20140609 |