NO325780B1 - Alkyleter-derivater eller deres salter, fremgangsmater for fremstilling av slike samt farmasoytiske preparater inneholdende slike - Google Patents

Info

Publication number

NO325780B1

NO325780B1 NO20041531A NO20041531A NO325780B1 NO 325780 B1 NO325780 B1 NO 325780B1 NO 20041531 A NO20041531 A NO 20041531A NO 20041531 A NO20041531 A NO 20041531A NO 325780 B1 NO325780 B1 NO 325780B1

Authority

NO

Norway

Prior art keywords

group

ethoxy

benzothiophen

general formula

ring

Prior art date

2001-10-19

Links

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• 150000003839 salts Chemical class 0.000 title claims abstract description 51
• 150000005215 alkyl ethers Chemical class 0.000 title claims abstract description 20
• 238000002360 preparation method Methods 0.000 title claims description 150
• 238000000034 method Methods 0.000 title claims description 56
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
• 230000008569 process Effects 0.000 title claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 37
• 125000003277 amino group Chemical group 0.000 claims abstract description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
• 210000000578 peripheral nerve Anatomy 0.000 claims abstract description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 159
• 238000006243 chemical reaction Methods 0.000 claims description 77
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 37
• HQNACSFBDBYLJP-UHFFFAOYSA-N 1-[3-[2-(1-benzothiophen-5-yl)ethoxy]propyl]azetidin-3-ol Chemical compound C1C(O)CN1CCCOCCC1=CC=C(SC=C2)C2=C1 HQNACSFBDBYLJP-UHFFFAOYSA-N 0.000 claims description 13
• 150000002170 ethers Chemical class 0.000 claims description 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
• 238000006722 reduction reaction Methods 0.000 claims description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 150000001298 alcohols Chemical class 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 31
• 210000005036 nerve Anatomy 0.000 abstract description 10
• 210000002569 neuron Anatomy 0.000 abstract description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 8
• 230000008929 regeneration Effects 0.000 abstract description 8
• 238000011069 regeneration method Methods 0.000 abstract description 8
• 125000000217 alkyl group Chemical group 0.000 abstract description 7
• 125000000623 heterocyclic group Chemical group 0.000 abstract description 7
• 201000010099 disease Diseases 0.000 abstract description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
• 239000003814 drug Substances 0.000 abstract description 6
• 229940124597 therapeutic agent Drugs 0.000 abstract description 6
• 125000003342 alkenyl group Chemical group 0.000 abstract description 4
• 125000003302 alkenyloxy group Chemical group 0.000 abstract description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 abstract description 4
• 125000005843 halogen group Chemical group 0.000 abstract description 4
• 125000003118 aryl group Chemical group 0.000 abstract description 3
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 3
• 125000004414 alkyl thio group Chemical group 0.000 abstract description 2
• 125000003710 aryl alkyl group Chemical group 0.000 abstract description 2
• 125000004104 aryloxy group Chemical group 0.000 abstract description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
• 210000002241 neurite Anatomy 0.000 abstract 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
• 125000004043 oxo group Chemical group O=* 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 327
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 186
• 239000000243 solution Substances 0.000 description 178
• -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy Chemical group 0.000 description 152
• 239000012044 organic layer Substances 0.000 description 128
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 124
• 239000000203 mixture Substances 0.000 description 117
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 112
• 239000002904 solvent Substances 0.000 description 105
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 102
• 235000002639 sodium chloride Nutrition 0.000 description 94
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 93
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 82
• 239000013078 crystal Substances 0.000 description 80
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
• 239000011541 reaction mixture Substances 0.000 description 72
• 230000002829 reductive effect Effects 0.000 description 71
• 229920006395 saturated elastomer Polymers 0.000 description 66
• 239000003921 oil Substances 0.000 description 63
• 235000019198 oils Nutrition 0.000 description 63
• 239000011780 sodium chloride Substances 0.000 description 62
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 60
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 59
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
• 238000004440 column chromatography Methods 0.000 description 38
• 239000003480 eluent Substances 0.000 description 37
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
• 239000002585 base Substances 0.000 description 27
• 239000012230 colorless oil Substances 0.000 description 27
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• 238000001914 filtration Methods 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 22
• 238000001816 cooling Methods 0.000 description 21
• 239000000543 intermediate Substances 0.000 description 21
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 20
• 239000003795 chemical substances by application Substances 0.000 description 20
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 238000012360 testing method Methods 0.000 description 18
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
• 125000006239 protecting group Chemical group 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• 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 14
• 239000000126 substance Substances 0.000 description 13
• LDBJRAPVWMOXRF-UHFFFAOYSA-N 1-(3-chloropropyl)-3-trityloxyazetidine Chemical compound C1N(CCCCl)CC1OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LDBJRAPVWMOXRF-UHFFFAOYSA-N 0.000 description 12
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• 150000001408 amides Chemical class 0.000 description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
• 238000003756 stirring Methods 0.000 description 11
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• GEZDICNOLPTCMD-UHFFFAOYSA-N 3-[2-(1-benzothiophen-5-yl)ethoxy]-1-(3-hydroxyazetidin-1-yl)propan-1-one Chemical compound C1C(O)CN1C(=O)CCOCCC1=CC=C(SC=C2)C2=C1 GEZDICNOLPTCMD-UHFFFAOYSA-N 0.000 description 9
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
• 101100020289 Xenopus laevis koza gene Proteins 0.000 description 9
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
• 150000008282 halocarbons Chemical class 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 238000004519 manufacturing process Methods 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• 235000017557 sodium bicarbonate Nutrition 0.000 description 9
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
• 239000008096 xylene Substances 0.000 description 9
• RLUCYBFCLXANSO-BTJKTKAUSA-N 1-[3-[2-(1-benzothiophen-5-yl)ethoxy]propyl]azetidin-3-ol;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1C(O)CN1CCCOCCC1=CC=C(SC=C2)C2=C1 RLUCYBFCLXANSO-BTJKTKAUSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 238000004090 dissolution Methods 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 150000002825 nitriles Chemical class 0.000 description 8
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
• UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical class [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 7
• 239000003638 chemical reducing agent Substances 0.000 description 7
• MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 7
• 150000004820 halides Chemical class 0.000 description 7
• 239000012279 sodium borohydride Substances 0.000 description 7
• 229910000033 sodium borohydride Inorganic materials 0.000 description 7
• 150000003462 sulfoxides Chemical class 0.000 description 7
• WTWKLIODKHMITQ-UHFFFAOYSA-N 1-[3-[2-(1-benzothiophen-5-yl)ethoxy]propyl]-3-trityloxyazetidine Chemical compound C=1C=C2SC=CC2=CC=1CCOCCCN(C1)CC1OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WTWKLIODKHMITQ-UHFFFAOYSA-N 0.000 description 6
• QIEKEKLCCHNJCK-UHFFFAOYSA-N 3-[2-(1-benzothiophen-5-yl)ethoxy]propanoic acid Chemical compound OC(=O)CCOCCC1=CC=C2SC=CC2=C1 QIEKEKLCCHNJCK-UHFFFAOYSA-N 0.000 description 6
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
• 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 6
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• 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 6
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 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
• 238000007796 conventional method Methods 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• 239000008103 glucose Substances 0.000 description 6
• 229960001031 glucose Drugs 0.000 description 6
• 239000003112 inhibitor Substances 0.000 description 6
• 150000007529 inorganic bases Chemical class 0.000 description 6
• 239000002198 insoluble material Substances 0.000 description 6
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
• 239000011976 maleic acid Substances 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
• 230000009467 reduction Effects 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
• 239000003826 tablet Substances 0.000 description 6
• 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 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
• CDAINZKOPSNUIN-UHFFFAOYSA-N 3-[2-(1-benzothiophen-5-yl)ethoxy]propan-1-ol Chemical compound OCCCOCCC1=CC=C2SC=CC2=C1 CDAINZKOPSNUIN-UHFFFAOYSA-N 0.000 description 5
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
• 206010012289 Dementia Diseases 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 235000011054 acetic acid Nutrition 0.000 description 5
• 150000008065 acid anhydrides Chemical class 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
• 239000002609 medium Substances 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 150000007530 organic bases Chemical class 0.000 description 5
• 235000006408 oxalic acid Nutrition 0.000 description 5
• 229910052760 oxygen Inorganic materials 0.000 description 5
• 239000001301 oxygen Chemical group 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• RMSPWVGIOSSPPJ-UHFFFAOYSA-N 1-[3-[2-(1-benzothiophen-5-yl)ethoxy]propyl]pyrrolidin-3-amine Chemical compound C1C(N)CCN1CCCOCCC1=CC=C(SC=C2)C2=C1 RMSPWVGIOSSPPJ-UHFFFAOYSA-N 0.000 description 4
• DSZAQLDIEKUEMB-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)ethanol Chemical compound OCCC1=CC=C2SC=CC2=C1 DSZAQLDIEKUEMB-UHFFFAOYSA-N 0.000 description 4
• WWWFRCCPUURAQP-UHFFFAOYSA-N 3-[2-(1-benzothiophen-5-yl)ethoxy]propyl methanesulfonate Chemical compound CS(=O)(=O)OCCCOCCC1=CC=C2SC=CC2=C1 WWWFRCCPUURAQP-UHFFFAOYSA-N 0.000 description 4
• HAQZMAOKHXGOHX-UHFFFAOYSA-N 3-trityloxyazetidine;hydrochloride Chemical compound Cl.C1NCC1OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HAQZMAOKHXGOHX-UHFFFAOYSA-N 0.000 description 4
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
• 239000002841 Lewis acid Substances 0.000 description 4
• 108010025020 Nerve Growth Factor Proteins 0.000 description 4
• 102000015336 Nerve Growth Factor Human genes 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
• 241000700159 Rattus Species 0.000 description 4
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-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
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
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• ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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• JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-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
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