SK152003A3 - Amino alcohol derivatives - Google Patents

Info

Publication number

SK152003A3

SK152003A3 SK15-2003A SK152003A SK152003A3 SK 152003 A3 SK152003 A3 SK 152003A3 SK 152003 A SK152003 A SK 152003A SK 152003 A3 SK152003 A3 SK 152003A3

Authority

SK

Slovakia

Prior art keywords

group

amino

methyl

butan

thiophen

Prior art date

2000-07-13

Links

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• 150000001414 amino alcohols Chemical class 0.000 title description 20
• 150000001875 compounds Chemical class 0.000 claims abstract description 546
• 125000001424 substituent group Chemical group 0.000 claims abstract description 211
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 159
• 125000003118 aryl group Chemical group 0.000 claims abstract description 121
• 150000003839 salts Chemical class 0.000 claims abstract description 114
• 150000002148 esters Chemical class 0.000 claims abstract description 77
• 125000006239 protecting group Chemical group 0.000 claims abstract description 75
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 61
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 48
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 33
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 16
• 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims abstract 2
• -1 lower aliphatic acyl Chemical group 0.000 claims description 833
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 150
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 125
• 238000000034 method Methods 0.000 claims description 104
• 125000001072 heteroaryl group Chemical group 0.000 claims description 64
• 125000005842 heteroatom Chemical group 0.000 claims description 50
• 125000002252 acyl group Chemical group 0.000 claims description 49
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 45
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 40
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 37
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 36
• 125000003342 alkenyl group Chemical group 0.000 claims description 35
• 125000002947 alkylene group Chemical group 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 125000001931 aliphatic group Chemical group 0.000 claims description 32
• 125000000304 alkynyl group Chemical group 0.000 claims description 32
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 28
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000004434 sulfur atom Chemical group 0.000 claims description 26
• 229910052717 sulfur Inorganic materials 0.000 claims description 24
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 229910052757 nitrogen Chemical group 0.000 claims description 20
• 239000000460 chlorine Substances 0.000 claims description 16
• 125000004414 alkyl thio group Chemical group 0.000 claims description 14
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 13
• 238000002360 preparation method Methods 0.000 claims description 13
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 11
• 239000004367 Lipase Substances 0.000 claims description 11
• 102000004882 Lipase Human genes 0.000 claims description 11
• 108090001060 Lipase Proteins 0.000 claims description 11
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 11
• 235000019421 lipase Nutrition 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 125000001544 thienyl group Chemical group 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 9
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 7
• 208000023275 Autoimmune disease Diseases 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• LIMIHFSKFNHQQB-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(4-phenylbut-1-ynyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCC1=CC=CC=C1 LIMIHFSKFNHQQB-UHFFFAOYSA-N 0.000 claims description 5
• ZXTOCDYUMTYUNT-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCCC1=CC=CC=C1 ZXTOCDYUMTYUNT-UHFFFAOYSA-N 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000003107 substituted aryl group Chemical group 0.000 claims description 5
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• GYKMIALFFVLIRO-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]-4-phenylbutan-1-one Chemical compound S1C(CCC(N)(CO)C)=CC=C1C(=O)CCCC1=CC=CC=C1 GYKMIALFFVLIRO-UHFFFAOYSA-N 0.000 claims description 4
• QMLPAHQTMVVDHX-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]-5-cyclohexylpentan-1-one Chemical compound S1C(CCC(N)(CO)C)=CC=C1C(=O)CCCCC1CCCCC1 QMLPAHQTMVVDHX-UHFFFAOYSA-N 0.000 claims description 4
• CSLGJAYXLICWSW-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(5-phenylpentyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCCC1=CC=CC=C1 CSLGJAYXLICWSW-UHFFFAOYSA-N 0.000 claims description 4
• JVNQBPRBODGDAP-UHFFFAOYSA-N 2-amino-4-[5-(4-cyclohexyloxybutyl)thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCOC1CCCCC1 JVNQBPRBODGDAP-UHFFFAOYSA-N 0.000 claims description 4
• KMBDVNHQFIJUJC-UHFFFAOYSA-N 2-amino-4-[5-(5-cyclohexylpent-1-ynyl)thiophen-2-yl]-2-ethylbutan-1-ol Chemical compound S1C(CCC(N)(CO)CC)=CC=C1C#CCCCC1CCCCC1 KMBDVNHQFIJUJC-UHFFFAOYSA-N 0.000 claims description 4
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• WNAWFEHEWUBREF-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]-5-(4-fluorophenyl)pentan-1-one Chemical compound S1C(CCC(N)(CO)C)=CC=C1C(=O)CCCCC1=CC=C(F)C=C1 WNAWFEHEWUBREF-UHFFFAOYSA-N 0.000 claims description 3
• DIJCONIVOSXNMB-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-[3-(4-methylphenoxy)prop-1-ynyl]thiophen-2-yl]butan-1-ol Chemical compound C1=CC(C)=CC=C1OCC#CC1=CC=C(CCC(C)(N)CO)S1 DIJCONIVOSXNMB-UHFFFAOYSA-N 0.000 claims description 3
• HKFXJZXPFXEBDO-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-[4-(4-methylphenoxy)but-1-ynyl]thiophen-2-yl]butan-1-ol Chemical compound C1=CC(C)=CC=C1OCCC#CC1=CC=C(CCC(C)(N)CO)S1 HKFXJZXPFXEBDO-UHFFFAOYSA-N 0.000 claims description 3
• WREKFUNQAUVBSS-UHFFFAOYSA-N 2-amino-4-[5-(4-cyclohexylbutyl)thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCC1CCCCC1 WREKFUNQAUVBSS-UHFFFAOYSA-N 0.000 claims description 3
• YHDMCBRQISJINB-UHFFFAOYSA-N 2-amino-4-[5-(5-cyclohexylpentyl)thiophen-2-yl]-2-ethylbutan-1-ol Chemical compound S1C(CCC(N)(CO)CC)=CC=C1CCCCCC1CCCCC1 YHDMCBRQISJINB-UHFFFAOYSA-N 0.000 claims description 3
• LLYXBXSWALVOQC-UHFFFAOYSA-N 2-amino-4-[5-(5-cyclohexylpentyl)thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCCC1CCCCC1 LLYXBXSWALVOQC-UHFFFAOYSA-N 0.000 claims description 3
• JSDPFMBYHXOWTK-UHFFFAOYSA-N 2-amino-4-[5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound C1=C(C)C(C)=CC=C1OCC#CC1=CC=C(CCC(C)(N)CO)S1 JSDPFMBYHXOWTK-UHFFFAOYSA-N 0.000 claims description 3
• LEEQAJSIPLPWFR-UHFFFAOYSA-N 2-amino-4-[5-[3-(3-methoxyphenoxy)prop-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound COC1=CC=CC(OCC#CC=2SC(CCC(C)(N)CO)=CC=2)=C1 LEEQAJSIPLPWFR-UHFFFAOYSA-N 0.000 claims description 3
• KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical class OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 3
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
• 238000005917 acylation reaction Methods 0.000 claims description 3
• 230000001900 immune effect Effects 0.000 claims description 3
• 210000000056 organ Anatomy 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 238000002054 transplantation Methods 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• HVIACRVLKODYQT-UHFFFAOYSA-N 1-[3-[3-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]prop-2-ynoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(OCC#CC=2SC(CCC(C)(N)CO)=CC=2)=C1 HVIACRVLKODYQT-UHFFFAOYSA-N 0.000 claims description 2
• FNDYWWVNJZVAEF-UHFFFAOYSA-N 1-[4-[3-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]prop-2-ynoxy]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC#CC1=CC=C(CCC(C)(N)CO)S1 FNDYWWVNJZVAEF-UHFFFAOYSA-N 0.000 claims description 2
• YMOPUVBVLIXCKO-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]-3-(cyclohexylmethoxy)propan-1-one Chemical compound S1C(CCC(N)(CO)C)=CC=C1C(=O)CCOCC1CCCCC1 YMOPUVBVLIXCKO-UHFFFAOYSA-N 0.000 claims description 2
• QTRYPOAGXTZWOK-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]-4-phenoxybutan-1-one Chemical compound S1C(CCC(N)(CO)C)=CC=C1C(=O)CCCOC1=CC=CC=C1 QTRYPOAGXTZWOK-UHFFFAOYSA-N 0.000 claims description 2
• ZDOSOJSDNYYZFF-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]-6-phenylhexan-1-one Chemical compound S1C(CCC(N)(CO)C)=CC=C1C(=O)CCCCCC1=CC=CC=C1 ZDOSOJSDNYYZFF-UHFFFAOYSA-N 0.000 claims description 2
• UPAZMFXJVLLGIV-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(3-phenoxypropyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCOC1=CC=CC=C1 UPAZMFXJVLLGIV-UHFFFAOYSA-N 0.000 claims description 2
• IRJDGAOPUVIUDO-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(4-phenoxybut-1-ynyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCOC1=CC=CC=C1 IRJDGAOPUVIUDO-UHFFFAOYSA-N 0.000 claims description 2
• KLRKYMKYWSSTCZ-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(4-phenoxybutyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCOC1=CC=CC=C1 KLRKYMKYWSSTCZ-UHFFFAOYSA-N 0.000 claims description 2
• KXVWHVSCXAHXAI-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(4-phenylmethoxyphenyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 KXVWHVSCXAHXAI-UHFFFAOYSA-N 0.000 claims description 2
• VDLOUQCAPAECDT-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(5-phenoxypentyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCCOC1=CC=CC=C1 VDLOUQCAPAECDT-UHFFFAOYSA-N 0.000 claims description 2
• PYFGFFAHTBAPAR-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(6-phenylhex-1-ynyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCCCC1=CC=CC=C1 PYFGFFAHTBAPAR-UHFFFAOYSA-N 0.000 claims description 2
• WIFBDGDEOBDMHM-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(6-phenylhexyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCCCC1=CC=CC=C1 WIFBDGDEOBDMHM-UHFFFAOYSA-N 0.000 claims description 2
• MWUGTOCPOQYOSR-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-[3-(3-methylphenoxy)prop-1-ynyl]thiophen-2-yl]butan-1-ol Chemical compound CC1=CC=CC(OCC#CC=2SC(CCC(C)(N)CO)=CC=2)=C1 MWUGTOCPOQYOSR-UHFFFAOYSA-N 0.000 claims description 2
• QZGYGXKVEHBXTN-UHFFFAOYSA-N 2-amino-4-[5-[3-(3,4-dimethoxyphenoxy)prop-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound C1=C(OC)C(OC)=CC=C1OCC#CC1=CC=C(CCC(C)(N)CO)S1 QZGYGXKVEHBXTN-UHFFFAOYSA-N 0.000 claims description 2
• SDGNEXUDZUIXTN-UHFFFAOYSA-N 2-amino-4-[5-[3-(3,5-dimethoxyphenoxy)prop-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound COC1=CC(OC)=CC(OCC#CC=2SC(CCC(C)(N)CO)=CC=2)=C1 SDGNEXUDZUIXTN-UHFFFAOYSA-N 0.000 claims description 2
• VPVTZUQJABPICQ-UHFFFAOYSA-N 2-amino-4-[5-[3-(4-chlorophenoxy)prop-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCOC1=CC=C(Cl)C=C1 VPVTZUQJABPICQ-UHFFFAOYSA-N 0.000 claims description 2
• ZXVYZDMOINFQJE-UHFFFAOYSA-N 2-amino-4-[5-[3-(4-ethylphenoxy)prop-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound C1=CC(CC)=CC=C1OCC#CC1=CC=C(CCC(C)(N)CO)S1 ZXVYZDMOINFQJE-UHFFFAOYSA-N 0.000 claims description 2
• BVHPTCDRKHOCER-UHFFFAOYSA-N 2-amino-4-[5-[3-(cyclohexylmethoxy)propyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCOCC1CCCCC1 BVHPTCDRKHOCER-UHFFFAOYSA-N 0.000 claims description 2
• YQPXWZMNBYNMFA-UHFFFAOYSA-N 2-amino-4-[5-[4-(4-fluorophenoxy)but-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCOC1=CC=C(F)C=C1 YQPXWZMNBYNMFA-UHFFFAOYSA-N 0.000 claims description 2
• DTEFVXTVPKZINI-UHFFFAOYSA-N 2-amino-4-[5-[4-(4-fluorophenoxy)butyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCOC1=CC=C(F)C=C1 DTEFVXTVPKZINI-UHFFFAOYSA-N 0.000 claims description 2
• ZWYNWEPVACMNOC-UHFFFAOYSA-N 2-amino-4-[5-[5-(4-fluorophenyl)pent-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCCC1=CC=C(F)C=C1 ZWYNWEPVACMNOC-UHFFFAOYSA-N 0.000 claims description 2
• ZFHVDCFRLOGRFX-UHFFFAOYSA-N 2-amino-4-[5-[5-(4-methoxyphenyl)pent-1-ynyl]thiophen-2-yl]-2-methylbutan-1-ol Chemical compound C1=CC(OC)=CC=C1CCCC#CC1=CC=C(CCC(C)(N)CO)S1 ZFHVDCFRLOGRFX-UHFFFAOYSA-N 0.000 claims description 2
• MZWUOVQGTFLRMG-UHFFFAOYSA-N NC(CO)(CCC=1SC(=CC1)C#CCSC1=CC=C(C=C1)C)C Chemical compound NC(CO)(CCC=1SC(=CC1)C#CCSC1=CC=C(C=C1)C)C MZWUOVQGTFLRMG-UHFFFAOYSA-N 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
• XRIKESJANHLVBM-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)thiophen-2-yl]-5-phenylpentan-1-one Chemical compound S1C(CCC(N)(CO)C)=CC=C1C(=O)CCCCC1=CC=CC=C1 XRIKESJANHLVBM-UHFFFAOYSA-N 0.000 claims 2
• UCUNDGLTBBZWPD-UHFFFAOYSA-N 2-amino-4-[5-(4-cyclohexylbut-1-ynyl)thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCC1CCCCC1 UCUNDGLTBBZWPD-UHFFFAOYSA-N 0.000 claims 2
• JENRQCNQHRCINU-UHFFFAOYSA-N 2-amino-4-[5-(5-cyclohexylpent-1-ynyl)thiophen-2-yl]-2-methylbutan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCCC1CCCCC1 JENRQCNQHRCINU-UHFFFAOYSA-N 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000006373 (C2-C10) alkyl group Chemical group 0.000 claims 1
• ZNDXRFUUHGYDIM-UHFFFAOYSA-N 1-[5-[3-amino-3-(hydroxymethyl)pentyl]thiophen-2-yl]-5-cyclohexylpentan-1-one Chemical compound S1C(CCC(N)(CO)CC)=CC=C1C(=O)CCCCC1CCCCC1 ZNDXRFUUHGYDIM-UHFFFAOYSA-N 0.000 claims 1
• IGLJVTRDUXSMOH-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(4-phenylbutyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCC1=CC=CC=C1 IGLJVTRDUXSMOH-UHFFFAOYSA-N 0.000 claims 1
• PCNLZJSPZMWDBH-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(4-phenylmethoxybut-1-ynyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1C#CCCOCC1=CC=CC=C1 PCNLZJSPZMWDBH-UHFFFAOYSA-N 0.000 claims 1
• ZULGLEOCOQGEEM-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(4-phenylmethoxybutyl)thiophen-2-yl]butan-1-ol Chemical compound S1C(CCC(N)(CO)C)=CC=C1CCCCOCC1=CC=CC=C1 ZULGLEOCOQGEEM-UHFFFAOYSA-N 0.000 claims 1
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