SK152003A3 - Amino alcohol derivatives - Google Patents
Amino alcohol derivatives Download PDFInfo
- 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
Links
- 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
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- 229940095064 tartrate Drugs 0.000 description 1
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- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- RKIDPTUGNXTOMU-UHFFFAOYSA-N thionyl iodide Chemical compound IS(I)=O RKIDPTUGNXTOMU-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 229930195735 unsaturated hydrocarbon Chemical group 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/002—Nitriles (-CN)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/008—Preparation of nitrogen-containing organic compounds containing a N-O bond, e.g. nitro (-NO2), nitroso (-NO)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000212246 | 2000-07-13 | ||
JP2000241744 | 2000-08-09 | ||
JP2000283218 | 2000-09-19 | ||
PCT/JP2001/005988 WO2002006268A1 (fr) | 2000-07-13 | 2001-07-10 | Derives d'alcool amino |
Publications (1)
Publication Number | Publication Date |
---|---|
SK152003A3 true SK152003A3 (en) | 2004-07-07 |
Family
ID=27344040
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK15-2003A SK152003A3 (en) | 2000-07-13 | 2001-07-10 | Amino alcohol derivatives |
Country Status (20)
Country | Link |
---|---|
US (2) | US6723745B2 (hu) |
EP (1) | EP1300405B1 (hu) |
KR (1) | KR100812578B1 (hu) |
CN (2) | CN1328387C (hu) |
AT (1) | ATE360011T1 (hu) |
AU (2) | AU6950301A (hu) |
BR (1) | BR0112484A (hu) |
CA (1) | CA2415678A1 (hu) |
CZ (1) | CZ200350A3 (hu) |
DE (1) | DE60127961D1 (hu) |
HK (1) | HK1051680A1 (hu) |
HU (1) | HUP0301688A3 (hu) |
IL (3) | IL153594A0 (hu) |
MX (1) | MXPA03000397A (hu) |
NO (1) | NO20030120L (hu) |
NZ (2) | NZ523554A (hu) |
PL (1) | PL359411A1 (hu) |
SK (1) | SK152003A3 (hu) |
TW (1) | TWI301833B (hu) |
WO (1) | WO2002006268A1 (hu) |
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US7169818B2 (en) | 2000-10-03 | 2007-01-30 | University Of Virginia Patent Foundation | Lysophosphatidic acid receptor agonists and antagonists |
CA2437358A1 (en) | 2001-01-30 | 2002-08-22 | University Of Virginia Patent Foundation | Agonists and antagonists of sphingosine-1-phosphate receptors |
US7326801B2 (en) * | 2001-03-26 | 2008-02-05 | Novartis Ag | 2-amino-propanol derivatives |
KR100836547B1 (ko) * | 2002-01-11 | 2008-06-10 | 상꾜 가부시키가이샤 | 아미노 알코올 유도체 또는 포스폰산 유도체 및 이들을함유하는 의약 조성물 |
EP1478641A1 (en) * | 2002-01-24 | 2004-11-24 | Eli Lilly And Company | Process for preparing an intermediate useful for the asymmetric synthesis of duloxetine |
ES2316758T3 (es) | 2002-05-16 | 2009-04-16 | Novartis Ag | Uso de aglutinantes del receptor edg en el cancer. |
SE0202279D0 (sv) * | 2002-07-19 | 2002-07-19 | Astrazeneca Ab | Novel comppounds |
SE0202280D0 (sv) * | 2002-07-19 | 2002-07-19 | Astrazeneca Ab | Novel compounds |
MXPA05003080A (es) | 2002-09-19 | 2005-06-15 | Kyorin Seiyaku Kk | Derivado de amino alcohol, sales de los mismos y agentes inmunosupresores. |
CN1708293A (zh) * | 2002-09-24 | 2005-12-14 | 诺瓦提斯公司 | 治疗脱髓鞘疾病的鞘氨醇-1-磷酸受体激动剂 |
US7452911B2 (en) | 2002-10-31 | 2008-11-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
CN1780594A (zh) | 2002-11-07 | 2006-05-31 | 康复米斯公司 | 用于确定半月板的大小和形状以及设计治疗的方法 |
HUE028247T2 (hu) | 2003-04-08 | 2016-12-28 | Novartis Ag | S1P receptoragonistát és cukoralkoholt tartalmazó szilárd, orális adagolású készítmény |
WO2005005383A1 (ja) * | 2003-07-11 | 2005-01-20 | Sankyo Company, Limited | アミノアルコール化合物 |
TW200505416A (en) * | 2003-08-12 | 2005-02-16 | Mitsubishi Pharma Corp | Bi-aryl compound having immunosuppressive activity |
GB0320638D0 (en) | 2003-09-03 | 2003-10-01 | Novartis Ag | Organic compounds |
GB0329498D0 (en) | 2003-12-19 | 2004-01-28 | Novartis Ag | Organic compounds |
DE102004004719A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von enantiomerenreinen Aminoalkoholen |
RU2332212C2 (ru) * | 2004-02-24 | 2008-08-27 | Санкио Компани, Лимитед | Аминоспирт |
TW200602337A (en) | 2004-02-25 | 2006-01-16 | Wyeth Corp | Inhibitors of protein tyrosine phosphatase 1B |
WO2005105146A1 (en) * | 2004-05-03 | 2005-11-10 | Novartis Ag | Combinations comprising a s1p receptor agonist and a jak3 kinase inhibitor |
WO2005115150A2 (en) | 2004-05-06 | 2005-12-08 | University Of Virginia Patent Foundation | Novel lysophosphatidic acid receptor selective antagonists |
CA2571710A1 (en) | 2004-06-24 | 2006-11-02 | Nicholas Valiante | Small molecule immunopotentiators and assays for their detection |
ATE502630T1 (de) | 2004-07-16 | 2011-04-15 | Kyorin Seiyaku Kk | Verfahren zur effektiven anwendung eines medikaments und verfahren zur prävention von nebenwirkungen |
TW200611687A (en) * | 2004-07-29 | 2006-04-16 | Sankyo Co | Pharmaceutical compositions used for immunosuppressant |
PT1773307E (pt) | 2004-07-30 | 2015-01-14 | Novartis Ag | Formulações de compostos à base de 2-amino-1,3- propanodiol |
US7119211B2 (en) * | 2004-09-23 | 2006-10-10 | Yamakawa Chemical Industry Co., Ltd. | Process for preparing optically active 3-(methylamino)-1-(2-thienyl) propan-1-ol and intermediates for preparation |
EP2511262B1 (en) * | 2004-10-12 | 2017-02-01 | Kyorin Pharmaceutical Co., Ltd. | Process for producing 2-amino-2-[2-[4-(3-benzyloxy-phenylthio)-2-chlorophenyl[ethyl]-1,3-propanediol hydrochloride |
MX2007006373A (es) | 2004-11-29 | 2007-06-20 | Novartis Ag | Regimen de dosificacion de un agonista del receptor s1p. |
GB0504544D0 (en) | 2005-03-04 | 2005-04-13 | Novartis Ag | Organic compounds |
GB0519274D0 (en) * | 2005-09-21 | 2005-11-02 | Arakis Ltd | The treatment of neurodegenerative diseases |
WO2007043433A1 (ja) * | 2005-10-07 | 2007-04-19 | Kyorin Pharmaceutical Co., Ltd. | 2-アミノ-1,3-プロパンジオール誘導体を有効成分とする肝臓疾患治療剤および肝臓疾患治療方法 |
TWI389683B (zh) * | 2006-02-06 | 2013-03-21 | Kyorin Seiyaku Kk | A therapeutic agent for an inflammatory bowel disease or an inflammatory bowel disease treatment using a 2-amino-1,3-propanediol derivative as an active ingredient |
BRPI0710878A2 (pt) | 2006-04-11 | 2015-03-31 | Novartis Ag | Compostos orgânicos e seus usos |
GB0612721D0 (en) | 2006-06-27 | 2006-08-09 | Novartis Ag | Organic compounds |
TW200815600A (en) | 2006-08-04 | 2008-04-01 | Daiichi Sankyo Co Ltd | An enzyme for phosphorizing a medicine |
MY146775A (en) * | 2006-08-08 | 2012-09-28 | Kyorin Seiyaku Kk | Amino alcohol derivative and immunosuppressive agent having same as an active ingredient |
RU2430925C2 (ru) * | 2006-08-08 | 2011-10-10 | Киорин Фармасьютикал Ко., Лтд. | Производное аминофосфата и модулятор рецептора s1p, содержащий его в качестве активного ингредиента |
EP2086514A2 (en) | 2006-09-26 | 2009-08-12 | Novartis Ag | Pharmaceutical compositions comprising an s1p modulator |
TW200906389A (en) * | 2007-05-25 | 2009-02-16 | Daiichi Sankyo Co Ltd | Pharmaceutical composition comprising of therapeutic or prophylactic agents for hepatitis |
MY159358A (en) | 2007-10-12 | 2016-12-30 | Novartis Ag | Compositions comprising sphingosine 1 phosphate (s1p) receptor modulators |
JP5452237B2 (ja) | 2008-02-07 | 2014-03-26 | 杏林製薬株式会社 | アミノアルコール誘導体を有効成分とする炎症性腸疾患の治療剤又は予防剤 |
CN103396346A (zh) * | 2008-05-19 | 2013-11-20 | 杏林制药株式会社 | 光学活性氨基醇衍生物的制备方法 |
US20110182850A1 (en) | 2009-04-10 | 2011-07-28 | Trixi Brandl | Organic compounds and their uses |
US8512690B2 (en) | 2009-04-10 | 2013-08-20 | Novartis Ag | Derivatised proline containing peptide compounds as protease inhibitors |
US9011833B2 (en) | 2010-10-08 | 2015-04-21 | Novartis Ag | Vitamin E formulations of sulfamide NS3 inhibitors |
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WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
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NO965193L (no) * | 1995-12-08 | 1997-06-09 | Seikagaku Kogyo Kk Seikagaku C | Aminalkoholderivat og fremgangsmåte for fremstilling derav |
DE59712095D1 (de) * | 1996-05-30 | 2004-12-30 | Lonza Ag Visp | Verfahren zur herstellung von aminoalkoholen und derivaten davon |
RU2198162C2 (ru) | 1997-04-04 | 2003-02-10 | Мицубиси Фарма Корпорейшн | Производное 2-аминопропан-1,3-диола, его фармацевтическое применение и промежуточные продукты для их синтеза |
US6214823B1 (en) * | 1997-10-17 | 2001-04-10 | Merck & Co., Inc. | Benzodiazepine derivatives as antiarrhythmic agents |
CZ200350A3 (cs) | 2000-07-13 | 2003-05-14 | Sankyo Company Limited | Aminoalkoholové deriváty |
JP2004507552A (ja) | 2000-08-31 | 2004-03-11 | メルク エンド カムパニー インコーポレーテッド | 免疫調節剤としてのリン酸誘導体 |
US20040058894A1 (en) | 2002-01-18 | 2004-03-25 | Doherty George A. | Selective S1P1/Edg1 receptor agonists |
-
2001
- 2001-07-10 CZ CZ200350A patent/CZ200350A3/cs unknown
- 2001-07-10 EP EP01947965A patent/EP1300405B1/en not_active Expired - Lifetime
- 2001-07-10 SK SK15-2003A patent/SK152003A3/sk not_active Application Discontinuation
- 2001-07-10 IL IL15359401A patent/IL153594A0/xx active IP Right Grant
- 2001-07-10 CN CNB2005100590917A patent/CN1328387C/zh not_active Expired - Fee Related
- 2001-07-10 MX MXPA03000397A patent/MXPA03000397A/es active IP Right Grant
- 2001-07-10 KR KR1020037000413A patent/KR100812578B1/ko not_active IP Right Cessation
- 2001-07-10 CA CA002415678A patent/CA2415678A1/en not_active Abandoned
- 2001-07-10 DE DE60127961T patent/DE60127961D1/de not_active Expired - Lifetime
- 2001-07-10 NZ NZ523554A patent/NZ523554A/xx unknown
- 2001-07-10 WO PCT/JP2001/005988 patent/WO2002006268A1/ja active IP Right Grant
- 2001-07-10 HU HU0301688A patent/HUP0301688A3/hu unknown
- 2001-07-10 BR BR0112484-6A patent/BR0112484A/pt not_active IP Right Cessation
- 2001-07-10 AU AU6950301A patent/AU6950301A/xx active Pending
- 2001-07-10 CN CNB018153402A patent/CN1267429C/zh not_active Expired - Fee Related
- 2001-07-10 AT AT01947965T patent/ATE360011T1/de not_active IP Right Cessation
- 2001-07-10 NZ NZ533997A patent/NZ533997A/en unknown
- 2001-07-10 PL PL01359411A patent/PL359411A1/xx unknown
- 2001-07-10 AU AU2001269503A patent/AU2001269503B2/en not_active Ceased
- 2001-07-12 TW TW090117073A patent/TWI301833B/zh active
-
2002
- 2002-12-22 IL IL153594A patent/IL153594A/en not_active IP Right Cessation
-
2003
- 2003-01-07 US US10/337,702 patent/US6723745B2/en not_active Expired - Fee Related
- 2003-01-10 NO NO20030120A patent/NO20030120L/no not_active Application Discontinuation
- 2003-05-06 HK HK03103214A patent/HK1051680A1/xx not_active IP Right Cessation
- 2003-11-20 US US10/718,858 patent/US6964976B2/en not_active Expired - Fee Related
-
2006
- 2006-03-30 IL IL174664A patent/IL174664A0/en unknown
Also Published As
Publication number | Publication date |
---|---|
ATE360011T1 (de) | 2007-05-15 |
CN1328387C (zh) | 2007-07-25 |
HUP0301688A3 (en) | 2006-05-29 |
DE60127961D1 (de) | 2007-05-31 |
NZ533997A (en) | 2005-11-25 |
US20040132784A1 (en) | 2004-07-08 |
KR20030047988A (ko) | 2003-06-18 |
KR100812578B1 (ko) | 2008-03-13 |
HK1051680A1 (en) | 2003-08-15 |
EP1300405B1 (en) | 2007-04-18 |
AU6950301A (en) | 2002-01-30 |
US6723745B2 (en) | 2004-04-20 |
CN1680563A (zh) | 2005-10-12 |
TWI301833B (en) | 2008-10-11 |
BR0112484A (pt) | 2003-09-23 |
HUP0301688A2 (hu) | 2003-09-29 |
NO20030120L (no) | 2003-03-11 |
IL153594A0 (en) | 2003-07-06 |
NZ523554A (en) | 2004-12-24 |
CA2415678A1 (en) | 2003-01-10 |
NO20030120D0 (no) | 2003-01-10 |
CN1267429C (zh) | 2006-08-02 |
IL174664A0 (en) | 2006-08-20 |
EP1300405A1 (en) | 2003-04-09 |
EP1300405A4 (en) | 2004-04-21 |
US20030236297A1 (en) | 2003-12-25 |
PL359411A1 (en) | 2004-08-23 |
MXPA03000397A (es) | 2003-05-27 |
US6964976B2 (en) | 2005-11-15 |
CN1494540A (zh) | 2004-05-05 |
WO2002006268A1 (fr) | 2002-01-24 |
AU2001269503B2 (en) | 2005-02-17 |
CZ200350A3 (cs) | 2003-05-14 |
IL153594A (en) | 2008-04-13 |
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