SK130599A3 - Novel pyridine derivatives and pharmaceutical compositions containing them - Google Patents

Info

Publication number

SK130599A3

SK130599A3 SK1305-99A SK130599A SK130599A3 SK 130599 A3 SK130599 A3 SK 130599A3 SK 130599 A SK130599 A SK 130599A SK 130599 A3 SK130599 A3 SK 130599A3

Authority

SK

Slovakia

Prior art keywords

pyridin

biphenyl

methyl

hydroxy

butoxy

Prior art date

1997-03-25

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
• 150000003222 pyridines Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 271
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
• 238000011282 treatment Methods 0.000 claims abstract description 23
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
• 239000001257 hydrogen Substances 0.000 claims abstract description 13
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 8
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
• 238000000034 method Methods 0.000 claims description 104
• -1 nitro, cyano, pyridyl Chemical group 0.000 claims description 94
• VVVJCILWEFJQJH-BLLLJJGKSA-N [4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]boronic acid Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C1=CC=C(B(O)O)C=C1 VVVJCILWEFJQJH-BLLLJJGKSA-N 0.000 claims description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
• 238000006243 chemical reaction Methods 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 206010039083 rhinitis Diseases 0.000 claims description 18
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 13
• 239000012453 solvate Substances 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 150000001408 amides Chemical class 0.000 claims description 9
• 125000006239 protecting group Chemical group 0.000 claims description 9
• 208000006673 asthma Diseases 0.000 claims description 8
• 230000009467 reduction Effects 0.000 claims description 8
• 239000004305 biphenyl Substances 0.000 claims description 7
• 235000010290 biphenyl Nutrition 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 claims description 6
• XZUSIPDBUGNOCM-HTAPYJJXSA-N (3r,4s)-4-(4-phenylphenoxy)-1-pyridin-3-ylpentan-3-ol Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 XZUSIPDBUGNOCM-HTAPYJJXSA-N 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 238000011321 prophylaxis Methods 0.000 claims description 4
• XZUSIPDBUGNOCM-VGOFRKELSA-N (3r,4r)-4-(4-phenylphenoxy)-1-pyridin-3-ylpentan-3-ol Chemical compound O([C@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 XZUSIPDBUGNOCM-VGOFRKELSA-N 0.000 claims description 3
• DJFWQIBUAVZYOE-RXFWQSSRSA-N (3r,4s)-1-pyridin-3-yl-4-[4-(3-pyrrolidin-1-ylsulfonylphenyl)phenoxy]pentan-3-ol Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C(C=1)=CC=CC=1S(=O)(=O)N1CCCC1 DJFWQIBUAVZYOE-RXFWQSSRSA-N 0.000 claims description 3
• ZCXVNJFAOLYGCZ-KSFYIVLOSA-N (3r,4s)-4-[4-(4-fluorophenyl)phenoxy]-1-pyridin-3-ylpentan-3-ol Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(F)C=C1 ZCXVNJFAOLYGCZ-KSFYIVLOSA-N 0.000 claims description 3
• UDULFYHNOLFOJX-UQBPGWFLSA-N (3r,4s)-4-[4-[4-[2-(methylamino)ethyl]phenyl]phenoxy]-1-pyridin-3-ylpentan-3-ol Chemical compound C1=CC(CCNC)=CC=C1C(C=C1)=CC=C1O[C@@H](C)[C@H](O)CCC1=CC=CN=C1 UDULFYHNOLFOJX-UQBPGWFLSA-N 0.000 claims description 3
• CXNZDHBVEUDSQV-UHFFFAOYSA-N 1-[1-(4-phenylphenoxy)cyclopropyl]-3-pyridin-3-ylpropan-1-ol Chemical compound C1CC1(OC=1C=CC(=CC=1)C=1C=CC=CC=1)C(O)CCC1=CC=CN=C1 CXNZDHBVEUDSQV-UHFFFAOYSA-N 0.000 claims description 3
• IJHMRBZSUOQSTK-KDYSTLNUSA-N 2-[3-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]phenyl]-1-morpholin-4-ylethanone Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C(C=1)=CC=CC=1CC(=O)N1CCOCC1 IJHMRBZSUOQSTK-KDYSTLNUSA-N 0.000 claims description 3
• DFFYDHKIRKXHRU-UQBPGWFLSA-N 2-[3-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]phenyl]-n,n-dimethylacetamide Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC(CC(=O)N(C)C)=C1 DFFYDHKIRKXHRU-UQBPGWFLSA-N 0.000 claims description 3
• BDBNIPOLEKIRTF-GAJHUEQPSA-N 3-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]benzonitrile Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC(C#N)=C1 BDBNIPOLEKIRTF-GAJHUEQPSA-N 0.000 claims description 3
• BDBNIPOLEKIRTF-SBUREZEXSA-N 3-[4-[(2s,3s)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]benzonitrile Chemical compound O([C@@H](C)[C@@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC(C#N)=C1 BDBNIPOLEKIRTF-SBUREZEXSA-N 0.000 claims description 3
• MAIBSRRVYSUFFI-MHECFPHRSA-N 3-[6-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxynaphthalen-2-yl]-n,n-dimethylprop-2-enamide Chemical compound C([C@@H](O)[C@@H](OC=1C=C2C=CC(C=CC(=O)N(C)C)=CC2=CC=1)C)CC1=CC=CN=C1 MAIBSRRVYSUFFI-MHECFPHRSA-N 0.000 claims description 3
• FUHNNVGGPVIYLB-GAJHUEQPSA-N 3-[6-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxynaphthalen-2-yl]-n-methylpropanamide Chemical compound C([C@@H](O)[C@H](C)OC1=CC2=CC=C(C=C2C=C1)CCC(=O)NC)CC1=CC=CN=C1 FUHNNVGGPVIYLB-GAJHUEQPSA-N 0.000 claims description 3
• 125000006267 biphenyl group Chemical group 0.000 claims description 3
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
• 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims description 3
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
• PYANXKKQTIRRIV-OYHNWAKOSA-N (3r,4s)-4-[4-(4-chloro-2-fluorophenyl)phenoxy]-1-pyridin-3-ylpentan-3-ol Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1F PYANXKKQTIRRIV-OYHNWAKOSA-N 0.000 claims description 2
• FXPVJVDIFNPJNT-RXFWQSSRSA-N (3r,4s)-4-[4-[3-[2-(dimethylamino)ethyl]phenyl]phenoxy]-1-pyridin-3-ylpentan-3-ol Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC(CCN(C)C)=C1 FXPVJVDIFNPJNT-RXFWQSSRSA-N 0.000 claims description 2
• BCEQYHJZIKPULS-KDYSTLNUSA-N (3r,4s)-4-[6-(3-morpholin-4-ylpropyl)naphthalen-2-yl]oxy-1-pyridin-3-ylpentan-3-ol Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1C=C2)=CC=C1C=C2CCCN1CCOCC1 BCEQYHJZIKPULS-KDYSTLNUSA-N 0.000 claims description 2
• XZUSIPDBUGNOCM-VGSWGCGISA-N (3s,4r)-4-(4-phenylphenoxy)-1-pyridin-3-ylpentan-3-ol Chemical compound O([C@H](C)[C@@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 XZUSIPDBUGNOCM-VGSWGCGISA-N 0.000 claims description 2
• YFLSMEPFKBSRIW-GAJHUEQPSA-N 1-[4-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(C=C1)=CC=C1O[C@@H](C)[C@H](O)CCC1=CC=CN=C1 YFLSMEPFKBSRIW-GAJHUEQPSA-N 0.000 claims description 2
• YKFCAHCDMIJARA-MHECFPHRSA-N 2-[2-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]phenyl]-n-methylacetamide Chemical compound CNC(=O)CC1=CC=CC=C1C(C=C1)=CC=C1O[C@@H](C)[C@H](O)CCC1=CC=CN=C1 YKFCAHCDMIJARA-MHECFPHRSA-N 0.000 claims description 2
• JPMVIYLNKGWFBU-QMHKHESXSA-N 2-chloro-4-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]benzonitrile Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C(Cl)=C1 JPMVIYLNKGWFBU-QMHKHESXSA-N 0.000 claims description 2
• HHEQAVXKLSNFNE-QMHKHESXSA-N 2-fluoro-4-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]benzonitrile Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C(F)=C1 HHEQAVXKLSNFNE-QMHKHESXSA-N 0.000 claims description 2
• GROMYTOXVHFGDL-QMHKHESXSA-N 2-fluoro-5-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]benzonitrile Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(F)C(C#N)=C1 GROMYTOXVHFGDL-QMHKHESXSA-N 0.000 claims description 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
• BPXRZTHFLMDHQW-GAJHUEQPSA-N 3-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1C(C=C1)=CC=C1O[C@@H](C)[C@H](O)CCC1=CC=CN=C1 BPXRZTHFLMDHQW-GAJHUEQPSA-N 0.000 claims description 2
• KKLCPJYXDRNFHY-RPBOFIJWSA-N 3-[4-[(3s,4r)-4-hydroxy-2-methyl-6-pyridin-3-ylhexan-3-yl]oxyphenyl]benzonitrile Chemical compound O([C@@H](C(C)C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC(C#N)=C1 KKLCPJYXDRNFHY-RPBOFIJWSA-N 0.000 claims description 2
• ZIZHLOXKPFDUBA-UHFFFAOYSA-N 3-phenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 ZIZHLOXKPFDUBA-UHFFFAOYSA-N 0.000 claims description 2
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• VJNJWMIMSQRILY-KSFYIVLOSA-N [4-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]phenyl]urea Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(NC(N)=O)C=C1 VJNJWMIMSQRILY-KSFYIVLOSA-N 0.000 claims description 2
• 125000003118 aryl group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• XJMBIODSTYUTCE-UPCLLVRISA-N n-[2-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]-4-(trifluoromethyl)phenyl]acetamide Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC(C(F)(F)F)=CC=C1NC(C)=O XJMBIODSTYUTCE-UPCLLVRISA-N 0.000 claims description 2
• DSGWFDHAIIQHTB-AVRWGWEMSA-N n-[4-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]-3-methylphenyl]acetamide Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(NC(C)=O)C=C1C DSGWFDHAIIQHTB-AVRWGWEMSA-N 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 239000001301 oxygen Chemical group 0.000 claims description 2
• 239000011593 sulfur Chemical group 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 8
• SYHJILPZUNKNHQ-UHFFFAOYSA-N 3-phenylbenzonitrile Chemical compound N#CC1=CC=CC(C=2C=CC=CC=2)=C1 SYHJILPZUNKNHQ-UHFFFAOYSA-N 0.000 claims 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
• YXFVAPZXRHIFCH-MHECFPHRSA-N (3r,4s)-4-[6-[3-(methylamino)propyl]naphthalen-2-yl]oxy-1-pyridin-3-ylpentan-3-ol Chemical compound C([C@@H](O)[C@H](C)OC1=CC2=CC=C(C=C2C=C1)CCCNC)CC1=CC=CN=C1 YXFVAPZXRHIFCH-MHECFPHRSA-N 0.000 claims 1
• TZCZHPIFEFVHQO-AOMKIAJQSA-N (3s,4s)-4-[4-(3-chlorophenyl)phenoxy]-1-pyridin-3-ylpentan-3-ol Chemical compound O([C@@H](C)[C@@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=CC(Cl)=C1 TZCZHPIFEFVHQO-AOMKIAJQSA-N 0.000 claims 1
• XJJDMRUBNAKIAG-LHSJRXKWSA-N 2,5-difluoro-4-[4-[(2S,3R)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]benzenesulfonic acid Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC(F)=C(S(O)(=O)=O)C=C1F XJJDMRUBNAKIAG-LHSJRXKWSA-N 0.000 claims 1
• XNLWJFYYOIRPIO-UHFFFAOYSA-N 3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 XNLWJFYYOIRPIO-UHFFFAOYSA-N 0.000 claims 1
• UABNFGKHVUBOGX-MHECFPHRSA-N 4-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]-2-methylbenzonitrile Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C(C)=C1 UABNFGKHVUBOGX-MHECFPHRSA-N 0.000 claims 1
• YLRTWQXHZYQDGS-BXKMTCNYSA-N 4-[4-[(2s,3r)-3-hydroxy-5-pyridin-3-ylpentan-2-yl]oxyphenyl]benzene-1,2-dicarbonitrile Chemical compound O([C@@H](C)[C@H](O)CCC=1C=NC=CC=1)C(C=C1)=CC=C1C1=CC=C(C#N)C(C#N)=C1 YLRTWQXHZYQDGS-BXKMTCNYSA-N 0.000 claims 1
• JVFCCRJSBNUDDU-UHFFFAOYSA-N 4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 JVFCCRJSBNUDDU-UHFFFAOYSA-N 0.000 claims 1
• XDTYUYVIGLIFCW-UHFFFAOYSA-N 4-phenylbenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=CC=C1 XDTYUYVIGLIFCW-UHFFFAOYSA-N 0.000 claims 1
• FATLFCBRPHTLOU-OYHNWAKOSA-N C[C@@H]([C@@H](CCC1=CN=CC=C1)O)OC2=CC=C(C=C2)C3=CC(=C(C=C3)F)C(=O)O Chemical compound C[C@@H]([C@@H](CCC1=CN=CC=C1)O)OC2=CC=C(C=C2)C3=CC(=C(C=C3)F)C(=O)O FATLFCBRPHTLOU-OYHNWAKOSA-N 0.000 claims 1
• 239000002671 adjuvant Substances 0.000 claims 1
• 125000002877 alkyl aryl group Chemical group 0.000 claims 1
• 239000004202 carbamide Substances 0.000 claims 1
• 230000000172 allergic effect Effects 0.000 abstract description 16
• 230000002265 prevention Effects 0.000 abstract description 13
• 230000002757 inflammatory effect Effects 0.000 abstract description 11
• 208000010668 atopic eczema Diseases 0.000 abstract description 8
• 201000010099 disease Diseases 0.000 abstract description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
• 230000001363 autoimmune Effects 0.000 abstract description 3
• 230000002062 proliferating effect Effects 0.000 abstract description 3
• 230000003463 hyperproliferative effect Effects 0.000 abstract description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 480
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 438
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 288
• 239000000243 solution Substances 0.000 description 209
• 238000005481 NMR spectroscopy Methods 0.000 description 160
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 156
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 139
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 131
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 126
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 124
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 123
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
• 239000000203 mixture Substances 0.000 description 107
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 96
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 93
• 239000007787 solid Substances 0.000 description 88
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
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