JP4982367B2 - ヒスタミンｈ３受容体薬剤としてのオキサゾール誘導体、製造及び治療的使用 - Google Patents

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Publication number

JP4982367B2

JP4982367B2 JP2007523605A JP2007523605A JP4982367B2 JP 4982367 B2 JP4982367 B2 JP 4982367B2 JP 2007523605 A JP2007523605 A JP 2007523605A JP 2007523605 A JP2007523605 A JP 2007523605A JP 4982367 B2 JP4982367 B2 JP 4982367B2

Authority

JP

Japan

Prior art keywords

methyl

ethyl

pyrrolidin

oxazol

phenyl

Prior art date

2004-07-26

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 102000004384 Histamine H3 receptors Human genes 0.000 title abstract description 54
• 108090000981 Histamine H3 receptors Proteins 0.000 title abstract description 54
• 239000003814 drug Substances 0.000 title description 11
• 238000004519 manufacturing process Methods 0.000 title description 10
• 230000001225 therapeutic effect Effects 0.000 title description 4
• 229940079593 drug Drugs 0.000 title description 2
• 150000007978 oxazole derivatives Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 340
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 228
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 154
• -1 aryl oxazole compounds Chemical class 0.000 claims abstract description 142
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 117
• 150000002367 halogens Chemical class 0.000 claims abstract description 90
• 150000003839 salts Chemical class 0.000 claims abstract description 86
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 73
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 37
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
• 239000001257 hydrogen Substances 0.000 claims abstract description 28
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 20
• 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 63
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
• ZQHAWHYNSSTKBW-UHFFFAOYSA-N 2-(4-bromophenyl)-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CCCC1 ZQHAWHYNSSTKBW-UHFFFAOYSA-N 0.000 claims description 22
• 125000004429 atom Chemical group 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• SABSEDJLQPMDJT-LLVKDONJSA-N 2-[2-(4-hydroxyphenyl)-5-methyl-1,3-oxazol-4-yl]-1-[(2R)-2-methylpyrrolidin-1-yl]ethanone Chemical compound C[C@@H]1CCCN1C(=O)CC1=C(C)OC(C=2C=CC(O)=CC=2)=N1 SABSEDJLQPMDJT-LLVKDONJSA-N 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
• JOMAJALOGDGCDX-UHFFFAOYSA-N 2-(4-bromophenyl)-5-methyl-4-(2-piperidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CCCCC1 JOMAJALOGDGCDX-UHFFFAOYSA-N 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• ZOPPZXGVEAGAGO-UHFFFAOYSA-N 2-(4-bromophenyl)-4-(pyrrolidin-1-ylmethyl)-1,3-oxazole Chemical compound C1=CC(Br)=CC=C1C1=NC(CN2CCCC2)=CO1 ZOPPZXGVEAGAGO-UHFFFAOYSA-N 0.000 claims description 6
• FVDZPPXQHHXRFL-UHFFFAOYSA-N 2-[2-fluoro-4-(4-methylsulfonylphenyl)phenyl]-5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-1,3-oxazole Chemical compound CC1CCCN1CCC1=C(C)OC(C=2C(=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)F)=N1 FVDZPPXQHHXRFL-UHFFFAOYSA-N 0.000 claims description 6
• DWCMEMKNYOOASW-UHFFFAOYSA-N 4-[(2-methylpiperidin-1-yl)methyl]-2-(4-pyridin-3-ylphenyl)-1,3-oxazole Chemical compound CC1CCCCN1CC1=COC(C=2C=CC(=CC=2)C=2C=NC=CC=2)=N1 DWCMEMKNYOOASW-UHFFFAOYSA-N 0.000 claims description 6
• PXXOFVULQPKAFY-UHFFFAOYSA-N 5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-2-[4-(5-methylsulfonylpyrimidin-2-yl)phenyl]-1,3-oxazole Chemical compound CC1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2N=CC(=CN=2)S(C)(=O)=O)=N1 PXXOFVULQPKAFY-UHFFFAOYSA-N 0.000 claims description 6
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 5
• WUOQJWYFYRVOQG-UHFFFAOYSA-N 5-methyl-2-(4-pyridin-3-ylphenyl)-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=NC=CC=2)=NC=1CCN1CCCC1 WUOQJWYFYRVOQG-UHFFFAOYSA-N 0.000 claims description 5
• DBBLNORBARGSIV-UHFFFAOYSA-N 2-(4-bromophenyl)-4-[(2-methylpyrrolidin-1-yl)methyl]-1,3-oxazole Chemical compound CC1CCCN1CC1=COC(C=2C=CC(Br)=CC=2)=N1 DBBLNORBARGSIV-UHFFFAOYSA-N 0.000 claims description 4
• FSIXEANSDLCWFE-INIZCTEOSA-N 2-(4-bromophenyl)-4-[2-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound COC[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(Br)=CC=2)=N1 FSIXEANSDLCWFE-INIZCTEOSA-N 0.000 claims description 4
• FRNHUPQHPUNPMX-AWEZNQCLSA-N 2-(4-bromophenyl)-4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CC[C@H](F)C1 FRNHUPQHPUNPMX-AWEZNQCLSA-N 0.000 claims description 4
• IDJGCIZLIAHASA-UHFFFAOYSA-N 2-(4-bromophenyl)-5-methyl-4-[(2-methylpyrrolidin-1-yl)methyl]-1,3-oxazole Chemical compound CC1CCCN1CC1=C(C)OC(C=2C=CC(Br)=CC=2)=N1 IDJGCIZLIAHASA-UHFFFAOYSA-N 0.000 claims description 4
• COTJCXDLLSTAGF-UHFFFAOYSA-N 5-[4-[5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazol-2-yl]phenyl]thiophene-2-carbonitrile Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC(=CC=2)C#N)=NC=1CCN1CCCC1 COTJCXDLLSTAGF-UHFFFAOYSA-N 0.000 claims description 4
• RNVDHESPLZUDOK-CYBMUJFWSA-N C[C@@H]1C=CC=CN1CCC2=C(OC(=N2)C3=CC=C(C=C3)Br)C Chemical compound C[C@@H]1C=CC=CN1CCC2=C(OC(=N2)C3=CC=C(C=C3)Br)C RNVDHESPLZUDOK-CYBMUJFWSA-N 0.000 claims description 4
• 239000003610 charcoal Substances 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• MICQGJKVPCGWME-CQSZACIVSA-N (3r)-1-[2-[2-(4-bromophenyl)-5-methyl-1,3-oxazol-4-yl]ethyl]pyrrolidin-3-ol Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CC[C@@H](O)C1 MICQGJKVPCGWME-CQSZACIVSA-N 0.000 claims description 3
• MICQGJKVPCGWME-AWEZNQCLSA-N (3s)-1-[2-[2-(4-bromophenyl)-5-methyl-1,3-oxazol-4-yl]ethyl]pyrrolidin-3-ol Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CC[C@H](O)C1 MICQGJKVPCGWME-AWEZNQCLSA-N 0.000 claims description 3
• UECPFNWCBRYYAC-UHFFFAOYSA-N 2-(4-bromophenyl)-4-[(2-methylpiperidin-1-yl)methyl]-1,3-oxazole Chemical compound CC1CCCCN1CC1=COC(C=2C=CC(Br)=CC=2)=N1 UECPFNWCBRYYAC-UHFFFAOYSA-N 0.000 claims description 3
• FRNHUPQHPUNPMX-CQSZACIVSA-N 2-(4-bromophenyl)-4-[2-[(3r)-3-fluoropyrrolidin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CC[C@@H](F)C1 FRNHUPQHPUNPMX-CQSZACIVSA-N 0.000 claims description 3
• MPBSYZUYPXIEOJ-OAHLLOKOSA-N 2-(4-bromophenyl)-4-[2-[(3r)-3-methoxypyrrolidin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound C1[C@H](OC)CCN1CCC1=C(C)OC(C=2C=CC(Br)=CC=2)=N1 MPBSYZUYPXIEOJ-OAHLLOKOSA-N 0.000 claims description 3
• MPBSYZUYPXIEOJ-HNNXBMFYSA-N 2-(4-bromophenyl)-4-[2-[(3s)-3-methoxypyrrolidin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound C1[C@@H](OC)CCN1CCC1=C(C)OC(C=2C=CC(Br)=CC=2)=N1 MPBSYZUYPXIEOJ-HNNXBMFYSA-N 0.000 claims description 3
• JFFRMXVSZNDWHV-UHFFFAOYSA-N 2-(4-butoxyphenyl)-5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-1,3-oxazole Chemical compound C1=CC(OCCCC)=CC=C1C1=NC(CCN2C(CCC2)C)=C(C)O1 JFFRMXVSZNDWHV-UHFFFAOYSA-N 0.000 claims description 3
• IIIXEWWPXMWAGN-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)phenyl]-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=C3OCOC3=CC=2)=NC=1CCN1CCCC1 IIIXEWWPXMWAGN-UHFFFAOYSA-N 0.000 claims description 3
• BHBCJUIODDRDPE-UHFFFAOYSA-N 2-[4-(1h-indol-5-yl)phenyl]-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=C3C=CNC3=CC=2)=NC=1CCN1CCCC1 BHBCJUIODDRDPE-UHFFFAOYSA-N 0.000 claims description 3
• XCQJHTROCVDVJD-UHFFFAOYSA-N 2-[4-(2,4-dimethoxyphenyl)phenyl]-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound COC1=CC(OC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3CCCC3)N=2)C=C1 XCQJHTROCVDVJD-UHFFFAOYSA-N 0.000 claims description 3
• GLPAGVRWLJFEQY-UHFFFAOYSA-N 2-[4-(2-methoxypyrimidin-5-yl)phenyl]-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound C1=NC(OC)=NC=C1C1=CC=C(C=2OC(C)=C(CCN3CCCC3)N=2)C=C1 GLPAGVRWLJFEQY-UHFFFAOYSA-N 0.000 claims description 3
• WODKPKSFCAELCK-UHFFFAOYSA-N 2-[4-(3,4-dimethoxyphenyl)phenyl]-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3CCCC3)N=2)C=C1 WODKPKSFCAELCK-UHFFFAOYSA-N 0.000 claims description 3
• HCXOVGVPZQKYER-UHFFFAOYSA-N 2-[4-(4-ethylsulfonylphenyl)phenyl]-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3CCCC3)N=2)C=C1 HCXOVGVPZQKYER-UHFFFAOYSA-N 0.000 claims description 3
• MEBITIMISJKINQ-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)phenyl]-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3CCCC3)N=2)C=C1 MEBITIMISJKINQ-UHFFFAOYSA-N 0.000 claims description 3
• BNIMUZFIPREDRE-UHFFFAOYSA-N 2-[4-(4-methylsulfonylphenyl)phenyl]-4-(pyrrolidin-1-ylmethyl)-1,3-oxazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(C=2OC=C(CN3CCCC3)N=2)C=C1 BNIMUZFIPREDRE-UHFFFAOYSA-N 0.000 claims description 3
• ANGHUYMRQZFOTA-UHFFFAOYSA-N 2-[4-(5-methoxypyridin-3-yl)phenyl]-5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound COC1=CN=CC(C=2C=CC(=CC=2)C=2OC(C)=C(CCN3CCCC3)N=2)=C1 ANGHUYMRQZFOTA-UHFFFAOYSA-N 0.000 claims description 3
• IBKCXKFATRQNMC-UHFFFAOYSA-N 2-[4-(6-ethylsulfonylpyridazin-3-yl)phenyl]-5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-1,3-oxazole Chemical compound N1=NC(S(=O)(=O)CC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3C(CCC3)C)N=2)C=C1 IBKCXKFATRQNMC-UHFFFAOYSA-N 0.000 claims description 3
• XFYMQPWRJWRHQJ-QGZVFWFLSA-N 2-[4-(6-ethylsulfonylpyridin-3-yl)phenyl]-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole Chemical compound C1=NC(S(=O)(=O)CC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3[C@@H](CCC3)C)N=2)C=C1 XFYMQPWRJWRHQJ-QGZVFWFLSA-N 0.000 claims description 3
• SZIRCEZOLYFLPF-UHFFFAOYSA-N 2-[4-(6-methoxypyridazin-3-yl)phenyl]-5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-1,3-oxazole Chemical compound N1=NC(OC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3C(CCC3)C)N=2)C=C1 SZIRCEZOLYFLPF-UHFFFAOYSA-N 0.000 claims description 3
• AZGPGRVSPHCQBC-QGZVFWFLSA-N 2-[4-[(6-methoxypyridin-3-yl)methoxy]phenyl]-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole Chemical compound C1=NC(OC)=CC=C1COC1=CC=C(C=2OC(C)=C(CCN3[C@@H](CCC3)C)N=2)C=C1 AZGPGRVSPHCQBC-QGZVFWFLSA-N 0.000 claims description 3
• VYBUHYWUUBENJQ-UHFFFAOYSA-N 4-[(2-methylpyrrolidin-1-yl)methyl]-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound CC1CCCN1CC1=COC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 VYBUHYWUUBENJQ-UHFFFAOYSA-N 0.000 claims description 3
• DACDXNMWMCYASS-UHFFFAOYSA-N 4-[2-(azetidin-1-yl)ethyl]-2-(4-bromophenyl)-5-methyl-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CCC1 DACDXNMWMCYASS-UHFFFAOYSA-N 0.000 claims description 3
• QWVFQYXIBZLFFD-UHFFFAOYSA-N 5-methyl-2-(4-pyridin-4-ylphenyl)-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=NC=1CCN1CCCC1 QWVFQYXIBZLFFD-UHFFFAOYSA-N 0.000 claims description 3
• JYTGVRAYYPWULP-UHFFFAOYSA-N 5-methyl-2-(4-pyrimidin-5-ylphenyl)-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=NC=NC=2)=NC=1CCN1CCCC1 JYTGVRAYYPWULP-UHFFFAOYSA-N 0.000 claims description 3
• DMBKFKXJPIAVJG-UHFFFAOYSA-N 5-methyl-2-[4-(4-methylsulfinylphenyl)phenyl]-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)=O)=NC=1CCN1CCCC1 DMBKFKXJPIAVJG-UHFFFAOYSA-N 0.000 claims description 3
• CORBMAGBQIYLDA-UHFFFAOYSA-N 5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCN1CCCC1 CORBMAGBQIYLDA-UHFFFAOYSA-N 0.000 claims description 3
• QOHSGSRDPKOSAV-UHFFFAOYSA-N 5-methyl-4-(2-pyrrolidin-1-ylethyl)-2-(4-thiophen-2-ylphenyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2SC=CC=2)=NC=1CCN1CCCC1 QOHSGSRDPKOSAV-UHFFFAOYSA-N 0.000 claims description 3
• ZLFVNQOKFCOVPR-UHFFFAOYSA-N 5-methyl-4-(2-pyrrolidin-1-ylethyl)-2-[4-[3-(trifluoromethyl)phenyl]phenyl]-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC=1CCN1CCCC1 ZLFVNQOKFCOVPR-UHFFFAOYSA-N 0.000 claims description 3
• WPGWVQNAVRCBMJ-UHFFFAOYSA-N 5-methyl-4-(2-pyrrolidin-1-ylethyl)-2-[4-[4-(trifluoromethoxy)phenyl]phenyl]-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC(OC(F)(F)F)=CC=2)=NC=1CCN1CCCC1 WPGWVQNAVRCBMJ-UHFFFAOYSA-N 0.000 claims description 3
• FZIRZESUMSPTGC-UHFFFAOYSA-N 5-methyl-4-[(2-methylpyrrolidin-1-yl)methyl]-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound CC1CCCN1CC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 FZIRZESUMSPTGC-UHFFFAOYSA-N 0.000 claims description 3
• VDIBZWGODBHBAG-UHFFFAOYSA-N 5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-2-[4-(6-methylsulfonylpyridazin-3-yl)phenyl]-1,3-oxazole Chemical compound CC1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2N=NC(=CC=2)S(C)(=O)=O)=N1 VDIBZWGODBHBAG-UHFFFAOYSA-N 0.000 claims description 3
• JEFWYNMTOAJJBY-MRXNPFEDSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(6-methylsulfonylpyridin-3-yl)phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=NC(=CC=2)S(C)(=O)=O)=N1 JEFWYNMTOAJJBY-MRXNPFEDSA-N 0.000 claims description 3
• RSCAKONZKZJPDZ-QGZVFWFLSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(pyridin-2-ylmethoxy)phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3N=CC=CC=3)=CC=2)=N1 RSCAKONZKZJPDZ-QGZVFWFLSA-N 0.000 claims description 3
• WDPUMNOWOKKVTB-QGZVFWFLSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(pyridin-4-ylmethoxy)phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3C=CN=CC=3)=CC=2)=N1 WDPUMNOWOKKVTB-QGZVFWFLSA-N 0.000 claims description 3
• YVZRPKIZSPNLGF-UHFFFAOYSA-N n,n-dimethyl-2-[5-methyl-2-[6-(4-methylsulfonylphenyl)pyridin-3-yl]-1,3-oxazol-4-yl]ethanamine Chemical compound O1C(C)=C(CCN(C)C)N=C1C1=CC=C(C=2C=CC(=CC=2)S(C)(=O)=O)N=C1 YVZRPKIZSPNLGF-UHFFFAOYSA-N 0.000 claims description 3
• QFJZCCOPHHBYDN-UHFFFAOYSA-N n,n-dimethyl-6-[4-[5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-1,3-oxazol-2-yl]phenyl]pyridine-3-carboxamide Chemical compound CC1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2N=CC(=CC=2)C(=O)N(C)C)=N1 QFJZCCOPHHBYDN-UHFFFAOYSA-N 0.000 claims description 3
• 125000003944 tolyl group Chemical group 0.000 claims description 3
• VMOBXAJMQIVRJM-YRSVLNEHSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;5-[2-[(3r)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl]-4-methyl-2-(4-pyridin-3-ylphenyl)-1,3-oxazole Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CC=1N=C(C=2C=CC(=CC=2)C=2C=NC=CC=2)OC=1CCN1CC[C@@H](CF)C1 VMOBXAJMQIVRJM-YRSVLNEHSA-N 0.000 claims description 2
• JUHFDQPYEFCYSQ-UNTBIKODSA-N 1-[3-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]phenyl]ethanone;hydrochloride Chemical compound Cl.C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(C)=O)=N1 JUHFDQPYEFCYSQ-UNTBIKODSA-N 0.000 claims description 2
• HIULMVXQSXLIGX-NWXNRHFJSA-N 1-[5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazol-4-yl]-2-[(2r)-2-methylpyrrolidin-1-yl]ethanol;hydrochloride Chemical compound Cl.C[C@@H]1CCCN1CC(O)C1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 HIULMVXQSXLIGX-NWXNRHFJSA-N 0.000 claims description 2
• VFPLGSCTZVTJJT-UHFFFAOYSA-N 2-(4-bromophenyl)-4-(pyrrolidin-1-ylmethyl)-1,3-oxazole;hydrochloride Chemical compound Cl.C1=CC(Br)=CC=C1C1=NC(CN2CCCC2)=CO1 VFPLGSCTZVTJJT-UHFFFAOYSA-N 0.000 claims description 2
• FSIXEANSDLCWFE-MRXNPFEDSA-N 2-(4-bromophenyl)-4-[2-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound COC[C@H]1CCCN1CCC1=C(C)OC(C=2C=CC(Br)=CC=2)=N1 FSIXEANSDLCWFE-MRXNPFEDSA-N 0.000 claims description 2
• KMSSCDKVOZSLGJ-ZDUSSCGKSA-N 2-(4-bromophenyl)-4-[2-[(3r)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CC[C@@H](CF)C1 KMSSCDKVOZSLGJ-ZDUSSCGKSA-N 0.000 claims description 2
• KMSSCDKVOZSLGJ-CYBMUJFWSA-N 2-(4-bromophenyl)-4-[2-[(3s)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(Br)=CC=2)=NC=1CCN1CC[C@H](CF)C1 KMSSCDKVOZSLGJ-CYBMUJFWSA-N 0.000 claims description 2
• RTURCQXKAOUJCJ-UHFFFAOYSA-N 2-[2-fluoro-4-(4-methylsulfonylphenyl)phenyl]-5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-1,3-oxazole;hydrochloride Chemical compound Cl.CC1CCCN1CCC1=C(C)OC(C=2C(=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)F)=N1 RTURCQXKAOUJCJ-UHFFFAOYSA-N 0.000 claims description 2
• ULOSFQVHRPYZKP-MRXNPFEDSA-N 2-[4-(3-fluorophenyl)phenyl]-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=C(F)C=CC=2)=N1 ULOSFQVHRPYZKP-MRXNPFEDSA-N 0.000 claims description 2
• DNYFVAZBDSBQIB-ZEECNFPPSA-N 2-[4-(6-ethylsulfonylpyridin-3-yl)phenyl]-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole;dihydrochloride Chemical compound Cl.Cl.C1=NC(S(=O)(=O)CC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3[C@@H](CCC3)C)N=2)C=C1 DNYFVAZBDSBQIB-ZEECNFPPSA-N 0.000 claims description 2
• OCXNMKKNTYORCF-UHFFFAOYSA-N 2-methyl-5-[4-[4-[5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazol-2-yl]phenyl]phenyl]-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1C1=CC=C(C=2C=CC(=CC=2)C=2OC(C)=C(CCN3CCCC3)N=2)C=C1 OCXNMKKNTYORCF-UHFFFAOYSA-N 0.000 claims description 2
• VJVJMKAODWLOHF-UHFFFAOYSA-N 3-[4-[5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazol-2-yl]phenyl]benzonitrile Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=C(C=CC=2)C#N)=NC=1CCN1CCCC1 VJVJMKAODWLOHF-UHFFFAOYSA-N 0.000 claims description 2
• QHBUIKJGDXBRNX-BAHXIVKCSA-N 4-[1-methoxy-2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole;hydrochloride Chemical compound Cl.N1=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)OC(C)=C1C(OC)CN1CCC[C@H]1C QHBUIKJGDXBRNX-BAHXIVKCSA-N 0.000 claims description 2
• RGCOILXWPFRXBZ-JOCHJYFZSA-N 4-[2-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound COC[C@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 RGCOILXWPFRXBZ-JOCHJYFZSA-N 0.000 claims description 2
• RKZANTTXFTXEMF-FGJQBABTSA-N 4-[2-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]ethyl]-5-methyl-2-(4-pyridin-3-ylphenyl)-1,3-oxazole;dihydrochloride Chemical compound Cl.Cl.COC[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=NC=CC=2)=N1 RKZANTTXFTXEMF-FGJQBABTSA-N 0.000 claims description 2
• NBHCMDQTYSZQIU-FGJQBABTSA-N 4-[2-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]ethyl]-5-methyl-2-(4-pyridin-4-ylphenyl)-1,3-oxazole;dihydrochloride Chemical compound Cl.Cl.COC[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=N1 NBHCMDQTYSZQIU-FGJQBABTSA-N 0.000 claims description 2
• RGCOILXWPFRXBZ-QFIPXVFZSA-N 4-[2-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound COC[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 RGCOILXWPFRXBZ-QFIPXVFZSA-N 0.000 claims description 2
• RHZAZKPKWSOQBS-SFHVURJKSA-N 4-[2-[(3r)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCN1CC[C@@H](CF)C1 RHZAZKPKWSOQBS-SFHVURJKSA-N 0.000 claims description 2
• GXDISHAMZOCVSX-HXUWFJFHSA-N 4-[2-[(3r)-3-fluoropyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCN1CC[C@@H](F)C1 GXDISHAMZOCVSX-HXUWFJFHSA-N 0.000 claims description 2
• FWDCGNMZVRUNJR-OAQYLSRUSA-N 4-[2-[(3r)-3-methoxypyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound C1[C@H](OC)CCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 FWDCGNMZVRUNJR-OAQYLSRUSA-N 0.000 claims description 2
• RHZAZKPKWSOQBS-GOSISDBHSA-N 4-[2-[(3s)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCN1CC[C@H](CF)C1 RHZAZKPKWSOQBS-GOSISDBHSA-N 0.000 claims description 2
• FWDCGNMZVRUNJR-NRFANRHFSA-N 4-[2-[(3s)-3-methoxypyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound C1[C@@H](OC)CCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 FWDCGNMZVRUNJR-NRFANRHFSA-N 0.000 claims description 2
• XUDJAINDJLYSDG-MRXNPFEDSA-N 5-[[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenoxy]methyl]thiophene-2-carbonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3SC(=CC=3)C#N)=CC=2)=N1 XUDJAINDJLYSDG-MRXNPFEDSA-N 0.000 claims description 2
• LYCMUVQHQUFYDA-UHFFFAOYSA-N 5-methyl-2-(4-pyridin-4-ylphenyl)-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole;dihydrochloride Chemical compound Cl.Cl.CC=1OC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=NC=1CCN1CCCC1 LYCMUVQHQUFYDA-UHFFFAOYSA-N 0.000 claims description 2
• JXVAYMCUDSPCDA-UHFFFAOYSA-N 5-methyl-2-[4-(3-methylsulfonylphenyl)phenyl]-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(=CC=2)C=2C=C(C=CC=2)S(C)(=O)=O)=NC=1CCN1CCCC1 JXVAYMCUDSPCDA-UHFFFAOYSA-N 0.000 claims description 2
• LBAIGEKYNBBVCW-GOSISDBHSA-N 5-methyl-2-[4-(4-methylphenyl)phenyl]-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(C)=CC=2)=N1 LBAIGEKYNBBVCW-GOSISDBHSA-N 0.000 claims description 2
• SNOGDMOAUXBHFR-UHFFFAOYSA-N 5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-4-(2-piperidin-1-ylethyl)-1,3-oxazole;hydrochloride Chemical compound Cl.CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCN1CCCCC1 SNOGDMOAUXBHFR-UHFFFAOYSA-N 0.000 claims description 2
• UKHLYHUZOWNNMO-UHFFFAOYSA-N 5-methyl-2-[4-(6-methylpyridazin-3-yl)phenyl]-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-1,3-oxazole Chemical compound CC1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2N=NC(C)=CC=2)=N1 UKHLYHUZOWNNMO-UHFFFAOYSA-N 0.000 claims description 2
• DUZYFCIOTNAMJA-UHFFFAOYSA-N 5-methyl-2-[4-(pyridin-2-ylmethoxy)phenyl]-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(OCC=3N=CC=CC=3)=CC=2)=NC=1CCN1CCCC1 DUZYFCIOTNAMJA-UHFFFAOYSA-N 0.000 claims description 2
• DPJKNWPXHVYBDR-GOSISDBHSA-N 5-methyl-2-[4-[(6-methylpyridin-2-yl)methoxy]phenyl]-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3N=C(C)C=CC=3)=CC=2)=N1 DPJKNWPXHVYBDR-GOSISDBHSA-N 0.000 claims description 2
• FNPPMLSUFIBSNI-UHFFFAOYSA-N 5-methyl-4-[2-(2-methylpiperidin-1-yl)ethyl]-2-(4-pyridin-4-ylphenyl)-1,3-oxazole;hydrochloride Chemical compound Cl.CC1CCCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=N1 FNPPMLSUFIBSNI-UHFFFAOYSA-N 0.000 claims description 2
• VELSUFWFSPOTDF-UHFFFAOYSA-N 5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-2-(4-pyridin-2-ylphenyl)-1,3-oxazole Chemical compound CC1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2N=CC=CC=2)=N1 VELSUFWFSPOTDF-UHFFFAOYSA-N 0.000 claims description 2
• DCOFCFIDHZSKKE-UHFFFAOYSA-N 5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-2-(6-phenoxypyridin-3-yl)-1,3-oxazole Chemical compound CC1CCCN1CCC1=C(C)OC(C=2C=NC(OC=3C=CC=CC=3)=CC=2)=N1 DCOFCFIDHZSKKE-UHFFFAOYSA-N 0.000 claims description 2
• TVCJOVWBAJTPDX-UHFFFAOYSA-N 5-methyl-4-[2-(2-methylpyrrolidin-1-yl)ethyl]-2-[4-(5-methylsulfonylpyrimidin-2-yl)phenyl]-1,3-oxazole;hydrochloride Chemical compound Cl.CC1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2N=CC(=CN=2)S(C)(=O)=O)=N1 TVCJOVWBAJTPDX-UHFFFAOYSA-N 0.000 claims description 2
• POKMLXUAAIJTAR-GMUIIQOCSA-N 5-methyl-4-[2-[(2r)-2-methylpiperidin-1-yl]ethyl]-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole;hydrochloride Chemical compound Cl.C[C@@H]1CCCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 POKMLXUAAIJTAR-GMUIIQOCSA-N 0.000 claims description 2
• OSEMMWNCCXETAD-GOSISDBHSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-(4-phenylmethoxyphenyl)-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 OSEMMWNCCXETAD-GOSISDBHSA-N 0.000 claims description 2
• QEHLIYQNAWKFEQ-MRXNPFEDSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-(4-pyridin-3-ylphenyl)-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=NC=CC=2)=N1 QEHLIYQNAWKFEQ-MRXNPFEDSA-N 0.000 claims description 2
• MJQLMOJCPDUURZ-OAHLLOKOSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(1,3-thiazol-4-ylmethoxy)phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3N=CSC=3)=CC=2)=N1 MJQLMOJCPDUURZ-OAHLLOKOSA-N 0.000 claims description 2
• NPTVMHJDXVMZHX-QGZVFWFLSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 NPTVMHJDXVMZHX-QGZVFWFLSA-N 0.000 claims description 2
• NHPRUKCTQGSCTM-FSRHSHDFSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(4-propylsulfonylphenyl)phenyl]-1,3-oxazole;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)CCC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3[C@@H](CCC3)C)N=2)C=C1 NHPRUKCTQGSCTM-FSRHSHDFSA-N 0.000 claims description 2
• ABLWSQRTMVJWAY-GGMCWBHBSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(6-methylsulfonylpyridin-3-yl)phenyl]-1,3-oxazole;dihydrochloride Chemical compound Cl.Cl.C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=NC(=CC=2)S(C)(=O)=O)=N1 ABLWSQRTMVJWAY-GGMCWBHBSA-N 0.000 claims description 2
• HHSPIRKBHIBMSL-QGZVFWFLSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(pyridin-3-ylmethoxy)phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3C=NC=CC=3)=CC=2)=N1 HHSPIRKBHIBMSL-QGZVFWFLSA-N 0.000 claims description 2
• WZOGAPGBVMKUKZ-OAHLLOKOSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3N=C(C)SC=3)=CC=2)=N1 WZOGAPGBVMKUKZ-OAHLLOKOSA-N 0.000 claims description 2
• NBFXEIQVASHVEU-GOSISDBHSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-[(4-methylsulfonylphenyl)methoxy]phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(OCC=3C=CC(=CC=3)S(C)(=O)=O)=CC=2)=N1 NBFXEIQVASHVEU-GOSISDBHSA-N 0.000 claims description 2
• JBSQWUZEJWANSO-MRXNPFEDSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[6-(4-methylsulfonylphenyl)pyridin-3-yl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=NC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 JBSQWUZEJWANSO-MRXNPFEDSA-N 0.000 claims description 2
• WCTDJSQNKDVHDS-GMUIIQOCSA-N 5-methyl-4-[3-[(2r)-2-methylpyrrolidin-1-yl]propyl]-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole;hydrochloride Chemical compound Cl.C[C@@H]1CCCN1CCCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 WCTDJSQNKDVHDS-GMUIIQOCSA-N 0.000 claims description 2
• SKNSIHRWFRPKRR-QGZVFWFLSA-N C[C@@H]1C=CC=CN1CCC2=C(OC(=N2)C3=CC=C(C=C3)C4=CC(=CN=C4)OC)C Chemical compound C[C@@H]1C=CC=CN1CCC2=C(OC(=N2)C3=CC=C(C=C3)C4=CC(=CN=C4)OC)C SKNSIHRWFRPKRR-QGZVFWFLSA-N 0.000 claims description 2
• SPSUEZIBYFWSDE-MRXNPFEDSA-N C[C@@H]1C=CC=CN1CCC2=C(OC(=N2)C3=CC=C(C=C3)C4=CC=C(S4)C#N)C Chemical compound C[C@@H]1C=CC=CN1CCC2=C(OC(=N2)C3=CC=C(C=C3)C4=CC=C(S4)C#N)C SPSUEZIBYFWSDE-MRXNPFEDSA-N 0.000 claims description 2
• MJMKWIAEKGMVJI-MRXNPFEDSA-N C[C@@H]1C=CC=CN1CCC2=C(OC(=N2)C3=CC=C(C=C3)C4=CN=C(N=C4)OC)C Chemical compound C[C@@H]1C=CC=CN1CCC2=C(OC(=N2)C3=CC=C(C=C3)C4=CN=C(N=C4)OC)C MJMKWIAEKGMVJI-MRXNPFEDSA-N 0.000 claims description 2
• PPYAVVTXWQZAFM-VEIFNGETSA-N acetic acid;(3r)-1-[2-[5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazol-4-yl]ethyl]pyrrolidin-3-ol Chemical compound CC(O)=O.CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCN1CC[C@@H](O)C1 PPYAVVTXWQZAFM-VEIFNGETSA-N 0.000 claims description 2
• PPYAVVTXWQZAFM-BDQAORGHSA-N acetic acid;(3s)-1-[2-[5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazol-4-yl]ethyl]pyrrolidin-3-ol Chemical compound CC(O)=O.CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCN1CC[C@H](O)C1 PPYAVVTXWQZAFM-BDQAORGHSA-N 0.000 claims description 2
• FUDOKVXVYFIBLV-UHFFFAOYSA-N n,n-diethyl-2-[5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazol-4-yl]ethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O1C(C)=C(CCN(CC)CC)N=C1C1=CC=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=C1 FUDOKVXVYFIBLV-UHFFFAOYSA-N 0.000 claims description 2
• ZJNQBNRQBMIDRV-UHFFFAOYSA-N n,n-dimethyl-4-[4-[5-methyl-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazol-2-yl]phenyl]benzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3CCCC3)N=2)C=C1 ZJNQBNRQBMIDRV-UHFFFAOYSA-N 0.000 claims description 2
• GZQJZQVUKKFHRI-GOSISDBHSA-N n,n-dimethyl-4-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]benzamide Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(=O)N(C)C)=N1 GZQJZQVUKKFHRI-GOSISDBHSA-N 0.000 claims description 2
• MAXVAOVNYGOSHK-GOSISDBHSA-N n,n-dimethyl-4-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]benzenesulfonamide Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(=O)(=O)N(C)C)=N1 MAXVAOVNYGOSHK-GOSISDBHSA-N 0.000 claims description 2
• PQMYKMKNBXYJMC-UHFFFAOYSA-N n-[4-[4-[4-(pyrrolidin-1-ylmethyl)-1,3-oxazol-2-yl]phenyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CC=C(C=2OC=C(CN3CCCC3)N=2)C=C1 PQMYKMKNBXYJMC-UHFFFAOYSA-N 0.000 claims description 2
• UKMGDAXQGDWNFX-QGZVFWFLSA-N 1-[2-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]phenyl]ethanone Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C(=CC=CC=2)C(C)=O)=N1 UKMGDAXQGDWNFX-QGZVFWFLSA-N 0.000 claims 1
• FDOQRWMEYSYWTB-QGZVFWFLSA-N 1-[4-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]phenyl]ethanone Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(C)=O)=N1 FDOQRWMEYSYWTB-QGZVFWFLSA-N 0.000 claims 1
• FKIPGJJJXXKEFZ-UTONKHPSSA-N 2-(4-bromophenyl)-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole;hydrochloride Chemical compound Cl.C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(Br)=CC=2)=N1 FKIPGJJJXXKEFZ-UTONKHPSSA-N 0.000 claims 1
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