AU2005275183B2 - Oxazole derivatives as histamine H3 receptor agents, preparation and therapeutic uses - Google Patents

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Publication number

AU2005275183B2

AU2005275183B2 AU2005275183A AU2005275183A AU2005275183B2 AU 2005275183 B2 AU2005275183 B2 AU 2005275183B2 AU 2005275183 A AU2005275183 A AU 2005275183A AU 2005275183 A AU2005275183 A AU 2005275183A AU 2005275183 B2 AU2005275183 B2 AU 2005275183B2

Authority

AU

Australia

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 102000004384 Histamine H3 receptors Human genes 0.000 title abstract description 48
• 108090000981 Histamine H3 receptors Proteins 0.000 title abstract description 48
• 238000002360 preparation method Methods 0.000 title description 10
• 230000001225 therapeutic effect Effects 0.000 title description 5
• 150000007978 oxazole derivatives Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 347
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 299
• 238000000034 method Methods 0.000 claims abstract description 202
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 200
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 167
• 150000002367 halogens Chemical class 0.000 claims abstract description 131
• 150000003839 salts Chemical class 0.000 claims abstract description 102
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 97
• -1 aryl oxazole compounds Chemical class 0.000 claims abstract description 71
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 55
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 55
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
• 239000001257 hydrogen Substances 0.000 claims abstract description 45
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 33
• 125000001424 substituent group Chemical group 0.000 claims abstract description 33
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 28
• 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 105
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 91
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 88
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 25
• 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 24
• 125000004429 atom Chemical group 0.000 claims description 22
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
• 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 19
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 208000012902 Nervous system disease Diseases 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 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 9
• 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 8
• 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 7
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 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
• 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 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
• 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 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 5
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 239000011593 sulfur Substances 0.000 claims description 4
• GIQQAQFTVJTULV-UHFFFAOYSA-N 1,3-oxazol-3-ium;chloride Chemical compound Cl.C1=COC=N1 GIQQAQFTVJTULV-UHFFFAOYSA-N 0.000 claims description 3
• XSELYVQZWYAQLM-GMUIIQOCSA-N 2-[4-(4-ethylsulfonylphenyl)phenyl]-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)CC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3[C@@H](CCC3)C)N=2)C=C1 XSELYVQZWYAQLM-GMUIIQOCSA-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
• ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 2-methyl-1,3-oxazole Chemical compound CC1=NC=CO1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 claims description 3
• IPSCBVAZSNWCIS-OAHLLOKOSA-N 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=COC(C=2C=CC(OCC=3N=CSC=3)=CC=2)=N1 IPSCBVAZSNWCIS-OAHLLOKOSA-N 0.000 claims description 3
• GXDISHAMZOCVSX-FQEVSTJZSA-N 4-[2-[(3s)-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-FQEVSTJZSA-N 0.000 claims description 3
• IKNWNMXEPYRLJE-MRXNPFEDSA-N 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(N)=O)=N1 IKNWNMXEPYRLJE-MRXNPFEDSA-N 0.000 claims description 3
• ZYMHCFYHVYGFMS-UHFFFAOYSA-N 5-methyl-1,3-oxazole Chemical compound CC1=CN=CO1 ZYMHCFYHVYGFMS-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
• 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 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
• 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
• 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 3
• 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 3
• 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 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
• 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 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
• NOKFFGOYUXGLGL-PKLMIRHRSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-[4-(trifluoromethylsulfonyl)phenyl]phenyl]-1,3-oxazole;hydrochloride Chemical compound Cl.C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(=O)(=O)C(F)(F)F)=N1 NOKFFGOYUXGLGL-PKLMIRHRSA-N 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 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 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
• YKWGPUBBILELJJ-UHFFFAOYSA-N n-methyl-n-[2-[5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazol-4-yl]ethyl]propan-2-amine;hydrochloride Chemical compound Cl.O1C(C)=C(CCN(C)C(C)C)N=C1C1=CC=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=C1 YKWGPUBBILELJJ-UHFFFAOYSA-N 0.000 claims description 3
• 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
• 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 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
• 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 2
• 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 2
• 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 2
• 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 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
• YIEJQHRNDDAGRW-VZYDHVRKSA-N 4-[2-[(2r)-2-ethylpyrrolidin-1-yl]ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole;hydrochloride Chemical compound Cl.CC[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 YIEJQHRNDDAGRW-VZYDHVRKSA-N 0.000 claims description 2
• UVPLDYVDMYQOPT-QGZVFWFLSA-N 4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(pyridin-2-ylmethoxy)phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=COC(C=2C=CC(OCC=3N=CC=CC=3)=CC=2)=N1 UVPLDYVDMYQOPT-QGZVFWFLSA-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
• GQWOBHHKZDPHHZ-QGZVFWFLSA-N 4-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C#N)=N1 GQWOBHHKZDPHHZ-QGZVFWFLSA-N 0.000 claims description 2
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