JP2008507579A5 - - Google Patents
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- Publication number
- JP2008507579A5 JP2008507579A5 JP2007523605A JP2007523605A JP2008507579A5 JP 2008507579 A5 JP2008507579 A5 JP 2008507579A5 JP 2007523605 A JP2007523605 A JP 2007523605A JP 2007523605 A JP2007523605 A JP 2007523605A JP 2008507579 A5 JP2008507579 A5 JP 2008507579A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethyl
- pyrrolidin
- oxazol
- oxazole
- Prior art date
- 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.)
- Granted
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 46
- 229910052757 nitrogen Inorganic materials 0.000 claims 33
- 229910052736 halogen Inorganic materials 0.000 claims 31
- 150000002367 halogens Chemical class 0.000 claims 25
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- -1 2-pyrrolidin-1-yl-ethyl Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 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 2
- 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 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 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
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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 1
- YTEPWBKLXXBZAR-UHFFFAOYSA-N 2-(4-pyridin-3-ylphenyl)-4-(pyrrolidin-1-ylmethyl)-1,3-oxazole;dihydrochloride Chemical compound Cl.Cl.C=1OC(C=2C=CC(=CC=2)C=2C=NC=CC=2)=NC=1CN1CCCC1 YTEPWBKLXXBZAR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- CCEAOOHQTODKST-MRXNPFEDSA-N 2-[4-(2-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(=CC=CC=2)F)=N1 CCEAOOHQTODKST-MRXNPFEDSA-N 0.000 claims 1
- NNSHKBZLTXUPBU-QGZVFWFLSA-N 2-[4-(2-methoxyphenyl)phenyl]-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole Chemical compound COC1=CC=CC=C1C1=CC=C(C=2OC(C)=C(CCN3[C@@H](CCC3)C)N=2)C=C1 NNSHKBZLTXUPBU-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- CFRSXYCHPAJCHX-QGZVFWFLSA-N 2-[4-(3-methoxyphenyl)phenyl]-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)C=2OC(C)=C(CCN3[C@@H](CCC3)C)N=2)=C1 CFRSXYCHPAJCHX-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- 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 1
- HSTWPBMRMHMRHW-MRXNPFEDSA-N 2-[4-(4-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=CC(F)=CC=2)=N1 HSTWPBMRMHMRHW-MRXNPFEDSA-N 0.000 claims 1
- 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 1
- PTUQHBAVGDWUKV-QGZVFWFLSA-N 2-[4-(4-methoxyphenyl)phenyl]-5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2OC(C)=C(CCN3[C@@H](CCC3)C)N=2)C=C1 PTUQHBAVGDWUKV-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- GPRVNFVEHMEBHC-FSRHSHDFSA-N 2-[4-[4-(3-fluoropropylsulfonyl)phenyl]phenyl]-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(=CC=2)C=2C=CC(=CC=2)S(=O)(=O)CCCF)=N1 GPRVNFVEHMEBHC-FSRHSHDFSA-N 0.000 claims 1
- 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 1
- 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 1
- USZQOHBPCSRMNJ-QGZVFWFLSA-N 3-[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=C(C=CC=2)C#N)=N1 USZQOHBPCSRMNJ-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- GRRYKJCMFQEMQQ-UHFFFAOYSA-N 4-[2-(azetidin-1-yl)ethyl]-5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole;hydrochloride Chemical compound Cl.CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCN1CCC1 GRRYKJCMFQEMQQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- QBANDWBINHAYDC-QGZVFWFLSA-N 4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=COC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 QBANDWBINHAYDC-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 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 1
- 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 1
- 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 1
- ZSWBHEQVJCJPMN-UHFFFAOYSA-N 5-methyl-2-(4-pyridin-3-ylphenyl)-4-(2-pyrrolidin-1-ylethyl)-1,3-oxazole;dihydrochloride Chemical compound Cl.Cl.CC=1OC(C=2C=CC(=CC=2)C=2C=NC=CC=2)=NC=1CCN1CCCC1 ZSWBHEQVJCJPMN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- AQFZONRPZKBOCN-UHFFFAOYSA-N 5-methyl-2-[4-(4-methylsulfonylphenyl)phenyl]-4-(3-pyrrolidin-1-ylpropyl)-1,3-oxazole;hydrochloride Chemical compound Cl.CC=1OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1CCCN1CCCC1 AQFZONRPZKBOCN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- DCNPTBRUXDRELW-QGZVFWFLSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-(4-phenylphenyl)-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 DCNPTBRUXDRELW-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- CIVCRBZMDZVZTM-GGMCWBHBSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-(4-pyridin-3-ylphenyl)-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)=N1 CIVCRBZMDZVZTM-GGMCWBHBSA-N 0.000 claims 1
- AZWJUIUGPSRWDK-GGMCWBHBSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-(4-pyridin-4-ylphenyl)-1,3-oxazole;dihydrochloride Chemical compound Cl.Cl.C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=N1 AZWJUIUGPSRWDK-GGMCWBHBSA-N 0.000 claims 1
- HTSHTGLYRHGLJX-OAHLLOKOSA-N 5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2-(4-pyrimidin-5-ylphenyl)-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=NC=NC=2)=N1 HTSHTGLYRHGLJX-OAHLLOKOSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- MOLOWIWOHSMJRD-UNTBIKODSA-N [3-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]phenyl]methanol;hydrochloride Chemical compound Cl.C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=C(CO)C=CC=2)=N1 MOLOWIWOHSMJRD-UNTBIKODSA-N 0.000 claims 1
- TULMBMGLJRRRSO-HXUWFJFHSA-N [4-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(=O)N2CCCC2)=N1 TULMBMGLJRRRSO-HXUWFJFHSA-N 0.000 claims 1
- WCJRQJNOVZQMST-UNTBIKODSA-N [4-[4-[5-methyl-4-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1,3-oxazol-2-yl]phenyl]phenyl]methanol;hydrochloride Chemical compound Cl.C[C@@H]1CCCN1CCC1=C(C)OC(C=2C=CC(=CC=2)C=2C=CC(CO)=CC=2)=N1 WCJRQJNOVZQMST-UNTBIKODSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 239000003610 charcoal Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
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| PCT/US2005/024883 WO2006019833A1 (en) | 2004-07-26 | 2005-07-14 | Oxazole derivatives as histamine h3 receptor agents, preparation and therapeutic uses |
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| JP2008507579A JP2008507579A (ja) | 2008-03-13 |
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| PT (1) | PT1786790E (OSRAM) |
| SI (1) | SI1786790T1 (OSRAM) |
| WO (1) | WO2006019833A1 (OSRAM) |
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| US8008301B2 (en) * | 2004-04-01 | 2011-08-30 | Eli Lilly And Company | Histamine H3 receptor agents, preparation and therapeutic uses |
| US7728009B1 (en) | 2005-02-18 | 2010-06-01 | Neurogen Corporation | Thiazole amides, imidazole amides and related analogues |
| EP1866293A1 (en) * | 2005-03-31 | 2007-12-19 | UCB Pharma, S.A. | Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses |
| RU2418793C2 (ru) | 2005-11-15 | 2011-05-20 | Оцука Фармасьютикал Ко., Лтд. | Соединение оксазола и фармацевтическая композиция |
| BRPI0709612A2 (pt) | 2006-03-15 | 2011-07-19 | Wyeth Corp | composto de fórmula i; método para o tratamento de um distúrbio no sistema nervoso central relacionado ou afetado pelo receptor histamina-3 em um paciente que necessita deste tratamento; método para a inibição do receptor h3; composição farmacêutica; e processo para a preparação de um composto de fórmula i |
| CA2649913A1 (en) | 2006-05-19 | 2007-11-29 | Wyeth | N-benzoyl- and n-benzylpyrrolidin-3-ylamines as histamine-3 antagonists |
| US20090215628A1 (en) * | 2006-05-19 | 2009-08-27 | Basf Se | Benzoyl-Substituted Alanines |
| US8329159B2 (en) * | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| PE20081152A1 (es) | 2006-10-06 | 2008-08-10 | Wyeth Corp | Azaciclilaminas n-sustituidas como antagonistas de histamina-3 |
| US7803825B2 (en) | 2007-07-16 | 2010-09-28 | Wyeth Llc | Aminoalkylazole derivatives as histamine-3 antagonists |
| WO2009126782A1 (en) * | 2008-04-11 | 2009-10-15 | High Point Pharmaceuticals, Llc | Histamine h3 receptor ligands |
| US8383829B2 (en) * | 2008-04-15 | 2013-02-26 | Konica Minolta Holdings, Inc. | Electrochromic compound, electrode, and display element |
| SA110310332B1 (ar) * | 2009-05-01 | 2013-12-10 | Astrazeneca Ab | مركبات ميثانون (3 استبدال -ازيتيدين -1-يل )(5- فينيل -1، 3، 4- أوكساديازول -2-يل ) |
| ES2527466T3 (es) | 2010-07-06 | 2015-01-26 | Astrazeneca Ab | Agentes terapéuticos 976 |
| UY34194A (es) | 2011-07-15 | 2013-02-28 | Astrazeneca Ab | ?(3-(4-(espiroheterocíclico)metil)fenoxi)azetidin-1-il)(5-(fenil)-1,3,4-oxadiazol-2-il)metanona en el tratamiento de la obesidad? |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| EP2948447B1 (en) | 2013-01-23 | 2016-09-21 | Astrazeneca AB | Chemical compounds |
| EP3233828B1 (en) * | 2014-12-18 | 2020-03-04 | F. Hoffmann-La Roche AG | Estrogen receptor modulators and uses thereof |
| PH12017502158B1 (en) | 2015-06-03 | 2022-04-27 | Bristol Meyers Squibb Co | 4-hydroxy-3-(heteroaryl)pyridine-2-one apj agonists for use in the treatment of cardiovascular disorders |
| EP3319968A1 (en) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| PT3319959T (pt) | 2015-07-06 | 2021-12-06 | Alkermes Inc | Inibidores hetero-halo de histona desacetilase |
| CA3049443A1 (en) | 2017-01-11 | 2018-07-19 | Rodin Therapeutics, Inc. | Bicyclic inhibitors of histone deacetylase |
| JP7152471B2 (ja) | 2017-08-07 | 2022-10-12 | ロダン・セラピューティクス，インコーポレーテッド | ヒストン脱アセチル化酵素の二環阻害剤 |
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| DE3819037A1 (de) * | 1988-06-04 | 1989-12-14 | Hoechst Ag | 2,4-disubstituierte oxazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als therapiemittel gegen krankheiten, die durch rhinoviren verursacht werden |
| WO1995009159A1 (en) * | 1993-09-28 | 1995-04-06 | Otsuka Pharmaceutical Company, Limited | Quinoxaline derivative as antidiabetic agent |
| AU3957600A (en) | 1999-04-26 | 2000-11-10 | Boehringer Ingelheim International Gmbh | Piperidyl-imidazole derivatives, their preparations and therapeutic uses |
| WO2002076925A2 (en) | 2001-03-23 | 2002-10-03 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
| PL371435A1 (en) | 2002-02-01 | 2005-06-13 | Novo Nordisk A/S | Amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes |
| US7332508B2 (en) | 2002-12-18 | 2008-02-19 | Novo Nordisk A/S | Substituted homopiperidine, piperidine or pyrrolidine derivatives |
| US7259262B2 (en) * | 2003-10-24 | 2007-08-21 | Hoffmann-La Roche Inc. | Arylazole derivatives, their manufacture and use as pharmaceutical agents |
-
2005
- 2005-07-14 ES ES05773290T patent/ES2325865T3/es not_active Expired - Lifetime
- 2005-07-14 BR BRPI0513777-2A patent/BRPI0513777A/pt not_active IP Right Cessation
- 2005-07-14 SI SI200530741T patent/SI1786790T1/sl unknown
- 2005-07-14 WO PCT/US2005/024883 patent/WO2006019833A1/en not_active Ceased
- 2005-07-14 PL PL05773290T patent/PL1786790T3/pl unknown
- 2005-07-14 PT PT05773290T patent/PT1786790E/pt unknown
- 2005-07-14 DE DE602005014786T patent/DE602005014786D1/de not_active Expired - Lifetime
- 2005-07-14 MX MX2007001029A patent/MX2007001029A/es active IP Right Grant
- 2005-07-14 JP JP2007523605A patent/JP4982367B2/ja not_active Expired - Fee Related
- 2005-07-14 DK DK05773290T patent/DK1786790T3/da active
- 2005-07-14 CA CA2575081A patent/CA2575081C/en not_active Expired - Fee Related
- 2005-07-14 AU AU2005275183A patent/AU2005275183B2/en not_active Ceased
- 2005-07-14 EP EP05773290A patent/EP1786790B1/en not_active Expired - Lifetime
- 2005-07-14 AT AT05773290T patent/ATE432926T1/de active
- 2005-07-14 US US11/572,283 patent/US7666871B2/en not_active Expired - Fee Related
- 2005-07-14 CN CN200580024874XA patent/CN1989115B/zh not_active Expired - Fee Related
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2009
- 2009-08-06 CY CY20091100831T patent/CY1109493T1/el unknown
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