JP2013545744A5 - - Google Patents
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- Publication number
- JP2013545744A5 JP2013545744A5 JP2013538312A JP2013538312A JP2013545744A5 JP 2013545744 A5 JP2013545744 A5 JP 2013545744A5 JP 2013538312 A JP2013538312 A JP 2013538312A JP 2013538312 A JP2013538312 A JP 2013538312A JP 2013545744 A5 JP2013545744 A5 JP 2013545744A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethoxyphenyl
- benzyl
- methyl
- piperidin
- pyrrolidin
- 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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- 125000001424 substituent group Chemical group 0.000 claims 31
- -1 phenyloxy Chemical group 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 229910052736 halogen Chemical group 0.000 claims 20
- 150000002367 halogens Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 13
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 12
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000001624 naphthyl group Chemical group 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000035622 drinking Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000007937 eating Effects 0.000 claims 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 230000003340 mental effect Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- ADMREWYBXXZUMI-LJQANCHMSA-N (6r)-6-(2,6-dimethoxyphenyl)-1-(quinolin-2-ylmethyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1[C@@H]1N(CC=2N=C3C=CC=CC3=CC=2)C(=O)CCC1 ADMREWYBXXZUMI-LJQANCHMSA-N 0.000 claims 1
- OCTOQPZKGOMKKM-UHFFFAOYSA-N 1-(1-benzofuran-2-ylmethyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2OC3=CC=CC=C3C=2)C(=O)CCC1 OCTOQPZKGOMKKM-UHFFFAOYSA-N 0.000 claims 1
- OICORZNDSGZRFF-UHFFFAOYSA-N 1-(1-benzothiophen-5-ylmethyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3C=CSC3=CC=2)C(=O)CCC1 OICORZNDSGZRFF-UHFFFAOYSA-N 0.000 claims 1
- XUPSRCQFRXDXIL-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-3,3-difluoro-5-(2-fluoro-6-methoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC=CC(F)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)C(F)(F)C1 XUPSRCQFRXDXIL-UHFFFAOYSA-N 0.000 claims 1
- KZHOUIVIZGUISG-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-5-(2,4-dimethoxypyridin-3-yl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=NC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)C(C)C1 KZHOUIVIZGUISG-UHFFFAOYSA-N 0.000 claims 1
- YEGSYMNMIHXAMS-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-5-(2,6-dimethoxyphenyl)-3,3-difluoropyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)C(F)(F)C1 YEGSYMNMIHXAMS-UHFFFAOYSA-N 0.000 claims 1
- PEAXRVOYMYUBCP-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-5-(2,6-dimethoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)C(C)C1 PEAXRVOYMYUBCP-UHFFFAOYSA-N 0.000 claims 1
- FHPANOIZEGWXAC-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)CC1 FHPANOIZEGWXAC-UHFFFAOYSA-N 0.000 claims 1
- XJZTXMOXMDLNSA-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-5-(2-ethoxy-6-fluorophenyl)-3-methylpyrrolidin-2-one Chemical compound CCOC1=CC=CC(F)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)C(C)C1 XJZTXMOXMDLNSA-UHFFFAOYSA-N 0.000 claims 1
- NZJJLLAOHLKKIZ-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-5-(2-fluoro-6-methoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(F)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)C(C)C1 NZJJLLAOHLKKIZ-UHFFFAOYSA-N 0.000 claims 1
- JVILZWKBBUPTPP-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-6-(2,4-dimethoxypyridin-3-yl)piperidin-2-one Chemical compound COC1=CC=NC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)CCC1 JVILZWKBBUPTPP-UHFFFAOYSA-N 0.000 claims 1
- ALXXSSTULXRROK-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)CCC1 ALXXSSTULXRROK-UHFFFAOYSA-N 0.000 claims 1
- RZIWRUCHHJWXCX-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-6-(3,5-dimethoxypyridin-4-yl)piperidin-2-one Chemical compound COC1=CN=CC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)CCC1 RZIWRUCHHJWXCX-UHFFFAOYSA-N 0.000 claims 1
- PLSLMYBUUIRIHB-UHFFFAOYSA-N 1-(dibenzofuran-2-ylmethyl)-7-(2,6-dimethoxyphenyl)azepan-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4OC3=CC=2)C(=O)CCCC1 PLSLMYBUUIRIHB-UHFFFAOYSA-N 0.000 claims 1
- SXJVXFFSXZNQAN-UHFFFAOYSA-N 1-(dibenzothiophen-2-ylmethyl)-5-(2,6-dimethoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3C4=CC=CC=C4SC3=CC=2)C(=O)C(C)C1 SXJVXFFSXZNQAN-UHFFFAOYSA-N 0.000 claims 1
- ZVAPJUVMCPUKOM-UHFFFAOYSA-N 1-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3OC(F)(F)OC3=CC=2)C(=O)CCC1 ZVAPJUVMCPUKOM-UHFFFAOYSA-N 0.000 claims 1
- ZCYAKVORBGSGNZ-UHFFFAOYSA-N 1-[(2-chloro-5-pyridin-2-ylphenyl)methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C(=CC=C(C=2)C=2N=CC=CC=2)Cl)C(=O)CCC1 ZCYAKVORBGSGNZ-UHFFFAOYSA-N 0.000 claims 1
- ZJYAAFGKMJOGRF-UHFFFAOYSA-N 1-[(3-chloro-5-pyridin-2-ylphenyl)methyl]-5-(2,6-dimethoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(C=C(Cl)C=2)C=2N=CC=CC=2)C(=O)C(C)C1 ZJYAAFGKMJOGRF-UHFFFAOYSA-N 0.000 claims 1
- YOXFIJCSNYXNHO-UHFFFAOYSA-N 1-[(3-chloro-5-pyridin-2-ylphenyl)methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(C=C(Cl)C=2)C=2N=CC=CC=2)C(=O)CCC1 YOXFIJCSNYXNHO-UHFFFAOYSA-N 0.000 claims 1
- MNPWTNLMGSASDH-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=CC(Cl)=CC=2)C(=O)CCC1 MNPWTNLMGSASDH-UHFFFAOYSA-N 0.000 claims 1
- HMIGQZCCCBMNIM-UHFFFAOYSA-N 1-[1-[5-chloro-6-(difluoromethoxy)pyridin-3-yl]ethyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(C(C)C=2C=C(Cl)C(OC(F)F)=NC=2)C(=O)CCC1 HMIGQZCCCBMNIM-UHFFFAOYSA-N 0.000 claims 1
- KYSCRMHLIVJYBV-UHFFFAOYSA-N 1-[[3-(2,2-difluoroethoxy)phenyl]methyl]-5-(2,6-dimethoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(OCC(F)F)C=CC=2)C(=O)C(C)C1 KYSCRMHLIVJYBV-UHFFFAOYSA-N 0.000 claims 1
- AEGWGVROKVYKOO-UHFFFAOYSA-N 1-[[3-(2-methyl-1,3-thiazol-4-yl)phenyl]methyl]-5-(2-phenylphenyl)pyrrolidin-2-one Chemical compound S1C(C)=NC(C=2C=C(CN3C(CCC3C=3C(=CC=CC=3)C=3C=CC=CC=3)=O)C=CC=2)=C1 AEGWGVROKVYKOO-UHFFFAOYSA-N 0.000 claims 1
- APJABJVOEWIGOA-UHFFFAOYSA-N 1-[[3-(4-chloro-1,3-thiazol-2-yl)phenyl]methyl]-5-(2,4-dimethoxypyridin-3-yl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=NC(OC)=C1C1N(CC=2C=C(C=CC=2)C=2SC=C(Cl)N=2)C(=O)C(C)C1 APJABJVOEWIGOA-UHFFFAOYSA-N 0.000 claims 1
- WRGYINVCPYAEMS-UHFFFAOYSA-N 1-[[3-(4-chloro-1,3-thiazol-2-yl)phenyl]methyl]-5-(2-ethoxy-6-fluorophenyl)-3-methylpyrrolidin-2-one Chemical compound CCOC1=CC=CC(F)=C1C1N(CC=2C=C(C=CC=2)C=2SC=C(Cl)N=2)C(=O)C(C)C1 WRGYINVCPYAEMS-UHFFFAOYSA-N 0.000 claims 1
- XLRJGGDGKILWEN-UHFFFAOYSA-N 1-[[3-(4-chloro-1,3-thiazol-2-yl)phenyl]methyl]-5-(2-fluoro-6-methoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(F)=C1C1N(CC=2C=C(C=CC=2)C=2SC=C(Cl)N=2)C(=O)C(C)C1 XLRJGGDGKILWEN-UHFFFAOYSA-N 0.000 claims 1
- KVUGNCAMECQIRX-UHFFFAOYSA-N 1-[[3-(difluoromethoxy)phenyl]methyl]-5-(2,6-dimethoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(OC(F)F)C=CC=2)C(=O)C(C)C1 KVUGNCAMECQIRX-UHFFFAOYSA-N 0.000 claims 1
- QBJBEALOLFIXNB-UHFFFAOYSA-N 1-[[3-(difluoromethoxy)phenyl]methyl]-5-(2-ethoxy-6-fluorophenyl)-3-methylpyrrolidin-2-one Chemical compound CCOC1=CC=CC(F)=C1C1N(CC=2C=C(OC(F)F)C=CC=2)C(=O)C(C)C1 QBJBEALOLFIXNB-UHFFFAOYSA-N 0.000 claims 1
- NARHBIYXYMDLPF-UHFFFAOYSA-N 1-[[3-(difluoromethoxy)phenyl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(OC(F)F)C=CC=2)C(=O)CCC1 NARHBIYXYMDLPF-UHFFFAOYSA-N 0.000 claims 1
- GFQGXIOHOSSFLL-UHFFFAOYSA-N 1-[[3-chloro-4-(difluoromethoxy)phenyl]methyl]-5-(2,6-dimethoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(Cl)C(OC(F)F)=CC=2)C(=O)C(C)C1 GFQGXIOHOSSFLL-UHFFFAOYSA-N 0.000 claims 1
- VYCRLUGMYIJYFL-UHFFFAOYSA-N 1-[[3-chloro-4-(difluoromethoxy)phenyl]methyl]-5-(2-ethoxy-6-fluorophenyl)-3-methylpyrrolidin-2-one Chemical compound CCOC1=CC=CC(F)=C1C1N(CC=2C=C(Cl)C(OC(F)F)=CC=2)C(=O)C(C)C1 VYCRLUGMYIJYFL-UHFFFAOYSA-N 0.000 claims 1
- GOCCLYIBTKETEE-UHFFFAOYSA-N 1-[[3-chloro-4-(trifluoromethoxy)phenyl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(Cl)C(OC(F)(F)F)=CC=2)C(=O)CCC1 GOCCLYIBTKETEE-UHFFFAOYSA-N 0.000 claims 1
- SFFPOJXQDRAKDL-UHFFFAOYSA-N 1-[[4-(cyclopropylmethoxy)phenyl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=CC(OCC3CC3)=CC=2)C(=O)CCC1 SFFPOJXQDRAKDL-UHFFFAOYSA-N 0.000 claims 1
- GBDLXRCWLRAXEF-UHFFFAOYSA-N 1-[[4-(difluoromethoxy)phenyl]methyl]-5-(2-ethoxy-6-fluorophenyl)-3-methylpyrrolidin-2-one Chemical compound CCOC1=CC=CC(F)=C1C1N(CC=2C=CC(OC(F)F)=CC=2)C(=O)C(C)C1 GBDLXRCWLRAXEF-UHFFFAOYSA-N 0.000 claims 1
- QJXPQQXXQSQUCE-UHFFFAOYSA-N 1-[[4-(difluoromethoxy)phenyl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=CC(OC(F)F)=CC=2)C(=O)CCC1 QJXPQQXXQSQUCE-UHFFFAOYSA-N 0.000 claims 1
- HJECQBRQQKEBMC-UHFFFAOYSA-N 1-[[4-(trifluoromethoxy)phenyl]methyl]-6-(2,4,6-trimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC(OC)=CC(OC)=C1C1N(CC=2C=CC(OC(F)(F)F)=CC=2)C(=O)CCC1 HJECQBRQQKEBMC-UHFFFAOYSA-N 0.000 claims 1
- WPGULJUSTHLMDZ-UHFFFAOYSA-N 1-[[5-(difluoromethoxy)pyridin-2-yl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2N=CC(OC(F)F)=CC=2)C(=O)CCC1 WPGULJUSTHLMDZ-UHFFFAOYSA-N 0.000 claims 1
- OMGGLDITIJYJNZ-UHFFFAOYSA-N 1-[[5-chloro-6-(difluoromethoxy)pyridin-3-yl]methyl]-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(Cl)C(OC(F)F)=NC=2)C(=O)CC1 OMGGLDITIJYJNZ-UHFFFAOYSA-N 0.000 claims 1
- CKHQMMOXQOHIAU-UHFFFAOYSA-N 1-[[5-chloro-6-(difluoromethoxy)pyridin-3-yl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(Cl)C(OC(F)F)=NC=2)C(=O)CCC1 CKHQMMOXQOHIAU-UHFFFAOYSA-N 0.000 claims 1
- OWJWDXDGABGHJK-UHFFFAOYSA-N 1-[[5-chloro-6-(difluoromethoxy)pyridin-3-yl]methyl]-7-(2,6-dimethoxyphenyl)azepan-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(Cl)C(OC(F)F)=NC=2)C(=O)CCCC1 OWJWDXDGABGHJK-UHFFFAOYSA-N 0.000 claims 1
- MGVQTTHWUSUJOE-UHFFFAOYSA-N 1-[[6-(difluoromethoxy)-5-methylpyridin-3-yl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C(C)C(OC(F)F)=NC=2)C(=O)CCC1 MGVQTTHWUSUJOE-UHFFFAOYSA-N 0.000 claims 1
- NDWXKTBZXNLPRE-UHFFFAOYSA-N 1-[[6-(difluoromethoxy)pyridin-2-yl]methyl]-5-(2,6-dimethoxyphenyl)-3-methylpyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2N=C(OC(F)F)C=CC=2)C(=O)C(C)C1 NDWXKTBZXNLPRE-UHFFFAOYSA-N 0.000 claims 1
- BJBDGZHJEUJUCL-UHFFFAOYSA-N 1-[[6-(difluoromethoxy)pyridin-2-yl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2N=C(OC(F)F)C=CC=2)C(=O)CCC1 BJBDGZHJEUJUCL-UHFFFAOYSA-N 0.000 claims 1
- HRONCCUMYAESTQ-UHFFFAOYSA-N 1-[[6-(difluoromethoxy)pyridin-3-yl]methyl]-6-(2,6-dimethoxyphenyl)piperidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=NC(OC(F)F)=CC=2)C(=O)CCC1 HRONCCUMYAESTQ-UHFFFAOYSA-N 0.000 claims 1
- ZRGQRLBJMGIDRE-UHFFFAOYSA-N 3,3-difluoro-5-(2-fluoro-6-propan-2-yloxyphenyl)-1-[[4-(trifluoromethoxy)phenyl]methyl]pyrrolidin-2-one Chemical compound CC(C)OC1=CC=CC(F)=C1C1N(CC=2C=CC(OC(F)(F)F)=CC=2)C(=O)C(F)(F)C1 ZRGQRLBJMGIDRE-UHFFFAOYSA-N 0.000 claims 1
- UPZMCGJCIWXNRH-UHFFFAOYSA-N 3-methyl-1-[[3-(2-methyl-1,3-thiazol-4-yl)phenyl]methyl]-5-(2-phenylphenyl)pyrrolidin-2-one Chemical compound O=C1C(C)CC(C=2C(=CC=CC=2)C=2C=CC=CC=2)N1CC(C=1)=CC=CC=1C1=CSC(C)=N1 UPZMCGJCIWXNRH-UHFFFAOYSA-N 0.000 claims 1
- ZEBODEPVZIPGLD-UHFFFAOYSA-N 5-(2,4-dimethoxypyridin-3-yl)-3-methyl-1-[(3-phenylphenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=NC(OC)=C1C1N(CC=2C=C(C=CC=2)C=2C=CC=CC=2)C(=O)C(C)C1 ZEBODEPVZIPGLD-UHFFFAOYSA-N 0.000 claims 1
- JXRMUCFYWOMUCA-UHFFFAOYSA-N 5-(2,4-dimethoxypyridin-3-yl)-3-methyl-1-[[2-(4-methylphenyl)-1,3-thiazol-4-yl]methyl]pyrrolidin-2-one Chemical compound COC1=CC=NC(OC)=C1C1N(CC=2N=C(SC=2)C=2C=CC(C)=CC=2)C(=O)C(C)C1 JXRMUCFYWOMUCA-UHFFFAOYSA-N 0.000 claims 1
- RRXDXVXPVJIGDF-UHFFFAOYSA-N 5-(2,4-dimethoxypyridin-3-yl)-3-methyl-1-[[3-(2-methyl-1,3-thiazol-4-yl)phenyl]methyl]pyrrolidin-2-one Chemical compound COC1=CC=NC(OC)=C1C1N(CC=2C=C(C=CC=2)C=2N=C(C)SC=2)C(=O)C(C)C1 RRXDXVXPVJIGDF-UHFFFAOYSA-N 0.000 claims 1
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- LLSMZDUNJOKSBC-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-1-(naphthalen-2-ylmethyl)pyrrolidin-2-one Chemical compound COC1=CC=CC(OC)=C1C1N(CC=2C=C3C=CC=CC3=CC=2)C(=O)CC1 LLSMZDUNJOKSBC-UHFFFAOYSA-N 0.000 claims 1
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| US9611267B2 (en) | 2012-06-13 | 2017-04-04 | Incyte Holdings Corporation | Substituted tricyclic compounds as FGFR inhibitors |
| US9440919B2 (en) * | 2012-07-19 | 2016-09-13 | Cayman Chemical Company, Inc. | Difluorolactam compositions for EP4-mediated osteo related diseases and conditions |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US8987461B2 (en) | 2012-12-06 | 2015-03-24 | Quanticel Pharmaceuticals, Inc. | Histone demethylase inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| ES2635635T3 (es) | 2013-03-15 | 2017-10-04 | Cayman Chemical Company, Incorporated | Compuestos de difluorolactama como agonistas selectivos del receptor EP4 para su uso en el tratamiento de enfermedades y afecciones mediadas por EP4 |
| WO2014144610A1 (en) | 2013-03-15 | 2014-09-18 | Cayman Chemical Company, Inc. | Lactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated diseases and conditions |
| JP6368351B2 (ja) | 2013-03-15 | 2018-08-01 | ケイマン ケミカル カンパニー， インコーポレーテッド | ジフルオロラクタムアナログを合成する方法 |
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| CN104133004A (zh) * | 2013-05-03 | 2014-11-05 | 上海美迪西生物医药有限公司 | 血浆样品中2,3-吲哚醌的浓度的测定方法 |
| EP3021879A2 (en) | 2013-07-19 | 2016-05-25 | Cayman Chemical Company, Incorporated | Methods, systems, and compositions for promoting bone growth |
| UA119151C2 (uk) | 2013-12-03 | 2019-05-10 | Ідорсія Фармасьютікалз Лтд | КРИСТАЛІЧНА СОЛЬОВА ФОРМА (S)-(2-(6-ХЛОР-7-МЕТИЛ-1H-БЕНЗО[d]ІМІДАЗОЛ-2-ІЛ)-2-МЕТИЛПІРОЛІДИН-1-ІЛ)(5-МЕТОКСИ-2-(2H-1,2,3-ТРИАЗОЛ-2-ІЛ)ФЕНІЛ)МЕТАНОНУ ЯК АНТАГОНІСТ ОРЕКСИНОВОГО РЕЦЕПТОРА |
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| UA116053C2 (uk) | 2013-12-04 | 2018-01-25 | Ідорсія Фармасьютікалз Лтд | Застосування похідних бензоімідазолу-проліну |
| US9975876B2 (en) | 2013-12-09 | 2018-05-22 | Merck Sharp & Dohme Corp. | 2-pyridyloxy-3-ester-4-ether orexin receptor antagonists |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| AU2016219822B2 (en) | 2015-02-20 | 2020-07-09 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2016134294A1 (en) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Bicyclic heterocycles as fgfr4 inhibitors |
| US11332470B2 (en) * | 2016-06-21 | 2022-05-17 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
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| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| TWI799435B (zh) * | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | 製備化合物之製程 |
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| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| GEAP202415945A (en) | 2019-10-14 | 2024-04-25 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CA3163875A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| AU2020395185A1 (en) | 2019-12-04 | 2022-06-02 | Incyte Corporation | Derivatives of an FGFR inhibitor |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
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| AR126101A1 (es) | 2021-06-09 | 2023-09-13 | Incyte Corp | Heterociclos tricíclicos como inhibidores de fgfr |
| CA3220274A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| CN114456184B (zh) * | 2022-02-21 | 2023-08-22 | 南华大学附属第一医院 | 一种3-芳基异喹啉衍生物及其制备与应用 |
| CN115047127B (zh) * | 2022-04-25 | 2024-03-08 | 中国检验检疫科学研究院 | 一种利用挥发性代谢组学技术鉴别nfc和fc橙汁的方法 |
| TW202409023A (zh) | 2022-07-14 | 2024-03-01 | 美商富曼西公司 | 除草苯并𠯤 |
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| EA201070091A1 (ru) * | 2007-07-03 | 2010-06-30 | Глэксо Груп Лимитед | Производные пиперидина, пригодные в качестве антагонистов рецептора орексина |
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2011
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- 2011-11-09 WO PCT/IB2011/054993 patent/WO2012063207A1/en not_active Ceased
- 2011-11-09 EP EP11820868.5A patent/EP2638008B1/en not_active Not-in-force
- 2011-11-09 US US13/884,741 patent/US9242970B2/en not_active Expired - Fee Related
- 2011-11-09 JP JP2013538312A patent/JP5847830B2/ja not_active Expired - Fee Related
- 2011-11-09 CN CN2011800543642A patent/CN103201261A/zh active Pending
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