SI2906546T1 - Benzamides - Google Patents
Benzamides Download PDFInfo
- Publication number
- SI2906546T1 SI2906546T1 SI201330967T SI201330967T SI2906546T1 SI 2906546 T1 SI2906546 T1 SI 2906546T1 SI 201330967 T SI201330967 T SI 201330967T SI 201330967 T SI201330967 T SI 201330967T SI 2906546 T1 SI2906546 T1 SI 2906546T1
- Authority
- SI
- Slovenia
- Prior art keywords
- benzamide
- trifluoromethyl
- chloro
- cyclopropyl
- propyl
- Prior art date
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 title 1
- 150000003936 benzamides Chemical class 0.000 title 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims abstract 53
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- -1 homomorpholinyl Chemical group 0.000 claims 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- GBLQZOHBPMHPDB-UHFFFAOYSA-N FC1=CC=CC(C(=O)NCC(CC2CC2)C=2C=NC(=NC=2)C(F)(F)F)=C1Cl Chemical compound FC1=CC=CC(C(=O)NCC(CC2CC2)C=2C=NC(=NC=2)C(F)(F)F)=C1Cl GBLQZOHBPMHPDB-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- SVXAGFVIOFXJNP-UHFFFAOYSA-N 2,3-dichloro-n-[2-(2-methylpyrimidin-5-yl)-3-[1-(trifluoromethyl)cyclopropyl]propyl]benzamide Chemical compound C1=NC(C)=NC=C1C(CC1(CC1)C(F)(F)F)CNC(=O)C1=CC=CC(Cl)=C1Cl SVXAGFVIOFXJNP-UHFFFAOYSA-N 0.000 claims 2
- GAXAVEJOQGMPBF-UHFFFAOYSA-N 2,3-dichloro-n-[3-[1-(trifluoromethyl)cyclopropyl]-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=NC=C1C(CC1(CC1)C(F)(F)F)CNC(=O)C1=CC=CC(Cl)=C1Cl GAXAVEJOQGMPBF-UHFFFAOYSA-N 0.000 claims 2
- RLFSQQLHZUDDNA-UHFFFAOYSA-N 2,3-dichloro-n-[3-[1-(trifluoromethyl)cyclopropyl]-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(CC1(CC1)C(F)(F)F)CNC(=O)C1=CC=CC(Cl)=C1Cl RLFSQQLHZUDDNA-UHFFFAOYSA-N 0.000 claims 2
- RHDROFHJDUDMGT-UHFFFAOYSA-N 2,3-dichloro-n-[3-cyclopropyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=NC=C1C(CC1CC1)CNC(=O)C1=CC=CC(Cl)=C1Cl RHDROFHJDUDMGT-UHFFFAOYSA-N 0.000 claims 2
- FUNGXBHNVRVIFC-UHFFFAOYSA-N 2,6-dichloro-n-[3-cyclopropyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=NC=C1C(CC1CC1)CNC(=O)C1=C(Cl)C=CC=C1Cl FUNGXBHNVRVIFC-UHFFFAOYSA-N 0.000 claims 2
- KBQRAZHZDJPPTQ-UHFFFAOYSA-N 2-chloro-3-fluoro-n-[2-(4-fluorophenyl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide Chemical compound C1=CC(F)=CC=C1C(C=1C=NC(=NC=1)C(F)(F)F)CNC(=O)C1=CC=CC(F)=C1Cl KBQRAZHZDJPPTQ-UHFFFAOYSA-N 0.000 claims 2
- RQOQZSKCNHLSMV-UHFFFAOYSA-N 2-chloro-n-[2-(2-methylpyrimidin-5-yl)-3-[1-(trifluoromethyl)cyclopropyl]propyl]benzamide Chemical compound C1=NC(C)=NC=C1C(CC1(CC1)C(F)(F)F)CNC(=O)C1=CC=CC=C1Cl RQOQZSKCNHLSMV-UHFFFAOYSA-N 0.000 claims 2
- DLDVJLNENOLKMS-UHFFFAOYSA-N 2-chloro-n-[2-(4,4-difluorocyclohexyl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]-3-fluorobenzamide Chemical compound FC1=CC=CC(C(=O)NCC(C2CCC(F)(F)CC2)C=2C=NC(=NC=2)C(F)(F)F)=C1Cl DLDVJLNENOLKMS-UHFFFAOYSA-N 0.000 claims 2
- BBABFHCUJHALBA-UHFFFAOYSA-N 2-chloro-n-[2-(4,4-difluorocyclohexyl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]-6-fluorobenzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NCC(C=1C=NC(=NC=1)C(F)(F)F)C1CCC(F)(F)CC1 BBABFHCUJHALBA-UHFFFAOYSA-N 0.000 claims 2
- QLQIKVJKFWIZSN-UHFFFAOYSA-N 2-chloro-n-[2-(4-fluorophenyl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide Chemical compound C1=CC(F)=CC=C1C(C=1C=NC(=NC=1)C(F)(F)F)CNC(=O)C1=CC=CC=C1Cl QLQIKVJKFWIZSN-UHFFFAOYSA-N 0.000 claims 2
- GRQCSOYTLVIPEY-UHFFFAOYSA-N 2-chloro-n-[3-[1-(trifluoromethyl)cyclopropyl]-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(CC1(CC1)C(F)(F)F)CNC(=O)C1=CC=CC=C1Cl GRQCSOYTLVIPEY-UHFFFAOYSA-N 0.000 claims 2
- YHIBXEVGSQICFH-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[6-(difluoromethyl)pyridin-3-yl]propyl]-3-fluorobenzamide Chemical compound C1=NC(C(F)F)=CC=C1C(CC1CC1)CNC(=O)C1=CC=CC(F)=C1Cl YHIBXEVGSQICFH-UHFFFAOYSA-N 0.000 claims 2
- KHWQIZKQWLPKRO-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(CC1CC1)CNC(=O)C1=CC=CC=C1Cl KHWQIZKQWLPKRO-UHFFFAOYSA-N 0.000 claims 2
- WJFDKOHMAALCBK-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-methyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C1CC1CC(C=1C=NC(=NC=1)C(F)(F)F)(C)CNC(=O)C1=CC=CC=C1Cl WJFDKOHMAALCBK-UHFFFAOYSA-N 0.000 claims 2
- QJWKTXVRCDNEBW-UHFFFAOYSA-N 2-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-5-methylbenzamide Chemical compound CC1=CC=C(Cl)C(C(=O)NCC2(CCOCC2)C=2C=CC(Cl)=CC=2)=C1 QJWKTXVRCDNEBW-UHFFFAOYSA-N 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- QMCVZDMPWUCYFJ-UHFFFAOYSA-N n-[3-cyclopropyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]-3-methoxy-2-methylbenzamide Chemical compound COC1=CC=CC(C(=O)NCC(CC2CC2)C=2C=NC(=NC=2)C(F)(F)F)=C1C QMCVZDMPWUCYFJ-UHFFFAOYSA-N 0.000 claims 2
- FIRILMDKPYCHCT-UHFFFAOYSA-N n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NCC(C=1C=NC(=CC=1)C(F)(F)F)CC1CC1 FIRILMDKPYCHCT-UHFFFAOYSA-N 0.000 claims 2
- DZWUVSYGHZYLJU-UHFFFAOYSA-N n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NCC(C=1C=NC(=CC=1)C(F)(F)F)CC1CC1 DZWUVSYGHZYLJU-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
- 125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 claims 1
- BTUVROTVNUMQBL-UHFFFAOYSA-N 2,3-dichloro-N-[1-[4,4-difluoro-1-(2-methylpyrimidin-5-yl)cyclohexyl]ethyl]benzamide Chemical compound ClC1=C(C(=O)NC(C)C2(CCC(CC2)(F)F)C=2C=NC(=NC2)C)C=CC=C1Cl BTUVROTVNUMQBL-UHFFFAOYSA-N 0.000 claims 1
- LFVFUUBRPMCKGZ-UHFFFAOYSA-N 2,3-dichloro-n-[2-(4,4-difluorocyclohexyl)-2-(2-methylpyrimidin-5-yl)ethyl]benzamide Chemical compound C1=NC(C)=NC=C1C(C1CCC(F)(F)CC1)CNC(=O)C1=CC=CC(Cl)=C1Cl LFVFUUBRPMCKGZ-UHFFFAOYSA-N 0.000 claims 1
- KMYKPPPJRDAZAH-UHFFFAOYSA-N 2,3-dichloro-n-[2-(4,4-difluorocyclohexyl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide Chemical compound C1=NC(C(F)(F)F)=NC=C1C(C1CCC(F)(F)CC1)CNC(=O)C1=CC=CC(Cl)=C1Cl KMYKPPPJRDAZAH-UHFFFAOYSA-N 0.000 claims 1
- SMCKEZRORVPHFF-UHFFFAOYSA-N 2,3-dichloro-n-[2-(4-chlorophenyl)-2-phenylethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)CNC(=O)C1=CC=CC(Cl)=C1Cl SMCKEZRORVPHFF-UHFFFAOYSA-N 0.000 claims 1
- IGFZEMQKBHZFBX-UHFFFAOYSA-N 2,3-dichloro-n-[2-(4-fluorophenyl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide Chemical compound C1=CC(F)=CC=C1C(C=1C=NC(=NC=1)C(F)(F)F)CNC(=O)C1=CC=CC(Cl)=C1Cl IGFZEMQKBHZFBX-UHFFFAOYSA-N 0.000 claims 1
- DINZZVNXDSWLAN-UHFFFAOYSA-N 2,3-dichloro-n-[2-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]ethyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(C1CC1)CNC(=O)C1=CC=CC(Cl)=C1Cl DINZZVNXDSWLAN-UHFFFAOYSA-N 0.000 claims 1
- SKGNSFHTXOMKPD-UHFFFAOYSA-N 2,3-dichloro-n-[3-cyclopropyl-2-(2,6-dimethylpyridin-3-yl)propyl]benzamide Chemical compound CC1=NC(C)=CC=C1C(CC1CC1)CNC(=O)C1=CC=CC(Cl)=C1Cl SKGNSFHTXOMKPD-UHFFFAOYSA-N 0.000 claims 1
- FJZHHXCQDLYUDX-UHFFFAOYSA-N 2,3-dichloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(CC1CC1)CNC(=O)C1=CC=CC(Cl)=C1Cl FJZHHXCQDLYUDX-UHFFFAOYSA-N 0.000 claims 1
- XTPKQBKANGHQJW-UHFFFAOYSA-N 2,3-dichloro-n-[3-cyclopropyl-2-methyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C1CC1CC(C=1C=NC(=NC=1)C(F)(F)F)(C)CNC(=O)C1=CC=CC(Cl)=C1Cl XTPKQBKANGHQJW-UHFFFAOYSA-N 0.000 claims 1
- SILHYWNUBWSHLP-UHFFFAOYSA-N 2,3-dichloro-n-[4-methoxy-2-[2-(trifluoromethyl)pyrimidin-5-yl]butyl]benzamide Chemical compound C=1N=C(C(F)(F)F)N=CC=1C(CCOC)CNC(=O)C1=CC=CC(Cl)=C1Cl SILHYWNUBWSHLP-UHFFFAOYSA-N 0.000 claims 1
- UPZAMGNRGNYKDQ-UHFFFAOYSA-N 2,3-dichloro-n-[[3-(2-methylpyrimidin-5-yl)oxolan-3-yl]methyl]benzamide Chemical compound C1=NC(C)=NC=C1C1(CNC(=O)C=2C(=C(Cl)C=CC=2)Cl)COCC1 UPZAMGNRGNYKDQ-UHFFFAOYSA-N 0.000 claims 1
- UZKXTPHGWOFFHL-UHFFFAOYSA-N 2,3-dichloro-n-[[4,4-difluoro-1-(6-fluoropyridin-3-yl)cyclohexyl]methyl]benzamide Chemical compound C1=NC(F)=CC=C1C1(CNC(=O)C=2C(=C(Cl)C=CC=2)Cl)CCC(F)(F)CC1 UZKXTPHGWOFFHL-UHFFFAOYSA-N 0.000 claims 1
- KQXQMXLYWFOMLN-UHFFFAOYSA-N 2,3-dichloro-n-[[4,4-difluoro-1-(6-methoxypyridin-3-yl)cyclohexyl]methyl]benzamide Chemical compound C1=NC(OC)=CC=C1C1(CNC(=O)C=2C(=C(Cl)C=CC=2)Cl)CCC(F)(F)CC1 KQXQMXLYWFOMLN-UHFFFAOYSA-N 0.000 claims 1
- BGUNDSQMAWDSDP-UHFFFAOYSA-N 2,3-dichloro-n-[[4,4-difluoro-1-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]cyclohexyl]methyl]benzamide Chemical compound C1=NC(C(C)(O)C)=CC=C1C1(CNC(=O)C=2C(=C(Cl)C=CC=2)Cl)CCC(F)(F)CC1 BGUNDSQMAWDSDP-UHFFFAOYSA-N 0.000 claims 1
- NBTYBSNXBADVPU-UHFFFAOYSA-N 2,4-dichloro-n-[2-phenyl-2-[6-(trifluoromethyl)pyridin-3-yl]ethyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(C=1C=CC=CC=1)CNC(=O)C1=CC=C(Cl)C=C1Cl NBTYBSNXBADVPU-UHFFFAOYSA-N 0.000 claims 1
- WYMCMIODUHKIJX-UHFFFAOYSA-N 2,6-dichloro-n-[3-cyclopropyl-2-(2-methylpyrimidin-5-yl)propyl]benzamide Chemical compound C1=NC(C)=NC=C1C(CC1CC1)CNC(=O)C1=C(Cl)C=CC=C1Cl WYMCMIODUHKIJX-UHFFFAOYSA-N 0.000 claims 1
- HGZIMQXJAFSFJC-UHFFFAOYSA-N 2,6-dichloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C(CC1CC1)CNC(=O)C1=C(Cl)C=CC=C1Cl HGZIMQXJAFSFJC-UHFFFAOYSA-N 0.000 claims 1
- BRBBOPAVAKEXHC-UHFFFAOYSA-N 2-chloro-5-methyl-n-[(1-pyridin-3-ylcyclopentyl)methyl]benzamide Chemical compound CC1=CC=C(Cl)C(C(=O)NCC2(CCCC2)C=2C=NC=CC=2)=C1 BRBBOPAVAKEXHC-UHFFFAOYSA-N 0.000 claims 1
- AULWKBUDPZVQJH-UHFFFAOYSA-N 2-chloro-5-methyl-n-[[4-(6-methylpyridin-3-yl)oxan-4-yl]methyl]benzamide Chemical compound CC1=CC=C(Cl)C(C(=O)NCC2(CCOCC2)C=2C=NC(C)=CC=2)=C1 AULWKBUDPZVQJH-UHFFFAOYSA-N 0.000 claims 1
- YADAFFKKFONQQM-UHFFFAOYSA-N 2-chloro-6-fluoro-n-[2-(4-fluorophenyl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide Chemical compound C1=CC(F)=CC=C1C(C=1C=NC(=NC=1)C(F)(F)F)CNC(=O)C1=C(F)C=CC=C1Cl YADAFFKKFONQQM-UHFFFAOYSA-N 0.000 claims 1
- QSLKTTDGZTXERS-UHFFFAOYSA-N 2-chloro-n-[2-(4,4-difluorocyclohexyl)-2-(2-methylpyrimidin-5-yl)ethyl]-3-fluorobenzamide Chemical compound C1=NC(C)=NC=C1C(C1CCC(F)(F)CC1)CNC(=O)C1=CC=CC(F)=C1Cl QSLKTTDGZTXERS-UHFFFAOYSA-N 0.000 claims 1
- PDYWWWPDYNSJPI-UHFFFAOYSA-N 2-chloro-n-[2-(4,4-difluorocyclohexyl)-2-(2-methylpyrimidin-5-yl)ethyl]benzamide Chemical compound C1=NC(C)=NC=C1C(C1CCC(F)(F)CC1)CNC(=O)C1=CC=CC=C1Cl PDYWWWPDYNSJPI-UHFFFAOYSA-N 0.000 claims 1
- AKKNTLAHCTWLLO-UHFFFAOYSA-N 2-chloro-n-[2-(4,4-difluorocyclohexyl)-2-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]benzamide Chemical compound C1=NC(C(F)(F)F)=NC=C1C(C1CCC(F)(F)CC1)CNC(=O)C1=CC=CC=C1Cl AKKNTLAHCTWLLO-UHFFFAOYSA-N 0.000 claims 1
- LPJZCUNIFPBMAB-UHFFFAOYSA-N 2-chloro-n-[2-(4-chlorophenyl)-2-(oxan-4-yl)ethyl]-3-fluorobenzamide Chemical compound FC1=CC=CC(C(=O)NCC(C2CCOCC2)C=2C=CC(Cl)=CC=2)=C1Cl LPJZCUNIFPBMAB-UHFFFAOYSA-N 0.000 claims 1
- QZZXFAFHZPJKEY-UHFFFAOYSA-N 2-chloro-n-[2-(6-cyclopropylpyridin-3-yl)-3-[1-(trifluoromethyl)cyclopropyl]propyl]benzamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)NCC(C=1C=NC(=CC=1)C1CC1)CC1(C(F)(F)F)CC1 QZZXFAFHZPJKEY-UHFFFAOYSA-N 0.000 claims 1
- UIGGFHHHBJIJNF-UHFFFAOYSA-N 2-chloro-n-[3-[1-(trifluoromethyl)cyclopropyl]-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]benzamide Chemical compound C1=NC(C(F)(F)F)=NC=C1C(CC1(CC1)C(F)(F)F)CNC(=O)C1=CC=CC=C1Cl UIGGFHHHBJIJNF-UHFFFAOYSA-N 0.000 claims 1
- HJUJINBFFMFWOK-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCC(CC2CC2)C=2C=NC(=NC=2)C(F)(F)F)=C1Cl HJUJINBFFMFWOK-UHFFFAOYSA-N 0.000 claims 1
- KIQGXQAXDPCWDW-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-3-fluorobenzamide Chemical compound FC1=CC=CC(C(=O)NCC(CC2CC2)C=2C=NC(=CC=2)C(F)(F)F)=C1Cl KIQGXQAXDPCWDW-UHFFFAOYSA-N 0.000 claims 1
- NKAHZWJMIBLLBN-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-4-fluorobenzamide Chemical compound ClC1=CC(F)=CC=C1C(=O)NCC(C=1C=NC(=CC=1)C(F)(F)F)CC1CC1 NKAHZWJMIBLLBN-UHFFFAOYSA-N 0.000 claims 1
- STCXIRZKWXHTIY-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]-6-fluorobenzamide Chemical compound FC1=CC=CC(Cl)=C1C(=O)NCC(C=1C=NC(=CC=1)C(F)(F)F)CC1CC1 STCXIRZKWXHTIY-UHFFFAOYSA-N 0.000 claims 1
- VQMPIFDHXSJHBL-UHFFFAOYSA-N 2-chloro-n-[3-cyclopropyl-2-methyl-2-[2-(trifluoromethyl)pyrimidin-5-yl]propyl]-3-fluorobenzamide Chemical compound C1CC1CC(C=1C=NC(=NC=1)C(F)(F)F)(C)CNC(=O)C1=CC=CC(F)=C1Cl VQMPIFDHXSJHBL-UHFFFAOYSA-N 0.000 claims 1
- UJPFCELJBTZEEG-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]cyclohexyl]methyl]benzamide Chemical compound C1=NC(C(C)(O)C)=CC=C1C1(CNC(=O)C=2C(=CC=CC=2)Cl)CCC(F)(F)CC1 UJPFCELJBTZEEG-UHFFFAOYSA-N 0.000 claims 1
- HDRBTBXDTSMYEF-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[6-(trifluoromethyl)pyridin-3-yl]cyclohexyl]methyl]-3-fluorobenzamide Chemical compound FC1=CC=CC(C(=O)NCC2(CCC(F)(F)CC2)C=2C=NC(=CC=2)C(F)(F)F)=C1Cl HDRBTBXDTSMYEF-UHFFFAOYSA-N 0.000 claims 1
- FNNMLSLAWOXSFS-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[6-(trifluoromethyl)pyridin-3-yl]cyclohexyl]methyl]benzamide Chemical compound C1=NC(C(F)(F)F)=CC=C1C1(CNC(=O)C=2C(=CC=CC=2)Cl)CCC(F)(F)CC1 FNNMLSLAWOXSFS-UHFFFAOYSA-N 0.000 claims 1
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 claims 1
- OZRXZNCUIZXGPD-UHFFFAOYSA-N 2-methyl-n-[(1-methyl-4-phenylpiperidin-4-yl)methyl]benzamide Chemical compound C1CN(C)CCC1(C=1C=CC=CC=1)CNC(=O)C1=CC=CC=C1C OZRXZNCUIZXGPD-UHFFFAOYSA-N 0.000 claims 1
- YZSHNJLAVFLXCZ-UHFFFAOYSA-N 2-methyl-n-[(1-pyridin-3-ylcyclopentyl)methyl]benzamide Chemical compound CC1=CC=CC=C1C(=O)NCC1(C=2C=NC=CC=2)CCCC1 YZSHNJLAVFLXCZ-UHFFFAOYSA-N 0.000 claims 1
- YGOWSFIWUXDWHH-UHFFFAOYSA-N 3-chloro-n-[[4,4-difluoro-1-(6-fluoropyridin-3-yl)cyclohexyl]methyl]-2-fluorobenzamide Chemical compound C1=NC(F)=CC=C1C1(CNC(=O)C=2C(=C(Cl)C=CC=2)F)CCC(F)(F)CC1 YGOWSFIWUXDWHH-UHFFFAOYSA-N 0.000 claims 1
- HAVDOEUAXIXGLG-UHFFFAOYSA-N 3-chloro-n-[[4,4-difluoro-1-[6-(trifluoromethyl)pyridin-3-yl]cyclohexyl]methyl]-2-fluorobenzamide Chemical compound FC1=C(Cl)C=CC=C1C(=O)NCC1(C=2C=NC(=CC=2)C(F)(F)F)CCC(F)(F)CC1 HAVDOEUAXIXGLG-UHFFFAOYSA-N 0.000 claims 1
- HIFWGNXCXSJOQM-UHFFFAOYSA-N 3-cyano-n-[[4,4-difluoro-1-[6-(trifluoromethyl)pyridin-3-yl]cyclohexyl]methyl]-2-methylbenzamide Chemical compound CC1=C(C#N)C=CC=C1C(=O)NCC1(C=2C=NC(=CC=2)C(F)(F)F)CCC(F)(F)CC1 HIFWGNXCXSJOQM-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- DVMILACIDBEACH-UHFFFAOYSA-N 6-fluoropyridine Chemical compound FC1=C=CC=C[N]1 DVMILACIDBEACH-UHFFFAOYSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- IEXREEGPHRESLW-UHFFFAOYSA-N C1CC1CC(CC2=C(C(=CC=C2)C(=O)N)F)C3=CN=C(C=C3)C(F)(F)F Chemical compound C1CC1CC(CC2=C(C(=CC=C2)C(=O)N)F)C3=CN=C(C=C3)C(F)(F)F IEXREEGPHRESLW-UHFFFAOYSA-N 0.000 claims 1
- OPHNOSLOPXXLBN-UHFFFAOYSA-N COC1=CC=CC(C(=O)NCC2(CCC(F)(F)CC2)C=2C=NC(=CC=2)C(F)(F)F)=C1Cl Chemical compound COC1=CC=CC(C(=O)NCC2(CCC(F)(F)CC2)C=2C=NC(=CC=2)C(F)(F)F)=C1Cl OPHNOSLOPXXLBN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- GOBCJRHIQNXGJC-UHFFFAOYSA-N N-[3-cyclopropyl-2-[6-(trifluoromethyl)pyridin-3-yl]propyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC(CC1CC1)C=1C=NC(=CC=1)C(F)(F)F GOBCJRHIQNXGJC-UHFFFAOYSA-N 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- XNDJMGGHPSVLDD-UHFFFAOYSA-N n-[1-[1-(6-bromopyridin-3-yl)-4,4-difluorocyclohexyl]ethyl]-2,3-dichlorobenzamide Chemical compound C1CC(F)(F)CCC1(C=1C=NC(Br)=CC=1)C(C)NC(=O)C1=CC=CC(Cl)=C1Cl XNDJMGGHPSVLDD-UHFFFAOYSA-N 0.000 claims 1
- QHRQPOIUZGTIBU-UHFFFAOYSA-N n-[2-(6-cyclopropylpyridin-3-yl)-3-[1-(trifluoromethyl)cyclopropyl]propyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NCC(C=1C=NC(=CC=1)C1CC1)CC1(C(F)(F)F)CC1 QHRQPOIUZGTIBU-UHFFFAOYSA-N 0.000 claims 1
- AGMKGWPDQSRSFK-UHFFFAOYSA-N n-[[4,4-difluoro-1-(6-fluoropyridin-3-yl)cyclohexyl]methyl]-2,3-difluorobenzamide Chemical compound C1=NC(F)=CC=C1C1(CNC(=O)C=2C(=C(F)C=CC=2)F)CCC(F)(F)CC1 AGMKGWPDQSRSFK-UHFFFAOYSA-N 0.000 claims 1
- QHQDQDLSKSNOLG-UHFFFAOYSA-N n-[[4,4-difluoro-1-(6-fluoropyridin-3-yl)cyclohexyl]methyl]-2,5-difluorobenzamide Chemical compound FC1=CC=C(F)C(C(=O)NCC2(CCC(F)(F)CC2)C=2C=NC(F)=CC=2)=C1 QHQDQDLSKSNOLG-UHFFFAOYSA-N 0.000 claims 1
- IMOIERUKFGRYQV-UHFFFAOYSA-N n-[[4,4-difluoro-1-[6-(trifluoromethyl)pyridin-3-yl]cyclohexyl]methyl]-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC=C(C(F)(F)F)C=C1C(=O)NCC1(C=2C=NC(=CC=2)C(F)(F)F)CCC(F)(F)CC1 IMOIERUKFGRYQV-UHFFFAOYSA-N 0.000 claims 1
- BKYHGKOROKCTFZ-UHFFFAOYSA-N n-[[4,4-difluoro-1-[6-(trifluoromethyl)pyridin-3-yl]cyclohexyl]methyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NCC1(C=2C=NC(=CC=2)C(F)(F)F)CCC(F)(F)CC1 BKYHGKOROKCTFZ-UHFFFAOYSA-N 0.000 claims 1
- RYQGLJRJOOJJSD-UHFFFAOYSA-N n-[[4,4-difluoro-1-[6-(trifluoromethyl)pyridin-3-yl]cyclohexyl]methyl]-3-fluoro-2-methylbenzamide Chemical compound CC1=C(F)C=CC=C1C(=O)NCC1(C=2C=NC(=CC=2)C(F)(F)F)CCC(F)(F)CC1 RYQGLJRJOOJJSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 102100037602 P2X purinoceptor 7 Human genes 0.000 abstract 1
- 101710189965 P2X purinoceptor 7 Proteins 0.000 abstract 1
Classifications
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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- C07C233/73—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/61—Halogen atoms or nitro radicals
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- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261713113P | 2012-10-12 | 2012-10-12 | |
| PCT/EP2013/071247 WO2014057078A1 (en) | 2012-10-12 | 2013-10-11 | Benzamides |
| EP13786633.1A EP2906546B1 (en) | 2012-10-12 | 2013-10-11 | Benzamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI2906546T1 true SI2906546T1 (en) | 2018-05-31 |
Family
ID=49551580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI201330967T SI2906546T1 (en) | 2012-10-12 | 2013-10-11 | Benzamides |
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Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI598325B (zh) * | 2012-10-12 | 2017-09-11 | H 朗德貝克公司 | 苯甲醯胺類 |
| TW201427947A (zh) | 2012-10-12 | 2014-07-16 | Lundbeck & Co As H | 環狀胺 |
| PL2931717T3 (pl) | 2012-12-12 | 2017-05-31 | Actelion Pharmaceuticals Ltd. | Pochodne indolokarboksyamidu jako antagoniści receptora p2x7 |
| AR094053A1 (es) | 2012-12-18 | 2015-07-08 | Actelion Pharmaceuticals Ltd | Derivados de indol carboxamida como antagonistas del receptor p2x₇ |
| EP2956457B1 (en) | 2013-01-22 | 2016-11-23 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| ES2616114T3 (es) | 2013-01-22 | 2017-06-09 | Actelion Pharmaceuticals Ltd. | Derivados de amida heterocíclica como antagonistas del receptor P2X7 |
| CN105503787A (zh) * | 2015-12-31 | 2016-04-20 | 阜阳欣奕华材料科技有限公司 | 一种索非布韦中间体的纯化方法 |
| CN106366056B (zh) * | 2016-08-26 | 2018-12-11 | 常州市阳光药业有限公司 | 3-氨甲基四氢呋喃的制备方法 |
| SI3609868T1 (sl) * | 2017-03-13 | 2024-03-29 | Raqualia Pharma Inc. | Derivati tetrahidrokinolina kot antagonisti receptorja P2X7 |
| WO2019226213A2 (en) | 2018-03-08 | 2019-11-28 | Incyte Corporation | AMINOPYRAZINE DIOL COMPOUNDS AS PI3K-y INHIBITORS |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| MA55805A (fr) | 2019-05-03 | 2022-03-09 | Flagship Pioneering Innovations V Inc | Métodes de modulation de l'activité immunitaire |
| CN117088877A (zh) * | 2020-10-28 | 2023-11-21 | 杭州阿诺生物医药科技有限公司 | 一种高活性Wnt通路抑制剂化合物 |
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| DE1445707A1 (de) | 1962-05-05 | 1969-03-13 | Hoechst Ag | Piperidinverbindungen und Verfahren zu ihrer Herstellung |
| US3435038A (en) * | 1965-06-01 | 1969-03-25 | Sandoz Ag | 5,6,7,9,10,14b-hexahydroisoquinolo (2,1-d) benzo (1,4) diazepines |
| US6303637B1 (en) * | 1998-10-30 | 2001-10-16 | Merck & Co., Inc. | Heterocyclic potassium channel inhibitors |
| US6194458B1 (en) * | 1998-10-30 | 2001-02-27 | Merck & Co., Inc. | Benzamide potassium channel inhibitors |
| US6632836B1 (en) * | 1998-10-30 | 2003-10-14 | Merck & Co., Inc. | Carbocyclic potassium channel inhibitors |
| SE0003476D0 (sv) * | 2000-09-28 | 2000-09-28 | Astrazeneca Ab | Compounds |
| TW200300083A (en) | 2001-11-12 | 2003-05-16 | Pfizer Prod Inc | Benzamide, heteroarylamide and reverse amides |
| PA8557501A1 (es) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
| TW200403058A (en) * | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| PA8591801A1 (es) * | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
| ATE355273T1 (de) * | 2003-05-12 | 2006-03-15 | Pfizer Prod Inc | Benzamidinhibitoren des p2x7-rezeptors |
| AU2004263179B8 (en) | 2003-08-08 | 2011-07-14 | Vertex Pharmaceuticals Incorporated | Heteroarylaminosulfonylphenyl derivatives for use as sodium or calcium channel blockers in the treatment of pain |
| TWI368482B (en) | 2003-12-19 | 2012-07-21 | Bayer Sas | New 2-pyridinylethylbenzamide derivatives |
| EP1729772B8 (en) | 2004-03-24 | 2017-04-19 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine glycine transporter inhibitors |
| JP2008504363A (ja) * | 2004-06-29 | 2008-02-14 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | P2x7受容体のベンズアミド阻害剤を利用する併用療法 |
| ATE476431T1 (de) * | 2004-12-21 | 2010-08-15 | Merck Sharp & Dohme | Piperidin- und azetidinderivate als glyt1- inhibitoren |
| WO2006080884A1 (en) * | 2005-01-27 | 2006-08-03 | Astrazeneca Ab | Novel biaromatic compounds, inhibitors of the p2x7-receptor |
| CA2611376C (en) * | 2005-06-13 | 2013-09-10 | Merck Sharp & Dohme Limited | Therapeutic agents |
| CA2625039A1 (en) | 2005-10-19 | 2007-04-26 | F. Hoffmann-La Roche Ag | N-phenyl phenylacetamide non-nucleoside reverse transcriptase inihibitors |
| JP2009057282A (ja) | 2005-12-19 | 2009-03-19 | Astellas Pharma Inc | カルボン酸誘導体又はその塩 |
| TWI435863B (zh) * | 2006-03-20 | 2014-05-01 | Nihon Nohyaku Co Ltd | N-2-(雜)芳基乙基甲醯胺衍生物及含該衍生物之蟲害防治劑 |
| RU2010103102A (ru) * | 2007-07-02 | 2011-08-10 | Зингента Партисипейшнс Аг (Ch) | Новые микробиоциды |
| US8642660B2 (en) * | 2007-12-21 | 2014-02-04 | The University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| JP5369173B2 (ja) * | 2008-04-22 | 2013-12-18 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | キノリン若しくはイソキノリン置換p2x7アンタゴニスト |
| ES2345527B1 (es) * | 2008-10-08 | 2011-09-08 | Hospital Clinic I Provincial De Barcelona | Sustancias bloqueadoras de los canales kv 1.3 para el tratamiento de enfermedades asociadas a hiperplasia de la intima. |
| CA2804716A1 (en) | 2010-07-12 | 2012-01-19 | Pfizer Limited | Chemical compounds |
| CA2828060C (en) * | 2011-03-02 | 2018-11-06 | The University Of Tokyo | Endoparasite control agent |
| RU2608217C2 (ru) * | 2011-11-02 | 2017-01-17 | Байер Интеллектуэль Проперти Гмбх | Соединения с нематоцидной активностью |
| PL2782565T3 (pl) * | 2011-11-25 | 2020-08-24 | Bayer Intellectual Property Gmbh | Zastosowanie arylo- i heteroarylokarboksyamidów jako środki endopasożytobójcze |
| TW201427947A (zh) * | 2012-10-12 | 2014-07-16 | Lundbeck & Co As H | 環狀胺 |
| TWI598325B (zh) | 2012-10-12 | 2017-09-11 | H 朗德貝克公司 | 苯甲醯胺類 |
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2013
- 2013-10-09 TW TW102136498A patent/TWI598325B/zh active
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- 2013-10-11 KR KR1020157009187A patent/KR20150067188A/ko not_active Withdrawn
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2014
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2015
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2019
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