RU2007133655A - Замещенные бис-арильные и гетероарильные соединения в качестве селективных антагонистов 5нт2а - Google Patents
Замещенные бис-арильные и гетероарильные соединения в качестве селективных антагонистов 5нт2а Download PDFInfo
- Publication number
- RU2007133655A RU2007133655A RU2007133655/04A RU2007133655A RU2007133655A RU 2007133655 A RU2007133655 A RU 2007133655A RU 2007133655/04 A RU2007133655/04 A RU 2007133655/04A RU 2007133655 A RU2007133655 A RU 2007133655A RU 2007133655 A RU2007133655 A RU 2007133655A
- Authority
- RU
- Russia
- Prior art keywords
- fluoro
- benzyl
- indol
- ylmethyl
- phenyl
- Prior art date
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- 125000001072 heteroaryl group Chemical group 0.000 title claims 8
- 239000005557 antagonist Substances 0.000 title 1
- -1 enantiomers Chemical class 0.000 claims 162
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 27
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 125000002541 furyl group Chemical group 0.000 claims 18
- 125000004076 pyridyl group Chemical group 0.000 claims 18
- 125000001544 thienyl group Chemical group 0.000 claims 18
- 125000001207 fluorophenyl group Chemical group 0.000 claims 17
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 9
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical group C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 9
- 125000004193 piperazinyl group Chemical group 0.000 claims 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000000068 chlorophenyl group Chemical group 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000006332 fluoro benzoyl group Chemical group 0.000 claims 8
- 125000004175 fluorobenzyl group Chemical group 0.000 claims 8
- 230000003287 optical effect Effects 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 8
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000006333 difluoro benzoyl group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 208000019116 sleep disease Diseases 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 208000020685 sleep-wake disease Diseases 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 206010022437 insomnia Diseases 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- WHOZDLQKWBNXOC-UHFFFAOYSA-N 1,4-dioxine-2-carboxamide Chemical compound NC(=O)C1=COC=CO1 WHOZDLQKWBNXOC-UHFFFAOYSA-N 0.000 claims 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- DQUUDWQTMYMNNL-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=C(C(F)=CC=1)C(F)(F)F)CC1=CC(C=2C=C3C=CNC3=CC=2)=CC=C1F DQUUDWQTMYMNNL-UHFFFAOYSA-N 0.000 claims 1
- HSKVFCUSNYYKBX-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N(CC=1C(=CC=C(C=1)C=1C=C2C=CNC2=CC=1)F)CCN1CCCC1 HSKVFCUSNYYKBX-UHFFFAOYSA-N 0.000 claims 1
- RGSJEKWEARVCBT-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-pyrrolo[2,3-c]pyridin-5-yl)phenyl]methyl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N(CC=1C(=CC=C(C=1)C=1N=CC=2NC=CC=2C=1)F)CCN1CCCC1 RGSJEKWEARVCBT-UHFFFAOYSA-N 0.000 claims 1
- PNEOKAGWIFEWNK-UHFFFAOYSA-N 5-[3-[(4-methyl-1,4-diazepan-1-yl)methyl]phenyl]-1h-indole Chemical compound C1CN(C)CCCN1CC1=CC=CC(C=2C=C3C=CNC3=CC=2)=C1 PNEOKAGWIFEWNK-UHFFFAOYSA-N 0.000 claims 1
- IIZXKGJRAXFWTJ-UHFFFAOYSA-N 5-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-indole Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2C=C3C=CNC3=CC=2)=C1 IIZXKGJRAXFWTJ-UHFFFAOYSA-N 0.000 claims 1
- HAAPQNSHWVROTN-UHFFFAOYSA-N 5-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-2h-benzotriazole Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2C=C3N=NNC3=CC=2)=C1 HAAPQNSHWVROTN-UHFFFAOYSA-N 0.000 claims 1
- CAKWHMWWQGQGJS-UHFFFAOYSA-N 5-[3-[[benzyl-[2-(dimethylamino)ethyl]amino]methyl]phenyl]-1,3-dihydrobenzimidazol-2-one;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3NC(=O)NC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 CAKWHMWWQGQGJS-UHFFFAOYSA-N 0.000 claims 1
- POCWULSIEIASHP-UHFFFAOYSA-N 5-[4-fluoro-3-[(2-thiophen-2-ylpiperazin-1-yl)methyl]phenyl]-1h-indazole Chemical compound FC1=CC=C(C=2C=C3C=NNC3=CC=2)C=C1CN1CCNCC1C1=CC=CS1 POCWULSIEIASHP-UHFFFAOYSA-N 0.000 claims 1
- CBGLMQWHEAXZDJ-UHFFFAOYSA-N 5-[4-fluoro-3-[(4-methyl-2-pyridin-4-ylpiperazin-1-yl)methyl]phenyl]-1h-indole Chemical compound C1N(C)CCN(CC=2C(=CC=C(C=2)C=2C=C3C=CNC3=CC=2)F)C1C1=CC=NC=C1 CBGLMQWHEAXZDJ-UHFFFAOYSA-N 0.000 claims 1
- WZNQSOMASICACW-UHFFFAOYSA-N 5-[4-fluoro-3-[(4-methylpiperazin-1-yl)methyl]phenyl]-2h-benzotriazole Chemical compound C1CN(C)CCN1CC1=CC(C=2C=C3N=NNC3=CC=2)=CC=C1F WZNQSOMASICACW-UHFFFAOYSA-N 0.000 claims 1
- CYPMENQZAYYMTF-UHFFFAOYSA-N 5-[4-fluoro-3-[[2-(4-fluorophenyl)-4-methylpiperazin-1-yl]methyl]phenyl]-1h-pyrrolo[3,2-b]pyridine Chemical compound C1N(C)CCN(CC=2C(=CC=C(C=2)C=2N=C3C=CNC3=CC=2)F)C1C1=CC=C(F)C=C1 CYPMENQZAYYMTF-UHFFFAOYSA-N 0.000 claims 1
- GJHBOZUUYVMRNH-UHFFFAOYSA-N 5-[4-fluoro-3-[[2-(4-fluorophenyl)piperazin-1-yl]methyl]phenyl]-1h-indazole Chemical compound C1=CC(F)=CC=C1C1N(CC=2C(=CC=C(C=2)C=2C=C3C=NNC3=CC=2)F)CCNC1 GJHBOZUUYVMRNH-UHFFFAOYSA-N 0.000 claims 1
- MNGZJBFTHGLPQE-UHFFFAOYSA-N 5-[4-fluoro-3-[[2-(furan-2-yl)-4-methylpiperazin-1-yl]methyl]phenyl]-1h-indole Chemical compound C1N(C)CCN(CC=2C(=CC=C(C=2)C=2C=C3C=CNC3=CC=2)F)C1C1=CC=CO1 MNGZJBFTHGLPQE-UHFFFAOYSA-N 0.000 claims 1
- GQFXAFQSILNKAW-UHFFFAOYSA-N 5-[4-fluoro-3-[[4-methyl-2-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]phenyl]-1h-indole Chemical compound C1N(C)CCN(CC=2C(=CC=C(C=2)C=2C=C3C=CNC3=CC=2)F)C1C1=CC=C(C(F)(F)F)C=C1 GQFXAFQSILNKAW-UHFFFAOYSA-N 0.000 claims 1
- REPHVNGRWIFVMJ-UHFFFAOYSA-N 6-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-3h-1,3-benzoxazol-2-one Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2C=C3OC(=O)NC3=CC=2)=C1 REPHVNGRWIFVMJ-UHFFFAOYSA-N 0.000 claims 1
- CLAHVIWPABLYNF-UHFFFAOYSA-N 6-[3-[[benzyl-[2-(dimethylamino)ethyl]amino]methyl]phenyl]-3-methyl-1h-quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3C(=O)N(C)C(=O)NC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 CLAHVIWPABLYNF-UHFFFAOYSA-N 0.000 claims 1
- JLMVYNXQXVHUDX-UHFFFAOYSA-N 6-[3-[[benzyl-[2-(dimethylamino)ethyl]amino]methyl]phenyl]-3h-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3SC(=O)NC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 JLMVYNXQXVHUDX-UHFFFAOYSA-N 0.000 claims 1
- JJPMWPVVCZNYSC-UHFFFAOYSA-N 6-[3-[[benzyl-[2-(dimethylamino)ethyl]amino]methyl]phenyl]-3h-1,3-benzoxazol-2-one;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3OC(=O)NC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 JJPMWPVVCZNYSC-UHFFFAOYSA-N 0.000 claims 1
- BYNVFXLKWAWEFK-UHFFFAOYSA-N 6-[4-fluoro-3-[(2-thiophen-2-ylpiperazin-1-yl)methyl]phenyl]-3h-1,3-benzoxazol-2-one Chemical compound FC1=CC=C(C=2C=C3OC(=O)NC3=CC=2)C=C1CN1CCNCC1C1=CC=CS1 BYNVFXLKWAWEFK-UHFFFAOYSA-N 0.000 claims 1
- FTLJTVKXADVTQC-UHFFFAOYSA-N 6-[4-fluoro-3-[[(4-fluorophenyl)methyl-(1-methylpiperidin-4-yl)amino]methyl]phenyl]-3h-1,3-benzoxazol-2-one Chemical compound C1CN(C)CCC1N(CC=1C(=CC=C(C=1)C=1C=C2OC(=O)NC2=CC=1)F)CC1=CC=C(F)C=C1 FTLJTVKXADVTQC-UHFFFAOYSA-N 0.000 claims 1
- IKFVERNEDYZIRR-UHFFFAOYSA-N 6-[5-[[(4-fluorophenyl)methyl-(1-methylpiperidin-4-yl)amino]methyl]furan-3-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1CN(C)CCC1N(CC=1C=CC(F)=CC=1)CC1=CC(C=2C=C3OC(=O)NC3=CC=2)=CO1 IKFVERNEDYZIRR-UHFFFAOYSA-N 0.000 claims 1
- HBINRFRIDMACKS-UHFFFAOYSA-N 6-[5-[[2-(dimethylamino)ethyl-[(4-fluorophenyl)methyl]amino]methyl]pyridin-3-yl]-3h-1,3-benzoxazol-2-one Chemical compound C=1N=CC(C=2C=C3OC(=O)NC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=C(F)C=C1 HBINRFRIDMACKS-UHFFFAOYSA-N 0.000 claims 1
- MHRWDIMYIWMUOS-UHFFFAOYSA-N 7-[3-[[benzyl-[2-(dimethylamino)ethyl]amino]methyl]phenyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3OCC(=O)NC3=NC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 MHRWDIMYIWMUOS-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- OMNCZRGZYURYEO-UHFFFAOYSA-N acetic acid;5-[4-fluoro-3-[(2-thiophen-2-ylpiperazin-1-yl)methyl]phenyl]-1h-indazole Chemical compound CC(O)=O.FC1=CC=C(C=2C=C3C=NNC3=CC=2)C=C1CN1CCNCC1C1=CC=CS1 OMNCZRGZYURYEO-UHFFFAOYSA-N 0.000 claims 1
- SJFFDJGHUDCLNC-UHFFFAOYSA-N acetic acid;5-[4-fluoro-3-[(4-methyl-2-pyridin-2-ylpiperazin-1-yl)methyl]phenyl]-1h-indole Chemical compound CC(O)=O.C1N(C)CCN(CC=2C(=CC=C(C=2)C=2C=C3C=CNC3=CC=2)F)C1C1=CC=CC=N1 SJFFDJGHUDCLNC-UHFFFAOYSA-N 0.000 claims 1
- ZATHGVHUMFFOPY-UHFFFAOYSA-N acetic acid;5-[4-fluoro-3-[(4-methyl-2-pyridin-3-ylpiperazin-1-yl)methyl]phenyl]-1h-indole Chemical compound CC(O)=O.C1N(C)CCN(CC=2C(=CC=C(C=2)C=2C=C3C=CNC3=CC=2)F)C1C1=CC=CN=C1 ZATHGVHUMFFOPY-UHFFFAOYSA-N 0.000 claims 1
- WHSAOBZVNVTBQH-UHFFFAOYSA-N acetic acid;n'-[(4-fluorophenyl)methyl]-n'-[[5-(1h-indazol-5-yl)pyridin-3-yl]methyl]-n,n-dimethylethane-1,2-diamine Chemical compound CC(O)=O.C=1N=CC(C=2C=C3C=NNC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=C(F)C=C1 WHSAOBZVNVTBQH-UHFFFAOYSA-N 0.000 claims 1
- NNEUDDYXKARJJP-UHFFFAOYSA-N acetic acid;n-[[4-fluoro-3-(1h-indol-5-yl)phenyl]methyl]-n-(2-pyrrolidin-1-ylethyl)-4-(trifluoromethoxy)benzamide Chemical compound CC(O)=O.C1=C(C=2C=C3C=CNC3=CC=2)C(F)=CC=C1CN(C(=O)C=1C=CC(OC(F)(F)F)=CC=1)CCN1CCCC1 NNEUDDYXKARJJP-UHFFFAOYSA-N 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- NORFKNIONUICLG-UHFFFAOYSA-N n'-[[2-fluoro-5-(1h-indazol-5-yl)phenyl]methyl]-n'-[(4-fluorophenyl)methyl]-n-methylethane-1,2-diamine Chemical compound C=1C(C=2C=C3C=NNC3=CC=2)=CC=C(F)C=1CN(CCNC)CC1=CC=C(F)C=C1 NORFKNIONUICLG-UHFFFAOYSA-N 0.000 claims 1
- VJPMQXAWZUFURF-UHFFFAOYSA-N n'-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n'-[(4-fluorophenyl)methyl]-n,n-dimethylethane-1,2-diamine Chemical compound C=1C(C=2C=C3C=CNC3=CC=2)=CC=C(F)C=1CN(CCN(C)C)CC1=CC=C(F)C=C1 VJPMQXAWZUFURF-UHFFFAOYSA-N 0.000 claims 1
- XTKIJZIFRJNQDD-UHFFFAOYSA-N n'-[[3-(2h-benzotriazol-5-yl)phenyl]methyl]-n'-benzyl-n,n-dimethylethane-1,2-diamine;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3N=NNC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 XTKIJZIFRJNQDD-UHFFFAOYSA-N 0.000 claims 1
- DPKOENODKZISQV-UHFFFAOYSA-N n'-[[3-(2h-benzotriazol-5-yl)phenyl]methyl]-n'-benzyl-n,n-dimethylpropane-1,3-diamine Chemical compound C=1C=CC(C=2C=C3N=NNC3=CC=2)=CC=1CN(CCCN(C)C)CC1=CC=CC=C1 DPKOENODKZISQV-UHFFFAOYSA-N 0.000 claims 1
- VPEYZBPHUGTNEJ-UHFFFAOYSA-N n'-[[3-(3h-benzimidazol-5-yl)phenyl]methyl]-n'-benzyl-n,n-dimethylethane-1,2-diamine;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3N=CNC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 VPEYZBPHUGTNEJ-UHFFFAOYSA-N 0.000 claims 1
- NAYKHKCDIGPIHB-UHFFFAOYSA-N n'-[[3-(3h-benzimidazol-5-yl)phenyl]methyl]-n'-benzyl-n,n-dimethylpropane-1,3-diamine;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3N=CNC3=CC=2)=CC=1CN(CCCN(C)C)CC1=CC=CC=C1 NAYKHKCDIGPIHB-UHFFFAOYSA-N 0.000 claims 1
- RBHFMNPEVIQOAQ-UHFFFAOYSA-N n'-[[5-(2h-benzotriazol-5-yl)-2-fluorophenyl]methyl]-n'-[(4-fluorophenyl)methyl]-n-methylethane-1,2-diamine Chemical compound C=1C(C=2C=C3N=NNC3=CC=2)=CC=C(F)C=1CN(CCNC)CC1=CC=C(F)C=C1 RBHFMNPEVIQOAQ-UHFFFAOYSA-N 0.000 claims 1
- CLRXDNKIZRKYCU-UHFFFAOYSA-N n'-benzyl-n'-[[3-(1h-indazol-5-yl)phenyl]methyl]-n,n-dimethylethane-1,2-diamine;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3C=NNC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 CLRXDNKIZRKYCU-UHFFFAOYSA-N 0.000 claims 1
- JSCTYNKYJGSRJV-UHFFFAOYSA-N n'-benzyl-n'-[[3-(1h-indol-5-yl)phenyl]methyl]-n,n-dimethylethane-1,2-diamine Chemical compound C=1C=CC(C=2C=C3C=CNC3=CC=2)=CC=1CN(CCN(C)C)CC1=CC=CC=C1 JSCTYNKYJGSRJV-UHFFFAOYSA-N 0.000 claims 1
- BWWSSMHAPVJKLD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-fluoro-n-[[5-(1h-indol-5-yl)pyridin-3-yl]methyl]benzamide Chemical compound C=1N=CC(C=2C=C3C=CNC3=CC=2)=CC=1CN(CCN(C)C)C(=O)C1=CC=C(F)C=C1 BWWSSMHAPVJKLD-UHFFFAOYSA-N 0.000 claims 1
- WRTMCHZDWZBKEX-UHFFFAOYSA-N n-[[2-fluoro-5-(1h-indazol-5-yl)phenyl]methyl]-n-[(4-fluorophenyl)methyl]piperidin-4-amine Chemical compound C1=CC(F)=CC=C1CN(C1CCNCC1)CC1=CC(C=2C=C3C=NNC3=CC=2)=CC=C1F WRTMCHZDWZBKEX-UHFFFAOYSA-N 0.000 claims 1
- OVVKQDMOZMPOLX-UHFFFAOYSA-N n-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)-3-(trifluoromethoxy)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=C(OC(F)(F)F)C=CC=1)CC1=CC(C=2C=C3C=CNC3=CC=2)=CC=C1F OVVKQDMOZMPOLX-UHFFFAOYSA-N 0.000 claims 1
- DPHQJISNFIGVKI-UHFFFAOYSA-N n-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)-4-(trifluoromethoxy)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(OC(F)(F)F)=CC=1)CC1=CC(C=2C=C3C=CNC3=CC=2)=CC=C1F DPHQJISNFIGVKI-UHFFFAOYSA-N 0.000 claims 1
- DLFONWAJSZOKII-UHFFFAOYSA-N n-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n-(2-pyrrolidin-1-ylethyl)-4-(trifluoromethyl)benzamide Chemical compound FC1=CC=C(C=2C=C3C=CNC3=CC=2)C=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CCN1CCCC1 DLFONWAJSZOKII-UHFFFAOYSA-N 0.000 claims 1
- PLMOMLSRTDHBEA-UHFFFAOYSA-N n-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n-[(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine Chemical compound C1CN(C)CCC1N(CC=1C(=CC=C(C=1)C=1C=C2C=CNC2=CC=1)F)CC1=CC=C(F)C=C1 PLMOMLSRTDHBEA-UHFFFAOYSA-N 0.000 claims 1
- XMKVXVQEBWOGDB-UHFFFAOYSA-N n-[[3-(1h-indol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CC=CC(C=2C=C3C=CNC3=CC=2)=C1 XMKVXVQEBWOGDB-UHFFFAOYSA-N 0.000 claims 1
- BUPSNLWDMCEPMU-UHFFFAOYSA-N n-[[3-(1h-indol-5-yl)phenyl]methyl]-n-(2-pyrrolidin-1-ylethyl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N(CC=1C=C(C=CC=1)C=1C=C2C=CNC2=CC=1)CCN1CCCC1 BUPSNLWDMCEPMU-UHFFFAOYSA-N 0.000 claims 1
- WXHGDNBVTXGJQI-UHFFFAOYSA-N n-[[3-(1h-indol-5-yl)phenyl]methyl]-n-(3-pyrrolidin-1-ylpropyl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N(CC=1C=C(C=CC=1)C=1C=C2C=CNC2=CC=1)CCCN1CCCC1 WXHGDNBVTXGJQI-UHFFFAOYSA-N 0.000 claims 1
- CWLGPJRYTWNWLZ-UHFFFAOYSA-N n-[[4-(1h-indol-5-yl)furan-2-yl]methyl]-n-(2-pyrrolidin-1-ylethyl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N(CC=1OC=C(C=1)C=1C=C2C=CNC2=CC=1)CCN1CCCC1 CWLGPJRYTWNWLZ-UHFFFAOYSA-N 0.000 claims 1
- OVCJQDAKFFGOCX-UHFFFAOYSA-N n-[[4-(1h-indol-5-yl)furan-2-yl]methyl]-n-(3-pyrrolidin-1-ylpropyl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N(CC=1OC=C(C=1)C=1C=C2C=CNC2=CC=1)CCCN1CCCC1 OVCJQDAKFFGOCX-UHFFFAOYSA-N 0.000 claims 1
- AUZVTFKQFHYBDX-UHFFFAOYSA-N n-[[4-(1h-indol-5-yl)thiophen-2-yl]methyl]-n-(2-pyrrolidin-1-ylethyl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N(CC=1SC=C(C=1)C=1C=C2C=CNC2=CC=1)CCN1CCCC1 AUZVTFKQFHYBDX-UHFFFAOYSA-N 0.000 claims 1
- YZCCXNKYEHALHU-UHFFFAOYSA-N n-[[4-(1h-indol-5-yl)thiophen-2-yl]methyl]-n-(3-pyrrolidin-1-ylpropyl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N(CC=1SC=C(C=1)C=1C=C2C=CNC2=CC=1)CCCN1CCCC1 YZCCXNKYEHALHU-UHFFFAOYSA-N 0.000 claims 1
- PCFIHKBUEKEQGD-UHFFFAOYSA-N n-[[4-fluoro-3-(1h-indol-5-yl)phenyl]methyl]-n-(2-pyrrolidin-1-ylethyl)-4-(trifluoromethyl)benzamide Chemical compound C1=C(C=2C=C3C=CNC3=CC=2)C(F)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CCN1CCCC1 PCFIHKBUEKEQGD-UHFFFAOYSA-N 0.000 claims 1
- BPIPIBXGOHQVAI-UHFFFAOYSA-N n-[[5-(2,3-dihydro-1h-indol-5-yl)-2-fluorophenyl]methyl]-n-[2-(dimethylamino)ethyl]-4-fluorobenzamide Chemical compound C=1C(C=2C=C3CCNC3=CC=2)=CC=C(F)C=1CN(CCN(C)C)C(=O)C1=CC=C(F)C=C1 BPIPIBXGOHQVAI-UHFFFAOYSA-N 0.000 claims 1
- WSPPLTHLDDBMBV-UHFFFAOYSA-N n-[[5-(2h-benzotriazol-5-yl)-2-fluorophenyl]methyl]-4-fluoro-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC(C=2C=C3N=NNC3=CC=2)=CC=C1F WSPPLTHLDDBMBV-UHFFFAOYSA-N 0.000 claims 1
- KRBDRYLXOICLQH-UHFFFAOYSA-N n-[[5-(2h-benzotriazol-5-yl)-2-fluorophenyl]methyl]-4-fluoro-n-(1-propan-2-ylpiperidin-4-yl)benzamide Chemical compound C1CN(C(C)C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC(C=2C=C3N=NNC3=CC=2)=CC=C1F KRBDRYLXOICLQH-UHFFFAOYSA-N 0.000 claims 1
- IFPYUMUOSRWJPM-UHFFFAOYSA-N n-[[5-(2h-benzotriazol-5-yl)-2-fluorophenyl]methyl]-4-fluoro-n-piperidin-4-ylbenzamide Chemical compound C1=CC(F)=CC=C1C(=O)N(C1CCNCC1)CC1=CC(C=2C=C3N=NNC3=CC=2)=CC=C1F IFPYUMUOSRWJPM-UHFFFAOYSA-N 0.000 claims 1
- ZKLWBLVHYUYTIU-UHFFFAOYSA-N n-[[5-(2h-benzotriazol-5-yl)-2-fluorophenyl]methyl]-n-(1-cyclopropylpiperidin-4-yl)-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)N(C1CCN(CC1)C1CC1)CC1=CC(C=2C=C3N=NNC3=CC=2)=CC=C1F ZKLWBLVHYUYTIU-UHFFFAOYSA-N 0.000 claims 1
- SFIIUXLAGNDLGX-UHFFFAOYSA-N n-[[5-(2h-benzotriazol-5-yl)-2-fluorophenyl]methyl]-n-(thiophen-2-ylmethyl)piperidin-4-amine Chemical compound FC1=CC=C(C=2C=C3N=NNC3=CC=2)C=C1CN(C1CCNCC1)CC1=CC=CS1 SFIIUXLAGNDLGX-UHFFFAOYSA-N 0.000 claims 1
- MWBKYWAJVNXSPQ-UHFFFAOYSA-N n-[[5-(2h-benzotriazol-5-yl)-2-fluorophenyl]methyl]-n-[(4-fluorophenyl)methyl]piperidin-4-amine Chemical compound C1=CC(F)=CC=C1CN(C1CCNCC1)CC1=CC(C=2C=C3N=NNC3=CC=2)=CC=C1F MWBKYWAJVNXSPQ-UHFFFAOYSA-N 0.000 claims 1
- ZSZBDOJQRFGYBF-UHFFFAOYSA-N n-[[5-(3-cyano-1h-indol-5-yl)-2-fluorophenyl]methyl]-n-[2-(dimethylamino)ethyl]-4-fluorobenzamide Chemical compound C=1C(C=2C=C3C(C#N)=CNC3=CC=2)=CC=C(F)C=1CN(CCN(C)C)C(=O)C1=CC=C(F)C=C1 ZSZBDOJQRFGYBF-UHFFFAOYSA-N 0.000 claims 1
- 208000001797 obstructive sleep apnea Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 0 CC1(*2C1)NC1=C2*=CC(C)(*CO*(*)*)N=*1 Chemical compound CC1(*2C1)NC1=C2*=CC(C)(*CO*(*)*)N=*1 0.000 description 1
Classifications
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C07D239/72—Quinazolines; Hydrogenated quinazolines
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- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C07D277/62—Benzothiazoles
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65191105P | 2005-02-10 | 2005-02-10 | |
| US60/651,911 | 2005-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2007133655A true RU2007133655A (ru) | 2009-03-20 |
Family
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Family Applications (1)
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| RU2007133655/04A RU2007133655A (ru) | 2005-02-10 | 2006-02-10 | Замещенные бис-арильные и гетероарильные соединения в качестве селективных антагонистов 5нт2а |
Country Status (23)
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| US (1) | US7625889B2 (OSRAM) |
| EP (1) | EP1851199B1 (OSRAM) |
| JP (1) | JP5419355B2 (OSRAM) |
| KR (1) | KR20070107037A (OSRAM) |
| CN (1) | CN101115717A (OSRAM) |
| AR (1) | AR052903A1 (OSRAM) |
| AU (1) | AU2006213634A1 (OSRAM) |
| BR (1) | BRPI0606740A2 (OSRAM) |
| CA (1) | CA2598429A1 (OSRAM) |
| CR (1) | CR9260A (OSRAM) |
| DO (1) | DOP2006000032A (OSRAM) |
| GT (1) | GT200600042A (OSRAM) |
| IL (1) | IL185173A0 (OSRAM) |
| MA (1) | MA29289B1 (OSRAM) |
| MX (1) | MX2007008606A (OSRAM) |
| NO (1) | NO20074583L (OSRAM) |
| PA (1) | PA8662501A1 (OSRAM) |
| PE (1) | PE20061088A1 (OSRAM) |
| RU (1) | RU2007133655A (OSRAM) |
| TN (1) | TNSN07272A1 (OSRAM) |
| TW (1) | TW200640859A (OSRAM) |
| UY (1) | UY29372A1 (OSRAM) |
| WO (1) | WO2006086705A1 (OSRAM) |
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| RS20060035A (sr) | 2003-07-22 | 2008-08-07 | Arena Pharmaceuticals Inc., | Derivati diaril i arilheteroaril uree kao modulatori receptora 5-ht2a serotonina korisni u profilaksi i lečenju poremećaja u vezi sa njima |
| PE20061130A1 (es) | 2004-11-19 | 2007-01-05 | Arena Pharm Inc | Derivados de 3-fenil-pirazol como moduladores del receptor de serotonina 5-ht2a |
| MX2008001778A (es) | 2005-08-19 | 2008-04-07 | Aventis Pharma Inc | Combinacion de un agente hipnotico y un compuesto de bis arilo y heteroarilo sustituido y aplicacion terapeutica de la misma. |
| ES2462240T3 (es) * | 2006-02-28 | 2014-05-22 | Dart Neuroscience (Cayman) Ltd | Piperazinas terapéuticas como inhibidores de PDE4 |
| US8927546B2 (en) * | 2006-02-28 | 2015-01-06 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
| CA2648124A1 (en) | 2006-03-31 | 2007-11-08 | Schering Corporation | Kinase inhibitors |
| MX349156B (es) | 2006-05-18 | 2017-07-14 | Arena Pharm Inc | Formas cristalinas y procesos para la preparacion de fenil-pirazoles utiles como moduladores del receptor de serotonina 5-ht2a. |
| ES2536762T3 (es) | 2006-05-18 | 2015-05-28 | Arena Pharmaceuticals, Inc. | Aminas primarias y sus derivados como moduladores del receptor de la serotonina 5-HT2A útiles para el tratamiento de trastornos relacionados con este |
| CN101479261A (zh) | 2006-05-18 | 2009-07-08 | 艾尼纳制药公司 | 3-吡唑基-苯甲酰胺-4-醚、其仲胺及其衍生物作为5-ht2a血清素受体的调节剂用于治疗与其相关的病症 |
| TWI415845B (zh) | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與5-ht2a血清素受體相關聯病症之作為5-ht2a血清素受體之調節劑的吡唑衍生物 |
| EP2190844B3 (en) * | 2007-08-15 | 2013-07-17 | Arena Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| WO2009123714A2 (en) | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| WO2010045190A1 (en) | 2008-10-15 | 2010-04-22 | Boehringer Ingelheim International Gmbh | Fused heteroaryl diamide compounds useful as mmp-13 inhibitors |
| EP2340243B1 (en) | 2008-10-17 | 2014-10-08 | Boehringer Ingelheim International GmbH | Heteroaryl substituted indole compounds useful as mmp-13 inhibitors |
| RS57110B1 (sr) | 2008-10-28 | 2018-06-29 | Arena Pharm Inc | Sastavi modulatora 5-ht2a serotoninskog receptora korisni za tretiranje poremećaja povezanih sa njim |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| US8980891B2 (en) | 2009-12-18 | 2015-03-17 | Arena Pharmaceuticals, Inc. | Crystalline forms of certain 3-phenyl-pyrazole derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| WO2012151136A1 (en) * | 2011-05-03 | 2012-11-08 | Merck Sharp & Dohme Corp. | Aminomethyl biaryl benzotriazole derivatives |
| US11718643B2 (en) | 2012-11-13 | 2023-08-08 | Cytiva Bioprocess R&D Ab | Multimodal anion exchange matrices |
| US10464896B2 (en) | 2015-06-11 | 2019-11-05 | Basilea Pharmaceutica International AG | Efflux-pump inhibitors and therapeutic uses thereof |
| AU2016276966A1 (en) | 2015-06-12 | 2018-01-18 | Axovant Sciences Gmbh | Diaryl and arylheteroaryl urea derivatives useful for the prophylaxis and treatment of REM sleep behavior disorder |
| EP3322415A4 (en) | 2015-07-15 | 2019-03-13 | Axovant Sciences GmbH | DIARYL AND ARYLHETEROARYL UREA DERIVATIVES AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR FOR PROPHYLAXIS AND TREATMENT OF HALLUCINATIONS RELATED TO A NEUROGENERATIVE DISEASE |
| CN106854189A (zh) * | 2015-12-08 | 2017-06-16 | 湖南华腾制药有限公司 | 一种哌嗪化合物的合成方法 |
| CN107778257A (zh) * | 2016-08-29 | 2018-03-09 | 湖南华腾制药有限公司 | 一种哌嗪衍生物的合成方法 |
| CN106977463A (zh) * | 2017-05-31 | 2017-07-25 | 湖南华腾制药有限公司 | 一种联苯取代哌嗪衍生物的合成方法 |
| RS67273B1 (sr) | 2017-08-21 | 2025-10-31 | Acadia Pharm Inc | Jedinjenja, njihove soli i njihova upotreba u lečenju bolesti |
| WO2019040104A2 (en) * | 2017-08-21 | 2019-02-28 | Acadia Pharmaceuticals Inc. | COMPOUNDS, RELATED SALTS AND METHODS OF TREATING DISEASES |
| US12293809B2 (en) | 2019-08-23 | 2025-05-06 | Insilico Medicine Ip Limited | Workflow for generating compounds with biological activity against a specific biological target |
| WO2021038419A1 (en) * | 2019-08-23 | 2021-03-04 | Insilico Medicine Ip Limited | Kinase inhibitors and methods of synthesis and treatment |
| WO2022249113A1 (ko) * | 2021-05-25 | 2022-12-01 | 주식회사 자이메디 | Aimp2-dx2와 kras의 결합을 억제하는 신규 화합물 및 이의 용도 |
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| GB8305245D0 (en) * | 1983-02-25 | 1983-03-30 | Fujisawa Pharmaceutical Co | Imidazo-heterocyclic compounds |
| GB9114760D0 (en) * | 1991-07-09 | 1991-08-28 | Pfizer Ltd | Therapeutic agents |
| ATE247967T1 (de) * | 1998-06-09 | 2003-09-15 | Takeda Chemical Industries Ltd | Pharmazeutische kombination mit einem trizyclischen komponent und mindestens einem aus zolpidem, zopiclone und brotizolam, zur behandlung von schlafstörungen |
| ATE268766T1 (de) * | 1999-07-16 | 2004-06-15 | Bristol Myers Squibb Pharma Co | Stickstoff enthaltende heterobicyclen als factor xa inhibitoren |
| DE19934433A1 (de) * | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
| US6573049B1 (en) * | 1999-07-26 | 2003-06-03 | Nuvelo, Inc. | Genotyping of the paraoxonase 1 gene for prognosing, diagnosing, and treating a disease |
| YU54202A (sh) * | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| CA2436699A1 (en) * | 2000-12-21 | 2002-06-27 | Warner-Lambert Company Llc | Piperidine derivatives as subtype selective n-methyl-d-aspartate antagonists |
| DE10209520A1 (de) * | 2002-03-04 | 2003-09-25 | 4Sc Ag | Neue Modulatoren von Kaliumkanälen |
| ATE552253T1 (de) * | 2002-11-08 | 2012-04-15 | Novartis Int Pharm Ltd | 3-substituierte-6-aryl- pyridin derivate als liganden für c5a-rezeptoren |
| ES2502490T3 (es) * | 2003-02-26 | 2014-10-03 | Sugen, Inc. | Compuestos aminoheteroarílicos como inhibidores de proteín quinasas |
| JP4787150B2 (ja) * | 2003-03-06 | 2011-10-05 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Jnk阻害剤 |
| WO2005040131A1 (en) * | 2003-10-23 | 2005-05-06 | Akzo Nobel N.V. | 1,5,7-trisubstituted benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| US7632857B2 (en) * | 2004-04-01 | 2009-12-15 | Eli Lilly And Company | Histamine H3 receptor agents, preparation and therapeutic uses |
| US20060014733A1 (en) * | 2004-07-19 | 2006-01-19 | Pfizer Inc | Histamine-3 agonists and antagonists |
| JP2008508314A (ja) * | 2004-07-28 | 2008-03-21 | アイアールエム・リミテッド・ライアビリティ・カンパニー | ステロイドホルモン核内受容体のモジュレーターとしての化合物および組成物 |
-
2006
- 2006-02-06 GT GT200600042A patent/GT200600042A/es unknown
- 2006-02-07 DO DO2006000032A patent/DOP2006000032A/es unknown
- 2006-02-08 PE PE2006000149A patent/PE20061088A1/es not_active Application Discontinuation
- 2006-02-10 KR KR1020077018430A patent/KR20070107037A/ko not_active Withdrawn
- 2006-02-10 RU RU2007133655/04A patent/RU2007133655A/ru not_active Application Discontinuation
- 2006-02-10 WO PCT/US2006/004879 patent/WO2006086705A1/en not_active Ceased
- 2006-02-10 UY UY29372A patent/UY29372A1/es unknown
- 2006-02-10 TW TW095104456A patent/TW200640859A/zh unknown
- 2006-02-10 CN CNA200680004616XA patent/CN101115717A/zh active Pending
- 2006-02-10 BR BRPI0606740-9A patent/BRPI0606740A2/pt not_active Application Discontinuation
- 2006-02-10 EP EP06734836A patent/EP1851199B1/en active Active
- 2006-02-10 PA PA20068662501A patent/PA8662501A1/es unknown
- 2006-02-10 CA CA002598429A patent/CA2598429A1/en not_active Abandoned
- 2006-02-10 AU AU2006213634A patent/AU2006213634A1/en not_active Abandoned
- 2006-02-10 JP JP2007555276A patent/JP5419355B2/ja not_active Expired - Fee Related
- 2006-02-10 MX MX2007008606A patent/MX2007008606A/es not_active Application Discontinuation
- 2006-10-09 AR ARP060100467A patent/AR052903A1/es not_active Application Discontinuation
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2007
- 2007-07-13 TN TNP2007000272A patent/TNSN07272A1/en unknown
- 2007-07-19 CR CR9260A patent/CR9260A/es not_active Application Discontinuation
- 2007-07-25 US US11/782,923 patent/US7625889B2/en active Active
- 2007-08-09 IL IL185173A patent/IL185173A0/en unknown
- 2007-08-31 MA MA30191A patent/MA29289B1/fr unknown
- 2007-09-10 NO NO20074583A patent/NO20074583L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007008606A (es) | 2007-09-11 |
| TNSN07272A1 (en) | 2008-12-31 |
| PA8662501A1 (es) | 2006-09-08 |
| US20070265309A1 (en) | 2007-11-15 |
| UY29372A1 (es) | 2006-10-02 |
| EP1851199A1 (en) | 2007-11-07 |
| IL185173A0 (en) | 2007-12-03 |
| JP2008530120A (ja) | 2008-08-07 |
| PE20061088A1 (es) | 2006-11-29 |
| CA2598429A1 (en) | 2006-08-17 |
| JP5419355B2 (ja) | 2014-02-19 |
| CR9260A (es) | 2007-10-04 |
| DOP2006000032A (es) | 2006-08-15 |
| CN101115717A (zh) | 2008-01-30 |
| EP1851199B1 (en) | 2012-05-16 |
| AR052903A1 (es) | 2007-04-11 |
| US7625889B2 (en) | 2009-12-01 |
| GT200600042A (es) | 2006-09-27 |
| WO2006086705A1 (en) | 2006-08-17 |
| TW200640859A (en) | 2006-12-01 |
| NO20074583L (no) | 2007-10-12 |
| WO2006086705B1 (en) | 2006-11-16 |
| AU2006213634A1 (en) | 2006-08-17 |
| MA29289B1 (fr) | 2008-02-01 |
| KR20070107037A (ko) | 2007-11-06 |
| BRPI0606740A2 (pt) | 2009-07-14 |
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