JP2008530120A5 - - Google Patents
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- Publication number
- JP2008530120A5 JP2008530120A5 JP2007555276A JP2007555276A JP2008530120A5 JP 2008530120 A5 JP2008530120 A5 JP 2008530120A5 JP 2007555276 A JP2007555276 A JP 2007555276A JP 2007555276 A JP2007555276 A JP 2007555276A JP 2008530120 A5 JP2008530120 A5 JP 2008530120A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- benzyl
- methyl
- ylmethyl
- indol
- 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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- -1 thiophenylcarbonyl Chemical group 0.000 claims 185
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000001544 thienyl group Chemical group 0.000 claims 19
- 125000002541 furyl group Chemical group 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
- 125000004076 pyridyl group Chemical group 0.000 claims 18
- 125000001207 fluorophenyl group Chemical group 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 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
- 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 group 0.000 claims 10
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000006333 difluoro benzoyl group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 208000019116 sleep disease Diseases 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 3
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 3
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- 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 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 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 group 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
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- JWZQJTGQFHIRFQ-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6-carboxylic acid Chemical compound O1CCOC2=CC(C(=O)O)=CC=C21 JWZQJTGQFHIRFQ-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
- YFQFIPQQCGDESN-UHFFFAOYSA-N 4-chloro-n-[2-(dimethylamino)ethyl]-n-[[3-(2-oxo-3h-1,3-benzothiazol-6-yl)phenyl]methyl]benzamide;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3SC(=O)NC3=CC=2)=CC=1CN(CCN(C)C)C(=O)C1=CC=C(Cl)C=C1 YFQFIPQQCGDESN-UHFFFAOYSA-N 0.000 claims 1
- DFSFDJWPILSHHC-UHFFFAOYSA-N 4-chloro-n-[2-(dimethylamino)ethyl]-n-[[3-(2-oxo-3h-1,3-benzoxazol-6-yl)phenyl]methyl]benzamide;hydrochloride Chemical compound Cl.C=1C=CC(C=2C=C3OC(=O)NC3=CC=2)=CC=1CN(CCN(C)C)C(=O)C1=CC=C(Cl)C=C1 DFSFDJWPILSHHC-UHFFFAOYSA-N 0.000 claims 1
- ITEOLDGOKAKQIM-UHFFFAOYSA-N 4-chloro-n-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(Cl)=CC=1)CC1=CC(C=2C=C3C=CNC3=CC=2)=CC=C1F ITEOLDGOKAKQIM-UHFFFAOYSA-N 0.000 claims 1
- HTCWMWGQTZLIIX-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-indazol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-3-yl)benzamide Chemical compound C1N(C)CCCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC(C=2C=C3C=NNC3=CC=2)=CC=C1F HTCWMWGQTZLIIX-UHFFFAOYSA-N 0.000 claims 1
- BHRCOVLBWBPNGM-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-indazol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC(C=2C=C3C=NNC3=CC=2)=CC=C1F BHRCOVLBWBPNGM-UHFFFAOYSA-N 0.000 claims 1
- ZTIJZNIXULPFNV-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-indazol-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=NNC2=CC=1)F)CCN1CCCC1 ZTIJZNIXULPFNV-UHFFFAOYSA-N 0.000 claims 1
- UVNXSNUUONIEKA-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-indazol-5-yl)phenyl]methyl]-n-(3-pyrrolidin-1-ylpropyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N(CC=1C(=CC=C(C=1)C=1C=C2C=NNC2=CC=1)F)CCCN1CCCC1 UVNXSNUUONIEKA-UHFFFAOYSA-N 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
- YARYXWNULHXGCT-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-indol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC(C=2C=C3C=CNC3=CC=2)=CC=C1F YARYXWNULHXGCT-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
- UWLSAXUNLOGZKG-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(1h-pyrrolo[3,2-b]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=C2C=CNC2=CC=1)F)CCN1CCCC1 UWLSAXUNLOGZKG-UHFFFAOYSA-N 0.000 claims 1
- MMLOGCJLVYBGMT-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(2-oxo-3h-1,3-benzoxazol-6-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC(C=2C=C3OC(=O)NC3=CC=2)=CC=C1F MMLOGCJLVYBGMT-UHFFFAOYSA-N 0.000 claims 1
- VXJWXSCPMIQSMI-UHFFFAOYSA-N 4-fluoro-n-[[2-fluoro-5-(2-oxo-3h-1,3-benzoxazol-6-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=C2OC(=O)NC2=CC=1)F)CCN1CCCC1 VXJWXSCPMIQSMI-UHFFFAOYSA-N 0.000 claims 1
- XJNQGSDHNHZIJS-UHFFFAOYSA-N 4-fluoro-n-[[3-(1h-indol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC=CC(C=2C=C3C=CNC3=CC=2)=C1 XJNQGSDHNHZIJS-UHFFFAOYSA-N 0.000 claims 1
- NASREVVWFJQBIN-UHFFFAOYSA-N 4-fluoro-n-[[3-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=C(C=C(F)C=1)C=1C=C2C=CNC2=CC=1)CCN1CCCC1 NASREVVWFJQBIN-UHFFFAOYSA-N 0.000 claims 1
- YEGQCJSXNDCXJQ-UHFFFAOYSA-N 4-fluoro-n-[[4-(1h-indazol-5-yl)furan-2-yl]methyl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC(C=2C=C3C=NNC3=CC=2)=CO1 YEGQCJSXNDCXJQ-UHFFFAOYSA-N 0.000 claims 1
- FRHCJJWSMXDBKW-UHFFFAOYSA-N 4-fluoro-n-[[4-(1h-indol-5-yl)furan-2-yl]methyl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC(C=2C=C3C=CNC3=CC=2)=CO1 FRHCJJWSMXDBKW-UHFFFAOYSA-N 0.000 claims 1
- TXPJMHQDCBOKKE-UHFFFAOYSA-N 4-fluoro-n-[[4-fluoro-3-(1h-indol-5-yl)phenyl]methyl]-n-(1-methylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1N(C(=O)C=1C=CC(F)=CC=1)CC1=CC=C(F)C(C=2C=C3C=CNC3=CC=2)=C1 TXPJMHQDCBOKKE-UHFFFAOYSA-N 0.000 claims 1
- XTAMTJXBUKKGSM-UHFFFAOYSA-N 4-fluoro-n-[[5-(1h-indol-5-yl)pyridin-3-yl]methyl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N(CC=1C=C(C=NC=1)C=1C=C2C=CNC2=CC=1)CCN1CCCC1 XTAMTJXBUKKGSM-UHFFFAOYSA-N 0.000 claims 1
- YYNCJJLOAKQESC-UHFFFAOYSA-N 4-fluoro-n-[[5-(1h-indol-5-yl)thiophen-2-yl]methyl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N(CC=1SC(=CC=1)C=1C=C2C=CNC2=CC=1)CCN1CCCC1 YYNCJJLOAKQESC-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
- UIHVZHGNGWCBFR-UHFFFAOYSA-N 5-[3-[[2-(dimethylamino)ethyl-[(4-fluorophenyl)methyl]amino]methyl]-4-fluorophenyl]-1h-indole-3-carbonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C(C=2C=C3C(C#N)=CNC3=CC=2)=CC=C(F)C=1CN(CCN(C)C)CC1=CC=C(F)C=C1 UIHVZHGNGWCBFR-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
- QCPQMQBXFGUSQZ-NRFANRHFSA-N 6-[5-[[(2r)-2-(4-fluorophenyl)-4-methylpiperazin-1-yl]methyl]furan-3-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1([C@H]2N(CC=3OC=C(C=3)C=3C=C4OC(=O)NC4=CC=3)CCN(C2)C)=CC=C(F)C=C1 QCPQMQBXFGUSQZ-NRFANRHFSA-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
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| US9139576B2 (en) | 2011-05-03 | 2015-09-22 | Merck Sharp & Dohme Corp. | Aminomethyl biaryl benzotriazole derivatives |
| CN104797332B (zh) | 2012-11-13 | 2018-05-29 | 通用电气医疗集团生物工艺研发股份公司 | 多元阴离子交换基质 |
| CN107709314A (zh) | 2015-06-11 | 2018-02-16 | 巴斯利尔药物国际股份公司 | 外排泵抑制剂及其治疗性用途 |
| JP2018516992A (ja) | 2015-06-12 | 2018-06-28 | アクソファント サイエンシーズ ゲーエムベーハーＡｘｏｖａｎｔ Ｓｃｉｅｎｃｅｓ Ｇｍｂｈ | レム睡眠行動障害の予防および処置のために有用なジアリールおよびアリールヘテロアリール尿素誘導体 |
| CN108472285A (zh) | 2015-07-15 | 2018-08-31 | 阿速万科学有限责任公司 | 用于预防和治疗与神经退行性疾病相关联的幻觉的二芳基和芳基杂芳基脲衍生物 |
| 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 |
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| 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 |
| US6348485B1 (en) * | 1998-06-09 | 2002-02-19 | Takeda Chemical Industries, Ltd. | Method for treating or preventing sleep disorders |
| MXPA02000537A (es) * | 1999-07-16 | 2004-09-10 | Bristol Myers Squibb Pharma Co | Heterobiciclos que contienen nitrogeno como inhibidores del factor xa. |
| 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 |
| AU2002223968A1 (en) * | 2000-12-21 | 2002-07-01 | 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 |
| AU2003291403A1 (en) * | 2002-11-08 | 2004-06-03 | Neurogen Corporation | 3-substituted-6-aryl pyridined as ligands of c5a receptors |
| PT2476667E (pt) * | 2003-02-26 | 2014-09-18 | Sugen Inc | Compostos de aminoheteroarilo como inibidores da proteína quinase |
| US7432375B2 (en) * | 2003-03-06 | 2008-10-07 | Eisai R & D Management Co., Ltd. | JNK inhibitors |
| EP1678144A1 (en) * | 2003-10-23 | 2006-07-12 | Akzo Nobel N.V. | 1,5,7-TRISUBSTITUTED BENZIMIDAZOLE DERIVATIVES AND THEIR USE FOR MODULATING THE GABA-a RECEPTOR COMPLEX |
| CA2561628C (en) * | 2004-04-01 | 2012-05-08 | 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 |
| RU2007107177A (ru) * | 2004-07-28 | 2008-09-10 | Айрм Ллк (Bm) | Соединения и композиции, как модуляторы ядерных рецепторов стероидных гормонов |
-
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 TW TW095104456A patent/TW200640859A/zh unknown
- 2006-02-10 WO PCT/US2006/004879 patent/WO2006086705A1/en not_active Ceased
- 2006-02-10 CA CA002598429A patent/CA2598429A1/en not_active Abandoned
- 2006-02-10 RU RU2007133655/04A patent/RU2007133655A/ru not_active Application Discontinuation
- 2006-02-10 CN CNA200680004616XA patent/CN101115717A/zh active Pending
- 2006-02-10 KR KR1020077018430A patent/KR20070107037A/ko not_active Withdrawn
- 2006-02-10 EP EP06734836A patent/EP1851199B1/en not_active Expired - Lifetime
- 2006-02-10 PA PA20068662501A patent/PA8662501A1/es unknown
- 2006-02-10 UY UY29372A patent/UY29372A1/es unknown
- 2006-02-10 BR BRPI0606740-9A patent/BRPI0606740A2/pt not_active Application Discontinuation
- 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
- 2006-02-10 AU AU2006213634A patent/AU2006213634A1/en not_active Abandoned
- 2006-10-09 AR ARP060100467A patent/AR052903A1/es not_active Application Discontinuation
-
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 not_active Expired - Lifetime
- 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
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