JP2010518026A5 - - Google Patents
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- JP2010518026A5 JP2010518026A5 JP2009548501A JP2009548501A JP2010518026A5 JP 2010518026 A5 JP2010518026 A5 JP 2010518026A5 JP 2009548501 A JP2009548501 A JP 2009548501A JP 2009548501 A JP2009548501 A JP 2009548501A JP 2010518026 A5 JP2010518026 A5 JP 2010518026A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- heteroaryl
- heterocyclyl
- haloalkyl
- aryl
- 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.)
- Withdrawn
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- 125000000217 alkyl group Chemical group 0.000 claims description 228
- 125000001188 haloalkyl group Chemical group 0.000 claims description 228
- 125000001072 heteroaryl group Chemical group 0.000 claims description 227
- 125000000623 heterocyclic group Chemical group 0.000 claims description 226
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 218
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 212
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 202
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 201
- 229910052739 hydrogen Inorganic materials 0.000 claims description 156
- 239000001257 hydrogen Substances 0.000 claims description 156
- 150000002431 hydrogen Chemical class 0.000 claims description 152
- 125000003342 alkenyl group Chemical group 0.000 claims description 140
- 125000003118 aryl group Chemical group 0.000 claims description 138
- 125000000304 alkynyl group Chemical group 0.000 claims description 126
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 121
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 108
- 125000001475 halogen functional group Chemical group 0.000 claims description 104
- 125000002947 alkylene group Chemical group 0.000 claims description 100
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 100
- 125000003107 substituted aryl group Chemical group 0.000 claims description 96
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 90
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 90
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 90
- -1 heterocyclylalkynyl Chemical group 0.000 claims description 90
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 78
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 72
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 72
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 54
- 125000004450 alkenylene group Chemical group 0.000 claims description 36
- 125000004419 alkynylene group Chemical group 0.000 claims description 36
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 29
- 208000002193 Pain Diseases 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 19
- 239000000651 prodrug Substances 0.000 claims description 19
- 229940002612 prodrug Drugs 0.000 claims description 19
- 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 description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 4
- GQTHJKCHZISVJO-UHFFFAOYSA-N 3-[4-(2-butyl-4-oxopyrido[1,2-a]pyrimidin-3-yl)anilino]pyrrolidine-1-carboxylic acid Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC1CCN(C(O)=O)C1 GQTHJKCHZISVJO-UHFFFAOYSA-N 0.000 claims description 4
- 206010019233 Headaches Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 210000005036 nerve Anatomy 0.000 claims description 4
- 210000000578 peripheral nerve Anatomy 0.000 claims description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 230000001256 tonic effect Effects 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 108010052164 Sodium Channels Proteins 0.000 claims description 3
- 102000018674 Sodium Channels Human genes 0.000 claims description 3
- 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 claims description 3
- 108010053752 Voltage-Gated Sodium Channels Proteins 0.000 claims description 3
- 210000004962 mammalian cell Anatomy 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- BDNGJSYVQWBMMY-LJQANCHMSA-N 2-(2-cyclopropylethyl)-3-[4-[[(3r)-pyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound N1=C2C=CC=CN2C(=O)C(C=2C=CC(N[C@H]3CNCC3)=CC=2)=C1CCC1CC1 BDNGJSYVQWBMMY-LJQANCHMSA-N 0.000 claims description 2
- CGRSWHYBXCGJKQ-LJQANCHMSA-N 2-(3-methylbutyl)-3-[4-[[(3r)-pyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)CCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCNC1 CGRSWHYBXCGJKQ-LJQANCHMSA-N 0.000 claims description 2
- UGULKPLSXNNWLT-UHFFFAOYSA-N 2-(propan-2-ylamino)-3-[4-(pyrrolidin-3-ylamino)phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)NC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC1CCNC1 UGULKPLSXNNWLT-UHFFFAOYSA-N 0.000 claims description 2
- UGULKPLSXNNWLT-QGZVFWFLSA-N 2-(propan-2-ylamino)-3-[4-[[(3r)-pyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CC(C)NC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCNC1 UGULKPLSXNNWLT-QGZVFWFLSA-N 0.000 claims description 2
- MEWSBWPKBQRBSI-UHFFFAOYSA-N 2-(propylamino)-3-[4-(pyrrolidin-3-ylamino)phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCNC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC1CCNC1 MEWSBWPKBQRBSI-UHFFFAOYSA-N 0.000 claims description 2
- OHEBENJHYVXWQU-UHFFFAOYSA-N 2-[[4-(2-butyl-4-oxopyrido[1,2-a]pyrimidin-3-yl)phenyl]carbamoyl]pyrrolidine-1-carboxylic acid Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC(=O)C1CCCN1C(O)=O OHEBENJHYVXWQU-UHFFFAOYSA-N 0.000 claims description 2
- WILSLAKCHWCKBA-UHFFFAOYSA-N 2-butyl-3-(1-pyrrolidin-3-yl-2,3-dihydroindol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1CC2)=CC=C1N2C1CCNC1 WILSLAKCHWCKBA-UHFFFAOYSA-N 0.000 claims description 2
- LZGWVSQVIMHLMP-UHFFFAOYSA-N 2-butyl-3-(1h-indol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2NC=CC2=CC(C=2C(=O)N3C=CC=CC3=NC=2CCCC)=C1 LZGWVSQVIMHLMP-UHFFFAOYSA-N 0.000 claims description 2
- PBJYXCASMFAEIC-UHFFFAOYSA-N 2-butyl-3-(2,3-dihydro-1h-indol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2NCCC2=CC(C=2C(=O)N3C=CC=CC3=NC=2CCCC)=C1 PBJYXCASMFAEIC-UHFFFAOYSA-N 0.000 claims description 2
- FTAAYXQDBYHHAI-UHFFFAOYSA-N 2-butyl-3-(2-chlorophenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=CC=C1Cl FTAAYXQDBYHHAI-UHFFFAOYSA-N 0.000 claims description 2
- YRLFNLXYTSJOOE-UHFFFAOYSA-N 2-butyl-3-(3-chloro-4-methoxyphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(OC)C(Cl)=C1 YRLFNLXYTSJOOE-UHFFFAOYSA-N 0.000 claims description 2
- UFANQXDTXYHRHA-UHFFFAOYSA-N 2-butyl-3-(3-chlorophenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=CC(Cl)=C1 UFANQXDTXYHRHA-UHFFFAOYSA-N 0.000 claims description 2
- OMEVOAPWXAAPAA-UHFFFAOYSA-N 2-butyl-3-(4-chloro-2-methylphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(Cl)C=C1C OMEVOAPWXAAPAA-UHFFFAOYSA-N 0.000 claims description 2
- AXZGRDUIRBJSFW-UHFFFAOYSA-N 2-butyl-3-(4-chloro-3-fluorophenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(Cl)C(F)=C1 AXZGRDUIRBJSFW-UHFFFAOYSA-N 0.000 claims description 2
- HEQFGZGSYXGNRC-UHFFFAOYSA-N 2-butyl-3-(4-chloro-3-methylphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(Cl)C(C)=C1 HEQFGZGSYXGNRC-UHFFFAOYSA-N 0.000 claims description 2
- WJINBXRGUDWNAD-UHFFFAOYSA-N 2-butyl-3-(4-chlorophenyl)-7-fluoropyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC(F)=CN2C(=O)C=1C1=CC=C(Cl)C=C1 WJINBXRGUDWNAD-UHFFFAOYSA-N 0.000 claims description 2
- GZLWCMCIQCGIBW-UHFFFAOYSA-N 2-butyl-3-(4-chlorophenyl)-7-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC(C)=CN2C(=O)C=1C1=CC=C(Cl)C=C1 GZLWCMCIQCGIBW-UHFFFAOYSA-N 0.000 claims description 2
- YTBASMOHBHHWDW-UHFFFAOYSA-N 2-butyl-3-(4-chlorophenyl)-8-(trifluoromethyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=C(C(F)(F)F)C=CN2C(=O)C=1C1=CC=C(Cl)C=C1 YTBASMOHBHHWDW-UHFFFAOYSA-N 0.000 claims description 2
- KGTOIPOLSLXEJA-UHFFFAOYSA-N 2-butyl-3-(4-chlorophenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(Cl)C=C1 KGTOIPOLSLXEJA-UHFFFAOYSA-N 0.000 claims description 2
- YVSWUEUANBKTRA-UHFFFAOYSA-N 2-butyl-3-(4-chlorophenyl)pyrimido[2,1-a]isoquinolin-4-one Chemical compound CCCCC=1N=C2C3=CC=CC=C3C=CN2C(=O)C=1C1=CC=C(Cl)C=C1 YVSWUEUANBKTRA-UHFFFAOYSA-N 0.000 claims description 2
- NDKPIIGWKYOUTI-UHFFFAOYSA-N 2-butyl-3-(4-hydroxyphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(O)C=C1 NDKPIIGWKYOUTI-UHFFFAOYSA-N 0.000 claims description 2
- XAHBUOXGWYENNJ-UHFFFAOYSA-N 2-butyl-3-(4-methoxyphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(OC)C=C1 XAHBUOXGWYENNJ-UHFFFAOYSA-N 0.000 claims description 2
- DHYAFPKQKHKPES-UHFFFAOYSA-N 2-butyl-3-(4-morpholin-4-ylphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N1CCOCC1 DHYAFPKQKHKPES-UHFFFAOYSA-N 0.000 claims description 2
- UUJWGBLOQFFVFN-UHFFFAOYSA-N 2-butyl-3-(6-chloropyridin-3-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(Cl)N=C1 UUJWGBLOQFFVFN-UHFFFAOYSA-N 0.000 claims description 2
- WEWHNKFNEFBMSV-UHFFFAOYSA-N 2-butyl-3-(6-piperazin-1-ylpyridin-3-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=N1)=CC=C1N1CCNCC1 WEWHNKFNEFBMSV-UHFFFAOYSA-N 0.000 claims description 2
- VPCREMHCSDZXBF-GOSISDBHSA-N 2-butyl-3-[2-methyl-4-[[(3r)-pyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C(=C1)C)=CC=C1N[C@@H]1CCNC1 VPCREMHCSDZXBF-GOSISDBHSA-N 0.000 claims description 2
- HZEUEQMTNNCZHI-UHFFFAOYSA-N 2-butyl-3-[3-(pyrrolidin-3-ylamino)phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=1)=CC=CC=1NC1CCNC1 HZEUEQMTNNCZHI-UHFFFAOYSA-N 0.000 claims description 2
- OYMFFFAKPOXNIA-UHFFFAOYSA-N 2-butyl-3-[4-(oxan-4-ylamino)phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC1CCOCC1 OYMFFFAKPOXNIA-UHFFFAOYSA-N 0.000 claims description 2
- VRWTUXADFWUGHR-UHFFFAOYSA-N 2-butyl-3-[4-(piperidin-3-ylamino)phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC1CCCNC1 VRWTUXADFWUGHR-UHFFFAOYSA-N 0.000 claims description 2
- DRFOQORPLGCOSD-UHFFFAOYSA-N 2-butyl-3-[4-(piperidin-4-ylamino)phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC1CCNCC1 DRFOQORPLGCOSD-UHFFFAOYSA-N 0.000 claims description 2
- XQDNVUXVLJSPQO-UHFFFAOYSA-N 2-butyl-3-[4-(pyrrolidin-3-ylamino)phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC1CCNC1 XQDNVUXVLJSPQO-UHFFFAOYSA-N 0.000 claims description 2
- MOOYRGXNSSBKMI-GOSISDBHSA-N 2-butyl-3-[4-[(3r)-pyrrolidin-3-yl]oxyphenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1O[C@@H]1CCNC1 MOOYRGXNSSBKMI-GOSISDBHSA-N 0.000 claims description 2
- YQVMONANQKRRNN-LJQANCHMSA-N 2-butyl-3-[4-[[(2r)-oxolan-2-yl]methylamino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC[C@H]1CCCO1 YQVMONANQKRRNN-LJQANCHMSA-N 0.000 claims description 2
- YQVMONANQKRRNN-IBGZPJMESA-N 2-butyl-3-[4-[[(2s)-oxolan-2-yl]methylamino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1NC[C@@H]1CCCO1 YQVMONANQKRRNN-IBGZPJMESA-N 0.000 claims description 2
- LFZITLDVTCNZHL-LJQANCHMSA-N 2-butyl-3-[4-[[(3r)-1-methylpyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCN(C)C1 LFZITLDVTCNZHL-LJQANCHMSA-N 0.000 claims description 2
- MSVAZTNPMCRPJD-GMUIIQOCSA-N 2-butyl-3-[4-[[(3r)-oxolan-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one;hydrochloride Chemical compound Cl.CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCOC1 MSVAZTNPMCRPJD-GMUIIQOCSA-N 0.000 claims description 2
- VRWTUXADFWUGHR-LJQANCHMSA-N 2-butyl-3-[4-[[(3r)-piperidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCCNC1 VRWTUXADFWUGHR-LJQANCHMSA-N 0.000 claims description 2
- ZKXJCNSOTJAVJK-GOSISDBHSA-N 2-butyl-3-[4-[[(3r)-pyrrolidin-3-yl]amino]phenyl]-8-(trifluoromethyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=C(C(F)(F)F)C=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCNC1 ZKXJCNSOTJAVJK-GOSISDBHSA-N 0.000 claims description 2
- XQDNVUXVLJSPQO-GOSISDBHSA-N 2-butyl-3-[4-[[(3r)-pyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCNC1 XQDNVUXVLJSPQO-GOSISDBHSA-N 0.000 claims description 2
- DMGZGGQSZWVQDP-OAQYLSRUSA-N 2-butyl-3-[4-[[(3r)-pyrrolidin-3-yl]amino]phenyl]pyrimido[2,1-a]isoquinolin-4-one Chemical compound CCCCC=1N=C2C3=CC=CC=C3C=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCNC1 DMGZGGQSZWVQDP-OAQYLSRUSA-N 0.000 claims description 2
- XQDNVUXVLJSPQO-SFHVURJKSA-N 2-butyl-3-[4-[[(3s)-pyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N[C@H]1CCNC1 XQDNVUXVLJSPQO-SFHVURJKSA-N 0.000 claims description 2
- AOCDPQJHJRDOIP-HXUWFJFHSA-N 2-butyl-3-[4-[methyl-[(3r)-1-methylpyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C(C=C1)=CC=C1N(C)[C@@H]1CCN(C)C1 AOCDPQJHJRDOIP-HXUWFJFHSA-N 0.000 claims description 2
- YVCXJLUADGVPCO-UHFFFAOYSA-N 2-butyl-3-[4-chloro-3-(trifluoromethyl)phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(Cl)C(C(F)(F)F)=C1 YVCXJLUADGVPCO-UHFFFAOYSA-N 0.000 claims description 2
- UUFSNKDLAKYBCK-UHFFFAOYSA-N 2-butyl-7-chloro-3-(4-hydroxyphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC(Cl)=CN2C(=O)C=1C1=CC=C(O)C=C1 UUFSNKDLAKYBCK-UHFFFAOYSA-N 0.000 claims description 2
- OAYCSEAHQYXYTQ-UHFFFAOYSA-N 2-butyl-7-chloro-3-(4-methoxyphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC(Cl)=CN2C(=O)C=1C1=CC=C(OC)C=C1 OAYCSEAHQYXYTQ-UHFFFAOYSA-N 0.000 claims description 2
- DUNNCDGYFQXOOO-GOSISDBHSA-N 2-butyl-7-fluoro-3-[4-[[(3r)-pyrrolidin-3-yl]amino]phenyl]pyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC(F)=CN2C(=O)C=1C(C=C1)=CC=C1N[C@@H]1CCNC1 DUNNCDGYFQXOOO-GOSISDBHSA-N 0.000 claims description 2
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| CN104945420A (zh) | 2009-06-29 | 2015-09-30 | 因塞特公司 | 作为pi3k抑制剂的嘧啶酮类 |
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| EP2655374B1 (en) | 2010-12-20 | 2019-10-23 | Incyte Holdings Corporation | N-(1-(substituted-phenyl)ethyl)-9h-purin-6-amines as pi3k inhibitors |
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| KR102507287B1 (ko) | 2011-09-02 | 2023-03-07 | 인사이트 홀딩스 코포레이션 | Ｐｉ３ｋ 억제제로서 헤테로시클릴아민 |
| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドＸｅｎｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| RU2014121984A (ru) | 2011-10-31 | 2015-12-10 | Ксенон Фармасьютикалз Инк. | Бензолсульфонамидные соединения и их применение в качестве терапевтических средств |
| WO2013115884A2 (en) * | 2011-11-15 | 2013-08-08 | Trustees Of Boston University | Pyridopyrimidinone inhibitors of viruses |
| WO2013136170A1 (en) | 2012-03-16 | 2013-09-19 | Purdue Pharma L.P. | Substituted pyridines as sodium channel blockers |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| CN104718188B (zh) | 2012-05-22 | 2018-08-21 | 基因泰克公司 | N-取代的苯甲酰胺类及其在治疗疼痛中的用途 |
| KR101663436B1 (ko) * | 2012-07-06 | 2016-10-06 | 제넨테크, 인크. | N-치환된 벤즈아미드 및 이의 사용 방법 |
| WO2014096941A1 (en) | 2012-12-20 | 2014-06-26 | Purdue Pharma L.P. | Cyclic sulfonamides as sodium channel blockers |
| RU2015143906A (ru) | 2013-03-14 | 2017-04-18 | Дженентек, Инк. | Замещенные триазолопиридины и способы их применения |
| BR112015023397A2 (pt) | 2013-03-15 | 2017-07-18 | Genentech Inc | benzoxazois substituídos e métodos de uso dos mesmos |
| UA120353C2 (uk) * | 2013-09-10 | 2019-11-25 | Хромоселл Корпорейшн | Модулятори натрієвого каналу для лікування болю і діабету |
| WO2015078374A1 (en) | 2013-11-27 | 2015-06-04 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| US10730866B2 (en) | 2014-04-07 | 2020-08-04 | Purdue Pharma L.P. | Indole derivatives and use thereof |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| JP2017525677A (ja) | 2014-07-07 | 2017-09-07 | ジェネンテック， インコーポレイテッド | 治療用化合物及びその使用方法 |
| SI3831833T1 (sl) | 2015-02-27 | 2023-03-31 | Incyte Holdings Corporation | Postopki za pripravo inhibitorja PI3K |
| EP3283487B1 (en) * | 2015-04-15 | 2019-10-16 | H. Hoffnabb-La Roche Ag | Pyridopyrimidinones and their use as nmda receptor modulators |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| HK1252567A1 (zh) | 2015-05-22 | 2019-05-31 | 基因泰克公司 | 被取代的苯甲酰胺和其使用方法 |
| EA201890086A1 (ru) * | 2015-06-18 | 2018-06-29 | Сефалон, Инк. | 1,4-замещенные производные пиперидина |
| ES2849951T3 (es) | 2015-06-18 | 2021-08-24 | 89Bio Ltd | Derivados de piperidina 4-bencil y 4-benzoil sustituidos |
| JP2018526371A (ja) | 2015-08-27 | 2018-09-13 | ジェネンテック， インコーポレイテッド | 治療化合物及びその使用方法 |
| CA2999769A1 (en) | 2015-09-28 | 2017-04-06 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| EP3380466A1 (en) | 2015-11-25 | 2018-10-03 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3436432B1 (en) | 2016-03-30 | 2021-01-27 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| PE20190980A1 (es) | 2016-10-17 | 2019-07-09 | Genentech Inc | Compuestos terapeuticos y metodos para utilizarlos |
| JP2020511511A (ja) | 2017-03-24 | 2020-04-16 | ジェネンテック， インコーポレイテッド | ナトリウムチャネル阻害剤としての４−ピペリジン−ｎ−（ピリミジン−４−イル）クロマン−７−スルホンアミド誘導体 |
| AR114263A1 (es) | 2018-02-26 | 2020-08-12 | Genentech Inc | Compuestos terapéuticos y métodos para utilizarlos |
| US10947251B2 (en) | 2018-03-30 | 2021-03-16 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| CA3101323A1 (en) | 2018-06-01 | 2019-12-05 | Incyte Corporation | Dosing regimen for the treatment of pi3k related disorders |
| WO2019236694A1 (en) * | 2018-06-05 | 2019-12-12 | Incarda Therapeutics, Inc. | Methods for diagnosing brugada syndrome using an aerosol |
| JP7638987B2 (ja) * | 2019-11-25 | 2025-03-04 | アムジエン・インコーポレーテツド | デルタ－５デサチュラーゼ阻害剤としての複素環式化合物、及び使用法 |
| CN110818709B (zh) * | 2019-11-28 | 2022-09-02 | 成都大学 | 一种co2参与下合成嘧啶酮类化合物的方法 |
| CN113292557B (zh) * | 2021-05-31 | 2022-02-11 | 贵州大学 | 一种含吲哚单元的吡啶并嘧啶酮类介离子衍生物及其制备方法和用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63112566A (ja) * | 1986-10-28 | 1988-05-17 | Nissan Chem Ind Ltd | ピリミジノン誘導体、その製法および殺虫・殺ダニ・殺菌剤 |
| EP1677799A4 (en) * | 2003-10-21 | 2008-09-10 | Merck & Co Inc | TRIAZOLO-PYRIDAZINE COMPOUNDS AND DERIVATIVES THEREOF FOR THE TREATMENT OF NEUROPATHIC PAIN |
| AR053713A1 (es) * | 2005-04-20 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos heterociclicos y sus usos como agentes terapeuticos |
| CA2612585A1 (en) * | 2005-06-27 | 2007-01-04 | Amgen Inc. | Anti-inflammatory aryl nitrile compounds |
| CA2622639C (en) * | 2005-10-04 | 2012-01-03 | Istituto Di Recerche Di Biologia Molecolare P. Angeletti S.P.A. | Hiv integrase inhibitors |
| EP1818058A3 (en) * | 2006-02-13 | 2007-11-07 | Astion Pharma A/S | Treatment of mmp-mediated dermatological diseases with pemirolast |
-
2008
- 2008-02-05 AR ARP080100493A patent/AR065194A1/es unknown
- 2008-02-05 TW TW097104675A patent/TW200838539A/zh unknown
- 2008-02-05 AU AU2008213836A patent/AU2008213836A1/en not_active Abandoned
- 2008-02-05 US US12/026,435 patent/US20080194616A1/en not_active Abandoned
- 2008-02-05 RU RU2009133336/04A patent/RU2009133336A/ru unknown
- 2008-02-05 BR BRPI0807351-1A patent/BRPI0807351A2/pt not_active IP Right Cessation
- 2008-02-05 WO PCT/US2008/053075 patent/WO2008097991A1/en not_active Ceased
- 2008-02-05 CL CL200800369A patent/CL2008000369A1/es unknown
- 2008-02-05 EP EP08729067A patent/EP2079737A1/en not_active Withdrawn
- 2008-02-05 CA CA002677493A patent/CA2677493A1/en not_active Abandoned
- 2008-02-05 JP JP2009548501A patent/JP2010518026A/ja not_active Withdrawn
- 2008-02-05 MX MX2009008338A patent/MX2009008338A/es unknown
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