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- Withdrawn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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| EP1818058A3 (en) * | 2006-02-13 | 2007-11-07 | Astion Pharma A/S | Treatment of mmp-mediated dermatological diseases with pemirolast |
-
2008
- 2008-02-05 CA CA002677493A patent/CA2677493A1/en not_active Abandoned
- 2008-02-05 CL CL200800369A patent/CL2008000369A1/es unknown
- 2008-02-05 BR BRPI0807351-1A patent/BRPI0807351A2/pt not_active IP Right Cessation
- 2008-02-05 RU RU2009133336/04A patent/RU2009133336A/ru unknown
- 2008-02-05 EP EP08729067A patent/EP2079737A1/en not_active Withdrawn
- 2008-02-05 US US12/026,435 patent/US20080194616A1/en not_active Abandoned
- 2008-02-05 JP JP2009548501A patent/JP2010518026A/ja not_active Withdrawn
- 2008-02-05 TW TW097104675A patent/TW200838539A/zh unknown
- 2008-02-05 AR ARP080100493A patent/AR065194A1/es unknown
- 2008-02-05 WO PCT/US2008/053075 patent/WO2008097991A1/en not_active Ceased
- 2008-02-05 AU AU2008213836A patent/AU2008213836A1/en not_active Abandoned
- 2008-02-05 MX MX2009008338A patent/MX2009008338A/es unknown
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