CA2677493A1 - Pyridopyrimidinone compounds useful in treating sodium channel-mediated diseases or conditions - Google Patents
Pyridopyrimidinone compounds useful in treating sodium channel-mediated diseases or conditions Download PDFInfo
- Publication number
- CA2677493A1 CA2677493A1 CA002677493A CA2677493A CA2677493A1 CA 2677493 A1 CA2677493 A1 CA 2677493A1 CA 002677493 A CA002677493 A CA 002677493A CA 2677493 A CA2677493 A CA 2677493A CA 2677493 A1 CA2677493 A1 CA 2677493A1
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- CA
- Canada
- Prior art keywords
- optionally substituted
- heterocyclyl
- heteroaryl
- pyrido
- pyrimidin
- 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.)
- Abandoned
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- 102000018674 Sodium Channels Human genes 0.000 title claims abstract description 74
- 108010052164 Sodium Channels Proteins 0.000 title claims abstract description 74
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 54
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- 230000001404 mediated effect Effects 0.000 title claims abstract description 22
- IAAQUOVTPAMQCR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-2-one Chemical class C1=CC=C2NC(=O)N=CC2=N1 IAAQUOVTPAMQCR-UHFFFAOYSA-N 0.000 title abstract description 6
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- 239000000203 mixture Substances 0.000 claims abstract description 73
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- 229940002612 prodrug Drugs 0.000 claims abstract description 58
- 239000000651 prodrug Substances 0.000 claims abstract description 58
- 239000012453 solvate Substances 0.000 claims abstract description 48
- 238000011282 treatment Methods 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 272
- 125000001188 haloalkyl group Chemical group 0.000 claims description 249
- 150000001875 compounds Chemical class 0.000 claims description 246
- 125000000623 heterocyclic group Chemical group 0.000 claims description 217
- 125000001072 heteroaryl group Chemical group 0.000 claims description 213
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 209
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 200
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 200
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 200
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 165
- 239000001257 hydrogen Substances 0.000 claims description 161
- 229910052739 hydrogen Inorganic materials 0.000 claims description 161
- -1 heterocyclylalkynyl Chemical group 0.000 claims description 145
- 125000003118 aryl group Chemical group 0.000 claims description 122
- 125000003342 alkenyl group Chemical group 0.000 claims description 121
- 125000002947 alkylene group Chemical group 0.000 claims description 110
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 103
- 125000003107 substituted aryl group Chemical group 0.000 claims description 102
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 98
- 125000000304 alkynyl group Chemical group 0.000 claims description 90
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- 238000000034 method Methods 0.000 claims description 74
- 125000001424 substituent group Chemical group 0.000 claims description 68
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
- 239000008194 pharmaceutical composition Substances 0.000 claims description 56
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 53
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 52
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 51
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 50
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 50
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 49
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 48
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 47
- 125000004450 alkenylene group Chemical group 0.000 claims description 42
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 41
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000004419 alkynylene group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
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- FIYBEHLETGRDHT-UHFFFAOYSA-N 3-(4-aminophenyl)-2-butylpyrido[1,2-a]pyrimidin-4-one Chemical compound CCCCC=1N=C2C=CC=CN2C(=O)C=1C1=CC=C(N)C=C1 FIYBEHLETGRDHT-UHFFFAOYSA-N 0.000 claims description 3
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- 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
- 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
- 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
- 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
- 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
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- 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
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Classifications
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- 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
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Pain & Pain Management (AREA)
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- Psychiatry (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
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- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88825307P | 2007-02-05 | 2007-02-05 | |
| US60/888,253 | 2007-02-05 | ||
| US91212207P | 2007-04-16 | 2007-04-16 | |
| US60/912,122 | 2007-04-16 | ||
| PCT/US2008/053075 WO2008097991A1 (en) | 2007-02-05 | 2008-02-05 | Pyridopyrimidinone compounds useful in treating sodium channel-mediated diseases or conditions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2677493A1 true CA2677493A1 (en) | 2008-08-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002677493A Abandoned CA2677493A1 (en) | 2007-02-05 | 2008-02-05 | Pyridopyrimidinone compounds useful in treating sodium channel-mediated diseases or conditions |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080194616A1 (pt-PT) |
| EP (1) | EP2079737A1 (pt-PT) |
| JP (1) | JP2010518026A (pt-PT) |
| AR (1) | AR065194A1 (pt-PT) |
| AU (1) | AU2008213836A1 (pt-PT) |
| BR (1) | BRPI0807351A2 (pt-PT) |
| CA (1) | CA2677493A1 (pt-PT) |
| CL (1) | CL2008000369A1 (pt-PT) |
| MX (1) | MX2009008338A (pt-PT) |
| RU (1) | RU2009133336A (pt-PT) |
| TW (1) | TW200838539A (pt-PT) |
| WO (1) | WO2008097991A1 (pt-PT) |
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| DK2120919T3 (da) * | 2006-12-18 | 2012-11-26 | Cardoz Ab | Ny kombination til anvendelse ved behandling af inflammatoriske lidelser |
| AU2007336077A1 (en) * | 2006-12-20 | 2008-06-26 | Cardoz Ab | New combination for use in the treatment of inflammatory disorders |
| EP2229388A4 (en) * | 2008-01-11 | 2012-03-07 | Glenmark Pharmaceuticals Sa | CONDENSED PYRIMIDINE DERIVATIVES AS TRPV3 MODULATORS |
| CN101531638B (zh) * | 2008-03-13 | 2011-12-28 | 中国科学院广州生物医药与健康研究院 | 用作雌激素相关受体调节剂的化合物及其应用 |
| US20110092463A1 (en) * | 2008-04-07 | 2011-04-21 | Johan Raud | Combination for use in the treatment of inflammatory disorders |
| US8119647B2 (en) * | 2008-04-23 | 2012-02-21 | Glenmark Pharmaceuticals S.A. | Fused pyrimidineone compounds as TRPV3 modulators |
| CN101628913B (zh) * | 2008-07-18 | 2013-01-23 | 中国科学院广州生物医药与健康研究院 | 用作雌激素相关受体调节剂的化合物及其应用 |
| PL2448938T3 (pl) | 2009-06-29 | 2014-11-28 | Incyte Holdings Corp | Pirymidynony jako inhibitory PI3K |
| US8759359B2 (en) * | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| WO2011075630A1 (en) * | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted fused aryl and heteroaryl derivatives as pi3k inhibitors |
| WO2011130342A1 (en) | 2010-04-14 | 2011-10-20 | Incyte Corporation | FUSED DERIVATIVES AS ΡI3Κδ INHIBITORS |
| US9062055B2 (en) | 2010-06-21 | 2015-06-23 | Incyte Corporation | Fused pyrrole derivatives as PI3K inhibitors |
| US9120752B2 (en) | 2010-07-16 | 2015-09-01 | Purdue Pharma, L.P. | Pyridine compounds as sodium channel blockers |
| JP5961187B2 (ja) | 2010-12-20 | 2016-08-02 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉ３ｋ阻害剤としてのｎ−（１−（置換フェニル）エチル）−９ｈ−プリン−６−アミン |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| US9126948B2 (en) | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
| HUE030869T2 (en) | 2011-09-02 | 2017-06-28 | Incyte Holdings Corp | Heterocyclic amines as inhibitors of PI3K |
| RU2014121983A (ru) | 2011-10-31 | 2015-12-10 | Ксенон Фармасьютикалз Инк. | Биарильные простоэфирные сульфонамиды и их применение в качестве терапевтических средств |
| US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| US9567331B2 (en) | 2011-11-15 | 2017-02-14 | 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 |
| US8952169B2 (en) * | 2012-05-22 | 2015-02-10 | Xenon Pharmaceuticals Inc. | N-substituted benzamides and methods of use thereof |
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| 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 |
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| AU2006299042B8 (en) * | 2005-10-04 | 2011-09-15 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | HIV integrase inhibitors |
| EP1818058A3 (en) * | 2006-02-13 | 2007-11-07 | Astion Pharma A/S | Treatment of mmp-mediated dermatological diseases with pemirolast |
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- 2008-02-05 AR ARP080100493A patent/AR065194A1/es unknown
- 2008-02-05 RU RU2009133336/04A patent/RU2009133336A/ru unknown
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- 2008-02-05 JP JP2009548501A patent/JP2010518026A/ja not_active Withdrawn
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| AR065194A1 (es) | 2009-05-20 |
| JP2010518026A (ja) | 2010-05-27 |
| BRPI0807351A2 (pt) | 2014-05-20 |
| RU2009133336A (ru) | 2011-03-20 |
| US20080194616A1 (en) | 2008-08-14 |
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