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)
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- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
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- Physical Education & Sports Medicine (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Immunology (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
ID=39420569
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 (OSRAM) |
| EP (1) | EP2079737A1 (OSRAM) |
| JP (1) | JP2010518026A (OSRAM) |
| AR (1) | AR065194A1 (OSRAM) |
| AU (1) | AU2008213836A1 (OSRAM) |
| BR (1) | BRPI0807351A2 (OSRAM) |
| CA (1) | CA2677493A1 (OSRAM) |
| CL (1) | CL2008000369A1 (OSRAM) |
| MX (1) | MX2009008338A (OSRAM) |
| RU (1) | RU2009133336A (OSRAM) |
| TW (1) | TW200838539A (OSRAM) |
| WO (1) | WO2008097991A1 (OSRAM) |
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| US8933236B2 (en) | 2012-05-22 | 2015-01-13 | Xenon Pharmaceuticals Inc. | N-substituted benzamides and methods of use thereof |
| WO2008074975A1 (en) * | 2006-12-18 | 2008-06-26 | Cardoz Ab | New combination for use in the treatment of inflammatory disorders |
| EP2107907B1 (en) * | 2006-12-20 | 2012-02-01 | Cardoz AB | Combination of pemirolast and ramatroban for use in the treatment of inflammatory disorders |
| NZ595781A (en) * | 2008-01-11 | 2013-07-26 | Glenmark Pharmaceuticals Sa | Fused 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 |
| CN102482278B (zh) | 2009-06-29 | 2015-04-22 | 因塞特公司 | 作为pi3k抑制剂的嘧啶酮类 |
| WO2011075643A1 (en) * | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted heteroaryl fused derivatives as pi3k inhibitors |
| US8680108B2 (en) * | 2009-12-18 | 2014-03-25 | Incyte Corporation | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 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 |
| TW201249844A (en) | 2010-12-20 | 2012-12-16 | Incyte Corp | N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors |
| 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 |
| TWI648277B (zh) | 2011-09-02 | 2019-01-21 | 美商英塞特控股公司 | 作為ｐｉ３ｋ抑制劑之雜環基胺 |
| WO2013064984A1 (en) | 2011-10-31 | 2013-05-10 | Xenon Pharmaceuticals Inc. | Biaryl ether sulfonamides and their use as therapeutic agents |
| JP6014154B2 (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． | ベンゼンスルホンアミド化合物および治療剤としてのそれらの使用 |
| US9567331B2 (en) | 2011-11-15 | 2017-02-14 | Trustees Of Boston University | Pyridopyrimidinone inhibitors of viruses |
| US9206127B2 (en) | 2012-03-16 | 2015-12-08 | Purdue Pharm, L.P. | Substituted pyridines as sodium channel blockers |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| BR112015000187A2 (pt) * | 2012-07-06 | 2017-06-27 | Genentech Inc | benzamidas substituídas com n e métodos de uso das mesmas |
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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 |
| 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 |
| JP2008546843A (ja) * | 2005-06-27 | 2008-12-25 | アムゲン インコーポレイティッド | 抗炎症性アリールニトリル化合物 |
| US7939537B2 (en) * | 2005-10-04 | 2011-05-10 | Istituto Di Ricerche 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 |
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2008
- 2008-02-05 US US12/026,435 patent/US20080194616A1/en not_active Abandoned
- 2008-02-05 AU AU2008213836A patent/AU2008213836A1/en not_active Abandoned
- 2008-02-05 AR ARP080100493A patent/AR065194A1/es unknown
- 2008-02-05 TW TW097104675A patent/TW200838539A/zh unknown
- 2008-02-05 RU RU2009133336/04A patent/RU2009133336A/ru unknown
- 2008-02-05 MX MX2009008338A patent/MX2009008338A/es unknown
- 2008-02-05 EP EP08729067A patent/EP2079737A1/en not_active Withdrawn
- 2008-02-05 BR BRPI0807351-1A patent/BRPI0807351A2/pt not_active IP Right Cessation
- 2008-02-05 CL CL200800369A patent/CL2008000369A1/es unknown
- 2008-02-05 CA CA002677493A patent/CA2677493A1/en not_active Abandoned
- 2008-02-05 WO PCT/US2008/053075 patent/WO2008097991A1/en not_active Ceased
- 2008-02-05 JP JP2009548501A patent/JP2010518026A/ja not_active Withdrawn
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| AR065194A1 (es) | 2009-05-20 |
| AU2008213836A1 (en) | 2008-08-14 |
| CL2008000369A1 (es) | 2008-04-18 |
| US20080194616A1 (en) | 2008-08-14 |
| WO2008097991A1 (en) | 2008-08-14 |
| TW200838539A (en) | 2008-10-01 |
| MX2009008338A (es) | 2009-08-12 |
| BRPI0807351A2 (pt) | 2014-05-20 |
| JP2010518026A (ja) | 2010-05-27 |
| RU2009133336A (ru) | 2011-03-20 |
| EP2079737A1 (en) | 2009-07-22 |
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