CA2665398A1 - Indazolyl derivatives useful as potassium channel modulating agents - Google Patents
Indazolyl derivatives useful as potassium channel modulating agents Download PDFInfo
- Publication number
- CA2665398A1 CA2665398A1 CA002665398A CA2665398A CA2665398A1 CA 2665398 A1 CA2665398 A1 CA 2665398A1 CA 002665398 A CA002665398 A CA 002665398A CA 2665398 A CA2665398 A CA 2665398A CA 2665398 A1 CA2665398 A1 CA 2665398A1
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- Canada
- Prior art keywords
- alkyl
- amino
- cycloalkyl
- alkoxy
- chloro
- 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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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 title claims abstract description 58
- 102000004257 Potassium Channel Human genes 0.000 title claims abstract description 24
- 108020001213 potassium channel Proteins 0.000 title claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 title abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 56
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 238000011282 treatment Methods 0.000 claims abstract description 15
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- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 57
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
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- 238000000034 method Methods 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 33
- -1 2-indazolyl Chemical class 0.000 claims description 32
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 32
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- 125000004103 aminoalkyl group Chemical group 0.000 claims description 32
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
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- SXTZVSCCGYEFOY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-indazol-1-ylpyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1CNC1=CC=NC(N2C3=CC=CC=C3C=N2)=N1 SXTZVSCCGYEFOY-UHFFFAOYSA-N 0.000 claims description 5
- TXGZRDGSNSTOIW-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-indazol-2-ylpyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1CNC1=CC=NC(N2N=C3C=CC=CC3=C2)=N1 TXGZRDGSNSTOIW-UHFFFAOYSA-N 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
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- 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 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- BUKLUWFZTMICFQ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(6-nitroindazol-2-yl)pyrimidin-4-amine Chemical compound N1=C2C=C([N+](=O)[O-])C=CC2=CN1C(N=1)=NC=CC=1NC1=CC=C(Cl)C=C1 BUKLUWFZTMICFQ-UHFFFAOYSA-N 0.000 claims description 4
- JJDDIEUKPRBQNR-UHFFFAOYSA-N n-(4-chlorophenyl)-2-indazol-1-yl-6-methylpyrimidin-4-amine Chemical compound N=1C(N2C3=CC=CC=C3C=N2)=NC(C)=CC=1NC1=CC=C(Cl)C=C1 JJDDIEUKPRBQNR-UHFFFAOYSA-N 0.000 claims description 4
- SGDLUZVNNSOSBZ-UHFFFAOYSA-N n-(4-chlorophenyl)-6-indazol-1-ylpyridin-2-amine Chemical compound C1=CC(Cl)=CC=C1NC1=CC=CC(N2C3=CC=CC=C3C=N2)=N1 SGDLUZVNNSOSBZ-UHFFFAOYSA-N 0.000 claims description 4
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- GOOFDKIMFIZGRV-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(5-nitroindazol-2-yl)pyrimidin-4-amine Chemical compound C1=C2C=C([N+](=O)[O-])C=CC2=NN1C(N=1)=NC=CC=1NC1=CC=C(Cl)C=C1 GOOFDKIMFIZGRV-UHFFFAOYSA-N 0.000 claims description 3
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- QIWUMMHCYOXAED-UHFFFAOYSA-N n-cyclohexyl-2-indazol-1-ylpyrimidin-4-amine Chemical compound C1CCCCC1NC1=CC=NC(N2C3=CC=CC=C3C=N2)=N1 QIWUMMHCYOXAED-UHFFFAOYSA-N 0.000 claims description 3
- CZAADHJQSOAANV-UHFFFAOYSA-N 2-[4-(4-chloroanilino)pyrimidin-2-yl]indazol-6-amine Chemical compound N1=C2C=C(N)C=CC2=CN1C(N=1)=NC=CC=1NC1=CC=C(Cl)C=C1 CZAADHJQSOAANV-UHFFFAOYSA-N 0.000 claims description 2
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| US82794006P | 2006-10-03 | 2006-10-03 | |
| US60/827,940 | 2006-10-03 | ||
| DKPA200601280 | 2006-10-03 | ||
| DKPA200601280 | 2006-10-03 | ||
| PCT/EP2007/060493 WO2008040753A1 (en) | 2006-10-03 | 2007-10-03 | Indazolyl derivatives useful as potassium channel modulating agents |
Publications (1)
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| CA2665398A1 true CA2665398A1 (en) | 2008-04-10 |
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| CA002665398A Abandoned CA2665398A1 (en) | 2006-10-03 | 2007-10-03 | Indazolyl derivatives useful as potassium channel modulating agents |
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| JP (1) | JP2010505794A (enExample) |
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| EP2066655A2 (en) * | 2006-09-07 | 2009-06-10 | Neurosearch A/S | Pyridinyl-pyrimidine derivatives useful as potassium channel modulating agents |
| WO2008092942A2 (en) * | 2007-02-02 | 2008-08-07 | Neurosearch A/S | Pyridinyl-pyrazole derivatives and their use as potassium channel modulators |
| MX2009010122A (es) | 2007-03-28 | 2009-10-19 | Neurosearch As | Derivados de purinilo y su uso como moduladores del canal de potasio. |
| EP2203436A1 (en) | 2007-09-17 | 2010-07-07 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
| WO2010007944A1 (ja) * | 2008-07-17 | 2010-01-21 | 旭化成ファーマ株式会社 | 含窒素二環性複素環化合物 |
| JP2012501308A (ja) * | 2008-09-02 | 2012-01-19 | ノイロサーチ アクティーゼルスカブ | ピラゾリルピリミジン誘導体及びカリウムチャネルモジュレーターとしてのそれらの使用 |
| EP2344501A1 (en) * | 2008-09-26 | 2011-07-20 | NeuroSearch A/S | Substituted purinyl-pyrazol derivatives and their use as potassium channel modulators |
| WO2010034707A1 (en) | 2008-09-26 | 2010-04-01 | Neurosearch A/S | Substituted purinyl-pyrazol derivatives and their use as potassium channel modulators |
| CA2743864A1 (en) * | 2008-11-25 | 2010-06-10 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| WO2011119518A1 (en) | 2010-03-25 | 2011-09-29 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| NZ603884A (en) | 2010-05-27 | 2014-06-27 | Merck Sharp & Dohme | Soluble guanylate cyclase activators |
| EP2632551B1 (en) | 2010-10-28 | 2016-07-06 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| JP6223443B2 (ja) | 2012-06-26 | 2017-11-01 | サニオナ・エイピイエス | フェニルトリアゾール誘導体及びｇａｂａａ受容体複合体を調節するための該フェニルトリアゾール誘導体の使用 |
| AU2013348009C1 (en) | 2012-11-21 | 2019-08-08 | Ptc Therapeutics, Inc. | Substituted reverse pyrimidine Bmi-1 inhibitors |
| US9802904B2 (en) | 2012-12-28 | 2017-10-31 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Inhibitors of the USP1/UAF1 deubiquitinase complex and uses thereof |
| MX370588B (es) | 2013-08-30 | 2019-12-16 | Ptc Therapeutics Inc | Inhibidores de la bmi-1 de pirimidina sustituida. |
| EP3071553A4 (en) | 2013-11-21 | 2017-08-02 | PTC Therapeutics, Inc. | Substituted pyridine and pyrazine bmi-1 inhibitors |
| US9868722B2 (en) | 2013-12-10 | 2018-01-16 | Cleave Biosciences, Inc. | Monocyclic pyrimidine/pyridine compounds as inhibitors of P97 complex |
| SG11201605699QA (en) | 2014-01-20 | 2016-08-30 | Cleave Biosciences Inc | FUSED PYRIMIDINES AS INHIBITORS OF p97 COMPLEX |
| WO2017133664A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | Bicyclic pyridine and pyrimidine derivatives and their use in the treatment， amelioration or prevention of influenza |
| WO2017148995A1 (en) | 2016-03-04 | 2017-09-08 | Bayer Pharma Aktiengesellschaft | 1-(pyrimidin-2-yl)-1h-indazoles having bub1 kinase inhibiting activity |
| AU2017275657B2 (en) | 2016-06-02 | 2021-08-19 | Novartis Ag | Potassium channel modulators |
| RS62899B1 (sr) | 2017-01-23 | 2022-03-31 | Cadent Therapeutics Inc | Modulatori kalijumovih kanala |
| WO2019074810A1 (en) * | 2017-10-11 | 2019-04-18 | Merck Sharp & Dohme Corp. | INDAZOLYL-SPIRO [2,3] HEXANE-CARBONITRILE DERIVATIVES AS INHIBITORS OF LRRK2, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF |
| US11161854B2 (en) | 2017-10-11 | 2021-11-02 | Merck Sharp & Dohme Corp. | Indazolyl-spiro[2.2]pentane-carbonitrile derivatives as LRRK2 inhibitors, pharmaceutical compositions, and uses thereof |
| WO2020055544A2 (en) | 2018-08-17 | 2020-03-19 | Ptc Therapeutics, Inc. | Method for treating pancreatic cancer |
| US11993586B2 (en) | 2018-10-22 | 2024-05-28 | Novartis Ag | Crystalline forms of potassium channel modulators |
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| EP1373222A2 (de) * | 2001-03-15 | 2004-01-02 | Basf Aktiengesellschaft | 5-phenylpyrimidine, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung zur bekaempfung von schadpilzen |
| CL2004000409A1 (es) | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| NZ545694A (en) | 2003-12-03 | 2010-04-30 | Ym Bioscience Australia Pty Lt | Azole-based kinase inhibitors |
| AU2006224605B2 (en) | 2005-03-14 | 2012-03-01 | Aniona Aps | Potassium channel modulating agents and their medical use |
| JP2008534472A (ja) | 2005-03-22 | 2008-08-28 | ノイロサーチ アクティーゼルスカブ | カリウムチャンネル調節剤としてのピラゾリル−ピリミジン及びその医学的使用 |
| US20090124645A1 (en) | 2005-10-14 | 2009-05-14 | Neurosearch A/S | Novel Pyrimidine-2,4-Diamine Derivatives and their Use as Modulators of Small-Conductance Calcium-Activated Potassium Channels |
| EP1966184B1 (en) | 2005-12-20 | 2010-08-25 | NeuroSearch A/S | Pyridinyl-quinazoline derivatives and their medical use |
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- 2007-10-03 JP JP2009530875A patent/JP2010505794A/ja not_active Abandoned
- 2007-10-03 MX MX2009003142A patent/MX2009003142A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
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| US8222262B2 (en) | 2012-07-17 |
| AU2007304195A1 (en) | 2008-04-10 |
| JP2010505794A (ja) | 2010-02-25 |
| MX2009003142A (es) | 2009-04-06 |
| EP2074113A1 (en) | 2009-07-01 |
| US20090325989A1 (en) | 2009-12-31 |
| WO2008040753A1 (en) | 2008-04-10 |
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| FZDE | Discontinued |
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| FZDE | Discontinued |
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