JP2007506740A5 - - Google Patents
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- Publication number
- JP2007506740A5 JP2007506740A5 JP2006528069A JP2006528069A JP2007506740A5 JP 2007506740 A5 JP2007506740 A5 JP 2007506740A5 JP 2006528069 A JP2006528069 A JP 2006528069A JP 2006528069 A JP2006528069 A JP 2006528069A JP 2007506740 A5 JP2007506740 A5 JP 2007506740A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- methoxy
- phenylisoquinolin
- group
- 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.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- YDPIQLCFGNPGAE-UHFFFAOYSA-N 2-[2-[(6-methoxy-2-methyl-1-oxo-4-phenylisoquinolin-3-yl)methoxy]ethyl]isoindole-1,3-dione Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COCCN3C(C4=CC=CC=C4C3=O)=O)=O)C=1C=2C1=CC=CC=C1 YDPIQLCFGNPGAE-UHFFFAOYSA-N 0.000 claims 1
- LDARLODISWKOJE-UHFFFAOYSA-N 3-(2-aminoethoxymethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COCCN)=O)C=1C=2C1=CC=CC=C1 LDARLODISWKOJE-UHFFFAOYSA-N 0.000 claims 1
- SVTVKQXHPCWEMD-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanylmethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2CSCCO)=O)C=1C=2C1=CC=CC=C1 SVTVKQXHPCWEMD-UHFFFAOYSA-N 0.000 claims 1
- HSNNPRZEBCASFH-UHFFFAOYSA-N 3-(2-hydroxyethylsulfinylmethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2CS(=O)CCO)=O)C=1C=2C1=CC=CC=C1 HSNNPRZEBCASFH-UHFFFAOYSA-N 0.000 claims 1
- KQIKKBYDOJJGCU-UHFFFAOYSA-N 3-(2-hydroxyethylsulfonylmethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2CS(=O)(=O)CCO)=O)C=1C=2C1=CC=CC=C1 KQIKKBYDOJJGCU-UHFFFAOYSA-N 0.000 claims 1
- IWNVYQWDLDEFLV-UHFFFAOYSA-N 3-(hydroxymethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2CO)=O)C=1C=2C1=CC=CC=C1 IWNVYQWDLDEFLV-UHFFFAOYSA-N 0.000 claims 1
- XYXNWBHWYCXFNQ-UHFFFAOYSA-N 3-[(2-hydroxy-3-morpholin-4-ylpropoxy)methyl]-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COCC(O)CN3CCOCC3)=O)C=1C=2C1=CC=CC=C1 XYXNWBHWYCXFNQ-UHFFFAOYSA-N 0.000 claims 1
- FKCUMWAOEYJLQU-UHFFFAOYSA-N 3-[(2-hydroxy-3-piperidin-1-ylpropoxy)methyl]-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COCC(O)CN3CCCCC3)=O)C=1C=2C1=CC=CC=C1 FKCUMWAOEYJLQU-UHFFFAOYSA-N 0.000 claims 1
- ILMDJDVARHUOBU-UHFFFAOYSA-N 3-[2-(dimethylamino)ethylsulfanylmethyl]-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2CSCCN(C)C)=O)C=1C=2C1=CC=CC=C1 ILMDJDVARHUOBU-UHFFFAOYSA-N 0.000 claims 1
- ZRPMJYYBXIWATF-UHFFFAOYSA-N 3-[[3-(dimethylamino)-2-hydroxypropoxy]methyl]-6-methoxy-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COCC(O)CN(C)C)=O)C=1C=2C1=CC=CC=C1 ZRPMJYYBXIWATF-UHFFFAOYSA-N 0.000 claims 1
- CTEXTSNELRYSDS-UHFFFAOYSA-N 6-methoxy-2-methyl-3-(2-methylsulfonylethoxymethyl)-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COCCS(C)(=O)=O)=O)C=1C=2C1=CC=CC=C1 CTEXTSNELRYSDS-UHFFFAOYSA-N 0.000 claims 1
- CEHMIYSHZGNIAL-UHFFFAOYSA-N 6-methoxy-2-methyl-3-(2-morpholin-4-ylethoxymethyl)-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N2C)=O)C=1C(C=1C=CC=CC=1)=C2COCCN1CCOCC1 CEHMIYSHZGNIAL-UHFFFAOYSA-N 0.000 claims 1
- KIELNGZIKQDIDT-UHFFFAOYSA-N 6-methoxy-2-methyl-3-(oxiran-2-ylmethoxymethyl)-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N2C)=O)C=1C(C=1C=CC=CC=1)=C2COCC1CO1 KIELNGZIKQDIDT-UHFFFAOYSA-N 0.000 claims 1
- AMMIYUPLDPJFMP-UHFFFAOYSA-N 6-methoxy-2-methyl-3-(oxolan-3-yloxymethyl)-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N2C)=O)C=1C(C=1C=CC=CC=1)=C2COC1CCOC1 AMMIYUPLDPJFMP-UHFFFAOYSA-N 0.000 claims 1
- LUMOJUZJAKCBHI-UHFFFAOYSA-N 6-methoxy-2-methyl-3-[(1-methylpiperidin-3-yl)oxymethyl]-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COC3CN(C)CCC3)=O)C=1C=2C1=CC=CC=C1 LUMOJUZJAKCBHI-UHFFFAOYSA-N 0.000 claims 1
- LGYUWZFMBYRJFV-UHFFFAOYSA-N 6-methoxy-2-methyl-3-[(2-methylpropan-2-yl)oxymethyl]-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COC(C)(C)C)=O)C=1C=2C1=CC=CC=C1 LGYUWZFMBYRJFV-UHFFFAOYSA-N 0.000 claims 1
- OBQVTYQYSKAHKB-UHFFFAOYSA-N 6-methoxy-2-methyl-4-phenyl-3-(2,2,2-trifluoroethoxymethyl)isoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COCC(F)(F)F)=O)C=1C=2C1=CC=CC=C1 OBQVTYQYSKAHKB-UHFFFAOYSA-N 0.000 claims 1
- UGIYVAZPOXMLKI-UHFFFAOYSA-N 6-methoxy-2-methyl-4-phenyl-3-(pyridin-4-ylmethoxymethyl)isoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N(C)C=2COCC=3C=CN=CC=3)=O)C=1C=2C1=CC=CC=C1 UGIYVAZPOXMLKI-UHFFFAOYSA-N 0.000 claims 1
- ADXHXVCCBOJWLH-UHFFFAOYSA-N 6-methoxy-3-(2-methoxyethoxymethyl)-2-methyl-4-phenylisoquinolin-1-one Chemical compound C12=CC(OC)=CC=C2C(=O)N(C)C(COCCOC)=C1C1=CC=CC=C1 ADXHXVCCBOJWLH-UHFFFAOYSA-N 0.000 claims 1
- DVFLLNORYZMKLR-UHFFFAOYSA-N 6-methoxy-3-(methoxymethyl)-2-methyl-4-phenylisoquinolin-1-one Chemical compound C12=CC(OC)=CC=C2C(=O)N(C)C(COC)=C1C1=CC=CC=C1 DVFLLNORYZMKLR-UHFFFAOYSA-N 0.000 claims 1
- WTVQPFXKLXRKDQ-UHFFFAOYSA-N 6-methoxy-3-[(6-methoxy-2-methyl-1-oxo-4-phenylisoquinolin-3-yl)methoxymethyl]-2-methyl-4-phenylisoquinolin-1-one Chemical compound C=1C(OC)=CC=C(C(N2C)=O)C=1C(C=1C=CC=CC=1)=C2COCC(N(C(=O)C1=CC=C(OC)C=C11)C)=C1C1=CC=CC=C1 WTVQPFXKLXRKDQ-UHFFFAOYSA-N 0.000 claims 1
- IPUBDKTYRTVISD-UHFFFAOYSA-N 6-methoxy-3-[2-(2-methoxyethoxy)ethoxymethyl]-2-methyl-4-phenylisoquinolin-1-one Chemical compound C12=CC(OC)=CC=C2C(=O)N(C)C(COCCOCCOC)=C1C1=CC=CC=C1 IPUBDKTYRTVISD-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50521403P | 2003-09-23 | 2003-09-23 | |
| US60/505,214 | 2003-09-23 | ||
| PCT/US2004/030470 WO2005046578A2 (en) | 2003-09-23 | 2004-09-17 | Isoquinolinone potassium channel inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007506740A JP2007506740A (ja) | 2007-03-22 |
| JP2007506740A5 true JP2007506740A5 (enExample) | 2011-03-10 |
| JP4719151B2 JP4719151B2 (ja) | 2011-07-06 |
Family
ID=34590091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006528069A Expired - Fee Related JP4719151B2 (ja) | 2003-09-23 | 2004-09-17 | イソキノリノンカリウムチャネル阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7709476B2 (enExample) |
| EP (1) | EP1667978B1 (enExample) |
| JP (1) | JP4719151B2 (enExample) |
| CN (1) | CN1856474A (enExample) |
| AU (1) | AU2004289186B2 (enExample) |
| CA (1) | CA2539853C (enExample) |
| WO (1) | WO2005046578A2 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1667976B1 (en) * | 2003-09-23 | 2010-08-04 | Merck Sharp & Dohme Corp. | Isoquinolinone potassium channel inhibitors |
| WO2005030729A1 (en) * | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinoline potassium channel inhibitors |
| JP4719152B2 (ja) * | 2003-09-23 | 2011-07-06 | メルク・シャープ・エンド・ドーム・コーポレイション | イソキノリノンカリウムチャネル阻害剤 |
| US7723352B2 (en) * | 2003-09-23 | 2010-05-25 | Merck Sharp & Dohme | Isoquinolinone potassium channel inhibitors |
| US7723290B2 (en) | 2004-10-22 | 2010-05-25 | Bioincept, Llc | Compositions and methods for modulating the immune system |
| DE102005028862A1 (de) * | 2005-06-22 | 2007-01-11 | Sanofi-Aventis Deutschland Gmbh | Substituierte Heterocyclen, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| GB0525164D0 (en) | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| SG174095A1 (en) * | 2006-08-23 | 2011-09-29 | Valeant Pharmaceuticals Int | Derivatives of 4-(n-azacycloalkyl) anilides as potassium channel modulators |
| GB0815782D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815781D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815784D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| US8883852B2 (en) | 2008-10-22 | 2014-11-11 | University of Pittburgh—Of the Commonwealth System of Higher Education | Radioprotective agents |
| KR101763656B1 (ko) | 2009-06-29 | 2017-08-01 | 인사이트 홀딩스 코포레이션 | Ｐｉ3ｋ 저해물질로서의 피리미디논 |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| EP3660016A1 (en) | 2010-12-20 | 2020-06-03 | Incyte Holdings Corporation | N-(1-(substituted-phenyl)ethyl)-9h-purin-6-amines as pi3k inhibitors |
| US9737585B2 (en) * | 2011-03-02 | 2017-08-22 | Bioincept, Llc | Compositions and methods for treatment of intracellular damage and bacterial infection |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| WO2012135009A1 (en) | 2011-03-25 | 2012-10-04 | Incyte Corporation | Pyrimidine-4,6-diamine derivatives as pi3k inhibitors |
| PT3513793T (pt) | 2011-09-02 | 2021-05-10 | Incyte Holdings Corp | Heterociclilaminas como inibidores de pi3k |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| WO2017039751A1 (en) | 2015-08-28 | 2017-03-09 | Bioincept, Llc | Mutant peptides and methods of treating subjects using the same |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| SG10201907576SA (en) | 2015-02-27 | 2019-09-27 | Incyte Corp | Salts of pi3k inhibitor and processes for their preparation |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| EP3341006A4 (en) | 2015-08-28 | 2019-03-13 | BioIncept LLC | COMPOSITIONS AND METHODS FOR TREATING NERVE DAMAGE |
| SG11202011680YA (en) | 2018-06-01 | 2020-12-30 | Incyte Corp | Dosing regimen for the treatment of pi3k related disorders |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ227743A (en) * | 1988-01-27 | 1991-01-29 | May & Baker Ltd | Isoquinolinone derivatives and their pharmaceutical compositions |
| JP3724818B2 (ja) * | 1992-09-04 | 2005-12-07 | 武田薬品工業株式会社 | 縮合複素環化合物、その製造法および剤 |
| EP0585913B1 (en) * | 1992-09-04 | 1997-12-29 | Takeda Chemical Industries, Ltd. | Condensed heterocyclic compounds, their production and use |
| JPH0776573A (ja) * | 1993-07-14 | 1995-03-20 | Takeda Chem Ind Ltd | ヘテロ環化合物、その製造法および剤 |
| EP0634402A1 (en) * | 1993-07-14 | 1995-01-18 | Takeda Chemical Industries, Ltd. | Isochinolinone derivatives, their production and use |
| US5387685A (en) | 1993-07-16 | 1995-02-07 | American Cyanamid Co | MDR reversal agents |
| AU2001269516B2 (en) * | 2000-07-13 | 2006-09-14 | Takeda Pharmaceutical Company Limited | Lipid-rich plaque regressing agents |
| AU2002212969B2 (en) * | 2000-09-20 | 2006-07-06 | Merck Sharp & Dohme Corp. | Isoquinolinone potassium channel inhibitors |
| SK10802003A3 (sk) * | 2001-02-02 | 2004-05-04 | Takeda Chemical Industries, Ltd. | Kondenzovaná heterocyklická zlúčenina, jej použitie a jej farmaceutický prípravok |
| JP4213390B2 (ja) * | 2001-02-02 | 2009-01-21 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| WO2003068750A1 (en) * | 2002-02-13 | 2003-08-21 | Takeda Chemical Industries, Ltd. | Jnk inhibitor |
| WO2005030729A1 (en) * | 2003-09-23 | 2005-04-07 | Merck & Co., Inc. | Isoquinoline potassium channel inhibitors |
| US7723352B2 (en) * | 2003-09-23 | 2010-05-25 | Merck Sharp & Dohme | Isoquinolinone potassium channel inhibitors |
| EP1667976B1 (en) * | 2003-09-23 | 2010-08-04 | Merck Sharp & Dohme Corp. | Isoquinolinone potassium channel inhibitors |
| JP4719152B2 (ja) * | 2003-09-23 | 2011-07-06 | メルク・シャープ・エンド・ドーム・コーポレイション | イソキノリノンカリウムチャネル阻害剤 |
-
2004
- 2004-09-17 AU AU2004289186A patent/AU2004289186B2/en not_active Ceased
- 2004-09-17 EP EP04816878.5A patent/EP1667978B1/en not_active Expired - Lifetime
- 2004-09-17 CA CA2539853A patent/CA2539853C/en not_active Expired - Fee Related
- 2004-09-17 US US10/571,857 patent/US7709476B2/en not_active Expired - Fee Related
- 2004-09-17 WO PCT/US2004/030470 patent/WO2005046578A2/en not_active Ceased
- 2004-09-17 CN CNA2004800273751A patent/CN1856474A/zh active Pending
- 2004-09-17 JP JP2006528069A patent/JP4719151B2/ja not_active Expired - Fee Related
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