TW201018665A - Isoquinolinone derivatives - Google Patents
Isoquinolinone derivatives Download PDFInfo
- Publication number
- TW201018665A TW201018665A TW098133161A TW98133161A TW201018665A TW 201018665 A TW201018665 A TW 201018665A TW 098133161 A TW098133161 A TW 098133161A TW 98133161 A TW98133161 A TW 98133161A TW 201018665 A TW201018665 A TW 201018665A
- Authority
- TW
- Taiwan
- Prior art keywords
- cyclopropyl
- fluoro
- oxo
- methyl
- dihydroisoquinolin
- Prior art date
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- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical class C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 285
- 239000000203 mixture Substances 0.000 claims description 184
- -1 -OH Chemical group 0.000 claims description 174
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 141
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 56
- 238000011282 treatment Methods 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 37
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 22
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
- 150000001204 N-oxides Chemical class 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- UHBGYFCCKRAEHA-UHFFFAOYSA-N P-toluamide Chemical compound CC1=CC=C(C(N)=O)C=C1 UHBGYFCCKRAEHA-UHFFFAOYSA-N 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 229940079593 drug Drugs 0.000 claims description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 208000006673 asthma Diseases 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000001041 indolyl group Chemical group 0.000 claims description 13
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 150000003431 steroids Chemical class 0.000 claims description 10
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 241000009298 Trigla lyra Species 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 claims description 5
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- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 4
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- QIULRTIURUDCGH-UHFFFAOYSA-N n-benzyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NCC1=CC=CC=C1 QIULRTIURUDCGH-UHFFFAOYSA-N 0.000 claims 1
- KJZWFXVXIDCBFI-DEOSSOPVSA-N n-cyclopropyl-3-fluoro-5-[2-[[1-(hydroxymethyl)cyclopropyl]methyl]-4-[[(3s)-3-(hydroxymethyl)piperazin-1-yl]methyl]-1-oxoisoquinolin-6-yl]-4-methylbenzamide Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1C(C=1)=CC=C(C(N(CC2(CO)CC2)C=2)=O)C=1C=2CN1CCN[C@H](CO)C1 KJZWFXVXIDCBFI-DEOSSOPVSA-N 0.000 claims 1
- FHTGZDVYPCEHFQ-UHFFFAOYSA-N n-methylpiperidin-4-amine Chemical compound CNC1CCNCC1 FHTGZDVYPCEHFQ-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10176408P | 2008-10-01 | 2008-10-01 | |
| US17941709P | 2009-05-19 | 2009-05-19 |
Publications (1)
| Publication Number | Publication Date |
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| TW201018665A true TW201018665A (en) | 2010-05-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098133161A TW201018665A (en) | 2008-10-01 | 2009-09-30 | Isoquinolinone derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8012980B2 (enExample) |
| EP (1) | EP2344472A4 (enExample) |
| JP (1) | JP2012504601A (enExample) |
| KR (1) | KR20110067051A (enExample) |
| CN (1) | CN102245593A (enExample) |
| AR (1) | AR073711A1 (enExample) |
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| US9173395B2 (en) | 2011-07-04 | 2015-11-03 | Bayer Intellectual Property Gmbh | Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants |
| US12496297B1 (en) * | 2020-10-23 | 2025-12-16 | Washington University | Compositions of autophagy modulating agents and uses thereof |
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| WO2000055153A1 (en) | 1999-03-17 | 2000-09-21 | Astrazeneca Ab | Amide derivatives |
| JP2004143134A (ja) * | 2002-02-13 | 2004-05-20 | Takeda Chem Ind Ltd | Ｊｎｋ阻害剤 |
| US7402595B2 (en) | 2002-02-13 | 2008-07-22 | Takeda Pharmaceutical Company Limited | JNK inhibitor |
| US6867320B2 (en) | 2002-02-21 | 2005-03-15 | Asahi Kasei Pharma Corporation | Substituted phenylalkanoic acid derivatives and use thereof |
| JP2005526068A (ja) | 2002-03-14 | 2005-09-02 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | 抗炎症剤としての単環式アロイルピリジノン類 |
| RU2297411C2 (ru) * | 2002-10-01 | 2007-04-20 | Мицубиси Фарма Корпорейшн | Изохинолиновые соединения, промежуточные соединения, способы их получения и применение |
| CN101031539A (zh) | 2003-08-14 | 2007-09-05 | 旭化成制药株式会社 | 取代的芳基链烷酸衍生物及其用途 |
| JP2007008816A (ja) | 2003-10-15 | 2007-01-18 | Ube Ind Ltd | 新規イソキノリン誘導体 |
| NZ545694A (en) | 2003-12-03 | 2010-04-30 | Ym Bioscience Australia Pty Lt | Azole-based kinase inhibitors |
| GB0402812D0 (en) | 2004-02-09 | 2004-03-10 | Tanabe Seiyaku Co | Novel compounds |
| JP2008504363A (ja) | 2004-06-29 | 2008-02-14 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | Ｐ２ｘ７受容体のベンズアミド阻害剤を利用する併用療法 |
| US20070054916A1 (en) | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| GB0428326D0 (en) * | 2004-12-24 | 2005-02-02 | Astrazeneca Ab | Amide derivatives |
| AU2005317868B2 (en) | 2004-12-24 | 2009-06-04 | Astrazeneca Ab | Amide derivatives |
| JP5049970B2 (ja) | 2005-07-26 | 2012-10-17 | サノフイ | Ｒｈｏ−キナーゼ阻害剤としてのシクロヘキシルアミンイソキノロン誘導体 |
| GB0608837D0 (en) | 2006-05-04 | 2006-06-14 | Chroma Therapeutics Ltd | Inhibitors of MAP kinase |
| JP5340918B2 (ja) | 2006-05-04 | 2013-11-13 | クロマ セラピューティクス リミテッド | ｐ３８ＭＡＰキナーゼ阻害剤 |
| TW200808771A (en) | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds II |
| CL2008000973A1 (es) * | 2007-04-05 | 2009-01-02 | Astrazeneca Ab | Compuestos derivados de 1-oxo-isoquinolina; procedimiento de preparación; composición farmacéutica; y su uso en el tratamiento de enfermedades pulmonares obstructvas crónicas (epoc) y asma. |
| JP5140154B2 (ja) | 2007-06-27 | 2013-02-06 | アストラゼネカ・アクチエボラーグ | ピラジノン誘導体および肺疾患の処置におけるそれらの使用 |
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- 2009-09-30 UY UY0001032154A patent/UY32154A/es unknown
- 2009-09-30 TW TW098133161A patent/TW201018665A/zh unknown
- 2009-10-01 CN CN2009801481701A patent/CN102245593A/zh active Pending
- 2009-10-01 JP JP2011530023A patent/JP2012504601A/ja not_active Ceased
- 2009-10-01 BR BRPI0920756A patent/BRPI0920756A2/pt not_active IP Right Cessation
- 2009-10-01 KR KR1020117009801A patent/KR20110067051A/ko not_active Withdrawn
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- 2009-10-01 EP EP09818051A patent/EP2344472A4/en not_active Withdrawn
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Also Published As
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|---|---|
| RU2011113437A (ru) | 2012-11-10 |
| CN102245593A (zh) | 2011-11-16 |
| EP2344472A4 (en) | 2012-11-28 |
| EP2344472A1 (en) | 2011-07-20 |
| AU2009300456B2 (en) | 2012-04-12 |
| BRPI0920756A2 (pt) | 2019-09-24 |
| WO2010039079A1 (en) | 2010-04-08 |
| AR073711A1 (es) | 2010-11-24 |
| US8012980B2 (en) | 2011-09-06 |
| CA2737434A1 (en) | 2010-04-08 |
| RU2512318C2 (ru) | 2014-04-10 |
| US20100099665A1 (en) | 2010-04-22 |
| KR20110067051A (ko) | 2011-06-20 |
| UY32154A (es) | 2010-04-30 |
| AU2009300456A1 (en) | 2010-04-08 |
| MX2011003489A (es) | 2011-05-02 |
| JP2012504601A (ja) | 2012-02-23 |
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