JP2010539110A5 - - Google Patents
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- Publication number
- JP2010539110A5 JP2010539110A5 JP2010524375A JP2010524375A JP2010539110A5 JP 2010539110 A5 JP2010539110 A5 JP 2010539110A5 JP 2010524375 A JP2010524375 A JP 2010524375A JP 2010524375 A JP2010524375 A JP 2010524375A JP 2010539110 A5 JP2010539110 A5 JP 2010539110A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- fluoro
- chloro
- group
- hydroxy
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 129
- 239000001257 hydrogen Substances 0.000 claims description 129
- 125000001153 fluoro group Chemical group F* 0.000 claims description 111
- 150000002431 hydrogen Chemical class 0.000 claims description 92
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 69
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- -1 cyano, hydroxy Chemical group 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000004076 pyridyl group Chemical group 0.000 claims description 30
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 22
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 11
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 11
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 18
- 239000012453 solvate Substances 0.000 claims 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical group CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 230000002062 proliferating effect Effects 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 208000035269 cancer or benign tumor Diseases 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000014081 polyp of colon Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 208000000821 Parathyroid Neoplasms Diseases 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 238000003795 desorption Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 210000001508 eye Anatomy 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 208000026045 malignant tumor of parathyroid gland Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 210000005000 reproductive tract Anatomy 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 0 CC=NN(*)C* Chemical compound CC=NN(*)C* 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07018082.3 | 2007-09-14 | ||
| EP07018082 | 2007-09-14 | ||
| PCT/EP2008/007137 WO2009033581A1 (en) | 2007-09-14 | 2008-09-02 | Substituted tricyclic compounds and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010539110A JP2010539110A (ja) | 2010-12-16 |
| JP2010539110A5 true JP2010539110A5 (OSRAM) | 2011-10-20 |
| JP5461402B2 JP5461402B2 (ja) | 2014-04-02 |
Family
ID=40130858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010524375A Expired - Fee Related JP5461402B2 (ja) | 2007-09-14 | 2008-09-02 | 置換三環式化合物およびその使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8524722B2 (OSRAM) |
| EP (1) | EP2212332B1 (OSRAM) |
| JP (1) | JP5461402B2 (OSRAM) |
| CA (1) | CA2699349C (OSRAM) |
| ES (1) | ES2396602T3 (OSRAM) |
| WO (1) | WO2009033581A1 (OSRAM) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5781934B2 (ja) | 2008-11-10 | 2015-09-24 | ナショナル ヘルス リサーチ インスティテューツ | チロシンキナーゼ阻害剤としての融合２環および３環ピリミジン化合物 |
| US8779192B2 (en) | 2009-05-14 | 2014-07-15 | Kolon Life Science, Inc. | Process of preparing an alkylamine derivative |
| US8221753B2 (en) | 2009-09-30 | 2012-07-17 | Tracon Pharmaceuticals, Inc. | Endoglin antibodies |
| KR20150089096A (ko) * | 2009-08-17 | 2015-08-04 | 트라콘 파마수티칼즈, 인코포레이티드 | 항엔도글린 항체 및 항ｖｅｇｆ 제제를 사용한 암 치료를 위한 병용 요법 |
| GB0915515D0 (en) * | 2009-09-04 | 2009-10-07 | Ucl Business Plc | Treatment of vasculoproliferative conditions |
| JP6042331B2 (ja) | 2010-07-23 | 2016-12-14 | プレジデント アンド フェローズ オブ ハーバード カレッジ | プロテアソーム活性を向上させる三環系化合物 |
| WO2012148889A1 (en) * | 2011-04-28 | 2012-11-01 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Inhibitors of human apurinic/apyrimidinic endonuclease 1 |
| CN102875535B (zh) * | 2011-07-12 | 2016-06-08 | 上海药明康德新药开发有限公司 | 1,5-[(取代)-甲桥]-四氢-1H-吡咯[1,2-c]-咪唑-3(2H)-酮衍生物及制备方法 |
| CA2861464C (en) | 2012-01-25 | 2018-03-06 | Proteostasis Therapeutics, Inc. | Proteasome activity modulating tricyclic compounds |
| AU2013202373B2 (en) * | 2012-01-25 | 2016-04-14 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| WO2013144191A1 (de) | 2012-03-29 | 2013-10-03 | Bayer Intellectual Property Gmbh | Substituierte 2 -amino - 3 - cyanopyridine als inhibitoren des natrium calcium austausches und ihre verwendung bei kardiovaskulären erkrankungen |
| US20150133426A1 (en) | 2012-05-21 | 2015-05-14 | Bayer Pharma Aktiengesellschaft | Substituted pyrrolopyrimidines |
| UA115789C2 (uk) | 2012-09-05 | 2017-12-26 | Трейкон Фармасутікалз, Інк. | Композиція антитіла до cd105 та її застосування |
| EP2961409A1 (en) * | 2013-02-26 | 2016-01-06 | Senex Biotechnology, Inc. | Inhibitors of cdk8/19 for use in treating estrogen receptor positive breast cancer |
| JP6087192B2 (ja) * | 2013-04-03 | 2017-03-01 | 京セラ株式会社 | 発電システムおよび発電システムの制御方法ならびに燃料電池 |
| CN104016983B (zh) * | 2013-10-08 | 2018-11-02 | 上海创诺制药有限公司 | 吡咯并三嗪类衍生物及其制法和用途 |
| WO2016077451A1 (en) | 2014-11-12 | 2016-05-19 | Tracon Pharmaceuticals, Inc. | Anti-endoglin antibodies and uses thereof |
| US9926375B2 (en) | 2014-11-12 | 2018-03-27 | Tracon Pharmaceuticals, Inc. | Anti-endoglin antibodies and uses thereof |
| CA2964140A1 (en) | 2014-12-02 | 2016-06-09 | Eli Lilly And Company | 1 -oxo-1,2-dihydroisoquinolin-7-yl-(5-substituted-thiophen-2-yl)-sulfonamide compounds, formulations containing those compounds, and their use as aicarft inhibitors in the treatment of cancers |
| CN104529800B (zh) * | 2014-12-08 | 2017-01-25 | 重庆威鹏药业有限公司 | 反式‑4‑二甲基氨基巴豆酸及盐的制备方法 |
| WO2016133888A1 (en) * | 2015-02-16 | 2016-08-25 | Biota Pharmaceuticals, Inc. | Compounds for treating respiratory syncytial virus infections |
| EP3111960B1 (en) * | 2015-07-03 | 2019-12-11 | Kyoto University | Nuclear medicine diagnostic imaging agent |
| CN108285421A (zh) * | 2018-01-26 | 2018-07-17 | 黑龙江鑫创生物科技开发有限公司 | 一种微通道反应器合成拉帕替尼中间体的方法 |
| EP3941905A1 (en) | 2019-03-19 | 2022-01-26 | Suvalent Therapeutics, Inc. | Sumo inhibitor compounds and uses thereof |
| US20220227765A1 (en) * | 2019-08-28 | 2022-07-21 | Ferro Therapeutics, Inc. | Pyrido-indole analogues as gpx4 inhibitors |
| CN117980309A (zh) * | 2021-08-05 | 2024-05-03 | 百时美施贵宝公司 | 用作her2抑制剂的三环稠合嘧啶化合物 |
| CN115724790A (zh) * | 2022-11-21 | 2023-03-03 | 安庆朗坤药业有限公司 | 一种n-(3-氯-4-(2-吡啶甲氧基)苯胺的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9127188D0 (en) | 1991-12-21 | 1992-02-19 | Smithkline Beecham Plc | Novel compounds |
| EP1323719A1 (en) | 1999-03-30 | 2003-07-02 | Nippon Soda Co., Ltd. | Thienopyrimidine compounds and salts thereof and process for the preparation of the same |
| AR028261A1 (es) * | 2000-03-28 | 2003-04-30 | Wyeth Corp | Inhibidores triciclicos de la proteina quinasa |
| WO2002088138A1 (en) | 2001-04-30 | 2002-11-07 | Bayer Corporation | Novel 4-amino-5,6-substituted thiopheno[2,3-d]pyrimidines |
| WO2003035653A1 (en) | 2001-10-26 | 2003-05-01 | Nippon Soda Co.,Ltd. | Pyridothienopyrimidine compound and salt thereof |
| JP4712702B2 (ja) * | 2003-07-24 | 2011-06-29 | バイエル・シエリング・フアーマ・アクチエンゲゼルシヤフト | 高増殖性疾患を処置するために有用な置換されたテトラヒドロベンゾチエノピリミジンアミン化合物 |
| US7427625B2 (en) | 2006-02-08 | 2008-09-23 | Janssen Pharmaceutica, N.V. | Substituted thiatriazaacenaphthylene-6-carbonitrile kinase inhibitors |
| JP2009527459A (ja) | 2006-02-23 | 2009-07-30 | 武田薬品工業株式会社 | 縮合窒素含有複素環化合物 |
| AR059901A1 (es) * | 2006-03-20 | 2008-05-07 | Bayer Pharmaceuticals Corp | Compuestos de tetrahidropiridotienopirimidina utiles para tratar o prevenir trastornos proliferativos celulares. |
-
2008
- 2008-09-02 JP JP2010524375A patent/JP5461402B2/ja not_active Expired - Fee Related
- 2008-09-02 CA CA2699349A patent/CA2699349C/en not_active Expired - Fee Related
- 2008-09-02 EP EP08785784A patent/EP2212332B1/en not_active Not-in-force
- 2008-09-02 US US12/678,288 patent/US8524722B2/en not_active Expired - Fee Related
- 2008-09-02 WO PCT/EP2008/007137 patent/WO2009033581A1/en not_active Ceased
- 2008-09-02 ES ES08785784T patent/ES2396602T3/es active Active
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