JP2014509322A5 - - Google Patents
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- Publication number
- JP2014509322A5 JP2014509322A5 JP2013555610A JP2013555610A JP2014509322A5 JP 2014509322 A5 JP2014509322 A5 JP 2014509322A5 JP 2013555610 A JP2013555610 A JP 2013555610A JP 2013555610 A JP2013555610 A JP 2013555610A JP 2014509322 A5 JP2014509322 A5 JP 2014509322A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- formula
- pharmaceutically acceptable
- acceptable salt
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 214
- 125000003545 alkoxy group Chemical group 0.000 claims description 144
- 150000001875 compounds Chemical class 0.000 claims description 125
- 150000003839 salts Chemical class 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 125000001153 fluoro group Chemical group F* 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 36
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- -1 tetrahydropyranyloxy Chemical group 0.000 claims description 26
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 24
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000006242 amine protecting group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 206010025135 lupus erythematosus Diseases 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 101100297651 Mus musculus Pim2 gene Proteins 0.000 claims description 2
- 101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- PBVFROWIWWGIFK-UHFFFAOYSA-N fluoromethyl-(2-hydroxyethyl)-dimethylazanium Chemical compound FC[N+](C)(C)CCO PBVFROWIWWGIFK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 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 3
- 239000002904 solvent Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 CC(*)(*)N1C(*)C(*)C(*)(*)C1 Chemical compound CC(*)(*)N1C(*)C(*)C(*)(*)C1 0.000 description 5
- 101100297652 Coturnix japonica PIM3 gene Proteins 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161446902P | 2011-02-25 | 2011-02-25 | |
| US61/446,902 | 2011-02-25 | ||
| PCT/US2012/026572 WO2012154274A1 (en) | 2011-02-25 | 2012-02-24 | Triazolopyridine compounds as pim kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016032675A Division JP2016106118A (ja) | 2011-02-25 | 2016-02-24 | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014509322A JP2014509322A (ja) | 2014-04-17 |
| JP2014509322A5 true JP2014509322A5 (OSRAM) | 2015-04-09 |
| JP6039585B2 JP6039585B2 (ja) | 2016-12-07 |
Family
ID=46000320
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013555610A Expired - Fee Related JP6039585B2 (ja) | 2011-02-25 | 2012-02-24 | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 |
| JP2016032675A Withdrawn JP2016106118A (ja) | 2011-02-25 | 2016-02-24 | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016032675A Withdrawn JP2016106118A (ja) | 2011-02-25 | 2016-02-24 | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US8889704B2 (OSRAM) |
| EP (1) | EP2678329B1 (OSRAM) |
| JP (2) | JP6039585B2 (OSRAM) |
| KR (1) | KR101940338B1 (OSRAM) |
| CN (1) | CN103492377B (OSRAM) |
| AR (1) | AR085489A1 (OSRAM) |
| AU (1) | AU2012254082B2 (OSRAM) |
| BR (1) | BR112013021675A2 (OSRAM) |
| CA (1) | CA2828269C (OSRAM) |
| CL (1) | CL2013002446A1 (OSRAM) |
| CO (1) | CO6771441A2 (OSRAM) |
| CR (1) | CR20130460A (OSRAM) |
| CY (1) | CY1117197T1 (OSRAM) |
| DK (1) | DK2678329T3 (OSRAM) |
| ES (1) | ES2563152T3 (OSRAM) |
| HR (1) | HRP20160134T1 (OSRAM) |
| HU (1) | HUE027675T2 (OSRAM) |
| IL (1) | IL228108A (OSRAM) |
| ME (1) | ME02365B (OSRAM) |
| MX (1) | MX339899B (OSRAM) |
| PH (1) | PH12013501754A1 (OSRAM) |
| PL (1) | PL2678329T3 (OSRAM) |
| RS (1) | RS54586B1 (OSRAM) |
| RU (1) | RU2598846C2 (OSRAM) |
| SG (1) | SG192944A1 (OSRAM) |
| SI (1) | SI2678329T1 (OSRAM) |
| SM (1) | SMT201600052B (OSRAM) |
| TW (1) | TWI529170B (OSRAM) |
| UA (1) | UA111075C2 (OSRAM) |
| UY (1) | UY33924A (OSRAM) |
| WO (1) | WO2012154274A1 (OSRAM) |
| ZA (1) | ZA201306997B (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3409278B8 (en) | 2011-07-21 | 2020-11-04 | Sumitomo Dainippon Pharma Oncology, Inc. | Heterocyclic protein kinase inhibitors |
| CA2860810A1 (en) * | 2012-04-25 | 2013-10-31 | F. Hoffmann-La Roche Ag | (3,4-dichloro-phenyl)-((s)-3-propyl-pyrrolidin-3-yl)-methanone hydrochloride and manufacturing processes |
| JP6437452B2 (ja) | 2013-01-14 | 2018-12-12 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉｍキナーゼ阻害剤として有用な二環式芳香族カルボキサミド化合物 |
| ME03780B (me) | 2013-01-15 | 2021-04-20 | Incyte Holdings Corp | Jedinjenja tiazolkarboksamida i piridinkarboksamida korisna kao inhibitori pim kinaze |
| EA201690458A1 (ru) | 2013-08-23 | 2016-07-29 | Инсайт Корпорейшн | Фуро- и тиенопиридинкарбоксамиды, используемые в качестве ингибиторов pim-киназы |
| US9822124B2 (en) | 2014-07-14 | 2017-11-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as Pim kinase inhibitors |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| AR105967A1 (es) | 2015-09-09 | 2017-11-29 | Incyte Corp | Sales de un inhibidor de pim quinasa |
| WO2017059251A1 (en) | 2015-10-02 | 2017-04-06 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| MA45122A (fr) * | 2016-05-24 | 2019-04-10 | Constellation Pharmaceuticals Inc | Inhibiteurs hétérocycliques de cbp/ep300 et leur utilisation dans le traitement du cancer |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| US20210113562A1 (en) | 2018-04-13 | 2021-04-22 | Sumitomo Dainippon Pharma Oncology, Inc. | Pim kinase inhibitors for treatment of myeloproliferative neoplasms and fibrosis associated with cancer |
| EP3825303A4 (en) | 2018-07-17 | 2022-07-06 | Nippon Chemiphar Co., Ltd. | T-type calcium channel blocker |
| CN109053526A (zh) * | 2018-08-13 | 2018-12-21 | 南通大学 | 一种（3r，4s）-4-甲基吡咯烷-3-基氨基甲酸叔丁酯盐酸盐的化学合成方法 |
| CN108912032A (zh) * | 2018-08-13 | 2018-11-30 | 南通大学 | 一种（3s，4r）-4-甲基吡咯烷-3-基氨基甲醇叔丁酯盐酸盐的化学合成方法 |
| WO2020157709A1 (en) | 2019-02-01 | 2020-08-06 | Pfizer Inc. | Combination of a cdk inhibitor and a pim inhibitor |
| CA3127502A1 (en) | 2019-02-12 | 2020-08-20 | Sumitomo Dainippon Pharma Oncology, Inc. | Formulations comprising heterocyclic protein kinase inhibitors |
| CN113195469B (zh) * | 2019-02-19 | 2024-05-24 | 四川科伦博泰生物医药股份有限公司 | 含氮并环化合物、其制备方法及用途 |
| US20220226299A1 (en) | 2019-03-29 | 2022-07-21 | Nippon Chemiphar Co., Ltd. | Use of t-type calcium channel blocker for treating pruritus |
| CN111171023B (zh) * | 2020-01-10 | 2021-12-21 | 中国药科大学 | 一种具有Pim1抑制活性的化合物及其制备方法与医药用途 |
| EP4611753A1 (en) | 2022-10-31 | 2025-09-10 | Sumitomo Pharma America, Inc. | Pim1 inhibitor for treating myeloproliferative neoplasms |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2388593A1 (en) | 1999-11-12 | 2001-05-17 | Neurogen Corporation | Bicyclic and tricyclic heteroaromatic compounds |
| UA75055C2 (uk) * | 1999-11-30 | 2006-03-15 | Пфайзер Продактс Інк. | Похідні бензоімідазолу, що використовуються як антипроліферативний засіб, фармацевтична композиція на їх основі |
| CN1308327C (zh) | 2000-04-27 | 2007-04-04 | 安斯泰来制药有限公司 | 咪唑并吡啶衍生物 |
| DE10038019A1 (de) | 2000-08-04 | 2002-02-14 | Bayer Ag | Substituierte Triazolopyrid(az)ine |
| KR20030080087A (ko) | 2001-03-09 | 2003-10-10 | 화이자 프로덕츠 인코포레이티드 | 항염증제로서의 트리아졸로피리딘 |
| US7227006B2 (en) | 2002-01-19 | 2007-06-05 | Sanofi-Aventis Deutschland Gmbh | PIM-3 kinase as a target for type 2 diabetes mellitus |
| RU2005122484A (ru) | 2002-12-18 | 2006-01-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Композиции, используемые в качестве ингибиторов протеинкиназ |
| WO2004058749A1 (en) | 2002-12-18 | 2004-07-15 | Vertex Pharmaceuticals Incorporated | Benzisoxazole derivatives useful as inhibitors of protein kinases |
| WO2005028624A2 (en) | 2003-09-15 | 2005-03-31 | Plexxikon, Inc. | Molecular scaffolds for kinase ligand development |
| US20050256309A1 (en) | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US20090215817A1 (en) | 2004-08-18 | 2009-08-27 | Pfizer Inc | Novel Triazolopyridine Compounds for the Treatment of Inflammation |
| CA2586796A1 (en) | 2004-12-01 | 2006-06-08 | Laboratoires Serono S.A. | [1,2,4]triazolo[4,3-a]pyridine derivatives for the treatment of hyperproliferative diseases |
| JP5238506B2 (ja) | 2005-10-06 | 2013-07-17 | エグゼリクシス， インコーポレイテッド | Ｐｉｍ−１および／またはｐｉｍ−３のピリドピリミジノンインヒビター |
| JP2009523820A (ja) | 2006-01-23 | 2009-06-25 | アミラ ファーマシューティカルス，インコーポレーテッド | ５−リポキシゲナーゼの三環系抑制剤 |
| WO2007145921A1 (en) | 2006-06-06 | 2007-12-21 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| MX2009004700A (es) | 2006-11-06 | 2009-05-15 | Supergen Inc | Derivados de imidazo[1,2-b]piridazin y pirazolo[1,5-a] pirimidina y su uso como inhibidores de proteina cinasa. |
| WO2008082839A2 (en) | 2006-12-29 | 2008-07-10 | Abbott Laboratories | Pim kinase inhibitors as cancer chemotherapeutics |
| KR20090127902A (ko) * | 2007-03-02 | 2009-12-14 | 쉐링 코포레이션 | 벤즈이미다졸 유도체 및 이의 사용방법 |
| JP2010522765A (ja) * | 2007-03-28 | 2010-07-08 | アレイ バイオファーマ、インコーポレイテッド | 受容体チロシンキナーゼとしてのイミダゾ［１，２−ａ］ピリジン化合物 |
| EP2137184B1 (en) * | 2007-04-03 | 2013-05-08 | Array Biopharma, Inc. | Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors |
| AR071717A1 (es) | 2008-05-13 | 2010-07-07 | Array Biopharma Inc | Pirrolo[2,3-b]piridinas inhibidoras de quinasas chk1 y chk2,composiciones farmaceuticas que las contienen,proceso para prepararlas y uso de las mismas en el tratamiento y prevencion del cancer. |
| WO2010022081A1 (en) * | 2008-08-19 | 2010-02-25 | Array Biopharma Inc. | Triazolopyridine compounds as pim kinase inhibitors |
| TWI496779B (zh) * | 2008-08-19 | 2015-08-21 | Array Biopharma Inc | 作為ｐｉｍ激酶抑制劑之三唑吡啶化合物 |
| US20110184013A1 (en) * | 2008-10-01 | 2011-07-28 | Shelley Allen | Imidazo[1,2-a]Pyridine Compounds As Receptor Tyrosine Kinase Inhibitors |
| AU2010229142A1 (en) * | 2009-03-23 | 2011-10-13 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
-
2012
- 2012-02-24 RS RS20160095A patent/RS54586B1/sr unknown
- 2012-02-24 WO PCT/US2012/026572 patent/WO2012154274A1/en not_active Ceased
- 2012-02-24 PL PL12716770T patent/PL2678329T3/pl unknown
- 2012-02-24 EP EP12716770.8A patent/EP2678329B1/en active Active
- 2012-02-24 KR KR1020137025297A patent/KR101940338B1/ko not_active Expired - Fee Related
- 2012-02-24 SI SI201230453A patent/SI2678329T1/sl unknown
- 2012-02-24 UY UY0001033924A patent/UY33924A/es not_active Application Discontinuation
- 2012-02-24 AU AU2012254082A patent/AU2012254082B2/en not_active Ceased
- 2012-02-24 ME MEP-2016-35A patent/ME02365B/me unknown
- 2012-02-24 RU RU2013143292/04A patent/RU2598846C2/ru not_active IP Right Cessation
- 2012-02-24 HR HRP20160134TT patent/HRP20160134T1/hr unknown
- 2012-02-24 BR BR112013021675A patent/BR112013021675A2/pt not_active Application Discontinuation
- 2012-02-24 US US14/001,657 patent/US8889704B2/en not_active Expired - Fee Related
- 2012-02-24 JP JP2013555610A patent/JP6039585B2/ja not_active Expired - Fee Related
- 2012-02-24 AR ARP120100626A patent/AR085489A1/es active IP Right Grant
- 2012-02-24 SG SG2013064324A patent/SG192944A1/en unknown
- 2012-02-24 CA CA2828269A patent/CA2828269C/en not_active Expired - Fee Related
- 2012-02-24 UA UAA201311350A patent/UA111075C2/uk unknown
- 2012-02-24 MX MX2013009820A patent/MX339899B/es active IP Right Grant
- 2012-02-24 HU HUE12716770A patent/HUE027675T2/en unknown
- 2012-02-24 DK DK12716770.8T patent/DK2678329T3/da active
- 2012-02-24 PH PH1/2013/501754A patent/PH12013501754A1/en unknown
- 2012-02-24 ES ES12716770.8T patent/ES2563152T3/es active Active
- 2012-02-24 CN CN201280020416.9A patent/CN103492377B/zh not_active Expired - Fee Related
- 2012-02-29 TW TW101106629A patent/TWI529170B/zh not_active IP Right Cessation
-
2013
- 2013-08-23 CL CL2013002446A patent/CL2013002446A1/es unknown
- 2013-08-25 IL IL228108A patent/IL228108A/en active IP Right Grant
- 2013-09-11 CR CR20130460A patent/CR20130460A/es unknown
- 2013-09-17 ZA ZA2013/06997A patent/ZA201306997B/en unknown
- 2013-09-18 CO CO13222097A patent/CO6771441A2/es unknown
-
2016
- 2016-02-16 CY CY20161100127T patent/CY1117197T1/el unknown
- 2016-02-22 SM SM201600052T patent/SMT201600052B/xx unknown
- 2016-02-24 JP JP2016032675A patent/JP2016106118A/ja not_active Withdrawn
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