JP2012512249A5 - - Google Patents
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- Publication number
- JP2012512249A5 JP2012512249A5 JP2011542264A JP2011542264A JP2012512249A5 JP 2012512249 A5 JP2012512249 A5 JP 2012512249A5 JP 2011542264 A JP2011542264 A JP 2011542264A JP 2011542264 A JP2011542264 A JP 2011542264A JP 2012512249 A5 JP2012512249 A5 JP 2012512249A5
- Authority
- JP
- Japan
- Prior art keywords
- cancer
- pyrazol
- methoxyphenyl
- aminopropoxy
- ylamino
- 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
- 150000001875 compounds Chemical class 0.000 claims description 12
- PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- DOTGPNHGTYJDEP-UHFFFAOYSA-N 5-[[5-[2-(3-aminopropoxy)-6-methoxyphenyl]-1h-pyrazol-3-yl]amino]pyrazine-2-carbonitrile Chemical compound COC1=CC=CC(OCCCN)=C1C1=CC(NC=2N=CC(=NC=2)C#N)=NN1 DOTGPNHGTYJDEP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 3
- SCYXSGJQMYDUFT-UHFFFAOYSA-N 5-[[5-[2-(3-aminopropoxy)-6-methoxyphenyl]-1h-pyrazol-3-yl]amino]pyrazine-2-carbonitrile;formic acid Chemical compound OC=O.COC1=CC=CC(OCCCN)=C1C1=CC(NC=2N=CC(=NC=2)C#N)=NN1 SCYXSGJQMYDUFT-UHFFFAOYSA-N 0.000 claims description 2
- WGCKOJKXQKKLQW-UHFFFAOYSA-N 5-[[5-[2-(3-aminopropoxy)-6-methoxyphenyl]-1h-pyrazol-3-yl]amino]pyrazine-2-carbonitrile;methanesulfonic acid Chemical compound CS(O)(=O)=O.COC1=CC=CC(OCCCN)=C1C1=CC(NC=2N=CC(=NC=2)C#N)=NN1 WGCKOJKXQKKLQW-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- -1 3-amino-propoxy Chemical group 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- OIXMUQLVDNPHNS-UHFFFAOYSA-N methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O OIXMUQLVDNPHNS-UHFFFAOYSA-N 0.000 description 7
- 239000002002 slurry Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13817608P | 2008-12-17 | 2008-12-17 | |
| US61/138,176 | 2008-12-17 | ||
| PCT/US2009/067437 WO2010077758A1 (en) | 2008-12-17 | 2009-12-10 | Compounds useful for inhibiting chk1 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012512249A JP2012512249A (ja) | 2012-05-31 |
| JP2012512249A5 true JP2012512249A5 (enExample) | 2013-01-31 |
| JP5705743B2 JP5705743B2 (ja) | 2015-04-22 |
Family
ID=42079067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011542264A Active JP5705743B2 (ja) | 2008-12-17 | 2009-12-10 | Ｃｈｋ１を阻害するために有用な化合物 |
Country Status (37)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8314108B2 (en) * | 2008-12-17 | 2012-11-20 | Eli Lilly And Company | 5-(5-(2-(3-aminopropoxy)-6-methoxyphenyl)-1H-pyrazol-3-ylamino)pyrazine-2-carbonitrile, pharmaceutically acceptable salts thereof, or solvate of salts |
| JO3145B1 (ar) * | 2010-11-08 | 2017-09-20 | Lilly Co Eli | مركبات مفيدة لتثبيط chk1 |
| GB201402277D0 (en) * | 2014-02-10 | 2014-03-26 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| TWI725041B (zh) * | 2015-07-23 | 2021-04-21 | 美商美國禮來大藥廠 | 用於治療神經母細胞瘤及/或軟組織肉瘤之chk1/2抑制劑 |
| AR106772A1 (es) * | 2015-12-07 | 2018-02-14 | Lilly Co Eli | Sales de (s)-lactato |
| JP6359197B2 (ja) * | 2015-12-15 | 2018-07-18 | イーライ リリー アンド カンパニー | がんの組合せ療法 |
| SI3411036T1 (sl) * | 2016-02-04 | 2022-03-31 | Pharmaengine, Inc. | 3,5-disubstituirani pirazoli, uporabni kot kontrolne točke inhibitorjev kinaze 1 (CHK1), ter njihovi pripravki in uporaba |
| CA3058457A1 (en) | 2017-03-31 | 2018-10-04 | Seattle Genetics, Inc. | Combinations of chk1- and wee1 - inhibitors |
| EP3461480A1 (en) | 2017-09-27 | 2019-04-03 | Onxeo | Combination of a dna damage response cell cycle checkpoint inhibitors and belinostat for treating cancer |
| CN112457306A (zh) | 2019-09-06 | 2021-03-09 | 上海瑛派药业有限公司 | 3,5-二取代吡唑化合物作为激酶抑制剂及其应用 |
| ES3014705T3 (en) * | 2019-11-29 | 2025-04-24 | Novaonco Js Therapeutics Co Ltd | Diazaindole derivative and use thereof as chk1 inhibitor |
| WO2021119236A1 (en) | 2019-12-10 | 2021-06-17 | Seagen Inc. | Preparation of a chk1 inhibitor compound |
| EP4253377A4 (en) * | 2020-11-30 | 2024-10-16 | Sumitomo Pharma Co., Ltd. | 5-HETEROARYL-1H-PYRAZOL-3-AMINE DERIVATIVE |
| US11564920B2 (en) | 2020-11-30 | 2023-01-31 | Sumitomo Pharma Co., Ltd. | 5-heteroaryl-1H-pyrazol-3-amine derivative |
| CN117715905A (zh) * | 2021-05-27 | 2024-03-15 | 无界生物公司 | 检查点激酶1（chk1）抑制剂及其用途 |
| GB202107924D0 (en) | 2021-06-03 | 2021-07-21 | Sentinel Oncology Ltd | A pharmaceutical salt |
| GB202107932D0 (en) | 2021-06-03 | 2021-07-21 | Sentinel Oncology Ltd | Preparation of a CHK1 Inhibitor Compound |
| EP4455134A4 (en) * | 2021-12-24 | 2025-10-08 | Sumitomo Pharma Co Ltd | 1H-PYRAZOLE-3-AMINE DERIVATIVE HAVING A BICYCLIC SKELETON |
| JP7546104B2 (ja) * | 2022-05-27 | 2024-09-05 | 住友ファーマ株式会社 | ５－ヘテロアリール－１ｈ－ピラゾール－３－アミン誘導体からなる医薬 |
| WO2023229032A1 (ja) * | 2022-05-27 | 2023-11-30 | 住友ファーマ株式会社 | 免疫チェックポイント阻害剤に対して治療抵抗性を示すがんの治療薬 |
| GB202213792D0 (en) | 2022-09-21 | 2022-11-02 | Benevolentai Bio Ltd | New compounds and method |
| GB202403910D0 (en) | 2024-03-19 | 2024-05-01 | Benovental Cambridge Ltd | New processes and intermediates for pharmaceutical products |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040034038A1 (en) * | 2002-08-13 | 2004-02-19 | Goaquan Li | Urea kinase inhibitors |
| JP2006528661A (ja) * | 2003-07-25 | 2006-12-21 | ファイザー・インク | アミノピラゾール化合物およびｃｈｋ１阻害剤としての使用 |
| WO2008117050A1 (en) | 2007-03-27 | 2008-10-02 | Astrazeneca Ab | Pyrazolyl-amino-substituted pyrazines and their use for the treatment of cancer |
| US20090270418A1 (en) * | 2008-01-09 | 2009-10-29 | Marianne Sloss | Pyrazole pyrazine amine compounds as kinase inhibitors, compositions thereof and methods of treatment therewith |
-
2009
- 2009-11-26 PA PA20098850801A patent/PA8850801A1/es unknown
- 2009-12-01 JO JO2009456A patent/JO2886B1/en active
- 2009-12-03 TW TW098141394A patent/TWI436996B/zh active
- 2009-12-03 AR ARP090104673A patent/AR074471A1/es not_active Application Discontinuation
- 2009-12-10 KR KR1020117013801A patent/KR101301777B1/ko not_active Expired - Fee Related
- 2009-12-10 CN CN200980150018.7A patent/CN102245597B/zh active Active
- 2009-12-10 SG SG2011044401A patent/SG172222A1/en unknown
- 2009-12-10 SI SI200930559T patent/SI2379532T1/sl unknown
- 2009-12-10 JP JP2011542264A patent/JP5705743B2/ja active Active
- 2009-12-10 HR HRP20130167AT patent/HRP20130167T1/hr unknown
- 2009-12-10 MY MYPI2011002767A patent/MY156998A/en unknown
- 2009-12-10 NZ NZ593440A patent/NZ593440A/xx not_active IP Right Cessation
- 2009-12-10 BR BRPI0922468-8A patent/BRPI0922468A2/pt active Search and Examination
- 2009-12-10 ES ES09768586T patent/ES2401558T3/es active Active
- 2009-12-10 PL PL09768586T patent/PL2379532T3/pl unknown
- 2009-12-10 WO PCT/US2009/067437 patent/WO2010077758A1/en not_active Ceased
- 2009-12-10 UA UAA201107564A patent/UA101998C2/ru unknown
- 2009-12-10 PE PE2011001140A patent/PE20120077A1/es active IP Right Grant
- 2009-12-10 PT PT97685861T patent/PT2379532E/pt unknown
- 2009-12-10 CA CA2746423A patent/CA2746423C/en not_active Expired - Fee Related
- 2009-12-10 DK DK09768586.1T patent/DK2379532T3/da active
- 2009-12-10 AU AU2009333433A patent/AU2009333433B2/en not_active Ceased
- 2009-12-10 MX MX2011006603A patent/MX2011006603A/es active IP Right Grant
- 2009-12-10 RS RS20130153A patent/RS52739B/sr unknown
- 2009-12-10 EP EP09768586A patent/EP2379532B1/en active Active
- 2009-12-10 EA EA201170834A patent/EA018118B1/ru not_active IP Right Cessation
-
2011
- 2011-05-26 IL IL213160A patent/IL213160A/en not_active IP Right Cessation
- 2011-05-27 ZA ZA2011/03946A patent/ZA201103946B/en unknown
- 2011-06-01 HN HN2011001446A patent/HN2011001446A/es unknown
- 2011-06-10 TN TN2011000298A patent/TN2011000298A1/fr unknown
- 2011-06-13 DO DO2011000185A patent/DOP2011000185A/es unknown
- 2011-06-14 MA MA33944A patent/MA32901B1/fr unknown
- 2011-06-15 CO CO11074829A patent/CO6382122A2/es active IP Right Grant
- 2011-06-16 CL CL2011001463A patent/CL2011001463A1/es unknown
- 2011-06-16 EC EC2011011136A patent/ECSP11011136A/es unknown
- 2011-06-17 CR CR20110339A patent/CR20110339A/es unknown
-
2013
- 2013-04-11 CY CY20131100305T patent/CY1113930T1/el unknown
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