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 (https=) | 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 |
| HK1254687A1 (zh) * | 2015-12-15 | 2019-07-26 | Eli Lilly And Company | 用於癌症的联合疗法 |
| HRP20220351T1 (hr) * | 2016-02-04 | 2022-05-13 | Pharmaengine, Inc. | 3,5-disupstituirani pirazoli korisni kao inhibitori kinaze 1 kontrolne točke (chk1), i njihove pripreme i primjene |
| US20200108074A1 (en) | 2017-03-31 | 2020-04-09 | 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 |
| US11634424B2 (en) | 2019-11-29 | 2023-04-25 | Medshine Discovery Inc. | Diazaindole derivative and use thereof as CHK1 inhibitor |
| WO2021119236A1 (en) | 2019-12-10 | 2021-06-17 | Seagen Inc. | Preparation of a chk1 inhibitor compound |
| US11564920B2 (en) | 2020-11-30 | 2023-01-31 | Sumitomo Pharma Co., Ltd. | 5-heteroaryl-1H-pyrazol-3-amine derivative |
| AU2021389190A1 (en) | 2020-11-30 | 2023-06-29 | Sumitomo Pharma Co., Ltd. | 5-heteroaryl-1h-pyrazol-3-amine derivative |
| CA3219348A1 (en) | 2021-05-27 | 2022-12-01 | Anthony B. Pinkerton | Checkpoint kinase 1 (chk1) inhibitors and uses thereof |
| 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 |
| US20250129049A1 (en) * | 2021-12-24 | 2025-04-24 | Sumitomo Pharma Co., Ltd. | 1h-pyrazole-3-amine derivative having bicyclic backbone |
| US20250352541A1 (en) * | 2022-05-27 | 2025-11-20 | Sumitomo Pharma Co., Ltd. | Therapeutic for cancer refractory to immune checkpoint inhibitor |
| 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 |
| 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 |
| MXPA06000933A (es) * | 2003-07-25 | 2006-03-30 | Pfizer | Compuestos de aminopirazol y uso como inhibidores de chk1. |
| 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 AR ARP090104673A patent/AR074471A1/es not_active Application Discontinuation
- 2009-12-03 TW TW098141394A patent/TWI436996B/zh active
- 2009-12-10 MX MX2011006603A patent/MX2011006603A/es active IP Right Grant
- 2009-12-10 AU AU2009333433A patent/AU2009333433B2/en not_active Ceased
- 2009-12-10 UA UAA201107564A patent/UA101998C2/ru unknown
- 2009-12-10 RS RS20130153A patent/RS52739B/sr unknown
- 2009-12-10 BR BRPI0922468-8A patent/BRPI0922468A2/pt active Search and Examination
- 2009-12-10 HR HRP20130167AT patent/HRP20130167T1/hr unknown
- 2009-12-10 JP JP2011542264A patent/JP5705743B2/ja active Active
- 2009-12-10 SI SI200930559T patent/SI2379532T1/sl unknown
- 2009-12-10 KR KR1020117013801A patent/KR101301777B1/ko not_active Expired - Fee Related
- 2009-12-10 NZ NZ593440A patent/NZ593440A/xx not_active IP Right Cessation
- 2009-12-10 WO PCT/US2009/067437 patent/WO2010077758A1/en not_active Ceased
- 2009-12-10 DK DK09768586.1T patent/DK2379532T3/da active
- 2009-12-10 PE PE2011001140A patent/PE20120077A1/es active IP Right Grant
- 2009-12-10 SG SG2011044401A patent/SG172222A1/en unknown
- 2009-12-10 MY MYPI2011002767A patent/MY156998A/en unknown
- 2009-12-10 CA CA2746423A patent/CA2746423C/en not_active Expired - Fee Related
- 2009-12-10 EP EP09768586A patent/EP2379532B1/en active Active
- 2009-12-10 PT PT97685861T patent/PT2379532E/pt unknown
- 2009-12-10 CN CN200980150018.7A patent/CN102245597B/zh active Active
- 2009-12-10 EA EA201170834A patent/EA018118B1/ru not_active IP Right Cessation
- 2009-12-10 ES ES09768586T patent/ES2401558T3/es active Active
- 2009-12-10 PL PL09768586T patent/PL2379532T3/pl unknown
-
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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