JP2016539153A5 - - Google Patents
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- Publication number
- JP2016539153A5 JP2016539153A5 JP2016536560A JP2016536560A JP2016539153A5 JP 2016539153 A5 JP2016539153 A5 JP 2016539153A5 JP 2016536560 A JP2016536560 A JP 2016536560A JP 2016536560 A JP2016536560 A JP 2016536560A JP 2016539153 A5 JP2016539153 A5 JP 2016539153A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazol
- cancer
- dihydro
- compound
- 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 86
- -1 imidazolial Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 230000003463 hyperproliferative effect Effects 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- JPSJKKOBBFBOSB-UHFFFAOYSA-N 6h-azulen-5-one Chemical compound O=C1CC=CC2=CC=CC2=C1 JPSJKKOBBFBOSB-UHFFFAOYSA-N 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003324 azulen-4-yl group Chemical group [H]C1=C([H])C2=C(*)C([H])=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- RHCIGLIHEMONQQ-MRXNPFEDSA-N 4-[(12S)-12-[(4-chlorophenyl)methyl]-9-oxa-2,3,13-triazatricyclo[6.4.1.04,13]trideca-1,3,5,7-tetraen-6-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound Cn1nccc1Nc1nccc(n1)-c1cc2OCC[C@H](Cc3ccc(Cl)cc3)c3nnc(c1)n23 RHCIGLIHEMONQQ-MRXNPFEDSA-N 0.000 claims description 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 201000002510 thyroid cancer Diseases 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 2
- 208000003200 Adenoma Diseases 0.000 claims description 2
- 206010001233 Adenoma benign Diseases 0.000 claims description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 claims description 2
- 208000008846 Neurocytoma Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 2
- 206010057644 Testis cancer Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 208000008385 Urogenital Neoplasms Diseases 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 2
- 210000002615 epidermis Anatomy 0.000 claims description 2
- 230000003325 follicular Effects 0.000 claims description 2
- 201000008361 ganglioneuroma Diseases 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 230000003780 keratinization Effects 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 208000003849 large cell carcinoma Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 208000025113 myeloid leukemia Diseases 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 208000028591 pheochromocytoma Diseases 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 206010038038 rectal cancer Diseases 0.000 claims description 2
- 201000001275 rectum cancer Diseases 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 208000000649 small cell carcinoma Diseases 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 201000003120 testicular cancer Diseases 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 208000037964 urogenital cancer Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 30
- 238000009472 formulation Methods 0.000 claims 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 108060006633 protein kinase Proteins 0.000 claims 1
- 238000000034 method Methods 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361912905P | 2013-12-06 | 2013-12-06 | |
| US61/912,905 | 2013-12-06 | ||
| PCT/US2014/068452 WO2015085007A1 (en) | 2013-12-06 | 2014-12-03 | Serine/threonine kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018211421A Division JP2019034970A (ja) | 2013-12-06 | 2018-11-09 | セリン／トレオニンキナーゼ阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016539153A JP2016539153A (ja) | 2016-12-15 |
| JP2016539153A5 true JP2016539153A5 (enExample) | 2018-01-11 |
| JP6449293B2 JP6449293B2 (ja) | 2019-01-09 |
Family
ID=52350292
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016536560A Active JP6449293B2 (ja) | 2013-12-06 | 2014-12-03 | セリン／トレオニンキナーゼ阻害剤 |
| JP2018211421A Pending JP2019034970A (ja) | 2013-12-06 | 2018-11-09 | セリン／トレオニンキナーゼ阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018211421A Pending JP2019034970A (ja) | 2013-12-06 | 2018-11-09 | セリン／トレオニンキナーゼ阻害剤 |
Country Status (23)
| Country | Link |
|---|---|
| US (5) | US9867833B2 (enExample) |
| EP (1) | EP3077401B1 (enExample) |
| JP (2) | JP6449293B2 (enExample) |
| KR (1) | KR102359759B1 (enExample) |
| CN (1) | CN106029672B (enExample) |
| AR (1) | AR098647A1 (enExample) |
| AU (1) | AU2014360455B2 (enExample) |
| BR (1) | BR112016012844B1 (enExample) |
| CA (1) | CA2932729C (enExample) |
| CL (1) | CL2016001368A1 (enExample) |
| CR (1) | CR20160309A (enExample) |
| EA (1) | EA031243B1 (enExample) |
| IL (1) | IL246017B (enExample) |
| MA (1) | MA39170B1 (enExample) |
| MX (1) | MX368443B (enExample) |
| MY (1) | MY176049A (enExample) |
| PE (1) | PE20160886A1 (enExample) |
| PH (1) | PH12016501071B1 (enExample) |
| SG (1) | SG11201604573WA (enExample) |
| TW (1) | TWI557126B (enExample) |
| UA (1) | UA120506C2 (enExample) |
| WO (1) | WO2015085007A1 (enExample) |
| ZA (1) | ZA201604461B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2884766A1 (en) | 2012-10-16 | 2014-04-24 | Daniel Jon Burdick | Serine/threonine kinase inhibitors |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| JP6449293B2 (ja) | 2013-12-06 | 2019-01-09 | ジェネンテック， インコーポレイテッド | セリン／トレオニンキナーゼ阻害剤 |
| KR102396710B1 (ko) * | 2013-12-30 | 2022-05-10 | 어레이 바이오파마 인크. | 세린/트레오닌 키나제 저해제 |
| KR102379517B1 (ko) | 2013-12-30 | 2022-03-25 | 제넨테크, 인크. | 세린/트레오닌 키나아제 억제제 |
| PE20181288A1 (es) | 2015-11-09 | 2018-08-07 | Astrazeneca Ab | Derivados de dihidroimidazopirazinona usados en el tratamiento del cancer |
| WO2017180581A1 (en) | 2016-04-15 | 2017-10-19 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| KR102811888B1 (ko) | 2017-09-08 | 2025-05-27 | 에프. 호프만-라 로슈 아게 | 암의 진단 및 치료 방법 |
| WO2019158579A1 (en) | 2018-02-13 | 2019-08-22 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| CA3140475A1 (en) * | 2019-06-06 | 2020-12-10 | Wei-Guo Su | Tricyclic compounds and their use |
| CN120682245A (zh) * | 2021-02-03 | 2025-09-23 | 江苏恒瑞医药股份有限公司 | 稠三环类细胞周期蛋白-依赖性激酶抑制剂及其制备方法和医药用途 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7413751B2 (en) | 2001-10-25 | 2008-08-19 | Depomed, Inc. | Methods of treatment using a gastric retained losartan dosage |
| CA2622571A1 (en) * | 2005-09-15 | 2007-03-22 | Painceptor Pharma Corporation | Methods of modulating neurotrophin-mediated activity |
| JP5442449B2 (ja) * | 2006-12-22 | 2014-03-12 | アステックス、セラピューティックス、リミテッド | 新規化合物 |
| DE602008003055D1 (de) * | 2007-05-31 | 2010-12-02 | Nerviano Medical Sciences Srl | Zyklokondensierte Azaindole, die als Kinase-Hemmer wirken |
| WO2012071336A1 (en) | 2010-11-23 | 2012-05-31 | Abbott Laboratories | Salts and crystalline forms of an apoptosis-inducing agent |
| BR112013021896A2 (pt) | 2011-02-28 | 2016-11-08 | Array Biopharma Inc | inibidores de serina/treonina cinase |
| CN103958502B (zh) | 2011-08-04 | 2016-02-10 | 阵列生物制药公司 | 作为丝氨酸/苏氨酸激酶抑制剂的喹唑啉化合物 |
| SI2820009T1 (en) | 2012-03-01 | 2018-05-31 | Array Biopharma, Inc. | Serine / Threonine kinase inhibitors |
| US9388171B2 (en) | 2012-08-27 | 2016-07-12 | Genetech, Inc. | Serine/threonine kinase inhibitors |
| CA2884766A1 (en) | 2012-10-16 | 2014-04-24 | Daniel Jon Burdick | Serine/threonine kinase inhibitors |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| JP6449293B2 (ja) | 2013-12-06 | 2019-01-09 | ジェネンテック， インコーポレイテッド | セリン／トレオニンキナーゼ阻害剤 |
| KR102396710B1 (ko) | 2013-12-30 | 2022-05-10 | 어레이 바이오파마 인크. | 세린/트레오닌 키나제 저해제 |
| KR102379517B1 (ko) | 2013-12-30 | 2022-03-25 | 제넨테크, 인크. | 세린/트레오닌 키나아제 억제제 |
| AR099989A1 (es) | 2014-04-09 | 2016-08-31 | Genentech Inc | Proceso de preparación de (s)-1-(1-(4-cloro-3-fluorofenil)-2-hidroxietil)-4-(2-((1-metil-1h-pirazol-5-il)amino)pirimidin-4-il)-2(1h)-ona y sus sales |
-
2014
- 2014-12-03 JP JP2016536560A patent/JP6449293B2/ja active Active
- 2014-12-03 PE PE2016000741A patent/PE20160886A1/es unknown
- 2014-12-03 UA UAA201607281A patent/UA120506C2/uk unknown
- 2014-12-03 MY MYPI2016001051A patent/MY176049A/en unknown
- 2014-12-03 BR BR112016012844-3A patent/BR112016012844B1/pt not_active IP Right Cessation
- 2014-12-03 CN CN201480074890.9A patent/CN106029672B/zh active Active
- 2014-12-03 AU AU2014360455A patent/AU2014360455B2/en not_active Ceased
- 2014-12-03 US US14/559,786 patent/US9867833B2/en active Active
- 2014-12-03 CA CA2932729A patent/CA2932729C/en active Active
- 2014-12-03 CR CR20160309A patent/CR20160309A/es unknown
- 2014-12-03 MA MA39170A patent/MA39170B1/fr unknown
- 2014-12-03 EP EP14827591.0A patent/EP3077401B1/en active Active
- 2014-12-03 EA EA201691177A patent/EA031243B1/ru not_active IP Right Cessation
- 2014-12-03 MX MX2016007352A patent/MX368443B/es active IP Right Grant
- 2014-12-03 SG SG11201604573WA patent/SG11201604573WA/en unknown
- 2014-12-03 WO PCT/US2014/068452 patent/WO2015085007A1/en not_active Ceased
- 2014-12-03 KR KR1020167017847A patent/KR102359759B1/ko not_active Expired - Fee Related
- 2014-12-05 TW TW103142501A patent/TWI557126B/zh not_active IP Right Cessation
- 2014-12-05 AR ARP140104549A patent/AR098647A1/es unknown
-
2016
- 2016-06-03 CL CL2016001368A patent/CL2016001368A1/es unknown
- 2016-06-05 IL IL24601716A patent/IL246017B/en active IP Right Grant
- 2016-06-06 PH PH12016501071A patent/PH12016501071B1/en unknown
- 2016-06-30 ZA ZA2016/04461A patent/ZA201604461B/en unknown
-
2017
- 2017-09-14 US US15/705,104 patent/US10278975B2/en active Active
-
2018
- 2018-11-09 JP JP2018211421A patent/JP2019034970A/ja active Pending
-
2019
- 2019-02-27 US US16/286,955 patent/US10517878B2/en active Active
- 2019-11-11 US US16/680,221 patent/US10842799B2/en active Active
-
2020
- 2020-10-20 US US17/075,380 patent/US11376260B2/en active Active
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