JP2015537001A5 - - Google Patents
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- JP2015537001A5 JP2015537001A5 JP2015542038A JP2015542038A JP2015537001A5 JP 2015537001 A5 JP2015537001 A5 JP 2015537001A5 JP 2015542038 A JP2015542038 A JP 2015542038A JP 2015542038 A JP2015542038 A JP 2015542038A JP 2015537001 A5 JP2015537001 A5 JP 2015537001A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims description 299
- 125000003545 alkoxy group Chemical group 0.000 claims description 203
- 150000001875 compounds Chemical class 0.000 claims description 107
- 125000001153 fluoro group Chemical group F* 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 239000012453 solvate Substances 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- -1 hydroxyl-carbonyl Chemical group 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 208000002193 Pain Diseases 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 13
- 238000010168 coupling process Methods 0.000 claims description 13
- 238000005859 coupling reaction Methods 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 6
- 201000009273 Endometriosis Diseases 0.000 claims description 6
- 208000000450 Pelvic Pain Diseases 0.000 claims description 6
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 6
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 6
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003566 oxetanyl group Chemical group 0.000 claims description 6
- 201000007094 prostatitis Diseases 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 101150111783 NTRK1 gene Proteins 0.000 claims description 2
- 206010029260 Neuroblastoma Diseases 0.000 claims description 2
- 206010033701 Papillary thyroid cancer Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- SIISYXWWQBUDOP-UHFFFAOYSA-N bis(1h-imidazol-2-yl)methanethione Chemical compound N=1C=CNC=1C(=S)C1=NC=CN1 SIISYXWWQBUDOP-UHFFFAOYSA-N 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 201000010989 colorectal carcinoma Diseases 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 230000008482 dysregulation Effects 0.000 claims description 2
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 208000010749 gastric carcinoma Diseases 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 201000002120 neuroendocrine carcinoma Diseases 0.000 claims description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 201000000498 stomach carcinoma Diseases 0.000 claims description 2
- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 claims description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 15
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261725925P | 2012-11-13 | 2012-11-13 | |
| US61/725,925 | 2012-11-13 | ||
| PCT/US2013/069951 WO2014078454A1 (en) | 2012-11-13 | 2013-11-13 | Bicyclic urea, thiourea, guanidine and cyanoguanidine compounds useful for the treatment of pain |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017211949A Division JP2018016649A (ja) | 2012-11-13 | 2017-11-01 | 疼痛の治療に有用な二環式尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015537001A JP2015537001A (ja) | 2015-12-24 |
| JP2015537001A5 true JP2015537001A5 (enExample) | 2016-12-08 |
| JP6345684B2 JP6345684B2 (ja) | 2018-06-20 |
Family
ID=49667614
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015542038A Expired - Fee Related JP6345684B2 (ja) | 2012-11-13 | 2013-11-13 | 疼痛の治療に有用な二環式尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 |
| JP2017211949A Withdrawn JP2018016649A (ja) | 2012-11-13 | 2017-11-01 | 疼痛の治療に有用な二環式尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017211949A Withdrawn JP2018016649A (ja) | 2012-11-13 | 2017-11-01 | 疼痛の治療に有用な二環式尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US10351575B2 (enExample) |
| EP (1) | EP2920166B1 (enExample) |
| JP (2) | JP6345684B2 (enExample) |
| KR (1) | KR102181913B1 (enExample) |
| CN (1) | CN104903310B (enExample) |
| AU (3) | AU2013344886B2 (enExample) |
| BR (1) | BR112015011010B1 (enExample) |
| CA (1) | CA2891334C (enExample) |
| CL (1) | CL2015001282A1 (enExample) |
| CR (1) | CR20150264A (enExample) |
| CY (1) | CY1118468T1 (enExample) |
| DK (1) | DK2920166T3 (enExample) |
| ES (1) | ES2610975T3 (enExample) |
| HR (1) | HRP20161613T1 (enExample) |
| HU (1) | HUE031557T2 (enExample) |
| IL (1) | IL238498A (enExample) |
| LT (1) | LT2920166T (enExample) |
| ME (1) | ME02879B (enExample) |
| MX (1) | MX366761B (enExample) |
| PH (1) | PH12015500938A1 (enExample) |
| PL (1) | PL2920166T3 (enExample) |
| PT (1) | PT2920166T (enExample) |
| RS (1) | RS55593B1 (enExample) |
| RU (1) | RU2664541C2 (enExample) |
| SG (1) | SG11201503731SA (enExample) |
| SI (1) | SI2920166T1 (enExample) |
| SM (2) | SMT201700034T1 (enExample) |
| UA (1) | UA117573C2 (enExample) |
| WO (1) | WO2014078454A1 (enExample) |
| ZA (1) | ZA201503580B (enExample) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2350075T1 (sl) | 2008-09-22 | 2014-06-30 | Array Biopharma, Inc. | Substituirane imidazo (1,2b)piridazinske spojine kot Trk kinazni inhibitorji |
| SG10201914059WA (en) | 2008-10-22 | 2020-03-30 | Array Biopharma Inc | Substituted pyrazolo[1,5-a]pyrimidine compounds as trk kinase inhibitors |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| EP2918588B1 (en) | 2010-05-20 | 2017-05-03 | Array Biopharma, Inc. | Macrocyclic compounds as TRK kinase inhibitors |
| SI2712358T1 (sl) | 2011-05-13 | 2017-03-31 | Array Biopharma, Inc. | Spojine pirolidinil sečnine, pirolidinil tiosečnine in pirolidinil gvanidina kot inhibitorji kinaze trka |
| US9828360B2 (en) | 2012-11-13 | 2017-11-28 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| US9809578B2 (en) | 2012-11-13 | 2017-11-07 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trkA kinase inhibitors |
| RU2664541C2 (ru) | 2012-11-13 | 2018-08-20 | Эррэй Биофарма Инк. | Бициклические соединения мочевины, тиомочевины, гуанидина и цианогуанидина, пригодные для лечения боли |
| WO2014078331A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(arylalkyl)-n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| ES2664331T3 (es) | 2012-11-13 | 2018-04-19 | Array Biopharma, Inc. | Compuestos de N-pirrolidinilo, N'-pirazolilurea, tiourea, guanidina y cianoguanidina como inhibidores de la cinasa Trka |
| WO2014078325A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(monocyclic aryl),n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
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| US9790178B2 (en) | 2012-11-13 | 2017-10-17 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078408A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078322A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| PT3154959T (pt) * | 2014-05-15 | 2019-09-24 | Array Biopharma Inc | 1-((3s,4r)-4-(3-fluorofenil)-1-(2-metoxietil)-pirrolidin-3-il)-3-(4-metil-3-(2-metilpirimidin-5-il)-1-fenil-1h-pirazol-5-il)ureia como inibidor da cinase trka |
| US10160727B2 (en) | 2014-08-06 | 2018-12-25 | Shionogi & Co., Ltd. | Heterocycle and carbocycle derivatives having TrkA inhibitory activity |
| US10799505B2 (en) | 2014-11-16 | 2020-10-13 | Array Biopharma, Inc. | Crystalline form of (S)-N-(5-((R)-2-(2,5-difluorophenyl)-pyrrolidin-1-yl)-pyrazolo[1,5-A]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide hydrogen sulfate |
| EP3330256B1 (en) | 2015-07-07 | 2021-06-16 | Shionogi & Co., Ltd. | HETEROCYCLIC DERIVATIVE HAVING TrkA-INHIBITING ACTIVITY |
| DK3322706T3 (da) | 2015-07-16 | 2021-02-01 | Array Biopharma Inc | Substituerede pyrazolo[1,5-a]pyridin-forbindelser som ret-kinaseinhibitorer |
| WO2017063509A1 (zh) | 2015-10-15 | 2017-04-20 | 江苏恒瑞医药股份有限公司 | 氧杂螺环类衍生物、其制备方法及其在医药上的应用 |
| JP2018534296A (ja) | 2015-10-26 | 2018-11-22 | ロクソ オンコロジー, インコーポレイテッドLoxo Oncology, Inc. | Trk阻害薬耐性がんにおける点変異およびそれに関連する方法 |
| WO2017135399A1 (ja) * | 2016-02-04 | 2017-08-10 | 塩野義製薬株式会社 | TrkA阻害活性を有する含窒素複素環および炭素環誘導体 |
| MX386416B (es) | 2016-04-04 | 2025-03-18 | Loxo Oncology Inc | Formulaciones liquidas de (s)-n-(5-((r)-2-(2,5-difluorofenil)-pirrolidin-1-il)-pirazolo[1,5-a]pirimidin-3-il)-3-hidroxipirrolidina-1-carboxamida. |
| US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
| RS65988B1 (sr) | 2016-04-04 | 2024-10-31 | Loxo Oncology Inc | Postupak lečenja pedijatrijskih karcinoma |
| HUE063877T2 (hu) | 2016-05-18 | 2024-02-28 | Loxo Oncology Inc | (S)-N-(5-((R)-2-(2,5-dlfluorofenil)pirolidin-1-il)plrazolo[1,5-A]pirimidin-3-il) -3-hidroxipirolidin-1-karboxamid elõállítása |
| EP3490607A4 (en) | 2016-07-29 | 2020-04-08 | Sunovion Pharmaceuticals Inc. | COMPOUNDS AND COMPOSITIONS, AND USES THEREOF |
| JP7187437B2 (ja) | 2016-07-29 | 2022-12-12 | サノビオン ファーマシューティカルズ インク | 化合物および組成物ならびにそれらの使用 |
| JOP20190077A1 (ar) | 2016-10-10 | 2019-04-09 | Array Biopharma Inc | مركبات بيرازولو [1، 5-a]بيريدين بها استبدال كمثبطات كيناز ret |
| TWI704148B (zh) | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ret激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| JOP20190092A1 (ar) | 2016-10-26 | 2019-04-25 | Array Biopharma Inc | عملية لتحضير مركبات بيرازولو[1، 5-a]بيريميدين وأملاح منها |
| WO2018079759A1 (ja) * | 2016-10-31 | 2018-05-03 | 塩野義製薬株式会社 | TrkA阻害活性を有する縮合複素環および縮合炭素環誘導体 |
| EP3824906A1 (en) | 2016-12-21 | 2021-05-26 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| CA3049136C (en) | 2017-01-18 | 2022-06-14 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrazine compounds as ret kinase inhibitors |
| WO2018136663A1 (en) | 2017-01-18 | 2018-07-26 | Array Biopharma, Inc. | Ret inhibitors |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| ES2992887T3 (en) * | 2017-04-27 | 2024-12-19 | Mochida Pharm Co Ltd | Novel tetrahydronaphthyl urea derivatives as inhibitors of tropomyosin receptor kinase a for the treatment of pain |
| SG11202000669VA (en) | 2017-08-02 | 2020-02-27 | Sunovion Pharmaceuticals Inc | Isochroman compounds and uses thereof |
| JP7134982B2 (ja) * | 2017-09-14 | 2022-09-12 | 持田製薬株式会社 | ジアルキルジヒドロナフタレン誘導体の製造方法 |
| WO2019054451A1 (ja) * | 2017-09-15 | 2019-03-21 | 持田製薬株式会社 | テトラヒドロナフチルウレア誘導体の結晶 |
| TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
| TWI812649B (zh) | 2017-10-10 | 2023-08-21 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
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| CA3087578C (en) | 2018-01-18 | 2023-08-08 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| CA3087354C (en) | 2018-01-18 | 2023-01-03 | Array Biopharma Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| EP3773725A1 (en) | 2018-03-29 | 2021-02-17 | Loxo Oncology Inc. | Treatment of trk-associated cancers |
| WO2019189717A1 (ja) * | 2018-03-30 | 2019-10-03 | 持田製薬株式会社 | テトラヒドロナフチルウレア誘導体の製造方法 |
| CN110467596A (zh) * | 2018-05-11 | 2019-11-19 | 持田制药株式会社 | 四氢萘基脲衍生物的晶体 |
| KR102545594B1 (ko) | 2018-07-31 | 2023-06-21 | 록쏘 온콜로지, 인코포레이티드 | (s)-5-아미노-3-(4-((5-플루오로-2-메톡시벤즈아미도)메틸)페닐)-1-(1,1,1-트리플루오로프로판-2-일)-1h-피라졸-4-카르복스아미드의 분무-건조된 분산물 및 제제 |
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