JP2018503649A5 - - Google Patents
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- Publication number
- JP2018503649A5 JP2018503649A5 JP2017539596A JP2017539596A JP2018503649A5 JP 2018503649 A5 JP2018503649 A5 JP 2018503649A5 JP 2017539596 A JP2017539596 A JP 2017539596A JP 2017539596 A JP2017539596 A JP 2017539596A JP 2018503649 A5 JP2018503649 A5 JP 2018503649A5
- Authority
- JP
- Japan
- Prior art keywords
- crystalline
- composition
- compound
- pyrrole
- chlorophenyl
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 70
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 56
- HLXHAXFWWGYXQW-UHFFFAOYSA-N 2-amino-2-(3-chlorophenyl)ethanol Chemical compound OCC(N)C1=CC=CC(Cl)=C1 HLXHAXFWWGYXQW-UHFFFAOYSA-N 0.000 claims description 36
- 241000124008 Mammalia Species 0.000 claims description 36
- -1 5-Chloro-2-isopropylaminopyridin-4-yl Chemical group 0.000 claims description 26
- 206010028980 Neoplasm Diseases 0.000 claims description 24
- 201000011510 cancer Diseases 0.000 claims description 24
- 239000012458 free base Substances 0.000 claims description 22
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 16
- 238000001157 Fourier transform infrared spectrum Methods 0.000 claims description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- 241000282412 Homo Species 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 12
- 241000288906 Primates Species 0.000 claims description 12
- 239000002246 antineoplastic agent Substances 0.000 claims description 12
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 12
- 244000144972 livestock Species 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 238000001228 spectrum Methods 0.000 claims description 8
- NCBIFXNQFURYON-UHFFFAOYSA-N 4-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-1h-pyrrole-2-carboxylic acid Chemical compound C1=NC(NC(C)C)=CC(C=2C=C(NC=2)C(O)=O)=C1Cl NCBIFXNQFURYON-UHFFFAOYSA-N 0.000 claims description 6
- KSERXGMCDHOLSS-UHFFFAOYSA-N n-[1-(3-chlorophenyl)-2-hydroxyethyl]-4-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-1h-pyrrole-2-carboxamide Chemical compound C1=NC(NC(C)C)=CC(C=2C=C(NC=2)C(=O)NC(CO)C=2C=C(Cl)C=CC=2)=C1Cl KSERXGMCDHOLSS-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 28
- TXSJHWLRGWAOSQ-UHFFFAOYSA-N N-[1-(3-chlorophenyl)-2-hydroxyethyl]-1-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]pyrrole-2-carboxamide Chemical compound CC(C)NC1=NC=C(Cl)C(=C1)N1C=CC=C1C(=O)NC(CO)C1=CC(Cl)=CC=C1 TXSJHWLRGWAOSQ-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 description 40
- KSERXGMCDHOLSS-LJQANCHMSA-N CC(C)Nc(nc1)cc(-c2c[nH]c(C(N[C@H](CO)c3cccc(Cl)c3)=O)c2)c1Cl Chemical compound CC(C)Nc(nc1)cc(-c2c[nH]c(C(N[C@H](CO)c3cccc(Cl)c3)=O)c2)c1Cl KSERXGMCDHOLSS-LJQANCHMSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562110449P | 2015-01-30 | 2015-01-30 | |
| US62/110,449 | 2015-01-30 | ||
| PCT/US2016/015829 WO2016123574A1 (en) | 2015-01-30 | 2016-01-29 | Crystalline forms of c21h22ci2n4o2 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020063198A Division JP2020100674A (ja) | 2015-01-30 | 2020-03-31 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018503649A JP2018503649A (ja) | 2018-02-08 |
| JP2018503649A5 true JP2018503649A5 (https=) | 2019-02-14 |
| JP7258460B2 JP7258460B2 (ja) | 2023-04-17 |
Family
ID=56544441
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017539596A Active JP7258460B2 (ja) | 2015-01-30 | 2016-01-29 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
| JP2020063198A Pending JP2020100674A (ja) | 2015-01-30 | 2020-03-31 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
| JP2021195403A Pending JP2022033866A (ja) | 2015-01-30 | 2021-12-01 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
| JP2023081553A Withdrawn JP2023096080A (ja) | 2015-01-30 | 2023-05-17 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
| JP2025050047A Pending JP2025089464A (ja) | 2015-01-30 | 2025-03-25 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020063198A Pending JP2020100674A (ja) | 2015-01-30 | 2020-03-31 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
| JP2021195403A Pending JP2022033866A (ja) | 2015-01-30 | 2021-12-01 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
| JP2023081553A Withdrawn JP2023096080A (ja) | 2015-01-30 | 2023-05-17 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
| JP2025050047A Pending JP2025089464A (ja) | 2015-01-30 | 2025-03-25 | Ｃ２１Ｈ２２Ｃｌ２Ｎ４Ｏ２の結晶形態 |
Country Status (12)
| Country | Link |
|---|---|
| US (6) | US9676746B2 (https=) |
| EP (2) | EP4477222A3 (https=) |
| JP (5) | JP7258460B2 (https=) |
| CN (2) | CN107406413A (https=) |
| AU (5) | AU2016211246B2 (https=) |
| CA (2) | CA2975048C (https=) |
| ES (1) | ES3009552T3 (https=) |
| HK (1) | HK1244274A1 (https=) |
| MX (1) | MX382289B (https=) |
| NZ (2) | NZ734041A (https=) |
| SG (2) | SG11201705924RA (https=) |
| WO (1) | WO2016123574A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015095842A2 (en) * | 2013-12-20 | 2015-06-25 | Biomed Valley Discoveries, Inc. | Methods and compositions for treating non-erk mapk pathway inhibitor-resistant cancers |
| AU2016211246B2 (en) * | 2015-01-30 | 2020-08-27 | Biomed Valley Discoveries, Inc. | Crystalline forms of C21H22CI2N4O2 |
| CA3008701A1 (en) * | 2016-01-27 | 2017-08-03 | Jiangsu Hengrui Medicine Co., Ltd. | Method for preparing pharmaceutical composition comprising quinoline derivative or salt thereof |
| WO2021020841A1 (en) * | 2019-07-29 | 2021-02-04 | Standigm Inc. | Composition for preventing or treating metabolic liver disease |
| WO2021102279A1 (en) * | 2019-11-20 | 2021-05-27 | University Of Kentucky Research Foundation | Anti-cancer compositions and methods |
| CN118765276A (zh) * | 2022-03-08 | 2024-10-11 | 甘李药业股份有限公司 | 氘代化合物，及其制备方法和应用 |
| IL315702A (en) * | 2022-03-24 | 2024-11-01 | Biomed Valley Discoveries Inc | Deuterated pyrrole inhibitory analogs of ERK, their synthesis and their intermediates |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4599331A (en) | 1984-12-24 | 1986-07-08 | Syntex (U.S.A.) Inc. | Etianic acids as antiangiogenics |
| JP2545522B2 (ja) | 1985-10-23 | 1996-10-23 | アルコン・ラボラトーリーズ，インコーポレイテッド | テトラヒドロ脈管形成抑制ステロイド |
| US4771042A (en) | 1985-11-25 | 1988-09-13 | The Upjohn Company | Inhibition of angiogenesis involving the coadministration of steroids with heparin or heparin fragments |
| EP0477195A1 (en) | 1989-06-16 | 1992-04-01 | The Upjohn Company | Suramin type compounds and angiostatic steroids to inhibit angiogenesis |
| WO1993010141A2 (en) | 1991-11-22 | 1993-05-27 | Alcon Laboratories, Inc. | Angiostatic steroids |
| HUP0202332A2 (en) | 2000-02-05 | 2002-10-28 | Vertex Pharma | Pyrazole compositions useful as inhibitors of erk |
| US7927613B2 (en) | 2002-02-15 | 2011-04-19 | University Of South Florida | Pharmaceutical co-crystal compositions |
| AU2003237121A1 (en) * | 2002-04-26 | 2003-11-10 | Vertex Pharmaceuticals Incorporated | Pyrrole derivatives as inhibitors of erk2 and uses thereof |
| LT3305776T (lt) | 2004-05-14 | 2020-01-10 | Vertex Pharmaceuticals Incorporated | Pirolo junginiai kaip erk baltymo kinazės inhibitoriai, ir farmacinės kompozicijos su šiais junginiais |
| US7582623B2 (en) | 2004-05-20 | 2009-09-01 | The Regents Of The University Of California | Photoactive metal nitrosyls for blood pressure regulation and cancer therapy |
| KR101125932B1 (ko) | 2006-12-06 | 2012-03-22 | 아이디유엔 파마슈티칼즈, 인코포레이티드 | (3ｓ)-3-［ｎ-(ｎ'-(2-ｔｅｒｔ-부틸페닐)옥사밀)알라니닐］아미노-5-(2',3',5',6'-테트라플루오로페녹시)-4-옥소펜탄산의 결정 형태 |
| CN104684555A (zh) * | 2012-09-18 | 2015-06-03 | 奥斯拜客斯制药有限公司 | 囊泡单胺转运体2的氘化苯并喹啉抑制剂的制剂药代动力学 |
| US9227969B2 (en) * | 2013-08-14 | 2016-01-05 | Novartis Ag | Compounds and compositions as inhibitors of MEK |
| AU2016211246B2 (en) * | 2015-01-30 | 2020-08-27 | Biomed Valley Discoveries, Inc. | Crystalline forms of C21H22CI2N4O2 |
-
2016
- 2016-01-29 AU AU2016211246A patent/AU2016211246B2/en active Active
- 2016-01-29 MX MX2017009696A patent/MX382289B/es unknown
- 2016-01-29 JP JP2017539596A patent/JP7258460B2/ja active Active
- 2016-01-29 CA CA2975048A patent/CA2975048C/en active Active
- 2016-01-29 SG SG11201705924RA patent/SG11201705924RA/en unknown
- 2016-01-29 EP EP24203987.3A patent/EP4477222A3/en active Pending
- 2016-01-29 ES ES16744240T patent/ES3009552T3/es active Active
- 2016-01-29 CA CA3218488A patent/CA3218488A1/en active Pending
- 2016-01-29 CN CN201680013774.5A patent/CN107406413A/zh active Pending
- 2016-01-29 SG SG10202101979TA patent/SG10202101979TA/en unknown
- 2016-01-29 US US15/011,377 patent/US9676746B2/en active Active
- 2016-01-29 WO PCT/US2016/015829 patent/WO2016123574A1/en not_active Ceased
- 2016-01-29 EP EP16744240.9A patent/EP3250562B1/en active Active
- 2016-01-29 CN CN202310821608.XA patent/CN116854662A/zh active Pending
- 2016-01-29 NZ NZ734041A patent/NZ734041A/en unknown
- 2016-01-29 HK HK18103713.0A patent/HK1244274A1/zh unknown
- 2016-01-29 NZ NZ772411A patent/NZ772411A/en unknown
-
2017
- 2017-05-17 US US15/598,181 patent/US10183927B2/en active Active
-
2018
- 2018-12-20 US US16/227,820 patent/US10738027B2/en active Active
-
2020
- 2020-03-31 JP JP2020063198A patent/JP2020100674A/ja active Pending
- 2020-07-07 US US16/922,365 patent/US11390600B2/en active Active
- 2020-10-20 AU AU2020257041A patent/AU2020257041C1/en active Active
-
2021
- 2021-12-01 JP JP2021195403A patent/JP2022033866A/ja active Pending
-
2022
- 2022-06-16 US US17/842,632 patent/US12187698B2/en active Active
- 2022-09-05 AU AU2022228084A patent/AU2022228084B2/en active Active
-
2023
- 2023-05-17 JP JP2023081553A patent/JP2023096080A/ja not_active Withdrawn
- 2023-10-25 AU AU2023254937A patent/AU2023254937B2/en active Active
-
2024
- 2024-11-26 US US18/960,604 patent/US20250084059A1/en active Pending
-
2025
- 2025-03-25 JP JP2025050047A patent/JP2025089464A/ja active Pending
- 2025-11-10 AU AU2025263912A patent/AU2025263912A1/en active Pending
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