JP2017061526A5 - - Google Patents
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- JP2017061526A5 JP2017061526A5 JP2016224670A JP2016224670A JP2017061526A5 JP 2017061526 A5 JP2017061526 A5 JP 2017061526A5 JP 2016224670 A JP2016224670 A JP 2016224670A JP 2016224670 A JP2016224670 A JP 2016224670A JP 2017061526 A5 JP2017061526 A5 JP 2017061526A5
- Authority
- JP
- Japan
- Prior art keywords
- crystalline form
- salt
- pyrido
- fluorophenyl
- dihydro
- 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.)
- Pending
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- 150000003839 salts Chemical class 0.000 claims 29
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 26
- -1 1-methyl-1H-1,2,4-triazol-5-yl Chemical group 0.000 claims 19
- 238000000034 method Methods 0.000 claims 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 239000002904 solvent Substances 0.000 claims 10
- 238000000634 powder X-ray diffraction Methods 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 3
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- MWZDIEIXRBWPLG-UHFFFAOYSA-N 1-methyl-1,2,4-triazole Chemical compound CN1C=NC=N1 MWZDIEIXRBWPLG-UHFFFAOYSA-N 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000000113 differential scanning calorimetry Methods 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 238000001179 sorption measurement Methods 0.000 claims 2
- 238000001757 thermogravimetry curve Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims 1
- HWGQMRYQVZSGDQ-UHFFFAOYSA-N 7-fluoro-11-(4-fluorophenyl)-12-(2-methyl-1,2,4-triazol-3-yl)-2,3,10-triazatricyclo[7.3.1.05,13]trideca-1,5(13),6,8-tetraen-4-one Chemical compound CN1N=CN=C1C(C(N1)C=2C=CC(F)=CC=2)C2=NNC(=O)C3=C2C1=CC(F)=C3 HWGQMRYQVZSGDQ-UHFFFAOYSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 1
- 208000000172 Medulloblastoma Diseases 0.000 claims 1
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 238000002411 thermogravimetry Methods 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- CIPXAXVJQKKPPK-UHFFFAOYSA-N CC(CC(F)=C1)(C(C(C2c3ncn[n]3C)=O)=C1C(OC)=O)NC2c(cc1)ccc1F Chemical compound CC(CC(F)=C1)(C(C(C2c3ncn[n]3C)=O)=C1C(OC)=O)NC2c(cc1)ccc1F CIPXAXVJQKKPPK-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40547610P | 2010-10-21 | 2010-10-21 | |
| US61/405,476 | 2010-10-21 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013535079A Division JP2013540158A (ja) | 2010-10-21 | 2011-10-20 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018192521A Division JP2019034951A (ja) | 2010-10-21 | 2018-10-11 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017061526A JP2017061526A (ja) | 2017-03-30 |
| JP2017061526A5 true JP2017061526A5 (enExample) | 2017-07-13 |
Family
ID=44903424
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013535079A Pending JP2013540158A (ja) | 2010-10-21 | 2011-10-20 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
| JP2016224670A Pending JP2017061526A (ja) | 2010-10-21 | 2016-11-18 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
| JP2018192521A Withdrawn JP2019034951A (ja) | 2010-10-21 | 2018-10-11 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
| JP2020118281A Withdrawn JP2020169209A (ja) | 2010-10-21 | 2020-07-09 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
| JP2022123448A Withdrawn JP2022140637A (ja) | 2010-10-21 | 2022-08-02 | 結晶性（８Ｓ，９Ｒ）－５－フルオロ－８－（４－フルオロフェニル）－９－（１－メチル－１Ｈ－１，２，４－トリアゾール－５－イル）－８，９－ジヒドロ－２Ｈ－ピリド［４，３，２－ｄｅ］フタラジン－３（７Ｈ）－オントシレート塩 |
| JP2024130494A Pending JP2024150772A (ja) | 2010-10-21 | 2024-08-07 | 結晶性（８Ｓ，９Ｒ）－５－フルオロ－８－（４－フルオロフェニル）－９－（１－メチル－１Ｈ－１，２，４－トリアゾール－５－イル）－８，９－ジヒドロ－２Ｈ－ピリド［４，３，２－ｄｅ］フタラジン－３（７Ｈ）－オントシレート塩 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013535079A Pending JP2013540158A (ja) | 2010-10-21 | 2011-10-20 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018192521A Withdrawn JP2019034951A (ja) | 2010-10-21 | 2018-10-11 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
| JP2020118281A Withdrawn JP2020169209A (ja) | 2010-10-21 | 2020-07-09 | 結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩 |
| JP2022123448A Withdrawn JP2022140637A (ja) | 2010-10-21 | 2022-08-02 | 結晶性（８Ｓ，９Ｒ）－５－フルオロ－８－（４－フルオロフェニル）－９－（１－メチル－１Ｈ－１，２，４－トリアゾール－５－イル）－８，９－ジヒドロ－２Ｈ－ピリド［４，３，２－ｄｅ］フタラジン－３（７Ｈ）－オントシレート塩 |
| JP2024130494A Pending JP2024150772A (ja) | 2010-10-21 | 2024-08-07 | 結晶性（８Ｓ，９Ｒ）－５－フルオロ－８－（４－フルオロフェニル）－９－（１－メチル－１Ｈ－１，２，４－トリアゾール－５－イル）－８，９－ジヒドロ－２Ｈ－ピリド［４，３，２－ｄｅ］フタラジン－３（７Ｈ）－オントシレート塩 |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US8735392B2 (enExample) |
| EP (2) | EP2630146B1 (enExample) |
| JP (6) | JP2013540158A (enExample) |
| KR (4) | KR20190120458A (enExample) |
| CN (1) | CN103282365B (enExample) |
| AR (1) | AR083502A1 (enExample) |
| AU (2) | AU2011317040B2 (enExample) |
| BR (1) | BR112013009117A2 (enExample) |
| CA (1) | CA2814581C (enExample) |
| CY (1) | CY1123356T1 (enExample) |
| DK (1) | DK2630146T3 (enExample) |
| ES (1) | ES2816600T3 (enExample) |
| HU (1) | HUE051535T2 (enExample) |
| IL (2) | IL225789B (enExample) |
| MX (1) | MX362563B (enExample) |
| NZ (1) | NZ609490A (enExample) |
| PL (1) | PL2630146T3 (enExample) |
| PT (1) | PT2630146T (enExample) |
| RU (1) | RU2598606C3 (enExample) |
| SG (2) | SG10201710578TA (enExample) |
| SI (1) | SI2630146T1 (enExample) |
| TW (2) | TWI557123B (enExample) |
| WO (1) | WO2012054698A1 (enExample) |
| ZA (1) | ZA201302810B (enExample) |
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| EP2406389B1 (en) | 2009-03-13 | 2019-05-08 | Agios Pharmaceuticals, Inc. | Methods and compositions for cell-proliferation-related disorders |
| CA2944788C (en) | 2009-06-29 | 2023-08-22 | Agios Pharmaceuticals, Inc. | Compounds, and compositions thereof, which modulate pyruvate kinase m2, and methods of making same |
| CA2793835C (en) | 2009-10-21 | 2021-07-20 | Agios Pharmaceuticals, Inc. | Methods and compositions for cell-proliferation-related disorders |
| AU2011212928B2 (en) | 2010-02-03 | 2016-06-23 | Medivation Technologies Llc | Dihydropyridophthalazinone inhibitors of poly(ADP-ribose) polymerase (PARP) for use in treatment of diseases associated with a PTEN deficiency |
| MX340319B (es) * | 2010-02-08 | 2016-07-06 | Medivation Technologies Inc | Procesos para sintetizar derivados de dihidropiridoftalazinona. |
| ES2816600T3 (es) | 2010-10-21 | 2021-04-05 | Medivation Tech Llc | Sal tosilato de (8S,9R)-5-fluoro-8-(4-fluorofenil)-9-(1-metil-1H-1,2,4-triazol-5-il)-8,9-dihidro-2H-pirido[4,3,2-de]ftalazin-3(7H)-ona cristalina |
| KR101873543B1 (ko) | 2011-05-03 | 2018-07-02 | 아지오스 파마슈티컬스 아이엔씨. | 치료에 사용하기 위한 피루베이트 키나아제 활성제 |
| CN102827073A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
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