JP2016527279A5 - - Google Patents
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- Publication number
- JP2016527279A5 JP2016527279A5 JP2016531940A JP2016531940A JP2016527279A5 JP 2016527279 A5 JP2016527279 A5 JP 2016527279A5 JP 2016531940 A JP2016531940 A JP 2016531940A JP 2016531940 A JP2016531940 A JP 2016531940A JP 2016527279 A5 JP2016527279 A5 JP 2016527279A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- amino
- pyridin
- use according
- isolated
- 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
- 101000599886 Homo sapiens Isocitrate dehydrogenase [NADP], mitochondrial Proteins 0.000 claims description 21
- 102100037845 Isocitrate dehydrogenase [NADP], mitochondrial Human genes 0.000 claims description 21
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 20
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 15
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 13
- 206010025323 Lymphomas Diseases 0.000 claims description 12
- 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims description 10
- 108700028369 Alleles Proteins 0.000 claims description 7
- 206010008583 Chloroma Diseases 0.000 claims description 6
- 208000034578 Multiple myelomas Diseases 0.000 claims description 6
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 6
- 201000005987 myeloid sarcoma Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 15
- 238000000634 powder X-ray diffraction Methods 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 14
- 239000013078 crystal Substances 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 9
- 201000005787 hematologic cancer Diseases 0.000 claims 8
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
- 230000000750 progressive effect Effects 0.000 claims 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- URUBZXVIOILFLM-UHFFFAOYSA-N CC(C)(CNc1nc(Nc2ccnc(c2)C(F)(F)F)nc(n1)-c1cccc(n1)C(F)(F)F)OS(C)(=O)=O Chemical compound CC(C)(CNc1nc(Nc2ccnc(c2)C(F)(F)F)nc(n1)-c1cccc(n1)C(F)(F)F)OS(C)(=O)=O URUBZXVIOILFLM-UHFFFAOYSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
- 239000012458 free base Substances 0.000 claims 5
- DYLUUSLLRIQKOE-UHFFFAOYSA-N enasidenib Chemical compound N=1C(C=2N=C(C=CC=2)C(F)(F)F)=NC(NCC(C)(O)C)=NC=1NC1=CC=NC(C(F)(F)F)=C1 DYLUUSLLRIQKOE-UHFFFAOYSA-N 0.000 claims 4
- 239000006186 oral dosage form Substances 0.000 claims 4
- 239000000843 powder Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- SWWHCQCMVCPLEQ-UHFFFAOYSA-N propan-2-yl methanesulfonate Chemical compound CC(C)OS(C)(=O)=O SWWHCQCMVCPLEQ-UHFFFAOYSA-N 0.000 claims 2
- -1 4- [ 6- (Trifluoromethyl) pyridin-2-yl] -6-{[2- (trifluoromethyl) pyridin-4-yl] amino} -1,3,5-triazin-2-yl Chemical group 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000035772 mutation Effects 0.000 description 26
- 230000000694 effects Effects 0.000 description 5
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 4
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- ODBLHEXUDAPZAU-UHFFFAOYSA-N isocitric acid Chemical compound OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
- HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 1
- 208000003950 B-cell lymphoma Diseases 0.000 description 1
- 206010042971 T-cell lymphoma Diseases 0.000 description 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000005895 oxidative decarboxylation reaction Methods 0.000 description 1
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361861884P | 2013-08-02 | 2013-08-02 | |
| US61/861,884 | 2013-08-02 | ||
| PCT/CN2013/081170 WO2015018060A1 (en) | 2013-08-09 | 2013-08-09 | Crystalline forms of therapeutically active compounds and use thereof |
| CNPCT/CN2013/081170 | 2013-08-09 | ||
| US201461939098P | 2014-02-12 | 2014-02-12 | |
| US61/939,098 | 2014-02-12 | ||
| US201461975448P | 2014-04-04 | 2014-04-04 | |
| US61/975,448 | 2014-04-04 | ||
| US201462011948P | 2014-06-13 | 2014-06-13 | |
| US62/011,948 | 2014-06-13 | ||
| PCT/US2014/049469 WO2015017821A2 (en) | 2013-08-02 | 2014-08-01 | Therapeutically active compounds and their methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019082794A Division JP2019142930A (ja) | 2013-08-02 | 2019-04-24 | 治療活性のある化合物及びその使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016527279A JP2016527279A (ja) | 2016-09-08 |
| JP2016527279A5 true JP2016527279A5 (https=) | 2017-09-07 |
| JP6742905B2 JP6742905B2 (ja) | 2020-08-19 |
Family
ID=52432592
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016531940A Active JP6742905B2 (ja) | 2013-08-02 | 2014-08-01 | 治療活性のある化合物及びその使用方法 |
| JP2019082794A Withdrawn JP2019142930A (ja) | 2013-08-02 | 2019-04-24 | 治療活性のある化合物及びその使用方法 |
| JP2021123814A Pending JP2021176893A (ja) | 2013-08-02 | 2021-07-29 | 治療活性のある化合物及びその使用方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019082794A Withdrawn JP2019142930A (ja) | 2013-08-02 | 2019-04-24 | 治療活性のある化合物及びその使用方法 |
| JP2021123814A Pending JP2021176893A (ja) | 2013-08-02 | 2021-07-29 | 治療活性のある化合物及びその使用方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (6) | US9738625B2 (https=) |
| EP (3) | EP3027193A4 (https=) |
| JP (3) | JP6742905B2 (https=) |
| CN (3) | CN110386922A (https=) |
| AU (2) | AU2014295938B2 (https=) |
| BR (1) | BR112016002287A2 (https=) |
| CA (1) | CA2919382A1 (https=) |
| CL (2) | CL2016000263A1 (https=) |
| EA (1) | EA030428B1 (https=) |
| ES (1) | ES2886211T3 (https=) |
| IL (2) | IL243833A0 (https=) |
| MX (2) | MX389250B (https=) |
| MY (1) | MY177994A (https=) |
| NI (1) | NI201600022A (https=) |
| PE (1) | PE20160840A1 (https=) |
| PH (1) | PH12016500164B1 (https=) |
| SA (1) | SA516370523B1 (https=) |
| SG (2) | SG10201709187TA (https=) |
| TW (2) | TWI666208B (https=) |
| UA (1) | UA121021C2 (https=) |
| WO (1) | WO2015017821A2 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015003360A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| TWI666208B (zh) * | 2013-08-02 | 2019-07-21 | 美商阿吉斯藥品有限公司 | 治療活性化合物及其使用方法（三） |
| AU2015324158A1 (en) | 2014-09-29 | 2017-04-13 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| CN107531675A (zh) | 2015-02-04 | 2018-01-02 | 安吉奥斯医药品有限公司 | 治疗活性化合物及其使用方法 |
| WO2016177347A1 (en) * | 2015-05-07 | 2016-11-10 | Teligene Ltd | Heterocyclic compounds as idh2 inhibitors |
| TWI722004B (zh) | 2015-07-30 | 2021-03-21 | 大陸商正大天晴藥業集團股份有限公司 | 1,3,5-三嗪衍生物及其使用方法 |
| CA2993615A1 (en) | 2015-08-05 | 2017-02-09 | Agios Pharmaceuticals, Inc. | Methods of preparing 6-(aryl or heteroaryl)-1,3,5-triazine-2,4-diols and 6-(aryl or heteroaryl)-1,3,5-triazine-2,4-diamines |
| CN108366980A (zh) | 2015-10-15 | 2018-08-03 | 安吉奥斯医药品有限公司 | 用于治疗恶性肿瘤的组合疗法 |
| US10695352B2 (en) * | 2015-10-15 | 2020-06-30 | Celgene Corporation | Combination therapy for treating malignancies |
| US9688659B2 (en) * | 2015-10-21 | 2017-06-27 | NeuForm Pharmaceuticals, Inc. | Deuterated compounds for treating hematologic malignancies, and compositions and methods thereof |
| IL298663A (en) * | 2015-12-04 | 2023-01-01 | Agios Pharmaceuticals Inc | Methods for treating acute myeloid leukemia characterized by the presence of a mutant allele of idh2 and the absence of a mutant allele of nras |
| WO2017140758A1 (en) | 2016-02-19 | 2017-08-24 | Debiopharm International S.A. | Derivatives of 2-amino-4-(2-oxazolidinon-3-yl)-pyrimidine fused with a five-membered heteroaromatic ring in 5,6-position which are useful for the treatment of various cancers |
| ES2912909T3 (es) | 2016-02-26 | 2022-05-30 | Celgene Corp | Enasidenib para su uso en el tratamiento de la leucemia mieloide aguda recidivante o refractaria |
| EP3493809B1 (en) | 2016-08-03 | 2023-08-23 | Celgene Corporation | Enasidenib for treatment of myelodysplastic syndrome |
| JP7093764B2 (ja) * | 2016-08-03 | 2022-06-30 | セルジーン コーポレイション | 骨髄異形成症候群の治療方法 |
| MX392941B (es) | 2016-09-07 | 2025-03-24 | Celgene Corp | Composiciones para comprimidos. |
| WO2018133856A1 (zh) * | 2017-01-22 | 2018-07-26 | 正大天晴药业集团股份有限公司 | 1，3，5-三嗪衍生物的盐及其晶体、它们的制备方法、药物组合物和用途 |
| WO2018204787A1 (en) | 2017-05-05 | 2018-11-08 | Memorial Sloan Kettering Cancer Center | Methods of treatment of myeloproliferative neoplasm |
| EP4201399A3 (en) | 2017-06-30 | 2023-08-09 | Celgene Corporation | Compositions and methods of use of 2-(4-chlorophenyl)-n-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl) methyl) -2,2-difluoroacetamide |
| CN109467538A (zh) | 2017-09-07 | 2019-03-15 | 和记黄埔医药（上海）有限公司 | 环烯烃取代的杂芳环类化合物及其用途 |
| WO2020092894A1 (en) | 2018-11-02 | 2020-05-07 | Celgene Corporation | Solid forms of 2-methyl-1-[(4-[6-(trifluoromethyl) pyridin-2-yl]-6-{[2-(trifluoromethyl)pyridin-4-yl]amino}-1,3,5-triazin-2-yl) amino]propan-2-ol |
| WO2020092906A1 (en) | 2018-11-02 | 2020-05-07 | Celgene Corporation | Co-crystals of 2-methyl-1 -[(4-[6-(trifluoromethyl)pyridin-2-yl]-6-{[2-(trifluoromethyl) pyridin-4-yl]amino}-1,3,5-triazin-2-yl)amino]propan-2-ol, compositions and methods of use thereof |
| WO2020092915A1 (en) | 2018-11-02 | 2020-05-07 | Celgene Corporation | Solid dispersions for treatment of cancer |
| WO2021097160A1 (en) | 2019-11-14 | 2021-05-20 | Celgene Corporation | Pediatric formulations for treatment of cancer |
| CN114773320A (zh) * | 2022-05-29 | 2022-07-22 | 重庆医科大学 | 1,3,5-三嗪化合物及其制备方法和用途 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2390529A (en) | 1942-02-03 | 1945-12-11 | Ernst A H Friedheim | Hydrazino-1,3,5-triazino derivatives of substituted phenylarsenic compounds |
| JPS58186682A (ja) | 1982-04-27 | 1983-10-31 | 日本化薬株式会社 | セルロ−ス又はセルロ−ス含有繊維材料の染色法 |
| DE3512630A1 (de) | 1985-04-06 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zum faerben oder bedrucken von cellulosefasern oder cellulosemischfasern |
| EP0466647B1 (de) | 1990-07-12 | 1995-11-29 | Ciba-Geigy Ag | Verfahren zur photochemischen und thermischen Stabilisierung von Polyamid-Fasermaterialien |
| JPH11158073A (ja) | 1997-09-26 | 1999-06-15 | Takeda Chem Ind Ltd | アデノシンａ３拮抗剤 |
| WO2000075129A1 (en) | 1999-06-07 | 2000-12-14 | Shire Biochem Inc. | Thiophene integrin inhibitors |
| US7291616B2 (en) * | 2001-10-31 | 2007-11-06 | Cell Therapeutics, Inc. | Aryl triazines as LPAAT-β inhibitors and uses thereof |
| EP1546121B1 (en) | 2002-07-18 | 2012-08-29 | Janssen Pharmaceutica NV | Substituted triazine kinase inhibitors |
| JP5450381B2 (ja) * | 2007-04-30 | 2014-03-26 | プロメティック・バイオサイエンスィズ・インコーポレーテッド | 化合物、そのような化合物を含有する組成物、及びそのような化合物を用いるがん及び自己免疫疾患の治療法 |
| GB0805477D0 (en) | 2008-03-26 | 2008-04-30 | Univ Nottingham | Pyrimidines triazines and their use as pharmaceutical agents |
| KR101460095B1 (ko) * | 2009-06-08 | 2014-11-10 | 캘리포니아 캐피탈 에쿼티, 엘엘씨 | 트리아진 유도체와 이들의 치료적 용도 |
| US8486939B2 (en) * | 2009-07-07 | 2013-07-16 | Pathway Therapeutics Inc. | Pyrimidinyl and 1,3,5-triazinyl benzimidazoles and their use in cancer therapy |
| NZ627096A (en) * | 2012-01-06 | 2017-02-24 | Agios Pharmaceuticals Inc | Triazinyl compounds and their methods of use |
| WO2013133367A1 (ja) | 2012-03-09 | 2013-09-12 | カルナバイオサイエンス株式会社 | 新規トリアジン誘導体 |
| MY185687A (en) | 2013-07-11 | 2021-05-30 | Agios Pharmaceuticals Inc | N,6-bis(aryl or heteroaryl)-1,3,5-triazine-2,4-diamine compounds as idh2 mutants inhibitors for the treatment of cancer |
| US9579324B2 (en) | 2013-07-11 | 2017-02-28 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| TWI666208B (zh) | 2013-08-02 | 2019-07-21 | 美商阿吉斯藥品有限公司 | 治療活性化合物及其使用方法（三） |
| AU2015324158A1 (en) * | 2014-09-29 | 2017-04-13 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| CN107531675A (zh) | 2015-02-04 | 2018-01-02 | 安吉奥斯医药品有限公司 | 治疗活性化合物及其使用方法 |
-
2014
- 2014-08-01 TW TW103126335A patent/TWI666208B/zh active
- 2014-08-01 MX MX2016001361A patent/MX389250B/es unknown
- 2014-08-01 AU AU2014295938A patent/AU2014295938B2/en active Active
- 2014-08-01 UA UAA201601999A patent/UA121021C2/uk unknown
- 2014-08-01 EP EP14832505.3A patent/EP3027193A4/en not_active Withdrawn
- 2014-08-01 SG SG10201709187TA patent/SG10201709187TA/en unknown
- 2014-08-01 EP EP19177845.5A patent/EP3566706B1/en active Active
- 2014-08-01 MX MX2020011397A patent/MX394658B/es unknown
- 2014-08-01 TW TW108110624A patent/TWI701242B/zh active
- 2014-08-01 ES ES19177845T patent/ES2886211T3/es active Active
- 2014-08-01 WO PCT/US2014/049469 patent/WO2015017821A2/en not_active Ceased
- 2014-08-01 EP EP21178745.2A patent/EP3932408A1/en not_active Withdrawn
- 2014-08-01 US US14/909,451 patent/US9738625B2/en active Active
- 2014-08-01 SG SG11201600479WA patent/SG11201600479WA/en unknown
- 2014-08-01 EA EA201690322A patent/EA030428B1/ru not_active IP Right Cessation
- 2014-08-01 MY MYPI2016700311A patent/MY177994A/en unknown
- 2014-08-01 BR BR112016002287A patent/BR112016002287A2/pt not_active Application Discontinuation
- 2014-08-01 PH PH1/2016/500164A patent/PH12016500164B1/en unknown
- 2014-08-01 CN CN201910708167.6A patent/CN110386922A/zh active Pending
- 2014-08-01 CN CN201480053796.5A patent/CN105916507A/zh active Pending
- 2014-08-01 JP JP2016531940A patent/JP6742905B2/ja active Active
- 2014-08-01 PE PE2016000214A patent/PE20160840A1/es not_active Application Discontinuation
- 2014-08-01 CN CN201910707312.9A patent/CN110372670B/zh active Active
- 2014-08-01 CA CA2919382A patent/CA2919382A1/en not_active Abandoned
-
2016
- 2016-01-28 IL IL243833A patent/IL243833A0/en unknown
- 2016-02-01 SA SA516370523A patent/SA516370523B1/ar unknown
- 2016-02-01 NI NI201600022A patent/NI201600022A/es unknown
- 2016-02-02 CL CL2016000263A patent/CL2016000263A1/es unknown
-
2017
- 2017-07-13 US US15/649,551 patent/US10093654B2/en active Active
- 2017-09-04 CL CL2017002240A patent/CL2017002240A1/es unknown
-
2018
- 2018-09-04 US US16/121,483 patent/US10730854B2/en active Active
- 2018-10-10 AU AU2018247242A patent/AU2018247242B2/en active Active
-
2019
- 2019-04-24 JP JP2019082794A patent/JP2019142930A/ja not_active Withdrawn
- 2019-10-31 IL IL270347A patent/IL270347B/en unknown
-
2020
- 2020-06-29 US US16/915,936 patent/US20210155603A1/en not_active Abandoned
-
2021
- 2021-07-29 JP JP2021123814A patent/JP2021176893A/ja active Pending
-
2023
- 2023-05-08 US US18/144,695 patent/US20240132474A1/en not_active Abandoned
-
2025
- 2025-05-07 US US19/201,790 patent/US20260085059A1/en active Pending
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