CA2917424A1 - Therapeutically active compounds and their methods of use - Google Patents
Therapeutically active compounds and their methods of use Download PDFInfo
- Publication number
- CA2917424A1 CA2917424A1 CA2917424A CA2917424A CA2917424A1 CA 2917424 A1 CA2917424 A1 CA 2917424A1 CA 2917424 A CA2917424 A CA 2917424A CA 2917424 A CA2917424 A CA 2917424A CA 2917424 A1 CA2917424 A1 CA 2917424A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkylene
- optionally substituted
- compound
- cyclopropyl
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 141
- 238000000034 method Methods 0.000 title claims abstract description 49
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- 201000011510 cancer Diseases 0.000 claims abstract description 39
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- 125000002947 alkylene group Chemical group 0.000 claims description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 230000035772 mutation Effects 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 29
- 102100037845 Isocitrate dehydrogenase [NADP], mitochondrial Human genes 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 101000599886 Homo sapiens Isocitrate dehydrogenase [NADP], mitochondrial Proteins 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 229940124597 therapeutic agent Drugs 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
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- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims description 3
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- POMIVUIRXMKGPO-UHFFFAOYSA-N 2-n-tert-butyl-4-n-[4-[chloro(difluoro)methoxy]phenyl]-6-piperidin-1-yl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCCCC2)=NC(NC(C)(C)C)=NC=1NC1=CC=C(OC(F)(F)Cl)C=C1 POMIVUIRXMKGPO-UHFFFAOYSA-N 0.000 claims 1
- QYMBGKUQTBGEMR-UHFFFAOYSA-N 2-n-tert-butyl-6-morpholin-4-yl-4-n-[4-(trifluoromethoxy)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCOCC2)=NC(NC(C)(C)C)=NC=1NC1=CC=C(OC(F)(F)F)C=C1 QYMBGKUQTBGEMR-UHFFFAOYSA-N 0.000 claims 1
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- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
- 229960000237 vorinostat Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- RPQZTTQVRYEKCR-WCTZXXKLSA-N zebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=CC=C1 RPQZTTQVRYEKCR-WCTZXXKLSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2013/079184 WO2015003355A2 (en) | 2013-07-11 | 2013-07-11 | Therapeutically active compounds and their methods of use |
| CNPCT/CN2013/079184 | 2013-07-11 | ||
| PCT/CN2014/081958 WO2015003641A1 (en) | 2013-07-11 | 2014-07-10 | Therapeutically active compounds and their methods of use |
Publications (1)
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|---|---|
| CA2917424A1 true CA2917424A1 (en) | 2015-01-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2917424A Abandoned CA2917424A1 (en) | 2013-07-11 | 2014-07-10 | Therapeutically active compounds and their methods of use |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10017495B2 (enExample) |
| EP (1) | EP3019484B1 (enExample) |
| JP (1) | JP6490067B2 (enExample) |
| AU (1) | AU2014289745B2 (enExample) |
| CA (1) | CA2917424A1 (enExample) |
| HK (1) | HK1223924A1 (enExample) |
| WO (2) | WO2015003355A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6529492B2 (ja) | 2013-07-11 | 2019-06-12 | アジオス ファーマシューティカルズ， インコーポレイテッド | 癌の処置のためのｉｄｈ２突然変異体阻害剤としての２，４−または４，６−ジアミノピリミジン化合物 |
| WO2015003360A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| US9579324B2 (en) | 2013-07-11 | 2017-02-28 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| CN105555779B (zh) * | 2013-07-16 | 2019-05-10 | 巴斯夫欧洲公司 | 除草的嗪类 |
| AU2015229214B2 (en) | 2014-03-14 | 2019-07-11 | Les Laboratoires Servier | Pharmaceutical compositions of therapeutically active compounds |
| US10941122B2 (en) | 2014-04-11 | 2021-03-09 | Basf Se | Diaminotriazine derivatives as herbicides |
| WO2015162166A1 (en) | 2014-04-23 | 2015-10-29 | Basf Se | Diaminotriazine compounds and their use as herbicides |
| MA43848A (fr) * | 2015-10-21 | 2018-11-21 | Neuform Pharmaceuticals Inc | Composés deutérés pour le traitement d'hémopathies malignes, compositions et procédés associés |
| 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 |
| EP3535025B1 (en) | 2016-11-02 | 2023-06-28 | University of Cincinnati | Composition comprising r-2-hydroxyglutarate and one agent that inhibits myc signaling for treating cancer |
| SG11201913008TA (en) | 2017-06-30 | 2020-01-30 | Celgene Corp | Compositions and methods of use of 2-(4-chlorophenyl)-n-((2-(2,6-doxopiperidin-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 |
| WO2019109095A1 (en) * | 2017-12-01 | 2019-06-06 | Beth Israel Deaconess Medical Center, Inc. | Arsenic trioxide and retinoic acid compounds for treatment of idh2-associated disorders |
| CA3150818A1 (en) | 2019-08-13 | 2021-02-18 | King's College London | Immunoresponsive cells armoured with spatiotemporally restricted activity of cytokines of the il-1 superfamily |
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-
2013
- 2013-07-11 WO PCT/CN2013/079184 patent/WO2015003355A2/en not_active Ceased
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2014
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- 2014-07-10 AU AU2014289745A patent/AU2014289745B2/en not_active Ceased
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- 2014-07-10 WO PCT/CN2014/081958 patent/WO2015003641A1/en not_active Ceased
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| US20160159771A1 (en) | 2016-06-09 |
| HK1223924A1 (zh) | 2017-08-11 |
| EP3019484A4 (en) | 2016-11-23 |
| JP6490067B2 (ja) | 2019-03-27 |
| EP3019484B1 (en) | 2021-09-08 |
| WO2015003355A2 (en) | 2015-01-15 |
| WO2015003355A3 (en) | 2015-03-12 |
| JP2016523935A (ja) | 2016-08-12 |
| US10017495B2 (en) | 2018-07-10 |
| WO2015003641A1 (en) | 2015-01-15 |
| AU2014289745A1 (en) | 2016-01-28 |
| EP3019484A1 (en) | 2016-05-18 |
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