CA2969090C - Triazolopyrimidine compounds and uses thereof - Google Patents
Triazolopyrimidine compounds and uses thereof Download PDFInfo
- Publication number
- CA2969090C CA2969090C CA2969090A CA2969090A CA2969090C CA 2969090 C CA2969090 C CA 2969090C CA 2969090 A CA2969090 A CA 2969090A CA 2969090 A CA2969090 A CA 2969090A CA 2969090 C CA2969090 C CA 2969090C
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- CA
- Canada
- Prior art keywords
- pyrimidin
- methyl
- dihydrobenzofuran
- triazolo
- amine
- 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.)
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- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 400
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 90
- 150000003839 salts Chemical class 0.000 claims abstract description 86
- 201000010099 disease Diseases 0.000 claims abstract description 48
- 208000035475 disorder Diseases 0.000 claims abstract description 41
- 230000001404 mediated effect Effects 0.000 claims abstract description 22
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims description 154
- -1 (5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl Chemical group 0.000 claims description 128
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 57
- 239000003814 drug Substances 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 52
- 108010000597 Polycomb Repressive Complex 2 Proteins 0.000 claims description 51
- 102000002272 Polycomb Repressive Complex 2 Human genes 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- 101000866766 Homo sapiens Polycomb protein EED Proteins 0.000 claims description 42
- HVOVXNWEZWMGLZ-UHFFFAOYSA-N [1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound NC1=NC=CC=2N1C=NN2 HVOVXNWEZWMGLZ-UHFFFAOYSA-N 0.000 claims description 42
- 102100031338 Polycomb protein EED Human genes 0.000 claims description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 41
- 229940124597 therapeutic agent Drugs 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000004565 2,3-dihydrobenzofuran-4-yl group Chemical group O1CCC2=C1C=CC=C2* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 238000002560 therapeutic procedure Methods 0.000 claims description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 201000003444 follicular lymphoma Diseases 0.000 claims description 9
- 206010025323 Lymphomas Diseases 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 8
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 8
- 239000002955 immunomodulating agent Substances 0.000 claims description 8
- 229940121354 immunomodulator Drugs 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 208000034578 Multiple myelomas Diseases 0.000 claims description 7
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
- 208000008938 Rhabdoid tumor Diseases 0.000 claims description 7
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 7
- 206010017758 gastric cancer Diseases 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 208000032839 leukemia Diseases 0.000 claims description 7
- 201000011549 stomach cancer Diseases 0.000 claims description 7
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 206010060862 Prostate cancer Diseases 0.000 claims description 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
- 230000003474 anti-emetic effect Effects 0.000 claims description 6
- 239000000043 antiallergic agent Substances 0.000 claims description 6
- 239000002111 antiemetic agent Substances 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 230000001120 cytoprotective effect Effects 0.000 claims description 6
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 206010003571 Astrocytoma Diseases 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
- 206010005003 Bladder cancer Diseases 0.000 claims description 5
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 5
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 206010014733 Endometrial cancer Diseases 0.000 claims description 5
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 5
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 5
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims description 5
- 208000032612 Glial tumor Diseases 0.000 claims description 5
- 206010018338 Glioma Diseases 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
- 206010027406 Mesothelioma Diseases 0.000 claims description 5
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 5
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 206010033963 Parathyroid tumour Diseases 0.000 claims description 5
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 5
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 5
- 206010039491 Sarcoma Diseases 0.000 claims description 5
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 5
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
- 210000000013 bile duct Anatomy 0.000 claims description 5
- 208000026900 bile duct neoplasm Diseases 0.000 claims description 5
- 201000001531 bladder carcinoma Diseases 0.000 claims description 5
- 201000008275 breast carcinoma Diseases 0.000 claims description 5
- 201000010881 cervical cancer Diseases 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 5
- 201000004101 esophageal cancer Diseases 0.000 claims description 5
- 208000005017 glioblastoma Diseases 0.000 claims description 5
- 201000010536 head and neck cancer Diseases 0.000 claims description 5
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 5
- 201000005202 lung cancer Diseases 0.000 claims description 5
- 208000020816 lung neoplasm Diseases 0.000 claims description 5
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
- 201000001441 melanoma Diseases 0.000 claims description 5
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
- 206010038038 rectal cancer Diseases 0.000 claims description 5
- 201000001275 rectum cancer Diseases 0.000 claims description 5
- 208000017997 tumor of parathyroid gland Diseases 0.000 claims description 5
- 208000025421 tumor of uterus Diseases 0.000 claims description 5
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims description 5
- 206010046766 uterine cancer Diseases 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims description 4
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 4
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 4
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 4
- 230000002584 immunomodulator Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229940124641 pain reliever Drugs 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 3
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 3
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 3
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 claims description 3
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 3
- 206010029260 Neuroblastoma Diseases 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 201000011216 nasopharynx carcinoma Diseases 0.000 claims description 3
- 208000007538 neurilemmoma Diseases 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 206010039667 schwannoma Diseases 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 2
- VCMDFQHVNRLVEX-UHFFFAOYSA-N N-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methyl]-8-(1-oxidopyridin-1-ium-3-yl)-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound FC=1C=CC2=C(CCO2)C=1CNC1=NC=C(C=2N1C=NN=2)C=1C=[N+](C=CC=1)[O-] VCMDFQHVNRLVEX-UHFFFAOYSA-N 0.000 claims description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 230000008913 ectoderm development Effects 0.000 claims 2
- MEXQSCNJSSKRTA-UHFFFAOYSA-N 1-[5-[5-(2,3-dihydro-1-benzofuran-4-ylmethylamino)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]pyridin-2-yl]azetidin-3-ol Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=CC(=NC=1)N1CC(C1)O MEXQSCNJSSKRTA-UHFFFAOYSA-N 0.000 claims 1
- DCANOELGDVKTTQ-UHFFFAOYSA-N 1-[5-[5-(2,3-dihydro-1-benzofuran-4-ylmethylamino)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]pyridin-2-yl]piperazin-2-one Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=CC(=NC=1)N1C(CNCC1)=O DCANOELGDVKTTQ-UHFFFAOYSA-N 0.000 claims 1
- QHQAGMSQHMYPIY-UHFFFAOYSA-N 1-[5-[5-(2,3-dihydro-1-benzofuran-4-ylmethylamino)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]pyridin-3-yl]pyrrolidin-2-one Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=C(C=NC=1)N1C(CCC1)=O QHQAGMSQHMYPIY-UHFFFAOYSA-N 0.000 claims 1
- ABUKMYSLIKFEPI-UHFFFAOYSA-N 2-[5-[5-(2,3-dihydro-1-benzofuran-4-ylmethylamino)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]pyridin-2-yl]propan-2-ol Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=CC(=NC=1)C(C)(C)O ABUKMYSLIKFEPI-UHFFFAOYSA-N 0.000 claims 1
- QVNFRQNZBTZXRZ-UHFFFAOYSA-N 4-[5-[5-(2,3-dihydro-1-benzofuran-4-ylmethylamino)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]pyridin-2-yl]piperazine-1-carbaldehyde Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=CC(=NC=1)N1CCN(CC1)C=O QVNFRQNZBTZXRZ-UHFFFAOYSA-N 0.000 claims 1
- WWHYMGYUZYXMOK-UHFFFAOYSA-N 5-[5-(2,3-dihydro-1-benzofuran-4-ylmethylamino)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]-N,N-dimethylpyridine-2-carboxamide Chemical compound CN(C)C(=O)c1ccc(cn1)-c1cnc(NCc2cccc3OCCc23)n2cnnc12 WWHYMGYUZYXMOK-UHFFFAOYSA-N 0.000 claims 1
- BMNLIJATOXLROW-UHFFFAOYSA-N 5-[5-(2,3-dihydro-1-benzofuran-4-ylmethylamino)-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]-N-[2-(dimethylamino)ethyl]-N-methylpyridine-2-carboxamide Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=CC(=NC=1)C(=O)N(C)CCN(C)C BMNLIJATOXLROW-UHFFFAOYSA-N 0.000 claims 1
- WMZCIJCAOGMXJT-UHFFFAOYSA-N 5-[5-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methylamino]-[1,2,4]triazolo[4,3-c]pyrimidin-8-yl]pyridine-2-carbonitrile Chemical compound FC=1C=CC2=C(CCO2)C=1CNC1=NC=C(C=2N1C=NN=2)C=1C=CC(=NC=1)C#N WMZCIJCAOGMXJT-UHFFFAOYSA-N 0.000 claims 1
- PHHIHVIOVGUMSY-UHFFFAOYSA-N 5-fluoro-4-[[[8-(2-methylpyridin-3-yl)-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl]amino]methyl]-2,3-dihydro-1-benzofuran-3-ol Chemical compound FC=1C=CC2=C(C(CO2)O)C=1CNC1=NC=C(C=2N1C=NN=2)C=1C(=NC=CC=1)C PHHIHVIOVGUMSY-UHFFFAOYSA-N 0.000 claims 1
- BPVVBXTWDZKTIU-UHFFFAOYSA-N 8-(2,3-dimethylimidazol-4-yl)-N-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methyl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound Cc1ncc(-c2cnc(NCc3c4CCOc4ccc3F)n3cnnc23)n1C BPVVBXTWDZKTIU-UHFFFAOYSA-N 0.000 claims 1
- TXRLRLBNYXSZGD-UHFFFAOYSA-N 8-(2-cyclopropyl-4-methylpyrimidin-5-yl)-N-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methyl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound C1(CC1)C1=NC=C(C(=N1)C)C=1C=2N(C(=NC=1)NCC1=C(C=CC3=C1CCO3)F)C=NN=2 TXRLRLBNYXSZGD-UHFFFAOYSA-N 0.000 claims 1
- FYNWPJVYFPSZCO-UHFFFAOYSA-N 8-[6-[2-(3,3-difluoropyrrolidin-1-yl)ethyl]pyridin-3-yl]-N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound FC1(CN(CC1)CCC1=CC=C(C=N1)C=1C=2N(C(=NC=1)NCC1=CC=CC3=C1CCO3)C=NN=2)F FYNWPJVYFPSZCO-UHFFFAOYSA-N 0.000 claims 1
- IZOARSUTSNEABS-UHFFFAOYSA-N N-(1-benzofuran-4-ylmethyl)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound O1C=CC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C1=CC=CC=C1 IZOARSUTSNEABS-UHFFFAOYSA-N 0.000 claims 1
- GDDMEOORUYUIJL-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-(4-methylsulfonylphenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound CS(=O)(=O)c1ccc(cc1)-c1cnc(NCc2cccc3OCCc23)n2cnnc12 GDDMEOORUYUIJL-UHFFFAOYSA-N 0.000 claims 1
- JQTMERFVMVOYDH-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-[2-(dimethylamino)pyrimidin-5-yl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound CN(C)c1ncc(cn1)-c1cnc(NCc2cccc3OCCc23)n2cnnc12 JQTMERFVMVOYDH-UHFFFAOYSA-N 0.000 claims 1
- RKFGJEQBUNXCBP-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-[3-[2-(dimethylamino)ethyl]phenyl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound CN(C)CCc1cccc(c1)-c1cnc(NCc2cccc3OCCc23)n2cnnc12 RKFGJEQBUNXCBP-UHFFFAOYSA-N 0.000 claims 1
- VOOPZQBLDZVBAT-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-[5-(3-methylsulfonylpropoxy)pyridin-3-yl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=NC=C(C=1)OCCCS(=O)(=O)C VOOPZQBLDZVBAT-UHFFFAOYSA-N 0.000 claims 1
- GSPMBCOSONHTOL-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-[5-(4,4-dimethyl-5H-1,3-oxazol-2-yl)pyridin-3-yl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=NC=C(C=1)C=1OCC(N=1)(C)C GSPMBCOSONHTOL-UHFFFAOYSA-N 0.000 claims 1
- GVZXYFCBILGQCQ-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-[6-(2-methoxyethyl)pyridin-3-yl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound COCCc1ccc(cn1)-c1cnc(NCc2cccc3OCCc23)n2cnnc12 GVZXYFCBILGQCQ-UHFFFAOYSA-N 0.000 claims 1
- HORZWCBJHIPTFF-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-[6-(2-methylpyrrolidin-1-yl)pyridin-3-yl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=NC(=CC=1)N1C(CCC1)C HORZWCBJHIPTFF-UHFFFAOYSA-N 0.000 claims 1
- LCEAJAZTHFIGTQ-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-[6-(4,4-dimethyl-5H-1,3-oxazol-2-yl)pyridin-3-yl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C=1C=NC(=CC=1)C=1OCC(N=1)(C)C LCEAJAZTHFIGTQ-UHFFFAOYSA-N 0.000 claims 1
- OIAQKXJXJLUAPX-UHFFFAOYSA-N N-(2,3-dihydro-1-benzofuran-4-ylmethyl)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine Chemical compound O1CCC2=C1C=CC=C2CNC1=NC=C(C=2N1C=NN=2)C1=CC=CC=C1 OIAQKXJXJLUAPX-UHFFFAOYSA-N 0.000 claims 1
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- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
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- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A—HUMAN NECESSITIES
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- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/541—Non-condensed thiazines containing further heterocyclic rings
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2014/094644 | 2014-12-23 | ||
| CN2014094644 | 2014-12-23 | ||
| CNPCT/CN2015/095320 | 2015-11-23 | ||
| CN2015095320 | 2015-11-23 | ||
| PCT/IB2015/059843 WO2016103155A1 (en) | 2014-12-23 | 2015-12-21 | Triazolopyrimidine compounds and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2969090A1 CA2969090A1 (en) | 2016-06-30 |
| CA2969090C true CA2969090C (en) | 2023-05-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2969090A Active CA2969090C (en) | 2014-12-23 | 2015-12-21 | Triazolopyrimidine compounds and uses thereof |
Country Status (40)
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| SG11201703880VA (en) * | 2014-12-23 | 2017-07-28 | Novartis Ag | Triazolopyrimidine compounds and uses thereof |
| AU2017273726B2 (en) | 2016-06-01 | 2023-10-19 | Epizyme, Inc. | Use of EZH2 inhibitors for treating cancer |
| ES2975263T3 (es) | 2016-06-20 | 2024-07-04 | Novartis Ag | Formas cristalinas de un compuesto triazolopirimidínico |
| CN109790166A (zh) | 2016-06-20 | 2019-05-21 | 诺华股份有限公司 | 咪唑并吡啶化合物用于治疗癌症 |
| ES2798424T3 (es) * | 2016-06-20 | 2020-12-11 | Novartis Ag | Compuestos de triazolopiridina y usos de estos |
| CN116478132A (zh) | 2016-07-12 | 2023-07-25 | 锐新医药公司 | 作为变构shp2抑制剂的2,5-双取代型及2,5,6-三取代型3-甲基吡嗪 |
| CN106831601A (zh) * | 2017-01-13 | 2017-06-13 | 河北博伦特药业有限公司 | 一种2‑氨基甲基嘧啶盐酸盐及其衍生物的合成方法 |
| AU2018210196B2 (en) | 2017-01-23 | 2022-06-02 | Revolution Medicines, Inc. | Pyridine compounds as allosteric SHP2 inhibitors |
| CN110446709B (zh) | 2017-01-23 | 2023-09-12 | 锐新医药公司 | 作为变构shp2抑制剂的二环化合物 |
| WO2018170290A1 (en) * | 2017-03-15 | 2018-09-20 | Fulcrum Therapeutics, Inc. | Compositions and methods for increasing fmr1 expression |
| US10266542B2 (en) | 2017-03-15 | 2019-04-23 | Mirati Therapeutics, Inc. | EZH2 inhibitors |
| EP3575301A4 (en) * | 2017-03-16 | 2020-08-05 | Jiangsu Hengrui Medicine Co., Ltd. | HETEROARYL [4,3-C] PYRIMIDINE-5-AMINE DERIVATIVE, PROCESS FOR PREPARATION AND MEDICAL USES |
| AU2018275123A1 (en) | 2017-06-02 | 2020-01-30 | Epizyme, Inc. | Use of EZH2 inhibitors for treating cancer |
| CN109575013A (zh) * | 2017-09-28 | 2019-04-05 | 中国科学院上海药物研究所 | 三氮唑并嘧啶、三氮唑并吡啶化合物及其组合物用于治疗prc2介导的疾病 |
| WO2019062435A1 (zh) * | 2017-09-28 | 2019-04-04 | 中国科学院上海药物研究所 | 三氮唑并嘧啶、三氮唑并吡啶化合物及其组合物用于治疗prc2介导的疾病 |
| CA3078565A1 (en) | 2017-10-12 | 2019-04-18 | Revolution Medicines, Inc. | Pyridine, pyrazine, and triazine compounds as allosteric shp2 inhibitors |
| CN109867645B (zh) * | 2017-12-05 | 2021-09-14 | 中国医学科学院药物研究所 | 一种2,2-二氟-2,3-二氢取代苯并呋喃类化合物的合成方法 |
| BR112020009757A2 (pt) | 2017-12-15 | 2020-11-03 | Revolution Medicines, Inc. | compostos policíclicos como inibidores alostéricos de shp2 |
| CN109942556A (zh) * | 2017-12-21 | 2019-06-28 | 上海青煜医药科技有限公司 | 嘧啶酮化合物及其应用 |
| US11591312B2 (en) | 2018-01-23 | 2023-02-28 | Basf Se | Halogenation of pyridine derivatives |
| WO2019152419A1 (en) | 2018-01-31 | 2019-08-08 | Mirati Therapeutics, Inc | Prc2 inhibitors |
| CN110156787B (zh) * | 2018-02-13 | 2021-11-02 | 中国科学院上海药物研究所 | 一种三氮唑并嘧啶衍生化合物、包含其的药物组合物及其用途 |
| CN110563722A (zh) * | 2018-06-06 | 2019-12-13 | 上海青煜医药科技有限公司 | 吡啶或哒嗪并环化合物及其应用 |
| CN110734436A (zh) * | 2018-07-19 | 2020-01-31 | 上海青煜医药科技有限公司 | 嘧啶或吡嗪并环化合物及其应用 |
| BR112021009880A2 (pt) * | 2018-11-30 | 2021-08-17 | Tuojie Biotech (Shanghai) Co., Ltd. | pirimidina e derivado de heterociclo de nitrogênio de cinco membros, método de preparação para os mesmos e usos médicos dos mesmos |
| CN111518100A (zh) * | 2019-02-02 | 2020-08-11 | 上海青煜医药科技有限公司 | 环丙烯并苯并呋喃取代的氮杂芳基化合物及其应用 |
| JP7549597B2 (ja) | 2019-03-15 | 2024-09-11 | フルクラム セラピューティクス，インコーポレイテッド | Ｅｅｄおよびｐｒｃ２調節物質としての大環状アゾロピリジン誘導体 |
| EP3950064A4 (en) * | 2019-04-03 | 2023-01-04 | Tera Stone Co., Ltd | THYMINE NUCLEOBASE BASED TRIAZOLOPYRIMIDINES AND PROCESS FOR THEIR PRODUCTION |
| EP3959214A1 (en) * | 2019-04-22 | 2022-03-02 | Mirati Therapeutics, Inc. | Naphthyridine derivatives as prc2 inhibitors |
| EP3969639B1 (en) | 2019-05-13 | 2025-03-12 | Ecolab Usa Inc. | 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor |
| US20220305021A1 (en) * | 2019-06-05 | 2022-09-29 | Athenex, Inc. | Methods of treating and/or preventing psoriasis |
| CA3142711A1 (en) * | 2019-06-05 | 2020-12-10 | Mirati Therapeutics, Inc. | Imidazo[1,2-c]pyrimidine derivatives as prc2 inhibitors for treating cancer |
| WO2021011713A1 (en) | 2019-07-16 | 2021-01-21 | The Regents Of The University Of Michigan | Imidazopyrimidines as eed inhibitors and the use thereof |
| US20230002414A1 (en) * | 2019-08-22 | 2023-01-05 | Blueray Therapeutics (Shanghai) Co., Ltd | Azaheteroaryl compound and application thereof |
| US20220280509A1 (en) | 2019-09-26 | 2022-09-08 | Novartis Ag | Aza-quinoline compounds and uses thereof |
| WO2021083380A1 (zh) * | 2019-11-01 | 2021-05-06 | 上海科技大学 | Eed抑制剂及其制备方法和用途 |
| CN113004233B (zh) * | 2019-12-18 | 2022-12-20 | 南京优氟医药科技有限公司 | 一种用于制备prc2抑制剂的化合物、其制备方法和用途 |
| CN111333655B (zh) * | 2020-04-13 | 2021-07-13 | 武汉工程大学 | 一种三唑并嘧啶类化合物及其制备方法和应用 |
| CN113636993B (zh) * | 2020-05-11 | 2022-08-19 | 苏州亚盛药业有限公司 | (5-氟-2,3-二氢苯并呋喃-4-基)甲胺或其盐的制备方法及其中间体 |
| WO2021240373A1 (en) | 2020-05-28 | 2021-12-02 | Novartis Ag | Dosing regimens for n-((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)-8-(2-methylpyridin-3-yl)-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine, or a pharmaceutically acceptable salt thereof, for use in treating prc2-mediated diseases or disorders |
| CN114907385A (zh) | 2021-02-10 | 2022-08-16 | 上海青煜医药科技有限公司 | 氮杂芳基化合物、其制备方法及应用 |
| WO2023016511A1 (zh) * | 2021-08-11 | 2023-02-16 | 上海青煜医药科技有限公司 | 氮杂芳基化合物、其制备方法及应用 |
| CN117384153A (zh) * | 2022-07-12 | 2024-01-12 | 上海赛岚生物科技有限公司 | 一类甲基转移酶抑制剂及其用途 |
| WO2024215699A1 (en) * | 2023-04-11 | 2024-10-17 | Oric Pharmaceuticals, Inc. | Treatment of t-cell lymphoma |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2779780A (en) | 1955-03-01 | 1957-01-29 | Du Pont | 1, 4-diamino-2, 3-dicyano-1, 4-bis (substituted mercapto) butadienes and their preparation |
| EP0647450A1 (en) | 1993-09-09 | 1995-04-12 | BEHRINGWERKE Aktiengesellschaft | Improved prodrugs for enzyme mediated activation |
| JP2002532415A (ja) | 1998-12-16 | 2002-10-02 | ワーナー−ランバート・カンパニー | Ｍｅｋ阻害剤による関節炎の治療 |
| NL1014106C2 (nl) | 2000-01-18 | 2001-07-20 | Univ Amsterdam | Werkwijze voor het detecteren van een pathologische afwijking bij een cel, een antistof en een assay kit. |
| OA12333A (en) | 2000-07-19 | 2004-04-06 | Warner Lambert Co | Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids. |
| SE519662C2 (sv) | 2001-07-04 | 2003-03-25 | Asept Int Ab | Ventilanordning vid utportioneringsanordningar |
| AU2002357667A1 (en) * | 2001-10-24 | 2003-05-06 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| US6921762B2 (en) | 2001-11-16 | 2005-07-26 | Amgen Inc. | Substituted indolizine-like compounds and methods of use |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| KR101210018B1 (ko) | 2002-03-08 | 2012-12-07 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 약물로서 유용한 거대고리 화합물 |
| PT1482932E (pt) | 2002-03-13 | 2010-01-12 | Array Biopharma Inc | Derivados de benzimidazole alquilado n3 como inibidores de mek |
| GB0228900D0 (en) | 2002-12-11 | 2003-01-15 | Ml Lab Plc | Cancer Immunotherapy |
| JP2004238296A (ja) | 2003-02-04 | 2004-08-26 | Kissei Pharmaceut Co Ltd | 新規なトリアゾロピリミジン誘導体、それを含有する医薬組成物およびそれらの用途 |
| WO2005005601A2 (en) | 2003-06-09 | 2005-01-20 | The Regents Of The University Of Michigan | Compositions and methods for treating and diagnosing cancer |
| US20060246505A1 (en) | 2003-09-02 | 2006-11-02 | Reinhard Walther | Modulation of the synthesis of insulin |
| US7563589B2 (en) | 2004-06-01 | 2009-07-21 | The University Of North Carolina At Chapel Hill | Reconstituted histone methyltransferase complex and methods of identifying modulators thereof |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| US7452892B2 (en) | 2005-06-17 | 2008-11-18 | Bristol-Myers Squibb Company | Triazolopyrimidine cannabinoid receptor 1 antagonists |
| PL1912636T3 (pl) | 2005-07-21 | 2015-02-27 | Ardea Biosciences Inc | N-(aryloamino)sulfonamidowe inhibitory mek |
| JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| US7890267B2 (en) | 2006-03-31 | 2011-02-15 | Ordway Research Institute | Prognostic and diagnostic method for cancer therapy |
| CA2673784A1 (en) | 2006-12-27 | 2008-07-10 | Usc Stevens-University Of Southern California | Dna methylation markers based on epigenetic stem cell signatures in cancer |
| WO2009017670A2 (en) | 2007-07-26 | 2009-02-05 | University Of Massachusetts | Ras-mediated epigenetic silencing effectors and uses thereof |
| EP2183255A4 (en) | 2007-08-29 | 2011-06-15 | Methylgene Inc | METHOD AND INTERMEDIATE PRODUCTS FOR THE PREPARATION OF CONDENSED HETEROCYCLIC KINASE INHIBITORS |
| US8247397B2 (en) | 2007-09-12 | 2012-08-21 | Genentech, Inc. | Combinations of phosphoinositide 3-kinase inhibitor compounds and chemotherapeutic agents, and methods of use |
| CN101909631B (zh) | 2007-10-25 | 2012-09-12 | 健泰科生物技术公司 | 制备噻吩并嘧啶化合物的方法 |
| US8168784B2 (en) | 2008-06-20 | 2012-05-01 | Abbott Laboratories | Processes to make apoptosis promoters |
| GB0822248D0 (en) | 2008-12-05 | 2009-01-14 | Medical Res Council | Crystal meths |
| WO2010111712A2 (en) | 2009-03-27 | 2010-09-30 | Cold Spring Harbor Laboratory | Identification of rnai targets and use of rnai for rational therapy of chemotherapy-resistant leukemia and other cancers |
| CN102020643A (zh) | 2009-09-22 | 2011-04-20 | 上海恒瑞医药有限公司 | 二氢喋啶酮类衍生物、其制备方法及其在医药上的应用 |
| TW201200518A (en) | 2010-03-10 | 2012-01-01 | Kalypsys Inc | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| MX2012012966A (es) * | 2010-05-07 | 2013-01-22 | Glaxosmithkline Llc | Indoles. |
| AU2011298987B2 (en) | 2010-09-10 | 2017-09-28 | Epizyme, Inc. | Inhibitors of human EZH2, and methods of use thereof |
| WO2012151277A1 (en) | 2011-05-02 | 2012-11-08 | Applied Informatic Solutions, Inc. | Kits and methods for selecting a treatment for ovarian cancer |
| US20140213475A1 (en) | 2011-07-14 | 2014-07-31 | University Of Massachusetts | Methods of diagnosing cancer using epigenetic biomarkers |
| JP2014534178A (ja) | 2011-09-30 | 2014-12-18 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | 癌の処置方法 |
| AU2013232229B2 (en) | 2012-03-12 | 2017-11-23 | Epizyme, Inc. | Inhibitors of human EZH2, and methods of use thereof |
| JP2016500073A (ja) | 2012-11-19 | 2016-01-07 | ノバルティス アーゲー | 寄生虫病の処置のための化合物および組成物 |
| WO2014100080A1 (en) | 2012-12-19 | 2014-06-26 | Glaxosmithkline Llc | Combination |
| CA2900764A1 (en) | 2013-02-08 | 2014-08-14 | Stemcentrx, Inc. | Novel multispecific constructs |
| MA38341B1 (fr) | 2013-02-11 | 2018-11-30 | Constellation Pharmaceuticals Inc | Modulateurs d'enzymes de modification par méthylation, compositions et utilisations associées |
| KR20150127216A (ko) | 2013-03-14 | 2015-11-16 | 제넨테크, 인크. | 암의 치료 및 암 약물 내성의 예방 방법 |
| US9776996B2 (en) * | 2013-03-15 | 2017-10-03 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
| EP2970305B1 (en) | 2013-03-15 | 2017-02-22 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| US10167286B2 (en) | 2014-02-11 | 2019-01-01 | Mitokinin, Inc. | Compositions and methods using the same for treatment of neurodegenerative and mitochondrial disease |
| CN107108385B (zh) | 2014-11-14 | 2021-09-24 | 巴斯夫欧洲公司 | 作为硝化抑制剂的苄基炔丙基醚 |
| ES2668688T3 (es) | 2014-12-16 | 2018-05-21 | Omya International Ag | Carbonato de calcio para protección vegetal |
| MA41272A (fr) | 2014-12-23 | 2017-10-31 | Adama Makhteshim Ltd | 5-fluoro-4-imino-3-(alkyle/alkyle substitué)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one en tant que traitement des semences |
| SG11201703880VA (en) * | 2014-12-23 | 2017-07-28 | Novartis Ag | Triazolopyrimidine compounds and uses thereof |
| GB201501017D0 (en) | 2014-12-23 | 2015-03-04 | Immatics Biotechnologies Gmbh | Novel peptides and combination of peptides for use in immunotherapy against hepatocellular carcinoma (HCC) and other cancers |
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