TW202140473A - Map4k1抑制劑 - Google Patents

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Publication number

TW202140473A

TW202140473A TW110101515A TW110101515A TW202140473A TW 202140473 A TW202140473 A TW 202140473A TW 110101515 A TW110101515 A TW 110101515A TW 110101515 A TW110101515 A TW 110101515A TW 202140473 A TW202140473 A TW 202140473A

Authority

TW

Taiwan

Prior art keywords

compound

alkyl

pharmaceutically acceptable

acceptable salt

cycloalkyl

Prior art date

2020-01-15

Links

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• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title abstract description 55
• 150000001875 compounds Chemical class 0.000 claims abstract description 464
• 150000003839 salts Chemical class 0.000 claims abstract description 124
• 101001059991 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 1 Proteins 0.000 claims abstract description 73
• 102100028199 Mitogen-activated protein kinase kinase kinase kinase 1 Human genes 0.000 claims abstract description 73
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
• 201000010099 disease Diseases 0.000 claims abstract description 22
• 208000035475 disorder Diseases 0.000 claims abstract description 10
• 238000000034 method Methods 0.000 claims description 133
• -1 trifluoroisopropyl Chemical group 0.000 claims description 110
• 125000000217 alkyl group Chemical group 0.000 claims description 80
• 206010028980 Neoplasm Diseases 0.000 claims description 73
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 201000011510 cancer Diseases 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 239000001257 hydrogen Substances 0.000 claims description 31
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 28
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 150000001721 carbon Chemical group 0.000 claims description 16
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 206010025323 Lymphomas Diseases 0.000 claims description 12
• 239000002246 antineoplastic agent Substances 0.000 claims description 11
• 230000001419 dependent effect Effects 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 238000006467 substitution reaction Methods 0.000 claims description 10
• 229910052727 yttrium Inorganic materials 0.000 claims description 10
• 229910052796 boron Inorganic materials 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 230000009385 viral infection Effects 0.000 claims description 9
• 208000036142 Viral infection Diseases 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000003566 oxetanyl group Chemical group 0.000 claims description 8
• 206010006187 Breast cancer Diseases 0.000 claims description 7
• 208000026310 Breast neoplasm Diseases 0.000 claims description 7
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
• 230000002708 enhancing effect Effects 0.000 claims description 7
• 208000014018 liver neoplasm Diseases 0.000 claims description 7
• 201000005202 lung cancer Diseases 0.000 claims description 7
• 208000020816 lung neoplasm Diseases 0.000 claims description 7
• 206010033128 Ovarian cancer Diseases 0.000 claims description 6
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• 201000007270 liver cancer Diseases 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 5
• 206010017758 gastric cancer Diseases 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 201000011549 stomach cancer Diseases 0.000 claims description 5
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 206010038389 Renal cancer Diseases 0.000 claims description 4
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 4
• 201000010881 cervical cancer Diseases 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 201000010536 head and neck cancer Diseases 0.000 claims description 4
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 201000010982 kidney cancer Diseases 0.000 claims description 4
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
• 201000002528 pancreatic cancer Diseases 0.000 claims description 4
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 230000028993 immune response Effects 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
• AEFDLTFVZBBKQH-UHFFFAOYSA-N 1-methyl-2-propan-2-yloxypyrrolidine Chemical group CC(C)OC1CCCN1C AEFDLTFVZBBKQH-UHFFFAOYSA-N 0.000 claims description 2
• WWYVZTLIFYLZFM-UHFFFAOYSA-N 1-methylazetidine Chemical group CN1CCC1 WWYVZTLIFYLZFM-UHFFFAOYSA-N 0.000 claims description 2
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
• 206010005003 Bladder cancer Diseases 0.000 claims description 2
• 229910005965 SO 2 Inorganic materials 0.000 claims description 2
• 229910021386 carbon form Inorganic materials 0.000 claims description 2
• 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims description 2
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 8
• 230000000694 effects Effects 0.000 abstract description 18
• 230000008901 benefit Effects 0.000 abstract description 3
• 239000000543 intermediate Substances 0.000 description 431
• 238000005160 1H NMR spectroscopy Methods 0.000 description 199
• 239000011541 reaction mixture Substances 0.000 description 187
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 167
• 239000000203 mixture Substances 0.000 description 162
• 239000007787 solid Substances 0.000 description 148
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 139
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 129
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 117
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 116
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 116
• 239000000243 solution Substances 0.000 description 114
• 239000012044 organic layer Substances 0.000 description 108
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 107
• 238000005481 NMR spectroscopy Methods 0.000 description 85
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 78
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 74
• 230000002829 reductive effect Effects 0.000 description 70
• 239000012071 phase Substances 0.000 description 64
• 238000003818 flash chromatography Methods 0.000 description 63
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 59
• 239000003208 petroleum Substances 0.000 description 51
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
• 239000003921 oil Substances 0.000 description 43
• 239000000741 silica gel Substances 0.000 description 42
• 229910002027 silica gel Inorganic materials 0.000 description 42
• 229920006395 saturated elastomer Polymers 0.000 description 41
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
• 238000010828 elution Methods 0.000 description 35
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
• 239000012299 nitrogen atmosphere Substances 0.000 description 30
• 230000008569 process Effects 0.000 description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
• 238000000746 purification Methods 0.000 description 28
• 239000011734 sodium Substances 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• VVIHTMHKSFGRHR-UHFFFAOYSA-N NC(C)(C)C1=C2C=C(N=CC2=C(C=C1)OC)NC1=NC(=NC=C1)C(C)(C)F Chemical compound NC(C)(C)C1=C2C=C(N=CC2=C(C=C1)OC)NC1=NC(=NC=C1)C(C)(C)F VVIHTMHKSFGRHR-UHFFFAOYSA-N 0.000 description 26
• 150000001335 aliphatic alkanes Chemical class 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
• 238000002360 preparation method Methods 0.000 description 24
• 239000000460 chlorine Substances 0.000 description 23
• 239000013058 crude material Substances 0.000 description 22
• 238000002953 preparative HPLC Methods 0.000 description 22
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 21
• QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 20
• 239000010410 layer Substances 0.000 description 20
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
• 229940045207 immuno-oncology agent Drugs 0.000 description 19
• 239000002584 immunological anticancer agent Substances 0.000 description 19
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• 150000001412 amines Chemical class 0.000 description 18
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 230000008878 coupling Effects 0.000 description 17
• 238000010168 coupling process Methods 0.000 description 17
• 238000005859 coupling reaction Methods 0.000 description 17
• WDVGNXKCFBOKDF-UHFFFAOYSA-N dicyclohexyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane Chemical compound COC1=CC=C(OC)C(C=2C(=CC(=CC=2C(C)C)C(C)C)C(C)C)=C1P(C1CCCCC1)C1CCCCC1 WDVGNXKCFBOKDF-UHFFFAOYSA-N 0.000 description 17
• JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• 239000012267 brine Substances 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 230000002441 reversible effect Effects 0.000 description 16
• 210000004027 cell Anatomy 0.000 description 15
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• 239000005557 antagonist Substances 0.000 description 13
• 150000004982 aromatic amines Chemical class 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 13
• 238000012746 preparative thin layer chromatography Methods 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• 229910004298 SiO 2 Inorganic materials 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 208000009956 adenocarcinoma Diseases 0.000 description 12
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• 239000003795 chemical substances by application Substances 0.000 description 12
• 238000004440 column chromatography Methods 0.000 description 12
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• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
• 235000017557 sodium bicarbonate Nutrition 0.000 description 12
• 239000007858 starting material Substances 0.000 description 12
• 201000009030 Carcinoma Diseases 0.000 description 11
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 0.000 description 11
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 210000001744 T-lymphocyte Anatomy 0.000 description 10
• 238000000926 separation method Methods 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• 230000002378 acidificating effect Effects 0.000 description 9
• 239000003443 antiviral agent Substances 0.000 description 9
• 239000012230 colorless oil Substances 0.000 description 9
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 9
• 235000019441 ethanol Nutrition 0.000 description 9
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
• 235000011056 potassium acetate Nutrition 0.000 description 9
• 206010041823 squamous cell carcinoma Diseases 0.000 description 9
• LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 8
• 206010039491 Sarcoma Diseases 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
• 239000003814 drug Substances 0.000 description 8
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 8
• 239000000463 material Substances 0.000 description 8
• 229910052763 palladium Inorganic materials 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 8
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 7
• ADEKJVNFIQUGRR-UHFFFAOYSA-N 4h-pyridin-3-one Chemical compound O=C1CC=CN=C1 ADEKJVNFIQUGRR-UHFFFAOYSA-N 0.000 description 7
• 102000004190 Enzymes Human genes 0.000 description 7
• 108090000790 Enzymes Proteins 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
• 239000000556 agonist Substances 0.000 description 7
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 229940088598 enzyme Drugs 0.000 description 7
• 238000005984 hydrogenation reaction Methods 0.000 description 7
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• 230000004083 survival effect Effects 0.000 description 7
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 6
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• 102100024216 Programmed cell death 1 ligand 1 Human genes 0.000 description 6
• 102100040678 Programmed cell death protein 1 Human genes 0.000 description 6
• 101710089372 Programmed cell death protein 1 Proteins 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 6
• 229910052805 deuterium Inorganic materials 0.000 description 6
• 239000012065 filter cake Substances 0.000 description 6
• 238000004128 high performance liquid chromatography Methods 0.000 description 6
• 150000002576 ketones Chemical class 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
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