JP7359782B2 - ブルトン型チロシンキナーゼに対する阻害剤 - Google Patents

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Publication number

JP7359782B2

JP7359782B2 JP2020564219A JP2020564219A JP7359782B2 JP 7359782 B2 JP7359782 B2 JP 7359782B2 JP 2020564219 A JP2020564219 A JP 2020564219A JP 2020564219 A JP2020564219 A JP 2020564219A JP 7359782 B2 JP7359782 B2 JP 7359782B2

Authority

JP

Japan

Prior art keywords

methyl

alkyl

membered monocyclic

tert

butyl

Prior art date

2018-05-14

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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• 108010029445 Agammaglobulinaemia Tyrosine Kinase Proteins 0.000 title claims description 4
• 102000001714 Agammaglobulinaemia Tyrosine Kinase Human genes 0.000 title claims 2
• 239000003112 inhibitor Substances 0.000 title description 2
• -1 and R 4 is H Chemical group 0.000 claims description 213
• 125000000217 alkyl group Chemical group 0.000 claims description 210
• 150000001875 compounds Chemical class 0.000 claims description 132
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 94
• 150000003839 salts Chemical class 0.000 claims description 92
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 91
• 125000005843 halogen group Chemical group 0.000 claims description 88
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 87
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 229910052799 carbon Inorganic materials 0.000 claims description 68
• 229920006395 saturated elastomer Polymers 0.000 claims description 45
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000001153 fluoro group Chemical group F* 0.000 claims description 20
• 238000000034 method Methods 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000002950 monocyclic group Chemical group 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 208000035475 disorder Diseases 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 8
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 8
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 8
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 5
• 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 claims description 5
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 5
• 230000005764 inhibitory process Effects 0.000 claims description 5
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 5
• 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000005880 oxathiolanyl group Chemical group 0.000 claims description 5
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 5
• 125000003566 oxetanyl group Chemical group 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000005458 thianyl group Chemical group 0.000 claims description 5
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 5
• 125000001166 thiolanyl group Chemical group 0.000 claims description 5
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 4
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 4
• MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 4
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 150000003536 tetrazoles Chemical class 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 2
• 238000003786 synthesis reaction Methods 0.000 description 521
• 230000015572 biosynthetic process Effects 0.000 description 518
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 442
• 239000007787 solid Substances 0.000 description 269
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 228
• 239000011541 reaction mixture Substances 0.000 description 226
• 235000019439 ethyl acetate Nutrition 0.000 description 221
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 217
• 239000000243 solution Substances 0.000 description 169
• 239000013058 crude material Substances 0.000 description 166
• 238000005160 1H NMR spectroscopy Methods 0.000 description 162
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 148
• 238000010898 silica gel chromatography Methods 0.000 description 136
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 110
• 239000003208 petroleum Substances 0.000 description 105
• 239000000203 mixture Substances 0.000 description 92
• 239000012071 phase Substances 0.000 description 92
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 87
• 238000002953 preparative HPLC Methods 0.000 description 87
• 239000011734 sodium Substances 0.000 description 80
• 239000012043 crude product Substances 0.000 description 77
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 70
• 238000000746 purification Methods 0.000 description 68
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 62
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 59
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 52
• 239000000284 extract Substances 0.000 description 40
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 37
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
• 239000012267 brine Substances 0.000 description 34
• 239000000706 filtrate Substances 0.000 description 34
• 239000003921 oil Substances 0.000 description 34
• 235000019198 oils Nutrition 0.000 description 34
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
• 239000008346 aqueous phase Substances 0.000 description 32
• 150000003840 hydrochlorides Chemical class 0.000 description 32
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 31
• 239000012074 organic phase Substances 0.000 description 29
• PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 28
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 27
• SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 25
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 22
• 239000010410 layer Substances 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 21
• 238000005481 NMR spectroscopy Methods 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 150000001412 amines Chemical class 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• 239000000725 suspension Substances 0.000 description 17
• BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 15
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
• 239000012230 colorless oil Substances 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 13
• 239000007821 HATU Substances 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 12
• 238000012799 strong cation exchange Methods 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 125000004122 cyclic group Chemical group 0.000 description 11
• 239000012065 filter cake Substances 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 125000004452 carbocyclyl group Chemical group 0.000 description 10
• 150000003857 carboxamides Chemical class 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000012299 nitrogen atmosphere Substances 0.000 description 10
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 239000005457 ice water Substances 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• NIZLCZAQXYDEAP-GOSISDBHSA-N 3-tert-butyl-N-[(5R)-8-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,2,4-oxadiazole-5-carboxamide Chemical compound CN1C=CC(NC2=NC(=NC=N2)C2=CC3=C(C=C2)[C@@H](CCN(CC(F)(F)F)C3)NC(=O)C2=NC(=NO2)C(C)(C)C)=N1 NIZLCZAQXYDEAP-GOSISDBHSA-N 0.000 description 8
• XUZPISJJYDZYNH-UHFFFAOYSA-N ClC1=NC(=NC=N1)NC1=NN(C=C1)C Chemical compound ClC1=NC(=NC=N1)NC1=NN(C=C1)C XUZPISJJYDZYNH-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 125000001544 thienyl group Chemical group 0.000 description 8
• LKYNGTHMKCTTQC-UHFFFAOYSA-N 1,2-oxazole-3-carboxamide Chemical compound NC(=O)C=1C=CON=1 LKYNGTHMKCTTQC-UHFFFAOYSA-N 0.000 description 7
• KPYCHKKYQZRCMG-UHFFFAOYSA-N 1-tert-butyl-4-fluoro-N-[[2-methyl-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]methyl]pyrazole-3-carboxamide Chemical compound N1=CN=C(N=C1C1=CC(C)=C(CNC(=O)C=2C(F)=CN(N=2)C(C)(C)C)C=C1)NC=1C=CN(N=1)C KPYCHKKYQZRCMG-UHFFFAOYSA-N 0.000 description 7
• HRJBGLKFODTBMP-UHFFFAOYSA-N 4-[4-(aminomethyl)-3-chlorophenyl]-N-(1-methylpyrazol-4-yl)-1,3,5-triazin-2-amine Chemical compound CN1C=C(NC2=NC=NC(=N2)C2=CC(Cl)=C(CN)C=C2)C=N1 HRJBGLKFODTBMP-UHFFFAOYSA-N 0.000 description 7
• FTBHXXCQCOAUJZ-UHFFFAOYSA-N 4-bromo-2-chloro-3-fluorobenzaldehyde Chemical compound Fc1c(Br)ccc(C=O)c1Cl FTBHXXCQCOAUJZ-UHFFFAOYSA-N 0.000 description 7
• HONOCSADKMFXPU-UHFFFAOYSA-N ClC1=NC(=NC=N1)NC=1C=NN(C=1)C Chemical compound ClC1=NC(=NC=N1)NC=1C=NN(C=1)C HONOCSADKMFXPU-UHFFFAOYSA-N 0.000 description 7
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 7
• 241000124008 Mammalia Species 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• 239000012298 atmosphere Substances 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• CCLMPZVVAADLMR-UHFFFAOYSA-N 4-bromo-2-chloro-3-fluoro-N-methoxy-N-methylbenzamide Chemical compound BrC1=C(C(=C(C(=O)N(C)OC)C=C1)Cl)F CCLMPZVVAADLMR-UHFFFAOYSA-N 0.000 description 6
• GQLSWQNJXOSVNE-UHFFFAOYSA-N 4-bromo-2-chloro-3-methylbenzoic acid Chemical compound CC=1C(=C(C(=O)O)C=CC=1Br)Cl GQLSWQNJXOSVNE-UHFFFAOYSA-N 0.000 description 6
• JYTHJSVWKXEZKT-UHFFFAOYSA-N 5-tert-butyl-N-[[3-fluoro-2-methyl-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]methyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound N1=CN=C(N=C1C1=C(F)C(C)=C(CNC(=O)C2=NOC(=N2)C(C)(C)C)C=C1)NC=1C=CN(N=1)C JYTHJSVWKXEZKT-UHFFFAOYSA-N 0.000 description 6
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
• 235000011114 ammonium hydroxide Nutrition 0.000 description 6
• 125000002619 bicyclic group Chemical group 0.000 description 6
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• UHJUNHQBPUMUJE-LLVKDONJSA-N tert-butyl N-[(1R)-1-[2-chloro-3-fluoro-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]carbamate Chemical compound ClC1=C(C=CC(=C1F)C1=NC=NC(=N1)NC=1C=NN(C=1)C)[C@@H](C)NC(OC(C)(C)C)=O UHJUNHQBPUMUJE-LLVKDONJSA-N 0.000 description 6
• 238000005406 washing Methods 0.000 description 6
• HAEPSDUCMBKJLY-MDTSDYNXSA-N (S)-N-[(1R)-1-(4-bromo-2-chloro-3-fluorophenyl)ethyl]-2-methylpropane-2-sulfinamide Chemical compound BrC1=C(C(=C(C=C1)[C@@H](C)N[S@@](=O)C(C)(C)C)Cl)F HAEPSDUCMBKJLY-MDTSDYNXSA-N 0.000 description 5
• VAELWSLNTRVXQS-UHFFFAOYSA-N 1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC=N1 VAELWSLNTRVXQS-UHFFFAOYSA-N 0.000 description 5
• VMCICDADKZXNHW-UHFFFAOYSA-N 1h-triazin-2-amine Chemical compound NN1NC=CC=N1 VMCICDADKZXNHW-UHFFFAOYSA-N 0.000 description 5
• HPCNLUGLZBINSG-QGZVFWFLSA-N 3-tert-butyl-N-[(5R)-1-fluoro-2-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-5-carboxamide Chemical compound CN1C=CC(NC2=NC(=NC=N2)C2=C(F)C3=C(C=C2)[C@@H](CCCC3)NC(=O)C2=NC(=NO2)C(C)(C)C)=N1 HPCNLUGLZBINSG-QGZVFWFLSA-N 0.000 description 5
• ITFAWOFNJPXZJH-GOSISDBHSA-N 3-tert-butyl-N-[(5R)-3-fluoro-2-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-5-carboxamide Chemical compound CN1C=CC(NC2=NC(=NC=N2)C2=CC3=C(C=C2F)[C@@H](CCCC3)NC(=O)C2=NC(=NO2)C(C)(C)C)=N1 ITFAWOFNJPXZJH-GOSISDBHSA-N 0.000 description 5
• PVPBDHFPWYRRFM-UHFFFAOYSA-N 3-tert-butyl-N-[[2-chloro-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]methyl]-1,2,4-oxadiazole-5-carboxamide Chemical compound C(C)(C)(C)C1=NOC(=N1)C(=O)NCC1=C(C=C(C=C1)C1=NC=NC(=N1)NC1=NN(C=C1)C)Cl PVPBDHFPWYRRFM-UHFFFAOYSA-N 0.000 description 5
• VGGIIQRHNHDAGC-CYBMUJFWSA-N 5-tert-butyl-N-[(1R)-1-[3-chloro-2-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound N(C=1C=NN(C=1)C)C1=NC=NC(=N1)C1=C(Cl)C(C)=C([C@@H](C)NC(=O)C2=NOC(=N2)C(C)(C)C)C=C1 VGGIIQRHNHDAGC-CYBMUJFWSA-N 0.000 description 5
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• KSHWPOZEZUXGEY-DDWIOCJRSA-N 4-[4-[(1R)-1-aminoethyl]-3-(difluoromethyl)-2-fluorophenyl]-N-(1-methylpyrazol-3-yl)-1,3,5-triazin-2-amine hydrochloride Chemical compound C[C@H](C1=C(C(=C(C=C1)C2=NC(=NC=N2)NC3=NN(C=C3)C)F)C(F)F)N.Cl KSHWPOZEZUXGEY-DDWIOCJRSA-N 0.000 description 1
• MQIHWMOKSZPCNN-HNCPQSOCSA-N 4-[4-[(1R)-1-aminoethyl]-3-chloro-2-methylphenyl]-N-(1-methylpyrazol-3-yl)-1,3,5-triazin-2-amine hydrochloride Chemical compound CC1=C(C=CC(=C1Cl)[C@@H](C)N)C2=NC(=NC=N2)NC3=NN(C=C3)C.Cl MQIHWMOKSZPCNN-HNCPQSOCSA-N 0.000 description 1
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• AYQBMZNSJPVADT-UHFFFAOYSA-N 4-bromo-2-chlorobenzonitrile Chemical compound ClC1=CC(Br)=CC=C1C#N AYQBMZNSJPVADT-UHFFFAOYSA-N 0.000 description 1
• ULVCSNKNBWWEMI-UHFFFAOYSA-N 4-bromo-5-fluoro-2-methylbenzonitrile Chemical compound CC1=CC(Br)=C(F)C=C1C#N ULVCSNKNBWWEMI-UHFFFAOYSA-N 0.000 description 1
• QPIBHIXKUQKNFP-UHFFFAOYSA-N 4-chloro-3-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(F)=C1 QPIBHIXKUQKNFP-UHFFFAOYSA-N 0.000 description 1
• DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 1
• NALVGTOMKSKFFV-UHFFFAOYSA-N 4-fluoro-3-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1F NALVGTOMKSKFFV-UHFFFAOYSA-N 0.000 description 1
• SADDXAMAYPJECF-LJQANCHMSA-N 4-tert-butyl-N-[(5R)-8-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,3-oxazole-2-carboxamide Chemical compound C(C)(C)(C)C=1N=C(OC=1)C(=O)N[C@H]1C2=C(CN(CC1)CC(F)(F)F)C=C(C=C2)C1=NC=NC(=N1)NC1=NN(C=C1)C SADDXAMAYPJECF-LJQANCHMSA-N 0.000 description 1
• SADDXAMAYPJECF-IBGZPJMESA-N 4-tert-butyl-N-[(5S)-8-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,3-oxazole-2-carboxamide Chemical compound C(C)(C)(C)C=1N=C(OC=1)C(=O)N[C@@H]1C2=C(CN(CC1)CC(F)(F)F)C=C(C=C2)C1=NC=NC(=N1)NC1=NN(C=C1)C SADDXAMAYPJECF-IBGZPJMESA-N 0.000 description 1
• TXFYIVCEZGFJES-FQEVSTJZSA-N 4-tert-butyl-N-[(5S)-8-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,3-oxazole-2-carboxamide Chemical compound C(C)(C)(C)C=1N=C(OC=1)C(=O)N[C@H]1CCN(CC2=C1C=CC(=C2)C1=NC=NC(=N1)NC=1C=NN(C=1)C)CC(F)(F)F TXFYIVCEZGFJES-FQEVSTJZSA-N 0.000 description 1
• SADDXAMAYPJECF-UHFFFAOYSA-N 4-tert-butyl-N-[8-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,3-oxazole-2-carboxamide Chemical compound C(C)(C)(C)C=1N=C(OC=1)C(=O)NC1C2=C(CN(CC1)CC(F)(F)F)C=C(C=C2)C1=NC=NC(=N1)NC1=NN(C=C1)C SADDXAMAYPJECF-UHFFFAOYSA-N 0.000 description 1
• TXFYIVCEZGFJES-UHFFFAOYSA-N 4-tert-butyl-N-[8-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,3-oxazole-2-carboxamide Chemical compound C(C)(C)(C)C=1N=C(OC=1)C(=O)NC1CCN(CC2=C1C=CC(=C2)C1=NC=NC(=N1)NC=1C=NN(C=1)C)CC(F)(F)F TXFYIVCEZGFJES-UHFFFAOYSA-N 0.000 description 1
• YIBPICLYISLVRY-SFHVURJKSA-N 5-(1-fluoro-2-methylpropan-2-yl)-N-[(5S)-2-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound CN1C=CC(NC2=NC(=NC=N2)C2=CC3=C(C=C2)[C@H](CCCC3)NC(=O)C2=NOC(=N2)C(C)(C)CF)=N1 YIBPICLYISLVRY-SFHVURJKSA-N 0.000 description 1
• YIBPICLYISLVRY-UHFFFAOYSA-N 5-(1-fluoro-2-methylpropan-2-yl)-N-[2-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound CN1C=CC(NC2=NC(=NC=N2)C2=CC3=C(C=C2)C(CCCC3)NC(=O)C2=NOC(=N2)C(C)(C)CF)=N1 YIBPICLYISLVRY-UHFFFAOYSA-N 0.000 description 1
• ILIHQQVGRZDCQR-UHFFFAOYSA-N 5-(2,3-dimethylcyclopropyl)-N-[[2-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]methyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound CC1C(C)C1C1=NC(=NO1)C(=O)NCC1=C(C)C=C(C=C1)C1=NC=NC(NC2=CN(C)N=C2)=N1 ILIHQQVGRZDCQR-UHFFFAOYSA-N 0.000 description 1
• UQOIMQIVCXSJMM-UHFFFAOYSA-N 5-[1-(fluoromethyl)cyclopropyl]-1,2,4-oxadiazole-3-carboxylic acid Chemical compound OC(C1=NOC(C2(CF)CC2)=N1)=O UQOIMQIVCXSJMM-UHFFFAOYSA-N 0.000 description 1
• XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
• BYSOLGDUCRNAER-CYBMUJFWSA-N 5-tert-butyl-N-[(1R)-1-[2-chloro-3-methyl-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C[C@@H](NC(=O)C1=NOC(=N1)C(C)(C)C)C1=C(Cl)C(C)=C(C=C1)C1=NC=NC(NC2=NN(C)C=C2)=N1 BYSOLGDUCRNAER-CYBMUJFWSA-N 0.000 description 1
• HCKPYNBMHZREMZ-CYBMUJFWSA-N 5-tert-butyl-N-[(1R)-1-[2-chloro-3-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound N(C=1C=NN(C=1)C)C1=NC=NC(=N1)C1=C(C)C(Cl)=C([C@@H](C)NC(=O)C2=NOC(=N2)C(C)(C)C)C=C1 HCKPYNBMHZREMZ-CYBMUJFWSA-N 0.000 description 1
• PZRXDYPPKLUUOF-CYBMUJFWSA-N 5-tert-butyl-N-[(1R)-1-[3-chloro-2-methyl-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C[C@@H](NC(=O)C1=NOC(=N1)C(C)(C)C)C1=C(C)C(Cl)=C(C=C1)C1=NC=NC(NC2=NN(C)C=C2)=N1 PZRXDYPPKLUUOF-CYBMUJFWSA-N 0.000 description 1
• CLKSRZIOINZVAR-CYBMUJFWSA-N 5-tert-butyl-N-[(1R)-1-[3-fluoro-2-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C[C@@H](NC(=O)C1=NOC(=N1)C(C)(C)C)C1=C(C)C(F)=C(C=C1)C1=NC=NC(NC2=CN(C)N=C2)=N1 CLKSRZIOINZVAR-CYBMUJFWSA-N 0.000 description 1
• JHONDXKOIDDPBK-NSHDSACASA-N 5-tert-butyl-N-[(1S)-1-[2-(difluoromethyl)-3-fluoro-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@@H](C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC1=NN(C=C1)C)F)C(F)F JHONDXKOIDDPBK-NSHDSACASA-N 0.000 description 1
• LIICPJCVDANXNK-NSHDSACASA-N 5-tert-butyl-N-[(1S)-1-[2-chloro-3-fluoro-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@@H](C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC=1C=NN(C=1)C)F)Cl LIICPJCVDANXNK-NSHDSACASA-N 0.000 description 1
• BYSOLGDUCRNAER-ZDUSSCGKSA-N 5-tert-butyl-N-[(1S)-1-[2-chloro-3-methyl-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@@H](C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC1=NN(C=C1)C)C)Cl BYSOLGDUCRNAER-ZDUSSCGKSA-N 0.000 description 1
• HCKPYNBMHZREMZ-ZDUSSCGKSA-N 5-tert-butyl-N-[(1S)-1-[2-chloro-3-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@@H](C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC=1C=NN(C=1)C)C)Cl HCKPYNBMHZREMZ-ZDUSSCGKSA-N 0.000 description 1
• PZRXDYPPKLUUOF-ZDUSSCGKSA-N 5-tert-butyl-N-[(1S)-1-[3-chloro-2-methyl-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C[C@H](NC(=O)C1=NOC(=N1)C(C)(C)C)C1=C(C)C(Cl)=C(C=C1)C1=NC=NC(NC2=NN(C)C=C2)=N1 PZRXDYPPKLUUOF-ZDUSSCGKSA-N 0.000 description 1
• VGGIIQRHNHDAGC-ZDUSSCGKSA-N 5-tert-butyl-N-[(1S)-1-[3-chloro-2-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@@H](C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC=1C=NN(C=1)C)Cl)C VGGIIQRHNHDAGC-ZDUSSCGKSA-N 0.000 description 1
• CLKSRZIOINZVAR-ZDUSSCGKSA-N 5-tert-butyl-N-[(1S)-1-[3-fluoro-2-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@@H](C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC=1C=NN(C=1)C)F)C CLKSRZIOINZVAR-ZDUSSCGKSA-N 0.000 description 1
• TXHMCINUNWSNQH-AWEZNQCLSA-N 5-tert-butyl-N-[(1S)-1-[3-fluoro-2-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2-oxazole-3-carboxamide Chemical compound C(C)(C)(C)C1=CC(=NO1)C(=O)N[C@@H](C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC=1C=NN(C=1)C)F)C TXHMCINUNWSNQH-AWEZNQCLSA-N 0.000 description 1
• HHYFQLZIOYAJFW-SFHVURJKSA-N 5-tert-butyl-N-[(5S)-1-fluoro-2-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@H]1CCCCC2=C1C=CC(=C2F)C1=NC=NC(=N1)NC=1C=NN(C=1)C HHYFQLZIOYAJFW-SFHVURJKSA-N 0.000 description 1
• NMRQRZRXJMFEAZ-SFHVURJKSA-N 5-tert-butyl-N-[(5S)-2-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound CN1C=CC(NC2=NC(=NC=N2)C2=CC3=C(C=C2)[C@H](CCCC3)NC(=O)C2=NOC(=N2)C(C)(C)C)=N1 NMRQRZRXJMFEAZ-SFHVURJKSA-N 0.000 description 1
• SILQIYJJMKSPTI-IBGZPJMESA-N 5-tert-butyl-N-[(5S)-2-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@H]1CCCCC2=C1C=CC(=C2)C1=NC=NC(=N1)NC=1C=NN(C=1)C SILQIYJJMKSPTI-IBGZPJMESA-N 0.000 description 1
• VYGZPOKLFBJMOB-IBGZPJMESA-N 5-tert-butyl-N-[(5S)-3-fluoro-2-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@H]1CCCCC2=C1C=C(C(=C2)C1=NC=NC(=N1)NC=1C=NN(C=1)C)F VYGZPOKLFBJMOB-IBGZPJMESA-N 0.000 description 1
• CBWBEGZJVZIPIK-SFHVURJKSA-N 5-tert-butyl-N-[(5S)-8-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound CN1C=CC(NC2=NC(=NC=N2)C2=CC3=C(C=C2)[C@H](CCN(CC(F)(F)F)C3)NC(=O)C2=NOC(=N2)C(C)(C)C)=N1 CBWBEGZJVZIPIK-SFHVURJKSA-N 0.000 description 1
• IBTCLYZFKUMUIJ-IBGZPJMESA-N 5-tert-butyl-N-[(5S)-8-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]-2-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2-benzazepin-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)N[C@@H]1C2=C(CN(CC1)CC(F)(F)F)C=C(C=C2)C1=NC=NC(=N1)NC=1C=NN(C=1)C IBTCLYZFKUMUIJ-IBGZPJMESA-N 0.000 description 1
• LIICPJCVDANXNK-UHFFFAOYSA-N 5-tert-butyl-N-[1-[2-chloro-3-fluoro-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)NC(C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC=1C=NN(C=1)C)F)Cl LIICPJCVDANXNK-UHFFFAOYSA-N 0.000 description 1
• PZRXDYPPKLUUOF-UHFFFAOYSA-N 5-tert-butyl-N-[1-[3-chloro-2-methyl-4-[4-[(1-methylpyrazol-3-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound CC(NC(=O)C1=NOC(=N1)C(C)(C)C)C1=C(C)C(Cl)=C(C=C1)C1=NC=NC(NC2=NN(C)C=C2)=N1 PZRXDYPPKLUUOF-UHFFFAOYSA-N 0.000 description 1
• CLKSRZIOINZVAR-UHFFFAOYSA-N 5-tert-butyl-N-[1-[3-fluoro-2-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)NC(C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC=1C=NN(C=1)C)F)C CLKSRZIOINZVAR-UHFFFAOYSA-N 0.000 description 1
• TXHMCINUNWSNQH-UHFFFAOYSA-N 5-tert-butyl-N-[1-[3-fluoro-2-methyl-4-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]phenyl]ethyl]-1,2-oxazole-3-carboxamide Chemical compound C(C)(C)(C)C1=CC(=NO1)C(=O)NC(C)C1=C(C(=C(C=C1)C1=NC=NC(=N1)NC=1C=NN(C=1)C)F)C TXHMCINUNWSNQH-UHFFFAOYSA-N 0.000 description 1
• HHYFQLZIOYAJFW-UHFFFAOYSA-N 5-tert-butyl-N-[1-fluoro-2-[4-[(1-methylpyrazol-4-yl)amino]-1,3,5-triazin-2-yl]-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl]-1,2,4-oxadiazole-3-carboxamide Chemical compound C(C)(C)(C)C1=NC(=NO1)C(=O)NC1CCCCC2=C1C=CC(=C2F)C1=NC=NC(=N1)NC=1C=NN(C=1)C HHYFQLZIOYAJFW-UHFFFAOYSA-N 0.000 description 1
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