BR112016011851B1 - Derivados de imidazol e pirazol fundidos como moduladores de atividade de tnf - Google Patents

Info

Publication number

BR112016011851B1

BR112016011851B1 BR112016011851-0A BR112016011851A BR112016011851B1 BR 112016011851 B1 BR112016011851 B1 BR 112016011851B1 BR 112016011851 A BR112016011851 A BR 112016011851A BR 112016011851 B1 BR112016011851 B1 BR 112016011851B1

Authority

BR

Brazil

Prior art keywords

alkyl

methyl

optionally substituted

hydroxy

carboxy

Prior art date

2013-12-09

Links

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• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract description 14
• 230000000694 effects Effects 0.000 title abstract description 9
• 150000003217 pyrazoles Chemical class 0.000 title description 3
• 238000011282 treatment Methods 0.000 claims abstract description 62
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
• 208000035475 disorder Diseases 0.000 claims abstract description 19
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 13
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 9
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 8
• 208000030533 eye disease Diseases 0.000 claims abstract description 8
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
• 230000000926 neurological effect Effects 0.000 claims abstract description 8
• 230000002265 prevention Effects 0.000 claims abstract description 8
• 208000002193 Pain Diseases 0.000 claims abstract description 7
• 230000003040 nociceptive effect Effects 0.000 claims abstract description 7
• 230000000771 oncological effect Effects 0.000 claims abstract description 7
• -1 amino, carboxy Chemical group 0.000 claims description 1262
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 325
• 150000001875 compounds Chemical class 0.000 claims description 270
• 125000001424 substituent group Chemical group 0.000 claims description 154
• 229910052739 hydrogen Inorganic materials 0.000 claims description 123
• 239000001257 hydrogen Substances 0.000 claims description 123
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 111
• 229910052736 halogen Chemical group 0.000 claims description 90
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 86
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 83
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 76
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 76
• 150000002367 halogens Chemical group 0.000 claims description 70
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 69
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 69
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 53
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
• 125000004043 oxo group Chemical group O=* 0.000 claims description 42
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 41
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 41
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 150000003839 salts Chemical class 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 32
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 32
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 30
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 28
• 239000012453 solvate Substances 0.000 claims description 28
• 229910020008 S(O) Inorganic materials 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 150000001204 N-oxides Chemical class 0.000 claims description 23
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 20
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• 125000004306 triazinyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims 9
• 238000004519 manufacturing process Methods 0.000 claims 2
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
• 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 abstract description 6
• 208000025966 Neurological disease Diseases 0.000 abstract description 5
• 230000009286 beneficial effect Effects 0.000 abstract description 5
• 102000057041 human TNF Human genes 0.000 abstract description 5
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract description 3
• 201000010099 disease Diseases 0.000 abstract description 3
• 230000003389 potentiating effect Effects 0.000 abstract description 3
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract description 2
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical class C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 abstract description 2
• LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical class C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 abstract description 2
• RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 abstract 1
• 239000000543 intermediate Substances 0.000 description 310
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 163
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 142
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 106
• 238000000034 method Methods 0.000 description 100
• 239000000126 substance Substances 0.000 description 77
• 239000011541 reaction mixture Substances 0.000 description 74
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 59
• 239000000203 mixture Substances 0.000 description 53
• 125000001153 fluoro group Chemical group F* 0.000 description 52
• 235000019439 ethyl acetate Nutrition 0.000 description 51
• 239000007787 solid Substances 0.000 description 51
• 239000002904 solvent Substances 0.000 description 48
• 125000003118 aryl group Chemical group 0.000 description 45
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 44
• 239000000243 solution Substances 0.000 description 44
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 39
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
• 125000005843 halogen group Chemical group 0.000 description 34
• 238000006243 chemical reaction Methods 0.000 description 33
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
• 239000002585 base Substances 0.000 description 29
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 28
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 125000002757 morpholinyl group Chemical group 0.000 description 23
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 22
• 239000000741 silica gel Substances 0.000 description 22
• 229910002027 silica gel Inorganic materials 0.000 description 22
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 21
• 239000012267 brine Substances 0.000 description 21
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 20
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
• 125000006001 difluoroethyl group Chemical group 0.000 description 20
• 125000001246 bromo group Chemical group Br* 0.000 description 19
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
• 125000005213 alkyl heteroaryl group Chemical group 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• 229930182480 glucuronide Natural products 0.000 description 17
• 150000008134 glucuronides Chemical class 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• 239000002253 acid Substances 0.000 description 16
• 239000003054 catalyst Substances 0.000 description 16
• 125000004366 heterocycloalkenyl group Chemical group 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
• 239000000377 silicon dioxide Substances 0.000 description 15
• 229910052938 sodium sulfate Inorganic materials 0.000 description 15
• 235000011152 sodium sulphate Nutrition 0.000 description 15
• 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 description 14
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 14
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 14
• 239000012298 atmosphere Substances 0.000 description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
• 229910052794 bromium Inorganic materials 0.000 description 14
• 239000000460 chlorine Substances 0.000 description 14
• 229910052801 chlorine Inorganic materials 0.000 description 14
• 125000005298 iminyl group Chemical group 0.000 description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
• 235000019341 magnesium sulphate Nutrition 0.000 description 14
• 239000000651 prodrug Substances 0.000 description 14
• 229940002612 prodrug Drugs 0.000 description 14
• 125000003831 tetrazolyl group Chemical group 0.000 description 14
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 13
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 13
• 150000007530 organic bases Chemical class 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 13
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
• 125000001309 chloro group Chemical group Cl* 0.000 description 12
• 125000003386 piperidinyl group Chemical group 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• 235000011181 potassium carbonates Nutrition 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• 229910052723 transition metal Inorganic materials 0.000 description 12
• 150000003624 transition metals Chemical class 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 11
• 150000007529 inorganic bases Chemical class 0.000 description 11
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 10
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
• 235000011054 acetic acid Nutrition 0.000 description 10
• 229960000583 acetic acid Drugs 0.000 description 10
• 239000008346 aqueous phase Substances 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 10
• 125000005215 cycloalkylheteroaryl group Chemical group 0.000 description 10
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• 235000017557 sodium bicarbonate Nutrition 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
• 229910052717 sulfur Inorganic materials 0.000 description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 125000002947 alkylene group Chemical group 0.000 description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
• 125000004193 piperazinyl group Chemical group 0.000 description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 9
• 125000003107 substituted aryl group Chemical group 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
• 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 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 125000003545 alkoxy group Chemical group 0.000 description 8
• 125000002877 alkyl aryl group Chemical group 0.000 description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 description 8
• 125000006310 cycloalkyl amino group Chemical group 0.000 description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
• 125000003566 oxetanyl group Chemical group 0.000 description 8
• 230000008569 process Effects 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 7
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
• 229910001873 dinitrogen Inorganic materials 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 125000001041 indolyl group Chemical group 0.000 description 7
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
• 239000001301 oxygen Substances 0.000 description 7
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 7
• 239000012312 sodium hydride Substances 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• 239000011593 sulfur Chemical group 0.000 description 7
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 7
• ZEZKXPQIDURFKA-UHFFFAOYSA-N 5-bromo-2-iodopyrimidine Chemical compound BrC1=CN=C(I)N=C1 ZEZKXPQIDURFKA-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• 230000001363 autoimmune Effects 0.000 description 6
• 125000002393 azetidinyl group Chemical group 0.000 description 6
• 150000001555 benzenes Chemical group 0.000 description 6
• 150000001602 bicycloalkyls Chemical group 0.000 description 6
• 229910052796 boron Inorganic materials 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 239000013058 crude material Substances 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
• 125000000000 cycloalkoxy group Chemical group 0.000 description 6
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 6
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