PT2861604T - Inibidores macrocíclicos de vírus flaviridae - Google Patents

Info

Publication number

PT2861604T

PT2861604T PT137312039T PT13731203T PT2861604T PT 2861604 T PT2861604 T PT 2861604T PT 137312039 T PT137312039 T PT 137312039T PT 13731203 T PT13731203 T PT 13731203T PT 2861604 T PT2861604 T PT 2861604T

Authority

PT

Portugal

Prior art keywords

alkyl

mmol

aryl

halo

alkoxy

Prior art date

2012-06-08

Links

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• 239000003112 inhibitor Substances 0.000 title claims description 36
• 241000710781 Flaviviridae Species 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims description 301
• -1 cyano, hydroxy Chemical group 0.000 claims description 201
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 150
• 239000000203 mixture Substances 0.000 claims description 150
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 103
• 125000003118 aryl group Chemical group 0.000 claims description 91
• 229910052757 nitrogen Inorganic materials 0.000 claims description 82
• 125000003282 alkyl amino group Chemical group 0.000 claims description 63
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
• 125000001424 substituent group Chemical group 0.000 claims description 57
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 52
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 48
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 125000003545 alkoxy group Chemical group 0.000 claims description 46
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
• 150000002148 esters Chemical class 0.000 claims description 38
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 25
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 25
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 24
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 23
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 22
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims description 22
• 125000002252 acyl group Chemical group 0.000 claims description 20
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 19
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 13
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000000732 arylene group Chemical group 0.000 claims description 11
• 239000002777 nucleoside Substances 0.000 claims description 11
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 10
• 229960000329 ribavirin Drugs 0.000 claims description 10
• HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000005549 heteroarylene group Chemical group 0.000 claims description 9
• 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 8
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
• 229960000517 boceprevir Drugs 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 108010050904 Interferons Proteins 0.000 claims description 6
• 102000014150 Interferons Human genes 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 229940124597 therapeutic agent Drugs 0.000 claims description 6
• 125000005335 azido alkyl group Chemical group 0.000 claims description 5
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 229940047124 interferons Drugs 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 239000002773 nucleotide Substances 0.000 claims description 4
• 125000003729 nucleotide group Chemical group 0.000 claims description 4
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
• TTZHDVOVKQGIBA-IQWMDFIBSA-N sofosbuvir Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@]2(F)C)O)CO[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)OC=2C=CC=CC=2)C=CC(=O)NC1=O TTZHDVOVKQGIBA-IQWMDFIBSA-N 0.000 claims description 4
• BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 claims description 4
• 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 3
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
• 125000005576 pyrimidinylene group Chemical group 0.000 claims description 3
• 229960002063 sofosbuvir Drugs 0.000 claims description 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 229940044616 toll-like receptor 7 agonist Drugs 0.000 claims description 3
• 229940124772 HCV-NS5B polymerase inhibitor Drugs 0.000 claims description 2
• 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 229960002935 telaprevir Drugs 0.000 claims description 2
• 108010017101 telaprevir Proteins 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 22
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 617
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 345
• 239000000243 solution Substances 0.000 description 220
• 235000019439 ethyl acetate Nutrition 0.000 description 203
• 239000011541 reaction mixture Substances 0.000 description 163
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 159
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 150
• 239000007787 solid Substances 0.000 description 136
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 124
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 121
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 121
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
• 238000010898 silica gel chromatography Methods 0.000 description 112
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 106
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 97
• 238000006243 chemical reaction Methods 0.000 description 82
• YUHZIUAREWNXJT-UHFFFAOYSA-N (2-fluoropyridin-3-yl)boronic acid Chemical class OB(O)C1=CC=CN=C1F YUHZIUAREWNXJT-UHFFFAOYSA-N 0.000 description 78
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 70
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 67
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 66
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 62
• 229910052938 sodium sulfate Inorganic materials 0.000 description 55
• 235000011152 sodium sulphate Nutrition 0.000 description 55
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 54
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
• 238000003756 stirring Methods 0.000 description 48
• 239000010410 layer Substances 0.000 description 47
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 44
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 43
• 239000012267 brine Substances 0.000 description 43
• 238000000034 method Methods 0.000 description 41
• 125000005843 halogen group Chemical group 0.000 description 40
• 239000003921 oil Substances 0.000 description 37
• 235000019198 oils Nutrition 0.000 description 36
• 239000003039 volatile agent Substances 0.000 description 36
• 239000002253 acid Substances 0.000 description 35
• 238000011282 treatment Methods 0.000 description 35
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 33
• 239000000047 product Substances 0.000 description 33
• 238000005481 NMR spectroscopy Methods 0.000 description 31
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
• 239000012044 organic layer Substances 0.000 description 27
• 239000002904 solvent Substances 0.000 description 26
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 25
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
• 125000004432 carbon atom Chemical group C* 0.000 description 24
• 239000003054 catalyst Substances 0.000 description 24
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 241000711549 Hepacivirus C Species 0.000 description 21
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
• 150000001412 amines Chemical class 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
• 239000000284 extract Substances 0.000 description 20
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
• 235000019341 magnesium sulphate Nutrition 0.000 description 20
• ZRPFJAPZDXQHSM-UHFFFAOYSA-L 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole;dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)(Cl)=C1N(C=2C(=CC(C)=CC=2C)C)CCN1C1=C(C)C=C(C)C=C1C ZRPFJAPZDXQHSM-UHFFFAOYSA-L 0.000 description 19
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 19
• 239000002585 base Substances 0.000 description 18
• 201000010099 disease Diseases 0.000 description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
• 238000010992 reflux Methods 0.000 description 17
• 239000000725 suspension Substances 0.000 description 17
• 239000012299 nitrogen atmosphere Substances 0.000 description 16
• FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 16
• 150000001336 alkenes Chemical class 0.000 description 15
• 239000012230 colorless oil Substances 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 150000002576 ketones Chemical class 0.000 description 15
• 229920002554 vinyl polymer Polymers 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• 239000000741 silica gel Substances 0.000 description 14
• 229910002027 silica gel Inorganic materials 0.000 description 14
• 239000012258 stirred mixture Substances 0.000 description 13
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 12
• 238000005859 coupling reaction Methods 0.000 description 12
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 12
• 239000008346 aqueous phase Substances 0.000 description 11
• 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 11
• 229910052739 hydrogen Inorganic materials 0.000 description 11
• 239000001257 hydrogen Substances 0.000 description 11
• QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 11
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 10
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 10
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 125000004429 atom Chemical group 0.000 description 10
• 238000010168 coupling process Methods 0.000 description 10
• 229910052805 deuterium Inorganic materials 0.000 description 10
• 239000012442 inert solvent Substances 0.000 description 10
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
• 125000006239 protecting group Chemical group 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 9
• MAQDQJWCSSCURR-UHFFFAOYSA-N 4-[5-(cyclopropanecarbonylamino)-2-(trifluoromethoxy)phenyl]-n-[4-[(4-propylsulfonylpiperazin-1-yl)methyl]phenyl]benzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C=2C(=CC=C(NC(=O)C3CC3)C=2)OC(F)(F)F)C=C1 MAQDQJWCSSCURR-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• 150000001299 aldehydes Chemical class 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• 230000008878 coupling Effects 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
• 241001465754 Metazoa Species 0.000 description 8
• 239000004280 Sodium formate Substances 0.000 description 8
• 208000036142 Viral infection Diseases 0.000 description 8
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
• 150000001345 alkine derivatives Chemical class 0.000 description 8
• 150000001408 amides Chemical class 0.000 description 8
• 150000004820 halides Chemical group 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• 125000005842 heteroatom Chemical group 0.000 description 8
• 239000005457 ice water Substances 0.000 description 8
• 150000002678 macrocyclic compounds Chemical class 0.000 description 8
• MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 8
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
• 235000017557 sodium bicarbonate Nutrition 0.000 description 8
• HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 8
• 235000019254 sodium formate Nutrition 0.000 description 8
• 230000009385 viral infection Effects 0.000 description 8
• LAXRNWSASWOFOT-UHFFFAOYSA-J (cymene)ruthenium dichloride dimer Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ru+2].[Ru+2].CC(C)C1=CC=C(C)C=C1.CC(C)C1=CC=C(C)C=C1 LAXRNWSASWOFOT-UHFFFAOYSA-J 0.000 description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 7
• 239000005695 Ammonium acetate Substances 0.000 description 7
• 241000700605 Viruses Species 0.000 description 7
• 235000019257 ammonium acetate Nutrition 0.000 description 7
• 229940043376 ammonium acetate Drugs 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 238000010511 deprotection reaction Methods 0.000 description 7
• 239000006260 foam Substances 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 238000006722 reduction reaction Methods 0.000 description 7
• 239000000126 substance Substances 0.000 description 7
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
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