CA2633752A1 - Composes anti-viraux - Google Patents

Info

Publication number

CA2633752A1

CA2633752A1 CA002633752A CA2633752A CA2633752A1 CA 2633752 A1 CA2633752 A1 CA 2633752A1 CA 002633752 A CA002633752 A CA 002633752A CA 2633752 A CA2633752 A CA 2633752A CA 2633752 A1 CA2633752 A1 CA 2633752A1

Authority

CA

Canada

Prior art keywords

group

compound

product

hydrogen

c6alkyl

Prior art date

2005-12-21

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 487
• 230000000840 anti-viral effect Effects 0.000 title abstract description 4
• 238000000034 method Methods 0.000 claims abstract description 221
• 238000011282 treatment Methods 0.000 claims abstract description 28
• 241000700605 Viruses Species 0.000 claims abstract description 15
• 239000003814 drug Substances 0.000 claims abstract description 10
• 230000010076 replication Effects 0.000 claims abstract description 10
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
• 230000008569 process Effects 0.000 claims abstract description 6
• -1 hydroxy, mercapto Chemical class 0.000 claims description 391
• 229910052739 hydrogen Inorganic materials 0.000 claims description 120
• 239000001257 hydrogen Substances 0.000 claims description 120
• 125000000217 alkyl group Chemical group 0.000 claims description 73
• 150000003839 salts Chemical class 0.000 claims description 70
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
• 150000002367 halogens Chemical class 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 51
• 125000000623 heterocyclic group Chemical group 0.000 claims description 48
• 125000002947 alkylene group Chemical group 0.000 claims description 34
• 229910019142 PO4 Inorganic materials 0.000 claims description 33
• 125000004043 oxo group Chemical group O=* 0.000 claims description 33
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 33
• 239000010452 phosphate Substances 0.000 claims description 33
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 32
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 32
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 32
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
• 125000004450 alkenylene group Chemical group 0.000 claims description 11
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000004419 alkynylene group Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 9
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 8
• 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 8
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 6
• 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 6
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
• 125000000448 haloarylalkoxy group Chemical group 0.000 claims description 6
• 125000005216 haloheteroaryl group Chemical group 0.000 claims description 6
• 208000015181 infectious disease Diseases 0.000 claims description 6
• 230000003612 virological effect Effects 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
• 210000004185 liver Anatomy 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
• 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 2
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
• 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 2
• 210000004369 blood Anatomy 0.000 claims description 2
• 239000008280 blood Substances 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000004443 haloalkoxycarbonylamino group Chemical group 0.000 claims description 2
• 125000003106 haloaryl group Chemical group 0.000 claims description 2
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 26
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 102200025788 rs179363875 Human genes 0.000 claims 1
• 230000029812 viral genome replication Effects 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 93
• 238000003786 synthesis reaction Methods 0.000 abstract description 7
• 239000000543 intermediate Substances 0.000 abstract description 6
• 241000711549 Hepacivirus C Species 0.000 abstract description 4
• 208000036142 Viral infection Diseases 0.000 abstract description 3
• 230000009385 viral infection Effects 0.000 abstract description 3
• 229940124597 therapeutic agent Drugs 0.000 abstract description 2
• 238000011260 co-administration Methods 0.000 abstract 1
• 238000009472 formulation Methods 0.000 abstract 1
• 239000000047 product Substances 0.000 description 600
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 219
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 196
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 172
• 239000000243 solution Substances 0.000 description 171
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 166
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 161
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 119
• 229910052740 iodine Inorganic materials 0.000 description 108
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 98
• 238000004128 high performance liquid chromatography Methods 0.000 description 96
• 238000005160 1H NMR spectroscopy Methods 0.000 description 91
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
• 229910001868 water Inorganic materials 0.000 description 74
• 239000007787 solid Substances 0.000 description 71
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• 229960000583 acetic acid Drugs 0.000 description 58
• 235000019439 ethyl acetate Nutrition 0.000 description 56
• 238000006243 chemical reaction Methods 0.000 description 52
• 239000002904 solvent Substances 0.000 description 50
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
• 235000019198 oils Nutrition 0.000 description 46
• 239000003921 oil Substances 0.000 description 45
• 102000006255 nuclear receptors Human genes 0.000 description 43
• 108020004017 nuclear receptors Proteins 0.000 description 43
• 238000010992 reflux Methods 0.000 description 38
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
• 238000005481 NMR spectroscopy Methods 0.000 description 30
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
• UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• JUIKCULGDIZNDI-UHFFFAOYSA-N 4-chloro-3-nitrophenol Chemical compound OC1=CC=C(Cl)C([N+]([O-])=O)=C1 JUIKCULGDIZNDI-UHFFFAOYSA-N 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• 239000011541 reaction mixture Substances 0.000 description 25
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 21
• 239000000741 silica gel Substances 0.000 description 21
• 229910002027 silica gel Inorganic materials 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 235000019441 ethanol Nutrition 0.000 description 20
• 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 19
• 125000004432 carbon atom Chemical group C* 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 238000002390 rotary evaporation Methods 0.000 description 18
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
• 239000012267 brine Substances 0.000 description 16
• 238000003818 flash chromatography Methods 0.000 description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 16
• 238000000746 purification Methods 0.000 description 16
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 239000000284 extract Substances 0.000 description 15
• 235000017557 sodium bicarbonate Nutrition 0.000 description 15
• 239000000126 substance Substances 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• 238000001816 cooling Methods 0.000 description 14
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
• YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 13
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 13
• 229910000024 caesium carbonate Inorganic materials 0.000 description 13
• 239000012043 crude product Substances 0.000 description 13
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
• 235000019341 magnesium sulphate Nutrition 0.000 description 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
• 230000002829 reductive effect Effects 0.000 description 13
• 235000011150 stannous chloride Nutrition 0.000 description 13
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 239000005457 ice water Substances 0.000 description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• 125000006413 ring segment Chemical group 0.000 description 12
• 239000002002 slurry Substances 0.000 description 12
• 239000011780 sodium chloride Substances 0.000 description 12
• 229910052938 sodium sulfate Inorganic materials 0.000 description 12
• 235000011152 sodium sulphate Nutrition 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• 235000019270 ammonium chloride Nutrition 0.000 description 11
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 10
• 238000010898 silica gel chromatography Methods 0.000 description 10
• 239000001119 stannous chloride Substances 0.000 description 10
• 239000002585 base Substances 0.000 description 9
• 239000007822 coupling agent Substances 0.000 description 9
• 239000003480 eluent Substances 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 125000005843 halogen group Chemical group 0.000 description 9
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 230000009467 reduction Effects 0.000 description 9
• 241000725303 Human immunodeficiency virus Species 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
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 229910000104 sodium hydride Inorganic materials 0.000 description 8
• 239000012453 solvate Substances 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 8
• 238000001665 trituration Methods 0.000 description 8
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 7
• OGCQDLPUFJZJJX-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanyl-5-methylaniline Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C)C=C1N OGCQDLPUFJZJJX-UHFFFAOYSA-N 0.000 description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• 239000002274 desiccant Substances 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 239000010410 layer Substances 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 229940086542 triethylamine Drugs 0.000 description 7
• SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
• 125000001153 fluoro group Chemical group F* 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
• DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
• 235000011181 potassium carbonates Nutrition 0.000 description 6
• RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
• DMAVUYUFPLGRSW-UHFFFAOYSA-N 1-chloro-4-[(4-methoxyphenyl)methoxy]-2-nitrobenzene Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(Cl)C([N+]([O-])=O)=C1 DMAVUYUFPLGRSW-UHFFFAOYSA-N 0.000 description 5
• AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 5
• WFHPXSHLCFHEIA-UHFFFAOYSA-N 4,6,11-tris(2-methylpropyl)-1,4,6,11-tetraza-5-phosphabicyclo[3.3.3]undecane Chemical compound C1CN(CC(C)C)P2N(CC(C)C)CCN1CCN2CC(C)C WFHPXSHLCFHEIA-UHFFFAOYSA-N 0.000 description 5
• DENKGPBHLYFNGK-UHFFFAOYSA-N 4-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Br)C=C1 DENKGPBHLYFNGK-UHFFFAOYSA-N 0.000 description 5
• BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 5
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
• ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
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