TW200918047A - Novel compounds - Google Patents

Info

Publication number

TW200918047A

TW200918047A TW097138109A TW97138109A TW200918047A TW 200918047 A TW200918047 A TW 200918047A TW 097138109 A TW097138109 A TW 097138109A TW 97138109 A TW97138109 A TW 97138109A TW 200918047 A TW200918047 A TW 200918047A

Authority

TW

Taiwan

Prior art keywords

naphthoquinone

dimethyl

hydroxy

lls

oxazol

Prior art date

2007-10-04

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 320
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 229930192627 Naphthoquinone Natural products 0.000 claims description 335
• 150000002791 naphthoquinones Chemical class 0.000 claims description 335
• -1 alkyl sulfide Chemical compound 0.000 claims description 251
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 234
• 239000007789 gas Substances 0.000 claims description 98
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 77
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 54
• 239000002253 acid Substances 0.000 claims description 54
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 52
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 38
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 34
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 32
• 150000002148 esters Chemical class 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 31
• 239000003795 chemical substances by application Substances 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 229910052731 fluorine Chemical group 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 claims description 22
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 208000006673 asthma Diseases 0.000 claims description 21
• 239000011737 fluorine Substances 0.000 claims description 21
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 17
• 239000001301 oxygen Substances 0.000 claims description 17
• 235000021419 vinegar Nutrition 0.000 claims description 17
• KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 239000000052 vinegar Substances 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• 239000011593 sulfur Substances 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 9
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 9
• 125000003277 amino group Chemical group 0.000 claims description 8
• 125000002837 carbocyclic group Chemical group 0.000 claims description 8
• 101150010802 CVC2 gene Proteins 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 6
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 125000006239 protecting group Chemical group 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
• LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 5
• CFGQZVOVFIZRMN-UHFFFAOYSA-N 2-methylfuran-3-carboxylic acid Chemical compound CC=1OC=CC=1C(O)=O CFGQZVOVFIZRMN-UHFFFAOYSA-N 0.000 claims description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 201000010105 allergic rhinitis Diseases 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
• 150000002576 ketones Chemical class 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 206010039083 rhinitis Diseases 0.000 claims description 5
• 229910052707 ruthenium Inorganic materials 0.000 claims description 5
• JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 claims description 4
• HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 claims description 4
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
• 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
• BNYIQEFWGSXIKQ-UHFFFAOYSA-M 3-methylfuran-2-carboxylate Chemical compound CC=1C=COC=1C([O-])=O BNYIQEFWGSXIKQ-UHFFFAOYSA-M 0.000 claims description 3
• DHHFGQADZVYGIE-UHFFFAOYSA-N 9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(=O)O DHHFGQADZVYGIE-UHFFFAOYSA-N 0.000 claims description 3
• 150000003973 alkyl amines Chemical class 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• KSJJMSKNZVXAND-UHFFFAOYSA-N 1-cyanocyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C#N)CC1 KSJJMSKNZVXAND-UHFFFAOYSA-N 0.000 claims description 2
• HPOWDCXQUZLJRQ-UHFFFAOYSA-N 1-methoxycyclopropane-1-carboxylic acid Chemical compound COC1(C(O)=O)CC1 HPOWDCXQUZLJRQ-UHFFFAOYSA-N 0.000 claims description 2
• OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• ZYLHDTBQHXSLEZ-UHFFFAOYSA-N 3-decoxypropanoic acid Chemical compound CCCCCCCCCCOCCC(O)=O ZYLHDTBQHXSLEZ-UHFFFAOYSA-N 0.000 claims description 2
• YSIKHBWUBSFBRZ-UHFFFAOYSA-N 3-methoxypropanoic acid Chemical compound COCCC(O)=O YSIKHBWUBSFBRZ-UHFFFAOYSA-N 0.000 claims description 2
• DYUOSEZDTBDMGH-UHFFFAOYSA-N 3-sulfanylfuran-2-carboxylic acid Chemical compound OC(=O)C=1OC=CC=1S DYUOSEZDTBDMGH-UHFFFAOYSA-N 0.000 claims description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
• 206010020751 Hypersensitivity Diseases 0.000 claims description 2
• 208000026935 allergic disease Diseases 0.000 claims description 2
• 230000000739 chaotic effect Effects 0.000 claims description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 69
• ZGWGSEUMABQEMD-UHFFFAOYSA-N 4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=CSC=1C(O)=O ZGWGSEUMABQEMD-UHFFFAOYSA-N 0.000 claims 3
• QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
• IKUWHVIKVZSENZ-UHFFFAOYSA-N 2-butan-2-yloxyacetic acid Chemical compound CCC(C)OCC(O)=O IKUWHVIKVZSENZ-UHFFFAOYSA-N 0.000 claims 1
• WZROSPHFTWMIGM-UHFFFAOYSA-N 2-decoxyacetic acid Chemical compound CCCCCCCCCCOCC(O)=O WZROSPHFTWMIGM-UHFFFAOYSA-N 0.000 claims 1
• WMQAQMYIZDJCDJ-UHFFFAOYSA-N 2-methyloxolane-2-carboxylic acid Chemical compound OC(=O)C1(C)CCCO1 WMQAQMYIZDJCDJ-UHFFFAOYSA-N 0.000 claims 1
• CLIZOUKKYIGODI-UHFFFAOYSA-N 4-methyloxadiazole-5-carboxylic acid Chemical compound CC=1N=NOC=1C(O)=O CLIZOUKKYIGODI-UHFFFAOYSA-N 0.000 claims 1
• BJNGCQBVYGFTRK-UHFFFAOYSA-N C1=COC(=C1C(=O)O)S Chemical compound C1=COC(=C1C(=O)O)S BJNGCQBVYGFTRK-UHFFFAOYSA-N 0.000 claims 1
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
• QJMUGAHEYCGFIY-UHFFFAOYSA-N OC(=O)C1=NOC(S)=C1 Chemical compound OC(=O)C1=NOC(S)=C1 QJMUGAHEYCGFIY-UHFFFAOYSA-N 0.000 claims 1
• 101100497572 Pisum sativum CVCA gene Proteins 0.000 claims 1
• 230000002378 acidificating effect Effects 0.000 claims 1
• 230000007815 allergy Effects 0.000 claims 1
• 125000000732 arylene group Chemical group 0.000 claims 1
• GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
• YFPCLQKFNXUAAK-UHFFFAOYSA-N cyclopentyl acetate Chemical compound CC(=O)OC1CCCC1 YFPCLQKFNXUAAK-UHFFFAOYSA-N 0.000 claims 1
• 125000005265 dialkylamine group Chemical group 0.000 claims 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
• 239000010433 feldspar Substances 0.000 claims 1
• QEWYKACRFQMRMB-UHFFFAOYSA-M fluoroacetate Chemical compound [O-]C(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-M 0.000 claims 1
• ULURQBQIQKKDEL-UHFFFAOYSA-N indazol-1-yl acetate Chemical compound C1=CC=C2N(OC(=O)C)N=CC2=C1 ULURQBQIQKKDEL-UHFFFAOYSA-N 0.000 claims 1
• 125000006301 indolyl methyl group Chemical group 0.000 claims 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
• DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims 1
• UJJLJRQIPMGXEZ-SCSAIBSYSA-N tetrahydrofuran-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCO1 UJJLJRQIPMGXEZ-SCSAIBSYSA-N 0.000 claims 1
• 150000003573 thiols Chemical class 0.000 claims 1
• 229940070710 valerate Drugs 0.000 claims 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 227
• 238000002360 preparation method Methods 0.000 abstract description 24
• 230000008569 process Effects 0.000 abstract description 9
• 238000002560 therapeutic procedure Methods 0.000 abstract description 3
• 239000000543 intermediate Substances 0.000 description 319
• 238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 264
• 238000005481 NMR spectroscopy Methods 0.000 description 165
• 239000013067 intermediate product Substances 0.000 description 146
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
• 101150041968 CDC13 gene Proteins 0.000 description 135
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 135
• 239000000203 mixture Substances 0.000 description 122
• 239000002585 base Substances 0.000 description 120
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 100
• 239000000243 solution Substances 0.000 description 88
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 83
• 125000004149 thio group Chemical group *S* 0.000 description 75
• 206010057190 Respiratory tract infections Diseases 0.000 description 68
• 235000019439 ethyl acetate Nutrition 0.000 description 68
• 239000000047 product Substances 0.000 description 64
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 58
• REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 48
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• 239000003112 inhibitor Substances 0.000 description 37
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• 239000002904 solvent Substances 0.000 description 32
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 239000012074 organic phase Substances 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 239000007787 solid Substances 0.000 description 23
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
• 239000012267 brine Substances 0.000 description 22
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 21
• 238000002953 preparative HPLC Methods 0.000 description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
• 238000003756 stirring Methods 0.000 description 20
• 201000010099 disease Diseases 0.000 description 19
• 238000001914 filtration Methods 0.000 description 19
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 18
• LHMHCLYDBQOYTO-UHFFFAOYSA-N bromofluoromethane Chemical compound FCBr LHMHCLYDBQOYTO-UHFFFAOYSA-N 0.000 description 18
• 238000000746 purification Methods 0.000 description 18
• 229910052786 argon Inorganic materials 0.000 description 17
• 230000002829 reductive effect Effects 0.000 description 15
• LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 14
• 239000003921 oil Substances 0.000 description 13
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