NO843455L - Fremgangsmaate til fremstilling av flaven eller tioflavenderivater - Google Patents

Info

Publication number

NO843455L

NO843455L NO843455A NO843455A NO843455L NO 843455 L NO843455 L NO 843455L NO 843455 A NO843455 A NO 843455A NO 843455 A NO843455 A NO 843455A NO 843455 L NO843455 L NO 843455L

Authority

NO

Norway

Prior art keywords

substituted

formula

unsubstituted

phenyl

alkyl

Prior art date

1983-08-31

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 56
• 238000002360 preparation method Methods 0.000 title claims description 17
• 239000000796 flavoring agent Substances 0.000 title 1
• 235000019634 flavors Nutrition 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 292
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 126
• 150000002367 halogens Chemical class 0.000 claims abstract description 123
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 113
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 113
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 58
• 150000003839 salts Chemical class 0.000 claims abstract description 58
• 125000002252 acyl group Chemical group 0.000 claims abstract description 55
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 53
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
• 239000001257 hydrogen Substances 0.000 claims abstract description 42
• 239000011593 sulfur Substances 0.000 claims abstract description 41
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 41
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 37
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
• 239000001301 oxygen Substances 0.000 claims abstract description 29
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 23
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 21
• 150000001721 carbon Chemical group 0.000 claims abstract description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
• 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 17
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 10
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims abstract description 6
• 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
• -1 2-acetoxy-2-phenylethyl Chemical group 0.000 claims description 268
• 125000000217 alkyl group Chemical group 0.000 claims description 135
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
• 125000003545 alkoxy group Chemical group 0.000 claims description 60
• 125000003282 alkyl amino group Chemical group 0.000 claims description 60
• 239000002253 acid Substances 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 48
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 42
• 125000004414 alkyl thio group Chemical group 0.000 claims description 41
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 40
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 239000000203 mixture Substances 0.000 claims description 35
• 125000005237 alkyleneamino group Chemical group 0.000 claims description 29
• 229910052796 boron Inorganic materials 0.000 claims description 28
• 229910052727 yttrium Inorganic materials 0.000 claims description 28
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
• 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 23
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000004423 acyloxy group Chemical group 0.000 claims description 21
• 125000004442 acylamino group Chemical group 0.000 claims description 19
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 150000004820 halides Chemical class 0.000 claims description 17
• 125000001931 aliphatic group Chemical group 0.000 claims description 16
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 16
• 125000005605 benzo group Chemical group 0.000 claims description 15
• 230000008569 process Effects 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 239000005864 Sulphur Substances 0.000 claims description 12
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
• 239000011707 mineral Substances 0.000 claims description 9
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
• 125000001302 tertiary amino group Chemical group 0.000 claims description 8
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
• 150000008064 anhydrides Chemical class 0.000 claims description 6
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 150000002902 organometallic compounds Chemical class 0.000 claims description 6
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
• 125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
• LRMJVYUTQDYWMS-UHFFFAOYSA-N 4-ethoxy-2-phenyl-2h-chromene-3-carbaldehyde Chemical compound O1C2=CC=CC=C2C(OCC)=C(C=O)C1C1=CC=CC=C1 LRMJVYUTQDYWMS-UHFFFAOYSA-N 0.000 claims description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
• 125000005110 aryl thio group Chemical group 0.000 claims description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• 230000003287 optical effect Effects 0.000 claims description 3
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
• 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
• 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
• 239000004215 Carbon black (E152) Substances 0.000 abstract description 4
• 229930195733 hydrocarbon Natural products 0.000 abstract description 4
• 201000010099 disease Diseases 0.000 abstract description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
• 208000019423 liver disease Diseases 0.000 abstract 1
• 210000002345 respiratory system Anatomy 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 50
• 238000006243 chemical reaction Methods 0.000 description 42
• 239000000243 solution Substances 0.000 description 39
• 229910052740 iodine Inorganic materials 0.000 description 31
• 150000002430 hydrocarbons Chemical group 0.000 description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
• 125000003396 thiol group Chemical class [H]S* 0.000 description 23
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• 150000007513 acids Chemical class 0.000 description 19
• 239000007787 solid Substances 0.000 description 19
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
• 239000013078 crystal Substances 0.000 description 18
• 239000007858 starting material Substances 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• AIOQBOPOGHAITF-UHFFFAOYSA-N 4-chloro-2-phenyl-2h-chromene-3-carbaldehyde Chemical class O1C2=CC=CC=C2C(Cl)=C(C=O)C1C1=CC=CC=C1 AIOQBOPOGHAITF-UHFFFAOYSA-N 0.000 description 15
• 239000013543 active substance Substances 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
• 238000007792 addition Methods 0.000 description 13
• HJSTVTHRVHYLCP-UHFFFAOYSA-N 3-chloro-2-phenyl-2h-chromene-4-carbaldehyde Chemical compound ClC1=C(C=O)C2=CC=CC=C2OC1C1=CC=CC=C1 HJSTVTHRVHYLCP-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 150000003254 radicals Chemical class 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 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 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
• 229910021529 ammonia Inorganic materials 0.000 description 9
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
• 235000019341 magnesium sulphate Nutrition 0.000 description 9
• 210000003097 mucus Anatomy 0.000 description 9
• 230000003647 oxidation Effects 0.000 description 9
• 238000007254 oxidation reaction Methods 0.000 description 9
• 230000009467 reduction Effects 0.000 description 9
• 238000006722 reduction reaction Methods 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 229910052783 alkali metal Inorganic materials 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 238000001704 evaporation Methods 0.000 description 8
• 230000008020 evaporation Effects 0.000 description 8
• 235000010755 mineral Nutrition 0.000 description 8
• 239000002244 precipitate Substances 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• LVYGFGUAYQPIOM-UHFFFAOYSA-N sulfanyl thiocyanate Chemical compound SSC#N LVYGFGUAYQPIOM-UHFFFAOYSA-N 0.000 description 8
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 150000003335 secondary amines Chemical class 0.000 description 7
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 7
• BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 6
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
• 108010010803 Gelatin Proteins 0.000 description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 6
• 238000004440 column chromatography Methods 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• 125000000524 functional group Chemical group 0.000 description 6
• 239000008273 gelatin Substances 0.000 description 6
• 229920000159 gelatin Polymers 0.000 description 6
• 235000019322 gelatine Nutrition 0.000 description 6
• 235000011852 gelatine desserts Nutrition 0.000 description 6
• 125000002950 monocyclic group Chemical group 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• 230000009471 action Effects 0.000 description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 239000000284 extract Substances 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 229910052749 magnesium Inorganic materials 0.000 description 5
• 125000001979 organolithium group Chemical group 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 238000006467 substitution reaction Methods 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical group FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 5
• MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 4
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
• 239000004593 Epoxy Substances 0.000 description 4
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
• 241000124008 Mammalia Species 0.000 description 4
• 241001465754 Metazoa Species 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• 241000699670 Mus sp. Species 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• 238000005481 NMR spectroscopy Methods 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 241000700159 Rattus Species 0.000 description 4
• 229910004298 SiO 2 Inorganic materials 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
• 125000002947 alkylene group Chemical group 0.000 description 4
• 239000000427 antigen Substances 0.000 description 4
• 108091007433 antigens Proteins 0.000 description 4
• 102000036639 antigens Human genes 0.000 description 4
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 4
• 238000009835 boiling Methods 0.000 description 4
• 244000309464 bull Species 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 229950005499 carbon tetrachloride Drugs 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 125000001072 heteroaryl group Chemical group 0.000 description 4
• 150000007857 hydrazones Chemical class 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 210000002540 macrophage Anatomy 0.000 description 4
• 239000011777 magnesium Substances 0.000 description 4
• 235000019359 magnesium stearate Nutrition 0.000 description 4
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
• 229910052751 metal Inorganic materials 0.000 description 4
• 239000002184 metal Substances 0.000 description 4
• 239000012074 organic phase Substances 0.000 description 4
• 125000002734 organomagnesium group Chemical group 0.000 description 4
• 229920001223 polyethylene glycol Polymers 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 229920001592 potato starch Polymers 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
• 239000000454 talc Substances 0.000 description 4
• 229910052623 talc Inorganic materials 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 230000032258 transport Effects 0.000 description 4
• 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 4
• 229910052725 zinc Inorganic materials 0.000 description 4
• 239000011701 zinc Substances 0.000 description 4
• MVXGONWVLZTNHV-UHFFFAOYSA-N 1-(4-chloro-2-phenyl-2h-chromen-3-yl)ethanol Chemical compound CC(O)C1=C(Cl)C2=CC=CC=C2OC1C1=CC=CC=C1 MVXGONWVLZTNHV-UHFFFAOYSA-N 0.000 description 3
• ZKDGKVJIXYRNTI-UHFFFAOYSA-N 4-chloro-8-methoxy-2-phenyl-2h-thiochromene-3-carbaldehyde Chemical compound S1C=2C(OC)=CC=CC=2C(Cl)=C(C=O)C1C1=CC=CC=C1 ZKDGKVJIXYRNTI-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
• 229930006000 Sucrose Natural products 0.000 description 3
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
• 239000000443 aerosol Substances 0.000 description 3
• CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 3
• 150000001735 carboxylic acids Chemical class 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 230000008859 change Effects 0.000 description 3
• KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• 239000008119 colloidal silica Substances 0.000 description 3
• 230000008025 crystallization Effects 0.000 description 3
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
• 239000008298 dragée Substances 0.000 description 3
• 210000003238 esophagus Anatomy 0.000 description 3
• 238000000605 extraction Methods 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 206010019692 hepatic necrosis Diseases 0.000 description 3
• 208000006454 hepatitis Diseases 0.000 description 3
• 231100000283 hepatitis Toxicity 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• 150000002391 heterocyclic compounds Chemical class 0.000 description 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
• 230000003301 hydrolyzing effect Effects 0.000 description 3
• 230000002519 immonomodulatory effect Effects 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 229910052744 lithium Inorganic materials 0.000 description 3
• 239000012280 lithium aluminium hydride Substances 0.000 description 3
• 231100000149 liver necrosis Toxicity 0.000 description 3
• 229910052987 metal hydride Inorganic materials 0.000 description 3
• 150000004681 metal hydrides Chemical class 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• FNGIVWJCCYYITR-UHFFFAOYSA-N n-[(4-chloro-2-phenyl-2h-chromen-3-yl)methylidene]hydroxylamine Chemical compound ON=CC1=C(Cl)C2=CC=CC=C2OC1C1=CC=CC=C1 FNGIVWJCCYYITR-UHFFFAOYSA-N 0.000 description 3
• 150000002923 oximes Chemical class 0.000 description 3
• 125000004043 oxo group Chemical group O=* 0.000 description 3
• 230000035699 permeability Effects 0.000 description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
• 235000011007 phosphoric acid Nutrition 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 239000003380 propellant Substances 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
• 230000000638 stimulation Effects 0.000 description 3
• 239000005720 sucrose Substances 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• ZXMWWPQQIOGJFQ-UHFFFAOYSA-N (4-chloro-2-phenyl-2h-chromen-3-yl)methanol Chemical class OCC1=C(Cl)C2=CC=CC=C2OC1C1=CC=CC=C1 ZXMWWPQQIOGJFQ-UHFFFAOYSA-N 0.000 description 2
• SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
• SVLLSTJAEDNMNI-UHFFFAOYSA-N 2-[(3-formyl-2-phenyl-2h-chromen-4-yl)sulfanyl]acetic acid Chemical compound O1C2=CC=CC=C2C(SCC(=O)O)=C(C=O)C1C1=CC=CC=C1 SVLLSTJAEDNMNI-UHFFFAOYSA-N 0.000 description 2
• JBOOGXCLXZNOJC-UHFFFAOYSA-N 2-phenyl-2h-chromene-3-carboxylic acid Chemical class OC(=O)C1=CC2=CC=CC=C2OC1C1=CC=CC=C1 JBOOGXCLXZNOJC-UHFFFAOYSA-N 0.000 description 2
• PVIUJRZCFXHWSL-UHFFFAOYSA-N 4-benzylsulfanyl-2-phenyl-2h-chromene-3-carbaldehyde Chemical class C12=CC=CC=C2OC(C=2C=CC=CC=2)C(C=O)=C1SCC1=CC=CC=C1 PVIUJRZCFXHWSL-UHFFFAOYSA-N 0.000 description 2
• NZIOIIGPSQJCCH-UHFFFAOYSA-N 4-chloro-2-phenyl-2h-chromene-3-carbonitrile Chemical compound O1C2=CC=CC=C2C(Cl)=C(C#N)C1C1=CC=CC=C1 NZIOIIGPSQJCCH-UHFFFAOYSA-N 0.000 description 2
• JMWXOMKRMBYZGH-UHFFFAOYSA-N 4-chloro-2-phenyl-2h-chromene-3-carboxylic acid Chemical class OC(=O)C1=C(Cl)C2=CC=CC=C2OC1C1=CC=CC=C1 JMWXOMKRMBYZGH-UHFFFAOYSA-N 0.000 description 2
• HMTNBUZDRIFMBW-UHFFFAOYSA-N 4-methoxy-2-phenyl-2h-chromene-3-carbaldehyde Chemical class O1C2=CC=CC=C2C(OC)=C(C=O)C1C1=CC=CC=C1 HMTNBUZDRIFMBW-UHFFFAOYSA-N 0.000 description 2
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
• 244000215068 Acacia senegal Species 0.000 description 2
• 108010088751 Albumins Proteins 0.000 description 2
• 102000009027 Albumins Human genes 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 229920000945 Amylopectin Polymers 0.000 description 2
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• 241000700198 Cavia Species 0.000 description 2
• 244000060011 Cocos nucifera Species 0.000 description 2
• 235000013162 Cocos nucifera Nutrition 0.000 description 2
• 229920002261 Corn starch Polymers 0.000 description 2
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• 229920000084 Gum arabic Polymers 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
• 206010028980 Neoplasm Diseases 0.000 description 2
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
• 206010030113 Oedema Diseases 0.000 description 2
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
• 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 2
• 239000000205 acacia gum Substances 0.000 description 2
• 235000010489 acacia gum Nutrition 0.000 description 2
• 150000001241 acetals Chemical class 0.000 description 2
• 150000001242 acetic acid derivatives Chemical class 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 230000001476 alcoholic effect Effects 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 150000001335 aliphatic alkanes Chemical class 0.000 description 2
• 150000001340 alkali metals Chemical class 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 150000003973 alkyl amines Chemical class 0.000 description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
• 125000005907 alkyl ester group Chemical group 0.000 description 2
• 150000001350 alkyl halides Chemical class 0.000 description 2
• 125000005277 alkyl imino group Chemical group 0.000 description 2
• 125000000304 alkynyl group Chemical group 0.000 description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
• 125000003368 amide group Chemical group 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 150000003863 ammonium salts Chemical class 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
• 239000012298 atmosphere Substances 0.000 description 2
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 210000000621 bronchi Anatomy 0.000 description 2
• 235000014121 butter Nutrition 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 210000004027 cell Anatomy 0.000 description 2
• 230000007969 cellular immunity Effects 0.000 description 2
• 239000001913 cellulose Substances 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 239000007795 chemical reaction product Substances 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• 150000001805 chlorine compounds Chemical class 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 238000003776 cleavage reaction Methods 0.000 description 2
• 229910052681 coesite Inorganic materials 0.000 description 2
• 239000008120 corn starch Substances 0.000 description 2
• 229910052906 cristobalite Inorganic materials 0.000 description 2
• 239000013058 crude material Substances 0.000 description 2
• 239000010779 crude oil Substances 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
• 125000000753 cycloalkyl group Chemical group 0.000 description 2
• 238000006114 decarboxylation reaction Methods 0.000 description 2
• 230000007123 defense Effects 0.000 description 2
• 239000012024 dehydrating agents‎ Substances 0.000 description 2
• 150000008049 diazo compounds Chemical class 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
• WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
• 239000000975 dye Substances 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• JWFASYDZWYDXDX-UHFFFAOYSA-N ethyl 2-[(3-formyl-2-phenyl-2h-chromen-4-yl)-methylamino]acetate Chemical class O1C2=CC=CC=C2C(N(C)CC(=O)OCC)=C(C=O)C1C1=CC=CC=C1 JWFASYDZWYDXDX-UHFFFAOYSA-N 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 239000011737 fluorine Substances 0.000 description 2
• 238000001640 fractional crystallisation Methods 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 210000004907 gland Anatomy 0.000 description 2
• 229960001340 histamine Drugs 0.000 description 2
• LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
• 150000002466 imines Chemical class 0.000 description 2
• 230000001900 immune effect Effects 0.000 description 2
• 230000036039 immunity Effects 0.000 description 2
• 238000011534 incubation Methods 0.000 description 2
• 239000011261 inert gas Substances 0.000 description 2
• 239000013067 intermediate product Substances 0.000 description 2
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
• 210000004185 liver Anatomy 0.000 description 2
• 230000003908 liver function Effects 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
• 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
• 235000019799 monosodium phosphate Nutrition 0.000 description 2
• GSUMTMZOJQAWLW-UHFFFAOYSA-N n-[(3-chloro-2-phenyl-2h-chromen-4-yl)methylidene]hydroxylamine Chemical compound O1C2=CC=CC=C2C(C=NO)=C(Cl)C1C1=CC=CC=C1 GSUMTMZOJQAWLW-UHFFFAOYSA-N 0.000 description 2
• YMDZXWBFJRPPQA-UHFFFAOYSA-N n-[(4-chloro-8-methoxy-2-phenyl-2h-thiochromen-3-yl)methylidene]hydroxylamine Chemical compound S1C=2C(OC)=CC=CC=2C(Cl)=C(C=NO)C1C1=CC=CC=C1 YMDZXWBFJRPPQA-UHFFFAOYSA-N 0.000 description 2
• 238000006386 neutralization reaction Methods 0.000 description 2
• 150000002825 nitriles Chemical class 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 2
• 239000003921 oil Substances 0.000 description 2
• 210000000056 organ Anatomy 0.000 description 2
• 238000006053 organic reaction Methods 0.000 description 2
• 150000002900 organolithium compounds Chemical class 0.000 description 2
• 125000002524 organometallic group Chemical group 0.000 description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
• WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
• 239000002831 pharmacologic agent Substances 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• 239000011574 phosphorus Substances 0.000 description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 238000012545 processing Methods 0.000 description 2
• 125000004076 pyridyl group Chemical group 0.000 description 2
• 230000000241 respiratory effect Effects 0.000 description 2
• 230000007017 scission Effects 0.000 description 2
• 230000028327 secretion Effects 0.000 description 2
• JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
• 150000007659 semicarbazones Chemical class 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 238000007086 side reaction Methods 0.000 description 2
• 239000000377 silicon dioxide Substances 0.000 description 2
• 235000012239 silicon dioxide Nutrition 0.000 description 2
• 229910001961 silver nitrate Inorganic materials 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 239000000600 sorbitol Substances 0.000 description 2
• 235000010356 sorbitol Nutrition 0.000 description 2
• 239000003381 stabilizer Substances 0.000 description 2
• 229910052682 stishovite Inorganic materials 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 239000002511 suppository base Substances 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
• 229910052905 tridymite Inorganic materials 0.000 description 2
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
• 210000004881 tumor cell Anatomy 0.000 description 2
• 230000007306 turnover Effects 0.000 description 2
• 208000027930 type IV hypersensitivity disease Diseases 0.000 description 2
• LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• 201000001862 viral hepatitis Diseases 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
• MEFKFJOEVLUFAY-UHFFFAOYSA-N (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC(=O)C(Cl)(Cl)Cl MEFKFJOEVLUFAY-UHFFFAOYSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• GVARMVYISSEMJA-UHFFFAOYSA-N (3-chloro-2-phenyl-2h-chromen-4-yl)methanol Chemical compound O1C2=CC=CC=C2C(CO)=C(Cl)C1C1=CC=CC=C1 GVARMVYISSEMJA-UHFFFAOYSA-N 0.000 description 1
• KRZQJTYMFPBBLX-UHFFFAOYSA-N (4-chloro-8-methoxy-2-phenyl-2h-thiochromen-3-yl)methanol Chemical compound S1C=2C(OC)=CC=CC=2C(Cl)=C(CO)C1C1=CC=CC=C1 KRZQJTYMFPBBLX-UHFFFAOYSA-N 0.000 description 1
• BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 1
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
• VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• AECVRIDWNCNIAP-UHFFFAOYSA-N 1-(3-chloro-2-phenyl-2h-chromen-4-yl)ethanol Chemical compound O1C2=CC=CC=C2C(C(O)C)=C(Cl)C1C1=CC=CC=C1 AECVRIDWNCNIAP-UHFFFAOYSA-N 0.000 description 1
• FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 1
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• DZBSPOCNTHKNFL-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methoxy-2-phenyl-2h-chromen-3-yl)ethanone Chemical compound O1C2=CC=CC=C2C(OC)=C(C(=O)C(F)(F)F)C1C1=CC=CC=C1 DZBSPOCNTHKNFL-UHFFFAOYSA-N 0.000 description 1
• XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
• YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• ZBKURGXVANGNSK-UHFFFAOYSA-N 2-phenyl-2h-chromene-3-carbaldehyde Chemical compound O=CC1=CC2=CC=CC=C2OC1C1=CC=CC=C1 ZBKURGXVANGNSK-UHFFFAOYSA-N 0.000 description 1
• GSYUNJHIZVEKFF-UHFFFAOYSA-N 2-phenyl-4-piperidin-1-yl-2h-chromene-3-carbaldehyde Chemical class C12=CC=CC=C2OC(C=2C=CC=CC=2)C(C=O)=C1N1CCCCC1 GSYUNJHIZVEKFF-UHFFFAOYSA-N 0.000 description 1
• OJXOWGJHAMWLIZ-UHFFFAOYSA-N 2-phenyl-4h-chromene Chemical compound O1C2=CC=CC=C2CC=C1C1=CC=CC=C1 OJXOWGJHAMWLIZ-UHFFFAOYSA-N 0.000 description 1
• 125000001241 2-phenylethylthio group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])S* 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• PYNIGAQLLOTBCO-UHFFFAOYSA-N 3-benzyl-2-phenyl-2-sulfanylchromene-4-carbaldehyde Chemical compound C(C1=CC=CC=C1)C=1C(OC2=CC=CC=C2C=1C=O)(C1=CC=CC=C1)S PYNIGAQLLOTBCO-UHFFFAOYSA-N 0.000 description 1
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
• KBCAXKIFJVOVOH-UHFFFAOYSA-N 3-chloro-2-phenyl-2h-chromene-4-carbonitrile Chemical compound ClC1=C(C#N)C2=CC=CC=C2OC1C1=CC=CC=C1 KBCAXKIFJVOVOH-UHFFFAOYSA-N 0.000 description 1
• XBEBWHIBDDYZDM-UHFFFAOYSA-N 3-chloro-2-phenyl-2h-chromene-4-carboxylic acid Chemical compound O1C2=CC=CC=C2C(C(=O)O)=C(Cl)C1C1=CC=CC=C1 XBEBWHIBDDYZDM-UHFFFAOYSA-N 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• BGIKNVAVOXTJPM-UHFFFAOYSA-N 3-ethoxy-2-phenyl-2h-chromene-4-carbaldehyde Chemical compound CCOC1=C(C=O)C2=CC=CC=C2OC1C1=CC=CC=C1 BGIKNVAVOXTJPM-UHFFFAOYSA-N 0.000 description 1
• SVUJRLWTDKSILD-UHFFFAOYSA-N 3-methoxy-2-phenyl-2h-chromene-4-carbaldehyde Chemical compound COC1=C(C=O)C2=CC=CC=C2OC1C1=CC=CC=C1 SVUJRLWTDKSILD-UHFFFAOYSA-N 0.000 description 1
• BUWKIQXGCQUIQI-UHFFFAOYSA-N 4-chloro-8-methoxy-2-phenyl-2h-thiochromene-3-carboxylic acid Chemical compound S1C=2C(OC)=CC=CC=2C(Cl)=C(C(O)=O)C1C1=CC=CC=C1 BUWKIQXGCQUIQI-UHFFFAOYSA-N 0.000 description 1
• SXXKUCVHZMMFIY-UHFFFAOYSA-N 4-methoxy-2-phenyl-2h-chromene Chemical compound O1C2=CC=CC=C2C(OC)=CC1C1=CC=CC=C1 SXXKUCVHZMMFIY-UHFFFAOYSA-N 0.000 description 1
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 208000030090 Acute Disease Diseases 0.000 description 1
• 229910000497 Amalgam Inorganic materials 0.000 description 1
• 208000035143 Bacterial infection Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 208000009079 Bronchial Spasm Diseases 0.000 description 1
• 208000014181 Bronchial disease Diseases 0.000 description 1
• 206010006458 Bronchitis chronic Diseases 0.000 description 1
• 206010006482 Bronchospasm Diseases 0.000 description 1
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
• 208000017667 Chronic Disease Diseases 0.000 description 1
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• 229920002307 Dextran Polymers 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
• 206010019799 Hepatitis viral Diseases 0.000 description 1
• YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• 239000002841 Lewis acid Substances 0.000 description 1
• WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 238000003612 Meerwein-Ponndorf-Verley reduction reaction Methods 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
• 239000002262 Schiff base Substances 0.000 description 1
• 150000004753 Schiff bases Chemical class 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
• 102000003929 Transaminases Human genes 0.000 description 1
• 108090000340 Transaminases Proteins 0.000 description 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
• 208000037084 Viral Human Hepatitis Diseases 0.000 description 1
• 208000036142 Viral infection Diseases 0.000 description 1
• 241000700605 Viruses Species 0.000 description 1
• 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
• XWJZLWQWKDFFOT-UHFFFAOYSA-N [I].O=S=O.C1=CC=NC=C1 Chemical compound [I].O=S=O.C1=CC=NC=C1 XWJZLWQWKDFFOT-UHFFFAOYSA-N 0.000 description 1
• JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
• GIHHTBVRBAHHOB-UHFFFAOYSA-N [W+3] Chemical class [W+3] GIHHTBVRBAHHOB-UHFFFAOYSA-N 0.000 description 1
• GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 238000005903 acid hydrolysis reaction Methods 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 150000003855 acyl compounds Chemical class 0.000 description 1
• 238000006136 alcoholysis reaction Methods 0.000 description 1
• 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000004450 alkenylene group Chemical group 0.000 description 1
• 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
• 150000005215 alkyl ethers Chemical class 0.000 description 1
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
• 238000007098 aminolysis reaction Methods 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 238000005915 ammonolysis reaction Methods 0.000 description 1
• 239000003945 anionic surfactant Substances 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 230000000421 anti-necrotic effect Effects 0.000 description 1
• 239000000010 aprotic solvent Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 125000001769 aryl amino group Chemical group 0.000 description 1
• 150000001502 aryl halides Chemical class 0.000 description 1
• 125000004467 aryl imino group Chemical group 0.000 description 1
• 238000010533 azeotropic distillation Methods 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• 208000022362 bacterial infectious disease Diseases 0.000 description 1
• 238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
• 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
• 150000003939 benzylamines Chemical class 0.000 description 1
• 229960003237 betaine Drugs 0.000 description 1
• MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• YIKMRTHKLRXOBU-UHFFFAOYSA-N bromomethane;triphenylphosphane Chemical compound BrC.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YIKMRTHKLRXOBU-UHFFFAOYSA-N 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 229910052793 cadmium Inorganic materials 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 229960000846 camphor Drugs 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 229910002091 carbon monoxide Inorganic materials 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 150000004653 carbonic acids Chemical class 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• 229920001429 chelating resin Polymers 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 239000002026 chloroform extract Substances 0.000 description 1
• 208000007451 chronic bronchitis Diseases 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 238000004140 cleaning Methods 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 239000000571 coke Substances 0.000 description 1
• 238000004891 communication Methods 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000006482 condensation reaction Methods 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 150000003983 crown ethers Chemical class 0.000 description 1
• 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 1
• 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 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• 231100000135 cytotoxicity Toxicity 0.000 description 1
• 230000003013 cytotoxicity Effects 0.000 description 1
• 231100000263 cytotoxicity test Toxicity 0.000 description 1
• 230000006735 deficit Effects 0.000 description 1
• RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
• NRNFKRFWZQQDMD-UHFFFAOYSA-M dichloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=C(Cl)Cl NRNFKRFWZQQDMD-UHFFFAOYSA-M 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
• 230000008034 disappearance Effects 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• 150000002023 dithiocarboxylic acids Chemical class 0.000 description 1
• GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 210000000981 epithelium Anatomy 0.000 description 1
• 210000003743 erythrocyte Anatomy 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• 238000006266 etherification reaction Methods 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 description 1
• WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
• 150000002191 fatty alcohols Chemical class 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical group O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
• 238000004508 fractional distillation Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000004031 fumaroyl group Chemical group C(\C=C\C(=O)*)(=O)* 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 230000014509 gene expression Effects 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 230000035931 haemagglutination Effects 0.000 description 1
• 150000008282 halocarbons Chemical group 0.000 description 1
• 125000004997 halocarbonyl group Chemical group 0.000 description 1
• 150000002366 halogen compounds Chemical class 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 230000000887 hydrating effect Effects 0.000 description 1
• 230000036571 hydration Effects 0.000 description 1
• 238000006703 hydration reaction Methods 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
• 239000012433 hydrogen halide Substances 0.000 description 1
• 229910000039 hydrogen halide Inorganic materials 0.000 description 1
• 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
• 229940071870 hydroiodic acid Drugs 0.000 description 1
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
• 150000002463 imidates Chemical class 0.000 description 1
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 230000028993 immune response Effects 0.000 description 1
• 230000016784 immunoglobulin production Effects 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 150000004966 inorganic peroxy acids Chemical class 0.000 description 1
• 238000009413 insulation Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical class 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 150000007517 lewis acids Chemical class 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
• 150000002690 malonic acid derivatives Chemical class 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 229910000000 metal hydroxide Inorganic materials 0.000 description 1
• 150000004692 metal hydroxides Chemical class 0.000 description 1
• VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
• CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical group COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• 239000011733 molybdenum Substances 0.000 description 1
• 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
• WKEZHBQACHILEC-UHFFFAOYSA-N molybdenum(3+) Chemical compound [Mo+3] WKEZHBQACHILEC-UHFFFAOYSA-N 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 230000000877 morphologic effect Effects 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 230000003843 mucus production Effects 0.000 description 1
• GRVKDWHXLFEVBP-UHFFFAOYSA-N n-(4-methylphenyl)formamide Chemical compound CC1=CC=C(NC=O)C=C1 GRVKDWHXLFEVBP-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
• 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
• 125000003136 n-heptyl 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])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
• 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 229940097496 nasal spray Drugs 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 229910052759 nickel Inorganic materials 0.000 description 1
• 125000004971 nitroalkyl group Chemical group 0.000 description 1
• 150000002829 nitrogen Chemical class 0.000 description 1
• 125000004433 nitrogen atom Chemical group N* 0.000 description 1
• 229910000510 noble metal Inorganic materials 0.000 description 1
• QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
• 239000002736 nonionic surfactant Substances 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 125000000962 organic group Chemical group 0.000 description 1
• 150000004967 organic peroxy acids Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 239000003791 organic solvent mixture Substances 0.000 description 1
• 150000002901 organomagnesium compounds Chemical class 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical class N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 125000000369 oxido group Chemical group [*]=O 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• 125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
• 229960001412 pentobarbital Drugs 0.000 description 1
• KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
• 150000004965 peroxy acids Chemical class 0.000 description 1
• 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
• 239000008194 pharmaceutical composition Substances 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
• 229940067157 phenylhydrazine Drugs 0.000 description 1
• NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
• 239000008363 phosphate buffer Substances 0.000 description 1
• 150000003003 phosphines Chemical class 0.000 description 1
• 150000003016 phosphoric acids Chemical class 0.000 description 1
• 150000003018 phosphorus compounds Chemical class 0.000 description 1
• UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
• DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
• 229960001416 pilocarpine Drugs 0.000 description 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 238000003825 pressing Methods 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
• 125000005554 pyridyloxy group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 238000000197 pyrolysis Methods 0.000 description 1
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 230000002040 relaxant effect Effects 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 229910052703 rhodium Inorganic materials 0.000 description 1
• 239000010948 rhodium Substances 0.000 description 1
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 239000000523 sample Substances 0.000 description 1
• 239000012488 sample solution Substances 0.000 description 1
• 238000007790 scraping Methods 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000003333 secondary alcohols Chemical class 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 230000004622 sleep time Effects 0.000 description 1
• 210000002460 smooth muscle Anatomy 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
• 229960002218 sodium chlorite Drugs 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 229910001948 sodium oxide Inorganic materials 0.000 description 1
• VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
• UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
• ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 150000003463 sulfur Chemical class 0.000 description 1
• 125000004434 sulfur atom Chemical group 0.000 description 1
• 150000003464 sulfur compounds Chemical class 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
• SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical class CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
• 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
• 125000005505 thiomorpholino group Chemical group 0.000 description 1
• 150000003582 thiophosphoric acids Chemical class 0.000 description 1
• 239000010936 titanium Substances 0.000 description 1
• 229910052719 titanium Inorganic materials 0.000 description 1
• 239000004408 titanium dioxide Substances 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin Toxicity 0.000 description 1
• 108700012359 toxins Proteins 0.000 description 1
• 210000003437 trachea Anatomy 0.000 description 1
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 229910052723 transition metal Inorganic materials 0.000 description 1
• 150000003624 transition metals Chemical class 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical class CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
• PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
• ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
• PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical group FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 230000001960 triggered effect Effects 0.000 description 1
• 229910001930 tungsten oxide Inorganic materials 0.000 description 1
• 229910052720 vanadium Inorganic materials 0.000 description 1
• 229910001935 vanadium oxide Inorganic materials 0.000 description 1
• 239000002966 varnish Substances 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 150000003752 zinc compounds Chemical class 0.000 description 1