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

Fremgangsmaate til fremstilling av flaven eller tioflavenderivater

Info

Publication number: NO843455L
Authority: NO; Norway
Prior art keywords: substituted; formula; unsubstituted; phenyl; alkyl
Prior art date: 1983-08-31

Application number

NO843455A

Other languages

English (en)

Norwegian (no)

Inventor

Christian Gerard Rimbault

Philippe Marcel Narbel

Original Assignee

Zyma Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-08-31

Filing date

1984-08-30

Publication date

1985-03-01

1984-08-30 Application filed by Zyma Sa filed Critical Zyma Sa

1985-03-01 Publication of NO843455L publication Critical patent/NO843455L/no

Links

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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/64—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with oxygen atoms directly attached in position 8
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Gastroenterology & Hepatology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Paints Or Removers (AREA)
Saccharide Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pyrane Compounds (AREA)
Fats And Perfumes (AREA)
Seasonings (AREA)

NO843455A 1983-08-31 1984-08-30 Fremgangsmaate til fremstilling av flaven eller tioflavenderivater NO843455L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB838323293A GB8323293D0 (en)	1983-08-31	1983-08-31	Substituted flavene and thioflavene derivatives

Publications (1)

Publication Number	Publication Date
NO843455L true NO843455L (no)	1985-03-01

Family

ID=10548081

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO843455A NO843455L (no)	1983-08-31	1984-08-30	Fremgangsmaate til fremstilling av flaven eller tioflavenderivater

Country Status (19)

Country	Link
US (1)	US4665202A (de)
EP (1)	EP0140830B1 (de)
JP (1)	JPS60149581A (de)
AT (1)	ATE45878T1 (de)
AU (1)	AU577308B2 (de)
CA (1)	CA1247615A (de)
DD (1)	DD222025A5 (de)
DE (1)	DE3479564D1 (de)
DK (1)	DK416184A (de)
ES (1)	ES8802308A1 (de)
FI (1)	FI83780C (de)
GB (2)	GB8323293D0 (de)
GR (1)	GR80260B (de)
HU (1)	HUT36819A (de)
IL (1)	IL72776A (de)
NO (1)	NO843455L (de)
NZ (1)	NZ209395A (de)
PT (1)	PT79146B (de)
ZA (1)	ZA846786B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8323292D0 (en) *	1983-08-31	1983-10-05	Zyma Sa	Flavene and thioflavene derivatives
JPH0758454B2 (ja)	1987-07-14	1995-06-21	キヤノン株式会社	座標入力装置
GB8805628D0 (en) *	1988-03-09	1988-04-07	Erba Farmitalia	Hypolipidaemic imidazol-2-yl-derivatives of bicyclic compounds & process for their preparation
US5763470A (en) *	1995-06-07	1998-06-09	Sugen Inc.	Benzopyran compounds and methods for their use
KR100343832B1 (ko) *	1996-08-27	2002-07-20	시오노기세이야쿠가부시키가이샤	크로멘-3-카르복실산 유도체
US6077850A (en)	1997-04-21	2000-06-20	G.D. Searle & Co.	Substituted benzopyran analogs for the treatment of inflammation
US6034256A (en) *	1997-04-21	2000-03-07	G.D. Searle & Co.	Substituted benzopyran derivatives for the treatment of inflammation
WO1999042459A1 (en) *	1998-02-18	1999-08-26	Shionogi & Co., Ltd.	Process for producing optically active chromene derivative
AU2001261006A1 (en) *	2000-03-28	2001-10-08	Chugai Seiyaku Kabushiki Kaisha	Benzopyranes useful as tnf alpha inhibitors
PT1578741E (pt) *	2002-12-23	2011-10-17	4Sc Ag	Compostos aromáticos como agentes antiinflamatórios, imunoreguladores e antiproliferativos

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE357755C (de) *	1920-03-27	1922-08-31	Chemische Fabriken Vorm Weiler	Verfahren zur Herstellung von Kondensationsprodukten aus ª‡íñª‰-ungesaettigten Ketonen und Phenolen
DE1493976C3 (de) *	1964-01-18	1973-09-13	Merck Patent Gmbh, 6100 Darmstadt	Substituierte Flavandenvate sowie Verfahren zu ihrer Herstellung
US3567605A (en) *	1966-03-30	1971-03-02	Ralph S Becker	Photochemical process
US3796727A (en) *	1972-01-31	1974-03-12	Eastman Kodak Co	Synthesis of novel benzopyran compounds
DE3069830D1 (en) *	1979-09-13	1985-01-31	Wellcome Found	Benzopyran compounds, useful as chemotherapeutic agents
DE3300004A1 (de) *	1983-01-03	1984-07-12	Bayer Ag, 5090 Leverkusen	Substituierte 4-aminomethylenchromane bzw. -chromene, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
HU194214B (en) *	1983-02-15	1988-01-28	Alkaloida Vegyeszeti Gyar	Process for producing 7-alkoxy-2h-chromene derivatives and insecticide and nematocide compositions containing them as active components
US4557783A (en) *	1983-12-05	1985-12-10	Cincinnati Milacron Inc.	Composite tape laying machine and method

1983
- 1983-08-31 GB GB838323293A patent/GB8323293D0/en active Pending
1984
- 1984-08-24 US US06/644,006 patent/US4665202A/en not_active Expired - Fee Related
- 1984-08-27 EP EP84810424A patent/EP0140830B1/de not_active Expired
- 1984-08-27 DE DE8484810424T patent/DE3479564D1/de not_active Expired
- 1984-08-27 IL IL72776A patent/IL72776A/xx unknown
- 1984-08-27 AT AT84810424T patent/ATE45878T1/de active
- 1984-08-27 FI FI843364A patent/FI83780C/fi not_active IP Right Cessation
- 1984-08-28 PT PT79146A patent/PT79146B/pt not_active IP Right Cessation
- 1984-08-29 CA CA000462008A patent/CA1247615A/en not_active Expired
- 1984-08-29 GB GB08421778A patent/GB2145720B/en not_active Expired
- 1984-08-29 DD DD84266736A patent/DD222025A5/de not_active IP Right Cessation
- 1984-08-30 AU AU32572/84A patent/AU577308B2/en not_active Ceased
- 1984-08-30 HU HU843262A patent/HUT36819A/hu unknown
- 1984-08-30 NO NO843455A patent/NO843455L/no unknown
- 1984-08-30 GR GR80260A patent/GR80260B/el unknown
- 1984-08-30 DK DK416184A patent/DK416184A/da not_active Application Discontinuation
- 1984-08-30 ZA ZA846786A patent/ZA846786B/xx unknown
- 1984-08-30 NZ NZ209395A patent/NZ209395A/en unknown
- 1984-08-31 JP JP59180892A patent/JPS60149581A/ja active Pending
- 1984-08-31 ES ES535590A patent/ES8802308A1/es not_active Expired

Also Published As

Publication number	Publication date
ES535590A0 (es)	1988-05-01
CA1247615A (en)	1988-12-28
PT79146B (en)	1986-11-14
ZA846786B (en)	1985-04-24
ATE45878T1 (de)	1989-09-15
US4665202A (en)	1987-05-12
DK416184D0 (da)	1984-08-30
DK416184A (da)	1985-03-01
DE3479564D1 (en)	1989-10-05
AU3257284A (en)	1986-09-11
EP0140830A3 (en)	1986-01-08
DD222025A5 (de)	1985-05-08
FI843364A0 (fi)	1984-08-27
AU577308B2 (en)	1988-09-22
PT79146A (en)	1984-09-01
EP0140830A2 (de)	1985-05-08
FI843364A7 (fi)	1985-03-01
GB2145720A (en)	1985-04-03
FI83780C (fi)	1991-08-26
GR80260B (en)	1985-01-02
NZ209395A (en)	1987-11-27
IL72776A0 (en)	1984-11-30
JPS60149581A (ja)	1985-08-07
GB2145720B (en)	1987-02-04
ES8802308A1 (es)	1988-05-01
GB8323293D0 (en)	1983-10-05
IL72776A (en)	1991-01-31
GB8421778D0 (en)	1984-10-03
HUT36819A (en)	1985-10-28
FI83780B (fi)	1991-05-15
EP0140830B1 (de)	1989-08-30

Publication	Publication Date	Title
US7094807B2 (en)	2006-08-22	Substituted aryl thioureas and related compounds; inhibitors of viral replication
CA3191172A1 (en)	2022-03-10	Quinoline cgas antagonist compounds
TW200523247A (en)	2005-07-16	3-(4-benzyloxyphenyl) propanoic acid derivatives
CA2439604C (en)	2012-05-01	N-phenylarylsulfonamide compound, pharmaceutical composition comprising the compound as active ingredient, synthetic intermediate for the compound and process for its preparation
EP0140830B1 (de)	1989-08-30	Pharmazeutische Präparate enthaltend Flaven- oder Thioflaven-Derivate, deren Verwendung, Flavene und Thioflavene und Verfahren zu deren Herstellung
US6797712B2 (en)	2004-09-28	Substituted amino-furan-2-yl-acetic acid and amino-thien-2-yl-acetic acid derivatives and their use in the treatment of migraine and pain
US4818765A (en)	1989-04-04	1,3-dithiolan-2-ylidenes their 1-oxides, pharmaceutical compositions, and methods of use thereof
CA2809112A1 (en)	2012-03-08	Cyclic amide derivative
NO831950L (no)	1983-12-02	Farmasoeytiske preparater inneholdende (+)-cyanidan-3-ol-derivater, deres anvendelse, nye substituerte (+)-cyanidan-3-ol-derivater og fremgangsmaater til deres fremstilling
US4371542A (en)	1983-02-01	Hetero-imino-prostacyclins
US4797414A (en)	1989-01-10	Naphthothiophene derivatives and their use as respiratory enhancing agents
CA1251213A (en)	1989-03-14	Pharmaceutical preparations containing flavanone or thioflavanone derivatives, the use thereof, flavanones and thioflavanones, and processes for their manufacture
NO843454L (no)	1985-03-01	Fremgangsmaate til fremstilling av flavene- og tioflavenderivater
CN110903224A (zh)	2020-03-24	一种芳基磺酰胺类化合物、其制备方法、药物组合物及用途
IE903375A1 (en)	1991-04-10	Further novel alkanophenones