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
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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
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230000028993 immune response Effects 0.000 description 1
230000016784 immunoglobulin production Effects 0.000 description 1
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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
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150000007530 organic bases Chemical class 0.000 description 1
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150000004967 organic peroxy acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
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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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (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)
Seasonings (AREA)
Fats And Perfumes (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 (el)
EP (1)	EP0140830B1 (el)
JP (1)	JPS60149581A (el)
AT (1)	ATE45878T1 (el)
AU (1)	AU577308B2 (el)
CA (1)	CA1247615A (el)
DD (1)	DD222025A5 (el)
DE (1)	DE3479564D1 (el)
DK (1)	DK416184A (el)
ES (1)	ES8802308A1 (el)
FI (1)	FI83780C (el)
GB (2)	GB8323293D0 (el)
GR (1)	GR80260B (el)
HU (1)	HUT36819A (el)
IL (1)	IL72776A (el)
NO (1)	NO843455L (el)
NZ (1)	NZ209395A (el)
PT (1)	PT79146B (el)
ZA (1)	ZA846786B (el)

Families Citing this family (9)

* 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
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
CA2262671A1 (en) *	1996-08-27	1998-03-05	Shionogi & Co., Ltd.	Chromene-3-carboxylate derivatives
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
AU2301099A (en) *	1998-02-18	1999-09-06	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
EP2283898A1 (en) *	2002-12-23	2011-02-16	4Sc Ag	Aromatic compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents

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
JPS5651470A (en) *	1979-09-13	1981-05-09	Wellcome Found	Flavan derivative
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 DE DE8484810424T patent/DE3479564D1/de not_active Expired
- 1984-08-27 AT AT84810424T patent/ATE45878T1/de active
- 1984-08-27 FI FI843364A patent/FI83780C/fi not_active IP Right Cessation
- 1984-08-27 EP EP84810424A patent/EP0140830B1/en not_active Expired
- 1984-08-27 IL IL72776A patent/IL72776A/xx unknown
- 1984-08-28 PT PT79146A patent/PT79146B/pt not_active IP Right Cessation
- 1984-08-29 DD DD84266736A patent/DD222025A5/de not_active IP Right Cessation
- 1984-08-29 GB GB08421778A patent/GB2145720B/en not_active Expired
- 1984-08-29 CA CA000462008A patent/CA1247615A/en not_active Expired
- 1984-08-30 AU AU32572/84A patent/AU577308B2/en not_active Ceased
- 1984-08-30 ZA ZA846786A patent/ZA846786B/xx unknown
- 1984-08-30 GR GR80260A patent/GR80260B/el unknown
- 1984-08-30 NZ NZ209395A patent/NZ209395A/en unknown
- 1984-08-30 NO NO843455A patent/NO843455L/no unknown
- 1984-08-30 HU HU843262A patent/HUT36819A/hu unknown
- 1984-08-30 DK DK416184A patent/DK416184A/da not_active Application Discontinuation
- 1984-08-31 ES ES535590A patent/ES8802308A1/es not_active Expired
- 1984-08-31 JP JP59180892A patent/JPS60149581A/ja active Pending

Also Published As

Publication number	Publication date
ES8802308A1 (es)	1988-05-01
ATE45878T1 (de)	1989-09-15
AU3257284A (en)	1986-09-11
DD222025A5 (de)	1985-05-08
DE3479564D1 (en)	1989-10-05
GB2145720A (en)	1985-04-03
IL72776A (en)	1991-01-31
GB2145720B (en)	1987-02-04
EP0140830B1 (en)	1989-08-30
ES535590A0 (es)	1988-05-01
CA1247615A (en)	1988-12-28
IL72776A0 (en)	1984-11-30
ZA846786B (en)	1985-04-24
EP0140830A2 (en)	1985-05-08
EP0140830A3 (en)	1986-01-08
PT79146B (en)	1986-11-14
JPS60149581A (ja)	1985-08-07
FI843364A (fi)	1985-03-01
FI83780B (fi)	1991-05-15
GB8421778D0 (en)	1984-10-03
GB8323293D0 (en)	1983-10-05
FI83780C (fi)	1991-08-26
AU577308B2 (en)	1988-09-22
NZ209395A (en)	1987-11-27
HUT36819A (en)	1985-10-28
DK416184D0 (da)	1984-08-30
GR80260B (en)	1985-01-02
US4665202A (en)	1987-05-12
FI843364A0 (fi)	1984-08-27
DK416184A (da)	1985-03-01
PT79146A (en)	1984-09-01

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