NO820881L - Fremgangsmaate til fremstilling av nye tiazolderivater. - Google Patents

Fremgangsmaate til fremstilling av nye tiazolderivater.

Info

Publication number: NO820881L
Authority: NO; Norway
Prior art keywords: hydroxy; formula; atoms; lower alkyl; unsubstituted
Prior art date: 1981-03-18

Application number

NO820881A

Other languages

English (en)

Norwegian (no)

Inventor

Pier Giorgio Ferrini

Richard Goeschke

Original Assignee

Ciba Geigy Ag

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.)

1981-03-18

Filing date

1982-03-17

Publication date

1982-09-20

1982-03-17 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1982-09-20 Publication of NO820881L publication Critical patent/NO820881L/no

Links

238000000034 method Methods 0.000 title claims abstract description 72
238000002360 preparation method Methods 0.000 title claims abstract description 25
-1 2,4,5-Trisubstituted thiazoles Chemical class 0.000 claims abstract description 295
150000001875 compounds Chemical class 0.000 claims abstract description 195
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 147
150000003839 salts Chemical group 0.000 claims abstract description 124
125000001931 aliphatic group Chemical group 0.000 claims abstract description 21
125000003118 aryl group Chemical group 0.000 claims abstract description 20
125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
241000534944 Thia Species 0.000 claims abstract description 6
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
125000000217 alkyl group Chemical group 0.000 claims description 199
125000004432 carbon atom Chemical group C* 0.000 claims description 110
229910052736 halogen Inorganic materials 0.000 claims description 62
125000004423 acyloxy group Chemical group 0.000 claims description 58
150000002367 halogens Chemical group 0.000 claims description 56
125000003545 alkoxy group Chemical group 0.000 claims description 51
238000006243 chemical reaction Methods 0.000 claims description 41
125000004043 oxo group Chemical group O=* 0.000 claims description 40
125000004414 alkyl thio group Chemical group 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 35
229910052740 iodine Inorganic materials 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
125000003396 thiol group Chemical group [H]S* 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 22
125000001072 heteroaryl group Chemical group 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
125000003342 alkenyl group Chemical group 0.000 claims description 15
125000005530 alkylenedioxy group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000001544 thienyl group Chemical group 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
230000015572 biosynthetic process Effects 0.000 claims description 9
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
229910052727 yttrium Inorganic materials 0.000 claims description 5
DYTHCBNAPSKPBL-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]sulfonyl]ethanol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(S(=O)(=O)CCO)=N1 DYTHCBNAPSKPBL-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
MKIGAHAWFJIWRS-UHFFFAOYSA-N 2-[(5-phenyl-4-pyridin-3-yl-1,3-thiazol-2-yl)sulfanyl]ethanol Chemical compound S1C(SCCO)=NC(C=2C=NC=CC=2)=C1C1=CC=CC=C1 MKIGAHAWFJIWRS-UHFFFAOYSA-N 0.000 claims description 2
NYVANPRRXGWPTH-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]sulfanyl]ethyl acetate Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(SCCOC(C)=O)=N1 NYVANPRRXGWPTH-UHFFFAOYSA-N 0.000 claims description 2
IGWHQJDTYMGGLI-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]sulfinyl]ethanol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(S(=O)CCO)=N1 IGWHQJDTYMGGLI-UHFFFAOYSA-N 0.000 claims description 2
ZWTBEDCTSGUSKC-UHFFFAOYSA-N 3-[[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]sulfanyl]propan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(SCCCO)=N1 ZWTBEDCTSGUSKC-UHFFFAOYSA-N 0.000 claims description 2
NWOPEUVLTNOTBD-UHFFFAOYSA-N 3-[[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]sulfinyl]propan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(S(=O)CCCO)=N1 NWOPEUVLTNOTBD-UHFFFAOYSA-N 0.000 claims description 2
125000003700 epoxy group Chemical class 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 39
208000025747 Rheumatic disease Diseases 0.000 abstract description 3
239000003435 antirheumatic agent Substances 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
229940079593 drug Drugs 0.000 abstract description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 2
238000001311 chemical methods and process Methods 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 119
235000002639 sodium chloride Nutrition 0.000 description 85
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 83
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 79
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 70
239000002253 acid Substances 0.000 description 67
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 57
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
238000003756 stirring Methods 0.000 description 52
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 43
230000002829 reductive effect Effects 0.000 description 36
125000002947 alkylene group Chemical group 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000002585 base Substances 0.000 description 29
229910052757 nitrogen Inorganic materials 0.000 description 29
229910052943 magnesium sulfate Inorganic materials 0.000 description 27
235000019341 magnesium sulphate Nutrition 0.000 description 27
239000003921 oil Substances 0.000 description 27
235000019198 oils Nutrition 0.000 description 26
238000010438 heat treatment Methods 0.000 description 24
229910052783 alkali metal Inorganic materials 0.000 description 23
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 23
239000012074 organic phase Substances 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
235000011054 acetic acid Nutrition 0.000 description 20
239000013543 active substance Substances 0.000 description 20
239000002184 metal Chemical class 0.000 description 20
229910052751 metal Inorganic materials 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
150000008064 anhydrides Chemical class 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
238000001816 cooling Methods 0.000 description 18
239000012043 crude product Substances 0.000 description 18
239000005457 ice water Substances 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
235000011121 sodium hydroxide Nutrition 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
150000001340 alkali metals Chemical class 0.000 description 17
239000007858 starting material Substances 0.000 description 17
239000000725 suspension Substances 0.000 description 17
239000000460 chlorine Substances 0.000 description 16
239000012442 inert solvent Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
150000007513 acids Chemical class 0.000 description 15
229910052801 chlorine Inorganic materials 0.000 description 15
150000002430 hydrocarbons Chemical group 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
229910052784 alkaline earth metal Inorganic materials 0.000 description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
238000007792 addition Methods 0.000 description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
229910052794 bromium Inorganic materials 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 13
239000011261 inert gas Substances 0.000 description 13
229920001223 polyethylene glycol Polymers 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
235000014113 dietary fatty acids Nutrition 0.000 description 12
239000000194 fatty acid Substances 0.000 description 12
229930195729 fatty acid Natural products 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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 11
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 description 11
238000002425 crystallisation Methods 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
239000012071 phase Substances 0.000 description 11
IXFLFCVSGSQTCA-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]sulfanyl]ethanol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(SCCO)=N1 IXFLFCVSGSQTCA-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
229920002472 Starch Polymers 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
239000002480 mineral oil Substances 0.000 description 10
235000010446 mineral oil Nutrition 0.000 description 10
239000000825 pharmaceutical preparation Substances 0.000 description 10
239000012312 sodium hydride Substances 0.000 description 10
229910000104 sodium hydride Inorganic materials 0.000 description 10
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
235000019698 starch Nutrition 0.000 description 10
239000003826 tablet Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
YSWQWEKWICOHJP-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-5h-1,3-thiazole-2-thione Chemical compound C1=CC(OC)=CC=C1C1C(C=2C=CC(OC)=CC=2)=NC(=S)S1 YSWQWEKWICOHJP-UHFFFAOYSA-N 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 9
239000003638 chemical reducing agent Substances 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
230000001590 oxidative effect Effects 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000008107 starch Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
239000002202 Polyethylene glycol Substances 0.000 description 8
150000001336 alkenes Chemical class 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
239000011737 fluorine Substances 0.000 description 8
229910052731 fluorine Inorganic materials 0.000 description 8
229910052500 inorganic mineral Inorganic materials 0.000 description 8
235000010755 mineral Nutrition 0.000 description 8
239000011707 mineral Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 7
238000009835 boiling Methods 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
238000009833 condensation Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000000454 talc Substances 0.000 description 7
229910052623 talc Inorganic materials 0.000 description 7
235000012222 talc Nutrition 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
150000001335 aliphatic alkanes Chemical class 0.000 description 6
150000003973 alkyl amines Chemical class 0.000 description 6
YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
239000011630 iodine Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
229910052987 metal hydride Inorganic materials 0.000 description 6
150000004681 metal hydrides Chemical class 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000007787 solid Substances 0.000 description 6
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
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 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
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 5
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 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
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 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
150000001342 alkaline earth metals Chemical class 0.000 description 5
125000001118 alkylidene group Chemical group 0.000 description 5
229910052782 aluminium Inorganic materials 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
150000002191 fatty alcohols Chemical class 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000008101 lactose Substances 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
239000000463 material Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
125000001477 organic nitrogen group Chemical group 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
235000010288 sodium nitrite Nutrition 0.000 description 5
239000000600 sorbitol Substances 0.000 description 5
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
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UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
OJYKLIHWOKKEOW-UHFFFAOYSA-N methyl 2-(4,5-diphenyl-1,3-thiazol-2-yl)acetate Chemical compound S1C(CC(=O)OC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OJYKLIHWOKKEOW-UHFFFAOYSA-N 0.000 description 1
XMYDFKKZPNBWSI-UHFFFAOYSA-N methyl 2-[(4,5-diphenyl-1,3-thiazol-2-yl)sulfanyl]acetate Chemical compound S1C(SCC(=O)OC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XMYDFKKZPNBWSI-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
MIHRVCSSMAGKNH-UHFFFAOYSA-M n-ethylcarbamodithioate Chemical compound CCNC([S-])=S MIHRVCSSMAGKNH-UHFFFAOYSA-M 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002895 organic esters Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 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
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical group ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
235000010263 potassium metabisulphite Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000001120 potassium sulphate Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
229940080236 sodium cetyl sulfate Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
KZLAYICWOGEOSV-UHFFFAOYSA-M sodium;2-sulfanylpropanoate Chemical compound [Na+].CC(S)C([O-])=O KZLAYICWOGEOSV-UHFFFAOYSA-M 0.000 description 1
RSASPWMZKNIURZ-UHFFFAOYSA-M sodium;2-thiophen-2-ylacetate Chemical compound [Na+].[O-]C(=O)CC1=CC=CS1 RSASPWMZKNIURZ-UHFFFAOYSA-M 0.000 description 1
KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
229940057429 sorbitan isostearate Drugs 0.000 description 1
229950004959 sorbitan oleate Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003455 sulfinic acids Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
150000003899 tartaric acid esters Chemical class 0.000 description 1
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 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
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003565 thiocarboxylic acid derivatives Chemical class 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
239000004408 titanium dioxide Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical group COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
FJKIXWOMBXYWOQ-UHFFFAOYSA-N vinyl ethyl ether Natural products CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO820881A 1981-03-18 1982-03-17 Fremgangsmaate til fremstilling av nye tiazolderivater. NO820881L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH183881		1981-03-18

Publications (1)

Publication Number	Publication Date
NO820881L true NO820881L (no)	1982-09-20

Family

ID=4219779

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO820881A NO820881L (no)	1981-03-18	1982-03-17	Fremgangsmaate til fremstilling av nye tiazolderivater.

Country Status (16)

Country	Link
US (1)	US4451471A (el)
EP (1)	EP0061425A3 (el)
JP (1)	JPS57183767A (el)
KR (1)	KR830009066A (el)
AU (1)	AU8166782A (el)
DK (1)	DK118482A (el)
ES (8)	ES8400102A1 (el)
FI (1)	FI820877L (el)
GB (1)	GB2098203B (el)
GR (1)	GR78347B (el)
HU (1)	HU187684B (el)
IL (1)	IL65285A (el)
NO (1)	NO820881L (el)
NZ (1)	NZ200038A (el)
PT (1)	PT74593B (el)
ZA (1)	ZA821790B (el)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4632930A (en) *	1984-11-30	1986-12-30	E. I. Du Pont De Nemours And Company	Antihypertensive alkyl-arylimidazole, thiazole and oxazole derivatives
DE3508666A1 (de) *	1985-03-12	1986-09-18	Hoechst Ag, 6230 Frankfurt	Heterocyclische disulfide und ihre anwendung als immunmodulatoren
DE3508665A1 (de) *	1985-03-12	1986-09-18	Hoechst Ag, 6230 Frankfurt	Heterocyclische sulfide und ihre anwendung als immunmodulatoren
JPS6339868A (ja) *	1986-08-04	1988-02-20	Otsuka Pharmaceut Factory Inc	ジ低級アルキルフエノ−ル誘導体
EP0301613B1 (en) *	1987-07-27	1991-07-10	Duphar International Research B.V	Thiazole compounds having fungicidal activity
AT392788B (de) *	1988-02-03	1991-06-10	Fisons Plc	Neue benzimidazolverbindungen, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen
DE3807232A1 (de) *	1988-03-05	1989-09-14	Bayer Ag	Substituierte acrylsaeureester
JP2933739B2 (ja) *	1990-04-09	1999-08-16	明治製菓株式会社	チアゾールまたはイミダゾール誘導体および抗潰瘍剤
US5255697A (en) *	1991-10-23	1993-10-26	Working Inc.	Walking support apparatus
JP2636819B2 (ja)	1994-12-20	1997-07-30	日本たばこ産業株式会社	オキサゾール系複素環式芳香族化合物
CA2381215A1 (en) *	1999-08-06	2001-02-15	Takeda Chemical Industries, Ltd.	P38map kinase inhibitors
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1982
- 1982-03-08 US US06/355,989 patent/US4451471A/en not_active Expired - Fee Related
- 1982-03-12 EP EP82810111A patent/EP0061425A3/de not_active Withdrawn
- 1982-03-15 FI FI820877A patent/FI820877L/fi not_active Application Discontinuation
- 1982-03-17 ES ES510504A patent/ES8400102A1/es not_active Expired
- 1982-03-17 HU HU82811A patent/HU187684B/hu unknown
- 1982-03-17 NZ NZ200038A patent/NZ200038A/en unknown
- 1982-03-17 GB GB8207759A patent/GB2098203B/en not_active Expired
- 1982-03-17 NO NO820881A patent/NO820881L/no unknown
- 1982-03-17 ZA ZA821790A patent/ZA821790B/xx unknown
- 1982-03-17 PT PT74593A patent/PT74593B/pt unknown
- 1982-03-17 DK DK118482A patent/DK118482A/da not_active Application Discontinuation
- 1982-03-18 IL IL65285A patent/IL65285A/xx unknown
- 1982-03-18 AU AU81667/82A patent/AU8166782A/en not_active Abandoned
- 1982-03-18 KR KR1019820001200A patent/KR830009066A/ko unknown
- 1982-03-18 JP JP57041809A patent/JPS57183767A/ja active Pending
1983
- 1983-05-30 GR GR67611A patent/GR78347B/el unknown
- 1983-05-31 ES ES522868A patent/ES8502980A1/es not_active Expired
- 1983-05-31 ES ES522867A patent/ES522867A0/es active Granted
- 1983-05-31 ES ES522869A patent/ES522869A0/es active Granted
1984
- 1984-10-31 ES ES537278A patent/ES537278A0/es active Granted
- 1984-10-31 ES ES537277A patent/ES537277A0/es active Granted
- 1984-11-02 ES ES537342A patent/ES8604180A1/es not_active Expired
- 1984-11-02 ES ES537343A patent/ES537343A0/es active Granted

Also Published As

Publication number	Publication date
HU187684B (en)	1986-02-28
PT74593A (de)	1982-04-01
ES510504A0 (es)	1983-10-16
ZA821790B (en)	1983-01-26
AU8166782A (en)	1982-09-23
ES8601171A1 (es)	1985-10-16
ES522868A0 (es)	1985-02-01
ES537342A0 (es)	1986-01-16
ES8603847A1 (es)	1986-01-01
IL65285A (en)	1985-11-29
EP0061425A2 (de)	1982-09-29
ES8503677A1 (es)	1985-03-16
GB2098203A (en)	1982-11-17
GR78347B (el)	1984-09-26
ES8603499A1 (es)	1985-12-16
ES537278A0 (es)	1985-12-16
NZ200038A (en)	1985-05-31
IL65285A0 (en)	1982-05-31
ES8604180A1 (es)	1986-01-16
GB2098203B (en)	1985-05-09
KR830009066A (ko)	1983-12-17
EP0061425A3 (de)	1982-12-15
DK118482A (da)	1982-09-19
ES522869A0 (es)	1985-03-16
ES537343A0 (es)	1985-10-16
US4451471A (en)	1984-05-29
ES537277A0 (es)	1986-01-01
PT74593B (de)	1984-11-27
ES8400102A1 (es)	1983-10-16
JPS57183767A (en)	1982-11-12
ES8502980A1 (es)	1985-02-01
FI820877L (fi)	1982-09-19
ES8603498A1 (es)	1985-12-16
ES522867A0 (es)	1985-12-16

Publication	Publication Date	Title
NO820881L (no)	1982-09-20	Fremgangsmaate til fremstilling av nye tiazolderivater.
SI9111647A (en)	1997-12-31	Unsaturated hydroxyalkylquinoline acids
US4302461A (en)	1981-11-24	Antiinflammatory 5-substituted-2,3-diarylthiophenes
JP2014513074A (ja)	2014-05-29	ウィルス複製の阻害剤、それらの調製方法及びそれらの治療的使用
IE46454B1 (en)	1983-06-15	Anti-inflamatory 1-substituted-4,5-diaryl-2-(substituted thio) imidazoles and their corresponding sulfoxides and sulfones
NO810064L (no)	1981-07-13	Fremgangsmaate for fremstilling av fysiologisk aktive pyrimidin-2-sulfider og s-oksyder derav
KR910002824B1 (ko)	1991-05-06	피리딘유도체 및 그것을 함유하는 궤양치료제
EP0295049B1 (en)	1991-10-09	Thiophene sulfonamide antiglaucoma agents
NO168355B (no)	1991-11-04	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzimidazolderivater
KR820002315B1 (ko)	1982-12-17	메르캅토이미다졸 유도체의 제조방법
NO171412B (no)	1992-11-30	Analogifremgangsmaate for fremstilling av terapeutisk aktive 1,3-oksatiolan- eller 1,3-ditiolanderivater
US4654358A (en)	1987-03-31	1,4,5-triphenylimidazol-2-yl mercapto alkanoic acids, useful against inflammation and diseases responding to lipid lowering
US4159338A (en)	1979-06-26	Antiinflammatory-4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulfoxides and sulfones
IE55484B1 (en)	1990-09-26	Dithio compounds,pharmaceutical preparations containing them and their use
US4355034A (en)	1982-10-19	Ethenyl derivatives of mercaptoalkylpyridines as anti-inflammatory agents
US5102905A (en)	1992-04-07	Thienyl benzothienyl and dibenzothienyl compounds as inhibitors of aldose reductase
GB2061928A (en)	1981-05-20	Anti-inflammatory and immunoregulatory pyridines and pyrimidines
CA1105024A (en)	1981-07-14	Anti-inflammatory-4,5-dicyclic-2-(substituted thio) imidazoles and their corresponding sulfoxides and sulfones
EP0150461A2 (de)	1985-08-07	Schwefelhaltige 6-Ketoprostaglandine
KR960012367B1 (ko)	1996-09-20	2-알킬설피닐-4(3h)-퀴나졸리논 유도체, 이의 제조방법 및 약제학적 조성물
DD202705A5 (de)	1983-09-28	Verfahren zur herstellung neuer thiazolderivate
NO851035L (no)	1985-09-17	Fremgangsmaate til fremstilling av nye 1,2,4-triazacykloalkaderivater
US4193928A (en)	1980-03-18	Lasalocid derivatives
NO812790L (no)	1982-02-22	Nye diaryl-imidazol-forbindelser, fremgangsmaate til deres fremstilling, farmasoeytiske preparater som inneholder disse og deres anvendelse
CZ281857B6 (cs)	1997-03-12	3,4-Dihydro-2-alkyl-3-oxo-N-aryl-2H-[1]benzothieno[3,2-e]-1,2-thiazin-4-karboxamid-1,1-dioxidy, způsob jejich přípravy, meziprodukty tohoto způsobu, farmaceutický prostředek a použití