JPH0120155B2 - - Google Patents
Info
- Publication number
- JPH0120155B2 JPH0120155B2 JP55105839A JP10583980A JPH0120155B2 JP H0120155 B2 JPH0120155 B2 JP H0120155B2 JP 55105839 A JP55105839 A JP 55105839A JP 10583980 A JP10583980 A JP 10583980A JP H0120155 B2 JPH0120155 B2 JP H0120155B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- carbon atoms
- methyl
- benzo
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 54
- -1 di-substituted phenyl Chemical group 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 239000001257 hydrogen Substances 0.000 claims abstract description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 239000000460 chlorine Chemical group 0.000 claims abstract description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 23
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 239000011593 sulfur Substances 0.000 claims abstract description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 134
- 239000003208 petroleum Substances 0.000 claims description 63
- AUOZZCPDJUVSKZ-BMRADRMJSA-N (2e)-2-[ethylamino(phenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/NCC)C1=CC=CC=C1 AUOZZCPDJUVSKZ-BMRADRMJSA-N 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 230000009467 reduction Effects 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 10
- 239000011707 mineral Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000005521 carbonamide group Chemical group 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 239000000010 aprotic solvent Substances 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 7
- VPRSNYUHGGSGEP-JQIJEIRASA-N (2e)-2-[methylamino(phenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/NC)C1=CC=CC=C1 VPRSNYUHGGSGEP-JQIJEIRASA-N 0.000 claims description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 claims description 6
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003586 protic polar solvent Substances 0.000 claims description 6
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002084 enol ethers Chemical class 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 235000014413 iron hydroxide Nutrition 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
- AKGNUCMHPSRQHL-BMRADRMJSA-N (2e)-2-[dimethylamino(phenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(N(C)C)\C1=CC=CC=C1 AKGNUCMHPSRQHL-BMRADRMJSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 3
- BXUJLDCZHRIZDH-HTXNQAPBSA-N (2e)-2-[[2-(dimethylamino)ethylamino]-phenylmethylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/NCCN(C)C)C1=CC=CC=C1 BXUJLDCZHRIZDH-HTXNQAPBSA-N 0.000 claims description 2
- OHUOHBAWAAPIDL-UHFFFAOYSA-N 2-(benzenecarboximidoyl)-1-benzothiophen-3-ol Chemical compound Oc1c(sc2ccccc12)C(=N)c1ccccc1 OHUOHBAWAAPIDL-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 229940124575 antispasmodic agent Drugs 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 222
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 118
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- 239000000047 product Substances 0.000 description 50
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 230000007935 neutral effect Effects 0.000 description 23
- 239000013078 crystal Substances 0.000 description 22
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- ALJWLHQGTSSBHL-UHFFFAOYSA-N (3-hydroxy-1-benzothiophen-2-yl)-phenylmethanone Chemical compound S1C2=CC=CC=C2C(O)=C1C(=O)C1=CC=CC=C1 ALJWLHQGTSSBHL-UHFFFAOYSA-N 0.000 description 18
- 229910021529 ammonia Inorganic materials 0.000 description 18
- XIJTZTNNGQLXAT-FYWRMAATSA-N (2e)-2-[amino(phenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/N)C1=CC=CC=C1 XIJTZTNNGQLXAT-FYWRMAATSA-N 0.000 description 17
- 238000000921 elemental analysis Methods 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 16
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 15
- 239000005695 Ammonium acetate Substances 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 235000019257 ammonium acetate Nutrition 0.000 description 15
- 229940043376 ammonium acetate Drugs 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 238000004809 thin layer chromatography Methods 0.000 description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 208000005392 Spasm Diseases 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002211 ultraviolet spectrum Methods 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 4
- 230000001256 tonic effect Effects 0.000 description 4
- KAIJJEDETYMCDH-UHFFFAOYSA-N (2-bromophenyl)-(3-hydroxy-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC=CC=C2C(O)=C1C(=O)C1=CC=CC=C1Br KAIJJEDETYMCDH-UHFFFAOYSA-N 0.000 description 3
- BKGKRTZLULFYCE-UHFFFAOYSA-N (2-ethylphenyl)-(3-hydroxy-1-benzothiophen-2-yl)methanone Chemical compound CCC1=CC=CC=C1C(=O)C1=C(O)C2=CC=CC=C2S1 BKGKRTZLULFYCE-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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- SQAGJEATLHOHRV-FYWRMAATSA-N (2e)-2-[amino-(2-nitrophenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/N)C1=CC=CC=C1[N+]([O-])=O SQAGJEATLHOHRV-FYWRMAATSA-N 0.000 description 1
- WJECSBXPYOSGRW-FBMGVBCBSA-N (2e)-2-[amino-(2-propylphenyl)methylidene]-1-benzothiophen-3-one Chemical compound CCCC1=CC=CC=C1\C(N)=C/1C(=O)C2=CC=CC=C2S\1 WJECSBXPYOSGRW-FBMGVBCBSA-N 0.000 description 1
- GMMIJOYUOHLNIK-JQIJEIRASA-N (2e)-2-[amino-(3-methylphenyl)methylidene]-1-benzothiophen-3-one Chemical compound CC1=CC=CC(C(\N)=C/2C(C3=CC=CC=C3S\2)=O)=C1 GMMIJOYUOHLNIK-JQIJEIRASA-N 0.000 description 1
- YCSIOQUKGXAHDU-FYWRMAATSA-N (2e)-2-[amino-(4-chlorophenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/N)C1=CC=C(Cl)C=C1 YCSIOQUKGXAHDU-FYWRMAATSA-N 0.000 description 1
- SYIUEIVCDZJUHK-JQIJEIRASA-N (2e)-2-[amino-(4-methylphenyl)methylidene]-1-benzothiophen-3-one Chemical compound C1=CC(C)=CC=C1C(\N)=C/1C(=O)C2=CC=CC=C2S\1 SYIUEIVCDZJUHK-JQIJEIRASA-N 0.000 description 1
- LLCUADMBKKSDST-FYWRMAATSA-N (2e)-2-[amino-[2-(trifluoromethyl)phenyl]methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/N)C1=CC=CC=C1C(F)(F)F LLCUADMBKKSDST-FYWRMAATSA-N 0.000 description 1
- HJRFBSUUEULKGZ-HTXNQAPBSA-N (2e)-2-[butylamino(phenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/NCCCC)C1=CC=CC=C1 HJRFBSUUEULKGZ-HTXNQAPBSA-N 0.000 description 1
- JWEIDXOCOLFGDC-HTXNQAPBSA-N (2e)-2-[ethylamino-(2-ethylphenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/NCC)C1=CC=CC=C1CC JWEIDXOCOLFGDC-HTXNQAPBSA-N 0.000 description 1
- IQABVXKBYDGVFJ-FOCLMDBBSA-N (2e)-2-[methoxy(phenyl)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/OC)C1=CC=CC=C1 IQABVXKBYDGVFJ-FOCLMDBBSA-N 0.000 description 1
- UHPOTAURWLLXHW-XUTLUUPISA-N (2e)-2-[phenyl-(2-phenylhydrazinyl)methylidene]-1-benzothiophen-3-one Chemical compound S1C2=CC=CC=C2C(=O)\C1=C(C=1C=CC=CC=1)/NNC1=CC=CC=C1 UHPOTAURWLLXHW-XUTLUUPISA-N 0.000 description 1
- KHRQXTHEVPEZEX-LSDHQDQOSA-N (2e)-2-[phenyl-(2-piperidin-1-ylethylamino)methylidene]-1-benzothiophen-3-one Chemical compound S1C2=CC=CC=C2C(=O)\C1=C(C=1C=CC=CC=1)/NCCN1CCCCC1 KHRQXTHEVPEZEX-LSDHQDQOSA-N 0.000 description 1
- XYJRRQXQUAAZAW-XUTLUUPISA-N (2e)-2-[phenyl-(2-pyrrolidin-1-ylethylamino)methylidene]-1-benzothiophen-3-one Chemical compound S1C2=CC=CC=C2C(=O)\C1=C(C=1C=CC=CC=1)/NCCN1CCCC1 XYJRRQXQUAAZAW-XUTLUUPISA-N 0.000 description 1
- GEAPSUYHAKXGAS-FBMGVBCBSA-N (2e)-2-[phenyl-(propan-2-ylamino)methylidene]-1-benzothiophen-3-one Chemical compound S/1C2=CC=CC=C2C(=O)C\1=C(/NC(C)C)C1=CC=CC=C1 GEAPSUYHAKXGAS-FBMGVBCBSA-N 0.000 description 1
- ATOKOVGMLALELU-UHFFFAOYSA-N (3-chloro-1-benzothiophen-2-yl)-phenylmethanone Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)C1=CC=CC=C1 ATOKOVGMLALELU-UHFFFAOYSA-N 0.000 description 1
- JOBVYQBAZDROPP-UHFFFAOYSA-N (4-fluorophenyl)-(3-hydroxy-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC=CC=C2C(O)=C1C(=O)C1=CC=C(F)C=C1 JOBVYQBAZDROPP-UHFFFAOYSA-N 0.000 description 1
- GZIOMAIHGKUXRM-UHFFFAOYSA-N (5-chloro-3-hydroxy-1-benzothiophen-2-yl)-(2-chlorophenyl)methanone Chemical compound S1C2=CC=C(Cl)C=C2C(O)=C1C(=O)C1=CC=CC=C1Cl GZIOMAIHGKUXRM-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- JMIZDRYTNHYSQS-UHFFFAOYSA-N 2-benzoyl-1-benzothiophen-3-one Chemical compound S1C2=CC=CC=C2C(=O)C1C(=O)C1=CC=CC=C1 JMIZDRYTNHYSQS-UHFFFAOYSA-N 0.000 description 1
- NXYZFJSEESJRDW-UHFFFAOYSA-N 2-methylpropylazanium;acetate Chemical compound CC([O-])=O.CC(C)C[NH3+] NXYZFJSEESJRDW-UHFFFAOYSA-N 0.000 description 1
- MRKVTGSUIHJUQD-UHFFFAOYSA-N 3,4,5,7,8,9-hexahydro-2h-1,2-benzodiazepine Chemical compound C1CCNN=C2CCCC=C21 MRKVTGSUIHJUQD-UHFFFAOYSA-N 0.000 description 1
- VURMGNDSRHGHQN-UHFFFAOYSA-N 3-chloro-1-benzothiophene Chemical compound C1=CC=C2C(Cl)=CSC2=C1 VURMGNDSRHGHQN-UHFFFAOYSA-N 0.000 description 1
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241001481789 Rupicapra Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- SVBXPEXMMWJPIE-UHFFFAOYSA-N acetic acid;propan-1-amine Chemical compound CCC[NH3+].CC([O-])=O SVBXPEXMMWJPIE-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- XJMWHXZUIGHOBA-UHFFFAOYSA-N azane;propanoic acid Chemical compound N.CCC(O)=O XJMWHXZUIGHOBA-UHFFFAOYSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- LXTKCTMGEWVPTB-UHFFFAOYSA-N butylazanium;acetate Chemical compound CC(O)=O.CCCCN LXTKCTMGEWVPTB-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- KLOIYEQEVSIOOO-UHFFFAOYSA-N carbocromen Chemical compound CC1=C(CCN(CC)CC)C(=O)OC2=CC(OCC(=O)OCC)=CC=C21 KLOIYEQEVSIOOO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- IKXNIQJDNKPPCH-UHFFFAOYSA-N hydron;prop-2-yn-1-amine;chloride Chemical compound [Cl-].[NH3+]CC#C IKXNIQJDNKPPCH-UHFFFAOYSA-N 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- ZKONTOQLRAPWED-UHFFFAOYSA-N n-ethylmorpholin-4-amine Chemical compound CCNN1CCOCC1 ZKONTOQLRAPWED-UHFFFAOYSA-N 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- UXWLBSIELRUMEM-UHFFFAOYSA-L sodium hydrosulfite dihydrate Chemical compound O.O.[Na+].[Na+].[O-]S(=O)S([O-])=O UXWLBSIELRUMEM-UHFFFAOYSA-L 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RVUXIPACAZKWHU-UHFFFAOYSA-N sulfuric acid;heptahydrate Chemical compound O.O.O.O.O.O.O.OS(O)(=O)=O RVUXIPACAZKWHU-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/64—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Pens And Brushes (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Furan Compounds (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792931010 DE2931010A1 (de) | 1979-07-31 | 1979-07-31 | Neue vinyloge carboxamide, diese enthaltende arzneimittel und verfahren zur herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5622778A JPS5622778A (en) | 1981-03-03 |
| JPH0120155B2 true JPH0120155B2 (en]) | 1989-04-14 |
Family
ID=6077239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10583980A Granted JPS5622778A (en) | 1979-07-31 | 1980-07-31 | Carbonic amidovinylog |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4288437A (en]) |
| EP (1) | EP0025489B1 (en]) |
| JP (1) | JPS5622778A (en]) |
| AT (1) | ATE4210T1 (en]) |
| AU (1) | AU538685B2 (en]) |
| DE (2) | DE2931010A1 (en]) |
| DK (1) | DK151962C (en]) |
| ES (5) | ES8106901A1 (en]) |
| FI (1) | FI71140C (en]) |
| HK (1) | HK50685A (en]) |
| IE (1) | IE50076B1 (en]) |
| IL (1) | IL60708A (en]) |
| NO (1) | NO151501C (en]) |
| SG (1) | SG385G (en]) |
| ZA (1) | ZA804643B (en]) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3212752A1 (de) * | 1982-04-06 | 1983-10-13 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue vinyloge carboxamide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| JP2002525295A (ja) * | 1998-09-25 | 2002-08-13 | バイロファーマ・インコーポレイテッド | ウイルス感染および関連疾患の治療または予防法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2356824A (en) * | 1941-05-01 | 1944-08-29 | Du Pont | Organic dyestuffs of the thionaphthenone series, and process of making the same |
| DE2258036A1 (de) * | 1972-11-27 | 1974-05-30 | Goedecke Ag | Verfahren zur herstellung von benzo eckige klammer auf b eckige klammer zu thiophen-derivaten |
| LU76757A1 (en]) * | 1977-02-11 | 1978-10-18 |
-
1979
- 1979-07-31 DE DE19792931010 patent/DE2931010A1/de not_active Withdrawn
-
1980
- 1980-07-16 AT AT80104136T patent/ATE4210T1/de not_active IP Right Cessation
- 1980-07-16 DE DE8080104136T patent/DE3064255D1/de not_active Expired
- 1980-07-16 EP EP80104136A patent/EP0025489B1/de not_active Expired
- 1980-07-28 US US06/173,173 patent/US4288437A/en not_active Expired - Lifetime
- 1980-07-29 DK DK326180A patent/DK151962C/da not_active IP Right Cessation
- 1980-07-29 FI FI802366A patent/FI71140C/fi not_active IP Right Cessation
- 1980-07-30 ES ES493852A patent/ES8106901A1/es not_active Expired
- 1980-07-30 NO NO802292A patent/NO151501C/no unknown
- 1980-07-30 AU AU60930/80A patent/AU538685B2/en not_active Ceased
- 1980-07-30 IL IL60708A patent/IL60708A/xx unknown
- 1980-07-30 IE IE1596/80A patent/IE50076B1/en not_active IP Right Cessation
- 1980-07-31 JP JP10583980A patent/JPS5622778A/ja active Granted
- 1980-07-31 ZA ZA00804643A patent/ZA804643B/xx unknown
-
1981
- 1981-05-08 ES ES502015A patent/ES8202814A1/es not_active Expired
- 1981-05-08 ES ES502014A patent/ES502014A0/es active Granted
- 1981-05-08 ES ES502016A patent/ES502016A0/es active Granted
- 1981-05-08 ES ES502013A patent/ES8202812A1/es not_active Expired
-
1985
- 1985-01-03 SG SG3/85A patent/SG385G/en unknown
- 1985-07-04 HK HK506/85A patent/HK50685A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI71140B (fi) | 1986-08-14 |
| DK326180A (da) | 1981-02-01 |
| IE801596L (en) | 1981-01-31 |
| ATE4210T1 (de) | 1983-08-15 |
| EP0025489A1 (de) | 1981-03-25 |
| IL60708A (en) | 1984-05-31 |
| ZA804643B (en) | 1982-04-28 |
| ES8202815A1 (es) | 1982-03-01 |
| FI802366A7 (fi) | 1981-02-01 |
| NO802292L (no) | 1981-02-02 |
| HK50685A (en) | 1985-07-12 |
| JPS5622778A (en) | 1981-03-03 |
| ES502016A0 (es) | 1982-03-01 |
| AU6093080A (en) | 1981-02-05 |
| NO151501C (no) | 1985-04-24 |
| ES502015A0 (es) | 1982-03-01 |
| ES493852A0 (es) | 1981-09-01 |
| FI71140C (fi) | 1986-11-24 |
| AU538685B2 (en) | 1984-08-23 |
| US4288437A (en) | 1981-09-08 |
| SG385G (en) | 1985-11-15 |
| ES8202813A1 (es) | 1982-03-01 |
| DE3064255D1 (en) | 1983-08-25 |
| ES502013A0 (es) | 1982-03-01 |
| EP0025489B1 (de) | 1983-07-20 |
| ES8202812A1 (es) | 1982-03-01 |
| ES8106901A1 (es) | 1981-09-01 |
| IE50076B1 (en) | 1986-02-05 |
| DK151962C (da) | 1988-06-20 |
| DK151962B (da) | 1988-01-18 |
| ES502014A0 (es) | 1982-03-01 |
| NO151501B (no) | 1985-01-07 |
| DE2931010A1 (de) | 1981-02-26 |
| ES8202814A1 (es) | 1982-03-01 |
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