NO783529L - Nye derivater av tiazolin. - Google Patents
Nye derivater av tiazolin.Info
- Publication number
- NO783529L NO783529L NO783529A NO783529A NO783529L NO 783529 L NO783529 L NO 783529L NO 783529 A NO783529 A NO 783529A NO 783529 A NO783529 A NO 783529A NO 783529 L NO783529 L NO 783529L
- Authority
- NO
- Norway
- Prior art keywords
- pyridyl
- methyl
- thione
- denotes
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000012990 dithiocarbamate Substances 0.000 claims description 7
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003549 thiazolines Chemical class 0.000 claims description 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- 239000000243 solution Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 26
- 238000009835 boiling Methods 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000001914 filtration Methods 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000013078 crystal Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 15
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- WNQHHKFFJCEFRW-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)carbamodithioate;triethylazanium Chemical compound CC[NH+](CC)CC.CC1=CC=CC(NC([S-])=S)=N1 WNQHHKFFJCEFRW-UHFFFAOYSA-N 0.000 description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 8
- 238000006297 dehydration reaction Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical compound SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 description 3
- AALRHBLMAVGWRR-UHFFFAOYSA-N 1-chlorobutan-2-one Chemical compound CCC(=O)CCl AALRHBLMAVGWRR-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- QXFNOOZOSRTWLW-UHFFFAOYSA-N n-(6-propylpyridin-2-yl)carbamodithioate;triethylazanium Chemical compound CC[NH+](CC)CC.CCCC1=CC=CC(NC([S-])=S)=N1 QXFNOOZOSRTWLW-UHFFFAOYSA-N 0.000 description 3
- -1 paratoluenesulfonic acid monohydrate Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QVMRSFQXWJGXRL-UHFFFAOYSA-N 1-chloro-4-methylpentan-2-one Chemical compound CC(C)CC(=O)CCl QVMRSFQXWJGXRL-UHFFFAOYSA-N 0.000 description 2
- FVXNLWRKEVZHKO-UHFFFAOYSA-N 1-chlorohexan-2-one Chemical compound CCCCC(=O)CCl FVXNLWRKEVZHKO-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- ZXWAHROJUXWVCU-UHFFFAOYSA-N 2-chloro-1-cyclopropylethanone Chemical compound ClCC(=O)C1CC1 ZXWAHROJUXWVCU-UHFFFAOYSA-N 0.000 description 2
- FKAXLEKRJSNZCF-UHFFFAOYSA-N 3-(6-ethylpyridin-2-yl)-4-hydroxy-4-methyl-1,3-thiazolidine-2-thione Chemical compound CCC1=CC=CC(N2C(CSC2=S)(C)O)=N1 FKAXLEKRJSNZCF-UHFFFAOYSA-N 0.000 description 2
- KCPACMFMDRACBZ-UHFFFAOYSA-N 4-butyl-4-hydroxy-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CCCCC1(O)CSC(=S)N1C1=CC=CC(C)=N1 KCPACMFMDRACBZ-UHFFFAOYSA-N 0.000 description 2
- SYYBGRAWXXXMMP-UHFFFAOYSA-N 4-hydroxy-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC1=CC=CC(N2C(SCC2O)=S)=N1 SYYBGRAWXXXMMP-UHFFFAOYSA-N 0.000 description 2
- XFRCYBBVWOTDKN-UHFFFAOYSA-N 4-hydroxy-3-(6-methylpyridin-2-yl)-4-propyl-1,3-thiazolidine-2-thione Chemical compound CCCC1(O)CSC(=S)N1C1=CC=CC(C)=N1 XFRCYBBVWOTDKN-UHFFFAOYSA-N 0.000 description 2
- MJMMSGUOLKDZSW-UHFFFAOYSA-N 4-hydroxy-4-(methoxymethyl)-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound COCC1(O)CSC(=S)N1C1=CC=CC(C)=N1 MJMMSGUOLKDZSW-UHFFFAOYSA-N 0.000 description 2
- JMFDWHRKNVBBKX-UHFFFAOYSA-N 4-hydroxy-4-methyl-3-(4-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC1=CC=NC(N2C(CSC2=S)(C)O)=C1 JMFDWHRKNVBBKX-UHFFFAOYSA-N 0.000 description 2
- VAUSCBTVMZITDY-UHFFFAOYSA-N 4-hydroxy-4-methyl-3-(5-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound N1=CC(C)=CC=C1N1C(O)(C)CSC1=S VAUSCBTVMZITDY-UHFFFAOYSA-N 0.000 description 2
- XKDKCBVIKMTRDQ-UHFFFAOYSA-N 4-hydroxy-4-methyl-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC1=CC=CC(N2C(CSC2=S)(C)O)=N1 XKDKCBVIKMTRDQ-UHFFFAOYSA-N 0.000 description 2
- JXKAUUVMXZIJNZ-UHFFFAOYSA-N 6-ethylpyridin-2-amine Chemical compound CCC1=CC=CC(N)=N1 JXKAUUVMXZIJNZ-UHFFFAOYSA-N 0.000 description 2
- JDRTXRTVJTWITJ-UHFFFAOYSA-N 6-propylpyridin-2-amine Chemical compound CCCC1=CC=CC(N)=N1 JDRTXRTVJTWITJ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VFJVXXLZFLLCMV-UHFFFAOYSA-N n,n-diethylethanamine;(5-methylpyridin-2-yl)carbamodithioic acid Chemical compound CCN(CC)CC.CC1=CC=C(NC(S)=S)N=C1 VFJVXXLZFLLCMV-UHFFFAOYSA-N 0.000 description 2
- ZERJVEQLQZTTQS-UHFFFAOYSA-N n,n-diethylethanamine;pyridin-2-ylcarbamodithioic acid Chemical compound CCN(CC)CC.SC(=S)NC1=CC=CC=N1 ZERJVEQLQZTTQS-UHFFFAOYSA-N 0.000 description 2
- AFUDIRKIAWIJJT-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)carbamodithioate;triethylazanium Chemical compound CC[NH+](CC)CC.CC1=CC=NC(NC([S-])=S)=C1 AFUDIRKIAWIJJT-UHFFFAOYSA-N 0.000 description 2
- WACNUSGXNNCCDV-UHFFFAOYSA-N n-(6-ethylpyridin-2-yl)carbamodithioate;triethylazanium Chemical compound CC[NH+](CC)CC.CCC1=CC=CC(NC([S-])=S)=N1 WACNUSGXNNCCDV-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 150000003548 thiazolidines Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- JLCZWDGDDGMLHA-UHFFFAOYSA-N 1-chloro-3-methoxypropan-2-one Chemical compound COCC(=O)CCl JLCZWDGDDGMLHA-UHFFFAOYSA-N 0.000 description 1
- MGTGUEKJBFTQQW-UHFFFAOYSA-N 1-chloropentan-2-one Chemical compound CCCC(=O)CCl MGTGUEKJBFTQQW-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 description 1
- PWFFUVGOESAUPV-UHFFFAOYSA-N 3-pyridin-2-yl-1,3-thiazolidine-2-thione Chemical compound N1=C(C=CC=C1)N1C(SCC1)=S PWFFUVGOESAUPV-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OEPZZBQQOWWJIB-UHFFFAOYSA-N 4-ethyl-3-(6-ethylpyridin-2-yl)-4-hydroxy-1,3-thiazolidine-2-thione Chemical compound CCC1=CC=CC(N2C(CSC2=S)(O)CC)=N1 OEPZZBQQOWWJIB-UHFFFAOYSA-N 0.000 description 1
- CUXDFQARIWPQAP-UHFFFAOYSA-N 4-ethyl-4-hydroxy-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CCC1(O)CSC(=S)N1C1=CC=CC(C)=N1 CUXDFQARIWPQAP-UHFFFAOYSA-N 0.000 description 1
- PJZZQJBZVPODLJ-UHFFFAOYSA-N 4-hydroxy-4,5-dimethyl-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC1(O)C(C)SC(=S)N1C1=CC=CC(C)=N1 PJZZQJBZVPODLJ-UHFFFAOYSA-N 0.000 description 1
- XXWQFHCOPPVTTH-UHFFFAOYSA-N 4-hydroxy-4-(2-methylpropyl)-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC(C)CC1(O)CSC(=S)N1C1=CC=CC(C)=N1 XXWQFHCOPPVTTH-UHFFFAOYSA-N 0.000 description 1
- WTPRNYOTYMMEGB-UHFFFAOYSA-N 4-hydroxy-4-methyl-3-(6-propylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CCCC1=CC=CC(N2C(CSC2=S)(C)O)=N1 WTPRNYOTYMMEGB-UHFFFAOYSA-N 0.000 description 1
- 206010000087 Abdominal pain upper Diseases 0.000 description 1
- 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 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 231100000111 LD50 Toxicity 0.000 description 1
- 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 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7731431A FR2406637A1 (fr) | 1977-10-19 | 1977-10-19 | Nouveaux derives de la thiazoline, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR7826304A FR2436148A1 (fr) | 1978-09-13 | 1978-09-13 | Nouveaux derives de la thiazoline, leur preparation et les medicaments qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO783529L true NO783529L (no) | 1979-04-20 |
Family
ID=26220267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO783529A NO783529L (no) | 1977-10-19 | 1978-10-18 | Nye derivater av tiazolin. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4167571A (fr) |
| JP (1) | JPS5479285A (fr) |
| AT (1) | ATA750578A (fr) |
| AU (1) | AU4078678A (fr) |
| CA (1) | CA1098906A (fr) |
| CS (1) | CS203932B2 (fr) |
| DE (1) | DE2845624A1 (fr) |
| DK (1) | DK464378A (fr) |
| ES (1) | ES474350A1 (fr) |
| FI (1) | FI783184A (fr) |
| GB (1) | GB2006210A (fr) |
| GR (1) | GR64044B (fr) |
| HU (1) | HU175528B (fr) |
| IL (1) | IL55757A0 (fr) |
| IT (1) | IT1101658B (fr) |
| LU (1) | LU80389A1 (fr) |
| NL (1) | NL7810230A (fr) |
| NO (1) | NO783529L (fr) |
| NZ (1) | NZ188676A (fr) |
| PT (1) | PT68668A (fr) |
| SE (1) | SE7810864L (fr) |
| SU (1) | SU793398A3 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2464954A2 (fr) * | 1979-09-12 | 1981-03-20 | Rhone Poulenc Ind | Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent |
| NL9001162A (nl) * | 1990-05-18 | 1991-12-16 | Stamicarbon | Werkwijze ter bereiding van 2-n-acylaminopyridines en 2-aminopyridines uit 5-oxoalkaannitriloximmen alsmede deze 5-oxoalkaannitriloximmen, 2-n-acylaminopyridines en 2-aminopyridines. |
| CN102234271B (zh) * | 2010-04-21 | 2015-06-10 | 北京大学 | 芳杂(烷基)氨基二硫代甲酸酯类化合物、其制备方法和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3761485A (en) * | 1971-09-07 | 1973-09-25 | Parke Davis & Co | 3-(5-chloro-2-pyridyl)rhodanine and 3-(5-chloro-2-pyridyl)-5-(lower alkyl)rhodanines |
-
1978
- 1978-10-11 NL NL7810230A patent/NL7810230A/xx not_active Application Discontinuation
- 1978-10-17 GB GB7840801A patent/GB2006210A/en not_active Withdrawn
- 1978-10-17 JP JP12691678A patent/JPS5479285A/ja active Pending
- 1978-10-17 GR GR57454A patent/GR64044B/el unknown
- 1978-10-17 AU AU40786/78A patent/AU4078678A/en active Pending
- 1978-10-17 NZ NZ188676A patent/NZ188676A/xx unknown
- 1978-10-17 US US05/952,198 patent/US4167571A/en not_active Expired - Lifetime
- 1978-10-18 CA CA313,694A patent/CA1098906A/fr not_active Expired
- 1978-10-18 NO NO783529A patent/NO783529L/no unknown
- 1978-10-18 PT PT68668A patent/PT68668A/fr unknown
- 1978-10-18 SU SU782674199A patent/SU793398A3/ru active
- 1978-10-18 DK DK464378A patent/DK464378A/da unknown
- 1978-10-18 LU LU80389A patent/LU80389A1/fr unknown
- 1978-10-18 SE SE7810864A patent/SE7810864L/xx unknown
- 1978-10-18 IL IL7855757A patent/IL55757A0/xx unknown
- 1978-10-19 AT AT0750578A patent/ATA750578A/de not_active Application Discontinuation
- 1978-10-19 ES ES474350A patent/ES474350A1/es not_active Expired
- 1978-10-19 HU HU78RO996A patent/HU175528B/hu unknown
- 1978-10-19 IT IT28911/78A patent/IT1101658B/it active
- 1978-10-19 CS CS786806A patent/CS203932B2/cs unknown
- 1978-10-19 FI FI783184A patent/FI783184A/fi unknown
- 1978-10-19 DE DE19782845624 patent/DE2845624A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DK464378A (da) | 1979-04-20 |
| GR64044B (en) | 1980-01-19 |
| CS203932B2 (en) | 1981-03-31 |
| ES474350A1 (es) | 1979-04-16 |
| IT7828911A0 (it) | 1978-10-19 |
| DE2845624A1 (de) | 1979-04-26 |
| SU793398A3 (ru) | 1980-12-30 |
| FI783184A (fi) | 1979-04-20 |
| IL55757A0 (en) | 1978-12-17 |
| HU175528B (hu) | 1980-08-28 |
| JPS5479285A (en) | 1979-06-25 |
| US4167571A (en) | 1979-09-11 |
| SE7810864L (sv) | 1979-04-20 |
| AU4078678A (en) | 1980-04-24 |
| IT1101658B (it) | 1985-10-07 |
| CA1098906A (fr) | 1981-04-07 |
| NZ188676A (en) | 1980-10-24 |
| NL7810230A (nl) | 1979-04-23 |
| GB2006210A (en) | 1979-05-02 |
| PT68668A (fr) | 1978-11-01 |
| LU80389A1 (fr) | 1979-06-15 |
| ATA750578A (de) | 1981-07-15 |
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