NO810962L - Fremgangsmaate for fremstilling av nye derivater av tioformamid - Google Patents
Fremgangsmaate for fremstilling av nye derivater av tioformamidInfo
- Publication number
- NO810962L NO810962L NO810962A NO810962A NO810962L NO 810962 L NO810962 L NO 810962L NO 810962 A NO810962 A NO 810962A NO 810962 A NO810962 A NO 810962A NO 810962 L NO810962 L NO 810962L
- Authority
- NO
- Norway
- Prior art keywords
- mixture
- solution
- minutes
- pyridyl
- kpa
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical class NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims abstract description 3
- -1 pyradaziriyl Chemical group 0.000 claims description 37
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000004434 sulfur atom Chemical group 0.000 claims description 22
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 4
- 239000012988 Dithioester Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000005022 dithioester group Chemical group 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 150000002900 organolithium compounds Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 5
- 229910052760 oxygen Chemical group 0.000 abstract 5
- 239000001301 oxygen Chemical group 0.000 abstract 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 206010061459 Gastrointestinal ulcer Diseases 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 240
- 239000000243 solution Substances 0.000 description 147
- 239000000203 mixture Substances 0.000 description 144
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 133
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 120
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
- 239000000047 product Substances 0.000 description 68
- 239000011541 reaction mixture Substances 0.000 description 68
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 239000012153 distilled water Substances 0.000 description 60
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 46
- 238000001914 filtration Methods 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
- 239000013078 crystal Substances 0.000 description 42
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 238000009835 boiling Methods 0.000 description 40
- 239000000741 silica gel Substances 0.000 description 40
- 229910002027 silica gel Inorganic materials 0.000 description 40
- 238000003756 stirring Methods 0.000 description 39
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 25
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
- 239000000284 extract Substances 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 23
- 230000007935 neutral effect Effects 0.000 description 23
- 239000003610 charcoal Substances 0.000 description 19
- 238000004809 thin layer chromatography Methods 0.000 description 18
- 239000003480 eluent Substances 0.000 description 17
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 17
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 16
- 239000012071 phase Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- 238000010908 decantation Methods 0.000 description 13
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical compound OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 5
- 238000010533 azeotropic distillation Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- MALGGXTXHGZMFY-UHFFFAOYSA-N 2-(3-chloropropylsulfanylmethyl)pyrazine Chemical compound ClCCCSCC1=CN=CC=N1 MALGGXTXHGZMFY-UHFFFAOYSA-N 0.000 description 3
- SPOJMJGNESDJGJ-UHFFFAOYSA-N 2-(4-chlorobutylsulfanylmethyl)pyridine Chemical compound ClCCCCSCC1=CC=CC=N1 SPOJMJGNESDJGJ-UHFFFAOYSA-N 0.000 description 3
- FEBPLMHEMNDSAH-UHFFFAOYSA-N 2-(oxolan-2-yl)pyridine Chemical compound C1CCOC1C1=CC=CC=N1 FEBPLMHEMNDSAH-UHFFFAOYSA-N 0.000 description 3
- SMTXCNOUCDVZKH-UHFFFAOYSA-N 2-(thiolan-2-yl)pyrazine Chemical compound C1CCSC1C1=CN=CC=N1 SMTXCNOUCDVZKH-UHFFFAOYSA-N 0.000 description 3
- SUVWAWWLOGXICM-UHFFFAOYSA-N 2-(thiolan-2-yl)quinoline Chemical compound C1CCSC1C1=CC=C(C=CC=C2)C2=N1 SUVWAWWLOGXICM-UHFFFAOYSA-N 0.000 description 3
- IQVZEXVCOKLIID-UHFFFAOYSA-N 3-(1,3-oxathian-2-yl)pyridine Chemical compound S1CCCOC1C1=CC=CN=C1 IQVZEXVCOKLIID-UHFFFAOYSA-N 0.000 description 3
- XDQFQVHEHFURRR-UHFFFAOYSA-N 3-(3-chloropropylsulfanylmethyl)pyridazine Chemical compound ClCCCSCC1=CC=CN=N1 XDQFQVHEHFURRR-UHFFFAOYSA-N 0.000 description 3
- SDWLIMRWXKRKCC-UHFFFAOYSA-N 3-(3-chloropropylsulfanylmethyl)pyridine Chemical compound ClCCCSCC1=CC=CN=C1 SDWLIMRWXKRKCC-UHFFFAOYSA-N 0.000 description 3
- VHPBYSDWVFDBAO-UHFFFAOYSA-N 3-(4-chlorobutylsulfanylmethyl)pyridine Chemical compound ClCCCCSCC1=CC=CN=C1 VHPBYSDWVFDBAO-UHFFFAOYSA-N 0.000 description 3
- NLNZUZDWYRZYCH-UHFFFAOYSA-N 3-(thiolan-2-yl)pyridazine Chemical compound C1CCSC1C1=CC=CN=N1 NLNZUZDWYRZYCH-UHFFFAOYSA-N 0.000 description 3
- UNDZTSGXNXEERW-UHFFFAOYSA-N 3-(thiolan-2-yl)pyridine Chemical compound C1CCSC1C1=CC=CN=C1 UNDZTSGXNXEERW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 229940030600 antihypertensive agent Drugs 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 3
- 125000005905 mesyloxy group Chemical group 0.000 description 3
- YPQLWVTYEHICIE-UHFFFAOYSA-N methyl 2-pyridin-2-yl-1,3-dithiane-2-carbodithioate Chemical compound C=1C=CC=NC=1C1(C(=S)SC)SCCCS1 YPQLWVTYEHICIE-UHFFFAOYSA-N 0.000 description 3
- MUHLCZXCVZTCHJ-UHFFFAOYSA-N methyl 2-pyridin-3-ylthiolane-2-carbodithioate Chemical compound C=1C=CN=CC=1C1(C(=S)SC)CCCS1 MUHLCZXCVZTCHJ-UHFFFAOYSA-N 0.000 description 3
- QBCXWMKZJUWICP-UHFFFAOYSA-N methyl 2-quinolin-2-ylthiolane-2-carbodithioate Chemical compound C=1C=C2C=CC=CC2=NC=1C1(C(=S)SC)CCCS1 QBCXWMKZJUWICP-UHFFFAOYSA-N 0.000 description 3
- XXCFJIHBZYKRJW-UHFFFAOYSA-N pyridin-2-ylmethyl carbamimidothioate Chemical compound NC(=N)SCC1=CC=CC=N1 XXCFJIHBZYKRJW-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 3
- NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 description 2
- TXPFNZZSEXQEDY-UHFFFAOYSA-N 2-(1,3-dithian-2-yl)pyridine Chemical compound S1CCCSC1C1=CC=CC=N1 TXPFNZZSEXQEDY-UHFFFAOYSA-N 0.000 description 2
- GFHPSQFCHUIFTO-UHFFFAOYSA-N 2-(chloromethyl)pyrazine Chemical compound ClCC1=CN=CC=N1 GFHPSQFCHUIFTO-UHFFFAOYSA-N 0.000 description 2
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 2
- VPKBTDAXPNJXMI-UHFFFAOYSA-N 2-(thian-2-yl)pyridine Chemical compound S1CCCCC1C1=CC=CC=N1 VPKBTDAXPNJXMI-UHFFFAOYSA-N 0.000 description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
- JYJMYHNOYHIKPY-UHFFFAOYSA-N 3-(3-chloropropylsulfanylmethyl)quinoline Chemical compound C1=CC=CC2=CC(CSCCCCl)=CN=C21 JYJMYHNOYHIKPY-UHFFFAOYSA-N 0.000 description 2
- DSOGFOBIDOVCHN-UHFFFAOYSA-N 3-(chloromethyl)quinoline Chemical compound C1=CC=CC2=CC(CCl)=CN=C21 DSOGFOBIDOVCHN-UHFFFAOYSA-N 0.000 description 2
- XSUAZSUYTPUYKT-UHFFFAOYSA-N 4-(2-methylbutan-2-yloxy)-1-pyridin-2-ylbutan-1-ol Chemical compound CCC(C)(C)OCCCC(O)C1=CC=CC=N1 XSUAZSUYTPUYKT-UHFFFAOYSA-N 0.000 description 2
- FCLFDWYNWGTMEL-UHFFFAOYSA-N 4-(3-chloropropylsulfanylmethyl)pyridine Chemical compound ClCCCSCC1=CC=NC=C1 FCLFDWYNWGTMEL-UHFFFAOYSA-N 0.000 description 2
- PTDLMLOSMYPGAV-UHFFFAOYSA-N 4-(thiolan-2-yl)pyridine Chemical compound C1CCSC1C1=CC=NC=C1 PTDLMLOSMYPGAV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002641 lithium Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 2
- VHBLKUKVGSWPQE-UHFFFAOYSA-N methyl 2-pyridin-2-ylthiane-2-carbodithioate Chemical compound C=1C=CC=NC=1C1(C(=S)SC)CCCCS1 VHBLKUKVGSWPQE-UHFFFAOYSA-N 0.000 description 2
- RYEKHCGVBQHBCO-UHFFFAOYSA-N methyl 2-pyridin-4-ylthiolane-2-carbodithioate Chemical compound C=1C=NC=CC=1C1(C(=S)SC)CCCS1 RYEKHCGVBQHBCO-UHFFFAOYSA-N 0.000 description 2
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 2
- ZLLXHMAAZDNXQV-UHFFFAOYSA-N n-methyl-2-pyridazin-3-ylthiolane-2-carbothioamide Chemical compound C=1C=CN=NC=1C1(C(=S)NC)CCCS1 ZLLXHMAAZDNXQV-UHFFFAOYSA-N 0.000 description 2
- QGNOTTIQUOVMCT-UHFFFAOYSA-N n-methyl-2-pyridin-2-yloxolane-2-carbothioamide Chemical compound C=1C=CC=NC=1C1(C(=S)NC)CCCO1 QGNOTTIQUOVMCT-UHFFFAOYSA-N 0.000 description 2
- QGVLLXVIHPJVGF-UHFFFAOYSA-N n-methyl-2-pyridin-2-ylthiane-2-carbothioamide Chemical compound C=1C=CC=NC=1C1(C(=S)NC)CCCCS1 QGVLLXVIHPJVGF-UHFFFAOYSA-N 0.000 description 2
- SBWUJGPHNXIUAV-UHFFFAOYSA-N n-methyl-2-pyridin-3-ylthiane-2-carbothioamide Chemical compound C=1C=CN=CC=1C1(C(=S)NC)CCCCS1 SBWUJGPHNXIUAV-UHFFFAOYSA-N 0.000 description 2
- CJDIUYZQGNXWRB-UHFFFAOYSA-N n-methyl-2-pyridin-3-ylthiolane-2-carbothioamide Chemical compound C=1C=CN=CC=1C1(C(=S)NC)CCCS1 CJDIUYZQGNXWRB-UHFFFAOYSA-N 0.000 description 2
- AZVQGTWZBHYFMN-UHFFFAOYSA-N n-methyl-2-quinolin-2-ylthiolane-2-carbothioamide Chemical compound C=1C=C2C=CC=CC2=NC=1C1(C(=S)NC)CCCS1 AZVQGTWZBHYFMN-UHFFFAOYSA-N 0.000 description 2
- MLOMASOCCJTFIU-UHFFFAOYSA-N n-methyl-2-quinolin-3-ylthiolane-2-carbothioamide Chemical compound C=1N=C2C=CC=CC2=CC=1C1(C(=S)NC)CCCS1 MLOMASOCCJTFIU-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- LVEMROJFCIAJIX-UHFFFAOYSA-N pyridin-4-ylmethyl carbamimidothioate Chemical compound NC(=N)SCC1=CC=NC=C1 LVEMROJFCIAJIX-UHFFFAOYSA-N 0.000 description 2
- HICLRQYRFFDRSM-UHFFFAOYSA-N quinolin-2-ylmethyl carbamimidothioate Chemical compound C1=CC=CC2=NC(CSC(=N)N)=CC=C21 HICLRQYRFFDRSM-UHFFFAOYSA-N 0.000 description 2
- BBTQILBUDSANDJ-UHFFFAOYSA-N quinolin-3-ylmethyl carbamimidothioate Chemical compound C1=CC=CC2=CC(CSC(=N)N)=CN=C21 BBTQILBUDSANDJ-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 description 1
- YBHGDVXJKSNYKM-UHFFFAOYSA-N 2-pyridin-2-yl-1,3-dithiane-2-carbothioamide Chemical compound C=1C=CC=NC=1C1(C(=S)N)SCCCS1 YBHGDVXJKSNYKM-UHFFFAOYSA-N 0.000 description 1
- CNQCWYFDIQSALX-UHFFFAOYSA-N 3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1 CNQCWYFDIQSALX-UHFFFAOYSA-N 0.000 description 1
- ULIMAJKRBSHEJJ-UHFFFAOYSA-N 4-(2-methylbutan-2-yloxy)-1-phenylbutan-1-ol Chemical compound CCC(C)(C)OCCCC(O)C1=CC=CC=C1 ULIMAJKRBSHEJJ-UHFFFAOYSA-N 0.000 description 1
- WZIYCIBURCPKAR-UHFFFAOYSA-N 4-(chloromethyl)pyridine Chemical compound ClCC1=CC=NC=C1 WZIYCIBURCPKAR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101150071384 CIRBP gene Proteins 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 101100167307 Xenopus laevis cirbp-a gene Proteins 0.000 description 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- FPNFFUQLQGAGKB-UHFFFAOYSA-N n-methyl-2-pyrazin-2-ylthiolane-2-carbothioamide Chemical compound C=1N=CC=NC=1C1(C(=S)NC)CCCS1 FPNFFUQLQGAGKB-UHFFFAOYSA-N 0.000 description 1
- CZIHYFJCJDWJJN-UHFFFAOYSA-N n-methyl-2-pyridin-2-yl-1,3-dithiane-2-carbothioamide Chemical compound C=1C=CC=NC=1C1(C(=S)NC)SCCCS1 CZIHYFJCJDWJJN-UHFFFAOYSA-N 0.000 description 1
- MKUKLTIVRZHGCX-UHFFFAOYSA-N n-methyl-2-pyridin-2-yl-1,3-oxathiane-2-carbothioamide Chemical compound C=1C=CC=NC=1C1(C(=S)NC)OCCCS1 MKUKLTIVRZHGCX-UHFFFAOYSA-N 0.000 description 1
- KUDZUJIPCAPOLD-UHFFFAOYSA-N n-methyl-2-pyridin-3-yl-1,3-oxathiane-2-carbothioamide Chemical compound C=1C=CN=CC=1C1(C(=S)NC)OCCCS1 KUDZUJIPCAPOLD-UHFFFAOYSA-N 0.000 description 1
- ZNOMKSQQKDDAPY-UHFFFAOYSA-N n-methyl-2-pyridin-4-ylthiolane-2-carbothioamide Chemical compound C=1C=NC=CC=1C1(C(=S)NC)CCCS1 ZNOMKSQQKDDAPY-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000010414 supernatant solution Substances 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical class CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Toys (AREA)
- Lasers (AREA)
- Instructional Devices (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8018035A FR2488609A1 (fr) | 1980-08-18 | 1980-08-18 | Nouveaux derives de la thioformamide, leur preparation et les medicaments qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO810962L true NO810962L (no) | 1982-02-19 |
Family
ID=9245232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810962A NO810962L (no) | 1980-08-18 | 1981-03-20 | Fremgangsmaate for fremstilling av nye derivater av tioformamid |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4379154A (ru) |
| EP (2) | EP0046417B1 (ru) |
| JP (1) | JPS5742687A (ru) |
| KR (1) | KR850001043B1 (ru) |
| AT (1) | ATE14730T1 (ru) |
| CA (1) | CA1161039A (ru) |
| DE (1) | DE3161861D1 (ru) |
| DK (1) | DK158735C (ru) |
| ES (2) | ES501060A0 (ru) |
| FI (1) | FI810835L (ru) |
| FR (1) | FR2488609A1 (ru) |
| GR (1) | GR72767B (ru) |
| HU (1) | HU187325B (ru) |
| IE (1) | IE51263B1 (ru) |
| IL (1) | IL62380A (ru) |
| MA (1) | MA19106A1 (ru) |
| NO (1) | NO810962L (ru) |
| NZ (1) | NZ197071A (ru) |
| OA (1) | OA06767A (ru) |
| PH (1) | PH16520A (ru) |
| PL (2) | PL130530B1 (ru) |
| PT (1) | PT72718B (ru) |
| SU (2) | SU1093248A3 (ru) |
| ZA (1) | ZA813159B (ru) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2511371A1 (fr) * | 1981-08-11 | 1983-02-18 | Rhone Poulenc Sante | Nouveaux nitriles heterocycliques, leur preparation et leur utilisation pour la preparation de medicaments |
| FR2528849B1 (fr) * | 1982-06-17 | 1985-06-21 | Rhone Poulenc Sante | Nouveaux derives de la thioformamide, leur preparation et les medicaments qui les contiennent |
| FR2573428B1 (fr) * | 1984-11-20 | 1987-01-30 | Rhone Poulenc Sante | Nouveaux derives de la thioformamide, leur preparation et les medicaments qui les contiennent |
| GB8907306D0 (en) * | 1989-03-31 | 1989-05-17 | May & Baker Ltd | New compositions of matter |
| FR2653770B1 (fr) * | 1989-10-31 | 1992-01-03 | Rhone Poulenc Sante | Procede de preparation de (pyridyl-3)-2 tetrahydrothiopyrannecarbothioamide-2-oxydes-1-(1r,2r), les (pyridyl-3)-2 tetrhydrothiopyrannecarbothioamide-2-oxydes-1-(1r,2r) ainsi obtenus et les compositions pharmaceutiques qui les contiennent. |
| JPH04211048A (ja) * | 1990-03-05 | 1992-08-03 | Mitsubishi Kasei Corp | チオカルバモイルアセトニトリル誘導体 |
| HUT66229A (en) * | 1991-10-14 | 1994-10-28 | Eisai Co Ltd | Thioformamide derivatives and process for producing them and pharmaceutical compositions containing them |
| US5625068A (en) * | 1995-06-05 | 1997-04-29 | American Cyanamid Company | Substituted quinoline herbicide intermediates and process |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1056205B (it) * | 1970-07-30 | 1982-01-30 | Fujisawa Pharmaceutical Co | Composto a paste di derivati tioa cetammidici e loro sali procedimento per il suo ottenimento e composizioni che lo contengono |
| DK627174A (ru) * | 1974-01-17 | 1975-09-08 | Ciba Geigy Ag | |
| IE49570B1 (en) * | 1979-03-30 | 1985-10-30 | Rhone Poulenc Ind | 2-(pyrid-2-yl)tetrahydrothiophene derivatives |
| FR2452488A1 (fr) * | 1979-03-30 | 1980-10-24 | Rhone Poulenc Ind | Nouveaux derives du (pyridyl-2)-2 tetrahydrothiophene, leur preparation et les medicaments qui les contiennent |
| JPS6134433A (ja) * | 1984-08-31 | 1986-02-18 | Nippon Telegr & Teleph Corp <Ntt> | ｘｙ平面位置決め用アクチユエ−タ装置 |
-
1980
- 1980-08-18 FR FR8018035A patent/FR2488609A1/fr active Granted
-
1981
- 1981-03-12 DE DE8181400381T patent/DE3161861D1/de not_active Expired
- 1981-03-12 OA OA57352BISD patent/OA06767A/xx unknown
- 1981-03-12 EP EP81400381A patent/EP0046417B1/fr not_active Expired
- 1981-03-12 AT AT82110740T patent/ATE14730T1/de not_active IP Right Cessation
- 1981-03-12 EP EP82110740A patent/EP0077083B1/fr not_active Expired
- 1981-03-16 IL IL62380A patent/IL62380A/xx unknown
- 1981-03-18 FI FI810835A patent/FI810835L/fi not_active Application Discontinuation
- 1981-03-18 HU HU81698A patent/HU187325B/hu unknown
- 1981-03-20 GR GR64458A patent/GR72767B/el unknown
- 1981-03-20 NO NO810962A patent/NO810962L/no unknown
- 1981-03-21 MA MA19312A patent/MA19106A1/fr unknown
- 1981-03-23 PT PT72718A patent/PT72718B/pt unknown
- 1981-03-23 DK DK130781A patent/DK158735C/da not_active IP Right Cessation
- 1981-04-03 ES ES501060A patent/ES501060A0/es active Granted
- 1981-04-07 PL PL1981230552A patent/PL130530B1/pl unknown
- 1981-04-07 PL PL1981239331A patent/PL130679B1/pl unknown
- 1981-04-10 SU SU813266246A patent/SU1093248A3/ru active
- 1981-05-11 IE IE1036/81A patent/IE51263B1/en unknown
- 1981-05-12 ZA ZA00813159A patent/ZA813159B/xx unknown
- 1981-05-12 NZ NZ197071A patent/NZ197071A/xx unknown
- 1981-05-14 CA CA000377595A patent/CA1161039A/fr not_active Expired
- 1981-05-18 US US06/264,550 patent/US4379154A/en not_active Expired - Fee Related
- 1981-05-29 JP JP56081187A patent/JPS5742687A/ja active Granted
- 1981-05-30 KR KR1019810001943A patent/KR850001043B1/ko active IP Right Grant
- 1981-07-07 ES ES503727A patent/ES8301475A1/es not_active Expired
-
1982
- 1982-03-29 SU SU823415750A patent/SU1209029A3/ru active
- 1982-06-01 PH PH25692A patent/PH16520A/en unknown
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