NL7908191A - Nieuwe dithiocarbamaten, de bereiding ervan, farmaceu- tische preparaten die de nieuwe derivaten bavatten, alsmede de bereiding daarvan. - Google Patents

Nieuwe dithiocarbamaten, de bereiding ervan, farmaceu- tische preparaten die de nieuwe derivaten bavatten, alsmede de bereiding daarvan. Download PDF

Info

Publication number: NL7908191A
Authority: NL; Netherlands
Prior art keywords: group; alkyl; dithiocarbamate; hydroxy; carbon atoms
Prior art date: 1978-11-16

Application number

NL7908191A

Other languages

English (en)

Dutch (nl)

Original Assignee

Rhone Poulenc Ind

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-11-16

Filing date

1979-11-08

Publication date

1980-05-20

1979-11-08 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1980-05-20 Publication of NL7908191A publication Critical patent/NL7908191A/nl

Links

239000012990 dithiocarbamate Substances 0.000 title claims description 99
-1 THEIR PREPARATION Substances 0.000 title claims description 42
238000002360 preparation method Methods 0.000 title claims description 19
239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
150000004659 dithiocarbamates Chemical class 0.000 title description 4
238000000034 method Methods 0.000 claims description 53
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 52
150000001875 compounds Chemical class 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 39
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
239000002585 base Substances 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 7
230000003287 optical effect Effects 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 2
125000005122 aminoalkylamino group Chemical group 0.000 claims 1
150000002118 epoxides Chemical class 0.000 claims 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 240
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 88
239000000243 solution Substances 0.000 description 82
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
239000012153 distilled water Substances 0.000 description 57
238000006243 chemical reaction Methods 0.000 description 52
239000000203 mixture Substances 0.000 description 52
239000000047 product Substances 0.000 description 49
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
239000000155 melt Substances 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
238000001914 filtration Methods 0.000 description 39
239000000725 suspension Substances 0.000 description 39
238000001953 recrystallisation Methods 0.000 description 33
229910052700 potassium Inorganic materials 0.000 description 26
239000011591 potassium Substances 0.000 description 26
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 25
239000013078 crystal Substances 0.000 description 24
239000000377 silicon dioxide Substances 0.000 description 24
238000009835 boiling Methods 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 20
238000010828 elution Methods 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
239000002904 solvent Substances 0.000 description 10
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 9
238000001816 cooling Methods 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
238000011282 treatment Methods 0.000 description 7
235000012239 silicon dioxide Nutrition 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
239000012080 ambient air Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229940099259 vaseline Drugs 0.000 description 5
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
201000006353 Filariasis Diseases 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002329 infrared spectrum Methods 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
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
239000004264 Petrolatum Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
235000019271 petrolatum Nutrition 0.000 description 3
229940066842 petrolatum Drugs 0.000 description 3
230000007017 scission Effects 0.000 description 3
238000005406 washing Methods 0.000 description 3
LCMPIWIWBGHBOY-UHFFFAOYSA-N (3-chloro-2-oxopropyl) acetate Chemical compound CC(=O)OCC(=O)CCl LCMPIWIWBGHBOY-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000243780 Heligmosomoides polygyrus Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004181 carboxyalkyl group Chemical group 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000010908 decantation Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
230000000968 intestinal effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
AUQDWNOSVDUIAT-UHFFFAOYSA-N methyl 5-bromo-4-oxopentanoate Chemical compound COC(=O)CCC(=O)CBr AUQDWNOSVDUIAT-UHFFFAOYSA-N 0.000 description 2
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
GLBUZFYJIIWCFB-UHFFFAOYSA-N propanethioyl chloride Chemical compound CCC(Cl)=S GLBUZFYJIIWCFB-UHFFFAOYSA-N 0.000 description 2
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
229940100445 wheat starch Drugs 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
QRYAEUULRGDETI-UHFFFAOYSA-M (4,4-dimethyl-3-oxopentyl)-trimethylazanium;iodide Chemical compound [I-].CC(C)(C)C(=O)CC[N+](C)(C)C QRYAEUULRGDETI-UHFFFAOYSA-M 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-UHFFFAOYSA-N 0.000 description 1
SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
CILPHQCEVYJUDN-VWYCJHECSA-N 2-[(1s,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxyacetic acid Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1OCC(O)=O CILPHQCEVYJUDN-VWYCJHECSA-N 0.000 description 1
BANFRNTVKCHZDE-UHFFFAOYSA-N 2-bromo-1-(3-methylphenyl)ethanone Chemical compound CC1=CC=CC(C(=O)CBr)=C1 BANFRNTVKCHZDE-UHFFFAOYSA-N 0.000 description 1
PUPDAQGFJMQNBK-UHFFFAOYSA-N 2-bromo-2-methylpropan-1-ol Chemical compound CC(C)(Br)CO PUPDAQGFJMQNBK-UHFFFAOYSA-N 0.000 description 1
KLTWFFAVGWWIKL-UHFFFAOYSA-N 2-bromo-2-methylpropanal Chemical compound CC(C)(Br)C=O KLTWFFAVGWWIKL-UHFFFAOYSA-N 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
HQRSIMQXCAWAJB-UHFFFAOYSA-N 3,3,3-trifluoro-2-phenylpropanoic acid Chemical compound OC(=O)C(C(F)(F)F)C1=CC=CC=C1 HQRSIMQXCAWAJB-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 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
241000283690 Bos taurus Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
FMSSTWGVVMAWCY-UHFFFAOYSA-N ClO.CNC Chemical compound ClO.CNC FMSSTWGVVMAWCY-UHFFFAOYSA-N 0.000 description 1
DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000283073 Equus caballus Species 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
208000006968 Helminthiasis Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000243994 Litomosoides carinii Species 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
101100049053 Mus musculus Vash1 gene Proteins 0.000 description 1
HQGBWUXEXCCXBU-UHFFFAOYSA-N N,N-diethylethanamine hypobromous acid Chemical compound BrO.CCN(CC)CC HQGBWUXEXCCXBU-UHFFFAOYSA-N 0.000 description 1
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
241001494479 Pecora Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
241000144290 Sigmodon hispidus Species 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
ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003570 air Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
XPHBRTNHVJSEQD-UHFFFAOYSA-N anidoxime Chemical compound C=1C=CC=CC=1C(CCN(CC)CC)=NOC(=O)NC1=CC=C(OC)C=C1 XPHBRTNHVJSEQD-UHFFFAOYSA-N 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
229940124339 anthelmintic agent Drugs 0.000 description 1
239000000921 anthelmintic agent Substances 0.000 description 1
230000000721 bacterilogical effect Effects 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
XLKNMWIXNFVJRR-UHFFFAOYSA-N boron potassium Chemical compound [B].[K] XLKNMWIXNFVJRR-UHFFFAOYSA-N 0.000 description 1
229950005228 bromoform Drugs 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
208000008576 dracunculiasis Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000001926 lymphatic effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000000053 physical method Methods 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000829 suppository 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
150000003512 tertiary amines Chemical class 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NL7908191A 1978-11-16 1979-11-08 Nieuwe dithiocarbamaten, de bereiding ervan, farmaceu- tische preparaten die de nieuwe derivaten bavatten, alsmede de bereiding daarvan. NL7908191A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7832388		1978-11-16
FR7832388A FR2441613A1 (fr)	1978-11-16	1978-11-16	Nouveaux dithiocarbamates, leur preparation et les medicaments qui les contiennent

Publications (1)

Publication Number	Publication Date
NL7908191A true NL7908191A (nl)	1980-05-20

Family

ID=9214966

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7908191A NL7908191A (nl)	1978-11-16	1979-11-08	Nieuwe dithiocarbamaten, de bereiding ervan, farmaceu- tische preparaten die de nieuwe derivaten bavatten, alsmede de bereiding daarvan.

Country Status (19)

Country	Link
US (1)	US4271167A (fr)
JP (1)	JPS5592371A (fr)
AT (1)	AT362796B (fr)
AU (1)	AU5278579A (fr)
BE (1)	BE880097A (fr)
DE (1)	DE2946395A1 (fr)
DK (1)	DK484879A (fr)
ES (2)	ES486050A1 (fr)
FR (1)	FR2441613A1 (fr)
GB (1)	GB2037279A (fr)
IL (1)	IL58729A0 (fr)
IT (1)	IT1127242B (fr)
LU (1)	LU81892A1 (fr)
NL (1)	NL7908191A (fr)
NZ (1)	NZ192135A (fr)
OA (1)	OA06371A (fr)
PT (1)	PT70456A (fr)
SE (1)	SE7909441L (fr)
ZA (1)	ZA796147B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5560853A (en) *	1990-08-30	1996-10-01	Pennzoil Products Company	Dithiocarbamoyl diols and borate esters thereof for use in lubricant compositions
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 (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3726880A (en) *	1971-09-07	1973-04-10	Parke Davis & Co	Organic amides and methods for their production
US3725422A (en) *	1971-09-07	1973-04-03	Parke Davis & Co	New organic sulfur compounds and methods for their production
US3732216A (en) *	1971-11-17	1973-05-08	Smith Kline French Lab	3-heteroaryl-2-thio-1,3-thiazane-2,4-diones
US4039550A (en) *	1976-07-26	1977-08-02	Sterling Drug Inc.	Lower-alkyl (5-substituted-2-pyridyl)carbamodithioates
NL7804977A (nl) *	1977-05-17	1978-11-21	Rhone Poulenc Ind	Nieuwe 4-hydroxythiazolidinethion-2-derivaten, de be- reiding ervan en preparaten, die de nieuwe derivaten bevatten.
FR2391212A1 (fr) *	1977-05-17	1978-12-15	Rhone Poulenc Ind	Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent

1978
- 1978-11-16 FR FR7832388A patent/FR2441613A1/fr not_active Withdrawn
1979
- 1979-11-01 OA OA56932A patent/OA06371A/fr unknown
- 1979-11-08 NL NL7908191A patent/NL7908191A/nl not_active Application Discontinuation
- 1979-11-13 GB GB7939313A patent/GB2037279A/en not_active Withdrawn
- 1979-11-14 JP JP14663179A patent/JPS5592371A/ja active Pending
- 1979-11-14 AU AU52785/79A patent/AU5278579A/en not_active Abandoned
- 1979-11-14 AT AT0727779A patent/AT362796B/de not_active IP Right Cessation
- 1979-11-14 US US06/094,288 patent/US4271167A/en not_active Expired - Lifetime
- 1979-11-15 SE SE7909441A patent/SE7909441L/xx unknown
- 1979-11-15 PT PT70456A patent/PT70456A/fr unknown
- 1979-11-15 IL IL58729A patent/IL58729A0/xx unknown
- 1979-11-15 DK DK484879A patent/DK484879A/da unknown
- 1979-11-15 NZ NZ192135A patent/NZ192135A/xx unknown
- 1979-11-15 LU LU81892A patent/LU81892A1/fr unknown
- 1979-11-15 ZA ZA00796147A patent/ZA796147B/xx unknown
- 1979-11-16 BE BE0/198161A patent/BE880097A/fr unknown
- 1979-11-16 IT IT27344/79A patent/IT1127242B/it active
- 1979-11-16 DE DE19792946395 patent/DE2946395A1/de not_active Withdrawn
- 1979-11-16 ES ES486050A patent/ES486050A1/es not_active Expired
1980
- 1980-01-10 ES ES487588A patent/ES487588A0/es active Granted

Also Published As

Publication number	Publication date
PT70456A (fr)	1979-12-01
AU5278579A (en)	1980-05-22
ES486050A1 (es)	1980-05-16
ES8100264A1 (es)	1980-11-01
ZA796147B (en)	1980-11-26
ATA727779A (de)	1980-11-15
IT7927344A0 (it)	1979-11-16
US4271167A (en)	1981-06-02
DK484879A (da)	1980-05-17
ES487588A0 (es)	1980-11-01
OA06371A (fr)	1981-08-31
AT362796B (de)	1981-06-10
NZ192135A (en)	1981-12-15
FR2441613A1 (fr)	1980-06-13
SE7909441L (sv)	1980-05-17
GB2037279A (en)	1980-07-09
IT1127242B (it)	1986-05-21
JPS5592371A (en)	1980-07-12
BE880097A (fr)	1980-05-16
IL58729A0 (en)	1980-02-29
DE2946395A1 (de)	1980-06-04
LU81892A1 (fr)	1980-06-05

Legal Events

Date	Code	Title	Description
1982-07-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US20040236116A1 (en)	2004-11-25	Novel bicyclic and tricyclic cannabinoids
PL163045B1 (pl)	1994-02-28	Sposób wytwarzania nowych pochodnych kwasu 1,3-di oksanoalkenowego PL PL PL
CH655114A5 (fr)	1986-03-27	Derives de l'imidazotetrazinone, leur preparation et compositions pharmaceutiques les contenant.
FR2528847A1 (fr)	1983-12-23	Produits nouveaux de la classe des carbapenems et leur application en tant qu'antibiotiques
EP0287890A1 (fr)	1988-10-26	Pyrroles substitués
US4268678A (en)	1981-05-19	4-(Arylaliphatic)isoxazoles
FR2644456A1 (fr)	1990-09-21	Nouveaux derives du 1h, 3h-pyrrolo(1,2-c)thiazolecarboxamide-7, leur preparation et les compositions pharmaceutiques qui les contiennent
DE3109086A1 (de)	1981-12-24	2-penem-3-carbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung
EP0300278A2 (fr)	1989-01-25	Procédé de préparation de pyrroles 2-substituées
FR2471381A1 (fr)	1981-06-19	Derives de l'ergoline, procede pour les preparer et leur emploi comme medicaments
EP0330057A2 (fr)	1989-08-30	Pyrimidines substituées
NL7908191A (nl)	1980-05-20	Nieuwe dithiocarbamaten, de bereiding ervan, farmaceu- tische preparaten die de nieuwe derivaten bavatten, alsmede de bereiding daarvan.
AT391865B (de)	1990-12-10	Verfahren zur herstellung neuer benzothiophenderivate
EP0298921B1 (fr)	1992-12-23	1,2-Benzisoxazoles et 1,2-benzisothiazoles
US4049816A (en)	1977-09-20	Antiviral 2-amino-5-[1-(indol-3-yl)alkyl]-2-thiazolin-4-ones
DD283817A5 (de)	1990-10-24	Verfahren zur herstellung heterocyclischer nitromethanderivate
FR2470770A1 (fr)	1981-06-12	Nouveaux ethers de b-imidazolylethyle de quinoleine-2 ou 4-methanols, utiles notamment comme antimicrobiens, et leur procede de preparation
EP0408437B1 (fr)	1994-06-08	Dérivés d'alkylimino-2 benzothiazoline, leurs procédés de préparation et les médicaments les contenant
EP0419410A2 (fr)	1991-03-27	Alkanophénones
GB2098593A (en)	1982-11-24	Isoxazoles
EP0339342A1 (fr)	1989-11-02	N-aminopyrrols N-substitués
EP0334014A2 (fr)	1989-09-27	Imidazolinones et imidazolethiones substituées
KR940009189A (ko)	1994-05-20	페넴 화합물
DE3316093A1 (de)	1983-11-10	Allylaminderivate, verfahren zu ihrer herstellung und ihre verwendung
FR2662160A1 (fr)	1991-11-22	Derives d'alkylthio-3 propyl-3 benzothiazoline leur preparation et les medicaments les contenant.