LU83795A1 - Xanthates,leur preparation et leur utilisation - Google Patents
Xanthates,leur preparation et leur utilisation Download PDFInfo
- Publication number
- LU83795A1 LU83795A1 LU83795A LU83795A LU83795A1 LU 83795 A1 LU83795 A1 LU 83795A1 LU 83795 A LU83795 A LU 83795A LU 83795 A LU83795 A LU 83795A LU 83795 A1 LU83795 A1 LU 83795A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- xanthate
- alkali metal
- group
- sodium
- potassium
- Prior art date
Links
- 239000012991 xanthate Substances 0.000 title claims description 38
- 238000002360 preparation method Methods 0.000 title claims description 9
- -1 cyclododecyl Chemical group 0.000 claims description 29
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims description 28
- 239000011734 sodium Substances 0.000 claims description 27
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 25
- 229910052783 alkali metal Inorganic materials 0.000 claims description 23
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 22
- 229910052708 sodium Inorganic materials 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000001340 alkali metals Chemical group 0.000 claims description 17
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 16
- 229910052700 potassium Inorganic materials 0.000 claims description 16
- 239000011591 potassium Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 230000001790 virustatic effect Effects 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- KMJJWVCLFJXUQF-UHFFFAOYSA-M sodium;cyclohexyloxymethanedithioate Chemical compound [Na+].[S-]C(=S)OC1CCCCC1 KMJJWVCLFJXUQF-UHFFFAOYSA-M 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WIKDURKPSJEWGB-UHFFFAOYSA-N phenylmethoxymethanedithioic acid Chemical compound SC(=S)OCC1=CC=CC=C1 WIKDURKPSJEWGB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- 241000212342 Sium Species 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 2
- OPLBMJFYACKMRJ-UHFFFAOYSA-N o-cyclohexyl methylsulfanylmethanethioate Chemical compound CSC(=S)OC1CCCCC1 OPLBMJFYACKMRJ-UHFFFAOYSA-N 0.000 claims description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 241000208202 Linaceae Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 claims 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- JZGDVCTYNFVQEC-UHFFFAOYSA-M potassium;adamantane-1-carboxylate Chemical compound [K+].C1C(C2)CC3CC2CC1(C(=O)[O-])C3 JZGDVCTYNFVQEC-UHFFFAOYSA-M 0.000 claims 1
- QDIGBJJRWUZARS-UHFFFAOYSA-M potassium;decanoate Chemical compound [K+].CCCCCCCCCC([O-])=O QDIGBJJRWUZARS-UHFFFAOYSA-M 0.000 claims 1
- UONHJSWTEBJXNB-UHFFFAOYSA-M potassium;heptoxymethanedithioate Chemical compound [K+].CCCCCCCOC([S-])=S UONHJSWTEBJXNB-UHFFFAOYSA-M 0.000 claims 1
- GBBPFRKNGUDLLB-UHFFFAOYSA-M sodium;cyclododecanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CCCCCCCCCCC1 GBBPFRKNGUDLLB-UHFFFAOYSA-M 0.000 claims 1
- LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241000700605 Viruses Species 0.000 description 8
- 230000000840 anti-viral effect Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 210000004883 areola Anatomy 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 206010022000 influenza Diseases 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910052573 porcelain Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229960005486 vaccine Drugs 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 241000712461 unidentified influenza virus Species 0.000 description 2
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 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
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 244000298479 Cichorium intybus Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241000353621 Eilat virus Species 0.000 description 1
- 235000014066 European mistletoe Nutrition 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 244000152640 Rhipsalis cassutha Species 0.000 description 1
- 235000012300 Rhipsalis cassutha Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 210000001691 amnion Anatomy 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002962 plaque-reduction assay Methods 0.000 description 1
- ROKMMAWTMJKDKE-UHFFFAOYSA-M potassium;decoxymethanedithioate Chemical compound [K+].CCCCCCCCCCOC([S-])=S ROKMMAWTMJKDKE-UHFFFAOYSA-M 0.000 description 1
- ZTHBGWDIOJXYNC-UHFFFAOYSA-M potassium;hexoxymethanedithioate Chemical class [K+].CCCCCCOC([S-])=S ZTHBGWDIOJXYNC-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/02—Monothiocarbonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3044525 | 1980-11-26 | ||
DE3044525 | 1980-11-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
LU83795A1 true LU83795A1 (fr) | 1983-09-01 |
Family
ID=6117628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LU83795A LU83795A1 (fr) | 1980-11-26 | 1981-11-26 | Xanthates,leur preparation et leur utilisation |
Country Status (24)
Country | Link |
---|---|
US (2) | US4602037A (en:Method) |
JP (2) | JPS5943944B2 (en:Method) |
KR (1) | KR870001238B1 (en:Method) |
AR (1) | AR230264A1 (en:Method) |
AT (1) | AT376202B (en:Method) |
AU (1) | AU549653B2 (en:Method) |
BE (1) | BE891245A (en:Method) |
CA (1) | CA1175047A (en:Method) |
CH (1) | CH651546A5 (en:Method) |
DE (1) | DE3146772C2 (en:Method) |
DK (1) | DK170068B1 (en:Method) |
ES (1) | ES507430A0 (en:Method) |
FR (1) | FR2494689B1 (en:Method) |
GB (1) | GB2091244B (en:Method) |
GR (1) | GR76308B (en:Method) |
HU (1) | HU187476B (en:Method) |
IE (1) | IE51944B1 (en:Method) |
IT (1) | IT1195297B (en:Method) |
LU (1) | LU83795A1 (en:Method) |
NL (1) | NL8105326A (en:Method) |
PL (1) | PL129383B1 (en:Method) |
SE (1) | SE450251B (en:Method) |
SG (1) | SG29285G (en:Method) |
YU (1) | YU42120B (en:Method) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR870001238B1 (ko) * | 1980-11-26 | 1987-06-26 | 메르츠+캄패니 게엠베하 앤드 캄패니 | 크산틴산염의 제조방법 |
IT1213453B (it) * | 1985-08-02 | 1989-12-20 | Merz & Co Gmbh & Co | Composizione farmaceutica. |
DE3625948A1 (de) * | 1985-08-02 | 1987-02-19 | Merz & Co Gmbh & Co | Antivirale und antitumor-zusammensetzung, verfahren zu deren herstellung und deren verwendung |
AT388499B (de) * | 1985-08-02 | 1989-06-26 | Merz & Co Gmbh & Co | Verfahren zur herstellung einer antiviralen und antitumor-zusammensetzung, und deren verwendung |
US5284664A (en) * | 1988-08-04 | 1994-02-08 | Kremers-Urban Company | Method of treating the symptoms of Alzheimer's disease |
US5055296A (en) * | 1988-08-04 | 1991-10-08 | Wagle Sudhakar S | Method of treating chronic fatigue syndrome |
US5316775A (en) * | 1988-08-04 | 1994-05-31 | Kremers-Urban Company | Method of treating hepatitis B infection |
US5334395A (en) * | 1988-08-04 | 1994-08-02 | Kremers-Urban Company | Method of treating an epstein-barr viral infection |
EP0450492A1 (en) * | 1990-04-06 | 1991-10-09 | Tosoh Corporation | Alkylxanthate, production thereof, photopolymerization initiator, and polymerization employing the same |
AU4159596A (en) * | 1994-11-14 | 1996-06-06 | Ct-Holding Sa | Antiviral and antitumor pharmaceutical compositions |
DE10117728A1 (de) * | 2001-04-09 | 2002-10-17 | Biosphings Ag | Pharmazeutische Formulierungen für Xanthogenate |
DE10156617A1 (de) * | 2001-11-17 | 2003-05-28 | Biosphings Ag | Herstellung reiner Stereoisomere von Tricyclo[5.2.1.0··2··.··6··]-dec-9-yl-xanthogenat und Arzneimittel daraus |
EP1391221A1 (en) * | 2002-08-23 | 2004-02-25 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | A pharmaceutical preparation containing palladium complex compounds and the uses thereof for treating cancer and autoimmune disease |
DE10343365A1 (de) * | 2003-09-17 | 2005-04-14 | Biosphings Ag | Pharmazeutische Formulierungen von Xanthogenaten und Hemmstoffen der viralen Nukleinsäurereplikation |
DE102005031265A1 (de) * | 2005-07-05 | 2007-01-18 | Sms Demag Ag | Spreizbarer Haspeldorn |
DE102006014390A1 (de) * | 2006-03-29 | 2007-10-04 | Biosphings Ag | Assoziate von Xanthogenaten mit Cyclodextrinen und ihre Verwendung |
EP2176218A2 (en) * | 2007-07-03 | 2010-04-21 | Lumavita AG | Stereoisomers of tricyclodecan-9-yl-xanthogenate |
RU2515986C2 (ru) * | 2008-07-15 | 2014-05-20 | Басф Се | Способ очистки диалкилсульфидов |
US20100221809A1 (en) * | 2008-12-23 | 2010-09-02 | The Regents Of The University Of California | Compositions and Methods for the Isolation of Biologically Active Proteins |
CN114478339B (zh) * | 2022-02-14 | 2023-12-08 | 中南大学 | 一种黄原酸盐类捕收剂的制备方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1854525A (en) * | 1929-11-11 | 1932-04-19 | Shell Dev | Tertiary xanthates |
US1886587A (en) * | 1930-01-09 | 1932-11-08 | Hercules Powder Co Ltd | Method of preparing xanthates of terpene alcohols |
US2037718A (en) * | 1932-11-09 | 1936-04-21 | Du Pont | Xanthates and method of making same |
US2037717A (en) * | 1932-11-09 | 1936-04-21 | Du Pont | Xanthates and method of making same |
FR790353A (fr) * | 1934-05-22 | 1935-11-20 | Bataafsche Petroleum | Préparation de xanthates |
US2161584A (en) * | 1936-08-01 | 1939-06-06 | Socony Vacuum Oil Co Inc | Petroleum lubricant composition |
US2811432A (en) * | 1953-07-17 | 1957-10-29 | Monsanto Chemicals | Herbicidal composition |
US3864469A (en) * | 1967-12-16 | 1975-02-04 | Hoechst Ag | Xanthines in pharmaceutical preparations and for stabilization of vitamins |
US3864417A (en) * | 1970-01-16 | 1975-02-04 | Chevron Res | Saturated hydrocarbon disproportionation at low temperatures |
ZA715615B (en) * | 1970-10-05 | 1972-04-26 | American Cyanamid Co | Manufacture of alkali metal xanthates |
US3965137A (en) * | 1974-05-02 | 1976-06-22 | Stauffer Chemical Company | Thiocyano xanthates |
KR870001238B1 (ko) * | 1980-11-26 | 1987-06-26 | 메르츠+캄패니 게엠베하 앤드 캄패니 | 크산틴산염의 제조방법 |
-
1981
- 1981-11-24 KR KR1019810004542A patent/KR870001238B1/ko not_active Expired
- 1981-11-24 DK DK522081A patent/DK170068B1/da not_active IP Right Cessation
- 1981-11-24 AR AR287572A patent/AR230264A1/es active
- 1981-11-25 CA CA000390861A patent/CA1175047A/en not_active Expired
- 1981-11-25 FR FR8122055A patent/FR2494689B1/fr not_active Expired
- 1981-11-25 BE BE0/206650A patent/BE891245A/fr not_active IP Right Cessation
- 1981-11-25 GB GB8135536A patent/GB2091244B/en not_active Expired
- 1981-11-25 NL NL8105326A patent/NL8105326A/nl not_active Application Discontinuation
- 1981-11-25 PL PL1981233966A patent/PL129383B1/pl unknown
- 1981-11-25 ES ES507430A patent/ES507430A0/es active Granted
- 1981-11-25 IE IE2768/81A patent/IE51944B1/en not_active IP Right Cessation
- 1981-11-25 HU HU813521A patent/HU187476B/hu not_active IP Right Cessation
- 1981-11-25 DE DE3146772A patent/DE3146772C2/de not_active Expired - Fee Related
- 1981-11-25 SE SE8107022A patent/SE450251B/sv not_active IP Right Cessation
- 1981-11-26 CH CH7576/81A patent/CH651546A5/de not_active IP Right Cessation
- 1981-11-26 YU YU2782/81A patent/YU42120B/xx unknown
- 1981-11-26 AT AT0510181A patent/AT376202B/de not_active IP Right Cessation
- 1981-11-26 LU LU83795A patent/LU83795A1/fr unknown
- 1981-11-26 AU AU77928/81A patent/AU549653B2/en not_active Ceased
- 1981-11-26 IT IT25291/81A patent/IT1195297B/it active
- 1981-11-26 JP JP56188502A patent/JPS5943944B2/ja not_active Expired
- 1981-11-26 GR GR66624A patent/GR76308B/el unknown
-
1983
- 1983-05-13 US US06/494,393 patent/US4602037A/en not_active Expired - Fee Related
- 1983-05-24 JP JP58091411A patent/JPS591416A/ja active Granted
-
1985
- 1985-04-22 SG SG292/85A patent/SG29285G/en unknown
-
1989
- 1989-12-29 US US07/458,889 patent/US4981869A/en not_active Expired - Fee Related
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
LU83795A1 (fr) | Xanthates,leur preparation et leur utilisation | |
FR2532844A1 (fr) | Composition pharmaceutique contenant un compose polyprenylique | |
EP0087378B1 (fr) | Ethers-oximes d'alcoylaminoalcools comme médicaments, produits nouveaux et procédés pour leur préparation | |
CA1216859A (fr) | Procede de preparation de nouveaux derives de l'acide 4-phenyl 4-oxo buten-2-oique | |
CH661661A5 (fr) | Agent antineoplasique. | |
FR2481271A1 (fr) | Derives de la nonaprenylamine, leurs sels acides d'addition et leur utilisation dans des compositions pharmaceutiques | |
WO1990006931A1 (fr) | Composes organometalliques, leurs modes de preparation et compositions pharmaceutiques les contenant | |
EP1268470B1 (fr) | Molecules duales contenant un derive peroxydique, leur synthese et leurs applications therapeutiques | |
FR2492821A1 (fr) | Derives de la pyrimidine, leur procede de preparation et les compositions pharmaceutiques les contenant | |
CA1174978A (en) | Xanthates | |
KR20020043249A (ko) | 염증 치료용 6-메톡시-2-나프틸아세트산 전구약물 | |
EP0022017A1 (fr) | Nouveaux dérivés de benzoyl-2 nitro-4 anilides, leur préparation et leur application en tant que médicaments | |
EP0008269B1 (fr) | Nouveaux médicaments contenant, à titre de substance active, des composés de type benzènesulfone, nouveaux composés de ce type et procédé pour leur préparation | |
EP0002635A1 (fr) | Procédé de préparation de dérivés de thiéno (2,3-c) et (3,2-c) pyridines, nouveaux dérivés de la thiéno (2,3-c) pyridine obtenus et leur application thérapeutique | |
EP0482993A1 (fr) | Dérivés N,O spirocycliques de cyclotriphosphazènes, leur préparation et leur application en thérapeutique | |
EP0002638B1 (fr) | Sels d'addition d'aralkylamines subsituées et composition thérapeutique les contenant | |
FR2517672A1 (fr) | Thioalcanoyl-carnitines, procede pour leur preparation et composition pharmaceutique les contenant | |
CH646146A5 (fr) | Derive du 1alpha,25-dihydroxy cholecalciferol et son procede de preparation. | |
CH642961A5 (fr) | Beta-lactones derivees de l'acide 2-hydroxy cyclopentane carboxylique, leurs procedes de preparation et les compositions pharmaceutiques les renfermant. | |
FR1450548A (fr) | Nouveaux dérivés polyhydroxylés des benzimidazoles | |
EP0210886B1 (fr) | Alcools tertiaires halogéno biphéniles utiles en thérapeutique dans le traitement de l'athérosclérose | |
EP0039294B1 (fr) | Bis (phénoxyacétates substitués) de N-alkyl-dialcanolamines, procédé d'obtention, et compositions pharmaceutiques les contenant | |
FR2479812A1 (fr) | Cycloalcoyl propanol amines utiles comme medicaments et procede pour leur preparation | |
FR2508907A1 (fr) | Esters d'hydroxybenzenes substitues de 2-thenoylmercaptopropionylglycine utiles notamment comme mucolytiques, procede pour leur preparation et compositions pharmaceutiques les contenant | |
EP0226475A1 (fr) | Nouveaux dérivés de la diphénoxyethylamine, leur procédé d'obtention et les compositions pharmaceutiques en renfermant |