DD201685A5 - Verfahren zur herstellung von alkanol-phosphorsaeureammoniumalkylestern - Google Patents
Verfahren zur herstellung von alkanol-phosphorsaeureammoniumalkylestern Download PDFInfo
- Publication number
- DD201685A5 DD201685A5 DD81234206A DD23420681A DD201685A5 DD 201685 A5 DD201685 A5 DD 201685A5 DD 81234206 A DD81234206 A DD 81234206A DD 23420681 A DD23420681 A DD 23420681A DD 201685 A5 DD201685 A5 DD 201685A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- propanol
- phosphoric acid
- mono
- yield
- chain
- Prior art date
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- 150000002148 esters Chemical class 0.000 title description 30
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 239000011593 sulfur Substances 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 5
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 -alkyl-mercapto Chemical group 0.000 claims description 259
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 110
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 94
- 239000002253 acid Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 150000003904 phospholipids Chemical class 0.000 abstract description 3
- 201000011510 cancer Diseases 0.000 abstract description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 2
- 229960001231 choline Drugs 0.000 description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
- 239000000126 substance Substances 0.000 description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 239000007858 starting material Substances 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 238000002425 crystallisation Methods 0.000 description 33
- 230000008025 crystallization Effects 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 238000000354 decomposition reaction Methods 0.000 description 27
- 238000005245 sintering Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000012280 lithium aluminium hydride Substances 0.000 description 21
- 159000000000 sodium salts Chemical class 0.000 description 19
- 239000013078 crystal Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- 125000003396 thiol group Chemical class [H]S* 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 15
- 239000012362 glacial acetic acid Substances 0.000 description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 15
- 230000008018 melting Effects 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 14
- VEGWBAFKBVVZMP-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)SC(CCCS)C Chemical compound C(CCCCCCCCCCCCCCCCC)SC(CCCS)C VEGWBAFKBVVZMP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 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 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 12
- 229940071536 silver acetate Drugs 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 229940077388 benzenesulfonate Drugs 0.000 description 11
- WXWYBXRUMMKGRJ-UHFFFAOYSA-N (3-hydroxy-2-methoxypropyl) benzenesulfonate Chemical compound COC(CO)COS(=O)(=O)C1=CC=CC=C1 WXWYBXRUMMKGRJ-UHFFFAOYSA-N 0.000 description 10
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 10
- 238000006366 phosphorylation reaction Methods 0.000 description 10
- 230000009467 reduction Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000026731 phosphorylation Effects 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 7
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- AEUVIXACNOXTBX-UHFFFAOYSA-N 1-sulfanylpropan-1-ol Chemical compound CCC(O)S AEUVIXACNOXTBX-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- LPPJNZJBKFSQGA-UHFFFAOYSA-M hydron;2-hydroxyethyl(trimethyl)azanium;phosphate Chemical compound OP(O)([O-])=O.C[N+](C)(C)CCO LPPJNZJBKFSQGA-UHFFFAOYSA-M 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- ZJCZFAAXZODMQT-UHFFFAOYSA-N 2-methylpentadecane-2-thiol Chemical compound CCCCCCCCCCCCCC(C)(C)S ZJCZFAAXZODMQT-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical class CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 description 5
- 150000004682 monohydrates Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 5
- IAQNLUJLASSNLX-UHFFFAOYSA-N 2-bromoethyl dihydrogen phosphate Chemical compound OP(O)(=O)OCCBr IAQNLUJLASSNLX-UHFFFAOYSA-N 0.000 description 4
- MLKJAWRTVVIMAO-UHFFFAOYSA-N 3-octadecylsulfanylpropan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCSCCCO MLKJAWRTVVIMAO-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- JKOTZBXSNOGCIF-UHFFFAOYSA-N 1-bromopentadecane Chemical compound CCCCCCCCCCCCCCCBr JKOTZBXSNOGCIF-UHFFFAOYSA-N 0.000 description 3
- SSSOBLLLFMPUMM-UHFFFAOYSA-N 1-octadecylsulfanylpropan-1-ol Chemical compound C(CCCCCCCCCCCCCCCCC)SC(CC)O SSSOBLLLFMPUMM-UHFFFAOYSA-N 0.000 description 3
- CBMVZTCTLGQLKP-UHFFFAOYSA-N 2-methoxy-3-nonadecan-2-ylsulfanylpropan-1-ol Chemical compound CCCCCCCCCCCCCCCCCC(C)SCC(CO)OC CBMVZTCTLGQLKP-UHFFFAOYSA-N 0.000 description 3
- ZJICKDPTXMNTPU-UHFFFAOYSA-N 2-methoxy-3-octadecylsulfanylpropan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCSCC(CO)OC ZJICKDPTXMNTPU-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KGGCNSPGZLAPDM-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)SC(CCCO)C Chemical compound C(CCCCCCCCCCCCCCCCC)SC(CCCO)C KGGCNSPGZLAPDM-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- IYMAUEAFOBSGCY-UHFFFAOYSA-N benzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.C1=CC=CC=C1 IYMAUEAFOBSGCY-UHFFFAOYSA-N 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JZLONOOYIXEAHM-UHFFFAOYSA-N methyl 2-fluoro-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC=C1F JZLONOOYIXEAHM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KKLFAZSAQYFWPV-UHFFFAOYSA-N 1-dodecylsulfanylpropan-1-ol Chemical compound CCCCCCCCCCCCSC(O)CC KKLFAZSAQYFWPV-UHFFFAOYSA-N 0.000 description 2
- DRQMVFSJPNUWGM-UHFFFAOYSA-N 2-(hexadecylsulfanylmethyl)-3-methoxypropan-1-ol Chemical compound CCCCCCCCCCCCCCCCSCC(CO)COC DRQMVFSJPNUWGM-UHFFFAOYSA-N 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- WFIDKOJNXWINJX-UHFFFAOYSA-N 2-hexadecoxy-3-methylsulfanylpropan-1-ol Chemical compound CCCCCCCCCCCCCCCCOC(CO)CSC WFIDKOJNXWINJX-UHFFFAOYSA-N 0.000 description 2
- HILBEBRBIDFNOI-UHFFFAOYSA-N 3-(2-methoxyoctadecylsulfanyl)propan-1-ol Chemical compound CCCCCCCCCCCCCCCCC(OC)CSCCCO HILBEBRBIDFNOI-UHFFFAOYSA-N 0.000 description 2
- OJBDCVCTGOXOFN-UHFFFAOYSA-N 3-hexadecylsulfanyl-2-methylpropan-1-ol Chemical compound CCCCCCCCCCCCCCCCSCC(C)CO OJBDCVCTGOXOFN-UHFFFAOYSA-N 0.000 description 2
- ZNVBMQIWZIDDCS-UHFFFAOYSA-N 3-octadecoxypropan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCOCCCO ZNVBMQIWZIDDCS-UHFFFAOYSA-N 0.000 description 2
- WEWSWGPLIUWVLF-UHFFFAOYSA-N 3-octadecylsulfanylbutan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCSC(C)CCO WEWSWGPLIUWVLF-UHFFFAOYSA-N 0.000 description 2
- YUKWYOPEDMUTHZ-UHFFFAOYSA-N 3-pentadecylsulfanylpropan-1-ol Chemical compound CCCCCCCCCCCCCCCSCCCO YUKWYOPEDMUTHZ-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 230000003327 cancerostatic effect Effects 0.000 description 2
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
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- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- KZJZFUHYAZHJJA-UHFFFAOYSA-N sodium;hexan-1-olate Chemical compound [Na+].CCCCCC[O-] KZJZFUHYAZHJJA-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical class SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803039629 DE3039629A1 (de) | 1980-10-21 | 1980-10-21 | Neue schwefelhaltige phospholipide, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE19813118965 DE3118965A1 (de) | 1981-05-13 | 1981-05-13 | Neue schwefelhaltige phospholipide, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD201685A5 true DD201685A5 (de) | 1983-08-03 |
Family
ID=25788614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81234206A DD201685A5 (de) | 1980-10-21 | 1981-10-19 | Verfahren zur herstellung von alkanol-phosphorsaeureammoniumalkylestern |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4444766A (xx) |
| EP (1) | EP0050327B1 (xx) |
| CA (1) | CA1174244A (xx) |
| DD (1) | DD201685A5 (xx) |
| DE (1) | DE3164332D1 (xx) |
| ES (1) | ES506386A0 (xx) |
| HK (1) | HK68987A (xx) |
| HU (1) | HU186789B (xx) |
| SG (1) | SG22187G (xx) |
| SU (2) | SU1241994A3 (xx) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3127503A1 (de) * | 1981-07-11 | 1983-02-17 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue phospholipide, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| US4981989A (en) * | 1984-12-10 | 1991-01-01 | American Cyanamid Company | Antihypertensive phosphate derivatives and intermediates thereof |
| US4619917A (en) * | 1985-07-18 | 1986-10-28 | Sandoz Pharm. Corp. | Substituted 2-furanyl- or 5-oxo-2-furanyl methoxy phosphoryl alkyl cyclimmonium salts |
| CA2001401A1 (en) * | 1988-10-25 | 1990-04-25 | Claude Piantadosi | Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions |
| DE3906952A1 (de) * | 1989-03-04 | 1990-09-06 | Boehringer Mannheim Gmbh | (3-(c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)6(pfeil abwaerts)-c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)8(pfeil abwaerts))alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl)-(2-trimethylammonio-ethyl) phosphate, verfahren zu deren herstellung diese verbindungen enthaltende arzneimittel |
| DE3929217A1 (de) * | 1989-09-02 | 1991-03-07 | Boehringer Mannheim Gmbh | Verwendung von phospholipid-derivaten als antivirale arzneimittel und neue phospholipide |
| JPH0791301B2 (ja) * | 1989-10-02 | 1995-10-04 | 新日本理化株式会社 | ジアセタールの製造方法 |
| ATE158295T1 (de) * | 1991-07-04 | 1997-10-15 | Asta Medica Ag | Verfahren zur herstellung von alkylphosphocholinen und reinherstellung derselben |
| DE4222910A1 (de) * | 1992-07-11 | 1994-01-13 | Asta Medica Ag | Neue Phospholipidderivate |
| US6172050B1 (en) | 1992-07-11 | 2001-01-09 | Asta Medica Aktiengesellschaft | Phospholipid derivatives |
| WO1994002153A1 (en) * | 1992-07-22 | 1994-02-03 | Boehringer Mannheim Gmbh | Use of sulphur containing phospholipids for treating leishmaniasis |
| US5489580A (en) * | 1992-11-05 | 1996-02-06 | University Of Connecticut | Phospholipid compounds and use therefor |
| AU7044894A (en) * | 1993-06-10 | 1995-01-03 | University Of North Carolina At Chapel Hill, The | (phospho)lipids for combatting hepatitis b virus infection |
| US5610198A (en) * | 1994-03-18 | 1997-03-11 | The United States Of America As Represented By The Department Of Health And Human Services | Anti-mycobacterial compositions and their use for the treatment of tuberculosis and related diseases |
| US5962437A (en) * | 1994-08-29 | 1999-10-05 | Wake Forest University | Lipid analogs for treating viral infections |
| US7135584B2 (en) * | 1995-08-07 | 2006-11-14 | Wake Forest University | Lipid analogs for treating viral infections |
| TW343975B (en) * | 1995-12-15 | 1998-11-01 | Boehringer Mannheim Gmbh | New phospholipid derivatives of phosphonocarboxylic acids, the production thereof as well as their use as antiviral pharmaceutical agents |
| EP0916654B1 (en) * | 1996-08-02 | 2005-02-23 | Kaneka Corporation | Sulfonic ester derivatives, process for preparing the same, and use thereof |
| US7026469B2 (en) * | 2000-10-19 | 2006-04-11 | Wake Forest University School Of Medicine | Compositions and methods of double-targeting virus infections and cancer cells |
| US7309696B2 (en) | 2000-10-19 | 2007-12-18 | Wake Forest University | Compositions and methods for targeting cancer cells |
| US6960738B2 (en) * | 2001-05-29 | 2005-11-01 | Koninklijke Philips Electronics N.V. | Metal-ceramic bond |
| JP4714413B2 (ja) * | 2001-08-31 | 2011-06-29 | トムソン ライセンシング | オーディオビジュアルストリームのためのシーケンスカウンタ |
| US20050187192A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Pharmaceutical Company | Phospholipids for the treatment of infection by togaviruses, herpes viruses and coronaviruses |
| US20050187191A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Louis S. | Methods and compositions for the treatment of respiratory syncytial virus |
| PL2574341T3 (pl) | 2004-03-29 | 2017-09-29 | University Of South Florida | Efektywne leczenie guzów i raka fosforanem tricyrybiny |
| US8642577B2 (en) | 2005-04-08 | 2014-02-04 | Chimerix, Inc. | Compounds, compositions and methods for the treatment of poxvirus infections |
| EP2842559A3 (en) | 2005-04-08 | 2015-03-18 | Chimerix, Inc. | Compounds, compositions and methods for the treatment of viral infections and other medical disorders |
| ES2733353T3 (es) * | 2007-11-09 | 2019-11-28 | Basf As | Compuestos lípidos para uso en productos cosméticos, como suplemento alimenticio o como un medicamento |
| CN102670628B (zh) * | 2008-01-25 | 2015-11-25 | 奇默里克斯公司 | 治疗病毒感染的方法 |
| EP2147910A1 (en) | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
| CA2760877C (en) | 2009-05-08 | 2020-09-08 | Pronova Biopharma Norge As | Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas |
| WO2011011519A1 (en) | 2009-07-21 | 2011-01-27 | Chimerix, Inc. | Compounds, compositions and methods for treating ocular conditions |
| DK2534150T3 (en) | 2010-02-12 | 2017-06-12 | Chimerix Inc | METHODS OF TREATING VIRUS INFECTION |
| WO2011139709A2 (en) | 2010-04-26 | 2011-11-10 | Chimerix, Inc. | Methods of treating retroviral infections and related dosage regimes |
| ES2618604T3 (es) | 2010-11-05 | 2017-06-21 | Pronova Biopharma Norge As | Métodos de tratamiento usando compuestos lipídicos |
| WO2014132134A1 (en) | 2013-02-28 | 2014-09-04 | Pronova Biopharma Norge As | A composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same |
| AU2016256552B2 (en) | 2015-04-28 | 2021-04-01 | Pronova Biopharma Norge As | Use of structurally enhanced fatty acids containing sulphur for preventing and/or treating non-alcoholic steatohepatitis |
| KR20200096791A (ko) | 2017-12-06 | 2020-08-13 | 바스프 에이에스 | 비알콜성 지방간염 치료용 지방산 유도체 |
| LU101206B1 (en) * | 2019-05-06 | 2020-11-06 | Univ Luxembourg | PDEdelta Inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1543937C3 (de) * | 1966-01-14 | 1982-12-09 | Unilever N.V., 3000 Rotterdam | Verwendung modifizierter kephalinhaltiger Phosphatidgemische als Emulgatoren für O/W-Emulsionen und Verfahren zur Herstellung solcher Emulgatoren |
| US4119714A (en) * | 1970-02-27 | 1978-10-10 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E. V. | Glycerin-alkylether-(1)-phosphoric acid-(3)-monocholine esters as enhancers of the natural resistance of the mammalian organism against non-carcinogenic pathogens |
| DE2009341C3 (de) * | 1970-02-27 | 1979-06-21 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | 3-Octadecyloxy-propanol-(l)-phosphorsäure-monocholinester und Verfahren zu dessen Herstellung |
| DE2033359C3 (de) * | 1970-07-06 | 1980-02-14 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | Acylpropandiol-(l,3)-phosphorsäuremono-cholinester und Verfahren zu deren Herstellung |
| US4159988A (en) * | 1974-08-06 | 1979-07-03 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | Synthetic phospholipids, a process for their manufacture and their use |
| DE2619686C2 (de) * | 1976-05-04 | 1986-08-07 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Verwendung eines Lysolecithins zur Tumorbehandlung |
| DE2619715A1 (de) * | 1976-05-04 | 1977-11-24 | Max Planck Gesellschaft | Tumor-antigen und verfahren zu dessen herstellung |
| DE2642661C2 (de) * | 1976-09-22 | 1984-06-28 | A. Nattermann & Cie GmbH, 5000 Köln | Acetoin-dialkyl-phosphorsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| JPS55118494A (en) * | 1979-03-07 | 1980-09-11 | Toyama Chem Co Ltd | Novel phosphorylcholine compound, its preparation, and antitumor agent comprising it |
| US4329302A (en) * | 1980-06-27 | 1982-05-11 | Board Of Regents, The University Of Texas System | Synthetic phosphoglycerides possessing platelet activating properties |
| DE3025804C2 (de) * | 1980-07-08 | 1985-09-05 | A. Nattermann & Cie GmbH, 5000 Köln | 1-S-Alkyl-2-0-acyl-3-phosphocholin-1-mercapto-2,3-propandiole, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
-
1981
- 1981-10-16 DE DE8181108393T patent/DE3164332D1/de not_active Expired
- 1981-10-16 EP EP81108393A patent/EP0050327B1/de not_active Expired
- 1981-10-16 US US06/311,830 patent/US4444766A/en not_active Expired - Lifetime
- 1981-10-19 DD DD81234206A patent/DD201685A5/de unknown
- 1981-10-19 HU HU813039A patent/HU186789B/hu not_active IP Right Cessation
- 1981-10-20 ES ES81506386A patent/ES506386A0/es active Granted
- 1981-10-20 SU SU813347450A patent/SU1241994A3/ru active
- 1981-10-20 CA CA000388309A patent/CA1174244A/en not_active Expired
-
1983
- 1983-04-20 SU SU833578351A patent/SU1376948A3/ru active
-
1987
- 1987-03-04 SG SG221/87A patent/SG22187G/en unknown
- 1987-09-24 HK HK689/87A patent/HK68987A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0050327A1 (de) | 1982-04-28 |
| ES8304147A1 (es) | 1983-03-01 |
| CA1174244A (en) | 1984-09-11 |
| ES506386A0 (es) | 1983-03-01 |
| SU1376948A3 (ru) | 1988-02-23 |
| EP0050327B1 (de) | 1984-06-20 |
| SU1241994A3 (ru) | 1986-06-30 |
| SG22187G (en) | 1987-11-13 |
| HU186789B (en) | 1985-09-30 |
| DE3164332D1 (en) | 1984-07-26 |
| US4444766A (en) | 1984-04-24 |
| HK68987A (en) | 1987-10-02 |
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