CA1223879A - Process for the production of amino-dicarboxylic acid-bivalent metal-halogen complexes and novel such complexes - Google Patents
Process for the production of amino-dicarboxylic acid-bivalent metal-halogen complexes and novel such complexesInfo
- Publication number
- CA1223879A CA1223879A CA000438286A CA438286A CA1223879A CA 1223879 A CA1223879 A CA 1223879A CA 000438286 A CA000438286 A CA 000438286A CA 438286 A CA438286 A CA 438286A CA 1223879 A CA1223879 A CA 1223879A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- bivalent metal
- chloride
- ions
- magnesium
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 60
- 229910052736 halogen Inorganic materials 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 239000012736 aqueous medium Substances 0.000 claims abstract description 30
- 239000002184 metal Substances 0.000 claims abstract description 30
- 229910052751 metal Inorganic materials 0.000 claims abstract description 29
- -1 halogen ion Chemical class 0.000 claims abstract description 24
- 150000004820 halides Chemical class 0.000 claims abstract description 18
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 16
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 15
- 150000002500 ions Chemical class 0.000 claims abstract description 10
- 150000002366 halogen compounds Chemical class 0.000 claims abstract description 9
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 8
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 8
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 21
- 239000011777 magnesium Substances 0.000 claims description 17
- 239000011575 calcium Substances 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
- 229910052749 magnesium Inorganic materials 0.000 claims description 15
- 229940091250 magnesium supplement Drugs 0.000 claims description 15
- 229910052712 strontium Inorganic materials 0.000 claims description 15
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 15
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 14
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 14
- 229960005261 aspartic acid Drugs 0.000 claims description 14
- 229910052791 calcium Inorganic materials 0.000 claims description 14
- 239000011572 manganese Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052788 barium Inorganic materials 0.000 claims description 13
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052748 manganese Inorganic materials 0.000 claims description 10
- 239000011701 zinc Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 9
- 235000003704 aspartic acid Nutrition 0.000 claims description 9
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000010941 cobalt Substances 0.000 claims description 8
- 229910017052 cobalt Inorganic materials 0.000 claims description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 238000001694 spray drying Methods 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 229940009098 aspartate Drugs 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 5
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 5
- 239000000395 magnesium oxide Substances 0.000 claims description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 5
- QYOBXHXZJRPWDE-JIZZDEOASA-L magnesium;(2s)-2-amino-4-hydroxy-4-oxobutanoate;chloride Chemical compound [Mg+2].Cl.[O-]C(=O)[C@@H](N)CC([O-])=O QYOBXHXZJRPWDE-JIZZDEOASA-L 0.000 claims description 5
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 4
- 229910001626 barium chloride Inorganic materials 0.000 claims description 4
- 229960002989 glutamic acid Drugs 0.000 claims description 4
- 229940062776 zinc aspartate Drugs 0.000 claims description 4
- POEVDIARYKIEGF-CEOVSRFSSA-L zinc;(2s)-2-aminobutanedioate;hydron Chemical compound [Zn+2].[O-]C(=O)[C@@H](N)CC(O)=O.[O-]C(=O)[C@@H](N)CC(O)=O POEVDIARYKIEGF-CEOVSRFSSA-L 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229940034055 calcium aspartate Drugs 0.000 claims description 3
- 229910001622 calcium bromide Inorganic materials 0.000 claims description 3
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 3
- 150000002681 magnesium compounds Chemical class 0.000 claims description 3
- IMSNBENJLMCAJL-QTNFYWBSSA-L magnesium;(2s)-2-aminopentanedioate;hydrobromide Chemical compound [Mg+2].Br.[O-]C(=O)[C@@H](N)CCC([O-])=O IMSNBENJLMCAJL-QTNFYWBSSA-L 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001553 barium compounds Chemical class 0.000 claims description 2
- 229940049906 glutamate Drugs 0.000 claims description 2
- 229930195712 glutamate Natural products 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- 239000011656 manganese carbonate Substances 0.000 claims description 2
- 235000006748 manganese carbonate Nutrition 0.000 claims description 2
- 229940093474 manganese carbonate Drugs 0.000 claims description 2
- 150000002697 manganese compounds Chemical class 0.000 claims description 2
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 claims description 2
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- QLTGEMIEWNAURK-DKWTVANSSA-L (2s)-2-aminobutanedioate;barium(2+) Chemical compound [Ba+2].[O-]C(=O)[C@@H](N)CC([O-])=O QLTGEMIEWNAURK-DKWTVANSSA-L 0.000 claims 2
- KKPUODLFBBWJPH-DKWTVANSSA-L (2s)-2-aminobutanedioate;iron(2+) Chemical compound [Fe+2].[O-]C(=O)[C@@H](N)CC([O-])=O KKPUODLFBBWJPH-DKWTVANSSA-L 0.000 claims 2
- MWWMZNITXBJVSP-DKWTVANSSA-L (2s)-2-aminobutanedioate;manganese(2+) Chemical compound [Mn+2].[O-]C(=O)[C@@H](N)CC([O-])=O MWWMZNITXBJVSP-DKWTVANSSA-L 0.000 claims 2
- OPSXJNAGCGVGOG-DKWTVANSSA-L Calcium L-aspartate Chemical compound [Ca+2].[O-]C(=O)[C@@H](N)CC([O-])=O OPSXJNAGCGVGOG-DKWTVANSSA-L 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims 2
- 229910001623 magnesium bromide Inorganic materials 0.000 claims 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims 2
- 239000001095 magnesium carbonate Substances 0.000 claims 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 2
- 239000000347 magnesium hydroxide Substances 0.000 claims 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 2
- 229910001425 magnesium ion Inorganic materials 0.000 claims 2
- 229940038584 manganese aspartate Drugs 0.000 claims 2
- 239000011565 manganese chloride Substances 0.000 claims 2
- 235000002867 manganese chloride Nutrition 0.000 claims 2
- 229940099607 manganese chloride Drugs 0.000 claims 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims 1
- 229910001863 barium hydroxide Inorganic materials 0.000 claims 1
- 229910001422 barium ion Inorganic materials 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 229940043430 calcium compound Drugs 0.000 claims 1
- 150000001674 calcium compounds Chemical class 0.000 claims 1
- 229910001424 calcium ion Inorganic materials 0.000 claims 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 1
- 239000000292 calcium oxide Substances 0.000 claims 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims 1
- RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229940102223 injectable solution Drugs 0.000 claims 1
- 150000002506 iron compounds Chemical class 0.000 claims 1
- 235000014413 iron hydroxide Nutrition 0.000 claims 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 claims 1
- IPJKJLXEVHOKSE-UHFFFAOYSA-L manganese dihydroxide Chemical compound [OH-].[OH-].[Mn+2] IPJKJLXEVHOKSE-UHFFFAOYSA-L 0.000 claims 1
- 229910001437 manganese ion Inorganic materials 0.000 claims 1
- 239000011667 zinc carbonate Substances 0.000 claims 1
- 235000004416 zinc carbonate Nutrition 0.000 claims 1
- 229910000010 zinc carbonate Inorganic materials 0.000 claims 1
- 150000003752 zinc compounds Chemical class 0.000 claims 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims 1
- 229940007718 zinc hydroxide Drugs 0.000 claims 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 description 55
- 239000000843 powder Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 229960005069 calcium Drugs 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000002421 anti-septic effect Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 229940064004 antiseptic throat preparations Drugs 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 229940065285 cadmium compound Drugs 0.000 description 2
- 229940095643 calcium hydroxide Drugs 0.000 description 2
- LUUAAIHWKUJNKC-JIZZDEOASA-L calcium;(2s)-2-aminobutanedioate;hydrochloride Chemical compound Cl.[Ca+2].[O-]C(=O)[C@@H](N)CC([O-])=O LUUAAIHWKUJNKC-JIZZDEOASA-L 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000003437 strontium Chemical class 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- GYUKEMYHXWICKF-DKWTVANSSA-N (2s)-2-aminobutanedioic acid;calcium Chemical compound [Ca].OC(=O)[C@@H](N)CC(O)=O GYUKEMYHXWICKF-DKWTVANSSA-N 0.000 description 1
- DWHMPBALQYTJFJ-DKWTVANSSA-N (2s)-2-aminobutanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CC(O)=O DWHMPBALQYTJFJ-DKWTVANSSA-N 0.000 description 1
- 206010021027 Hypomagnesaemia Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 208000015710 Iron-Deficiency Anemia Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000425347 Phyla <beetle> Species 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 208000007502 anemia Diseases 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
- 239000003173 antianemic agent Substances 0.000 description 1
- 239000003212 astringent agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000001662 cadmium compounds Chemical class 0.000 description 1
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- LGLXXNHIGIJYQQ-UHFFFAOYSA-L magnesium;dibromide;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Br-].[Br-] LGLXXNHIGIJYQQ-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 230000001543 purgative effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- 150000003438 strontium compounds Chemical class 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3238118.2-42 | 1982-10-14 | ||
| DE19823238118 DE3238118A1 (de) | 1982-10-14 | 1982-10-14 | Verfahren zur herstellung von komplexverbindungen aus aminodicarbonsaeuren, zweiwertigen metallionen und halogenidionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1223879A true CA1223879A (en) | 1987-07-07 |
Family
ID=6175723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000438286A Expired CA1223879A (en) | 1982-10-14 | 1983-10-04 | Process for the production of amino-dicarboxylic acid-bivalent metal-halogen complexes and novel such complexes |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4546195A (https=) |
| EP (1) | EP0108937B1 (https=) |
| AT (1) | ATE40350T1 (https=) |
| AU (1) | AU576736B2 (https=) |
| CA (1) | CA1223879A (https=) |
| DE (2) | DE3238118A1 (https=) |
| PT (1) | PT77498B (https=) |
| ZA (1) | ZA837455B (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764633A (en) * | 1987-08-31 | 1988-08-16 | Zinpro Corporation | Ferric ion catalyzed complexation of zinc and/or manganese with alpha amino acids |
| DE3809625A1 (de) * | 1988-03-22 | 1989-10-05 | Verla Pharm | Oral verabreichbares pharmazeutisches mittel, insbesondere zur eisen- und magnesiumsubstitutionstherapie |
| DE3814856A1 (de) * | 1988-05-02 | 1989-11-16 | Verla Pharm | Mittel zur prophylaxe des herzinfarkts und zur verhuetung des reinfarkts |
| FR2660653B1 (fr) * | 1990-04-05 | 1994-05-20 | Mayoly Spindler Lab | Sels equimolaires d'acide alpha-amine dicarboxylique et de metal divalent, leur procede de preparation et leur application pour l'obtention de compositions pharmaceutiques. |
| CN1297209C (zh) * | 2003-11-27 | 2007-01-31 | 中国科学院长春应用化学研究所 | 系列复合锌稀土配合物鱼饵料添加剂及其制备方法 |
| EP1627879B1 (de) * | 2004-08-20 | 2006-10-18 | Verla-Pharm Arzneimittelfabrik Apotheker H.J. von Ehrlich GmbH & Co. KG | Verfahren zur Herstellung von bestimmten Hydrohalogenid-Metallkomplexverbindungen mit spezifischer grobkörniger Struktur |
| US7523563B2 (en) | 2005-08-18 | 2009-04-28 | Verla-Pharm Arzneimittelfabrik Apotheker H.J.V. Ehrlich Gmbh & Co. Kg | Process for preparing certain hydrohalide metal complex compounds having a specific coarse structure |
| CA2571645A1 (en) | 2006-12-19 | 2008-06-19 | Apotex Technologies Inc. | Pharmaceutically acceptable salts of thymodepressin and processes for their manufacture |
| JP6211521B2 (ja) | 2011-09-08 | 2017-10-11 | マイクロニュートリエンツ ユー・エス・エー エル・エル・シーＭｉｃｒｏｎｕｔｒｉｅｎｔｓ ＵＳＡ ＬＬＣ | 微量栄養素補助食品 |
| US9901523B2 (en) | 2012-12-19 | 2018-02-27 | Colgate-Palmolive Company | Oral care products comprising zinc oxide and trimethylglycine |
| US9925130B2 (en) * | 2012-12-19 | 2018-03-27 | Colgate-Palmolive Company | Composition with zinc amino acid/trimethylglycine halide precursors |
| US9750670B2 (en) | 2012-12-19 | 2017-09-05 | Colgate-Palmolive Company | Zinc amino acid complex with cysteine |
| WO2014098828A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Teeth whitening methods, visually perceptible signals and compositions therefor|comprising zinc amino acid halides |
| EP2934444B1 (en) | 2012-12-19 | 2016-11-30 | Colgate-Palmolive Company | Oral care products comprising tetrabasic zinc chloride and trimethylglycine |
| EP2934696B1 (en) * | 2012-12-19 | 2017-07-26 | Colgate-Palmolive Company | Zinc amino acid halide complex with cysteine |
| EP2934438B1 (en) | 2012-12-19 | 2017-02-15 | Colgate-Palmolive Company | Zinc amino acid/trimethylglycine halide |
| MX353216B (es) | 2012-12-19 | 2018-01-08 | Colgate Palmolive Co | Productos antitranspirantes con proteinas y sales antitranspirantes. |
| US9504858B2 (en) | 2012-12-19 | 2016-11-29 | Colgate-Palmolive Company | Zinc amino acid halide complex with cysteine |
| US10188112B2 (en) | 2012-12-19 | 2019-01-29 | Colgate-Palmolive Company | Personal cleansing compositions containing zinc amino acid/trimethylglycine halide |
| AU2012397265B2 (en) | 2012-12-19 | 2016-02-25 | Colgate-Palmolive Company | Oral gel comprising zinc - amino acid complex |
| US9675823B2 (en) | 2012-12-19 | 2017-06-13 | Colgate-Palmolive Company | Two component compositions containing zinc amino acid halide complexes and cysteine |
| KR20150097494A (ko) | 2012-12-19 | 2015-08-26 | 콜게이트-파아므올리브캄파니 | 4 염기성 아연 아미노산 할로겐화물 착물을 포함하는 구강 관리 제품 |
| CN107308013A (zh) | 2012-12-19 | 2017-11-03 | 高露洁-棕榄公司 | 锌‑赖氨酸络合物 |
| WO2014098826A1 (en) * | 2012-12-19 | 2014-06-26 | Colgate-Palmolive Company | Oral care compositions comprising zinc amino acid halides |
| RU2648513C2 (ru) * | 2012-12-19 | 2018-03-26 | Колгейт-Палмолив Компани | Ополаскиватель для полости рта с галогенидом цинка-аминокислоты |
| US9498421B2 (en) | 2012-12-19 | 2016-11-22 | Colgate-Palmolive Company | Two component compositions containing tetrabasic zinc-amino acid halide complexes and cysteine |
| CN103739509B (zh) * | 2014-01-09 | 2015-12-30 | 山东祥维斯生物科技股份有限公司 | 一种甘氨酸螯合锰的工业化生产制备工艺 |
| US9669056B2 (en) | 2014-05-16 | 2017-06-06 | Micronutrients Usa Llc | Micronutrient supplement made from copper metal |
| CN105712895A (zh) * | 2014-12-04 | 2016-06-29 | 辽宁药联制药有限公司 | 盐酸门冬氨酸镁三水合物的制备方法 |
| CN106883135A (zh) * | 2015-12-16 | 2017-06-23 | 辽宁药联制药有限公司 | 一种制备盐酸门冬氨酸镁原料药的方法 |
| CN106916075A (zh) * | 2015-12-24 | 2017-07-04 | 辽宁药联制药有限公司 | 一种盐酸门冬氨酸镁原料药的制备方法 |
| US11091502B2 (en) | 2018-12-21 | 2021-08-17 | Colgate-Palmolive Company | Methods for synthesizing zinc-lysine-chloride complex |
| US11229591B2 (en) | 2018-12-21 | 2022-01-25 | Colgate-Palmolive Company | Methods for synthesizing zinc-lysine-chloride complex |
| WO2020131665A1 (en) | 2018-12-21 | 2020-06-25 | Colgate-Palmolive Company | Zinc-arginine-halide complex |
| US11117906B2 (en) | 2018-12-21 | 2021-09-14 | Colgate-Palmolive Company | Methods for synthesizing zinc-lysine-chloride complex |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE357754C (de) * | 1919-08-08 | 1922-08-31 | Farbenfab Vorm Bayer F & Co | Verfahren zur Darstellung von Doppelverbindungen aus aliphatischen Aminodicarbonsaeuren |
| BE535350A (https=) * | 1954-02-01 | |||
| US2996490A (en) * | 1959-05-12 | 1961-08-15 | Firestone Tire & Rubber Co | Suspension polymerization process and novel compounds for use in said process |
| US3836668A (en) * | 1960-12-27 | 1974-09-17 | Ferrer Labor | Therapeutic composition and method of treating patients therewith |
| NL128181C (https=) * | 1964-01-06 | |||
| DE1809120A1 (de) * | 1968-11-15 | 1970-06-11 | Verla Pharm | Magnesiummonoasparathydrojodid |
| DE1809118A1 (de) * | 1968-11-15 | 1970-06-04 | Verla Pharm Ph Mr H Josef V Eh | Magnesiummonoaspartathydrofluorid |
| DE1809119C3 (de) * | 1968-11-15 | 1973-12-20 | Verla-Pharm Arzneimittelfabrik, Apotheker H.J.V.Ehrlich, 8132 Tutzing | Infarktprophylaktikum |
| DE1809121C3 (de) * | 1968-11-15 | 1978-04-27 | Verla-Pharm. Arzneimittelfabrik, Apotheker H.J.V. Ehrlich, 8132 Tutzing | Magnesiummonoaspartat-Hydrobromid und dieses enthaltende Arzneimittel |
| GB1283810A (en) * | 1970-12-30 | 1972-08-02 | Verla Pharm | Magnesium aspartate hydrohalides |
| DE2228101C3 (de) * | 1972-06-09 | 1979-07-05 | Verla-Pharm. Arzneimittelfabrik, Apotheker H.J. V. Ehrlich, Gmbh & Co Kg, 8132 Tutzing | Verfahren zur Gewinnung von Komplexverbindungen aus Aminodicarbonsäureionen, Magnesiumionen und Halogenidionen |
| US3950372A (en) * | 1974-07-03 | 1976-04-13 | Zinpro Corporation | 1:1 Manganese alpha amino acid complexes |
| US4137326A (en) * | 1975-04-11 | 1979-01-30 | Verla-Pharm Arzneimittelfabrik, Apotheker H.J.V. Ehrlich | Use of magnesium monospartate hydrochloride complex |
| DE2752287C3 (de) * | 1977-11-23 | 1980-06-26 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Gewinnung von Salzen der Asparaginsäure |
-
1982
- 1982-10-14 DE DE19823238118 patent/DE3238118A1/de active Granted
-
1983
- 1983-10-04 CA CA000438286A patent/CA1223879A/en not_active Expired
- 1983-10-05 ZA ZA837455A patent/ZA837455B/xx unknown
- 1983-10-11 US US06/540,644 patent/US4546195A/en not_active Expired - Fee Related
- 1983-10-12 AU AU20109/83A patent/AU576736B2/en not_active Ceased
- 1983-10-13 PT PT77498A patent/PT77498B/pt not_active IP Right Cessation
- 1983-10-13 EP EP83110226A patent/EP0108937B1/en not_active Expired
- 1983-10-13 AT AT83110226T patent/ATE40350T1/de not_active IP Right Cessation
- 1983-10-13 DE DE8383110226T patent/DE3379041D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU576736B2 (en) | 1988-09-08 |
| PT77498A (en) | 1983-11-01 |
| DE3379041D1 (en) | 1989-03-02 |
| DE3238118C2 (https=) | 1988-07-28 |
| DE3238118A1 (de) | 1984-04-19 |
| PT77498B (en) | 1986-02-12 |
| EP0108937B1 (en) | 1989-01-25 |
| EP0108937A3 (en) | 1984-09-26 |
| ZA837455B (en) | 1984-06-27 |
| US4546195A (en) | 1985-10-08 |
| ATE40350T1 (de) | 1989-02-15 |
| EP0108937A2 (en) | 1984-05-23 |
| AU2010983A (en) | 1984-04-19 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |