HUT73493A - Salts and complexes of n,n`-bis(dicarboxy-methyl)-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadekane derivatives, ad pharmaceutical compositions containing them - Google Patents
Salts and complexes of n,n`-bis(dicarboxy-methyl)-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadekane derivatives, ad pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HUT73493A HUT73493A HU9502769A HU9502769A HUT73493A HU T73493 A HUT73493 A HU T73493A HU 9502769 A HU9502769 A HU 9502769A HU 9502769 A HU9502769 A HU 9502769A HU T73493 A HUT73493 A HU T73493A
- Authority
- HU
- Hungary
- Prior art keywords
- product
- tetraoxa
- salt
- mmol
- metal
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 46
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 239000011734 sodium Substances 0.000 claims description 64
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 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 12
- 229910052791 calcium Inorganic materials 0.000 claims description 9
- 239000011575 calcium Substances 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- KWLHTBMKVJVZRY-UHFFFAOYSA-N 2-[16-(dicarboxymethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propanedioic acid Chemical compound OC(=O)C(C(O)=O)N1CCOCCOCCN(C(C(O)=O)C(O)=O)CCOCCOCC1 KWLHTBMKVJVZRY-UHFFFAOYSA-N 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 abstract description 26
- 229910052712 strontium Inorganic materials 0.000 abstract description 18
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract description 18
- 239000000203 mixture Substances 0.000 abstract description 16
- 229910052751 metal Inorganic materials 0.000 abstract description 15
- 239000002184 metal Substances 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 13
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical class C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 abstract description 12
- 229910052684 Cerium Inorganic materials 0.000 abstract description 5
- 229910021645 metal ion Inorganic materials 0.000 abstract description 3
- 239000013543 active substance Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 238000001990 intravenous administration Methods 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910001428 transition metal ion Inorganic materials 0.000 abstract 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 88
- 235000002639 sodium chloride Nutrition 0.000 description 74
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000000047 product Substances 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000011780 sodium chloride Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 33
- 241001465754 Metazoa Species 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 25
- -1 (dicarboxymethyl) - Chemical class 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 19
- 238000000605 extraction Methods 0.000 description 19
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- VBZOUUJVGADJBK-UHFFFAOYSA-N 2-bromopropanedioic acid Chemical compound OC(=O)C(Br)C(O)=O VBZOUUJVGADJBK-UHFFFAOYSA-N 0.000 description 15
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 14
- 230000014759 maintenance of location Effects 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 11
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229960005069 calcium Drugs 0.000 description 8
- 150000002678 macrocyclic compounds Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 210000004072 lung Anatomy 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 230000000536 complexating effect Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 210000000683 abdominal cavity Anatomy 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 210000000988 bone and bone Anatomy 0.000 description 4
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000002708 enhancing effect Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 235000011148 calcium chloride Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 210000001723 extracellular space Anatomy 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 229940091250 magnesium supplement Drugs 0.000 description 3
- 230000037081 physical activity Effects 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
- JCPUKHWHNNFWDX-UHFFFAOYSA-N 2-(bromomethyl)propanedioic acid Chemical compound OC(=O)C(CBr)C(O)=O JCPUKHWHNNFWDX-UHFFFAOYSA-N 0.000 description 2
- VCSBDMWPFZZEHM-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]propanedioic acid Chemical compound OC(=O)C(C(O)=O)CC1=CC=CC=C1Br VCSBDMWPFZZEHM-UHFFFAOYSA-N 0.000 description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- GXZMZBDZHXMNJB-UHFFFAOYSA-L C(CC(=O)[O-])(=O)OO.[Na+].[Na+].OOC(CC(=O)[O-])=O Chemical compound C(CC(=O)[O-])(=O)OO.[Na+].[Na+].OOC(CC(=O)[O-])=O GXZMZBDZHXMNJB-UHFFFAOYSA-L 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 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 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910001622 calcium bromide Inorganic materials 0.000 description 2
- 229960002713 calcium chloride Drugs 0.000 description 2
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 2
- GWXLDORMOJMVQZ-RNFDNDRNSA-N cerium-144 Chemical compound [144Ce] GWXLDORMOJMVQZ-RNFDNDRNSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 210000002808 connective tissue Anatomy 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- FLZGOLYAPUSSJG-UHFFFAOYSA-N 2-(1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)N1CCOCCOCCNCCOCCOCC1 FLZGOLYAPUSSJG-UHFFFAOYSA-N 0.000 description 1
- KPMAGKCNQVAMKJ-UHFFFAOYSA-N 2-(2-bromoethyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)CCBr KPMAGKCNQVAMKJ-UHFFFAOYSA-N 0.000 description 1
- IKQHTGKUKLHHOY-UHFFFAOYSA-N 2-[16-(dicarboxymethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propanedioic acid;lithium Chemical compound [Li].[Li].[Li].[Li].OC(=O)C(C(O)=O)N1CCOCCOCCN(C(C(O)=O)C(O)=O)CCOCCOCC1 IKQHTGKUKLHHOY-UHFFFAOYSA-N 0.000 description 1
- WBXFLFGMNUTPEK-UHFFFAOYSA-N 2-bromo-3-methoxy-3-oxopropanoic acid Chemical compound COC(=O)C(Br)C(O)=O WBXFLFGMNUTPEK-UHFFFAOYSA-N 0.000 description 1
- VPWLFOOAVIRLEF-UHFFFAOYSA-N 3-hydroperoxy-3-oxopropanoic acid Chemical compound OOC(=O)CC(O)=O VPWLFOOAVIRLEF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical class [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CIOAGBVUUVVLOB-NJFSPNSNSA-N Strontium-90 Chemical compound [90Sr] CIOAGBVUUVVLOB-NJFSPNSNSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001669 calcium Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- PPQPEAAPRXUQES-UHFFFAOYSA-N calcium;2-[16-(dicarboxymethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propanedioic acid Chemical compound [Ca].OC(=O)C(C(O)=O)N1CCOCCOCCN(C(C(O)=O)C(O)=O)CCOCCOCC1 PPQPEAAPRXUQES-UHFFFAOYSA-N 0.000 description 1
- GWXLDORMOJMVQZ-OUBTZVSYSA-N cerium-141 Chemical compound [141Ce] GWXLDORMOJMVQZ-OUBTZVSYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000002739 cryptand Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- IIYNNSHGLFMMRP-UHFFFAOYSA-L disodium;2-hydroxypropanedioate Chemical compound [Na+].[Na+].[O-]C(=O)C(O)C([O-])=O IIYNNSHGLFMMRP-UHFFFAOYSA-L 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 125000000346 malonyl group Chemical group C(CC(=O)*)(=O)* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012857 radioactive material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 150000003437 strontium Chemical class 0.000 description 1
- CIOAGBVUUVVLOB-OUBTZVSYSA-N strontium-89 Chemical compound [89Sr] CIOAGBVUUVVLOB-OUBTZVSYSA-N 0.000 description 1
- 229940006509 strontium-89 Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- ZUUZGQPEQORUEV-UHFFFAOYSA-N tetrahydrate;hydrochloride Chemical compound O.O.O.O.Cl ZUUZGQPEQORUEV-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/08—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and more than one oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Toxicology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU90145A HU210667B (hu) | 1990-01-16 | 1990-01-16 | Eljárás N,N'-bisz(dikarboxi-metil)-1,4,10,13-tetraoxa-7,16-diaza-ciklooktadekán-származékok sói és komplexei és a vegyületeket tartalmazó gyógyászati készítmények előállítására |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU9502769D0 HU9502769D0 (en) | 1995-11-28 |
| HUT73493A true HUT73493A (en) | 1996-08-28 |
Family
ID=10948158
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9502769A HUT73493A (en) | 1990-01-16 | 1990-01-16 | Salts and complexes of n,n`-bis(dicarboxy-methyl)-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadekane derivatives, ad pharmaceutical compositions containing them |
| HU90145A HU210667B (hu) | 1990-01-16 | 1990-01-16 | Eljárás N,N'-bisz(dikarboxi-metil)-1,4,10,13-tetraoxa-7,16-diaza-ciklooktadekán-származékok sói és komplexei és a vegyületeket tartalmazó gyógyászati készítmények előállítására |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU90145A HU210667B (hu) | 1990-01-16 | 1990-01-16 | Eljárás N,N'-bisz(dikarboxi-metil)-1,4,10,13-tetraoxa-7,16-diaza-ciklooktadekán-származékok sói és komplexei és a vegyületeket tartalmazó gyógyászati készítmények előállítására |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0463123A1 (en]) |
| JP (1) | JPH04505626A (en]) |
| KR (1) | KR970009042B1 (en]) |
| AU (1) | AU645507B2 (en]) |
| CA (1) | CA2048627A1 (en]) |
| HU (2) | HUT73493A (en]) |
| IN (1) | IN171733B (en]) |
| RU (1) | RU2060256C1 (en]) |
| UA (1) | UA35547C2 (en]) |
| WO (1) | WO1991010655A1 (en]) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06505795A (ja) * | 1990-09-27 | 1994-06-30 | リサーチ・コーポレイション・テクノロジーズ | キレート化剤 |
| IL117302A (en) * | 1995-03-07 | 2005-03-20 | Univ Hawaii | Cryptophycin derivatives, methods for the production thereof and pharmaceutical compositions containing the same |
| HUP1100731A2 (en) * | 2011-12-30 | 2013-06-28 | Stratoxer S Kft | Complex forming compounds |
| EA019079B1 (ru) * | 2012-06-19 | 2013-12-30 | Елена Владимировна ОРЛОВА | БИОБЕЗОПАСНЫЙ НАНОКОМПОЗИТНЫЙ ПОЛИМЕРНЫЙ СОРБЕНТ ДЛЯ СЕЛЕКТИВНОГО СВЯЗЫВАНИЯ ИЗОТОПОВ Sr И Cs ИЗ ЖИДКИХ СРЕД И СЫРЬЕВАЯ СМЕСЬ ДЛЯ ЕГО ИЗГОТОВЛЕНИЯ |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190462A (en) * | 1978-07-04 | 1980-02-26 | Shell Oil Company | Dissolving barium sulfate scale with aqueous solutions of salts of carboxymethyl monocyclic macrocyclic polyamines |
| US4597903A (en) * | 1984-08-21 | 1986-07-01 | University Of Maryland | Process for the direct preparation of N,N-disubstituted derivatives for 4,13-diaza-18-crown-6 |
| JPS61263964A (ja) * | 1985-05-17 | 1986-11-21 | Terumo Corp | 新規クラウン（チオ）エ−テルおよびその製造方法 |
-
1990
- 1990-01-16 HU HU9502769A patent/HUT73493A/hu unknown
- 1990-01-16 HU HU90145A patent/HU210667B/hu not_active IP Right Cessation
- 1990-11-07 JP JP2515439A patent/JPH04505626A/ja active Pending
- 1990-11-07 AU AU67116/90A patent/AU645507B2/en not_active Ceased
- 1990-11-07 KR KR1019910701044A patent/KR970009042B1/ko not_active Expired - Lifetime
- 1990-11-07 UA UA5001786A patent/UA35547C2/uk unknown
- 1990-11-07 WO PCT/HU1990/000070 patent/WO1991010655A1/en not_active Application Discontinuation
- 1990-11-07 EP EP90916523A patent/EP0463123A1/en not_active Withdrawn
- 1990-11-07 CA CA002048627A patent/CA2048627A1/en not_active Abandoned
- 1990-11-07 RU SU905001786A patent/RU2060256C1/ru active
- 1990-11-22 IN IN943/MAS/90A patent/IN171733B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| UA35547C2 (uk) | 2001-04-16 |
| AU6711690A (en) | 1991-08-05 |
| AU645507B2 (en) | 1994-01-20 |
| EP0463123A1 (en) | 1992-01-02 |
| CA2048627A1 (en) | 1991-07-17 |
| WO1991010655A1 (en) | 1991-07-25 |
| KR920701184A (ko) | 1992-08-11 |
| HU9502769D0 (en) | 1995-11-28 |
| RU2060256C1 (ru) | 1996-05-20 |
| IN171733B (en]) | 1992-12-26 |
| HU900145D0 (en) | 1990-03-28 |
| KR970009042B1 (ko) | 1997-06-03 |
| HU210667B (hu) | 1998-03-30 |
| JPH04505626A (ja) | 1992-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DFD9 | Temporary prot. cancelled due to non-payment of fee |