JPH04505626A - １，４，１０，１３，―テトラオキサ―７，１６―ジアザシクロオクタデカン誘導体類、それらを含む医薬組成物及び生物からの毒性金属イオン及び放射性同位体の除去のためへのそれらの使用 - Google Patents
１，４，１０，１３，―テトラオキサ―７，１６―ジアザシクロオクタデカン誘導体類、それらを含む医薬組成物及び生物からの毒性金属イオン及び放射性同位体の除去のためへのそれらの使用Info
- Publication number
- JPH04505626A JPH04505626A JP2515439A JP51543990A JPH04505626A JP H04505626 A JPH04505626 A JP H04505626A JP 2515439 A JP2515439 A JP 2515439A JP 51543990 A JP51543990 A JP 51543990A JP H04505626 A JPH04505626 A JP H04505626A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- formula
- group
- independently
- tetraoxa
- 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.)
- Pending
Links
- 229910021645 metal ion Inorganic materials 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title description 6
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical class C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 title description 3
- 231100000331 toxic Toxicity 0.000 title description 2
- 230000002588 toxic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000000243 solution Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 230000002285 radioactive effect Effects 0.000 claims description 21
- -1 ammonium ions Chemical class 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 150000001340 alkali metals Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- 239000011575 calcium Substances 0.000 claims description 10
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 8
- 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 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910003002 lithium salt Inorganic materials 0.000 claims description 4
- 159000000002 lithium salts Chemical class 0.000 claims description 4
- 239000002674 ointment Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 229910001415 sodium ion Inorganic materials 0.000 claims description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000008298 dragée Substances 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 229910001416 lithium ion Inorganic materials 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 3
- 239000000443 aerosol Substances 0.000 claims 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 claims 1
- 239000000047 product Substances 0.000 description 56
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 46
- 150000003839 salts Chemical class 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 241001465754 Metazoa Species 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 22
- 238000001228 spectrum Methods 0.000 description 20
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 238000000605 extraction Methods 0.000 description 15
- 239000011780 sodium chloride Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 229910052712 strontium Inorganic materials 0.000 description 12
- 239000013543 active substance Substances 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- VBZOUUJVGADJBK-UHFFFAOYSA-N 2-bromopropanedioic acid Chemical compound OC(=O)C(Br)C(O)=O VBZOUUJVGADJBK-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 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 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 9
- 230000007717 exclusion Effects 0.000 description 9
- 230000008030 elimination Effects 0.000 description 8
- 238000003379 elimination reaction Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 230000017531 blood circulation Effects 0.000 description 7
- 210000004072 lung Anatomy 0.000 description 7
- 150000002678 macrocyclic compounds Chemical class 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000009885 systemic effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 210000000988 bone and bone Anatomy 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- IIYNNSHGLFMMRP-UHFFFAOYSA-L disodium;2-hydroxypropanedioate Chemical group [Na+].[Na+].[O-]C(=O)C(O)C([O-])=O IIYNNSHGLFMMRP-UHFFFAOYSA-L 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000000155 isotopic effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000037081 physical activity Effects 0.000 description 4
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 229910052776 Thorium Inorganic materials 0.000 description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 210000002808 connective tissue Anatomy 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 239000008263 liquid aerosol Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000002739 cryptand Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000469 ethanolic extract Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000001723 extracellular space Anatomy 0.000 description 2
- 229910001448 ferrous ion Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
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- 210000001519 tissue Anatomy 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 125000006532 (C3-C5) alkyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical class COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-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
- JCPUKHWHNNFWDX-UHFFFAOYSA-N 2-(bromomethyl)propanedioic acid Chemical compound OC(=O)C(CBr)C(O)=O JCPUKHWHNNFWDX-UHFFFAOYSA-N 0.000 description 1
- SSEXAOZOZMDLSJ-UHFFFAOYSA-N 2-benzyl-2-bromopropanedioic acid Chemical compound OC(=O)C(Br)(C(O)=O)CC1=CC=CC=C1 SSEXAOZOZMDLSJ-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
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001649081 Dina Species 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010018473 Glycosuria Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000286819 Malo Species 0.000 description 1
- FQIZXFFVFPTVBE-UHFFFAOYSA-N N.N.[Ca+2] Chemical compound N.N.[Ca+2] FQIZXFFVFPTVBE-UHFFFAOYSA-N 0.000 description 1
- 206010033557 Palpitations Diseases 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 1
- CIOAGBVUUVVLOB-NJFSPNSNSA-N Strontium-90 Chemical compound [90Sr] CIOAGBVUUVVLOB-NJFSPNSNSA-N 0.000 description 1
- 150000001218 Thorium Chemical class 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- TXKUEILVFFGAIG-UHFFFAOYSA-K [OH-].[OH-].[OH-].[Na+].[Na+].[Na+] Chemical compound [OH-].[OH-].[OH-].[Na+].[Na+].[Na+] TXKUEILVFFGAIG-UHFFFAOYSA-K 0.000 description 1
- NQMZNYDGOJUGRE-UHFFFAOYSA-J [OH-].[OH-].[OH-].[OH-].[Ca++].[Ca++] Chemical compound [OH-].[OH-].[OH-].[OH-].[Ca++].[Ca++] NQMZNYDGOJUGRE-UHFFFAOYSA-J 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
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- 238000009825 accumulation Methods 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- 210000000436 anus Anatomy 0.000 description 1
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- JYJWPXDYSGARNH-UHFFFAOYSA-N azacyclooctadecane Chemical compound C1CCCCCCCCNCCCCCCCC1 JYJWPXDYSGARNH-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- XCETYVGOGDDIMM-UHFFFAOYSA-L calcium;2-hydroxypropanedioate Chemical compound [Ca+2].[O-]C(=O)C(O)C([O-])=O XCETYVGOGDDIMM-UHFFFAOYSA-L 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- JNFIMRWCDIOUMT-UHFFFAOYSA-N cyclooctadecane Chemical compound C1CCCCCCCCCCCCCCCCC1 JNFIMRWCDIOUMT-UHFFFAOYSA-N 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RVPVRDXYQKGNMQ-UHFFFAOYSA-N lead(2+) Chemical group [Pb+2] RVPVRDXYQKGNMQ-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- NIAXLPMJTSWMRK-UHFFFAOYSA-L magnesium;dichloride;pentahydrate Chemical compound O.O.O.O.O.[Mg+2].[Cl-].[Cl-] NIAXLPMJTSWMRK-UHFFFAOYSA-L 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
- 229960003857 proglumide Drugs 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 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
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- XZPVPNZTYPUODG-UHFFFAOYSA-M sodium;chloride;dihydrate Chemical compound O.O.[Na+].[Cl-] XZPVPNZTYPUODG-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- CIOAGBVUUVVLOB-OUBTZVSYSA-N strontium-89 Chemical compound [89Sr] CIOAGBVUUVVLOB-OUBTZVSYSA-N 0.000 description 1
- 229940006509 strontium-89 Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU145/90 | 1990-01-16 | ||
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| JPH04505626A true JPH04505626A (ja) | 1992-10-01 |
Family
ID=10948158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2515439A Pending JPH04505626A (ja) | 1990-01-16 | 1990-11-07 | １，４，１０，１３，―テトラオキサ―７，１６―ジアザシクロオクタデカン誘導体類、それらを含む医薬組成物及び生物からの毒性金属イオン及び放射性同位体の除去のためへのそれらの使用 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0463123A1 (2) |
| JP (1) | JPH04505626A (2) |
| KR (1) | KR970009042B1 (2) |
| AU (1) | AU645507B2 (2) |
| CA (1) | CA2048627A1 (2) |
| HU (2) | HUT73493A (2) |
| IN (1) | IN171733B (2) |
| RU (1) | RU2060256C1 (2) |
| UA (1) | UA35547C2 (2) |
| WO (1) | WO1991010655A1 (2) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015503542A (ja) * | 2011-12-30 | 2015-02-02 | シュトラトクセル（シュ） コルラートルト フェレレーシュシェーギュー タールシャシャーグ | 錯体形成化合物 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0554358A4 (en) * | 1990-09-27 | 1995-09-06 | Brunswick Corp | Chelating agents |
| IL117302A (en) * | 1995-03-07 | 2005-03-20 | Univ Hawaii | Cryptophycin derivatives, methods for the production thereof and pharmaceutical compositions containing the same |
| 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 CA CA002048627A patent/CA2048627A1/en not_active Abandoned
- 1990-11-07 JP JP2515439A patent/JPH04505626A/ja active Pending
- 1990-11-07 KR KR1019910701044A patent/KR970009042B1/ko not_active Expired - Lifetime
- 1990-11-07 WO PCT/HU1990/000070 patent/WO1991010655A1/en not_active Ceased
- 1990-11-07 UA UA5001786A patent/UA35547C2/uk unknown
- 1990-11-07 AU AU67116/90A patent/AU645507B2/en not_active Ceased
- 1990-11-07 EP EP90916523A patent/EP0463123A1/en not_active Withdrawn
- 1990-11-07 RU SU905001786A patent/RU2060256C1/ru active
- 1990-11-22 IN IN943/MAS/90A patent/IN171733B/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015503542A (ja) * | 2011-12-30 | 2015-02-02 | シュトラトクセル（シュ） コルラートルト フェレレーシュシェーギュー タールシャシャーグ | 錯体形成化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2048627A1 (en) | 1991-07-17 |
| HU9502769D0 (en) | 1995-11-28 |
| AU645507B2 (en) | 1994-01-20 |
| RU2060256C1 (ru) | 1996-05-20 |
| IN171733B (2) | 1992-12-26 |
| HUT73493A (en) | 1996-08-28 |
| UA35547C2 (uk) | 2001-04-16 |
| KR970009042B1 (ko) | 1997-06-03 |
| KR920701184A (ko) | 1992-08-11 |
| EP0463123A1 (en) | 1992-01-02 |
| HU210667B (hu) | 1998-03-30 |
| HU900145D0 (en) | 1990-03-28 |
| WO1991010655A1 (en) | 1991-07-25 |
| AU6711690A (en) | 1991-08-05 |
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