AU2005240257B2 - High yield and rapid syntheses methods for producing metallo-organic salts - Google Patents
High yield and rapid syntheses methods for producing metallo-organic salts Download PDFInfo
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- AU2005240257B2 AU2005240257B2 AU2005240257A AU2005240257A AU2005240257B2 AU 2005240257 B2 AU2005240257 B2 AU 2005240257B2 AU 2005240257 A AU2005240257 A AU 2005240257A AU 2005240257 A AU2005240257 A AU 2005240257A AU 2005240257 B2 AU2005240257 B2 AU 2005240257B2
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- AU
- Australia
- Prior art keywords
- strontium
- acid
- salt
- salts
- glutamate
- 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.)
- Ceased
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- 238000000034 method Methods 0.000 title claims abstract description 102
- 150000003839 salts Chemical class 0.000 title claims abstract description 96
- 238000003786 synthesis reaction Methods 0.000 title description 62
- 159000000008 strontium salts Chemical class 0.000 claims abstract description 106
- 150000007524 organic acids Chemical class 0.000 claims abstract description 29
- 229910052712 strontium Inorganic materials 0.000 claims description 111
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 103
- 238000006243 chemical reaction Methods 0.000 claims description 55
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- -1 halogen salt Chemical class 0.000 claims description 40
- LVZZABGEQTZXHP-UHFFFAOYSA-L strontium;propanedioate Chemical compound [Sr+2].[O-]C(=O)CC([O-])=O LVZZABGEQTZXHP-UHFFFAOYSA-L 0.000 claims description 34
- XUBXWWLLZIPPHW-DFWYDOINSA-L strontium;(2s)-2-aminopentanedioate Chemical compound [Sr+2].[O-]C(=O)[C@@H](N)CCC([O-])=O XUBXWWLLZIPPHW-DFWYDOINSA-L 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 30
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 claims description 29
- 229910001866 strontium hydroxide Inorganic materials 0.000 claims description 27
- 238000001556 precipitation Methods 0.000 claims description 17
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 15
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims description 13
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 claims description 13
- 150000004686 pentahydrates Chemical class 0.000 claims description 13
- 229910000018 strontium carbonate Inorganic materials 0.000 claims description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 11
- 229910001427 strontium ion Inorganic materials 0.000 claims description 11
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 10
- PWYYWQHXAPXYMF-UHFFFAOYSA-N strontium(2+) Chemical compound [Sr+2] PWYYWQHXAPXYMF-UHFFFAOYSA-N 0.000 claims description 10
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- 229930182847 D-glutamic acid Natural products 0.000 claims description 7
- 239000001530 fumaric acid Substances 0.000 claims description 6
- 230000001976 improved effect Effects 0.000 claims description 6
- 229940107700 pyruvic acid Drugs 0.000 claims description 6
- 229930195713 D-glutamate Natural products 0.000 claims description 5
- 235000010323 ascorbic acid Nutrition 0.000 claims description 5
- 239000011668 ascorbic acid Substances 0.000 claims description 5
- 229960005070 ascorbic acid Drugs 0.000 claims description 5
- 229940009098 aspartate Drugs 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- DJSXNILVACEBLP-UHFFFAOYSA-N ranelic acid Chemical compound OC(=O)CN(CC(O)=O)C=1SC(C(O)=O)=C(CC(O)=O)C=1C#N DJSXNILVACEBLP-UHFFFAOYSA-N 0.000 claims description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
- HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 claims description 4
- 229940009533 alpha-ketoglutaric acid Drugs 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 4
- 235000014655 lactic acid Nutrition 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 229950003464 ranelic acid Drugs 0.000 claims description 4
- INVUEPFVUMNRGH-DKWTVANSSA-L strontium;(2s)-2-aminobutanedioate Chemical compound [Sr+2].[O-]C(=O)[C@@H](N)CC([O-])=O INVUEPFVUMNRGH-DKWTVANSSA-L 0.000 claims description 4
- JPIJQSOTBSSVTP-STHAYSLISA-N L-threonic acid Chemical compound OC[C@H](O)[C@@H](O)C(O)=O JPIJQSOTBSSVTP-STHAYSLISA-N 0.000 claims description 3
- 150000003841 chloride salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- VUWAXXIHYHUOJV-TYYBGVCCSA-L strontium;(e)-but-2-enedioate Chemical compound [Sr+2].[O-]C(=O)\C=C\C([O-])=O VUWAXXIHYHUOJV-TYYBGVCCSA-L 0.000 claims description 3
- VUWAXXIHYHUOJV-ODZAUARKSA-L strontium;(z)-but-2-enedioate Chemical compound [Sr+2].[O-]C(=O)\C=C/C([O-])=O VUWAXXIHYHUOJV-ODZAUARKSA-L 0.000 claims description 3
- CRLDSNGPLRRUQU-UHFFFAOYSA-L strontium;butanedioate Chemical compound [Sr+2].[O-]C(=O)CCC([O-])=O CRLDSNGPLRRUQU-UHFFFAOYSA-L 0.000 claims description 3
- JPIJQSOTBSSVTP-GBXIJSLDSA-N D-threonic acid Chemical compound OC[C@@H](O)[C@H](O)C(O)=O JPIJQSOTBSSVTP-GBXIJSLDSA-N 0.000 claims description 2
- MLCQLNYCRIEWMX-ZZMNMWMASA-L strontium (2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-5-oxo-2H-furan-4-olate Chemical compound [Sr+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] MLCQLNYCRIEWMX-ZZMNMWMASA-L 0.000 claims description 2
- YXAMJFINXWQMCB-UHFFFAOYSA-L strontium;2-oxopropanoate Chemical compound [Sr+2].CC(=O)C([O-])=O.CC(=O)C([O-])=O YXAMJFINXWQMCB-UHFFFAOYSA-L 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- 229940022036 threonate Drugs 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- CCUZKVDGQHXAFK-UHFFFAOYSA-L strontium;2-hydroxypropanoate Chemical compound [Sr+2].CC(O)C([O-])=O.CC(O)C([O-])=O CCUZKVDGQHXAFK-UHFFFAOYSA-L 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 36
- 229910052751 metal Inorganic materials 0.000 abstract description 24
- 239000002184 metal Substances 0.000 abstract description 24
- 238000001308 synthesis method Methods 0.000 abstract description 17
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 11
- 235000005985 organic acids Nutrition 0.000 abstract description 5
- 150000001768 cations Chemical class 0.000 abstract description 3
- 230000000737 periodic effect Effects 0.000 abstract description 3
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 76
- 239000013078 crystal Substances 0.000 description 63
- 239000000243 solution Substances 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000000725 suspension Substances 0.000 description 37
- 239000002253 acid Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 29
- 239000000843 powder Substances 0.000 description 25
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 20
- 238000009835 boiling Methods 0.000 description 19
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 18
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 15
- 229960005069 calcium Drugs 0.000 description 15
- 239000011575 calcium Substances 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 229910052791 calcium Inorganic materials 0.000 description 14
- 229960002989 glutamic acid Drugs 0.000 description 14
- 239000013580 millipore water Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 238000002424 x-ray crystallography Methods 0.000 description 14
- 150000001342 alkaline earth metals Chemical class 0.000 description 13
- 238000000705 flame atomic absorption spectrometry Methods 0.000 description 13
- 229910021645 metal ion Inorganic materials 0.000 description 12
- 229910003514 Sr(OH) Inorganic materials 0.000 description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 description 11
- NWUFXBCRFNBCPV-WIMOTELVSA-L strontium;(2s)-2-aminopentanedioate;hexahydrate Chemical compound O.O.O.O.O.O.[Sr+2].[O-]C(=O)[C@@H](N)CCC([O-])=O NWUFXBCRFNBCPV-WIMOTELVSA-L 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 239000001569 carbon dioxide Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229940024606 amino acid Drugs 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 229910052749 magnesium Inorganic materials 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 9
- 229940091250 magnesium supplement Drugs 0.000 description 9
- 238000005457 optimization Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 150000002891 organic anions Chemical class 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 229910001631 strontium chloride Inorganic materials 0.000 description 8
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 8
- UJPWWRPNIRRCPJ-UHFFFAOYSA-L strontium;dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Sr+2] UJPWWRPNIRRCPJ-UHFFFAOYSA-L 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229940049906 glutamate Drugs 0.000 description 6
- 229930195712 glutamate Natural products 0.000 description 6
- 235000013922 glutamic acid Nutrition 0.000 description 6
- 239000004220 glutamic acid Substances 0.000 description 6
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000037361 pathway Effects 0.000 description 6
- 230000002285 radioactive effect Effects 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 101100496858 Mus musculus Colec12 gene Proteins 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229960005261 aspartic acid Drugs 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 210000000988 bone and bone Anatomy 0.000 description 5
- 239000008366 buffered solution Substances 0.000 description 5
- 210000000845 cartilage Anatomy 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000004687 hexahydrates Chemical group 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 239000004570 mortar (masonry) Substances 0.000 description 5
- PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 5
- NWUFXBCRFNBCPV-ALWRQVICSA-L strontium (2R)-2-aminopentanedioate hexahydrate Chemical compound O.O.O.O.O.O.[Sr+2].[O-]C(=O)[C@H](N)CCC([O-])=O NWUFXBCRFNBCPV-ALWRQVICSA-L 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- INTLZEZIBJKNKI-SQGDDOFFSA-N (2S)-2-aminobutanedioic acid trihydrate Chemical compound O.O.O.N[C@@H](CC(=O)O)C(=O)O INTLZEZIBJKNKI-SQGDDOFFSA-N 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 4
- 150000001734 carboxylic acid salts Chemical class 0.000 description 4
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 4
- INIYRMMIDZWSKY-UHFFFAOYSA-L disodium;propanedioate;hydrate Chemical compound O.[Na+].[Na+].[O-]C(=O)CC([O-])=O INIYRMMIDZWSKY-UHFFFAOYSA-L 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 238000003760 magnetic stirring Methods 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000011343 solid material Substances 0.000 description 4
- DHEQXMRUPNDRPG-UHFFFAOYSA-N strontium nitrate Chemical compound [Sr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DHEQXMRUPNDRPG-UHFFFAOYSA-N 0.000 description 4
- CIOAGBVUUVVLOB-OUBTZVSYSA-N strontium-89 Chemical compound [89Sr] CIOAGBVUUVVLOB-OUBTZVSYSA-N 0.000 description 4
- 229940095064 tartrate Drugs 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 208000001132 Osteoporosis Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 235000003704 aspartic acid Nutrition 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 3
- 150000005323 carbonate salts Chemical class 0.000 description 3
- 230000008414 cartilage metabolism Effects 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 238000002050 diffraction method Methods 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000012803 optimization experiment Methods 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IUMOPUXDPFMEMV-UHFFFAOYSA-L strontium;2,3-dihydroxybutanedioate Chemical compound [Sr+2].[O-]C(=O)C(O)C(O)C([O-])=O IUMOPUXDPFMEMV-UHFFFAOYSA-L 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- GAMIYQSIKAOVTG-DFWYDOINSA-L zinc;(2s)-2-aminopentanedioate Chemical compound [Zn+2].[O-]C(=O)[C@@H](N)CCC([O-])=O GAMIYQSIKAOVTG-DFWYDOINSA-L 0.000 description 3
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- 229960002051 trandolapril Drugs 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- DPUOLQHDNGRHBS-MDZDMXLPSA-N trans-Brassidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-MDZDMXLPSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical group 0.000 description 1
- QGAPCDHPGCYAKM-UHFFFAOYSA-H tristrontium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Sr+2].[Sr+2].[Sr+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QGAPCDHPGCYAKM-UHFFFAOYSA-H 0.000 description 1
- JOPDZQBPOWAEHC-UHFFFAOYSA-H tristrontium;diphosphate Chemical compound [Sr+2].[Sr+2].[Sr+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JOPDZQBPOWAEHC-UHFFFAOYSA-H 0.000 description 1
- 229960002004 valdecoxib Drugs 0.000 description 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CZVMEWJATZZKSN-LHWPGRLPSA-L zinc;(2s)-2-aminopentanedioate;dihydrate Chemical compound O.O.[Zn+2].[O-]C(=O)[C@@H](N)CCC([O-])=O CZVMEWJATZZKSN-LHWPGRLPSA-L 0.000 description 1
- ZNUNQZGDGDPJIM-UHFFFAOYSA-L zinc;propanedioate;dihydrate Chemical compound O.O.[Zn+2].[O-]C(=O)CC([O-])=O ZNUNQZGDGDPJIM-UHFFFAOYSA-L 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/194—Carboxylic acids, e.g. valproic acid having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/08—Malonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/DK2004/000326 WO2004098617A2 (en) | 2003-05-07 | 2004-05-06 | Controlled release composition containing a strontium salt |
| AUPCT/DK2004/000327 | 2004-05-06 | ||
| DKPCT/DK2004/000328 | 2004-05-06 | ||
| PCT/DK2004/000328 WO2004098619A2 (en) | 2003-05-07 | 2004-05-06 | Treating cartilage / bone conditions with water-soluble strontium salts |
| AUPCT/DK2004/000326 | 2004-05-06 | ||
| PCT/DK2004/000327 WO2004098618A2 (en) | 2003-05-07 | 2004-05-06 | Strontium combinations for prophylaxis/treatment of cartilage and/or bone conditions |
| DKPA200401708 | 2004-11-05 | ||
| DKPA200401708 | 2004-11-05 | ||
| PCT/DK2005/000307 WO2005108339A2 (en) | 2004-05-06 | 2005-05-05 | High yield and rapid syntheses methods for producing metallo-organic salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005240257A1 AU2005240257A1 (en) | 2005-11-17 |
| AU2005240257B2 true AU2005240257B2 (en) | 2011-11-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005240257A Ceased AU2005240257B2 (en) | 2004-05-06 | 2005-05-05 | High yield and rapid syntheses methods for producing metallo-organic salts |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7589235B2 (enExample) |
| EP (1) | EP1744770A2 (enExample) |
| JP (1) | JP4954867B2 (enExample) |
| KR (1) | KR20110124317A (enExample) |
| CN (1) | CN101010087B (enExample) |
| AU (1) | AU2005240257B2 (enExample) |
| CA (1) | CA2565840A1 (enExample) |
| WO (1) | WO2005108339A2 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004002832T2 (de) * | 2003-05-07 | 2007-06-06 | Osteologix A/S | Behandlung von knorpel/knochen-erkrankungen mit wasserlöslichen strontiumsalzen |
| PT1745791E (pt) * | 2003-05-07 | 2013-07-23 | Osteologix As | Tratamento de afeções cartilagíneas/ósseas com sais de estrôncio hidrossolúveis |
| US20060216358A1 (en) * | 2003-05-07 | 2006-09-28 | Christian Hansen | Controlled release composition containing a strontium salt |
| AU2005216596B2 (en) | 2004-02-26 | 2011-03-24 | Osteologix A/S | Strontium-containing compounds for use in the prevention or treatment of necrotic bone conditions |
| PT2319581E (pt) | 2004-11-26 | 2015-06-30 | Ucl Business Plc | Composições compreendendo ornitina e fenilacetato ou fenilbutirato para tratamento de encefalopatia hepática |
| KR100878140B1 (ko) * | 2007-01-29 | 2009-01-12 | 한미약품 주식회사 | 아토바스타틴의 스트론튬염 또는 이의 수화물, 및 이를포함하는 약학 조성물 |
| CN101327203B (zh) * | 2007-06-19 | 2011-03-30 | 惠州市昆泰精细化工有限公司 | 没食子酸螯合物组合物及其应用 |
| ES2791524T3 (es) | 2009-04-03 | 2020-11-04 | Ocera Therapeutics Inc | Fenilacetato de L-ornitina y métodos de elaboración del mismo |
| EP3517110A1 (en) | 2009-06-08 | 2019-07-31 | UCL Business PLC | Treatment of inflammation using l-ornithine phenylacetate |
| FR2963837B1 (fr) * | 2010-08-10 | 2012-08-31 | Air Liquide | Traitement a niveaux multiples pour optimiser une ou plusieurs unites de separation de fluides |
| EP2625162B1 (en) | 2010-10-06 | 2019-03-13 | Ocera Therapeutics, Inc. | Methods of making l-ornithine phenyl acetate |
| EP2530068A1 (en) | 2011-05-31 | 2012-12-05 | Lacer, S.A. | New strontium salts, synthesis and use thereof in the treatment of osteoporosis |
| CN103173845B (zh) * | 2012-01-12 | 2015-06-03 | 江苏爱特恩高分子材料有限公司 | 一种对苯二甲酸金属盐晶须的生产方法与应用 |
| RU2564858C1 (ru) * | 2014-06-04 | 2015-10-10 | Закрытое акционерное общество "ЭКОС-1" | Способ получения безводного формиата стронция |
| BR112017010761B1 (pt) | 2014-11-24 | 2022-10-18 | Ucl Business Plc | Tratamento de doenças associadas à ativação de célula estrelada hepática com o uso de terapias de redução de amônia |
| JP6464475B2 (ja) * | 2015-03-02 | 2019-02-06 | 清水建設株式会社 | 放射性ストロンチウムの分析方法 |
| CA2995823A1 (en) | 2015-08-18 | 2017-02-23 | Ocera Therapeutics, Inc. | Treatment and prevention of muscle loss using l-ornithine in combination with at least one of phenylacetate and phenylbutyrate |
| WO2018084959A2 (en) | 2016-09-30 | 2018-05-11 | Nelson Deanna J | Pharmaceutical quality strontium l-lactate |
| CN106699781B (zh) * | 2016-12-16 | 2018-11-16 | 商丘师范学院 | 基于衣康酸-吡嗪混合配体的锌(ii)荧光材料及制备方法 |
| EP3621947A4 (en) | 2017-05-11 | 2021-03-10 | Ocera Therapeutics, Inc. | L-ORNITHINE PHENYLACETATE MANUFACTURING PROCESSES |
| CN114410396A (zh) | 2017-06-27 | 2022-04-29 | 埃科莱布美国股份有限公司 | 洗衣应用中的无磷过渡金属控制 |
| CN108047155A (zh) * | 2017-11-29 | 2018-05-18 | 浙江震元制药有限公司 | 一种双芳基取代的异恶唑化合物的定向制备方法及用途 |
| WO2019217790A1 (en) * | 2018-05-11 | 2019-11-14 | Premex, Inc. | Process for quantification of metal amino acid chelates in solutions and solids |
| SG11202102204PA (en) * | 2018-09-25 | 2021-04-29 | Ponce De Leon Health Designated Activity Company | Process of making calcium alpha-ketoglutarate |
| CN109444277B (zh) * | 2018-10-29 | 2021-05-11 | 郑州大学第一附属医院 | 代谢标志物在制备胶质瘤诊断试剂盒方面的应用 |
| CN109622238B (zh) * | 2018-12-18 | 2020-07-17 | 商洛学院 | 一种用于从金红石重选中矿中浮选回收金红石的药剂组合 |
| CN110668934A (zh) * | 2019-10-14 | 2020-01-10 | 惠州市志海新威科技有限公司 | 一种酒石酸锌的制备方法及其在稳定剂中的应用 |
| CN114479098B (zh) * | 2021-12-17 | 2023-05-23 | 广东石油化工学院 | 一种可控微介孔金属有机框架hkust-1材料及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003028742A1 (en) * | 2001-09-28 | 2003-04-10 | Santosolve As | Strontium compound for treatment of sub-dermal soft tissue pain |
| AU2004237439A1 (en) * | 2003-05-07 | 2004-11-18 | Osteologix A/S | Treating cartilage/bone conditions with water-soluble strontium salts |
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| BE532864A (enExample) | 1952-04-29 | |||
| US3478083A (en) * | 1966-02-01 | 1969-11-11 | Abbott Lab | Nor-androstene steroid derivatives |
| SE340807B (enExample) | 1966-05-06 | 1971-12-06 | Astra Ab | |
| US4056567A (en) | 1976-03-08 | 1977-11-01 | Lever Brothers Company | Chemical processes for preparing citric acid |
| DE2913592C2 (de) * | 1979-04-04 | 1988-11-10 | Chemische Werke München Otto Bärlocher GmbH, 8000 München | Verfahen zur Herstellung von Metallseifen |
| DE3735264C1 (de) * | 1987-10-17 | 1988-08-25 | Degussa | Verfahren zur Herstellung von Erdalkalimetallsalzen der L-2-Pyrrolidon-5-carbonsaeure |
| FR2651497B1 (fr) | 1989-09-01 | 1991-10-25 | Adir | Nouveaux sels de metaux bivalents de l'acide n, n-di (carboxymethyl)amino-2 cyano-3 carboxymethyl-4 carboxy-5 thiophene, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| FR2658816A1 (fr) * | 1990-02-27 | 1991-08-30 | Adir | Nouveaux sels de metaux alcalinoterreux d'oxa-polyacides leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2665896A1 (fr) * | 1990-08-16 | 1992-02-21 | Rhone Poulenc Chimie | Carboxylates metalliques, leur preparation et compositions supraconductrices obtenues a partir de ceux-ci. |
| JP3566984B2 (ja) * | 1994-06-02 | 2004-09-15 | 帝人株式会社 | 骨形成促進剤 |
| FR2749759B1 (fr) * | 1996-06-17 | 1999-11-26 | Adir | Utilisation de sels de strontium pour l'obtention de compositions pharmaceutiques destinees au traitement de l'arthrose |
| GB9814316D0 (en) | 1998-07-02 | 1998-09-02 | Smithkline Beecham Plc | Novel compounds |
| DE19837522A1 (de) * | 1998-08-19 | 2000-02-24 | Clariant Gmbh | Verwendung von Metall-Carboxylaten und -Sulfonaten als Ladungssteuermittel |
| US6232497B1 (en) * | 1998-12-23 | 2001-05-15 | Skw Trostberg Aktiengesellschaft | Method for producing alkali metal and alkaline earth metal pyruvates |
| FR2844795B1 (fr) | 2002-09-24 | 2004-10-22 | Servier Lab | Nouveau procede de synthese industriel du ranelate de strontium et de ses hydrates |
| US20060216358A1 (en) | 2003-05-07 | 2006-09-28 | Christian Hansen | Controlled release composition containing a strontium salt |
| PT1745791E (pt) | 2003-05-07 | 2013-07-23 | Osteologix As | Tratamento de afeções cartilagíneas/ósseas com sais de estrôncio hidrossolúveis |
| AU2005216596B2 (en) * | 2004-02-26 | 2011-03-24 | Osteologix A/S | Strontium-containing compounds for use in the prevention or treatment of necrotic bone conditions |
| WO2006089546A1 (en) | 2005-02-28 | 2006-08-31 | Osteologix A/S | Tablets comprising a high load of strontium |
| CA2570503A1 (en) * | 2004-06-17 | 2005-12-29 | Osteologix A/S | A method of improving the medical treatment of pain |
| JP2008502609A (ja) * | 2004-06-17 | 2008-01-31 | オステオロジックス エイ／エス | リウマチおよび関節性疾患の治療改善方法 |
| US20090137678A1 (en) * | 2005-07-06 | 2009-05-28 | Stephan Christgau | High yield synthesis methods for producing organic salts of strontium |
-
2005
- 2005-05-05 WO PCT/DK2005/000307 patent/WO2005108339A2/en not_active Ceased
- 2005-05-05 CN CN2005800226577A patent/CN101010087B/zh not_active Expired - Fee Related
- 2005-05-05 KR KR1020117022010A patent/KR20110124317A/ko not_active Ceased
- 2005-05-05 JP JP2007511865A patent/JP4954867B2/ja not_active Expired - Fee Related
- 2005-05-05 CA CA002565840A patent/CA2565840A1/en not_active Abandoned
- 2005-05-05 US US11/579,773 patent/US7589235B2/en not_active Expired - Fee Related
- 2005-05-05 AU AU2005240257A patent/AU2005240257B2/en not_active Ceased
- 2005-05-05 EP EP05734804A patent/EP1744770A2/en not_active Withdrawn
-
2009
- 2009-08-03 US US12/534,435 patent/US8183409B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003028742A1 (en) * | 2001-09-28 | 2003-04-10 | Santosolve As | Strontium compound for treatment of sub-dermal soft tissue pain |
| AU2004237439A1 (en) * | 2003-05-07 | 2004-11-18 | Osteologix A/S | Treating cartilage/bone conditions with water-soluble strontium salts |
Non-Patent Citations (1)
| Title |
|---|
| BACCE, E.D. et al., International Journal of Inorganic Materials, 2001, vol. 3, pages 443-452 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1744770A2 (en) | 2007-01-24 |
| US7589235B2 (en) | 2009-09-15 |
| WO2005108339A3 (en) | 2005-12-29 |
| AU2005240257A1 (en) | 2005-11-17 |
| JP2007536288A (ja) | 2007-12-13 |
| KR20110124317A (ko) | 2011-11-16 |
| CN101010087B (zh) | 2012-06-27 |
| US8183409B2 (en) | 2012-05-22 |
| US20090291926A1 (en) | 2009-11-26 |
| WO2005108339A2 (en) | 2005-11-17 |
| US20070282127A1 (en) | 2007-12-06 |
| CA2565840A1 (en) | 2005-11-17 |
| CN101010087A (zh) | 2007-08-01 |
| JP4954867B2 (ja) | 2012-06-20 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |