NO327040B1 - Fremgangsmate ved fremstilling av 4-karboksy-5,8,11-tris-(karboksymetyl)-1-fenyl-2-oksa-5,8,11-triazatridekan-13-syre - Google Patents
Fremgangsmate ved fremstilling av 4-karboksy-5,8,11-tris-(karboksymetyl)-1-fenyl-2-oksa-5,8,11-triazatridekan-13-syre Download PDFInfo
- Publication number
- NO327040B1 NO327040B1 NO20006612A NO20006612A NO327040B1 NO 327040 B1 NO327040 B1 NO 327040B1 NO 20006612 A NO20006612 A NO 20006612A NO 20006612 A NO20006612 A NO 20006612A NO 327040 B1 NO327040 B1 NO 327040B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- solution
- carried out
- iii
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000002253 acid Substances 0.000 title description 10
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 33
- 239000011347 resin Substances 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 125000000129 anionic group Chemical group 0.000 claims description 12
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 12
- 238000001728 nano-filtration Methods 0.000 claims description 9
- 238000010828 elution Methods 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 4
- 239000012465 retentate Substances 0.000 claims description 4
- -1 2-chloro-3-(phenylmethoxy)propionic acid gallium salt Chemical class 0.000 claims description 3
- 239000003463 adsorbent Substances 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000005325 percolation Methods 0.000 claims description 3
- GOBUYIKQNYUPDZ-ZDUSSCGKSA-N (2S)-2-[2-(2-aminoethylamino)ethoxy-benzylamino]-3-hydroxypropanoic acid Chemical class NCCNCCON([C@@H](CO)C(=O)O)CC1=CC=CC=C1 GOBUYIKQNYUPDZ-ZDUSSCGKSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 238000010612 desalination reaction Methods 0.000 claims 1
- 229920005990 polystyrene resin Polymers 0.000 claims 1
- 238000002207 thermal evaporation Methods 0.000 claims 1
- XABKQUVFKKGLSX-UHFFFAOYSA-M potassium;2-chloro-3-phenylmethoxypropanoate Chemical compound [K+].[O-]C(=O)C(Cl)COCC1=CC=CC=C1 XABKQUVFKKGLSX-UHFFFAOYSA-M 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 48
- 239000000047 product Substances 0.000 description 33
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000012535 impurity Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 239000002872 contrast media Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 235000019445 benzyl alcohol Nutrition 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QEYBMJSQGBIRHS-UHFFFAOYSA-N 2-chloro-3-phenylmethoxypropanoic acid Chemical compound OC(=O)C(Cl)COCC1=CC=CC=C1 QEYBMJSQGBIRHS-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052688 Gadolinium Inorganic materials 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002595 magnetic resonance imaging Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000005298 paramagnetic effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ACEFWCFOXROUHU-UHFFFAOYSA-N 2-chloro-4-phenylmethoxybutanoic acid Chemical compound OC(=O)C(Cl)CCOCC1=CC=CC=C1 ACEFWCFOXROUHU-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical class Br* 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 238000012631 diagnostic technique Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 1
- RYHQMKVRYNEBNJ-BMWGJIJESA-K gadoterate meglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 RYHQMKVRYNEBNJ-BMWGJIJESA-K 0.000 description 1
- GFSTXYOTEVLASN-UHFFFAOYSA-K gadoteric acid Chemical compound [Gd+3].OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 GFSTXYOTEVLASN-UHFFFAOYSA-K 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010930 lactamization Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- XLULSJNVZJOFHA-UHFFFAOYSA-M potassium;2-chloro-4-phenylmethoxybutanoate Chemical compound [K+].[O-]C(=O)C(Cl)CCOCC1=CC=CC=C1 XLULSJNVZJOFHA-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- IELXZZXHLWABSU-ZOWNYOTGSA-M sodium (2S)-2-[2-(2-aminoethylamino)ethoxy-benzylamino]-3-hydroxypropanoate Chemical compound [Na+].NCCNCCON([C@@H](CO)C(=O)[O-])CC1=CC=CC=C1 IELXZZXHLWABSU-ZOWNYOTGSA-M 0.000 description 1
- UTIXQHCSWSIAEC-UHFFFAOYSA-M sodium;2-chloro-3-phenylmethoxypropanoate Chemical compound [Na+].[O-]C(=O)C(Cl)COCC1=CC=CC=C1 UTIXQHCSWSIAEC-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 230000001173 tumoral effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98MI001583A ITMI981583A1 (it) | 1998-07-10 | 1998-07-10 | Processo per la preparazione dell'acido 4 -carbossi-5,8,11-tris (carbossimetil)-1-fenil-2-oxa-5,8,11-triazatridecan-13-oico |
| PCT/EP1999/004478 WO2000002847A2 (en) | 1998-07-10 | 1999-06-29 | A process for the preparation of 4-carboxy- 5,8,11- tris(carboxymethyl)- 1-phenyl- 2-oxa- 5,8,11- triazatridecan- 13-oic acid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20006612D0 NO20006612D0 (no) | 2000-12-22 |
| NO20006612L NO20006612L (no) | 2001-01-10 |
| NO327040B1 true NO327040B1 (no) | 2009-04-06 |
Family
ID=11380412
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20006612A NO327040B1 (no) | 1998-07-10 | 2000-12-22 | Fremgangsmate ved fremstilling av 4-karboksy-5,8,11-tris-(karboksymetyl)-1-fenyl-2-oksa-5,8,11-triazatridekan-13-syre |
| NO20084254A NO336375B1 (no) | 1998-07-10 | 2008-10-10 | Fremgangsmåte ved fremstilling av 2-klor-3-(fenylmetoksy)propionsyre-kaliumsalt (II) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20084254A NO336375B1 (no) | 1998-07-10 | 2008-10-10 | Fremgangsmåte ved fremstilling av 2-klor-3-(fenylmetoksy)propionsyre-kaliumsalt (II) |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6162947A (pt) |
| EP (2) | EP1588998B1 (pt) |
| JP (1) | JP4476486B2 (pt) |
| KR (1) | KR100651071B1 (pt) |
| CN (2) | CN1210252C (pt) |
| AT (2) | ATE297890T1 (pt) |
| AU (1) | AU770081B2 (pt) |
| CA (3) | CA2619685C (pt) |
| DE (1) | DE69925836T2 (pt) |
| DK (1) | DK1095009T3 (pt) |
| ES (1) | ES2243063T3 (pt) |
| IL (1) | IL140497A (pt) |
| IT (1) | ITMI981583A1 (pt) |
| NO (2) | NO327040B1 (pt) |
| PT (1) | PT1095009E (pt) |
| WO (1) | WO2000002847A2 (pt) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0325762D0 (en) * | 2003-11-05 | 2003-12-10 | Eastman Kodak Co | Photographic bleach composition |
| EP1762563A1 (en) * | 2005-09-13 | 2007-03-14 | BRACCO IMAGING S.p.A. | Process for the preparation of contrast agents |
| TWI386384B (zh) * | 2006-03-01 | 2013-02-21 | Univ Kaohsiung Medical | 以環烷基三胺基五羧酸化合物作為配位子之具順磁性金屬錯合物 |
| EP2338874A1 (en) * | 2009-12-16 | 2011-06-29 | Bracco Imaging S.p.A | Process for the preparation of chelated compounds |
| CN102408348A (zh) * | 2011-07-26 | 2012-04-11 | 天津市海文普宁科技发展有限公司 | 一种钆贝葡胺的制备新方法 |
| CN102603550B (zh) * | 2012-02-16 | 2014-11-26 | 佛山普正医药科技有限公司 | 一种中间体bopta的制备方法 |
| EP2977369A1 (en) | 2014-07-24 | 2016-01-27 | Bracco Imaging SPA | Preparation of a solid form of gadobenate dimeglumine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820816A (en) * | 1956-12-17 | 1958-01-21 | Gen Aniline & Film Corp | Preparation of alpha, beta-dichloropropionic acid esters |
| IT1213029B (it) * | 1986-01-30 | 1989-12-07 | Bracco Ind Chimica Spa | Chelati di ioni metallici paramagnetici. |
| DE3814887C1 (pt) * | 1988-05-02 | 1989-09-21 | Medice Chem.-Pharm. Fabrik Puetter Gmbh & Co Kg, 5860 Iserlohn, De |
-
1998
- 1998-07-10 IT IT98MI001583A patent/ITMI981583A1/it unknown
-
1999
- 1999-06-29 CA CA2619685A patent/CA2619685C/en not_active Expired - Lifetime
- 1999-06-29 CN CNB99807991XA patent/CN1210252C/zh not_active Expired - Lifetime
- 1999-06-29 JP JP2000559078A patent/JP4476486B2/ja not_active Expired - Lifetime
- 1999-06-29 DK DK99931207T patent/DK1095009T3/da active
- 1999-06-29 CA CA2696806A patent/CA2696806C/en not_active Expired - Lifetime
- 1999-06-29 WO PCT/EP1999/004478 patent/WO2000002847A2/en active IP Right Grant
- 1999-06-29 ES ES99931207T patent/ES2243063T3/es not_active Expired - Lifetime
- 1999-06-29 AU AU47791/99A patent/AU770081B2/en not_active Expired
- 1999-06-29 AT AT99931207T patent/ATE297890T1/de active
- 1999-06-29 PT PT99931207T patent/PT1095009E/pt unknown
- 1999-06-29 EP EP05007144A patent/EP1588998B1/en not_active Expired - Lifetime
- 1999-06-29 CN CNB2005100713118A patent/CN1315776C/zh not_active Expired - Lifetime
- 1999-06-29 KR KR1020007014904A patent/KR100651071B1/ko not_active IP Right Cessation
- 1999-06-29 EP EP99931207A patent/EP1095009B1/en not_active Expired - Lifetime
- 1999-06-29 AT AT05007144T patent/ATE535507T1/de active
- 1999-06-29 DE DE69925836T patent/DE69925836T2/de not_active Expired - Lifetime
- 1999-06-29 CA CA002336919A patent/CA2336919C/en not_active Expired - Lifetime
- 1999-06-29 IL IL14049799A patent/IL140497A/en not_active IP Right Cessation
- 1999-07-08 US US09/349,449 patent/US6162947A/en not_active Expired - Lifetime
-
2000
- 2000-12-22 NO NO20006612A patent/NO327040B1/no not_active IP Right Cessation
-
2008
- 2008-10-10 NO NO20084254A patent/NO336375B1/no not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO336375B1 (no) | Fremgangsmåte ved fremstilling av 2-klor-3-(fenylmetoksy)propionsyre-kaliumsalt (II) | |
| CA1321787C (en) | Process for preparing erythromycin a oxime or a salt thereof | |
| JP5204724B2 (ja) | １，４，７，１０−テトラアザシクロドデカン−１，４，７−三酢酸及びその誘導体の調製のための方法 | |
| JPH0363556B2 (pt) | ||
| US6894151B2 (en) | Lithium complexes of N-(1-hydroxymethyl-2,3-dihydroxypropyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane, their production and use | |
| CA2621339C (en) | Process for the preparation of contrast agents | |
| CA2351717C (en) | A process for the preparation of n,n'-bis[2,3-dihydroxypropyl]-5-[(hydroxyacetyl)methylamino]-2,4,6-triiodo-1,3-benzenedicarboxamide | |
| JPH0357895B2 (pt) | ||
| US4124636A (en) | Method of preparing monopotassium L-malate and its monohydrate | |
| JP2947492B2 (ja) | テアニンの製造法 | |
| JP7090645B2 (ja) | イオシメノールの製造方法 | |
| JP3150225B2 (ja) | モノｐ−ニトロベンジルマロネートの結晶変態及びその製法 | |
| JP3176261B2 (ja) | アントラキノン系化合物の製造方法 | |
| JPH0335308B2 (pt) | ||
| KR20220044249A (ko) | 시트룰린의 개선된 합성 및 정제 방법 | |
| PT1603863E (pt) | Processo para a preparação de ácidos amino-metil-cicloalcano-acéticos | |
| CN111909044A (zh) | 2-(烷基氨基)乙基苯甲酸酯类化合物的合成方法 | |
| JP2537204B2 (ja) | ヒダントイン類の製造方法 | |
| WO2006098705A1 (en) | Process for producing biphenyl-tetrazole compounds | |
| WO2003066657A1 (en) | A process for preparing ursodeoxycholic acid dusulphate and pharmaceutically acceptable salts thereof | |
| EP2001869A1 (en) | Process for producing biphenyl-tetrazole compounds | |
| JPS649309B2 (pt) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |