JPH10503529A - ジカルボン酸二塩化物の製造方法 - Google Patents
ジカルボン酸二塩化物の製造方法Info
- Publication number
- JPH10503529A JPH10503529A JP8535346A JP53534696A JPH10503529A JP H10503529 A JPH10503529 A JP H10503529A JP 8535346 A JP8535346 A JP 8535346A JP 53534696 A JP53534696 A JP 53534696A JP H10503529 A JPH10503529 A JP H10503529A
- Authority
- JP
- Japan
- Prior art keywords
- amino
- triiodo
- benzenedicarboxylic acid
- acetyloxy
- solvent
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 32
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 11
- FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 19
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 11
- 238000002955 isolation Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 238000007865 diluting Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 claims description 3
- XMMFBEWONDCTLD-UHFFFAOYSA-N acetyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)C(C)=O XMMFBEWONDCTLD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical group CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- IUEVXLACZFKZSP-UHFFFAOYSA-L disodium;5-aminobenzene-1,3-dicarboxylate Chemical compound [Na+].[Na+].NC1=CC(C([O-])=O)=CC(C([O-])=O)=C1 IUEVXLACZFKZSP-UHFFFAOYSA-L 0.000 claims 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 2
- 230000001376 precipitating effect Effects 0.000 claims 2
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 claims 2
- QMADWSQEVHUFFJ-UHFFFAOYSA-N 2,4,5-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(I)=C(I)C(C(O)=O)=C1I QMADWSQEVHUFFJ-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 30
- 238000003756 stirring Methods 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IPHVGAPABXWWLO-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=C(I)C=C(I)C(C(O)=O)=C1I IPHVGAPABXWWLO-UHFFFAOYSA-N 0.000 description 2
- -1 2-hydroxy-1-oxopropyl Chemical group 0.000 description 2
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GMPOMLNJZPYPGR-VKHMYHEASA-N [(2s)-1-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-1-oxopropan-2-yl] acetate Chemical compound CC(=O)O[C@@H](C)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I GMPOMLNJZPYPGR-VKHMYHEASA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000825 ultraviolet detection Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
- UYKGCGBUVKYDJJ-UHFFFAOYSA-N 2,4,5-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC(I)=C(I)C(C(Cl)=O)=C1I UYKGCGBUVKYDJJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241001028048 Nicola Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyamides (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.次式(I): で示されるS−(−)−5−〔〔2−(アセチルオキシ)−1−オキソプロピル 〕アミノ〕−2,4,6−トリヨード−1,3−ベンゼンジカルボン酸二塩化物 の製造方法であって、S−(−)−〔2−(アセチルオキシ)〕プロピオン酸塩 化物と5−アミノ−2,4,6−トリヨード−1,3−ベンゼンジカルボン酸二 塩化物とを、非プロトン性双極性溶媒中で、ハロゲン化水素酸の存在下で反応さ せることを含む方法。 2.S−(−)−〔2−(アセチルオキシ)〕プロピオン酸塩化物を加える前に 、ハロゲン化水素酸を5−アミノ−2,4,6−トリヨード−1,3−ベンゼン ジカルボン酸二塩化物溶液にガスとして加える、請求項1記載の方法。 3.加えるハロゲン化水素酸が塩酸である、請求項1記載の方法。 4.該HClのガスを、0.1〜3のモル比率で加える請求項3記載の方法。 5.非プロトン性有機溶媒が、N,N−ジメチルアセトアミド、N,N−ジメチ ルホルムアミド及びN−メチル−2−ピロリドンからなる群から選択され、好ま しくはN,N−ジメチルアセトアミドである、請求項1〜4のいずれか1項記載 の方法。 6.HClを、ジメチルアセトアミドの塩酸塩として加える、請求項1記載の方 法。 7.ジメチルアセトアミドの塩酸塩を、0.1〜3のモル比率で加える、請求項 6記載の方法。 8.反応温度が0〜40℃の範囲である、請求項1記載の方法。 CH3CN)である、請求項1記載の方法により得られる式(I)の化合物。 10.請求項1記載のS−(−)−5−〔〔2−(アセチルオキシ)−1−オキ ソプロピル〕アミノ〕−2,4,6−トリヨード−1, 3−ベンゼンジカルボ ン酸二塩化物の精製及び単離方法であって、以下の工程: −反応混合物を、酢酸の直鎖もしくは分岐鎖(C3−C5)アルコール類とのエス テル又はモノ−、ジ−もしくはポリクロロ(C1−C4)アルカン類から選択され るものの1つで、希釈溶媒と反応混合物中の非プロトン性双極性溶媒との比0. 3:1から2.5:1w/wにおいて希釈する工程、 −希釈溶媒に対する水の比率0.5〜4w/wにおいて、水によって抽出する工程 、 −生成物を水で沈殿させる工程 を含む方法。 11.請求項10記載のS−(−)−5−〔〔2−(アセチルオキシ)−1−オ キソプロピル〕アミノ〕−2,4,6−トリヨード−1,3−ベンゼンジカルボ ン酸二塩化物の精製及び単離方法であって、溶媒が、プロピルアセタート、n− ブチルアセタート及びメチルクロロホルムから選択される方法。 12.請求項10及び11記載のS−(−)−5−〔〔2−(アセチルオ キシ)−1−オキソプロピル〕アミノ〕−2,4,6−トリヨード−1,3−ベ ンゼンジカルボン酸二塩化物の精製及び単離方法であって、水による抽出が、希 釈に用いるのと同じ溶媒及び水を端部に、希釈された混合物が中間プレート上に 充填された連続式抽出器で実施され、生成物は溶媒相の濃縮により単離される方 法。 13.請求項1記載のS−(−)−5−〔〔2−(アセチルオキシ)−1−オキ ソプロピル〕アミノ〕−2,4,6−トリヨード−1,3−ベンゼンジカルボン 酸二塩化物の精製及び単離方法であって、以下の工程: −反応混合物中に存在する非プロトン性双極性溶媒に対する希釈溶媒の比率0〜 1.5w/wにおいて、直鎖もしくは分岐鎖(C3−C5)アルコールで反応混合物 を希釈する工程、 −生成物を水で沈殿させる工程 を含む方法。 14.請求項1記載のS−(−)−5−〔〔2−(アセチルオキシ)−1−オキ ソプロピル〕アミノ〕−2,4,6−トリヨード−1,3−ベンゼンジカルボン 酸二塩化物の精製及び単離方法であって、以下の工程: −反応混合物中に存在する非プロトン性双極性溶媒に対する希釈溶媒の比率0〜 1.5w/wにおいて、直鎖もしくは分岐鎖(C3−C5)アルコールを含有する水 −アルコール溶液に、反応混合物を加える工程を含む方法。 15.請求項13及び14記載のS−(−)−5−〔〔2−(アセチルオキシ) −1−オキソプロピル〕アミノ〕−2,4,6−トリヨード−1,3−ベンゼン ジカルボン酸二塩化物の精製及び単離方法であって、アルコールが、イソプロパ ノール、tert−ブタノール及びsec−ブタノールからなる群から選択される方法 。 16.請求項14及び15記載のS−(−)−5−〔〔2−(アセチルオキシ) −1−オキソプロピル〕アミノ〕−2,4,6−トリヨード−1,3−ベンゼン ジカルボン酸二塩化物の精製及び単離方法であって、アルコールの量が、反応混 合物中の非プロトン性双極性溶媒に対する希釈溶媒の比率0.3〜0.6w/wの 範囲である、請求項14又は15記載の方法。 17.請求項10〜16記載のS−(−)−5−〔〔2−(アセチルオキシ)− 1−オキソプロピル〕アミノ〕−2,4,6−トリヨード−1,3−ベンゼンジ カルボン酸二塩化物の精製及び単離方法であって、反応混合物中に存在する非プ ロトン性双極性溶媒が、N,N′−ジメチルアセトアミドである方法。 18.S−(−)−5−〔〔2−(アセチルオキシ)−1−オキソプロピル〕ア ミノ〕−2,4,6−トリヨード−1,3−ベンゼンジカルボン酸二塩化物の製 造方法であって、以下の工程: a)中性又は塩基性条件下で5−ニトロ−1,3−ベンゼンジカルボン酸を接触 水素化して5−アミノ−1,3−ベンゼンジカルボン酸ナトリウム塩の水溶液を 得る工程、 b)a)工程から得られる5−アミノ−1,3−ベンゼンジカルボン酸ナトリウ ム塩の溶液を、さらなる精製なしに、HCl中のICl溶液により直接にヨウ素 化して、5−アミノ−2,4,6−トリヨード−1,3−ベンゼンジカルボン酸 を得る工程であって、ここで、5−アミノ−1,3−ベンゼンジカルボン酸ナト リウム塩溶液に前もってHClとH2SO4を加えておく工程、 c)5−アミノ−2,4,6−トリヨード−1,3−ベンゼンジカルボン酸二塩 化物の塩素化を、5−アミノ−2,4,6−トリヨード−1,3− ベンゼンジカルボン酸とチオニルクロリドとを不均質相で、直鎖もしくは分岐鎖 (C7〜C16)炭化水素、(C7〜C8)芳香族炭化水素、1,1,1−トリクロ ロエタン、n−ブチルアセタート及びジグリム(ジエチレングリコールジメチル エーテル)から選択される溶媒中、触媒量の第三級アミンの存在下で実施して、 5−アミノ−2,4,6−トリヨード−1,3−ベンゼンジカルボン酸二塩化物 を得る工程、 d)S−(−)−2−(アセチルオキシ)〕プロピオン酸塩化物と5−アミノ− 2,4,6−トリヨード−1,3−ベンゼンジカルボン酸二塩化物とを、非プロ トン性双極性溶媒中、ハロゲン化水素酸の存在下で反応させる工程 を含む方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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ITMI951048A IT1274550B (it) | 1995-05-23 | 1995-05-23 | Processo per la preparazione del dicloruro dell'acido s-5-¬¬2- (acetilossi)-1-ossopropil|ammino|-2,4,6-triiodo-1,3- benzendicarbossilico |
IT95A001048 | 1995-08-04 | ||
IT95RM000548 IT1281319B1 (it) | 1995-08-04 | 1995-08-04 | Procedimento per la preparazione di dicloruro dell'acido s-5-<<2- (acetilossi)-1-ossopropil>ammino>-2,4,6-triiodo-1,3-benzendi- |
IT95A000548 | 1995-08-04 | ||
PCT/EP1996/002104 WO1996037460A1 (en) | 1995-05-23 | 1996-05-17 | Process for the preparation of a dicarboxylic acid dichloride |
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JPH10503529A true JPH10503529A (ja) | 1998-03-31 |
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JP2007160804A Expired - Lifetime JP4675355B2 (ja) | 1995-05-23 | 2007-06-19 | ジカルボン酸二塩化物の製造方法 |
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US (1) | US5672735A (ja) |
EP (1) | EP0773925B1 (ja) |
JP (2) | JP4012567B2 (ja) |
KR (1) | KR100269080B1 (ja) |
CN (1) | CN1068582C (ja) |
AT (1) | ATE189674T1 (ja) |
AU (1) | AU698623B2 (ja) |
BR (1) | BR9606394A (ja) |
CA (1) | CA2195634C (ja) |
CZ (1) | CZ290363B6 (ja) |
DE (2) | DE69606601T2 (ja) |
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GR (1) | GR970300028T1 (ja) |
HU (1) | HU216537B (ja) |
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IT1289521B1 (it) * | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la purificazione di un intermedio |
IT1289520B1 (it) * | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
IT1289519B1 (it) * | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
EP2230227A1 (en) | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Process for the preparation of triiodinated carboxylic aromatic derivatives |
EP2243767A1 (en) | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Process for the iodination of aromatic compounds |
PT105770B (pt) * | 2011-06-24 | 2013-07-08 | Hovione Farmaciencia S A | Novo intermediário e seu uso na preparação de agente de contrate triiodado |
EP2931696B1 (en) | 2012-12-11 | 2018-08-22 | Bracco Imaging S.p.A | Continuous process for the preparation of (s)-2-acetyloxypropionic acid |
LT3066071T (lt) | 2013-11-05 | 2018-09-10 | Bracco Imaging S.P.A. | Jopamidolio gamybos būdas |
HUE049284T2 (hu) | 2014-06-10 | 2020-09-28 | Bracco Imaging Spa | Eljárás (S)-2-acetiloxipropionsav és származékai elõállítására |
CN110023279B (zh) | 2016-12-05 | 2022-03-11 | 伯拉考成像股份公司 | 放射照相剂中间体的机械化学合成 |
FR3062850B1 (fr) | 2017-02-10 | 2020-01-31 | Guerbet | Procede de preparation monotope de composes organo-iodes |
FR3084668A1 (fr) | 2018-08-02 | 2020-02-07 | Guerbet | Procede de preparation monotope de composes organo-iodes intermediaires a la synthese du ioversol |
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CH608189A5 (ja) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
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DE2909439A1 (de) * | 1979-03-08 | 1980-09-18 | Schering Ag | Neue nichtionische roentgenkontrastmittel |
IT1256162B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
IT1274027B (it) * | 1994-03-03 | 1997-07-14 | Zambon Spa | Processo per la preparazione e purificazione di mezzi di contrasto iodurati |
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