JPH01131141A - Purification of 3,5-diacylamino-2,4,6-triiodobenzoic acids - Google Patents
Purification of 3,5-diacylamino-2,4,6-triiodobenzoic acidsInfo
- Publication number
- JPH01131141A JPH01131141A JP28830987A JP28830987A JPH01131141A JP H01131141 A JPH01131141 A JP H01131141A JP 28830987 A JP28830987 A JP 28830987A JP 28830987 A JP28830987 A JP 28830987A JP H01131141 A JPH01131141 A JP H01131141A
- Authority
- JP
- Japan
- Prior art keywords
- water
- diacylamino
- acid
- alcohol
- weight
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 18
- 150000007513 acids Chemical class 0.000 title claims description 7
- 238000000746 purification Methods 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000012046 mixed solvent Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 150000001559 benzoic acids Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- 238000001953 recrystallisation Methods 0.000 abstract description 6
- 238000003916 acid precipitation Methods 0.000 abstract description 3
- 239000002872 contrast media Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000001990 intravenous administration Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 150000001447 alkali salts Chemical class 0.000 abstract 1
- 229940039231 contrast media Drugs 0.000 abstract 1
- 239000012264 purified product Substances 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000011084 recovery Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 3
- XCNHOBHCZBIGJP-UHFFFAOYSA-N 3-acetamido-5-amino-2,4,6-triiodobenzoic acid Chemical compound CC(=O)NC1=C(I)C(N)=C(I)C(C(O)=O)=C1I XCNHOBHCZBIGJP-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical compound [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、３．５−ジアシルアミノ−２，４，６−）リ
ヨード安息香酸ＩＩ（以下、ＤＡｃ ＢＡ類と略する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to 3,5-diacylamino-2,4,6-)lyodobenzoic acid II (hereinafter abbreviated as DAc BAs).
）の精製方法に関する。).
本発明により得られるＤＡＣＨＡ類は、静脈内毒性の極
めて低いレントゲン造影剤の中間体として有用である。DACHAs obtained according to the present invention are useful as intermediates for X-ray contrast agents with extremely low intravenous toxicity.
ＤＡＣＨＡ類を製造する方法は、特公昭３４−６２ 、
ジャーナル・オプ・ザ・エイオーエイシーＵｏｕｒｎａ
ｌｏｆ ｔｈｅ ＡＯＡＣ，Ｖｏｌ、６１．Ｎｏ、１
．１９７８）等に述べられているが、精製方法について
の説明は少ない。The method for producing DACHAs is described in Japanese Patent Publication No. 34-62,
Journal of the ACA Uourna
lo of the AOAC, Vol, 61. No.1
．． (1978), etc., but there is little explanation about the purification method.
然も、医薬品中間体としての高品質（低毒性）を確保す
ることに言及した精製方法は殆どない。However, there are almost no purification methods that mention ensuring high quality (low toxicity) as a pharmaceutical intermediate.
僅かに、水又はメタノール、エタノール等の有！ｌ！溶
剤からの再結晶や、ナトリウム塩やアンモニウム塩にし
てから、強酸を用いて再沈澱させる方法等が知られてい
るにすぎなかった。Contains a small amount of water, methanol, ethanol, etc.! l! The only known methods were recrystallization from a solvent or reprecipitation using a strong acid after converting it into a sodium salt or ammonium salt.
ＯＡ、 ＢＡ類は、殆ど医薬原体と同じ取扱いを受ける
レントゲン造影剤の中間体である。OA and BAs are intermediates for X-ray contrast agents that are treated almost in the same way as drug substances.
従って、求められる品質は極めて高く、特に分子内に未
反応アミノ基が残存するもの、例えば３−アミノ−５−
アセチルアミノ−２，４，６−）リョード安息香酸類等
は体内毒性を示すため、極めて厳しく規制されており、
従来の精製技術では高純度品を得ようとすれば再結晶や
酸析を繰り返さざるを得ず、収率の低下を余儀無くされ
ていた。Therefore, the quality required is extremely high, especially those with unreacted amino groups remaining in the molecule, such as 3-amino-5-
Acetylamino-2,4,6-) rhodobenzoic acids are highly regulated as they are toxic to the body.
With conventional purification techniques, in order to obtain a highly pure product, it is necessary to repeat recrystallization and acid precipitation, which inevitably leads to a decrease in yield.
〔問題点を解決するための手段及び作用〕本発明者らは
、前記問題点を解決するため鋭意検討した結果、水とア
ルコール類との割合（重量比）がｌ：９〜９：１である
混合溶媒中で再結晶させることで、本目的が達成できる
ことを見出し、本発明を完成させるに至った。[Means and effects for solving the problem] As a result of intensive studies to solve the above problem, the present inventors found that the ratio (weight ratio) of water to alcohol is 1:9 to 9:1. It was discovered that this object could be achieved by recrystallizing in a certain mixed solvent, and the present invention was completed.
皿ち、本発明は、
式
（式中、Ｒ，、Ｒｇは低級アルキル基で、Ｒ１、Ｒ１の
炭素数は１〜２である。）で表される、３．５−ジアシ
ルアミノ−２，４，６−トリヨード安息香酸類の精製方
法において、水とアルコール類の混合溶媒中で再結晶す
ることを特徴とする、３．５−ジアシルアミノ−２，４
，６−）リョード安息香酸類の精製方法である。The present invention provides 3,5-diacylamino-2, A method for purifying 4,6-triiodobenzoic acids, characterized by recrystallizing in a mixed solvent of water and alcohols, 3,5-diacylamino-2,4
, 6-) A method for purifying lyodobenzoic acids.
本発明を詳述すれば、本発明は、ＤＡ、 ＢＡＩを水酸
化ナトリウムや水酸化アンモニウム等で各々の塩とし水
溶解性をもたせて、これに水とアルコール類を加えて濃
度を５〜６０重量％に調製（水とアルコール類は各々１
：９〜９：１の重量比になるようにする）し、更に加熱
、溶解した後、室温まで冷却して結晶を析出させ、これ
を濾過して高純度の口ＡＣＢＡＩｉを得る、ＤＡＣＢＡ
Ｉｊｌの精製方法である。More specifically, the present invention involves salting DA and BAI with sodium hydroxide, ammonium hydroxide, etc. to make them water-soluble, and adding water and alcohol to the salts to a concentration of 5 to 60%. Adjusted to 1% by weight (1% each for water and alcohol)
:9 to 9:1 weight ratio), further heated and dissolved, cooled to room temperature to precipitate crystals, and filtered to obtain high purity ACBAIi.
This is a method for purifying Ijl.
ＤＡＣＢＡｌｉｌの塩は、前記の他にカリウム塩、カル
シウム塩やジェタノール塩等水溶性をもつものならば何
でも良い。この濃度は５〜６０重量％であるが、好まし
くは１０〜３０重量％である。濃度６０重世％を超える
と塩の溶解度の関係上、未溶解分が残り再結晶操作が困
難となる。又濃度５重量％未満では結晶の析出が難しく
なり、収率が著しく低下する。In addition to the above-mentioned salts, any salts of DACBAlil may be used as long as they are water-soluble, such as potassium salts, calcium salts, and jetanol salts. This concentration is between 5 and 60% by weight, preferably between 10 and 30% by weight. If the concentration exceeds 60%, undissolved matter remains due to the solubility of the salt, making recrystallization difficult. Further, if the concentration is less than 5% by weight, precipitation of crystals becomes difficult and the yield decreases significantly.
アルコール類には、特に制限はないが、炭素数が多すぎ
ると溶解度の関係上問題があるので、好ましくは炭素数
４以下のアルコール、例えばメチルアルコール、エチル
アルコール、２−プロピルアルコール等が良い。There are no particular restrictions on the alcohol, but since too many carbon atoms pose problems in terms of solubility, alcohols with 4 or less carbon atoms, such as methyl alcohol, ethyl alcohol, and 2-propyl alcohol, are preferred.
アルコール類の水に対する割合は、１０〜９０重量％で
あるが、好ましくは３０〜７０重量％である。The ratio of alcohol to water is 10 to 90% by weight, preferably 30 to 70% by weight.
アルコール類は、ＤＡＣＢＡ類の塩が極めて大きな水溶
解性をもつため、それを取扱い易い溶解度に調製するた
めに用いられるもので、アルコール類の割合が１０重量
％未満ならば溶解度が大き過ぎ、９０重量％を超えると
逆に溶解度が小さ（なり過ぎて、いずれも再結晶に困難
を生じる。Since the salts of DACBAs have extremely high water solubility, alcohols are used to adjust the solubility to a level that is easy to handle.If the proportion of alcohol is less than 10% by weight, the solubility is too high; On the contrary, if it exceeds % by weight, the solubility becomes too small (too much), making recrystallization difficult.
加熱溶解時の温度は、３０°Ｃから溶媒の還流温度の間
で結晶の溶解する温度である。The temperature during heating and dissolution is between 30° C. and the reflux temperature of the solvent, at which the crystals dissolve.
濾過温度は、４０″Ｃ以下で室温付近が最も良く、１０
℃未満に下げても効果は変わらない。The best filtration temperature is 40″C or below, around room temperature, and 10
Even if the temperature is lowered below ℃, the effect remains the same.
以下、実施例により本発明を更に具体的に説明する。 Hereinafter, the present invention will be explained in more detail with reference to Examples.
分析法について、３，５−ジアシルアミノ−２，４，６
−トリヨード安息香酸類の純度は、液体クロマトグラフ
ィーのピーク面積比から求めた。又、３−アミノ−５−
アシルアミノ−２，４，６−トリヨード安息香酸は未反
応アミノ基を亜硝酸ナトリウムとＮ−（１−ナフチル）
エチレンジアミン塩酸塩でジアゾカンプリング化し、発
色させて吸光度を測定する方法で定量した（ブリテラシ
ュ・ファルマコピア（Ｂｒｉｔｉｓｈ Ｐｈａｒｍａｃ
ｏｐｏｅａ ） ’７３）。Regarding the analytical method, 3,5-diacylamino-2,4,6
- The purity of triiodobenzoic acids was determined from the peak area ratio of liquid chromatography. Also, 3-amino-5-
Acylamino-2,4,6-triiodobenzoic acid converts the unreacted amino group into sodium nitrite and N-(1-naphthyl).
Quantification was performed by diazocamping with ethylenediamine hydrochloride, developing color, and measuring absorbance (British Pharmacopia).
opoea) '73).
回収率は以下の式から求めた。The recovery rate was calculated from the following formula.
実施例１
粗製３．５−ジアセチルアミノ−２，４，６−トリヨー
ド安息香酸０．１モルを５重量％水酸化ナトリウム水溶
液で完全に溶解し、この濃度が２５重量％になるように
、更に水と２−プロピルアルコールを加えた。Example 1 0.1 mol of crude 3,5-diacetylamino-2,4,6-triiodobenzoic acid was completely dissolved in a 5% by weight aqueous sodium hydroxide solution, and further dissolved so that the concentration was 25% by weight. Water and 2-propyl alcohol were added.
このとき、２−プロピルアルコールは全水量に対して６
０重量％に相当する量を加えた。At this time, 2-propyl alcohol is 6% of the total amount of water.
An amount corresponding to 0% by weight was added.
その後、約６０″Ｃまで昇温し結晶を完全に溶解した後
、ゆっくりと室温まで冷却し結晶を析出させた。この結
晶を濾別し、減圧乾燥器でｔｏｏ ’Ｃ１３時間乾燥し
た。Thereafter, the temperature was raised to about 60''C to completely dissolve the crystals, and then the mixture was slowly cooled to room temperature to precipitate crystals.The crystals were filtered off and dried in a vacuum dryer for 13 hours at too low a temperature.
その結果、結晶純度は９８．０％から９９．８８％に、
３−アミノ−５−アセチルアミノ−２，４，６−トリヨ
ード安息香酸は７００ｐｐｍから１０ｐｐｍにすること
ができた。As a result, the crystal purity increased from 98.0% to 99.88%.
The concentration of 3-amino-5-acetylamino-2,4,6-triiodobenzoic acid could be reduced from 700 ppm to 10 ppm.
このときの回収率は９０．５％であった。The recovery rate at this time was 90.5%.
実施例２
粗製３．５−ジアセチルアミノ−２，４，６−）リョー
ド安患香酸０．１モルを５重量％水酸化ナトリウム水溶
液で完全に溶解し、この濃度が３０重量％になるように
、更に水と２−プロピルアルコールを加えた。Example 2 0.1 mol of crude 3,5-diacetylamino-2,4,6-)lyodobenzoic acid was completely dissolved in a 5% by weight aqueous sodium hydroxide solution, and the concentration was adjusted to 30% by weight. To this, water and 2-propyl alcohol were further added.
このとき、２−プロピルアルコールは全水量に対して４
０重量％に相当する量を加えた。At this time, 2-propyl alcohol is 4% of the total amount of water.
An amount corresponding to 0% by weight was added.
その後、約６０°Ｃまで昇温し結晶を完全に溶解した後
、ゆっ（りと室温まで冷却し結晶を析出させた。この結
晶を濾別し、減圧乾燥器で１００°Ｃ，３時間乾燥した
。Thereafter, the temperature was raised to about 60°C to completely dissolve the crystals, and then slowly cooled to room temperature to precipitate crystals. The crystals were filtered off and dried at 100°C in a vacuum dryer for 3 hours. did.
その結果、結晶純度は９８．０％から９９．７３％に、
３−アミノ−５−アセチルアミノ−２，４，６−）リョ
ード安患香酸は７１ｏｐｐｍから１５ｐｐｍにすること
ができた。As a result, the crystal purity increased from 98.0% to 99.73%.
3-Amino-5-acetylamino-2,4,6-) rhodobenzoic acid could be reduced from 71 oppm to 15 ppm.
このときの回収率は８８．１％であった。The recovery rate at this time was 88.1%.
比較例１
３．５−ジアセチルアミノ−２，４，６−）リョード安
息香酸の濃度が３重量％になるように水と２＝プロピル
アルコールを加えた以外は全て実施例１と同じ条件で行
って以下の結果を得た。Comparative Example 1 Everything was carried out under the same conditions as in Example 1 except that water and 2=propyl alcohol were added so that the concentration of 3.5-diacetylamino-2,4,6-) rhodobenzoic acid was 3% by weight. The following results were obtained.
結晶純度は９８．０％から９９．５０％に、３−アミノ
−５−アセチルアミノ−２，４，６−）リョード安息香
酸を７１０ｐｐａ＋から３５ｐｐｍにすることができた
。このときの回収率は１２．２％であった。The crystal purity could be increased from 98.0% to 99.50%, and the 3-amino-5-acetylamino-2,4,6-)ryodobenzoic acid could be increased from 710 ppa+ to 35 ppm. The recovery rate at this time was 12.2%.
比較例２
２−プロピルアルコールの水に対する割合を４重量％に
した以外は全て実施例１と同じ条件で行って、以下の結
果を得た。Comparative Example 2 The following results were obtained under the same conditions as in Example 1 except that the ratio of 2-propyl alcohol to water was 4% by weight.
結晶純度は９８．０％から９９．２４％に、３−アミノ
−５−アセチルアミノ−２，４，６−）リョード安息香
酸を７１０ｐｐｍから７０ｐｐｍにすることができた。The crystal purity could be increased from 98.0% to 99.24%, and 3-amino-5-acetylamino-2,4,6-) rhodobenzoic acid could be increased from 710 ppm to 70 ppm.
このときの回収率は８５．２％であった。The recovery rate at this time was 85.2%.
実施例３
実施例１において、２−プロピルアルコールの代わりに
メチルアルコールを用いて精製した。Example 3 In Example 1, methyl alcohol was used instead of 2-propyl alcohol for purification.
その結果、結晶純度は９８．０％から９９．３１％に、
３−アミノ−５−アセチルアミノ−２，４，６−トリヨ
ード安息香酸は７１０ｐｐｍから５５ｐｐ＋ａにするこ
とができた。As a result, the crystal purity increased from 98.0% to 99.31%.
3-Amino-5-acetylamino-2,4,6-triiodobenzoic acid could be reduced from 710 ppm to 55 pp+a.
このときの回収率は７９．９％であった。The recovery rate at this time was 79.9%.
実施例４
粗製３．５−ジプロピオンアミド−２，４，６−）リョ
ード安患香酸０．１モルを５重量％水酸化ナトリウム水
溶液で完全に溶解し、この濃度が２０重量％になるよう
に、更に水と２−プロピルアルコールを加えた。このと
きの２−プロピルアルコールは全水量に対して６０重量
％に相当する量を加えた。Example 4 0.1 mol of crude 3,5-dipropionamide-2,4,6-)lyodobenzoic acid is completely dissolved in a 5% by weight aqueous sodium hydroxide solution, resulting in a concentration of 20% by weight. Then, more water and 2-propyl alcohol were added. At this time, 2-propyl alcohol was added in an amount equivalent to 60% by weight based on the total amount of water.
以下、実施例１と同様の操作で以下の結果を得た。Hereinafter, the following results were obtained by the same operation as in Example 1.
結晶純度は９６．３％から９９．６％に、３−アミノ−
５−ブロピオンアミド−２，４，６−）リョード安患香
酸を９３ｏｐｐ−から’７５ｐｐｍにすることができた
。このときの回収率は９１．５％であった。Crystal purity from 96.3% to 99.6%, 3-amino-
5-propionamide-2,4,6-) rhodobenzoic acid could be reduced from 93 opp- to '75 ppm. The recovery rate at this time was 91.5%.
本発明の方法によれば、強酸を用いた酸析及び再結晶を
繰り返すことなく高純度の３．５−ジアシルアミノ−２
，４，６−トリヨード安息香酸類を収率良く精製するこ
とができる。According to the method of the present invention, highly pure 3,5-diacylamino-2 can be obtained without repeating acid precipitation using a strong acid and recrystallization.
, 4,6-triiodobenzoic acids can be purified with good yield.
特許出願人 三井東圧化学株式会社Patent applicant: Mitsui Toatsu Chemical Co., Ltd.
Claims (1)
Ｒ＿２の炭素数は１〜２である。）で表される、３，５
−ジアシルアミノ−２，４，６−トリヨード安息香酸類
の精製方法において、水とアルコール類の混合溶媒中で
再結晶することを特徴とする、３，５−ジアシルアミノ
−２，４，６−トリヨード安息香酸類の精製方法。[Claims] 1 Formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 and R_2 are lower alkyl groups, R_1,
The number of carbon atoms in R_2 is 1 to 2. ), 3,5
- A method for purifying diacylamino-2,4,6-triiodobenzoic acids, comprising recrystallizing 3,5-diacylamino-2,4,6-triiodo in a mixed solvent of water and alcohols. Method for purifying benzoic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28830987A JPH01131141A (en) | 1987-11-17 | 1987-11-17 | Purification of 3,5-diacylamino-2,4,6-triiodobenzoic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28830987A JPH01131141A (en) | 1987-11-17 | 1987-11-17 | Purification of 3,5-diacylamino-2,4,6-triiodobenzoic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01131141A true JPH01131141A (en) | 1989-05-24 |
Family
ID=17728506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28830987A Pending JPH01131141A (en) | 1987-11-17 | 1987-11-17 | Purification of 3,5-diacylamino-2,4,6-triiodobenzoic acids |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01131141A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111187179A (en) * | 2020-01-20 | 2020-05-22 | 上海新华联制药有限公司 | Purification method of diatrizoic acid crude product |
-
1987
- 1987-11-17 JP JP28830987A patent/JPH01131141A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111187179A (en) * | 2020-01-20 | 2020-05-22 | 上海新华联制药有限公司 | Purification method of diatrizoic acid crude product |
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