公开(公告)号：KR100272287B1

公开(公告)日：2000-11-15

申请号：KR1019980029486

申请日：1998-07-22

Applicant: 화일약품주식회사

Inventor： 우남태 ,  양민승 ,  우혜경 ,  김종호

IPC: C07C229/00

Abstract: 본 발명은 진통·소염제로서 유용한 하기 구조식(1)의 2-[(2,6-디클로로페닐)아미노]페닐아세톡시아세트산(아세클로페낙)의 신규 제조방법에 관한 것이다.
더욱 상세하게는 아세클로페낙에스테르를 적당한 용매에 녹이고 루이스산과 구핵제(Nucleophilic agent)의 공존하에서 반응시켜 비교적 저렴하고 안정적이며 용이한 방법으로 분리하기 어려운 분해부산물의 생성을 최소화하고 반응시간을 단축시켜 고순도의 아세클로페낙을 고수율로 제조하는 방법에 관한 것이다.

公开(公告)号：KR1020000009216A

公开(公告)日：2000-02-15

申请号：KR1019980029486

申请日：1998-07-22

Applicant: 화일약품주식회사

Inventor： 우남태 ,  양민승 ,  우혜경 ,  김종호

IPC: C07C229/00

Abstract: PURPOSE: A process for preparing 2-£(2,6-dichlorophenyl)amino|phenylacetoxyacetic acid by melting acechlophenac ester in an adequate solvent and reacting in the presence of Lewis acid and nucleophilic agent is provided which minimizes the generation of by-product and reduces the reaction time. CONSTITUTION: 2-£(2,6-Dichlorophenyl)amino|phenylacetoxyacetic acid(I) useful as an analgesia and anti-inflammatory, is manufactured by melting acechlophenac ester in a solvent and reacting with M2(X)n in the presence of R2-S-A. In a formula, R1 is a straight and side chain containing 1-5C alkyl group, aryl group, straight and side chain containing 1-5C aryl 1-5C alkyl group, tetrahydropyranyl or tetrahydrofuranyl group; M2 contains AL, Zn, Sn, Fe, Sb, Ti, and B; X is F, Cl, Br, and I; n is 2-5; R2 is H or a straight and side chain containing 1-5C alkyl group and aryl group, For an example, 7.42g acechlophenacmethylester is melted in 30ml dichloromethane, added with 10ml 2-propanethiol and 3g anhydrous aluminum chloride at room temperature for 10-30 min. The solvent is removed by distilling and the reactant is mixed with 37 ml ethyl acetate, 40 ml acetonitrile and 80 ml water to give 6.24g acechlophenac(yield:97.5%).

Abstract translation: 目的：提供一种通过在适当的溶剂中熔化乙酰化苯甲酸酯并在路易斯酸和亲核试剂存在下反应制备2-（2,6-二氯苯基）氨基|苯乙酰氧基乙酸的方法，其最小化副产物的产生和 减少反应时间。 构成：用作镇痛和抗炎的2-（2,6-二氯苯基）氨基|苯乙酰氧基乙酸（I）是通过在溶剂中熔化乙酰苯胺酯并在R2存在下与M2（X）n反应制备的 -SA。 在式中，R 1是含有1-5C烷基，芳基，含有1-5C芳基1-5C烷基的直链和侧链的直链和侧链，四氢吡喃基或四氢呋喃基; M2含有AL，Zn，Sn，Fe，Sb，Ti和B; X是F，Cl，Br和I; n为2-5; R2是H或含有1-5C烷基和芳基的直链和侧链，例如，7.42g乙烯基苯甲酸甲酯在30ml二氯甲烷中熔融，在室温下加入10ml 2-丙硫醇和3g无水氯化铝10-30 分钟。 通过蒸馏除去溶剂，将反应物与37ml乙酸乙酯，40ml乙腈和80ml水混合，得到6.24g乙酰苯胺（产率：97.5％）。

公开(公告)号：KR100319030B1

公开(公告)日：2002-01-18

申请号：KR1019990008224

申请日：1999-03-12

Applicant: 화일약품주식회사

Inventor： 우남태 ,  양민승 ,  우혜경 ,  김종호

IPC: C07C229/30

Abstract: 본발명은화학식 (A)의 4-아미노-5-헥센산(비닐 GABA)의신규제조방법, 그신규중간체화합물및 그제조방법에관한것으로, 글루타민산으로부터제조되는화학식 (I)의글루타민산-5-벤질에스테르를출발물질로사용하여신규중간체인화학식 (II), (III), (IV)를거쳐목적화합물을간단한공정으로경제적으로제조하는방법을제공한다.

公开(公告)号：KR1020000060138A

公开(公告)日：2000-10-16

申请号：KR1019990008224

申请日：1999-03-12

Applicant: 화일약품주식회사

Inventor： 우남태 ,  양민승 ,  우혜경 ,  김종호

IPC: C07C229/30

Abstract: PURPOSE: A new preparation of 4-amino-5-hexenoic acid is provided that produces economically 4-amino-5-hexenoic acid through simple processes using glutamic acid-5-benzylester as a starting material. CONSTITUTION: The preparation of 4-amino-5-hexenoic acid (vinyl γ-aminobutyric acid) comprises the step of preparing the desired compound via new intermediates of Formula (II), (III) and (IV) from glutamic acid-5-benzylester of Formula (I) derived from glutamic acid. More particularly, the preparation of 4-amino-5-hexenoic acid of Formula (A) comprises hydrolyzing 4-£(benzyloxy)carbonyl|amino-5-hexenoic acid benzyl ester £Formula (IV)| in the presence of Pd/C catalyst. The preparation of the desired compound (I) comprises the step of subjecting benzyl-4-{£(benzyloxy)carbonyl|amino}-5-oxopentanoate £Formula (III)| to a Wittig reaction. Also, the preparation of benzyl-4-{£(benzyloxy)carbonyl|amino}-5-oxopentanoate £Formula (III)| comprises the steps of reacting glutamic acid-5-benzylester £Formula (I)| with benzyl chloroformate to provide N-benzyloxycarbonyl glutamic acid-5-benzylester £Formula (II)|, and then directly reducing the compound of Formula (II) or converting the carboxyl group of the compound represented by Formula (II) to an alcohol group using NaBH4 and ethylchloroformate followed by subjecting to a Swern Oxidation.

Abstract translation: 目的：提供4-氨基-5-己烯酸的新制剂，其通过使用谷氨酸-5-苄基酯作为起始原料的简单方法生产经济地4-氨基-5-己烯酸。 构成：4-氨基-5-己烯酸（乙烯基γ-氨基丁酸）的制备包括通过式（II），（III）和（IV）的新中间体从谷氨酸-5- 式（I）的苄基酯衍生自谷氨酸。 更具体地，式（A）的4-氨基-5-己烯酸的制备包括水解4-（苄氧基）羰基|氨基-5-己烯酸苄酯，式（IV） 在Pd / C催化剂存在下。 所需化合物（I）的制备包括使苄基-4- {（（苄氧基）羰基}氨基} -5-氧代戊酸酯（III） 维特希反应。 另外，制备苄基-4- {（（苄氧基）羰基）氨基} -5-氧代戊酸酯。 包括使谷氨酸-5-苄酯与式（I）反应的步骤 用氯甲酸苄酯提供N-苄氧羰基谷氨酸-5-苄酯，式（II）|，然后直接还原式（II）化合物或将式（II）表示的化合物的羧基转化为醇基 使用NaBH 4和氯甲酸乙酯，然后进行Swern氧化。