公开(公告)号：KR100450607B1

公开(公告)日：2004-09-30

申请号：KR1020020040324

申请日：2002-07-11

Applicant: 한국과학기술연구원 ,  경동제약 주식회사

Inventor： 정찬성 ,  이소하 ,  문만식 ,  전숙진 ,  이병석

IPC: C07H15/222

Abstract: PURPOSE: A process for preparing Gallamine derivative is provided, thereby cheaply preparing the Gallamine derivative which is useful in synthesis of aminoglycoside antibiotics including isepamycin. CONSTITUTION: A process for preparing Gallamine derivative of the formula(4) comprises the steps of: introducing acetyl(-Ac) or benzyloxycarbonyl(-Cbz) into the amine group of 3,2',6'-NH2 of sisomicin or gentamicin to prepare a compound of the formula(1); reacting the amine group of 1-NH2 of the compound of the formula(1) with anhydride of acid represented by YOH or acid derivative thereof to prepare a compound of the formula(2); introducing acetyl(-Ac) or benzyloxycarbonyl(-Cbz) into the amine group of 3'-NH2 of the compound of the formula(2) to prepare a compound of the formula(3); and reacting the compound of the formula(3) under acid condition to remove purpurosamine or sisosamine ring to prepare the Gallamine derivative of the formula(4), wherein R1 and R2 are independently hydrogen or methyl; X is acetyl or benzyloxycarbonyl; Y is C1 to C10 alkylcarbonyl, or amino or hydroxy substituted C1 to C10 alkylcarbonyl.

Abstract translation: 目的：提供了一种制备Gallamine衍生物的方法，由此便宜地制备了用于合成氨基糖苷类抗生素（包括异阿霉素）的Gallamine衍生物。 构成：制备式（4）的Gallamine衍生物的方法包括以下步骤：将乙酰基（-Ac）或苄氧基羰基（-Cbz）引入西索米星或庆大霉素的3,2'，6'-NH 2的胺基中， 制备式（1）的化合物; 使式（1）化合物的1-NH 2的胺基与由YOH或其酸衍生物表示的酸的酸酐反应以制备式（2）的化合物; 在式（2）化合物的3'-NH 2的胺基中引入乙酰基（-Ac）或苄氧基羰基（-Cbz）以制备式（3）的化合物; （3）的化合物在酸性条件下反应以除去紫苏糖胺或sisosamine环以制备式（4）的Gallamine衍生物，其中R 1和R 2独立地为氢或甲基; X是乙酰基或苄氧基羰基; Y是C1至C10烷基羰基，或氨基或羟基取代的C1至C10烷基羰基。

公开(公告)号：KR1020020059999A

公开(公告)日：2002-07-16

申请号：KR1020010001195

申请日：2001-01-09

Applicant: 한국과학기술연구원

Inventor： 정찬성 ,  이소하 ,  문만식

IPC: C07D213/68

Abstract: PURPOSE: A method for preparing 2-acetylnicotinic acid is provided to improve the deoxygenating process, thereby reducing the environmental pollution and the manufacturing cost and enhancing production yield and purity. CONSTITUTION: The method comprises the steps of acetylating nicotinic acid N-oxide, deoxygenating the acetylated compound; and treating the deoxygenated compound with an alkali or acid aqueous solution to obtain 2-acetylnicotinic acid, wherein the deoxygenation is carried out by using an alcohol solvent and a Pd/C catalyst under the hydrogen gas atmosphere. Preferably the deoxygenation is carried out at 0.5-3 % Pd/C catalyst in alcohols and at a hydrogen gas pressure of 1-10 atm.

Abstract translation: 目的：提供2-乙酰烟酸的制备方法，以改善脱氧过程，减少环境污染和制造成本，提高产量和纯度。 方法：该方法包括乙酰化烟酸N-氧化物，脱乙酰化化合物的步骤; 用碱或酸水溶液处理脱氧化合物，得到2-乙酰烟酸，其中，在氢气气氛下使用醇溶剂和Pd / C催化剂进行脱氧。 优选地，脱氧在0.5-3％Pd / C催化剂的醇中和氢气压力为1-10atm下进行。

公开(公告)号：KR1020040006306A

公开(公告)日：2004-01-24

申请号：KR1020020040324

申请日：2002-07-11

Applicant: 한국과학기술연구원 ,  경동제약 주식회사

Inventor： 정찬성 ,  이소하 ,  문만식 ,  전숙진 ,  이병석

IPC: C07H15/222

Abstract: PURPOSE: A process for preparing Gallamine derivative is provided, thereby cheaply preparing the Gallamine derivative which is useful in synthesis of aminoglycoside antibiotics including isepamycin. CONSTITUTION: A process for preparing Gallamine derivative of the formula(4) comprises the steps of: introducing acetyl(-Ac) or benzyloxycarbonyl(-Cbz) into the amine group of 3,2',6'-NH2 of sisomicin or gentamicin to prepare a compound of the formula(1); reacting the amine group of 1-NH2 of the compound of the formula(1) with anhydride of acid represented by YOH or acid derivative thereof to prepare a compound of the formula(2); introducing acetyl(-Ac) or benzyloxycarbonyl(-Cbz) into the amine group of 3'-NH2 of the compound of the formula(2) to prepare a compound of the formula(3); and reacting the compound of the formula(3) under acid condition to remove purpurosamine or sisosamine ring to prepare the Gallamine derivative of the formula(4), wherein R1 and R2 are independently hydrogen or methyl; X is acetyl or benzyloxycarbonyl; Y is C1 to C10 alkylcarbonyl, or amino or hydroxy substituted C1 to C10 alkylcarbonyl.

Abstract translation: 目的：提供制备Gallamine衍生物的方法，从而廉价地制备可用于合成氨基糖苷类抗生素（包括伊曲霉素）的加仑胺衍生物。 构成：制备式（4）的加仑胺衍生物的方法包括以下步骤：将乙酰基（-Ac）或苄氧羰基（-Cbz）引入西索米星或庆大霉素的3,2'，6'-NH2的胺基中 制备式（1）化合物; 使式（1）化合物的1-NH 2的胺基与由YOH或其酸衍生物表示的酸的酸酐反应以制备式（2）的化合物; 将乙酰基（-Ac）或苄氧羰基（-Cbz）引入式（2）化合物的3'-NH 2的胺基中以制备式（3）化合物; 并在酸性条件下使式（3）的化合物反应以除去嘌呤胺或者sisosamine环以制备式（4）的Gallamine衍生物，其中R 1和R 2独立地是氢或甲基; X是乙酰基或苄氧基羰基; Y为C1至C10烷基羰基，或氨基或羟基取代的C1至C10烷基羰基。

公开(公告)号：KR1020040029575A

公开(公告)日：2004-04-08

申请号：KR1020020059879

申请日：2002-10-01

Applicant: 한국과학기술연구원 ,  경동제약 주식회사

Inventor： 정찬성 ,  이소하 ,  문만식 ,  전숙진 ,  이병석

IPC: C07H15/23

Abstract: PURPOSE: A process for producing isepamicin is provided, thereby improving the production yield of isepamicin which is used as an antibiotics via garamine derivatives as an intermediate. CONSTITUTION: A process for producing isepamicin represented by the formula(8) comprises the steps of: introducing acetyl group(-Ac) or benzyloxycarbonyl group(-Cbz) to 3,2',6'-NH2 group of sisomicin or gentamicin to prepare a compound of the formula(1); binding of 1-NH2 group of a compound of the formula(1) with isoserine derivative of the formula(2) to prepare a compound of the formula(3); introducing acetyl group(-Ac) or benzyloxycarbonyl group(-Cbz) to 3'-NH2 group of the compound of the formula(3) to prepare a compound of the formula(4); reacting the compound of the formula(4) under acid condition to remove purpurosamine or sisosamine ring to prepare garamine derivative of the formula(5); reacting the garamine derivative of the formula(5) with glycosyl chloride of the formula(6) to prepare a compound of the formula(7); and reacting the compound of the formula(7) under palladium/carbon catalyst and hydrogen, wherein R1 and R2 are independently hydrogen or methyl; and X is acetyl group(-Ac) or benzyloxycarbonyl group(-Cbz).

Abstract translation: 目的：提供生产异环霉素的方法，从而提高作为中间体的大蒜胺衍生物作为抗生素使用的异环霉素的产率。 构成：由式（8）表示的生产异环霉素的方法包括以下步骤：将乙酰基（-Ac）或苄氧基羰基（-Cbz）引入西索米星或庆大霉素的3,2'，6'- 式（1）的化合物; 式（1）化合物的1-NH 2基团与式（2）的异丝氨酸衍生物的结合以制备式（3）的化合物; 将式（3）化合物的乙酰基（-Ac）或苄氧基羰基（-Cbz）引入3'-NH 2基团以制备式（4）的化合物; 在酸性条件下使式（4）的化合物反应以除去嘌呤胺或者sisosamine环以制备式（5）的甘胺衍生物; 使式（5）的甘胺衍生物与式（6）的糖基氯反应以制备式（7）化合物; 并在钯/碳催化剂和氢气下使式（7）化合物反应，其中R 1和R 2独立地是氢或甲基; X为乙酰基（-Ac）或苄氧基羰基（-Cbz）。

公开(公告)号：KR100467506B1

公开(公告)日：2005-01-24

申请号：KR1020020059879

申请日：2002-10-01

Applicant: 한국과학기술연구원 ,  경동제약 주식회사

Inventor： 정찬성 ,  이소하 ,  문만식 ,  전숙진 ,  이병석

IPC: C07H15/23

Abstract: PURPOSE: A process for producing isepamicin is provided, thereby improving the production yield of isepamicin which is used as an antibiotics via garamine derivatives as an intermediate. CONSTITUTION: A process for producing isepamicin represented by the formula(8) comprises the steps of: introducing acetyl group(-Ac) or benzyloxycarbonyl group(-Cbz) to 3,2',6'-NH2 group of sisomicin or gentamicin to prepare a compound of the formula(1); binding of 1-NH2 group of a compound of the formula(1) with isoserine derivative of the formula(2) to prepare a compound of the formula(3); introducing acetyl group(-Ac) or benzyloxycarbonyl group(-Cbz) to 3'-NH2 group of the compound of the formula(3) to prepare a compound of the formula(4); reacting the compound of the formula(4) under acid condition to remove purpurosamine or sisosamine ring to prepare garamine derivative of the formula(5); reacting the garamine derivative of the formula(5) with glycosyl chloride of the formula(6) to prepare a compound of the formula(7); and reacting the compound of the formula(7) under palladium/carbon catalyst and hydrogen, wherein R1 and R2 are independently hydrogen or methyl; and X is acetyl group(-Ac) or benzyloxycarbonyl group(-Cbz).

Abstract translation: 目的：提供一种生产异帕米松的方法，由此提高了通​​过作为中间体的甘氨酸衍生物作为抗生素使用的异扑霉素的产量。 结构式（8）表示的生产异帕米松的方法包括以下步骤：将乙酰基（-Ac）或苄氧基羰基（-Cbz）引入西索米星或庆大霉素的3,2'，6'-NH 2基团以制备 式（1）的化合物; 式（1）化合物的1-NH 2基团与式（2）的异丝氨酸衍生物结合以制备式（3）化合物; 向式（3）化合物的3'-NH 2基团中引入乙酰基（-Ac）或苄氧基羰基（-Cbz）以制备式（4）化合物; 在酸性条件下使式（4）化合物反应除去紫苏糖胺或sisosamine环，制备式（5）的甘氨酸衍生物; 使式（5）的甘氨酸衍生物与式（6）的糖基氯反应以制备式（7）的化合物; 和使式（7）化合物在钯/碳催化剂和氢气下反应，其中R1和R2独立地为氢或甲基; X是乙酰基（-Ac）或苄氧基羰基（-Cbz）。

公开(公告)号：KR100371087B1

公开(公告)日：2003-02-06

申请号：KR1020010001195

申请日：2001-01-09

Applicant: 한국과학기술연구원

Inventor： 정찬성 ,  이소하 ,  문만식

IPC: C07D213/68

Abstract: PURPOSE: A method for preparing 2-acetylnicotinic acid is provided to improve the deoxygenating process, thereby reducing the environmental pollution and the manufacturing cost and enhancing production yield and purity. CONSTITUTION: The method comprises the steps of acetylating nicotinic acid N-oxide, deoxygenating the acetylated compound; and treating the deoxygenated compound with an alkali or acid aqueous solution to obtain 2-acetylnicotinic acid, wherein the deoxygenation is carried out by using an alcohol solvent and a Pd/C catalyst under the hydrogen gas atmosphere. Preferably the deoxygenation is carried out at 0.5-3 % Pd/C catalyst in alcohols and at a hydrogen gas pressure of 1-10 atm.

Abstract translation: 目的：提供2-乙酰基烟酸的制备方法以改善脱氧过程，从而减少环境污染和制造成本，提高产量和纯度。 构成：该方法包括乙酰化烟酸N-氧化物，使乙酰化化合物脱氧的步骤; 用碱或酸水溶液处理脱氧化合物，得到2-乙酰基烟酸，其中脱氢反应是在氢气气氛下用醇溶剂和Pd / C催化剂进行的。 优选地，在醇中0.5-3％Pd / C催化剂和1-10个大气压的氢气压力下进行脱氧。