公开(公告)号：KR1020050028094A

公开(公告)日：2005-03-22

申请号：KR1020030064383

申请日：2003-09-17

Applicant: 한국과학기술연구원

Inventor： 조용서 ,  장문호 ,  고훈영 ,  배애님 ,  강현정

IPC: C07D493/08

CPC classification number: C07D493/08

Abstract: A 7-membered cyclic compound having diexomethylene groups and a preparation method thereof are provided, which compound is useful as an intermediate for preparing other cyclic compound through Diels-Alder reaction, and has improved activity. The 7-membered cyclic compound having diexomethylene groups represented by formula (1) is provided, wherein R1 is C1-C6 alkyl; R2 and R3 are independently hydrogen; or R1, R2 and R3 together form 5- to 10-membered aliphatic or aromatic rings. The method for preparing the 7-membered cyclic compound having diexomethylene groups represented by formula (1) comprises cyclization of trimethylsilanylmethyl-alenol derivatives in the presence of Lewis acid in solvent at -90 deg. C to the room temperature, wherein the solvent is selected from diethylether, tetrahydrofuran, dichloromethane and chloroform; and the Lewis acid is trimethylsillyl trifluoromethanesulfonate(TMSOTf).

Abstract translation: 提供了具有阴离子亚甲基基团的7-元环状化合物及其制备方法，该化合物可用作通过Diels-Alder反应制备其它环状化合物的中间体，并具有改进的活性。 提供了由式（1）表示的具有正亚烷基的7-元环状化合物，其中R 1为C 1 -C 6烷基; R2和R3独立地是氢; 或R 1，R 2和R 3一起形成5至10元脂族或芳环。 由式（1）表示的具有阴离子亚甲基的7-元环状化合物的制备方法包括在路易斯酸存在下，在-90℃的溶剂中使三甲基硅烷基甲基 - 烯醇衍生物环化。 C至室温，其中溶剂选自乙醚，四氢呋喃，二氯甲烷和氯仿; 路易斯酸是三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）。

公开(公告)号：KR100465277B1

公开(公告)日：2005-01-13

申请号：KR1020020004200

申请日：2002-01-24

Applicant: 한국과학기술연구원

Inventor： 고훈영 ,  최경일 ,  조용서 ,  배애님 ,  차주환 ,  공재양 ,  정대영

IPC: C07D453/02 ,  C07D471/08 ,  C07D261/06

Abstract: PURPOSE: Azabicyclic compounds having an oxime moiety and a preparation method thereof are provided, which can be useful for treatment of cerebral nervous diseases caused by choline neurotransmission disorders including Alzheimer's disease. CONSTITUTION: An azabicyclic compounds having an oxime moiety represented by the formula(I) and pharmaceutically acceptable salts thereof are provided, wherein n is 1 or 2; m is 0 or 1; and R is at least one substituent selected from the group consisting of hydrogen, F, Cl, methoxy, OH, NH2, NO2, 3, 4-dimethoxy, 2, 4-dimethoxy, cyano, C1-C6 alkyl, 1, 2 or 3 fluorine atom substituted C1-C6 alkyl, 4-methoxybenzyloxy, t-butoxycarbonyl, C2-C6 alkenyl, 1, 2 or 3 fluorine atom substituted C2-C6 alkynyl, C3-C7 cycloalkyl and aromatic atom group, in which the aromatic atom group is selected from phenyl, 2- or 3-thienyl, 2- or 3-puridyl, 2- or 3-pyrrolyl; and the substituent of the aromatic atom group is selected from the group consisting of Cl, Br, F, trifluoromethyl, NH2, NO2 and C1-C4 straight or branched chain alkyl.

Abstract translation: 目的：提供具有肟部分的氮杂双环化合物及其制备方法，其可用于治疗由包括阿尔茨海默病在内的胆碱神经传递障碍引起的脑神经疾病。 构成：提供了具有由式（I）表示的肟部分的氮杂双环化合物及其药学上可接受的盐，其中n是1或2; m是0或1; 和R是至少一个选自氢，F，Cl，甲氧基，OH，NH 2，NO 2，3,4-二甲氧基，2,4-二甲氧基，氰基，C 1 -C 6烷基，1,2或3个 3个氟原子取代的C 1 -C 6烷基，4-甲氧基苄氧基，叔丁氧基羰基，C 2 -C 6烯基，1,2或3个氟原子取代的C 2 -C 6炔基，C 3 -C 7环烷基和芳族原子基团， 选自苯基，2-或3-噻吩基，2-或3-嘌呤基，2-或3-吡咯基; 并且芳族原子基团的取代基选自Cl，Br，F，三氟甲基，NH 2，NO 2和C 1 -C 4直链或支链烷基。

公开(公告)号：KR100451414B1

公开(公告)日：2004-10-06

申请号：KR1020010089275

申请日：2001-12-31

Applicant: 한국과학기술연구원

Inventor： 조용서 ,  김유승 ,  고훈영 ,  최경일 ,  강경호 ,  배애님

IPC: C07D209/36

Abstract: PURPOSE: Indol derivatives and a preparation process thereof are provided, thereby rapidly preparing indol derivatives under mild conditions in higher yield. CONSTITUTION: Indol derivatives are represented by the formula 6, wherein R is H, or halogen selected from Cl, F, Br and I; and Y is -Ts(tosyl), -Ms(mesyl) or -Ac(acetyl). A process for preparing the indol derivatives of the formula 6 comprises the steps of: reacting a compound of the formula 1 with a compound of the formula 2 in the presence of indium metal and acid to simultaneously perform allylation of aldehyde and reduction of nitro group, thereby preparing a compound of the formula 3; protecting amine group of the compound of the formula 3 to prepare a compound of the formula 4; oxidizing secondary alcohol of the compound of the formula 4 to prepare a compound of the formula 5; and cyclization of the compound of the formula 5 in the presence of organic base, wherein the oxidation of secondary alcohol uses pyridinium chlorochromate(PCC) or pyridinium dichromate(PDC) or Swern's oxidation or Dess-Martin periodinane oxidation; and the organic base is diisopropylethylamine, DBU (1,8-diazabicyclo£5.4.0|undec-7-ene), DBN (1,5-diazabicyclo£4.3.0|non-5-ene), triethylamine or pyridine.

Abstract translation: 目的：提供吲哚衍生物及其制备方法，由此在温和条件下以较高的产率快速制备吲哚衍生物。 构成：吲哚衍生物由式6表示，其中R是H或选自Cl，F，Br和I的卤素; Y是-Ts（甲苯磺酰基），-Ms（甲磺酰基）或-Ac（乙酰基）。 制备式6吲哚衍生物的方法包括以下步骤：使式1化合物与式2化合物在铟金属和酸存在下反应，同时进行醛的烯丙基化和硝基的还原， 由此制备式3的化合物; 保护式3化合物的胺基以制备式4化合物; 氧化式4化合物的仲醇以制备式5化合物; 在有机碱存在下环化式5化合物，其中仲醇的氧化使用氯铬酸吡啶鎓（PCC）或重铬酸吡啶鎓（PDC）或斯文氧化或戴斯 - 马丁氧化剂氧化; DBU（1,8-二氮杂双环〔5.4.0〕十一碳-7-烯），DBN（1,5-二氮杂双环〔4.3.0〕壬-5-烯），三乙胺或吡啶组成的有机碱。

公开(公告)号：KR100441404B1

公开(公告)日：2004-07-23

申请号：KR1020020004199

申请日：2002-01-24

Applicant: 한국과학기술연구원

Inventor： 고훈영 ,  최경일 ,  조용서 ,  배애님 ,  차주환 ,  공재양 ,  정대영

IPC: C07D453/02 ,  C07D471/08 ,  C07D261/06

Abstract: PURPOSE: An alkenyl azabicyclic compound and a preparation method thereof are provided, which can be useful for treatment of cerebral nervous diseases caused by choline neurotransmission disorders. CONSTITUTION: An alkenyl azabicyclic compound represented by the formula(I) and pharmaceutically acceptable salts thereof are provided, wherein n is 1 or 2; and R is selected from the group consisting of hydrogen, F, Cl, methoxy, OH, NH2, NO2, 3,4-dimethoxy, 2,4-dimethoxy, cyano, C1-C6 alkyl, 1, 2 or 3 fluorine substituted C1-C6 alkyl, 4-methoxybenzyloxy, t-butoxycarbonyl, C2-C6 alkenyl, 1, 2 or 3 fluorine substituted C2-C6 alkynyl and C3-C7 cyloalkyl. A method for preparing the alkenyl azabicyclic compound of the formula(I) comprises a compound of the formula(II) with a compound of the formula(III) or formula(IV), wherein R1, R2 and R3 are independently C1-C6 alkyl, aryl or arylalkyl.

Abstract translation: 目的：提供烯基氮杂双环化合物及其制备方法，其可用于治疗由胆碱神经传递紊乱引起的脑神经疾病。 构成：提供由式（I）表示的烯基氮杂双环化合物及其药学上可接受的盐，其中n是1或2; 并且R选自氢，F，Cl，甲氧基，OH，NH 2，NO 2，3,4-二甲氧基，2,4-二甲氧基，氰基，C 1 -C 6烷基，1,2或3个氟取代的C 1 -C 6烷基，4-甲氧基苄氧基，叔丁氧基羰基，C 2 -C 6烯基，1,2或3个氟取代的C 2 -C 6炔基和C 3 -C 7环烷基。 用于制备式（I）的烯基氮杂双环化合物的方法包括式（II）的化合物与式（III）或式（IV）的化合物，其中R 1，R 2和R 3独立地为C 1 -C 6烷基 ，芳基或芳基烷基。

公开(公告)号：KR1020040037686A

公开(公告)日：2004-05-07

申请号：KR1020020066268

申请日：2002-10-29

Applicant: 한국과학기술연구원

Inventor： 고훈영 ,  조용서 ,  배애님 ,  차주환 ,  김혜연 ,  이재석 ,  김학수 ,  김상희

IPC: C07D413/10

CPC classification number: C07D413/10 ,  C07D413/14 ,  C07D417/14

Abstract: PURPOSE: Methylidene piperidinyl oxazolidinone derivatives and a preparation method thereof are provided, which compounds have improved antimicrobial activity, so that they can be useful for treatment of infection of pathogenic bacteria having resistance to conventional antibiotics. CONSTITUTION: Methylidene piperidinyl oxazolidinone derivatives represented by the formula(1) or pharmaceutically acceptable salts thereof are provided, wherein X is oxygen or sulfur atom; R1 and R2 are independently hydrogen, cyano, alkyl, halogen, acetoxy, ethoxycarbonyl, hydroxy, hydroxyamino, methoxyimino, aminoethyl, or one or more hetero atom selected from oxygen, nitrogen and sulfur; and n is 1 or 2. The method for preparing the methylidene piperidinyl oxazolidinone derivatives of the formula(1) comprises reacting a compound of the formula(2) with a compound of the formula(3) in the presence of catalyst with or without organic solvent.

Abstract translation: 目的：提供亚甲基哌啶基恶唑烷酮衍生物及其制备方法，该化合物具有改善的抗微生物活性，因此它们可用于治疗对常规抗生素具有抗性的病原菌的感染。 构成：提供由式（1）表示的亚甲基哌啶恶唑烷酮衍生物或其药学上可接受的盐，其中X是氧或硫原子; R 1和R 2独立地是氢，氰基，烷基，卤素，乙酰氧基，乙氧基羰基，羟基，羟基氨基，甲氧基亚氨基，氨基乙基或一个或多个选自氧，氮和硫的杂原子; 并且n为1或2.制备式（1）的亚甲基哌啶基恶唑烷酮衍生物的方法包括使式（2）化合物与式（3）化合物在催化剂存在或不与有机物 溶剂。

公开(公告)号：KR1020030063854A

公开(公告)日：2003-07-31

申请号：KR1020020004200

申请日：2002-01-24

Applicant: 한국과학기술연구원

Inventor： 고훈영 ,  최경일 ,  조용서 ,  배애님 ,  차주환 ,  공재양 ,  정대영

IPC: C07D453/02 ,  C07D471/08 ,  C07D261/06

Abstract: PURPOSE: Azabicyclic compounds having an oxime moiety and a preparation method thereof are provided, which can be useful for treatment of cerebral nervous diseases caused by choline neurotransmission disorders including Alzheimer's disease. CONSTITUTION: An azabicyclic compounds having an oxime moiety represented by the formula(I) and pharmaceutically acceptable salts thereof are provided, wherein n is 1 or 2; m is 0 or 1; and R is at least one substituent selected from the group consisting of hydrogen, F, Cl, methoxy, OH, NH2, NO2, 3, 4-dimethoxy, 2, 4-dimethoxy, cyano, C1-C6 alkyl, 1, 2 or 3 fluorine atom substituted C1-C6 alkyl, 4-methoxybenzyloxy, t-butoxycarbonyl, C2-C6 alkenyl, 1, 2 or 3 fluorine atom substituted C2-C6 alkynyl, C3-C7 cycloalkyl and aromatic atom group, in which the aromatic atom group is selected from phenyl, 2- or 3-thienyl, 2- or 3-puridyl, 2- or 3-pyrrolyl; and the substituent of the aromatic atom group is selected from the group consisting of Cl, Br, F, trifluoromethyl, NH2, NO2 and C1-C4 straight or branched chain alkyl.

Abstract translation: 目的：提供具有肟部分的氮杂双环化合物及其制备方法，其可用于治疗由胆碱神经传递障碍（包括阿尔茨海默氏病）引起的脑神经疾病。 构成：提供具有由式（I）表示的肟部分及其药学上可接受的盐的氮杂双环化合物，其中n为1或2; m为0或1; R为至少一个选自氢，F，Cl，甲氧基，OH，NH2，NO2,3,4-二甲氧基，2,4-二甲氧基，氰基，C1-C6烷基，1,2或 3个氟原子取代的C1-C6烷基，4-甲氧基苄氧基，叔丁氧基羰基，C2-C6烯基，1,2或3个氟原子取代的C2-C6炔基，C3-C7环烷基和芳族原子基团，其中芳族原子团 选自苯基，2-或3-噻吩基，2-或3-取代基，2-或3-吡咯基; 芳基原子的取代基选自Cl，Br，F，三氟甲基，NH 2，NO 2和C 1 -C 4直链或支链烷基。

公开(公告)号：KR100355343B1

公开(公告)日：2002-10-12

申请号：KR1019990050823

申请日：1999-11-16

Applicant: 한국과학기술연구원

Inventor： 고훈영 ,  조용서 ,  최경일 ,  배애님 ,  강경호 ,  이희윤 ,  공재양 ,  정대영

IPC: C07D261/14

Abstract: 본발명은신규삼차아미노에틸이소옥사졸유도체및 그제조방법에관한것으로서, 상기이소옥사졸유도체는여러가지중추신경계장애와관련이있는도파민-1 수용체의길항제로서작용하며, 그구조는화학식 1과같다. [화학식 1] 그제조방법은아래의화학식 2의아민과화학식 3의토실레이트의치환반응을이용한것으로서, 그반응은반응식 1과같다. [화학식 2] [화학식 3] [반응식 1] 상기화학식 1, 2, 3 및반응식 1에서, R는페닐, 할로겐원자에의해치환된페닐, 트리플루오로메틸에의해치환된페닐, 페닐기의 2, 3 또는 4 위치에트리플루오로메틸에의해치환된페닐메틸, 디페닐메틸, 페닐기의 2, 3 또는 4 위치에할로겐원자에의해치환된디페닐메틸, 벤질, 3-히드로벤즈이미다졸-2-온이며; R내지 R는모두수소이며; R는니트로기, 페녹시기, 메톡시기, 트리플루오로메틸기및 할로겐기로구성되는군에서선택되는하나이상에의해치환된페닐, 페닐기에의해치환된비닐또는 O, S 및 N으로구성되는군에서선택되는한가지원자에의해치환된 5환또는 6환의불포화또는포화헤테로고리화합물이며; X는질소또는 C-H이다.

公开(公告)号：KR100349035B1

公开(公告)日：2002-08-17

申请号：KR1020000037558

申请日：2000-07-01

Applicant: 한국과학기술연구원

Inventor： 조용서 ,  김유승 ,  고훈영 ,  최경일 ,  강경호

IPC: C07C209/32

Abstract: 본 발명은 인듐 금속 및 산을 이용하여 알데히드(-CHO)의 알릴화 및 니트로기(-NO
2 )의 환원 반응을 동시에 행하는 방법에 관한 것이며, 보다 구체적으로는 화학식
1의 화합물을 인듐 금속 및 산의 존재하에 화학식 2의 화합물과 반응시켜 알데히드의 알릴화 반응과 니트로기(-NO
2 )의 아민기(-NH
2 )로의 환원 반응을 동시에 행하여 화학식 3의 화합물을 제조하는 방법에 관한 것이다(반응식 1).
화학식 1

화학식 2

화학식 3

반응식 1

상기 화학식 1 내지 3 및 반응식 1 중에서, R은 C
6 -C
10 방향족 고리를 말하며; R
1 -R
3 은 서로 독립적으로 수소, C
1 -C
6 알킬기, 페닐기 또는 C
1 -C
3 알콕시 카르보닐기를 말하며; k는 0 - 4이며, 각 치환체 Y는 할로겐, 할로겐에 의해 치환된 또는 비치환된 C
1 -C
3 알킬기, 또는 할로겐에 의해 치환된 또는 비치환된 C
1 -C
3 알콕시기이거나, 두 개의 Y가 조합하여 5원 또는 6원 고리 또는 헤테로고리를 형성할 수 있으며; m은 1 - 3이며, n은 1 - 3이며; X은 Cl, Br, I로 구성되는 군에서 선택되는 할로겐 원소를 말한다.
상기 제조방법은 종래의 방법에 비해 알데히드의 알릴화 반응과 니트로기의 환원 반응을 동시에 수행할 수 있으며, 반응 수율이 높고, 반응이 상온에서 짧은 시간내에 진행하고, 수용액 상에서 반응이 손쉽게 진행되므로 환경친화적인 산업공정이다는 장점이 있다.

公开(公告)号：KR100343948B1

公开(公告)日：2002-07-24

申请号：KR1019990050824

申请日：1999-11-16

Applicant: 한국과학기술연구원

Inventor： 고훈영 ,  조용서 ,  최경일 ,  배애님 ,  강경호 ,  이희윤

IPC: C07D403/02

Abstract: 본발명은화학식 1을갖는이소옥사졸피페라진계열의화합물또는그의허용되는염 및그 제조방법과관한것으로, 상기화합물은아래의화학식 1을갖고, 그제조방법은아래의화학식 2의화합물과화학식 3의화합물을 1,3-쌍극자고리화첨가반응시키는것으로구성된다. 본발명은또한상기제조방법을용액상조합합성에응용하여제조된라이브러리에관한것이다. [화학식 1] [화학식 2] [화학식 3] 상기화학식 1, 2 및 3에서 R은 C-C의방향족탄화수소, C-C의알킬기에의해치환된 C-C의방향족탄화수소, C-C의알콕시기에의해치환된 C-C의방향족탄화수소, 할로겐에의해치환된 C-C의방향족탄화수소또는 C-C의아릴알킬이며; R-R는서로독립적으로수소, 할로겐, 메틸또는에틸이며; R-R은서로독립적으로수소, 할로겐에의해치환된페녹시, -OC(O)R, -NRR,,또는이며, 상기식 중 Y는 O 또는 S이고, R은 C-C의알킬기이고, R및 R은서로독립적으로 C-C의알킬기이고, R은수소, C-C의알킬기또는페닐이고, R는서로독립적으로수소또는 C-C의알킬기이고, n는 1-2의정수이고, k는 n=1이면 5, n=2이면 6이고, m은 n=1이면 4, n=2이면 5이다.

公开(公告)号：KR100343947B1

公开(公告)日：2002-07-22

申请号：KR1019990041613

申请日：1999-09-28

Applicant: 한국과학기술연구원

Inventor： 고훈영 ,  조용서 ,  최경일 ,  배애님 ,  강경호 ,  이지은 ,  이희윤 ,  공재양 ,  정대영 ,  정선호

IPC: C07D413/06

Abstract: 본발명은화학식 1을갖는이소옥사졸피페라진계열의화합물또는그 염의제조방법및 상기방법에의해만들어진라이브러리에관한것으로, 상기방법은화학식 2의화합물과화학식 3의화합물을염기및 염소화제의존재하에 1,3-쌍극자고리화첨가반응시켜화학식 1 또는그 염의화합물을제조하는것으로구성된다. 그화학식 1, 2, 3과반응식 1은다음과같다. 상기화학식 1, 2, 3과반응식 1에서, R및 R는페닐, 벤질, 할로겐화페닐, C-C의알킬기로치환된페닐, C-C의알콕시기로치환된페닐, (트리플루오로)메틸페닐, 피리딜등의페닐유도체를말하며, R-R는수소이며, X는질소이며,는이중결합또는삼중결합을의미하며,는이중결합또는단일결합을의미한다.