KR20100042671A - 신규 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 t-형 칼슘 이온 채널의 활성에 의해 유발되는 질환의 예방 또는 치료용 조성물 - Google Patents
신규 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 t-형 칼슘 이온 채널의 활성에 의해 유발되는 질환의 예방 또는 치료용 조성물 Download PDFInfo
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- 0 CC(C)C(CCCBr)(C(O*)=O)c1ccccc1 Chemical compound CC(C)C(CCCBr)(C(O*)=O)c1ccccc1 0.000 description 1
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Abstract
Description
구분 | % 억제율(10 μM) | IC50(μM) |
실시예 1 | 96.9±0.59 | 8.17±0.48(nM) |
실시예 4 | 93.5±3.2 | 0.19±0.001 |
실시예 5 | 91.7±1.9 | 0.88±0.07 |
실시예 10 | 98.3±0.9 | 0.25±0.005 |
실시예 11 | 91.4±0.4 | 0.10±0.01 |
실시예 12 | 94.2±0.4 | 53.02±4.87(nM) |
실시예 13 | 94.5±1.2 | 0.25±0.01 |
실시예 23 | 96.3±1.7 | 0.34±0.02 |
실시예 26 | 94.0±2.5 | 0.26±0.03 |
실시예 31 | 90.4±3.2 | 0.74±0.02 |
실시예 32 | 89.3±1.6 | 0.98±0.11 |
실시예 33 | 96.5±1.7 | 1.11±0.05 |
실시예 35 | 93.0±1.5 | 0.28±0.02 |
실시예 36 | 94.1±1.5 | 95.04±14.78(nM) |
실시예 39 | 96.0±1.7 | 0.48±0.08 |
실시예 40 | 95.1±1.9 | 0.32±0.01 |
실시예 41 | 94.9±1.5 | 0.39±0.03 |
비교군(미베프라딜) | 95.9±1.7 | 1.34±0.49 |
Claims (13)
- 하기 화학식 1로 표시되는 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염:[화학식 1](상기 화학식 1에서X는 수소, 할로겐 또는 C1 ~4 알콕시이고,R1은 C1 ~4 직쇄 또는 측쇄 알킬이고,이때, R3 및 R4는 독립적으로 또는 선택적으로 H, C1 ~4 직쇄 또는 측쇄 알킬, 또는 C1 ~4 알콕시이고,Y는 C 또는 N이며,R5는 비치환 또는 1 이상의 할로겐, C1 ~4 직쇄 또는 측쇄 알킬, 또는 C1 ~4 알 콕시로 치환된 페닐; 비치환 또는 1 이상의 할로겐, C1 ~4 직쇄 또는 측쇄 알킬, 또는 C1 ~4 알콕시로 치환된 벤질; 또는 비치환 또는 1 이상의 할로겐, C1 ~4 직쇄 또는 측쇄 알킬, 또는 C1 ~4 알콕시로 치환된 벤질리덴이다.)
- 제1항에 있어서, 상기 X는 수소, 염소, 브롬, 메톡시 또는 에톡시이고,R1은 메틸, 에틸, 프로필, 이소프로필이고,이때, R3 및 R4는 독립적으로 또는 선택적으로 H, 메틸, 에틸, 메톡시 또는 에톡시이고,Y는 C 또는 N이며,R5는 비치환 또는 1 이상의 플루오린, 염소, 브롬, 메틸, 에틸, 메톡시 또는 에톡시로 치환된 페닐; 비치환 또는 1 이상의 플루오린, 염소, 브롬, 메틸, 에틸, 메톡시 또는 에톡시로 치환된 벤질; 또는 비치환 또는 1 이상의 플루오린, 염소, 브롬, 메틸, 에틸, 메톡시 또는 에톡시로 치환된 벤질리덴인 것을 특징으로 하는 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염.
- 제1항에 있어서, 상기 X는 수소, 브롬 또는 메톡시이고,R1은 메틸 또는 에틸이고,이때, R3 및 R4는 독립적으로 또는 선택적으로 H, 메틸 또는 메톡시이고,Y는 C 또는 N이며,R5는 페닐, 디페닐, 플루오로페닐, 클로로페닐, 메톡시페닐, 플루오로벤질, 트리플루오로벤질, 클로로벤질, 디클로로벤질, 2-클로로-6-플루오로벤질, 메틸벤질, t-부틸벤질, 메톡시벤질, 트리메톡시벤질, 플루오로벤질리덴, 클로로벤질리덴, 메틸벤질리덴 또는 메톡시벤질리덴인 것을 특징으로 하는 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염.
- 제1항에 있어서, 상기 페닐아세테이트 유도체는(1) 5-{[3-(1H-벤즈이미다졸-2-일)프로필]메틸아미노}-2-(4-브로모페닐)-2-이소프로필펜탄산 메틸 에스테르;(2) 2-(4-브로모페닐)-2-이소프로필-5-(4-페닐피페라진-1-일)펜탄산 메틸 에스테르;(3) 2-(4-브로모페닐)-2-이소프로필-5-[4-(4-메톡시벤질리덴)피페리딘-1-일]펜탄산 메틸 에스테르;(4) 메틸 5-((3-(1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-이소프로필-2-(4-메톡시페닐)펜타노에이트;(5) 메틸 2-이소프로필-5-((3-(5-메톡시-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-(4-메톡시페닐)펜타노에이트;(6) 메틸 5-((3-(5,6-디메틸-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-이소프로필-2-(4-메톡시페닐)펜타노에이트;(7) 메틸 5-((3-(1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-(3,4-디메톡시페닐)-2-이소프로필펜타노에이트;(8) 메틸 2-(3,4-디메톡시페닐)-2-이소프로필-5-((3-(5-메톡시-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)펜타노에이트;(9) 메틸 2-(3,4-디메톡시페닐)-5-((3-(5,6-디메틸-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-이소프로필펜타노에이트;(10) 에틸 5-((3-(1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-이소프로필-2-페닐펜타노에이트;(11) 에틸 5-((3-(5,6-디메틸-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-이소프로필-2-페닐펜타노에이트;(12) 메틸 2-(4-브로모페닐)-5-((3-(5,6-디메틸-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-이소프로필펜타노에이트;(13) 메틸 2-(4-브로모페닐)-2-이소프로필-5-((3-(5-메톡시-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)펜타노에이트;(14) 메틸 5-((3-(1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-(3-브로모페닐)-2-이소프로필펜타노에이트;(15) 메틸 2-(3-브로모페닐)-2-이소프로필-5-((3-(5-메톡시-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)펜타노에이트;(16) 메틸 2-(3-브로모페닐)-5-((3-(5,6-디메틸-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-이소프로필펜타노에이트;(17) 메틸 5-((3-(1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(18) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-((3-(5-메톡시-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)펜타노에이트;(19) 메틸 5-((3-(5,6-디메틸-1H-벤조[d]이미다졸-2-일)프로필)(메틸))아미노)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(20) 에틸 2-이소프로필-5-(4-(2-메톡시페닐)피페라진-1-일)-2-페닐펜타노에이트;(21) 에틸 2-이소프로필-5-(4-(3-메톡시페닐)피페라진-1-일)-2-페닐펜타노에이트;(22) 에틸 2-이소프로필-5-(4-(4-메톡시페닐)피페라진-1-일)-2-페닐펜타노에이트;(23) 에틸 2-이소프로필-5-(4-(4-메톡시벤질)피페라진-1-일)-2-페닐펜타노에이트;(24) 에틸 5-(4-(2-플루오로페닐)피페라진-1-일)-2-이소프로필-2-페닐펜타노에이트;(25) 에틸 5-(4-(4-플루오로페닐)피페라진-1-일)-2-이소프로필-2-페닐펜타노에이트;(26) 에틸 5-(4-(4-플루오로벤질)피페라진-1-일)-2-이소프로필-2-페닐펜타노에이트;(27) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-페닐피페라진-1-일)펜타노에이트;(28) 메틸 5-(4-벤즈하이드릴피페라진-1-일)-2-(4-브로모페닐)-2-이소프로필펜타노에이트;(29) 메틸 2-(4-브로모페닐)-5-(4-(2-플루오로페닐)피페라진-1-일)-2-이소프로필펜타노에이트;(30) 메틸 2-(4-브로모페닐)-5-(4-(4-플루오로페닐)피페라진-1-일)-2-이소프로필펜타노에이트;(31) 메틸 2-(4-브로모페닐)-5-(4-(2-플루오로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(32) 메틸 2-(4-브로모페닐)-5-(4-(3-플루오로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(33) 메틸 2-(4-브로모페닐)-5-(4-(4-플루오로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(34) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(3-(트리플루오로메틸)벤질)피페라진-1-일)펜타노에이트;(35) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(4-(트리플루오로메틸)벤질)피페라진-1-일)펜타노에이트;(36) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(2-메톡시페닐)피페라진-1-일)펜타노에이트;(37) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(3-메톡시페닐)피페라진-1-일)펜타노에이트;(38) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(4-메톡시페닐)피페라진-1-일)펜타노에이트;(39) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(4-메톡시벤질)피페라진-1-일)펜타노에이트;(40) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(2,3,4-트리메톡시벤질)피페라진-1-일)펜타노에이트;(41) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(3-메틸벤질)피페라진-1-일)펜타노에이트;(42) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(4-메틸벤질)피페라진-1-일)펜타노에이트;(43) 메틸 2-(4-브로모페닐)-5-(4-(4-t-부틸벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(44) 메틸 2-(4-브로모페닐)-5-(4-(3-클로로페닐)피페라진-1-일)-2-이소프로필펜타노에이트;(45) 메틸 2-(4-브로모페닐)-5-(4-(3-클로로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(46) 메틸 2-(4-브로모페닐)-5-(4-(4-클로로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(47) 메틸 2-(4-브로모페닐)-5-(4-(3,4-디클로로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(48) 메틸 2-(4-브로모페닐)-5-(4-(2-클로로-6-플루오로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(49) 메틸 2-(3-브로모페닐)-5-(4-(2-플루오로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(50) 메틸 2-(3-브로모페닐)-5-(4-(3-플루오로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(51) 메틸 2-(3-브로모페닐)-5-(4-(4-플루오로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(52) 메틸 2-(3-브로모페닐)-2-이소프로필-5-(4-(3-(트리플루오로메틸)벤질)피페라진-1-일)펜타노에이트;(53) 메틸 2-(3-브로모페닐)-2-이소프로필-5-(4-(4-(트리플루오로메틸)벤질)피페라진-1-일)펜타노에이트;(54) 메틸 2-(3-브로모페닐)-2-이소프로필-5-(4-(4-메톡시벤질)피페라진-1-일)펜타노에이트;(55) 메틸 2-(3-브로모페닐)-2-이소프로필-5-(4-(3,4,5-트리메톡시벤질)피페라진-1-일)펜타노에이트;(56) 메틸 2-(3-브로모페닐)-2-이소프로필-5-(4-(3-메틸벤질)피페라진-1-일)펜타노에이트;(57) 메틸 2-(3-브로모페닐)-2-이소프로필-5-(4-(4-메틸벤질)피페라진-1-일)펜타노에이트;(58) 메틸 2-(3-브로모페닐)-5-(4-(4-t-부틸벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(59) 메틸 2-(3-브로모페닐)-5-(4-(3-클로로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(60) 메틸 2-(3-브로모페닐)-5-(4-(4-클로로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(61) 메틸 2-(3-브로모페닐)-5-(4-(3,4-디클로로벤질)피페라진-1-일)-2-이소프로필펜타노에이트;(62) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-페닐피페라진-1-일)펜타노에이트;(63) 메틸 5-(4-벤즈하이드릴피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(64) 메틸 2-(4-플루오로페닐)-5-(4-(2-플루오로페닐)피페라진-1-일)-2-이소프로필펜타노에이트;(65) 메틸 2-(4-플루오로페닐)-5-(4-(4-플루오로페닐)피페라진-1-일)-2-이소프로필펜타노에이트;(66) 메틸 5-(4-(2-플루오로벤질)피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(67) 메틸 5-(4-(3-플루오로벤질)피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(68) 메틸 5-(4-(4-플루오로벤질)피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(69) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(3-(트리플루오로메틸)벤질)피페라진-1-일)펜타노에이트;(70) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(4-(트리플루오로메틸)벤질)피페라진-1-일)펜타노에이트;(71) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(2-메톡시페닐)피페라진-1-일)펜타노에이트;(72) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(3-메톡시페닐)피페라진-1-일)펜타노에이트;(73) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(4-메톡시페닐)피페라진-1-일)펜타노에이트;(74) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(4-메톡시벤질)피페라진-1-일)펜타노에이트;(75) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(2,3,4-트리메톡시벤질)피페라진-1-일)펜타노에이트;(76) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(3-메틸벤질)피페라진-1-일)펜타노에이트;(77) 메틸 2-(4-플루오로페닐)-2-이소프로필-5-(4-(4-메틸벤질)피페라진-1-일)펜타노에이트;(78) 메틸 5-(4-(4-t-부틸벤질)피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(79) 메틸 5-(4-(3-클로로페닐)피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(80) 메틸 5-(4-(3-클로로벤질)피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(81) 메틸 5-(4-(4-클로로벤질)피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(82) 메틸 5-(4-(3,4-디클로로벤질)피페라진-1-일)-2-(4-플루오로페닐)-2-이소프로필펜타노에이트;(83) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(4-메톡시벤질리덴)피페리딘-1-일)펜타노에이트;(84) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(4-메톡시벤질)피페리딘-1-일)펜타노에이트;(85) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(3-메톡시벤질리덴)피페리딘-1-일)펜타노에이트;(86) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(3-메톡시벤질)피페리딘-1-일)펜타노에이트;(87) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(4-메틸벤질리덴)피페리딘-1-일)펜타노에이트;(88) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(4-메틸벤질)피페리딘-1-일)펜타노에이트;(89) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(3-메틸벤질리덴)피페리딘-1-일)펜타노에이트;(90) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(3-메틸벤질)피페리딘-1-일)펜타노에이트;(91) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(2-메틸벤질리덴)피페리딘-1-일)펜타노에이트;(92) 메틸 2-(4-브로모페닐)-2-이소프로필-5-(4-(2-메틸벤질)피페리딘-1-일)펜타노에이트;(93) 메틸 2-(4-브로모페닐)-5-(4-(4-클로로벤질리덴)피페리딘-1-일)-2-이소프로필펜타노에이트;(94) 메틸 2-(4-브로모페닐)-5-(4-(4-클로로벤질)피페리딘-1-일)-2-이소프로필펜타노에이트;(95) 메틸 2-(4-브로모페닐)-5-(4-(3-클로로벤질리덴)피페리딘-1-일)-2-이소프로필펜타노에이트;(96) 메틸 2-(4-브로모페닐)-5-(4-(3-클로로벤질)피페리딘-1-일)-2-이소프로필펜타노에이트;(97) 메틸 2-(4-브로모페닐)-5-(4-(4-플루오로벤질리덴)피페리딘-1-일)-2-이소프로필펜타노에이트;(98) 메틸 2-(4-브로모페닐)-5-(4-(4-플루오로벤질)피페리딘-1-일)-2-이소프로필펜타노에이트;(99) 메틸 2-이소프로필-5-(4-(4-메톡시벤질리덴)피페리딘-1-일)-2-(4-메톡시페닐)펜타노에이트;(100) 메틸 2-이소프로필-5-(4-(4-메톡시벤질)피페리딘-1-일)-2-(4-메톡시페닐)펜타노에이트;(101) 메틸 2-이소프로필-5-(4-(3-메톡시벤질리덴)피페리딘-1-일)-2-(4-메톡시페닐)펜타노에이트;(102) 메틸 2-이소프로필-5-(4-(3-메톡시벤질)피페리딘-1-일)-2-(4-메톡시페닐)펜타노에이트;(103) 메틸 2-이소프로필-2-(4-메톡시페닐)-5-(4-(4-메틸벤질리덴)피페리딘-1-일)펜타노에이트;(104) 메틸 2-이소프로필-2-(4-메톡시페닐)-5-(4-(4-메틸벤질)피페리딘-1-일)펜타노에이트;(105) 메틸 2-이소프로필-2-(4-메톡시페닐)-5-(4-(3-메틸벤질리덴)피페리딘-1-일)펜타노에이트;(106) 메틸 2-이소프로필-2-(4-메톡시페닐)-5-(4-(3-메틸벤질)피페리딘-1-일)펜타노에이트;(107) 메틸 2-이소프로필-2-(4-메톡시페닐)-5-(4-(2-메틸벤질리덴)피페리딘-1-일)펜타노에이트;(108) 메틸 2-이소프로필-2-(4-메톡시페닐)-5-(4-(2-메틸벤질)피페리딘-1-일)펜타노에이트;(109) 메틸 5-(4-(4-클로로벤질리덴)피페리딘-1-일)-2-이소프로필-2-(4-메톡시페닐)펜타노에이트;(110) 메틸 5-(4-(4-클로로벤질)피페리딘-1-일)-2-이소프로필-2-(4-메톡시페닐)펜타노에이트;(111) 메틸 5-(4-(3-클로로벤질리덴)피페리딘-1-일)-2-이소프로필-2-(4-메톡시페닐)펜타노에이트;(112) 메틸 5-(4-(3-클로로벤질)피페리딘-1-일)-2-이소프로필-2-(4-메톡시페닐)펜타노에이트;(113) 메틸 5-(4-(4-플루오로벤질리덴)피페리딘-1-일)-2-이소프로필-2-(4-메톡시페닐)펜타노에이트; 및(114) 메틸 5-(4-(4-플루오로벤질)피페리딘-1-일)-2-이소프로필-2-(4-메톡시페닐)펜타노에이트로 이루어지는 군으로부터 선택되는 것을 특징으로 하는 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염.
- 하기 반응식 1에 표시되는 바와 같이,출발물질인 화학식 2의 카르복시산 화합물을 산촉매 하에서 에스테르화 반응시켜 화학식 3의 에스테르 화합물을 제조하는 단계(단계 1);상기 단계 1에서 제조된 화학식 3의 화합물을 t-부톡사이드 및 이소프로필 브로마이드와 반응시켜 화학식 4의 화합물을 제조하는 단계(단계 2);상기 단계 2에서 제조된 화학식 4의 화합물을 1,3-디브로모프로판과 반응시켜 화학식 5의 화합물을 제조하는 단계(단계 3); 및상기 단계 3에서 제조된 화학식 5의 화합물을 화학식 6 또는 화학식 7의 화합물과 반응시켜 화학식 1의 화합물을 제조하는 단계(단계 4)를 포함하는 페닐아세테이트 유도체의 제조방법:[반응식 1](상기 식에서, R1, R2, R3, R4, R5, X 및 Y는 상기 화학식 1에서 정의한 바와 같다.)
- 제5항에 있어서, 상기 단계 1은 화학식 2의 카르복시산 화합물을 메탄올에 용해시킨 후, 85~95 ℃에서 황산의 존재 하에 2~4시간 동안 가열 환류시켜 화학식 3의 화합물을 수득하는 것을 특징으로 하는 페닐아세테이트 유도체의 제조방법.
- 제5항에 있어서, 상기 단계 2는 화학식 3의 화합물과 t-부톡사이드를 0 ℃에서 반응용매인 무수 디메틸포름아미드에 용해시킨 후, 이소프로필 브로마이드를 첨가하여 상온에서 2~4시간 동안 교반하여 화학식 4의 화합물을 수득하는 것을 특징으로 하는 페닐아세테이트 유도체의 제조방법.
- 제5항에 있어서, 상기 단계 3은 -75 ~ -80 ℃에서 무수 테트라히드로퓨란에 디이소프로필아민과 헥산에 n-부틸리튬을 용해시킨 용액을 차례대로 첨가하여 용해시킨 후, 화학식 4의 화합물을 넣고 교반시킨 다음, 1,3-디브로모프로판을 무수 테트라히드로퓨란에 넣은 용액에 적가하여 상온에서 밤새 교반시킴으로써 화학식 5의 화합물을 수득하는 것을 특징으로 하는 페닐아세테이트 유도체의 제조방법.
- 제5항에 있어서, 상기 단계 4에서 화학식 5의 화합물을 화학식 6의 화합물과 반응시키는 경우, 화학식 5를 메탄올에 용해시킨 후, 화학식 6의 화합물과 탄산칼륨을 첨가하여 85~95 ℃에서 2~4시간 동안 가열 환류시킴으로써 화학식 1의 화합물을 수득하는 것을 특징으로 하는 페닐아세테이트 유도체의 제조방법.
- 제5항에 있어서, 상기 단계 4에서 화학식 5의 화합물을 화학식 7의 화합물과 반응시키는 경우, 화학식 5를 아세토니트릴에 용해시킨 후, 화학식 7의 화합물과 트리에틸아민, 요오드산나트륨을 차례대로 첨가하여 85~95 ℃에서 2~4시간 동안 가열 환류시킴으로써 화학식 1의 화합물을 수득하는 것을 특징으로 하는 페닐아세테이트 유도체의 제조방법.
- 제1항의 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 T-형 칼슘 이온 채널의 활성에 의해 유발되는 질환의 예방 또는 치료용 조성물
- 제12항에 있어서, 상기 T-형 칼슘 이온 채널의 활성에 의해 유발되는 질환은 고혈압, 암, 간질 또는 신경성 통증인 것을 특징으로 하는 조성물.
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KR1020080084563A KR101052620B1 (ko) | 2008-08-28 | 2008-08-28 | 신규 페닐아세테이트 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 t-형 칼슘 이온 채널의 활성에 의해 유발되는 질환의 예방 또는 치료용 조성물 |
JP2008316342A JP4950170B2 (ja) | 2008-08-28 | 2008-12-12 | 新規フェニルアセテート誘導体またはその薬学的に許容可能な塩、その製造方法及びそれを有効成分として含むt−型カルシウムイオンチャンネルの活性によって誘発される疾患の予防または治療用組成物 |
US12/429,004 US7939672B2 (en) | 2008-08-28 | 2009-04-23 | Phenylacetate derivatives or pharmaceutically acceptable salts thereof, preparation method thereof and composition for prevention or treatment of diseases induced by activation of T-type calcium ion channel containing the same as an active ingredient |
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US9096531B2 (en) | 2010-05-24 | 2015-08-04 | Toa Eiyo Ltd. | Fused imidazole derivative |
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US11130750B2 (en) | 2017-02-15 | 2021-09-28 | Cavion, Inc. | Calcium channel inhibitors |
MX2019012818A (es) | 2017-04-26 | 2020-07-14 | Cavion Inc | Metodos para mejorar la memoria y la cognicion y para el tratamiento de trastornos de la memoria y cognitivos. |
CN113164393A (zh) | 2018-10-03 | 2021-07-23 | 卡维昂公司 | 使用(r)-2-(4-异丙基苯基)-n-(1-(5-(2,2,2-三氟乙氧基)吡啶-2-基)乙基)乙酰胺治疗原发性震颤 |
CN114340670A (zh) | 2019-07-11 | 2022-04-12 | 普拉克西斯精密药物股份有限公司 | T-型钙通道调节剂的制剂及其使用方法 |
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DE2861000D1 (en) * | 1977-07-20 | 1981-11-26 | Ciba Geigy Ag | Phenyl acetates of 2-oxypyridyl, process for their preparation and their use as pesticides |
JPS5639049A (en) | 1979-09-07 | 1981-04-14 | Nippon Soda Co Ltd | Phenyl acetate, its preparation, insecticide, and acaricide |
JPS60110887A (ja) * | 1983-11-18 | 1985-06-17 | Shiyouno Tamie | α−アルキル化酢酸誘導体の製造方法 |
JPS60146872A (ja) * | 1984-01-06 | 1985-08-02 | Tooa Eiyoo Kk | フエニルピペリジン誘導体及びその製造法 |
JPS6127964A (ja) * | 1984-07-16 | 1986-02-07 | Tooa Eiyoo Kk | 新規フエニルピペリジン誘導体 |
JPS61271250A (ja) * | 1985-05-28 | 1986-12-01 | Nippon Kayaku Co Ltd | 置換トロパ酸類の製造方法 |
JP2822492B2 (ja) * | 1989-10-11 | 1998-11-11 | 住友化学工業株式会社 | α―イソプロピル―4―クロルフェニル酢酸エステルの製造法 |
AU7409300A (en) * | 1999-08-20 | 2001-03-19 | Boehringer Ingelheim Pharma Kg | Substituted piperazine derivatives, the production thereof and their utilization as medicaments |
JP2004532799A (ja) * | 2000-10-11 | 2004-10-28 | エスペリオン セラピューティクス,インコーポレイテッド | コレステロール管理および関連用途のためのスルフィド化合物およびジスルフィド化合物ならびにそれらを含む組成物 |
US20050020694A1 (en) * | 2001-10-11 | 2005-01-27 | Dasseux Jean-Louis Henri | Sulfide and disulfide compounds and compositions for cholesterol management and related uses |
AU2003300439A1 (en) * | 2003-12-24 | 2005-08-03 | Esperion Therapeutics, Inc. | Sulfide and disulfide compounds and compositions for cholesterol management and related uses |
KR100743255B1 (ko) | 2006-05-04 | 2007-07-27 | 한국과학기술연구원 | T-형 칼슘 채널에 활성을 지닌 신규1,3-다이옥소아이소인돌 유도체 |
KR100754325B1 (ko) | 2006-06-12 | 2007-09-05 | 한국과학기술연구원 | T-형 칼슘 채널 길항제로서의3-(4-클로로벤질)-4-옥소-2-티옥소-1,2,3,4-테트라히드로-퀴나졸린 유도체 |
KR100784195B1 (ko) | 2007-01-05 | 2007-12-11 | 경희대학교 산학협력단 | 3,4-디히드로퀴나졸린 유도체를 포함하는 항암제 조성물 |
US20100190852A1 (en) * | 2007-06-20 | 2010-07-29 | Milestone Pharmaceuticals Inc. | Short acting phenylalkylamine calcium channel blockers and uses thereof |
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