KR20020075926A - 2-옥소-1-피롤리딘 유도체, 이의 제조 방법 및 용도 - Google Patents
2-옥소-1-피롤리딘 유도체, 이의 제조 방법 및 용도 Download PDFInfo
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- KR20020075926A KR20020075926A KR1020027010960A KR20027010960A KR20020075926A KR 20020075926 A KR20020075926 A KR 20020075926A KR 1020027010960 A KR1020027010960 A KR 1020027010960A KR 20027010960 A KR20027010960 A KR 20027010960A KR 20020075926 A KR20020075926 A KR 20020075926A
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Abstract
Description
Claims (39)
- 하기 화학식 Ⅰ의 화합물 또는 이것의 약제학적으로 허용되는 염:상기 식에서,X는 -CA1NR5R6, -CA1OR7, -CA1-R8또는 CN이며;A1및 A2는 독립적으로 산소, 황 또는 -NR9이며;R1은 수소, 알킬, 아릴 또는 -CH2-R1a(여기서, R1a는 아릴, 헤테로사이클, 할로겐, 히드록시, 아미노, 니트로 또는 시아노임)이며;R2, R3및 R4는 동일하거나 상이하며, 이들 각각은 독립적으로 수소, 할로겐, 히드록시, 티올, 아미노, 니트로, 니트로옥시, 시아노, 아지도, 카르복시, 아미도, 술폰산, 술폰아미드, 알킬, 알케닐, 알키닐, 에스테르, 에테르, 아릴, 헤테로사이클 또는 옥시 유도체, 티오 유도체, 아미노 유도체, 아실 유도체, 술포닐 유도체 또는 술피닐 유도체이며;R2a, R3a및 R4a는 동일하거나 상이하며, 각각 독립적으로 수소, 할로겐, 알킬, 알케닐, 알키닐 또는 아릴이며;R5, R6, R7및 R9는 동일하거나 상이하며, 각각 독립적으로 수소, 히드록시, 알킬, 아릴, 헤테로사이클 또는 옥시 유도체이고;R8은 수소, 히드록시, 티올, 할로겐, 알킬, 아릴, 헤테로사이클 또는 티오 유도체이며;단, R2, R3, R4, R2a, R3a및 R4a중 하나 이상은 수소 이외의 기이며,화합물이 모든 가능한 이성질체의 혼합물이며, X가 -CONR5R6이며, A2가 산소이고, R1이 수소, 메틸, 에틸 또는 프로필인 경우, 피롤리딘 고리상의 치환기는 모노-, 디- 또는 트리-메틸, 또는 모노-에틸 이외의 기이고;R1, R2, R4, R2a, R3a및 R4a가 각각 수소이며, A2는 산소이고, X가 -CONR5R6인 경우, R3은 카르복시, 에스테르, 아미도, 치환된 옥소-피롤리딘, 히드록시, 옥시 유도체, 아미노, 아미노 유도체, 메틸, 나프틸, 할로겐 원자에 의해 파라 위치에서 또는 옥시 유도체에 의해 선택적으로 치환된 페닐기와 상이하다.
- 제 1 항에 있어서, X가a) -COOR7또는 -CONR5R6;b) -COOR7또는 -CONR5R6(여기서, R5, R6및 R7은 수소, C1-4-알킬, 페닐 또는 알킬페닐임);c) 카르복시 또는 -CONR5R6;d) 카르복시 또는 -CONR5R6(여기서, R5및 R6은 바람직하게는, 수소, C1-4-알킬, 페닐 또는 알킬페닐임);e) -CONR5R6; 또는f) -CONH2로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 1 항에 있어서, R1이a) 수소, 알킬 또는 아릴;b) 수소, C1-12 알킬 또는 아릴;c) 수소, 저급 알킬 또는 페닐;d) 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소- 또는 3차-부틸, 2,2,2-트리메틸에틸(이들 각각은 메틸렌 가교(methylene bridge)를 통해 선택적으로 결합됨), 또는 이들의 하나 이상의 할로겐 원자에 의해 치환된 것들; 또는e) 에틸로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 1 항에있어서, R2및 R2a가 독립적으로a) 수소, 할로겐 또는 알킬;b) 수소, 할로겐 또는 저급 알킬;c) 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소 또는 3차-부틸, 2,2,2-트리메틸에틸 또는 이들의 하나 이상의 할로겐 원자에 의해 치환된 것들, 수소 또는 할로겐으로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 4 항에 있어서, R2및 R2a중 하나 이상이 수소이거나, 둘 모두가 수소임을 특징으로 하는 화합물.
- 제 1 항에 있어서, R3a, R4및 R4a가 독립적으로a) 수소, 알킬, 아릴 또는 아랄킬;b) 수소, 메틸, 에틸, 페닐 또는 벤질;c) 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소 또는 3차-부틸, 2,2,2-트리메틸에틸 또는 이들의 하나 이상의 할로겐 원자에 의해 치환된 것들, 수소 또는 할로겐으로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 6 항에 있어서, R4및 R4a중 하나 이상이 수소이거나, 둘 모두가 수소임을특징으로 하는 화합물.
- 제 6 항 또는 제 7 항에 있어서, R3a가a) 수소 또는 알킬;b) 수소 또는 저급 알킬; 또는c) 수소로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 1 항에 있어서, R3이a) 수소, C1-12-알킬(이들 각각은 히드록시, 할로겐, 시아노, 티오시아나토 또는 알콕시로부터 선택된 하나 이상의 치환기에 의해 선택적으로 치환되고, 고리에 직접적으로, 또는 티오, 술피닐, 술포닐, 카르보닐 또는 옥시카르보닐기 및 선택적으로 C1-4-알킬렌 가교를 통해 결합됨); C2-6-알케닐 또는 -알키닐(이들 각각은 선택적으로 하나 이상의 할로겐에 의해 치환됨); 아지도; 시아노; 아미도; 카르복시; 트리아졸릴, 테트라졸릴, 피롤리디닐, 피리딜, 1-옥시도피리딜, 티오몰폴리닐, 벤조디옥솔릴, 푸릴, 옥사졸릴, 피리미디닐, 피롤릴, 티아디아졸릴, 티아졸릴, 티에닐 또는 피페라지닐(이들 각각은 할로겐, C1-6-알킬 및 페닐로부터 선택된 하나 이상의 치환기에 의해 선택적으로 치환되고, 직접적으로 또는 카르보닐기 또는 C1-4-알킬렌 가교를 통해 고리에 결합됨); 나프틸; 또는 페닐, 페닐알킬 또는 페닐알케닐(이들 각각은 할로겐, C1-6-알킬, C1-6 할로알킬, C1-6-알콕시, C1-6 알킬티오, 아미노, 아지도, 페닐 및 니트로로부터 선택된 하나 이상의 치환기에 의해 선택적으로 치환되고, 직접적으로, 또는 옥시, 술포닐, 술포닐옥시, 카르보닐 또는 카르보닐옥시기 및 선택적으로 C1-4-알킬렌 가교를 통해 고리에 결합됨);b) 알킬이 C1-6-알킬이고, C1-4 알킬렌 가교가 메틸렌이라는 것을 제외하고는 a)와 동일;c) 할로겐, 티오시아나토, 아지도, 알콕시, 알킬티오, 페닐술포닐로부터 선택된 하나 이상의 치환기에 의해 선택적으로 치환된 C1-6-알킬; 니트로옥시; C2-3-알케닐 또는 -알키닐; 테트라졸릴, 피리딜, 푸릴, 피롤릴, 티아졸릴 또는 티에닐(이들 각각은 선택적으로 하나 이상의 할로겐 또는 아세틸에 의해 치환됨); 또는 페닐 또는 페닐알킬(이들 각각은 선택적으로 할로겐, C1-6-알킬, C1-6 할로알킬, C1-6-알콕시, 아미노, 아지도, 페닐 및 니트로로부터 선택된 하나 이상의 치환기에 의해 치환되고, 직접적으로, 또는 술포닐옥시 및 선택적으로, C1-4-알킬렌 가교, 특히 메틸렌을 통해 고리에 결합됨);d) C1-4 알킬렌 가교가 메틸렌이라는 것을 제외하고는 c)와 동일;e) 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소 또는 3차-부틸, 2,2,2-트리메틸에틸 또는 이들의 하나 이상의 할로겐 원자에 의해 치환된 것들, 수소, 또는 할로겐;f) 할로겐, 티오시아나토 또는 아지도로부터 선택된 하나 이상의 치환기에 의해 선택적으로 치환된 C1-4-알킬; C2-5-알케닐 또는 -알키닐(이들 각각은 선택적으로 하나 이상의 할로겐에 의해 치환됨); 티에닐; 또는 할로겐, C1-6-알킬, C1-6할로알킬 또는 아지도로부터 선택된 하나 이상의 치환기에 의해 선택적으로 치환된 페닐); 또는g) C1-6-알킬 및 C2-6-할로알케닐로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 1 항에 있어서, R5및 R6이 독립적으로,a) 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소 또는 3차-부틸, 2,2,2-트리메틸에틸; 또는b) 수소 또는 메틸로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 10 항에 있어서, R5및 R6중 하나 이상이 수소이거나, 둘 모두가 수소임을 특징으로 하는 화합물.
- 제 1 항에 있어서, R7이a) 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소 또는 3차-부틸, 2,2,2-트리메틸에틸, 페닐, 벤질, 또는 이들의 하나 이상의 할로겐 원자에 의해 치환된 것들;b) 수소, 메틸 또는 에틸; 또는c)수소로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 1 항에 있어서, R8이a) 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소 또는 3차-부틸, 2,2,2-트리메틸에틸, 페닐, 벤질, 또는 이들의 하나 이상의 할로겐 원자에 의해 치환된 것들; 또는b) 수소 또는 메틸로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 1 항에 있어서,A2는 산소이며;X는 -CONR5R6, -COOR7, -CO-R8또는 CN이며;R1은 수소 또는 알킬, 아릴, 할로겐, 히드록시, 아미노, 니트로, 시아노이며;R2, R3, R4는 동일하거나 상이하며, 이들 각각은 독립적으로 수소 또는 할로겐, 히드록시, 아미노, 니트로, 시아노, 아실, 아실옥시, 술포닐 유도체, 술피닐 유도체, 아미노 유도체, 카르복시, 에스테르, 에테르, 아미도, 술폰산, 술폰아미드, 알콕시카르보닐, 티오 유도체, 알킬, 알콕시, 옥시에스테르, 옥시아미도, 아릴, 옥시 유도체, 헤테로사이클, 비닐이고, R3은 추가적으로 C2-5 알케닐, C2-5 알키닐 또는 아지도(이들 각각은 선택적으로 할로겐, 시아노, 티오시아노, 아지도, 시클로프로필, 아실 및/또는 페닐중 하나 이상에 의해 치환됨); 또는 페닐술포닐옥시(페닐 부분은 하나 이상의 할로겐, 알킬, 할로알킬, 알콕시, 니트로, 아미노 및/또는 페닐에 의해 치환될 수 있음)이며;R2a, R3a및 R4a는 수소이며;R5, R6, R7은 동일하거나 상이하며, 이들 각각은 독립적으로, 수소, 히드록시, 알킬, 아릴, 헤테로사이클 또는 옥시 유도체이고;R8은 수소, 히드록시, 티올, 할로겐, 알킬, 아릴, 헤테로사이클, 알킬티오 또는 티오 유도체임을 특징으로 하는 화합물.
- 제 14 항에 있어서,R1이 메틸, 에틸, 프로필, 이소프로필, 부틸 또는 이소부틸이며;R2및 R4가 독립적으로 수소 또는 할로겐 또는 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸이며;R3이 C1-5 알킬, C2-5 알케닐, C2-C5 알키닐, 시클로프로필, 아지도(이들 각각은 할로겐, 시아노, 티오시아노, 아지도, 알킬티오, 시클로프로필, 아실 및/또는 페닐중 하나 이상에 의해 선택적으로 치환됨); 페닐; 페닐술포닐; 페닐술포닐옥시,테트라졸, 티아졸, 티에닐, 푸릴, 피롤, 피리딘(페닐 부분은 할로겐, 알킬, 할로알킬, 알콕시, 니트로, 아미노 및/또는 페닐중 하나 이상에 의해 치환될 수 있음); 가장 바람직하게는, 메틸, 에틸, 프로필, 이소프로필, 부틸 또는 이소부틸이며;X는 -COOH, -COOMe, -COOEt, -COOtBu 또는 -CONH2임을 특징으로 하는 화합물.
- 제 15 항에 있어서,R1이 메틸, 에틸 또는 n-프로필이며;R2및 R4가 각각 수소이고;X가 -CONH2임을 특징으로 하는 화합물.
- 제 1 항에 있어서,X가 -CA1NH2, -CA1NHCH3또는 -CA1N(CH3)2이며;R1이 알킬 또는 페닐이며;R3은 알킬, 알케닐, 알키닐, 시아노, 이소티오시아나토, 에테르, 카르복실, 아미도, 아릴 또는 헤테로사이클이거나,R3이 CH2R10(여기서, R10은 수소, 시클로알킬, 옥시에스테르, 옥시알킬술포닐, 옥시아릴술포닐, 아미노알킬술포닐, 아미노아릴술포닐, 니트로옥시, 시아노, 이소티오시아나토, 아지도, 알킬티오, 아릴티오, 알킬술피닐, 알킬술포닐, 헤테로사이클, 아릴옥시, 알콕시 또는 트리플루오로에틸임)이고;R3a는 수소, 알킬 또는 아릴이거나;R3과 R3a가 시클로알킬을 형성하고;R2, R2a, R4및 R4a가 각각 수소임을 특징으로 하는 화합물.
- 제 1 항에 있어서,R1이 알킬이며;R2, R2a, R3a및 R4a가 각각 수소이며;R3은 수소; C1-12-알킬(선택적으로 히드록시, 할로겐, 시아노, 티오시아나토 또는 알콕시로부터 선택된 하나 이상의 치환기에 의해 치환되고, 직접적으로, 또는 티오, 술피닐, 술포닐, 카르보닐 또는 옥시카르보닐기, 및 선택적으로 C1-4-알킬렌 가교를 통해 고리에 결합됨); C2-6-알케닐 또는 -알키닐(이들 각각은 선택적으로 하나 이상의 할로겐에 의해 치환됨); 아지도; 시아노; 아미도; 카르복시; 트리아졸릴, 테트라졸릴, 피롤리디닐, 피리딜, 1-옥시도피리딜, 티오몰폴리닐, 벤조디옥솔릴, 푸릴, 옥사졸릴, 피리미디닐, 피롤릴, 티아디아졸릴, 티아졸릴, 티에닐 또는 피페라지닐(이들 각각은 선택적으로 할로겐, C1-6-알킬 및 페닐로부터 선택된 하나 이상의 치환기에 의해 치환되고, 직접적으로, 또는 카르보닐기 또는 C1-4-알킬렌 가교를 통해 고리에 결합됨); 나프틸; 또는 페닐, 페닐알킬 또는 페닐알케닐(이들 각각은 선택적으로 할로겐, C1-6-알킬, C1-6 할로알킬, C1-6-알콕시, C1-6-알킬티오, 아미노, 아지도, 페닐 및 니트로로부터 선택된 하나 이상의 치환기에 의해 치환되고, 직접적으로, 또는 옥시, 술포닐, 술포닐옥시, 카르보닐 또는 카르보닐옥시기 및 선택적으로 추가적으로 C1-4-알킬렌 가교를 통해 고리에 결합됨)이며;R3a는 수소 또는 C1-4-알킬이고;R4및 R4a는 독립적으로, 수소, C1-4-알킬, 페닐 또는 벤질임을 특징으로 하는 화합물.
- 제 18 항에 있어서, R1이 a) C1-12-알킬; b) C1-6-알킬; 또는 c) 에틸로부터 선택된 치환기이고,존재하는 C1-4-알킬렌 가교가 메틸렌임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 라세미 형으로 존재하며, X가 -CONR5R6이고, R1이 수소, 메틸, 에틸 또는 프로필인 경우, 피롤리딘 고리상의 치환기는 모노-, 디- 또는 트리-메틸, 또는 모노-에틸 이외의 기임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 라세미 형으로 존재하고, X가 -CONR5R6이고, R1이 수소, 각각 비치환된 C1-6-알킬, C2-6-알케닐 또는 -알키닐, 또는 시클로알킬인 경우, 고리상의 치환기는 각각 알킬, 알케닐 또는 알키닐 이외의 비치환된 기임을 특징으로 하는 화합물.
- 제 1 항에 있어서,X가 -CA1NH2이며;R1이 수소이며;R3이 아지도메틸, 요오도메틸, 1 내지 5개의 할로겐 원자에 의해 선택적으로 치환된 C2-6-알킬, 1 또는 2개의 메틸 및/또는 1 내지 3개의 할로겐 원자에 의해 선택적으로 치환된 비닐, C1-4-알킬, 페닐 또는 할로겐에 의해 선택적으로 치환된 아세틸렌이며;R3a는 수소 또는 할로겐, 바람직하게는, 플루오르이고;R2, R2a, R4및 R4a가 각각 수소이며,라세미체 또는 거울상이성질체 부화형, 바람직하게는 순수 거울상이성질체임을 특징으로 하는 화합물.
- 제 1 항에 있어서,X가 -CA1NH2이며;R1이 수소이며;R3이 아지도, 옥시니트로, 1 내지 6개의 할로겐 원자에 의해 선택적으로 치환된 C1-6-알킬, C2-6-알케닐 또는 C2-6-알키닐이며;R3a는 수소 또는 할로겐, 바람직하게는, 플루오르이고;R2, R2a, R4및 R4a가 각각 수소이며,라세미체 또는 거울상이성질체 부화형, 바람직하게는 순수 거울상이성질체임을 특징으로 하는 화합물.
- 제 1 항에 있어서, A1및 A2가 산소이며; R1이 에틸이며; X가 -CONH2이고; R3이 n-프로필 또는 2,2-디플루오로비닐이며, 이외 모든 치환기는 수소임을 특징으로 하는 화합물.
- 하기 화학식 AA-Ⅱ의 화합물:상기 식에서, X, R1, R2, R3, R4, R2a, R3a및 R4a는 제 1 항에 정의된 바와 같으며,Q1은 Q1이 결합되어 있는 산소와 함께 이탈기를 형성한다.
- 제 25 항에 있어서, Q1이 a) 알킬; 또는 b) 선형 또는 분지형 C1-4-알킬로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 1 항 내지 제 26 항중의 어느 한 항에 있어서, 순수 거울상이성질체임을 특징으로 하는 화합물.
- 제 1 항 내지 제 27 항중의 어느 한 항에 있어서, R1이 결합되는 탄소 원자가 비대칭일 경우, "S"-구조를 띰을 특징으로 하는 화합물.
- 화합물 번호 8, 9, 10, 22, 23, 27, 30, 31, 32, 33, 38, 40, 41, 43, 46,47, 49, 64, 71, 72, 73, 75, 81, 83, 86, 87, 88, 92, 93, 95, 96, 98, 100, 103, 105, 110, 119, 127, 142, 146, 149, 151, 152, 156, 157, 158, 159, 162, 163, 164, 165, 166, 169, 170, 171, 173, 174, 175, 176, 180, 181, 185, 187, 188, 195, 196, 197, 198, 200, 201, 204, 205, 207, 209, 211, 212, 213, 214, 215, 219, 221, 222, 223, 224, 225, 226, 228, 229, 234, 250, 251, 252, 264, 265, 267, 304, 306, 350, 351, AA 1, AA 2, AA 3, AA 4 및 AA 5의 화합물 또는 이들의 약제학적으로 허용되는 염으로부터 선택된 화합물.
- (2S)-2-[(4S)-4-(2,2-디플루오로비닐)-2-옥소피롤리디닐]부탄아미드 또는 이것의 약제학적으로 허용되는 염.
- (2S)-2-[2-옥소-4-프로필피롤리디닐]부탄아미드 또는 이것의 약제학적으로 허용되는 염의 (4R) 및 (4S) 부분입체이성질체.
- 제 1 항 내지 제 31 항중의 어느 한 항에 따른 유효량의 화합물과 약제학적으로 허용되는 희석제 또는 담체를 포함하는 약제 조성물.
- 간질, 간질발생, 발작 질환, 경련, 및 양극성 장애, 조병, 우울증, 불안증, 편두통, 삼차 및 기타 신경통, 만성 통각, 신경병증성 통각, 뇌빈혈, 심장성 부정백, 근간장증, 코카인 남용, 스트로크(stroke), 간대성근경련, 본태성 진전증 및기타 운동 장애, 신생아 대뇌 출혈, 근위축성 축삭 경화증, 강직, 파킨슨병 및 기타 퇴행성 질환을 포함하는 기타 신경 질환, 기관지 천식, 천식 지속상태 및 알레르기성 기관지염, 천식 신드롬, 기관지 과민성 및 기관지경련성 신드롬(bronchospastic syndromes)과 알레르기성 및 혈관운동성 비염 및 리노컨정티버티(rhinoconjunctivity)의 치료용 약제 제조를 위한 제 1 항 내지 제 32 항중의 어느 한 항에 따른 화합물의 용도.
- 치료학적 용량의 제 1 항 내지 제 33항에 따른 하나 이상의 화합물을 투여하는 것을 포함하여, 간질, 간질발생, 발작 질환, 경련, 및 양극성 장애, 조병, 우울증, 불안증, 편두통, 삼차 및 기타 신경통, 만성 통각, 신경병증성 통각, 뇌빈혈, 심장성 부정백, 근간장증, 코카인 남용, 스트로크, 간대성근경련, 본태성 진전증 및 기타 운동 장애, 신생아 대뇌 출혈, 근위축성 축삭 경화증, 강직, 파킨슨병 및 기타 퇴행성 질환을 포함하는 기타 신경 질환, 기관지 천식, 천식 지속상태 및 알레르기성 기관지염, 천식 신드롬, 기관지 과민성 및 기관지경련성 신드롬과 알레르기성 및 혈관운동성 비염 및 리노컨정티버티의 치료가 요구되는 포유동물에서 이러한 질환을 치료하는 방법.
- 간질, 간질발생, 발작 질환, 경련, 및 양극성 장애, 조병, 우울증, 불안증, 편두통, 삼차 및 기타 신경통, 만성 통각, 신경병증성 통각, 뇌빈혈, 심장성 부정백, 근간장증, 코카인 남용, 스트로크, 간대성근경련, 본태성 진전증 및 기타 운동장애, 신생아 대뇌 출혈, 근위축성 축삭 경화증, 강직, 파킨슨병 및 기타 퇴행성 질환을 포함하는 기타 신경 질환, 기관지 천식, 천식 지속상태 및 알레르기성 기관지염, 천식 신드롬, 기관지 과민성 및 기관지경련성 신드롬과 알레르기성 및 혈관운동성 비염 및 리노컨정티버티 치료용 약제 제조를 위한,각각의 치환기가 제 1 항에 정의된 바와 같으며, 단 R2, R3, R4, R2a, R3a및 R4a중 하나 이상이 수소이고; 화합물이 모든 가능한 이성질체의 혼합물이고, X가 -CONR5R6이며, A2가 산소이고, R1이 수소, 메틸, 에틸 또는 프로필인 경우, 피롤리딘 고리상의 치환기가 모노-, 디- 또는 트리-메틸, 또는 모노-에틸 이외의 기인 제 1 항에 설명된 화학식 Ⅰ의 화합물 또는 이것의 약제학적으로 허용되는 염의 용도.
- 각각의 치환기가 제 1 항에 정의된 바와 같으며, 단 R2, R3, R4, R2a, R3a및 R4a중 하나 이상이 수소이고; 화합물이 모든 가능한 이성질체의 혼합물이고, X가 -CONR5R6이며, A2가 산소이고, R1이 수소, 메틸, 에틸 또는 프로필인 경우, 피롤리딘 고리상의 치환기가 모노-, 디- 또는 트리-메틸, 또는 모노-에틸 이외의 기인 제 1 항에 설명된 화학식 Ⅰ의 화합물 또는 이것의 약제학적으로 허용되는 염의 치료학적 용량을 투여하는 것을 포함하여,간질, 간질발생, 발작 질환, 경련, 및 양극성 장애, 조병, 우울증, 불안증,편두통, 삼차 및 기타 신경통, 만성 통각, 신경병증성 통각, 뇌빈혈, 심장성 부정백, 근간장증, 코카인 남용, 스트로크, 간대성근경련, 본태성 진전증 및 기타 운동 장애, 신생아 대뇌 출혈, 근위축성 축삭 경화증, 강직, 파킨슨병 및 기타 퇴행성 질환을 포함하는 기타 신경 질환, 기관지 천식, 천식 지속상태 및 알레르기성 기관지염, 천식 신드롬, 기관지 과민성 및 기관지경련성 신드롬과 알레르기성 및 혈관운동성 비염 및 리노컨정티버티 치료가 요구되는 포유동물에서 이러한 질환을 치료하는 방법.
- 제 35 항에 있어서, 화학식 Ⅰ의 화합물이 제 29 항 내지 제 31 항중의 어느 한 항에 따른 화합물임을 특징으로 하는 용도.
- 제 36 항에 있어서, 화학식 Ⅰ의 화합물이 제 29 항 내지 제 31 항중의 어느 한 항에 따른 화합물임을 특징으로 하는 방법.
- 치료할 질환이 간질, 신경병증성 통각, 양극성 장애 또는 편두통임을 특징으로 하는 제 35 항 또는 제 37 항에 따른 용도, 또는 제 36 항 또는 제 38 항에 따른 방법.
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