KR100816185B1 - 2-옥소-1-피롤리딘 유도체, 이의 제조 방법 및 용도 - Google Patents
2-옥소-1-피롤리딘 유도체, 이의 제조 방법 및 용도 Download PDFInfo
- Publication number
- KR100816185B1 KR100816185B1 KR1020027010960A KR20027010960A KR100816185B1 KR 100816185 B1 KR100816185 B1 KR 100816185B1 KR 1020027010960 A KR1020027010960 A KR 1020027010960A KR 20027010960 A KR20027010960 A KR 20027010960A KR 100816185 B1 KR100816185 B1 KR 100816185B1
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- KR
- South Korea
- Prior art keywords
- oxo
- pyrrolidinyl
- butanamide
- alkyl
- hydrogen
- Prior art date
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- 0 *C(*)N(C(*)C(*)(*)C12**1)C2=O Chemical compound *C(*)N(C(*)C(*)(*)C12**1)C2=O 0.000 description 5
- ANWPENAPCIFDSZ-UHFFFAOYSA-N CCC(C(N)=O)N(CC(C1)C=C(F)F)C1=O Chemical compound CCC(C(N)=O)N(CC(C1)C=C(F)F)C1=O ANWPENAPCIFDSZ-UHFFFAOYSA-N 0.000 description 1
- VMXHHIUMVBUSJA-VEDVMXKPSA-N CCC(C(N)=O)N(C[C@H](CC(C)=O)C1)C1=O Chemical compound CCC(C(N)=O)N(C[C@H](CC(C)=O)C1)C1=O VMXHHIUMVBUSJA-VEDVMXKPSA-N 0.000 description 1
- MIZIQDGMNPHHDF-UHFFFAOYSA-N CCC(C(N=C)=O)N(CC(CC(C)O)C1)C1=O Chemical compound CCC(C(N=C)=O)N(CC(CC(C)O)C1)C1=O MIZIQDGMNPHHDF-UHFFFAOYSA-N 0.000 description 1
- ILUNORXMGQEJKB-UHFFFAOYSA-N CCC(C(OC(C)(C)C)=O)N(CC(C1)C(OC)=O)C1=O Chemical compound CCC(C(OC(C)(C)C)=O)N(CC(C1)C(OC)=O)C1=O ILUNORXMGQEJKB-UHFFFAOYSA-N 0.000 description 1
- CBFZBADOAOIQME-UHFFFAOYSA-N CCC(C(OC(C)(C)C)=O)N(CC(CO)C1)C1=O Chemical compound CCC(C(OC(C)(C)C)=O)N(CC(CO)C1)C1=O CBFZBADOAOIQME-UHFFFAOYSA-N 0.000 description 1
- KBKDDWVTAVXPGQ-UHFFFAOYSA-N CCC(CN(C(CC)C(OC(C)(C)C)=O)C=O)C=O Chemical compound CCC(CN(C(CC)C(OC(C)(C)C)=O)C=O)C=O KBKDDWVTAVXPGQ-UHFFFAOYSA-N 0.000 description 1
- VSMOMSSMHCAZBH-RFBVYIQQSA-N CC[C@@H](C(N)=O)N(CC(CC(C)OC(C)=O)C1)C1=O Chemical compound CC[C@@H](C(N)=O)N(CC(CC(C)OC(C)=O)C1)C1=O VSMOMSSMHCAZBH-RFBVYIQQSA-N 0.000 description 1
- GXIHOCRLQABMRM-MLWJPKLSSA-N CC[C@@H](C(N)=O)N(CC(CO)C1)C1=O Chemical compound CC[C@@H](C(N)=O)N(CC(CO)C1)C1=O GXIHOCRLQABMRM-MLWJPKLSSA-N 0.000 description 1
- XVTZQJRVBKEYAB-BDAKNGLRSA-N CC[C@@H](C(N)=O)N(C[C@H](CC=C)C1)C1=O Chemical compound CC[C@@H](C(N)=O)N(C[C@H](CC=C)C1)C1=O XVTZQJRVBKEYAB-BDAKNGLRSA-N 0.000 description 1
- NPCROIOLQIXKQJ-GDVGLLTNSA-N CC[C@@H](C(N)=O)NCC(C)O Chemical compound CC[C@@H](C(N)=O)NCC(C)O NPCROIOLQIXKQJ-GDVGLLTNSA-N 0.000 description 1
- PGXCKTFQPZRLFK-NHNAUAITSA-N CC[C@@H](C(N=C)=O)N(CC(CC(C)OC(C)=O)C1)C1=O Chemical compound CC[C@@H](C(N=C)=O)N(CC(CC(C)OC(C)=O)C1)C1=O PGXCKTFQPZRLFK-NHNAUAITSA-N 0.000 description 1
- KUOIAFDUOZFCME-UHFFFAOYSA-N O=C1[N-2]CC(CI)C1 Chemical compound O=C1[N-2]CC(CI)C1 KUOIAFDUOZFCME-UHFFFAOYSA-N 0.000 description 1
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- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
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Abstract
Description
융점은 뷔히 535 토톨리형 퓨전미터 (Buechi 535 Totoli-type fusionmetre)로 측정되며, 조절되지 않거나, 페르긴엘머 DSC 7에 대한 개시온도에 의해 조정된다.
Claims (50)
- 하기 화학식 Ⅰ의 화합물 또는 이것의 약제학적으로 허용되는 염:상기 식에서,X는 -CA1NR5R6이며;A1 및 A2는 산소이며;R1은 수소, C1-20알킬, 아릴 또는 -CH2-R1a(여기서, R1a는 아릴, 할로겐, 히드록시, 아미노, 니트로 또는 시아노임)이며;R3는 수소, 할로겐, 티올, 니트로, 니트로옥시, 시아노, 아지도, 카르복시, 아미도, 술폰산, 술폰아미드, C1-20 알킬, C2-6 알케닐, C2-6 알키닐, 에스테르, 에테르, 아릴, 테트라졸릴, 티아졸릴, 티에닐, 푸릴, 피롤릴, 피리디닐, C2-6 알키닐옥시, 아실옥시, 옥시에스테르, 옥시아미도, C1-6 알킬술포닐옥시, C1-6 알킬술피닐옥시, 아릴술포닐옥시, 아릴술피닐옥시, 아릴옥시, 아릴알콕시(여기서, 알콕시는 C1-6 알콕시임), C1-6 알킬티오, C2-6 알케닐티오, C2-6 알키닐티오, 아릴티오, 포르밀, 아세틸, 프로피오닐, 이소부티릴, 발레릴, 라우로일, 헵탄디오일, 시클로헥산카르보닐, 크로토노일, 푸르마로일, 아실로일, 벤조일, 나프토일, 4-카르복시부타노일, 옥살릴, 에톡살릴, 시스테이닐, 옥사모일, C1-6 알킬술포닐, C2-6 알케닐술포닐, C2-6 알키닐술포닐, 아릴술포닐, C1-6 알킬술피닐, C2-6 알케닐술피닐, C2-6 알키닐술피닐 또는 아릴술피닐이며;R3a는 수소, 할로겐, C1-20 알킬, C2-6 알케닐, C2-6 알키닐 또는 아릴이며;R5 및 R6은 동일하거나 상이하며, 각각 독립적으로 수소, 히드록시, C1-20 알킬, 아릴, C1-6 알콕시, C2-6 알케닐옥시, C2-6 알키닐옥시, 아실옥시, 옥시에스테르, 옥시아미도, C1-6 알킬술포닐옥시, C1-6 알킬술피닐옥시, 아릴술포닐옥시, 아릴술피닐옥시, 아릴옥시 또는 아릴알콕시(여기서, 알콕시는 C1-6 알콕시임)이며;단, R3 및 R3a 중 하나 이상은 수소 이외의 기이며,화합물이 모든 가능한 이성질체의 혼합물이고, X가 -CONR5R6이고, R1이 수소, 메틸, 에틸 또는 프로필인 경우, 피롤리딘 고리상의 치환기는 모노-, 디-메틸, 또는 모노-에틸 이외의 기이고;R1 및 R3a가 모두 수소이며, X가 -CONR5R6인 경우, R3은 카르복시, 에스테르, 아미도, 치환된 옥소-피롤리딘, C2-6 알키닐옥시, 아실옥시, 옥시에스테르, 옥시아미도, C1-6 알킬술포닐옥시, C1-6 알킬술피닐옥시, 아릴술포닐옥시, 아릴술피닐옥시, 아릴옥시, 아릴알콕시(여기서, 알콕시는 C1-6 알콕시임), 메틸, 나프틸, 할로겐 원자에 의해 파라 위치에서 또는 옥시 유도체에 의해 치환되거나 치환되지 않은 페닐기와 상이하며,"아릴"은 1 내지 3개의 고리로 이루어져 있으며, 하나의 수소 제거에 의해 6 내지 30개 탄소 원자를 함유하는 방향족 탄화수소로부터 유도된 유기 라디칼이며,"에스테르"는 화학식 -COO-R11의 기(여기서, R11은 C1-6 알킬, C2-6 알케닐, C2-6 알키닐, 아릴, 또는 아릴알킬(여기서, 알킬은 C1-6 알킬임)이며,"에테르"는 하나 이상의 산소 원자에 의해 방해된 C1-50-직쇄형 또는 분지형 알킬, 또는 C2-50-직쇄형 또는 분지형 알케닐 또는 알키닐기, 또는 이들의 배합물로부터 선택된 기이며,"아실"은 카르복실산으로부터 유도된 라디칼이며, R11이 상기 정의된 바와 같거나 수소 일 수 있는 화학식 R11-CO-의 기이다.
- 제 1 항에 있어서, X가 -CONR5R6(여기서, R5 및 R6은 수소, C1-4-알킬, 페닐 또는 C1-6 알킬페닐임)임을 특징으로 하는 화합물.
- 제 1 항에 있어서, R1이 수소, C1-20 알킬 또는 아릴로부터 선택된 치환기임을 특징으로 하는 화합물.
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- 제 1 항에 있어서, R3a가 수소, C1-20 알킬, 아릴 또는 아릴알킬(여기서, 알킬은 C1-6 알킬임)로부터 선택된 치환기임을 특징으로 하는 화합물.
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- 제 1 항에 있어서, R3a가 수소, 할로겐, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 3차-부틸 또는 2,2,2-트리메틸에틸, 또는 하나 이상의 할로겐 원자로 치환된 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 3차-부틸 또는 2,2,2-트리메틸에틸로부터 선택된 치환기임을 특징으로 하는 화합물.
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- 제 1 항에 있어서,A2는 산소이며;X는 -CONR5R6이며;R1은 수소 또는 C1-20 알킬, 아릴, 할로겐, 히드록시, 아미노, 니트로, 시아노이며;R3는 수소, 할로겐, 니트로, 시아노, 아실, 아실옥시, C1-6 알킬술포닐, C2-6 알케닐술포닐, C2-6 알키닐술포닐, 아릴술포닐, C1-6 알킬술피닐, C2-6 알케닐술피닐, C2-6 알키닐술피닐, 아릴술피닐, 카르복시, 에스테르, 에테르, 아미도, 술폰산, 술폰아미드, C1-6 알콕시카르보닐, C1-6 알킬티오, C2-6 알케닐티오, C2-6 알키닐티오, 아릴티오, 옥시에스테르, 옥시아미도, 아릴, C2-6 알키닐옥시, 아실옥시, 옥시에스테르, 옥시아미도, C1-6 알킬술포닐옥시, C1-6 알킬술피닐옥시, 아릴술포닐옥시, 아릴술피닐옥시, 아릴옥시, 아릴알콕시(여기서, 알콕시는 C1-6 알콕시임), 테트라졸릴, 티아졸릴, 티에닐, 푸릴, 피롤릴, 피리디닐, 비닐이며, R3은 추가적으로 C2-5 알케닐, C2-5 알키닐 또는 아지도(이들 각각은 하나 이상의 할로겐, 시아노, 티오시아노, 아지도, 시클로프로필, 아실 또는 페닐에 의해 치환되거나 비치환됨); 또는 페닐술포닐옥시(페닐 부분은 하나 이상의 할로겐, C1-6 알킬, C1-6 할로알킬, C1-6 알콕시, 니트로, 아미노 또는 페닐에 의해 치환될 수 있음)이며;R3a는 수소이며;R5 및 R6은 동일하거나 상이하며, 이들 각각은 독립적으로, 수소, 히드록시, C1-20 알킬, 아릴, C1-6 알콕시, C2-6 알케닐옥시, C2-6 알키닐옥시, 아실옥시, 옥시에스테르, 옥시아미도, C1-6 알킬술포닐옥시, C1-6 알킬술피닐옥시, 아릴술포닐옥시, 아릴술피닐옥시, 아릴옥시 또는 아릴알콕시(여기서, 알콕시는 C1-6 알콕시임)임을 특징으로 하는 화합물.
- 제 14 항에 있어서,R1이 메틸, 에틸, 프로필, 이소프로필, 부틸 또는 이소부틸이며;R3이 C1-5 알킬, C2-5 알케닐, C2-5 알키닐, 시클로프로필, 아지도(이들 각각은 하나 이상의 할로겐, 시아노, 티오시아노, 아지도, C1-6 알킬티오, 시클로프로필, 아실 또는 페닐에 의해 치환되거나 비치환됨); 페닐; 페닐술포닐; 페닐술포닐옥시, 테트라졸, 티아졸, 티에닐, 푸릴, 피롤, 피리딘(페닐 부분은 하나 이상의 할로겐, C1-6 알킬, C1-6 할로알킬, C1-6 알콕시, 니트로, 아미노 또는 페닐에 의해 치환될 수 있음)이며;X는 -COOH 또는 -CONH2임을 특징으로 하는 화합물.
- 제 15 항에 있어서,R1이 메틸, 에틸 또는 n-프로필이며;X가 -CONH2임을 특징으로 하는 화합물.
- 제 1 항에 있어서,X가 -CA1NH2, -CA1NHCH3 또는 -CA1N(CH3)2이며;R1이 C1-20 알킬 또는 페닐이며;R3은 C1-20 알킬, C2-6 알케닐, C2-6 알키닐, 시아노, 이소티오시아나토, 에테르, 카르복실, 아미도, 아릴, 테트라졸릴, 티아졸릴, 티에닐, 푸릴, 피롤릴, 피리디닐이거나,R3이 CH2R10(여기서, R10은 수소, C3-8 시클로알킬, 옥시에스테르, C1-6 옥시알킬술포닐, 옥시아릴술포닐, C1-6 아미노알킬술포닐, 아미노아릴술포닐, 니트로옥시, 시아노, 이소티오시아나토, 아지도, C1-6 알킬티오, 아릴티오, C1-6 알킬술피닐, C1-6 알킬술포닐, 아릴, 테트라졸릴, 티아졸릴, 티에닐, 푸릴, 피롤릴, 피리디닐, 아릴옥시, C1-6 알콕시 또는 트리플루오로에틸임)이며;R3a는 수소, C1-20 알킬 또는 아릴임을 특징으로 하는 화합물.
- 제 1 항에 있어서,R1이 C1-20 알킬이며;R3a는 수소이며;R3은 수소; C1-12-알킬(히드록시, 할로겐, 시아노, 티오시아나토 또는 C1-6 알콕시로부터 선택된 하나 이상의 치환기에 의해 치환되거나 비치환됨); C2-6-알케닐 또는 -알키닐(이들 각각은 하나 이상의 할로겐에 의해 치환되거나 비치환됨); 아지도; 시아노; 아미도; 카르복시; 테트라졸릴, 피롤리디닐, 피리딜, 푸릴, 피롤릴, 티아졸릴 또는 티에닐(이들 각각은 할로겐, C1-6-알킬 및 페닐로부터 선택된 하나 이상의 치환기에 의해 치환되거나 비치환되며, 고리에 직접적으로 결합되거나 C1-4-알킬렌 브릿지를 통해 결합됨); 나프틸; 또는 페닐, 페닐알킬 또는 페닐알케닐(여기서, 알킬은 C1-6 알킬이고, 알케닐은 C1-6 알케닐이고; 상기 치환기 각각은 할로겐, C1-6-알킬, C1-6 할로알킬, C1-6-알콕시, C1-6-알킬티오, 아미노, 아지도, 페닐 및 니트로로부터 선택된 하나 이상의 치환기에 의해 치환되거나 비치환됨)임을 특징으로 하는 화합물.
- 제 18 항에 있어서, R1이 에틸임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 라세미 형으로 존재하며, X가 -CONR5R6이고, R1이 수소, 메틸, 에틸 또는 프로필인 경우, 피롤리딘 고리상의 치환기는 모노-, 디-메틸, 또는 모노-에틸 이외의 기임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 라세미 형으로 존재하고, X가 -CONR5R6이고, R1이 수소, 또는 각각 비치환된 C1-6-알킬, C2-6-알케닐, C2-6-알키닐 또는 C3-8 시클로알킬인 경우, 고리상의 치환기는 각각 비치환된 알킬, 알케닐 또는 알키닐 이외의 기임을 특징으로 하는 화합물.
- 제 1 항에 있어서,X가 -CA1NH2이며;R1이 수소이며;R3이 아지도메틸, 요오도메틸, 1개 내지 5개의 할로겐 원자로 치환되거나 비치환된 C2-6-알킬, 하나 또는 두개의 메틸 또는 1개 내지 3개의 할로겐으로 치환되거나 비치환된 비닐, C1-4-알킬로 치환되거나 비치환된 아세틸렌, 페닐 또는 할로겐이고;R3a는 수소 또는 할로겐이고;라세미체 또는 거울상이성질체가 풍부한 형태(enantiomerically enriched form)임을 특징으로 하는 화합물.
- 제 1 항에 있어서,X가 -CA1NH2이며;R1이 수소이며;R3이 아지도, 옥시니트로, 1 내지 6개의 할로겐 원자에 의해 치환되거나 치환되지 않은 C1-6-알킬, C2-6-알케닐 또는 C2-6-알키닐이며;R3a는 수소 또는 할로겐이고;라세미체 또는 거울상이성질체가 풍부한 형태임을 특징으로 하는 화합물.
- 제 1 항에 있어서, A2가 산소이며; R1이 에틸이며; X가 -CONH2이고; R3이 n-프로필 또는 2,2-디플루오로비닐이며, R3a가 수소임을 특징으로 하는 화합물.
- 제 25 항에 있어서, Q1이 C1-20-알킬임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 순수 거울상이성질체임을 특징으로 하는 화합물.
- 제 1 항에 있어서, R1이 결합되는 탄소 원자가 비대칭일 경우, "S"-배열을 가짐을 특징으로 하는 화합물.
- (2S)-2-[4-(브로모메틸)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[(4R)-4-(요오도메틸)-2-옥소피롤리디닐]부탄아미드;(2S)-2-(2-옥소-4-페닐-1-피롤리디닐)부탄아미드;(2S)-2-[4-(요오도메틸)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[4-(클로로메틸)-2-옥소-1-피롤리디닐]부탄아미드;{1-[(1S)-1-(아미노카르보닐)프로필]-5-옥소-3-피롤리디닐}메틸 4-메틸벤젠술포네이트;(2S)-2-[(4R)-4-(아지도메틸)-2-옥소피롤리디닐]부탄아미드;2-[4-(2,2-디브로모비닐)-2-옥소-1-피롤리디닐]부탄아미드;{1-[(1S)-1-(아미노카르보닐)프로필]-5-옥소-3-피롤리디닐}메틸 니트레이트;(2S)-2-[2-옥소-4-(1H-테트라졸-1-일메틸)-1-피롤리디닐]부탄아미드;2-(2-옥소-4-비닐-1-피롤리디닐)부탄아미드;2-{2-옥소-4-[(페닐술포닐)메틸]-1-피롤리디닐}부탄아미드;(2S)-2-[(4R)-4-(2,2-디브로모비닐)-2-옥소피롤리디닐]부탄아미드;(2S)-2-[(4S)-4-(2,2-디브로모비닐)-2-옥소피롤리디닐]부탄아미드;(2S)-2-[4-(이소티오시아나토메틸)-2-옥소-1-피롤리디닐]부탄아미드;2-[2-옥소-4-(1,3-티아졸-2-일)-1-피롤리디닐]부탄아미드;(2S)-2-[2-옥소-4-(2-티에닐)-1-피롤리디닐]부탄아미드;(2S)-2-[4-(2-메톡시페닐)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[4-(3-메톡시페닐)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[4-(4-아지도페닐)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[2-옥소-4-(3-티에닐)-1-피롤리디닐]부탄아미드;(2S)-2-[4-(3-아지도페닐)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[2-옥소-4-(3-티에닐)-1-피롤리디닐]부탄아미드;(2S)-2-[(4S)-2-옥소-4-비닐피롤리디닐]부탄아미드;(2S)-2-[(4R)-2-옥소-4-비닐피롤리디닐]부탄아미드;2-[4-(2-브로모페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[2-옥소-4-(3-피리디닐)-1-피롤리디닐]부탄아미드;(25)-2-(4-[1,1'-비페닐]-4-일-2-옥소-1-피롤리디닐)부탄아미드;(2S)-2-{4-[(메틸술파닐)메틸]-2-옥소-1-피롤리디닐}부탄아미드;2-[4-(요오도메틸)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[(4R)-4-(요오도메틸)-2-옥소-1-피롤리디닐]펜탄아미드;(2S)-2-[(4R)-4-(요오도메틸)-2-옥소피롤리디닐]프로판아미드;2-(2-옥소-4-프로필-1-피롤리디닐)프로판아미드;2-(2-옥소-4-프로필-1-피롤리디닐)부탄아미드;2-(2-옥소-4-펜틸-1-피롤리디닐)부탄아미드;(2S)-2-[(4R)-4-(요오도메틸)-2-옥소피롤리디닐]-N-메틸부탄아미드;(25)-2-(4-네오펜틸-2-옥소-1-피롤리디닐)부탄아미드;(2S)-2-(4-에틸-2-옥소-1-피롤리디닐)부탄아미드;2-[4-(2,2-디플루오로비닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[4-(2,2-디플루오로에틸)-2-옥소-1-피롤리디닐]부탄아미드;2-{4-{(Z)-2-플루오로에테닐]-2-옥소-1-피롤리디닐}부탄아미드;2-[4-(2-메틸-1-프로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-(4-부틸-2-옥소-1-피롤리디닐)부탄아미드;2-[4-(시클로프로필메틸)-2-옥소-1-피롤리디닐]부탄아미드;2-(4-이소부틸-2-옥소-1-피롤리디닐)부탄아미드;2-[4-(4-클로로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[4-(3-클로로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-{2-옥소-4-[2-(트리플루오로메틸)페닐]-1-피롤리디닐}부탄아미드;2-[4-(2-플루오로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[4-(3-메틸페닐)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[2-옥소-4-(2-페닐에틸)-1-피롤리디닐]부탄아미드;(2S)-2-[4-(3-브로모페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-{4-[3,5-비스(트리플루오로메틸)페닐]-2-옥소-1-피롤리디닐}부탄아미드;2-[4-(3,4-디클로로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[4-(2,4-디클로로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[4-(2-푸릴)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[2-옥소-4-(3-페닐프로필)-1-피롤리디닐]부탄아미드;(2S)-2-[4-(3,5-디브로모페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[4-(3,4-디클로로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-(2-옥소-4-프로필-1-피롤리디닐)부탄아미드;2-[4-(3-클로로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-(4-에티닐-2-옥소-1-피롤리디닐)부탄아미드;2-[4-(2-플루오로페닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[4-(2-플루오로페닐)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[4-(시클로프로필메틸)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[2-옥소-4-(3,3,3-트리플루오로프로필)-1-피롤리디닐]부탄아미드;2-[4-(3-메틸페닐)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[4-(시클로프로필메틸)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-[(4R)-4-(2,2-디플루오로비닐)-2-옥소피롤리디닐]부탄아미드;(2S)-2-[2-옥소-4-(1H-피롤-1-일)-1-피롤리디닐]부탄아미드;(2S)-2-(4-알릴-2-옥소-1-피롤리디닐)부탄아미드;(2S)-2-[4-(2-요오도프로필)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-(4-알릴-2-옥소-1-피롤리디닐)부탄아미드;(2S)-2-[2-옥소-4-(2-옥소프로필)-1-피롤리디닐]부탄아미드;(2S)-2-[4-(2-브로모-1H-피롤-1-일)-2-옥소-1-피롤리디닐]부탄아미드;(2S)-2-(4-메틸-2-옥소-4-프로필-1-피롤리디닐)부탄아미드;(2R)-2-[4-(2,2-디클로로비닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[4-(브로모에틸닐)-2-옥소-1-피롤리디닐]부탄아미드;2-[(4S)-4-(2,2-디플루오로프로필)-2-옥소피롤리디닐]부탄아미드;(2S)-2-[4-(브로모에티닐)-2-옥소-1-피롤리디닐]부탄아미드;2-(2-옥소-4-프로필-1-피롤리디닐)펜탄아미드;3-시클로프로필-2-(2-옥소-4-프로필-1-피롤리디닐)프로판아미드;2-(2-옥소-4-프로필-1-피롤리디닐)-3-(1,3-티아졸-4-일)프로판아미드; 및2-(2-옥소-4-프로필-1-피롤리디닐)-4-펜텐아미드, 이의 모든 이성질형태 및 혼합물 또는 이의 약제학적으로 허용되는 염으로부터 선택된 화합물.
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- 약제학적으로 허용되는 희석제 또는 담체를 조합하여, 치료학적 용량의 제 1 항 내지 제 3 항, 제 6 항, 제 8 항, 제 14 항 내지 제 24 항 또는 제 27 항 내지 제 29 항 중 어느 한 항에 따른 화합물을 포함하여, 간질, 간질발생원, 발작 질환, 경련 및 양극성 장애, 조병, 우울증, 불안증, 편두통, 삼차 신경통, 만성 통증, 신경병증 통증, 뇌빈혈, 심부정맥, 근간장증, 코카인 남용, 뇌졸중, 간대성근경련, 본태성 진전증, 운동 장애, 신생아 대뇌 출혈, 근위축성 축삭 경화증, 경직, 파킨슨병 및 퇴행성 질환를 포함하는 신경 질환, 기관지 천식, 천식 지속상태 및 알레르기성 기관지염, 천식 신드룸, 기관지 과민성 및 기관지 경련성 신드룸(bronchospastic syndromes)과 알레르기성 및 혈관운동성 비염 및 리노컨정티버티(rhinoconjunctivity)를 치료하기 위한 약제 조성물.
- 약제학적으로 허용되는 희석제 또는 담체를 조합하여, 치료학적 용량의 제 29 항에 따른 화합물을 포함하여, 간질, 간질발생원, 발작 질환, 경련 및 양극성 장애, 조병, 우울증, 불안증, 편두통, 삼차 신경통, 만성 통증, 신경병증 통증, 뇌빈혈, 심부정맥, 근간장증, 코카인 남용, 뇌졸중, 간대성근경련, 본태성 진전증, 운동 장애, 신생아 대뇌 출혈, 근위축성 축삭 경화증, 경직, 파킨슨병 및 퇴행성 질환를 포함하는 신경 질환, 기관지 천식, 천식 지속상태 및 알레르기성 기관지염, 천식 신드룸, 기관지 과민성 및 기관지 경련성 신드룸(bronchospastic syndromes)과 알레르기성 및 혈관운동성 비염 및 리노컨정티버티(rhinoconjunctivity)를 치료하기 위한 약제 조성물.
- 제 33항에 있어서, 간질, 신경병증성 통증, 양극성 장애 또는 편두통을 치료하기 위한 약제 조성물.
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- 제 2 항에 있어서, X가 -CONH2임을 특징으로 하는 화합물.
- 제 3 항에 있어서, R1이 에틸임을 특징으로 하는 화합물.
- 제 6 항에 있어서, R3a가 수소 또는 C1-20 알킬로부터 선택된 치환기임을 특징으로 하는 화합물.
- 제 6 항에 있어서, R3a가 수소임을 특징으로 하는 화합물.
- 제 6 항에 있어서, R3이 C1-6-알킬 및 C2-6-할로알케닐로부터 선택된 치환기임을 특징으로 하는 화합물.
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- 제 25 항에 있어서, 에틸 3-({[(1S)-1-(아미노카르보닐)프로필]아미노}메틸)헥사노에이트 히드로클로라이드;2-(1-아다만틸)에틸 3-({[(1S)-1-(아미노카르보닐)프로필]아미노}메틸)헥사노에이트 히드로클로라이드;부틸 3-({[(1S)-1-(아미노카르보닐)프로필]아미노}메틸)헥사노에이트 히드로클로라이드 및이소프로필3-({[(1S)-1-(아미노카르보닐)프로필]아미노}메틸)헥사노에이트 히드로클로라이드, 이의 모든 이성질형태 및 혼합물 또는 이의 약제학적으로 허용되는 염으로 구성된 군으로부터 선택된 화합물.
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KR1020057016174A Division KR100681580B1 (ko) | 2000-02-23 | 2001-02-21 | 2-옥소-1-피롤리딘 유도체, 이의 제조 방법 및 용도 |
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US2836599A (en) | 1957-03-07 | 1958-05-27 | Aerojet General Co | Nu-(carboxyalkyl) dinitro lactams |
WO1999013911A1 (fr) * | 1997-09-12 | 1999-03-25 | Daiichi Pharmaceutical Co., Ltd. | Agent nootrope |
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Journal of organic chemistry 21, pp. 1211-1213, 1956 |
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