KR20100016076A - 신규 피롤리논 유도체 및 그것을 함유하는 의약 조성물 - Google Patents

신규 피롤리논 유도체 및 그것을 함유하는 의약 조성물 Download PDF

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KR20100016076A
KR20100016076A KR1020097022735A KR20097022735A KR20100016076A KR 20100016076 A KR20100016076 A KR 20100016076A KR 1020097022735 A KR1020097022735 A KR 1020097022735A KR 20097022735 A KR20097022735 A KR 20097022735A KR 20100016076 A KR20100016076 A KR 20100016076A
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히로유키 가이
šœ지 시노하라
다카유키 가메야마
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시오노기 앤드 컴파니, 리미티드
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Abstract

본 발명은 P2X3 및/또는 P2X2/3 길항제로서 유용한 화학식 1로 표시되는 화합물, 제약상 허용되는 염 또는 그들의 용매화물을 제공한다.
[화학식 1]
Figure 112009066584530-PCT00283
(상기 식에서, R1, R2, R3, Z1, Z2, Ra, Rb, q, A 및 n은 명세서에서 정의한 대로이다)

Description

신규 피롤리논 유도체 및 그것을 함유하는 의약 조성물{NOVEL PYRROLINONE DERIVATIVE AND MEDICINAL COMPOSITION CONTAINING THE SAME}
본 발명은 P2X 수용체, 특히 P2X3 및/또는 P2X2/3 수용체가 관여하는 질환 또는 상태를 치료하는데 유용한 화합물, 및 상기 화합물을 함유하는 의약 조성물에 관한 것이다.
ATP(아데노신3인산)는 세포내에서의 에너지원이나 인산화 기질로서 알려져 있는 한편, 세포외에서의 정보 전달 물질로서도 작용한다. ATP는 세포의 손상, 염증, 침해 자극, 혈중 산소 농도의 저하 등 다양한 자극에 의해 세포외로 방출되는 것 외에, 일차 감각신경 종말로부터 다른 신경전달물질과 동시에 세포외로 방출되는 것이 알려져 있다. 세포외로 방출된 ATP는 ATP 수용체을 통해서 각종의 세포외 정보 전달을 행한다(비특허문헌 6, 비특허문헌 7).
ATP 수용체는 이온 채널형의 P2X 패밀리와 G 단백질 공액형의 P2Y 패밀리로 크게 구별된다. P2X 수용체 패밀리로는 7종류의 서브 타입이 보고되어 있고, 호모 3량체 또는 다른 P2X 서브 타입과의 헤테로 3량체를 형성하여 비선택적 양이온 채널로서 기능한다(비특허문헌 8).
ATP가 통증을 야기하는 것은 이미 알려져 있고, 또한 P2X3의 녹아웃(Knockout)이나 녹다운(knockdown) 기술을 이용한 연구에 의해, P2X3 수용체는 만성 동통(疼痛)의 전달에 관여하고 있다는 것이 밝혀졌다. P2X3 수용체는 말초 감각 신경 특이적으로 발현하며, 호모 복합체 또는 P2X2와의 헤테로 복합체(P2X2/3)를 형성한다(비특허문헌 1).
그 후, P2X3 및 P2X2/3 수용체에 특이적인 길항제(拮抗劑; antagonist)로서 A-317491로 불리는 화합물이 보고되었다. A-317491은 다음 화학식으로 표시되는 삼치환-N-[(1S)-1,2,3,4-테트라하이드로-1-나프타레닐]벤즈아마이드 유도체이며(특허문헌 1), P2X3 및 P2X2/3 수용체에 대하여 길항제 활성을 나타내고, 랫트(rat)의 신경장애성 동통(neuropathic pain) 모델 및 염증성 동통 모델에 있어서 진통 작용을 나타내는 것이 보고되어 있다(비특허문헌 9). 이것은 P2X3 또는 P2X2/3 수용체를 통하여 통각이 전달되는 것, 그리고 P2X3 또는 P2X2/3 수용체 길항제가 진통제로서 유용하다는 것을 나타낸다. 또한, 특허문헌 2 내지 7에도 P2X3 또는 P2X2/3 수용체 길항 작용(receptor antagizing effect)을 나타내는 화합물이 기재되어 있다.
Figure 112009066584530-PCT00001
또한, P2X3 녹아웃 마우스가 현저한 방광(傍胱) 반사 저하를 나타내는 것이 최근 보고되고 있고(비특허문헌2), P2X3 길항약(拮抗藥)이 방광 과민에 기인하는 질환의 치료에 있어서도 유용한 것을 시사하고 있다.
본 발명에 따른 화합물과 유사한 화합물이 진통 활성을 나타내는 것이 비특허문헌 3 및 4에 기재되어 있지만, 어느 것이나 본 발명에 따른 화합물과는 구조가 다르다.
특허문헌 1: 국제 출원 공개 WO02/094767호 공보
특허문헌 2: 국제 출원 공개 WO2005/095359호 공보
특허문헌 3: 미국 출원 공개 US20070037974호 공보
특허문헌 4: 미국 출원 공개 US20070049758호 공보
특허문헌 5: 미국 출원 공개 US20070049610호 공보
특허문헌 6: 미국 출원 공개 US20070049609호 공보
특허문헌 7: 미국 출원 공개 US20070049534호 공보
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비특허문헌 2: J.Physiol. 567.2 (2005) pp.621-639
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비특허문헌 4: 파머슈티컬 케미스트리 저널(Pharmaceutical Chemistry Journal) Vol.31, No.5, (1997), pp.251-254
비특허문헌 5: Expert Opin. Ther. Patens (2006) 16(8) 113-1127.
비특허문헌 6: J. Physiology (2003), 554(2), 301-308
비특허문헌 7: J. Physiology (2003), 553(3), 683-694
비특허문헌 8: Pflungers Arch Eur J physiol (2006), 452, 513-537
비특허문헌 9: PNAS (2002), 99(26), 17179-17184
발명의 개시
발명이 해결하고자 하는 과제
본 발명은 신규한 P2X3 및/또는 P2X2/3 수용체 길항제를 제공한다.
과제를 해결하기 위한 수단
본 발명자들은 상기 목적을 달성하기 위해 예의 연구를 거듭한 결과, P2X3 및/또는 P2X2/3 수용체에 특이적으로 결합하여 길항 작용을 나타내는 신규 화합물을 발견하고, 이하에 기재하는 발명을 달성했다.
(1) 화학식 1로 표시되는 화합물, 또는 그 제약(製藥)상 허용되는 염 또는 그들의 용매화물을 함유하는 P2X3 및/또는 P2X2/3 수용체 길항제.
Figure 112009066584530-PCT00002
[상기 식에서, Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이며,
Z2는 ＝Ｏ 또는 ＝N―E(E는 수소, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 또는 치환기를 갖고 있어도 좋은 아미노)이거나, 또는
Figure 112009066584530-PCT00003
가
Figure 112009066584530-PCT00004
를 형성하고(R4및 R5는 각각 독립적으로 수소 또는 저급 알킬이고, R6은 수소, 치환기를 갖고 있어도 좋은 저급 알킬 또는 아실이며, r은 0 내지 2의 정수이다),
A는 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
Ra 및 Rb는 각각 독립적으로 수소 또는 저급 알킬이고,
q는 0 내지 4의 정수이고,
R1은 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알켄일, 치환기를 갖고 있어도 좋은 저급 알킨일, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노, 나이트로, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
n은 0 내지 3의 정수이고(단,
Figure 112009066584530-PCT00005
가
Figure 112009066584530-PCT00006
를 형성할 때, A―(Rl)n은 수소이어도 좋다),
R2는 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 사이클로 알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
R3은 수소, 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이다]
(2) Z1이 하이드록시이며, Z2가 ＝Ｏ인 상기 (1)에 기재된 P2X3 및/또는 P2X2/3 수용체 길항제.
(3) r이 0인 상기 (1)에 기재된 P2X3 및/또는 P2X2/3 수용체 길항제.
(4) 고리 A가 페닐, 피리딜 또는 싸이아졸릴인 상기 (1) 내지 (3)의 어느 것에 기재된 P2X3 및/또는 P2X2/3 수용체 길항제.
(5) R1이 치환기를 갖고 있어도 좋은 저급 알콕시카보닐 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 상기 (1) 내지 (4)의 어느 것에 기재된 P2X3 및/또는 P2X2/3 수용체 길항제.
(6) R2가 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 페닐 또는 치환기를 갖고 있어도 좋은 피리딜인 상기(1) 내지 (5)의 어느 것에 기재된 P2X3 및/또는 P2X2/3 수용체 길항제.
(7) R3이 탄소수 3 내지 10의 알킬, 사이클로알킬 또는 치환기를 갖고 있어도 좋은 페닐인 상기 (1) 내지 (6)의 어느 것에 기재된 P2X3 및/또는 P2X2/3 수용체 길항제.
(8) q가 0인 상기 (1) 내지 (7)의 어느 것에 기재된 P2X3 및/또는 P2X2/3 수용체 길항제.
(9) q가 1인 상기 (1) 내지 (7)의 어느 것에 기재된 P2X3 및/또는 P2X2/3 수용체 길항제.
(10) 화학식 2로 표시되는 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
Figure 112009066584530-PCT00007
[상기 식에서, Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이며,
Z2는 ＝Ｏ 또는 ＝N―E(E는 수소, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 또는 치환기를 갖고 있어도 좋은 아 미노)이거나, 또는
Figure 112009066584530-PCT00008
가
Figure 112009066584530-PCT00009
를 형성하고(R4 및 R5는 각각 독립적으로 수소 또는 저급 알킬이고, R6은 수소, 치환기를 갖고 있어도 좋은 저급 알킬 또는 아실이며, r은 0 내지 2의 정수이다),
고리 A 및 고리 B는 각각 독립적으로 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
R1a 및 R1b는 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알켄일, 치환기를 갖고 있어도 좋은 저급 알킨일, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노 또는 나이트로이고,
m 및 p는 각각 독립적으로 0 내지 2의 정수이고,
R2는 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아 릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이고,
R3은 수소, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
단, 고리 A가 피라졸론이고, 고리 B가 페닐인 화합물을 제외한다]
(11) Z1이 보호되어 있어도 좋은 알킬이고, Z2가 ＝Ｏ이며, R2가 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 상기 (10)에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
(12) r이 O이고, R2가 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 상기 (10)에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
(13) 고리 A가 페닐, 피리딜 또는 싸이아졸릴인 상기 (9) 내지 (12)의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
(14) 화학식 3으로 표시되는 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
Figure 112009066584530-PCT00010
[상기 식에서, Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이고,
Z2는 ＝Ｏ 또는 ＝N―E(E는 수소, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 또는 치환기를 갖고 있어도 좋은 아미노)이거나, 또는
Figure 112009066584530-PCT00011
가
Figure 112009066584530-PCT00012
를 형성하고(R4 및 R5는 각각 독립적으로 수소 또는 저급 알킬이고, R6은 수소, 치환기를 갖고 있어도 좋은 저급 알킬 또는 아실이며, r은 0 내지 2의 정수이다),
고리 A는 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
R1a는 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸 이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노 또는 나이트로이고,
m은 0 내지 2의 정수이고,
R1c 및 R1d는 각각 독립적으로는 수소 또는 치환기를 갖고 있어도 좋은 저급 알킬이고,
R2는 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
R3은 수소, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴, 치환기를 갖고 있어도 좋은 헤테로환식기이다]
(15) Z1이 보호되어 있어도 좋은 하이드록시이고, Z2가 ＝Ｏ이고, R2가 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 상기 (14)에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
(16) r이 0이고, R2가 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 상기 (14)에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
(17) 고리 A가 페닐, 피리딜 또는 싸이아졸릴인 상기 (14) 내지 (16)의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
(18) 상기 (10) 내지 (17)의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 함유하는 의약 조성물.
(19) 상기 (10) 내지 (17)의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 함유하는 P2X3 및/또는 P2X2/3 수용체 길항제.
(20) P2X3 및/또는 P2X2/3 수용체가 관여하는 질환의 치료 및/또는 예방을 위한 상기 (10) 내지 (17)의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물의 사용.
(21) 상기 (10) 내지 (17)의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 투여하는 것을 특징으로 하는 P2X3 및/또는 P2X2/3 수용체가 관여하는 질환의 치료 및/또는 예방 방법.
또한, 다른 태양으로서 이하에 기재하는 발명을 달성했다.
(1') 화학식 1로 표시되는 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 함유하는 P2X3 또는 P2X2/3 수용체 길항제.
[화학식 1]
Figure 112009066584530-PCT00013
[상기 식에서, Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이며,
Z2는 O 또는 NOH이거나, 또는
Figure 112009066584530-PCT00014
가
Figure 112009066584530-PCT00015
를 형성하고(R4 및 R5는 각각 독립적으로 수소 또는 저급 알킬, R6은 수소, 저급 알킬 또는 아실, r은 0 내지 2의 정수이다),
A는 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
Ra 및 Rb는 각각 독립적으로 수소 또는 저급 알킬이고,
q는 0 또는 1이고,
R1은 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노, 나이트로, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이고,
n은 0 내지 3의 정수이고, 단
Figure 112009066584530-PCT00016
가
Figure 112009066584530-PCT00017
를 형성할 때, A―(R1)n은 수소이어도 좋고,
R2는 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이고,
R3은 수소, 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 사이클로 알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이다]
(2') Z1이 하이드록시이고, Z2가 O인 상기 (1')에 기재된 P2X3 또는 P2X2/3 수용체 길항제.
(3') A가 페닐인 상기 (1') 또는 (2')에 기재된 P2X3 또는 P2X2/3 수용체 길항제.
(4') R1이 치환기를 갖고 있어도 좋은 저급 알콕시카보닐 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 상기 (1') 내지 (3')의 어느 것에 기재된 P2X3 또는 P2X2/3 수용체 길항제.
(5') R2가 치환기를 갖고 있어도 좋은 페닐 또는 치환기를 갖고 있어도 좋은 피리딜인 상기 (1') 내지 (4')의 어느 것에 기재된 P2X3 또는 P2X2/3 수용체 길항제.
(6') R3이 탄소수 3 내지 10의 알킬, 사이클로알킬 또는 치환기를 갖고 있어도 좋은 페닐인 상기 (1') 내지 (5')의 어느 것에 기재된 P2X3 또는 P2X2/3 수용체 길항제.
(7') q가 0인 상기 (1') 내지 (6')의 어느 것에 기재된 P2X3 또는 P2X2/3 수용체 길항제.
(8') 화학식 2로 표시되는 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
[화학식 2]
Figure 112009066584530-PCT00018
[상기 식에서, Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이며,
Z2는 O 또는 NOH이거나, 또는
Figure 112009066584530-PCT00019
가
Figure 112009066584530-PCT00020
를 형성하고(R4 및 R5는 각각 독립적으로 수소 또는 저급 알킬, R6은 수소, 저급 알킬 또는 아실, r은 0 내지 2의 정수이다),
고리 A 및 고리 B는 각각 독립적으로 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
R1a 및 R1b는 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노 또는 나이트로이고,
m 및 p는 각각 독립적으로 0 내지 2의 정수이고,
R2는 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이고,
R3은 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
단, 고리 A가 피라졸론이고, 고리 B가 페닐인 화합물을 제외한다)
(9') Z1이 보호되어 있어도 좋은 하이드록시이고, Z2가 O이고, R2가 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 상기 (8')에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
(10') 화학식 3으로 표시되는 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
[화학식 3]
Figure 112009066584530-PCT00021
[상기 식에서, Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이고,
Z2는 O 또는 NOH이거나, 또는
Figure 112009066584530-PCT00022
가
Figure 112009066584530-PCT00023
를 형성하고(R4 및 R5는 각각 독립적으로 수소 또는 저급 알킬, R6은 수소, 저급 알킬 또는 아실, r은 0 내지 2의 정수이다),
고리 A는 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
R1a는 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노 또는 나이트로이고,
m은 0 내지 2의 정수이고,
R1c 및 R1d는 각각 독립적으로는 수소 또는 치환기를 갖고 있어도 좋은 저급 알킬이고,
R2는 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이고,
R3은 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴, 치환기를 갖고 있어도 좋은 헤테로환식기이다]
(11') 상기 (8') 내지 (10')의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 함유하는 의약 조성물.
(12') 상기 (8') 내지 (10')의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 함유하는 P2X3 또는 P2X2/3 수용체 길항제.
(13') 진통제인 상기 (1') 내지 (7')의 어느 것에 기재된 P2X3 또는 P2X2/3 수용체 길항제.
(14') 상기 (8') 내지 (10')의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 함유하는 진통제.
(15') 상기 (1') 내지 (10')의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 투여하는 것을 특징으로 하는 진통방법.
(16') 진통제의 제조를 위한 상기 (1') 내지 (10')의 어느 것에 기재된 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물의 사용.
발명을 실시하기 위한 최선의 형태
본 발명의 화합물은 이하의 구조상 특징을 갖는다:
1) 기본 골격으로서 피롤린-2-온 고리를 갖는다 ;
2-1) 피롤린 고리의 3번 위치가 엔올형 하이드록실기이거나 ; 또는
2-2) 피롤린환의 3번 위치 및 4번 위치의 치환기가 함께 하기 화학식으로 표시되는 함질소 헤테로환을 형성한다 ;
Figure 112009066584530-PCT00024
(R4, R5, R6 및 r은 상기와 같다)
3) 피롤린환의 1번 위치의 질소가 하기 화학식으로 표시되는 기로 치환되어 있다. 단, 상기 (2-2)의 경우는 피롤린환의 1번 위치의 질소는 치환되어 있지 않아도 좋다;
Figure 112009066584530-PCT00025
(A, R1, Ra, Rb, n 및 q는 상기와 같다)
3-1) 피롤린환의 1번 위치의 질소가 하기 화학식으로 표시되는 기로 치환되어 있다 ;
Figure 112009066584530-PCT00026
(A, B, R1a, R1b, m 및 p는 상기와 같다)
3-2) 피롤린환의 1번 위치의 질소가 하기 화학식으로 표시되는 기로 치환되어 있다.
Figure 112009066584530-PCT00027
(A, R1a, R1c, R1d 및 m은 상기와 같다)
한편, 화학식 1, 화학식 2 및 화학식 3에 있어서, n, m 및/또는 p가 2 이상의 정수인 경우, 각각 복수의 R1, 복수의 R1a 및/또는 복수의 R1b는 각각 동일하여도 좋고, 다르더라도 좋다.
본 명세서 중에서 사용하는 용어를 이하에 설명한다. 각 용어는 특별히 기재하지 않는 한 이하의 의미를 갖는다.
「알킬」이란, 탄소수 1 내지 10, 바람직하게는 탄소수 1 내지 8, 더욱 바람직하게는 탄소수 1 내지 6의 직쇄 또는 분지쇄의 1가의 탄화수소기를 의미하며, 예컨대 메틸, 에틸, n-프로필, 아이소프로필, n-뷰틸, 아이소뷰틸, sec-뷰틸, tert-뷰틸, n-펜틸, 아이소펜틸, neo-펜틸, n-헥실, 아이소헥실, n-헵틸, 아이소헵틸, n-옥틸, 아이소옥틸, n-노닐 및 n-데실 등을 들 수 있다.
「저급 알킬」이란, 탄소수 1 내지 6, 바람직하게는 탄소수 1 내지 3의 직쇄 또는 분지쇄의 1가의 탄화수소기를 의미하며, 예컨대 메틸, 에틸, n-프로필, 아이소프로필, n-뷰틸, 아이소뷰틸, sec-뷰틸, tert-뷰틸, n-펜틸, 아이소펜틸, neo-펜틸, n-헥실, 아이소헥실 등을 들 수 있다.
「아실」이란, R―CO―로 표시되는 기를 의미한다(예컨대, R은 상기 「저급 알킬」 또는 후술의 「저급 알켄일」, 「아릴」, 「헤테로환식기」, 「사이클로알킬」 또는 「사이클로알켄일」이다).
「사이클로알킬」이란, 탄소수 3 내지 10의 단환식 또는 다환식 포화환식 탄소쇄를 의미한다. 단환식 사이클로알킬로서는, 예컨대 사이클로프로필, 사이클로뷰틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 사이클로노닐, 사이클로데실 등을 들 수 있다. 다환식 사이클로알킬로서는, 노보나닐 등을 들 수 있다.
「사이클로알켄일」이란, 적어도 하나의 탄소-탄소 이중결합을 포함하는 탄소수 3 내지 10의 비방향족 단환식 또는 다환식 고리계를 의미한다. 단환식 사이클로알켄일로서는, 사이클로펜텐일, 사이클로헥센일 등을 들 수 있다. 다환식 사이클로알켄일로서는 노보닐 등을 들 수 있다.
「아릴」이란, 단환 또는 축합환의 방향족 탄화수소를 의미하며, 예컨대 페닐, 1-나프틸, 2-나프틸, 안트릴, 페난트릴 및 인덴일 등을 들 수 있다.
「헤테로환식기」란, 고리 내에 질소원자, 산소원자, 및/또는 황원자를 적어도 1개 갖는 5 내지 7원자 고리, 그들이 2개 이상 축합한 고리 또는 고리내에 질소원자, 산소원자, 및/또는 황원자를 적어도 1개 갖는 5 내지 7원자 고리가 1이상인 상기 「아릴」, 「사이클로알킬」 또는 「사이클로알켄일」과 축합한 고리로부터 유도되는, 방향족 또는 비방향족의 단환식 또는 축합환식기를 의미한다. 예컨대, 피롤리닐, 피롤리디노, 피롤리디닐, 이미다졸리닐, 이미다졸리디닐, 피라졸리닐, 피라졸리디닐, 피페리디노, 피페리딜, 피페라디노, 피페라지닐, 모폴리닐, 모폴리노, 싸이오모폴리닐, 싸이오모폴리노, 테트라하이드로피란일, 다이하이드로피리딜, 다이하이드로피리다지닐, 다이하이드로피라진일, 다이옥사닐, 옥사싸이오라닐, 싸이아닐, 테트라하이드로퓨릴, 테트라하이드로피란일, 테트라하이드로싸이아졸리닐, 테트라하이드로아이소싸이아졸리닐 등의 비방향족 헤테로환식기,
피롤릴, 피라진일, 피라졸릴, 테트라졸릴, 퓨릴, 싸이엔일, 피리딜, 이미다졸릴, 트라이아졸릴, 테트라졸릴, 트라이아지닐, 피리다지닐, 피리미딘일, 피라진일, 아이소옥사졸릴, 싸이아졸릴, 아이소싸이아졸릴, 싸이아다이아졸릴, 옥사졸릴 및 옥사다이아졸릴 등의 단환 방향족 헤테로환식기, 및
인돌릴, 아이소인돌릴, 인다졸릴, 인돌리지닐, 인돌리닐, 아이소인돌리닐, 퀴놀릴, 아이소퀴놀릴, 신놀리닐, 프탈아지닐, 퀴나졸리닐, 나프티리디닐, 퀴녹살린일, 퓨리닐, 프테리디닐, 벤조피란일, 벤즈이미다졸릴, 벤즈아이소옥사졸릴, 벤즈옥사졸릴, 벤즈옥사다이아졸릴, 벤즈아이소싸이아졸릴, 벤조싸이아졸릴, 벤조싸이아다이아졸릴, 벤조퓨릴, 아이소벤조퓨릴, 벤조싸이엔일, 벤조트라이아졸릴, 이미다조피리딜, 트라이아조러피리딜, 이미다조싸이아졸릴, 피라지노피리다지닐, 벤즈이미다졸리닐, 벤조다이옥사닐, 테트라하이드로퀴놀린, 테트라하이드로벤조싸이엔일 등의 다른 고리와 축합한 헤테로환식기를 들 수 있다.
「할로젠」이란 불소, 염소, 브롬 및 요오드를 의미한다.
「저급 알콕시」란 RO―로 표시되는 기를 의미하고, 예컨대 R이 상기 저급 알킬과 같은 메톡시, 에톡시, 프로폭시, 아이소프로폭시, 뷰톡시, 아이소뷰톡시, sec-뷰톡시, tert-뷰톡시, 펜톡시, 아이소펜톡시, 네오펜톡시, 헥속시 등의 저급 알콕시를 들 수 있다.
「저급 알킬싸이오」란 RS―로 표시되는 기를 의미하고, 예컨대 R이 상기 저급 알킬과 같은 메틸싸이오, 에틸싸이오, 프로필싸이오, 아이소프로필싸이오, 뷰틸싸이오, 아이소뷰틸싸이오, sec-뷰틸싸이오, tert-뷰틸싸이오, 펜틸싸이오, 아이소펜틸싸이오, 네오펜틸싸이오, 헥실싸이오 등의 저급 알킬싸이오를 들 수 있다.
「저급 알콕시카보닐」이란 ROCO―로 표시되는 기를 의미하고, 예컨대 R이 상기 저급 알킬과 같은 메틸옥시카보닐, 에틸옥시카보닐, n-프로필옥시카보닐, 아이소프로필옥시카보닐, n-뷰틸옥시카보닐, tert-뷰틸옥시카보닐, n-헵틸옥시카보닐 등의 저급 알콕시카보닐을 들 수 있다.
「저급 알킬카밤오일」로서는, 예컨대 메틸카밤오일, 에틸카밤오일, n-프로필카밤오일, 아이소프로필카밤오일, n-뷰틸카밤오일, 다이메틸카밤오일, 다이에틸카밤오일, 다이프로필카밤오일기 등의 알킬 부분의 탄소수 1 내지 6의 모노 또는 다이 저급 알킬카밤오일기를 들 수 있다.
「치환기를 갖고 있어도 좋은 저급 알킬」, 「치환기를 갖고 있어도 좋은 저급 알켄일」,「치환기를 갖고 있어도 좋은 저급 알킨일」,「치환기를 갖고 있어도 좋은 저급 알콕시」,「치환기를 갖고 있어도 좋은 저급 알킬싸이오」,「치환기를 갖고 있어도 좋은 저급 알콕시카보닐」,「치환기를 갖고 있어도 좋은 저급 알킬카밤오일」의 치환기로서는, 이하로 이루어지는 군으로부터 선택되는 1개 또는 그 이상의 각각 동일 또는 다른 치환기를 들 수 있지만 이것으로 한정되지 않는다:
하이드록시, 카복시, 할로젠(F, Cl, Br, I), 할로 저급 알콕시(예컨대 CF3O), 사이클로알킬(예컨대 사이클로프로필), 사이클로알켄일(예컨대 사이클로프로펜일), 저급 알콕시(예컨대 메톡시, 에톡시, 프로폭시, 뷰톡시 등), 저급 알켄일옥시(예컨대 바이닐옥시, 알릴옥시 등), 저급 알콕시카보닐(예컨대 메톡시카보닐, 에톡시카보닐, tert-뷰톡시카보닐 등), 나이트로, 나이트로소, 아미노, 저급 알킬아미노(예컨대, 메틸아미노, 에틸아미노, 다이메틸아미노 등), 아실아미노(예컨대 아세틸아미노, 벤조일아미노 등), 아르알킬아미노(예컨대 벤질아미노, 트라이틸아미노), 하이드록시아미노, 이미노, 하이드록시이미노, 저급 알킬이미노(예컨대 메틸이미노, 에틸이미노, 다이메틸이미노 등), 저급 알콕시이미노(예컨대 메톡시이미노, 에톡시이미노 등), 아실이미노(예컨대 아세틸이미노, 벤조일이미노 등), 아자이도, 아릴(예컨대 페닐 등), 아르알킬(예컨대 벤질 등), 아르알킬옥시(예컨대, 벤질옥시), 사이아노, 아이소사이아노, 아이소사이아네이토, 싸이오사이아네이토, 아이소싸이오사이아네이토, 머캅토, 저급 알킬싸이오(예컨대 메틸싸이오 등), 저급 알킬설폰일(예컨대 메테인설폰일, 에탄설폰일), 카밤오일, 저급 알킬카밤오일(예컨대 메틸카밤오일, 에틸카밤오일, 다이메틸카밤오일 등), 설팜오일, 저급 알킬설팜오일, 아실(예컨대 폼일, 아세틸 등), 폼일옥시, 싸이오폼일, 싸이오카복시, 다이싸이오카복시, 싸이오카밤오일, 설피노, 설포, 하이드라지노, 아자이도, 유레이도, 아마이디노, 구아니디노, 프탈이미도, 트라이 저급 알킬실릴(트라이메틸실릴 등), 옥소, 및 이하의 실시예에서 나타내는 치환기.
「치환기를 갖고 있어도 좋은 아실」의 치환기는 상기「치환기를 갖고 있어도 좋은 저급 알킬」의 치환기와 같다. 아실(R―CO―)의 R이 「아릴」, 「헤테로환식기」, 「사이클로알킬」 또는 「사이클로알켄일」인 경우, 저급 알킬(예컨대 메틸, 에틸, 아이소프로필, tert-뷰틸 등), 할로 저급 알킬(예컨대, CF3, CH2CF3, CH2CCl3 등), 저급 알켄일, 저급 알킨일(예컨대 에틴일) 등을 치환기로 하고 있어도 좋다.
「치환기를 갖고 있어도 좋은 카밤오일」,「치환기를 갖고 있어도 좋은 설팜오일」의 치환기는 이하로 이루어지는 군으로부터 선택되는 1개 또는 그 이상의 각각 동일하거나 또는 다른 치환기를 들 수 있지만 이것으로 한정되지 않는다:
하이드록시, 카복시, 할로젠(F, Cl, Br, I), 저급 알켄일(예컨대 바이닐), 저급 알킨일(예컨대 에틴일), 사이클로알킬(예컨대 사이클로프로필), 사이클로알켄일(예컨대 사이클로프로펜일), 저급 알콕시카보닐(예컨대 메톡시카보닐, 에톡시카보닐, tert-뷰톡시카보닐 등), 아미노, 저급 알킬아미노(예컨대 메틸아미노, 에틸아미노, 다이메틸아미노 등), 아실아미노(예컨대 아세틸아미노, 벤조일아미노 등), 아르알킬아미노(예컨대 벤질아미노, 트라이틸아미노), 하이드록시아미노, 아릴(예컨대 페닐 등), 사이아노, 아이소사이아노, 아이소사이아네이토, 싸이오사이아네이토, 아이소싸이오사이아네이토, 아실(예컨대, 폼일, 아세틸 등) 및 이하의 실시예에서 나타내는 치환기.
「치환기를 갖고 있어도 좋은 아미노」의 치환기로서는, 이하로 이루어지는 군으로부터 선택되는 1개 또는 그 이상의 각각 동일하거나 또는 다른 치환기를 들 수 있지만 이것으로 한정되지 않는다:
하이드록시, 할로젠(F, Cl, Br, I), 할로 저급 알킬(예컨대 CF3, CH2CF3, CH2CCl3 등), 하이드록시 저급 알킬(예컨대 하이드록시에틸, ―C(CH3)2CH2OH 등) 할로 저급 알콕시(예컨대 CF3O), 저급 알킬(예컨대 메틸, 에틸, 아이소프로필, tert-뷰틸 등), 저급 알켄일(예컨대 바이닐), 저급 알킨일(예컨대 에틴일), 사이클로알킬(예컨대, 사이클로프로필), 사이클로알켄일(예컨대, 사이클로프로펜일), 저급 알콕시(예컨대 메톡시, 에톡시, 프로폭시, 뷰톡시 등), 저급 알킬옥시카보닐(tert-뷰틸옥시카보닐 등), 저급 알켄일옥시(예컨대 바이닐옥시, 알릴옥시 등), 아미노, 저급 알킬아미노(예컨대 메틸아미노, 에틸아미노, 다이메틸아미노 등), 아실아미노(예컨대 아세틸아미노, 벤조일아미노 등), 아르알킬아미노(예컨대 벤질아미노, 트라이틸아미노), 하이드록시아미노, 이미노, 하이드록시이미노, 저급 알킬이미노(예컨대 메틸이미노, 에틸이미노, 다이메틸이미노 등), 저급 알콕시이미노(예컨대 메톡시이미노, 에톡시이미노 등), 아실이미노(예컨대 아세틸이미노, 벤조일이미노 등), 아릴(예컨대 페닐 등), 아르알킬(예컨대 벤질 등), 사이아노, 아실(예컨대 폼일, 아세틸 등), 및 이하의 실시예에서 나타내는 치환기.
「치환기를 갖고 있어도 좋은 사이클로알킬」, 「치환기를 갖고 있어도 좋은 사이클로알켄일」, 「치환기를 갖고 있어도 좋은 아릴」, 「치환기를 갖고 있어도 좋은 헤테로환식기」, 「치환기를 갖고 있어도 좋은 페닐」, 「치환기를 갖고 있어도 좋은 피리딜」의 치환기로서는 이하로 이루어지는 군으로부터 선택되는 1개 또는 그 이상의 각각 동일하거나 또는 다른 치환기를 들 수 있지만 이것으로 한정되지 않는다:
하이드록시, 카복시, 할로젠(F, Cl, Br, I), 할로 저급 알킬(예컨대 CF3, CH2CF3, CH2CCl3 등), 할로 저급 알콕시(예컨대 CF3O), 저급 알킬(예컨대 메틸, 에틸, 아이소프로필, tert-뷰틸 등), 저급 알켄일(예컨대 바이닐), 저급 알킨일(예컨대 에틴일), 사이클로알킬(예컨대 사이클로프로필), 사이클로알켄일(예컨대 사이클로프로펜일), 저급 알콕시(예컨대 메톡시, 에톡시, 프로폭시, 뷰톡시 등), 저급 알켄일옥시(예컨대 바이닐옥시, 아릴옥시 등), 저급 알콕시카보닐(예컨대 메톡시카보닐, 에톡시카보닐, tert-뷰톡시카보닐 등), 나이트로, 나이트로소, 아미노, 저급 알킬아미노(예컨대 메틸아미노, 에틸아미노, 다이메틸아미노 등), 아실아미노(예컨대 아세틸아미노, 벤조일아미노 등), 아르알킬아미노(예컨대 벤질아미노, 트라이틸아미노), 하이드록시아미노, 이미노, 하이드록시이미노, 저급 알킬이미노(예컨대 메틸이미노, 에틸이미노, 다이메틸이미노 등), 저급 알콕시이미노(예컨대 메톡시이미노, 에톡시이미노 등), 아실이미노(예컨대 아세틸이미노, 벤조일이미노 등), 아자이도, 아릴(예컨대 페닐 등), 아르알킬(예컨대 벤질 등), 아르알킬옥시(예컨대 벤질옥시 등), 사이아노, 아이소사이아노, 아이소사이아네이토, 싸이오사이아네이토, 아이소싸이오사이아네이토, 머캅토, 저급 알킬싸이오(예컨대 메틸싸이오 등), 저급 알킬설폰일(예컨대 메테인설폰일, 에탄설폰일), 치환기를 갖고 있어도 좋은 카밤오일(예컨대 카밤오일, N-메틸-N-메톡시카밤오일 등), 치환기를 갖고 있어도 좋은 저급 알킬카밤오일(예컨대 메틸카밤오일, 에틸카밤오일, 다이메틸카밤오일, 하이드록시에틸카밤오일, 트라이플루오로메틸카밤오일, 트라이플루오로에틸카밤오일 등), 설팜오일, 저급 알킬설팜오일, 아실(예컨대 폼일, 아세틸 등), 폼일옥시, 싸이오폼일, 싸이오카복시, 다이싸이오카복시, 싸이오카밤오일, 설피노, 설포, 하이드라지노, 아자이도, 유레이도, 아마이디노, 구아니디노, 프탈이미도, 옥소, 및 이하의 실시예에서 나타내는 치환기.
여기서 할로 저급 알킬, 할로 저급 알콕시의 할로젠 부분은 상기「할로젠」과 같다.
할로 저급 알킬, 저급 알킬아미노, 저급 알킬이미노, 저급 알킬설폰일, 저급 알킬설팜오일, 저급 알킬카밤오일, 아르알킬 및 아르알킬아미노의 알킬 또는 저급 알킬 부분은 상기「저급 알킬」과 같다.
할로 저급 알콕시 및 저급 알콕시이미노의 저급 알콕시 부분은 상기「저급 알콕시」와 같다.
「저급 알켄일」이란, 임의의 위치에 1 이상의 이중결합을 갖는 탄소수 2 내지 6, 바람직하게는 탄소수 2 내지 3의 직쇄 또는 분지상의 알켄일을 포함한다. 구체적으로는 바이닐, 프로펜일, 아이소프로펜일, 뷰텐일, 아이소뷰텐일, 프렌일, 뷰타다이엔일, 펜텐일, 아이소펜텐일, 펜타다이엔일, 헥센일, 아이소헥센일 및 헥사다이엔일 등을 포함한다.
저급 알켄일옥시의 저급 알켄일 부분은 상기 「저급알켄일」과 같다.
「저급알킨일」이란, 탄소수 2 내지 6, 바람직하게는 탄소수 2 내지 3의 직쇄상 또는 분지상의 알킨일을 포함하고, 구체적으로는 에틴일, 프로핀일, 뷰틴일, 펜틴일 및 헥신일 등을 들 수 있다. 이들은 임의의 위치에 1 이상의 삼중결합을 갖고 있고, 추가로 이중결합을 갖고 있어도 좋다.
아르알킬아미노 및 아르알킬의 아릴 부분은 상기 「아릴」과 같다.
아실, 아실아미노 및 아실이미노의 아실 부분은 상기 「아실」과 같다.
「보호되어 있어도 좋은 하이드록시」 및 「보호되어 있어도 좋은 하이드록시아미노」에 있어서의 보호기는 당 분야에서 주지이며, 예컨대 에터 및 치환 에터 형성기(예컨대 메틸, 메톡시메틸, t-뷰톡시메틸, 1-에톡시에틸 및 벤질 등); 실릴에터 형성기(예컨대 트라이메틸실릴, 트라이에틸실릴, tert-뷰틸다이메틸실릴 및 메틸-다이아이소프로필실릴 등); 에스터 형성기(예컨대 폼산, 아세테이트 및 트라이클로로아세테이트 등); 카보네이트기(예컨대 메틸카보네이트, 2,2,2-트라이클로로에틸카보네이트, 및 p-나이트로페닐카보네이트 등); 설폰일 형성기(메테인설폰일, p-톨루엔설폰일) 등을 들 수 있다.
본 발명의 화합물 1, 2 또는 3에 있어서, 바람직한 태양은 이하와 같다.
Z1이 하이드록시 또는 하이드록시아미노인 화합물,
Z1이 하이드록시인 화합물,
Z2가 O 또는 NOH인 화합물,
Z2가 O인 화합물,
Figure 112009066584530-PCT00028
가
Figure 112009066584530-PCT00029
인 화합물,
A가 아릴 또는 헤테로환식기인 화합물,
A가 페닐인 화합물,
R2가 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 방향족 헤테로환식기(예컨대, 싸이엔일, 피리딜, 이미다졸릴, 피리미딘일, 아이소옥사졸릴, 싸이아졸릴, 아이소싸이아졸릴, 싸이아다이아졸릴, 옥사졸릴, 피라졸릴 및 옥사다이아졸릴 등)인 화합물,
R2가 치환기를 갖고 있어도 좋은 페닐인 화합물,
R3이 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 화합물,
R3이 알킬, 사이클로알킬, 치환기를 갖고 있어도 좋은 페닐 또는 치환기를 갖고 있어도 좋은 방향족 헤테로환식기(예컨대, 싸이엔일, 피리딜, 이미다졸릴, 피리미딘일, 아이소옥사졸릴, 싸이아졸릴, 아이소싸이아졸릴, 싸이아다이아졸릴, 옥사졸릴, 피라졸릴 및 옥사다이아졸릴, 퀴놀릴 등)인 화합물,
R3이 알킬, 사이클로알킬, 치환기를 갖고 있어도 좋은 페닐인 화합물.
본 발명의 화합물 1에 있어서, 바람직한 태양은 이하와 같다.
q가 0인 화합물,
n이 1 또는 2이고, R1은 할로젠, 치환기를 갖고 있어도 좋은 저급 알킬, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 화합물,
n이 1 또는 2이고, R1은 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 화합물,
n이 1또는 2이고, R1은 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 페닐, 치환기를 갖고 있어도 좋은 비방향족 헤테로환식기(예컨대 다이옥소라닐, 이미다졸리닐, 이미다졸리디닐, 피라졸리닐, 아이소옥사졸리닐, 옥사졸리닐, 싸이아졸리닐, 아이소싸이아졸리닐 등), 치환기를 갖고 있어도 좋은 방향족 헤테로환식기인 화합물인 화합물(예컨대 싸이엔일, 피리딜, 이미다졸릴, 피리미딘일, 아이소옥사졸릴, 싸이아졸릴, 아이소싸이아졸릴, 싸이아다이아졸릴, 옥사졸릴, 피라졸릴및 옥사다이아졸릴 등).
본 발명의 화합물 2에 있어서, 바람직한 태양은 이하와 같다.
고리 B가 치환기를 갖고 있어도 좋은 비방향족 헤테로환식기(예컨대 다이옥소라닐, 이미다졸리닐, 이미다졸리디닐, 피라졸리닐, 아이소옥사졸리닐, 옥사졸리닐, 싸이아졸리닐, 아이소싸이아졸리닐 등), 치환기를 갖고 있어도 좋은 방향족 헤테로환식기인 화합물(예컨대 싸이엔일, 피리딜, 이미다졸릴, 피리미딘일, 아이소옥사졸릴, 싸이아졸릴, 아이소싸이아졸릴, 싸이아다이아졸릴, 옥사졸릴, 피라졸릴 및 옥사다이아졸릴 등),
m 및 p가 각각 독립적으로 0 또는 1의 정수이며, R1a 및 R1b가 각각 독립적으로 할로젠, 하이드록시, 저급 알킬 또는 저급 알콕시인 화합물.
본 발명의 화합물 3에 있어서, 바람직한 태양은 이하와 같다.
m이 0 또는 1의 정수이며, R1a가 할로젠, 하이드록시, 저급 알킬 또는 저급 알콕시인 화합물,
R1c가 수소, 치환기를 갖고 있어도 좋은 저급 알킬인 화합물,
R1d가 수소, 치환기를 갖고 있어도 좋은 저급 알킬인 화합물,
R1c 및 R1d가 각각 독립적으로 수소 또는 치환기를 갖고 있어도 좋은 저급 알킬인 화합물.
본 발명 화합물의 일반적 합성 방법을 이하에 나타낸다. 이들 합성에 이용하는 출발 물질 및 반응 시약은 어느 것이라도, 상업적으로 입수 가능하거나 또는 상업적으로 입수 가능한 화합물을 이용하여, 당 분야에서 주지된 방법에 따라서 제조할 수 있다.
본 발명의 화합물 1(즉, 화학식 1로 표시되는 화합물. 이하, 다른 식으로 표시되는 화합물에 관해서도 이와 같이 약기하기도 한다)은 예컨대 이하에 나타내는 합성 경로(route)에 의해서 제조할 수 있다.
[경로 1]
Figure 112009066584530-PCT00030
[상기 식에서, R7은 저급 알킬이며, 그 밖의 기호는 상기와 같다]
즉, 화학식 (Ia)로 표시되는 본 발명의 화합물은 화합물 (Ⅱ), 화합물 (Ⅲ) 및 화합물 (Ⅳ)를 산의 존재 하, 또는 비존재 하, 무용매 또는 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다.
본 반응에 있어서, 화합물 (Ⅲ) 및 화합물 (Ⅳ)는 화합물 (Ⅱ)에 대하여 1 당량 또는 그 이상, 바람직하게는 1 내지 3당량 사용할 수 있다.
사용할 수 있는 산으로서는 아세트산, 파라톨루엔 설폰산, 염산 등을 들 수 있다.
사용할 수 있는 용매로서는 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화 탄화수소류(예, 사이클로헥세인, 헥세인 등), 에터류(예, 테트라하이드로퓨란, 다이에틸에터, 다이옥세인 등) 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 -10 내지 150℃, 바람직하게는 20 내지 100℃이다. 반응 시간은 화합물에 따라 다르지만 10분 내지 80시간 반응시키면 좋다.
수득된 원하는 화합물 (Ia)는 필요하다면 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
[경로 2]
Figure 112009066584530-PCT00031
[반응식 중의 기호는 상기와 같다]
즉, 화학식 (Ia)로 표시되는 본 발명의 화합물은 화합물 (Ⅱ) 및 화합물 (Ⅴ)를 산 존재 하, 또는 비존재 하에서, 무용매 또는 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다.
본 반응에 있어서, 화합물 (Ⅴ)는 화합물 (Ⅱ)에 대하여 1당량 또는 그 이상, 바람직하게는 1 내지 3당량 사용할 수 있다.
사용할 수 있는 산으로서는 아세트산, 파라톨루엔 설폰산, 염산 등을 들 수 있다.
사용할 수 있는 용매로서는, 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화 탄화수소류(예, 사이클로헥세인, 헥세인 등), 에터류(예, 테트라하이드로퓨란, 다이에틸에터, 다이옥세인 등) 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 -10 내지 150℃, 바람직하게는 20 내지 100℃이다. 반응 시간은 화합물에 따라 다르지만 10분 내지 80시간 반응시키면 좋다.
수득된 원하는 화합물 (Ia)는 필요하다면 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
[경로 3]
Figure 112009066584530-PCT00032
[상기 식에서, L 및 Q는 한쪽이 다이하이드록시보레인, 다이 저급 알킬보레인 또는 다이 저급 알콕시보레인을 나타내고, 다른 쪽은 할로젠 또는 ―OSO2(CsF2s+1)(s는 1 내지 4의 정수)을 나타내고, 다른 기호는 상기와 같다.]
즉, 화학식 (Ib)로 표시되는 본 발명의 화합물은 스즈키 커플링 반응을 이용하여, 화합물 (Ⅵ) 및 화합물 (Ⅶ)을 팔라듐 촉매 및 염기 존재 하, 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다.
본 반응에 있어서, 화합물 (Ⅶ)은 화합물 (Ⅵ)에 대하여 1당량 또는 그 이상, 바람직하게는 1 내지 3당량 사용할 수 있다.
사용할 수 있는 염기로서는, 예컨대 금속 수산화물(예, 수산화나트륨, 수산화칼륨 등), 금속 수소화물(예, 수소화나트륨, 수소화리튬 등), 금속 탄산염(예, 탄산나트륨, 탄산칼륨, 탄산세슘 등) 등을 들 수 있고, 화합물 (Ⅵ)에 대하여 1당량 또는 그 이상, 바람직하게는 1 내지 5당량 사용할 수 있다.
사용할 수 있는 팔라듐 촉매로서는, 예컨대 트리스(다이벤질리덴아세톤)다이팔라듐(O), 아세트산 팔라듐(Ⅱ), 다이클로로비스트라이페닐포스핀팔라듐(Ⅱ) 또는 테트라키스(트라이페닐포스핀)팔라듐(Ⅱ) 등을 들 수 있고, 화합물 (Ⅵ)에 대하여 0.001당량 또는 그 이상, 바람직하게는 0.01 내지 1당량 사용할 수 있다.
사용할 수 있는 용매로서는, 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화탄화수소류(예, 사이클로헥세인, 헥세인 등), 에터류(예, 테트라하이드로퓨란, 다이에틸에터, 다이옥세인, 다이메톡시에테인 등), N, N-다이메틸폼아마이드, 물 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 -10 내지 180℃, 경우에 따라서는 마이크로웨이브 조사화(照射化), 바람직하게는 20 내지 120℃이다. 반응 시간은 화합물에 따라 다르지만 10분 내지 80시간 반응시키면 좋다.
수득된 원하는 화합물 (Ib)는 필요하다면 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
[경로 4]
Figure 112009066584530-PCT00033
[상기 식에서, L 및 M은 한쪽이 트라이알킬주석(예, ―SnBu 등)을 나타내고, 다른 쪽은 할로젠 또는 ―OSO2(CsF2s+1)(s는 1 내지 4의 정수)을 나타내며, 다른 기호는 상기와 같다.]
즉, 화학식 (Ib)로 표시되는 본 발명의 화합물은 스틸 커플링(Stille coupling) 반응을 이용하여, 화합물 (Ⅵ) 및 화합물 (Ⅷ)을 촉매 존재 하, 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다.
본 반응에 있어서, 화합물 (Ⅷ)은 화합물 (Ⅵ)에 대하여 1당량 또는 그 이상, 바람직하게는 1 내지 3당량 사용할 수 있다.
사용할 수 있는 촉매로서는, 예컨대 트리스(다이벤질리덴아세톤)다이팔라듐(0), 아세트산팔라듐(Ⅱ), 다이클로로비스트라이페닐포스핀팔라듐(Ⅱ) 또는 테트라키스(트라이페닐포스핀)팔라듐(Ⅱ) 등을 들 수 있고, 화합물 (Ⅵ)에 대하여 0.001당량 또는 그 이상, 바람직하게는 0.01 내지 1당량 사용할 수 있다. 필요에 따라, 촉매의 2배 몰의 포스핀 리간드, 예컨대 트라이-tert-뷰틸포스핀, 2-(다이-tert-뷰틸포스피노)바이페닐, 2-(다이사이클로헥실포스피노)바이페닐, 트라이페닐포스핀, 트리스-(2-퓨릴)포스핀 등을 가할 수 있다.
사용할 수 있는 용매로서는, 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화탄화수소류(예, 사이클로헥세인, 헥세인 등), 에터류(예, 테트라하이드로퓨란, 다이에틸에터, 다이옥세인, 다이메톡시에테인 등), N,N-다이메틸폼아마이드 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 -10 내지 180℃, 경우에 따라서는 마이크로웨이브 조사화(照射化), 바람직하게는 20 내지 120℃이다. 반응 시간은 화합물에 따라 다르지만 10분 내지 80시간 반응시키면 좋다.
수득된 원하는 화합물 (Ib)는 필요하다면 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
[경로 5]
Figure 112009066584530-PCT00034
[반응식 중의 기호는 상기와 같다.]
즉, 화학식 (Ⅹ)으로 표시되는 본 발명 화합물은 화합물 (IX)를 산화제 존재 하, 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다.
사용할 수 있는 산화제로서는, 예컨대 이산화망간, 2-아이오드옥시벤조산 등을 들 수 있고, 화합물 (IX)에 대하여 1당량 또는 그 이상, 바람직하게는 1 내지 1.5당량 사용할 수 있다.
사용할 수 있는 용매로서는, 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화 탄화수소류(예, 사이클로헥세인, 헥세인 등), 할로젠화 탄화수소류(예, 다이클로로메테인, 1,2-다이클로로에탄 등), 에터류(예, 테트라하이드로퓨란, 다이옥세인 등), 케톤류(예, 아세톤, 메틸에틸케톤 등), 나이트릴류(예, 아세토나이트릴 등) 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 -10 내지 150℃, 바람직하게는 20 내지 100℃이다. 반응 시간은 화합물에 따라 다르지만 10분 내지 80시간 반응시키면 좋다.
화합물 (IX)는 조제물(粗製物)로서, 또는 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제하여 다음 공정에서 사용할 수 있다.
[경로 5(계속)]
Figure 112009066584530-PCT00035
[상기 식에서, t는 0 내지 3의 정수이고, X1 및 X2는 각각 독립적으로 NR8, O 또는 S이고, R8은 수소 또는 저급 알킬이며, 그 밖의 기호는 상기와 같다]
즉, 화학식 (Ic)로 표시되는 본 발명의 화합물은 화합물 (Ⅹ) 및 화합물 (XI)을 산 존재 하, 또는 비존재 하, 무용매 또는 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다.
본 반응에 있어서, 화합물 (XI)은 화합물 (Ⅹ)에 대하여 1당량 또는 그 이상, 바람직하게는 1 내지 3당량 사용할 수 있다.
사용할 수 있는 산으로서는 파라톨루엔 설폰산, 황산, 파라톨루엔 설폰산피리디늄 염 등을 들 수 있다.
사용할 수 있는 용매로서는, 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화 탄화수소류(예, 사이클로헥세인, 헥세인 등) 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 -10 내지 170℃, 바람직하게는 20 내지 150℃이다. 반응 시간은 화합물에 따라 다르지만 10분 내지 80시간 반응시키면 좋다.
수득된 원하는 화합물 (Ic)는 필요하다면 통상적 방법(예, 컬럼크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
[경로 6]
Figure 112009066584530-PCT00036
[반응식 중의 기호는 상기와 같다]
즉, 화학식 (Id)로 표시되는 본 발명의 화합물은 화합물 (Ⅹ)과 화합물 (XⅡ) 또는 그 염을 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다. 화합물 (XⅡ) 및 그 염은 화합물 (Ⅹ)에 대하여 1 내지 4당량, 바람직하게는 1 내지 2.5당량 사용한다.
화합물 (XⅡ)의 염으로서는, 예컨대 염산염, 황산염 등의 광산염 등을 들 수 있다. 상기 염을 사용하는 경우는 염기로 중화하여 반응시킨다.
사용할 수 있는 염기로서는, 예컨대 아세트산나트륨, 아민류(피리딘 등) 등을 들 수 있고, 그 사용량은 화합물 (XI)의 염에 대하여 1 내지 3당량, 바람직하게는 1 내지 2당량이다.
사용할 수 있는 용매로서는, 예컨대 탄화수소류(예, 벤젠, 톨루엔, 자일렌 등), 할로젠화 탄화수소류(예, 클로로폼, 1,2-다이클로로에탄 등), 에터류(예, 테트라하이드로퓨란, 다이옥세인 등), 알코올류(예, 메탄올, 에탄올, n-프로판올, 아이소프로판올 등), 물 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 0 내지 150℃, 바람직하게는 20 내지 120℃이다.
반응 시간은 보통 10분 내지 24시간 정도이다.
수득된 원하는 화합물 (Id)는 필요하다면 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
[경로 7]
Figure 112009066584530-PCT00037
[상기 식에서, Hal은 할로젠이고, R9는 하이드록시의 보호기이며, 그 밖의 기호는 상기와 같다]
즉, 화학식 (Ie)로 표시되는 본 발명의 화합물은 화합물 (Ia)와 화합물 (XⅢ)을 염기 존재 하, 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다. 화합물 (XⅡ)는 화합물 (Ia)에 대하여 1 내지 4당량, 바람직하게는 1 내지 2.5당량 사용한다.
사용할 수 있는 염기로서는, 예컨대 아민류(트라이에틸아민, 피리딘 등) 등을 들 수 있고, 그 사용량은 화합물 (Ia)에 대하여 1 내지 3당량, 바람직하게는 1 내지 2당량이다.
사용할 수 있는 용매로서는, 예컨대 탄화수소류(예, 벤젠, 톨루엔, 자일렌 등), 할로젠화 탄화수소류(예, 클로로폼, 1,2-다이클로로에탄 등), 에터류(예, 테트라하이드로퓨란, 다이옥세인 등), N,N-다이메틸폼아마이드, 다이메틸설폭사이드 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 -20 내지 150℃, 바람직하게는 0 내지 20℃이다.
반응 시간은 보통 10분 내지 24시간 정도이다.
수득된 원하는 화합물 (Ie)는 필요하다면 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
[경로 8]
Figure 112009066584530-PCT00038
[반응식 중의 기호는 상기와 같다]
즉, 화학식 (If) 또는 화학식 (Ig)로 표시되는 본 발명의 화합물은 화합물 (Ia)와 아민류 또는 그 염을 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다. 아민류 및 그 염은 화합물 (Ia)에 대하여 1 내지 4당량, 바람직하게는 1 내지 2.5당량 사용한다.
하이드록실아민의 염으로서는, 예컨대 염산염, 황산염 등의 광산염 등을 들 수 있다. 상기 염을 사용하는 경우는 염기로 중화하여 반응시킨다.
사용할 수 있는 염기로서는, 예컨대 아세트산나트륨, 아민류(피리딘 등) 등을 들 수 있고, 그 사용량은 아민류의 염에 대하여 1 내지 3당량, 바람직하게는 1 내지 2당량이다.
사용할 수 있는 용매로서는, 예컨대 탄화수소류(예, 벤젠, 톨루엔, 자일렌 등), 할로젠화 탄화수소류(예, 클로로폼, 1,2-다이클로로에탄 등), 에터류(예, 테트라하이드로퓨란, 다이옥세인 등), 알코올류(예, 메탄올, 에탄올, n-프로판올, 아이소프로판올 등), 물 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 0 내지 150℃, 바람직하게는 20 내지 120℃이다.
반응 시간은 보통 15분 내지 24시간 정도이다.
수득된 원하는 화합물 (If) 또는 화합물 (Ig)는 필요하다면 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
[경로 9]
Figure 112009066584530-PCT00039
[반응식 중의 기호는 상기와 같다]
즉, 화학식 (Ih)로 표시되는 본 발명의 화합물은 화합물 (Ia)와 화합물 (XⅣ)를 적당한 용매 중에서 반응시키는 것에 의해 제조할 수 있다. 화합물 (XⅣ)는 화합물 (Ia)에 대하여 1 내지 4당량, 바람직하게는 1 내지 2.5당량 사용한다.
사용할 수 있는 용매로서는, 예컨대 아세트산, 탄화수소류(예, 벤젠, 톨루엔, 자일렌 등), 에터류(예, 테트라하이드로퓨란, 다이옥세인 등), 알코올류(예, 메탄올, 에탄올, n-프로판올, 아이소프로판올 등) 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 0 내지 150℃, 바람직하게는 50 내지 130℃이다.
반응 시간은 보통 10분 내지 24시간 정도이다.
수득된 원하는 화합물 (Ih)는 필요하다면 통상적 방법(예, 컬럼 크로마토그래피, 재결정 등)에 의해 정제할 수 있다.
본 발명의 화합물은 제약적으로 허용할 수 있는 산 또는 염기와의 염, 예컨대 염산, 황산, 질산, 인산, 불화수소산, 브롬화수소산 등의 무기산과의 염, 포름산, 아세트산, 옥살산, 석신산, 말레산, 타르타르산, 락트산, 시트르산, 푸마르산 등의 유기산과의 염, 암모늄, 트라이메틸암모늄, 트라이에틸암모늄 등의 유기 염기의 염, 나트륨, 칼륨 등의 알칼리 금속과의 염, 칼슘, 마그네슘 등의 알칼리 토금속과의 염을 형성할 수 있다.
또한, 본 발명의 화합물 또는 상기의 제약적으로 허용할 수 있는 염은 그 용매화물(바람직하게는 수화물)의 용매화물로 하는 것도 가능하다. 용매화물로서는 유기 용매 및/또는 물과의 용매화물을 들 수 있다. 용매화물을 형성할 때는 임의의 수의 용매 분자와 배위하고 있어도 좋다.
본 발명의 화합물 1은 특정한 이성질체로 한정되는 것이 아니라, 모든 가능한 이성질체나 라세미체를 포함하는 것이다. 예컨대, 하기와 같이 호변 이성질체(토토머; tautomer)를 함유한다.
Figure 112009066584530-PCT00040
본 발명의 화합물은, 특정한 입체 배치를 갖는 단리(單離)된 거울상체(거울상 이성질체; enantiomer) 또는 그들 거울상체 혼합물의 어느 것이라도 좋다. 예컨대, 본 발명의 화합물은 피롤리디논 고리의 5번 위치에서 특정한 입체 배치를 갖는 단리된 거울상체 또는 그와 같은 거울상체의 혼합물로 수득된다. 특정한 입체 배치를 갖는 거울상체는 예컨대 결정화, 효소 반응, 크로마토그래피 등의 당 분야에서 관용 기술을 이용하여 당업자가 용이하게 단리할 수 있다.
상기 화학식 1로 표시되는 본 발명의 화합물은 P2X3 및/또는 P2X2/3 수용체에 대한 길항 작용을 가져, P2X3 및/또는 P2X2/3가 관여하는 질환의 치료제로서 유용하다. P2X3 및/또는 P2X2/3 수용체는 동통 및 비뇨기계 질환에 관여한다고 생각되고 있고[Nature 407, 26, 1011-1015(2000), Nature, Vol.407, No.26, 1015-1017(2000), 비특허문헌 1, 비특허문헌 2 등], 예컨대 관절 류마티즘에 따른 통증, 변형성 관절증에 따른 통증, 두통, 편두통, 구강 안면통, 치통, 설(舌) 통증, 턱관절증에 따른 통증, 삼차 신경통, 견(肩)통, 추간판 헤르니아에 따른 통증, 변형성경추증에 따른 통증, 척주관 협착증에 따른 통증, 흉곽출구 증후군에 따른 통증, 외상성 상완 신경총 손상 증후군에 따른 통증, 견수(肩手) 증후군, 경추부 염좌에 따른 통증, 흉통, 복통, 산통(疝痛), 담석증에 따른 통증, 췌장염에 따른 통증, 요로 결석증, 과민성장 증후군에 따른 통증, 요통, 좌골신경통, 골절에 따른 통증, 골다공증에 따른 통증, 관절통, 통풍에 따른 통증, 마미증후군에 따른 통증, 강직성 척추염에 따른 통증, 근육통, 통증성 경련, 근근막통 증후군, 섬유근통 증후군, 폐색성 동맥 경화증에 따른 통증, 버거씨병(Buerger's disease)에 따른 통증, 레이노 현상(Raynaud's phenomenon)에 따른 통증, 대상포진에 따른 통증, 작열통(causalgic pain), 포착성 신경병증(entrapment neuropathy)에 따른 통증, 수근관 증후군에 따른 통증, 당뇨병에 따른 통증, 길랭-바레 증후군에 따른 통증, 한센병에 따른 통증, 약품 요법에 따른 통증, 방사선 요법에 따른 통증, 척수 손상에 따른 통증, 척수 공동증에 따른 통증, 뇌졸중에 따른 통증, 시상통, 구심로 차단통(deafferentation pain), 교감신경 의존성 동통, ABC 증후군, 다발성 경화증, 피부 질환에 따른 통증, 암성 동통, 수술후 통증, 외상에 따른 통증, 괴정(壞疽)에 따른 통증, 신체형 장애(somatoform disorder)에 따른 통증, 신체화 장애(somatization disorder)에 따른 통증, 우울장애에 따른 통증, 파킨슨병에 따른 통증, 슬관절통, 관절염에 따른 통증, 생리통, 중간통, 분만통(labor pain) 등의 신경장애성 동통, 염증성 동통, 침해 수용성 동통, 심인성 동통, 및 과민성 방광, 요실금, 빈뇨, 요절박(urinary urgency), 방광 위축, 전립선 비대, 전립선 염, 전립선 통, 과반사성 방광(detrusor hyperreflexia), 배뇨 장애, 신경성 빈뇨, 만성 전립선 염, 만성 방광염 등의 치료, 증상의 완화 또는 예방에 유효하다.
본 발명의 화합물은 ATP 수용체, 특별히 P2X3 수용체에 대하여 친화성이 높고, 서브 타입 선택성 및 다른 수용체에 대한 선택성이 높기 때문에 부작용(예컨대 운동 기능에의 영향 등)이 경감된 의약이 된다. 또한, 본 발명의 화합물은 안정성이 높고, 경구 흡수성이 높고, 양호한 생체 이용률(bioavailability)을 나타내고, 클리어런스(clearance)가 낮고, 반감기가 길며, 약효 지속성이 높고/높거나 간효소 저해 활성이 낮은 등의 이점도 갖는다.
또 다른 태양에 있어서, 본 발명은 유효량의 본 발명 화합물과 제약적으로 허용 가능한 담체를 조합하여 함유하는 의약 조성물을 제공한다.
본 발명의 화합물을 의약으로서 이용하는 경우, 예컨대 부형제, 결합제, 붕괴제, 활택제(滑澤劑), 착색제, 교미제(矯味劑), 교취제(矯臭劑), 계면활성제 등, 당 분야에서 주지된 제약적으로 허용할 수 있는 담체를 이용하여 통상적 방법에 따라서 의약 조성물을 제조할 수 있다.
본 발명에 따른 의약 조성물을 인간을 포함하는 포유동물의 치료에 투여하는 경우, 투여 단위 제형(劑形)은 치료 목적과 투여 경로에 따라 적절히 선택할 수 있다. 구체적으로는 정제, 피복정제, 가루약, 과립제, 캡슐제, 액제, 환제, 현탁제, 유제 등의 경구제, 및 주사제, 좌제, 연고, 부착제, 에어로졸제 등의 비경구제를 들 수 있다. 이들 투여 단위 제형은 당 분야에서 주지된 방법에 의해 제제화 된다.
상기 제제 중에 함유되는 본 발명 화합물의 양은 제형, 투여 경로, 투여 계획 등에 의해서 적절히 변경될 수 있다.
본 발명에 따른 의약 조성물의 투여 방법은 제제의 제형, 환자의 연령, 성별, 체중, 증상의 정도 및 그 밖의 조건 등에 따라 적절히 결정되며, 경구, 피하, 경피, 직장, 비강 내, 구강 등의 여러 가지의 경로로부터 선택될 수 있다.
본 발명의 의약 조성물에 함유되는 본 발명 화합물의 용량은 선택한 투여 경로, 환자의 연령, 성별, 체중, 질환의 상태, 투여되는 본 발명화합물의 종류, 그 밖의 조건 등에 따라 적절히 선택되지만, 성인에 경구 투여하는 경우, 보통 0.05 내지 1000mg/kg/일이며, 바람직하게는 O.1 내지 1Omg/kg/일의 범위 내이다. 비경구 투여의 경우에는 투여 경로에 따라 크게 다르지만, 보통 0.005 내지 100mg/kg/일이며, 바람직하게는 0.01 내지 1mg/kg/일의 범위 내이다. 이들 본 발명의 의약 조성물은 하루에 한 번 또는 복수 회로 나누어 투여할 수 있다.
본 발명 화합물의 바람직한 태양은 이하의 식 (a) 내지 (f)에 있어서 이하의 기를 갖는 것이다.
Figure 112009066584530-PCT00041
Figure 112009066584530-PCT00042
Figure 112009066584530-PCT00043
Figure 112009066584530-PCT00044
Figure 112009066584530-PCT00045
(상기 표 중, Ac은 아세틸, Me는 메틸, Et는 에틸, Pr는 프로필, iPr은 아이소프로필, nBu는 n-뷰틸, tBu는 t-뷰틸, cBu는 사이클로뷰틸, cPent는 사이클로펜틸, cHex는 사이클로헥실, Ph는 페닐을 나타낸다)
Z1, R1, R2 및 R3의 조합 (Z1,R1,R2,R3)이 이하인 화합물.
(Z1,R1,R2,R3)=
(ZA,R1A,R2A,R3A), (ZA,R1A,R2A,R3B), (ZA,R1A,R2A,R3C), (ZA,R1A,R2A,R3D), (ZA,R1A,R2A,R3E), (ZA,R1A,R2A,R3F), (ZA,R1A,R2A,R3G), (ZA,R1A,R2A,R3H), (ZA,R1A,R2A,R3I), (ZA,R1A,R2A,R3J), (ZA,R1A,R2A,R3K), (ZA,R1A,R2A,R3L), (ZA,R1A,R2A,R3M), (ZA,R1A,R2A,R3N), (ZA,R1A,R2A,R3O), (ZA,R1A,R2A,R3P), (ZA,R1A,R2A,R3Q), (ZA,R1A,R2A,R3R), (ZA,R1A,R2B,R3A), (ZA,R1A,R2B,R3B), (ZA,R1A,R2B,R3C), (ZA,R1A,R2B,R3D), (ZA,R1A,R2B,R3E), (ZA,R1A,R2B,R3F), (ZA,R1A,R2B,R3G), (ZA,R1A,R2B,R3H), (ZA,R1A,R2B,R3I), (ZA,R1A,R2B,R3J), (ZA,R1A,R2B,R3K), (ZA,R1A,R2B,R3L), (ZA,R1A,R2B,R3M), (ZA,R1A,R2B,R3N), (ZA,R1A,R2B,R3O), (ZA,R1A,R2B,R3P), (ZA,R1A,R2B,R3Q), (ZA,R1A,R2B,R3R), (ZA,R1A,R2C,R3A), (ZA,R1A,R2C,R3B), (ZA,R1A,R2C,R3C), (ZA,R1A,R2C,R3D), (ZA,R1A,R2C,R3E), (ZA,R1A,R2C,R3F), (ZA,R1A,R2C,R3G), (ZA,R1A,R2C,R3H), (ZA,R1A,R2C,R3I), (ZA,R1A,R2C,R3J), (ZA,R1A,R2C,R3K), (ZA,R1A,R2C,R3L), (ZA,R1A,R2C,R3M), (ZA,R1A,R2C,R3N), (ZA,R1A,R2C,R3O), (ZA,R1A,R2C,R3P), (ZA,R1A,R2C,R3Q), (ZA,R1A,R2C,R3R), (ZA,R1A,R2D,R3A), (ZA,R1A,R2D,R3B), (ZA,R1A,R2D,R3C), (ZA,R1A,R2D,R3D), (ZA,R1A,R2D,R3E), (ZA,R1A,R2D,R3F), (ZA,R1A,R2D,R3G), (ZA,R1A,R2D,R3H), (ZA,R1A,R2D,R3I), (ZA,R1A,R2D,R3J), (ZA,R1A,R2D,R3K), (ZA,R1A,R2D,R3L), (ZA,R1A,R2D,R3M), (ZA,R1A,R2D,R3N), (ZA,R1A,R2D,R3O), (ZA,R1A,R2D,R3P), (ZA,R1A,R2D,R3Q), (ZA,R1A,R2D,R3R), (ZA,R1A,R2E,R3A), (ZA,R1A,R2E,R3B), (ZA,R1A,R2E,R3C), (ZA,R1A,R2E,R3D), (ZA,R1A,R2E,R3E), (ZA,R1A,R2E,R3F), (ZA,R1A,R2E,R3G), (ZA,R1A,R2E,R3H), (ZA,R1A,R2E,R3I), (ZA,R1A,R2E,R3J), (ZA,R1A,R2E,R3K), (ZA,R1A,R2E,R3L), (ZA,R1A,R2E,R3M), (ZA,R1A,R2E,R3N), (ZA,R1A,R2E,R3O), (ZA,R1A,R2E,R3P), (ZA,R1A,R2E,R3Q), (ZA,R1A,R2E,R3R), (ZA,R1A,R2F,R3A), (ZA,R1A,R2F,R3B), (ZA,R1A,R2F,R3C), (ZA,R1A,R2F,R3D), (ZA,R1A,R2F,R3E), (ZA,R1A,R2F,R3F), (ZA,R1A,R2F,R3G), (ZA,R1A,R2F,R3H), (ZA,R1A,R2F,R3I), (ZA,R1A,R2F,R3J), (ZA,R1A,R2F,R3K), (ZA,R1A,R2F,R3L), (ZA,R1A,R2F,R3M), (ZA,R1A,R2F,R3N), (ZA,R1A,R2F,R3O), (ZA,R1A,R2F,R3P), (ZA,R1A,R2F,R3Q), (ZA,R1A,R2F,R3R), (ZA,R1A,R2G,R3A), (ZA,R1A,R2G,R3B), (ZA,R1A,R2G,R3C), (ZA,R1A,R2G,R3D), (ZA,R1A,R2G,R3E), (ZA,R1A,R2G,R3F), (ZA,R1A,R2G,R3G), (ZA,R1A,R2G,R3H), (ZA,R1A,R2G,R3I), (ZA,R1A,R2G,R3J), (ZA,R1A,R2G,R3K), (ZA,R1A,R2G,R3L), (ZA,R1A,R2G,R3M), (ZA,R1A,R2G,R3N), (ZA,R1A,R2G,R3O), (ZA,R1A,R2G,R3P), (ZA,R1A,R2G,R3Q), (ZA,R1A,R2G,R3R), (ZA,R1A,R2H,R3A), (ZA,R1A,R2H,R3B), (ZA,R1A,R2H,R3C), (ZA,R1A,R2H,R3D), (ZA,R1A,R2H,R3E), (ZA,R1A,R2H,R3F), (ZA,R1A,R2H,R3G), (ZA,R1A,R2H,R3H), (ZA,R1A,R2H,R3I), (ZA,R1A,R2H,R3J), (ZA,R1A,R2H,R3K), (ZA,R1A,R2H,R3L), (ZA,R1A,R2H,R3M), (ZA,R1A,R2H,R3N), (ZA,R1A,R2H,R3O), (ZA,R1A,R2H,R3P), (ZA,R1A,R2H,R3Q), (ZA,R1A,R2H,R3R), (ZA,R1A,R2I,R3A), (ZA,R1A,R2I,R3B), (ZA,R1A,R2I,R3C), (ZA,R1A,R2I,R3D), (ZA,R1A,R2I,R3E), (ZA,R1A,R2I,R3F), (ZA,R1A,R2I,R3G), (ZA,R1A,R2I,R3H), (ZA,R1A,R2I,R3I), (ZA,R1A,R2I,R3J), (ZA,R1A,R2I,R3K), (ZA,R1A,R2I,R3L), (ZA,R1A,R2I,R3M), (ZA,R1A,R2I,R3N), (ZA,R1A,R2I,R3O), (ZA,R1A,R2I,R3P), (ZA,R1A,R2I,R3Q), (ZA,R1A,R2I,R3R), (ZA,R1A,R2J,R3A), (ZA,R1A,R2J,R3B), (ZA,R1A,R2J,R3C), (ZA,R1A,R2J,R3D), (ZA,R1A,R2J,R3E), (ZA,R1A,R2J,R3F), (ZA,R1A,R2J,R3G), (ZA,R1A,R2J,R3H), (ZA,R1A,R2J,R3I), (ZA,R1A,R2J,R3J), (ZA,R1A,R2J,R3K), (ZA,R1A,R2J,R3L), (ZA,R1A,R2J,R3M), (ZA,R1A,R2J,R3N), (ZA,R1A,R2J,R3O), (ZA,R1A,R2J,R3P), (ZA,R1A,R2J,R3Q), (ZA,R1A,R2J,R3R), (ZA,R1A,R2K,R3A), (ZA,R1A,R2K,R3B), (ZA,R1A,R2K,R3C), (ZA,R1A,R2K,R3D), (ZA,R1A,R2K,R3E), (ZA,R1A,R2K,R3F), (ZA,R1A,R2K,R3G), (ZA,R1A,R2K,R3H), (ZA,R1A,R2K,R3I), (ZA,R1A,R2K,R3J), (ZA,R1A,R2K,R3K), (ZA,R1A,R2K,R3L), (ZA,R1A,R2K,R3M), (ZA,R1A,R2K,R3N), (ZA,R1A,R2K,R3O), (ZA,R1A,R2K,R3P), (ZA,R1A,R2K,R3Q), (ZA,R1A,R2K,R3R), (ZA,R1A,R2L,R3A), (ZA,R1A,R2L,R3B), (ZA,R1A,R2L,R3C), (ZA,R1A,R2L,R3D), (ZA,R1A,R2L,R3E), (ZA,R1A,R2L,R3F), (ZA,R1A,R2L,R3G), (ZA,R1A,R2L,R3H), (ZA,R1A,R2L,R3I), (ZA,R1A,R2L,R3J), (ZA,R1A,R2L,R3K), (ZA,R1A,R2L,R3L), (ZA,R1A,R2L,R3M), (ZA,R1A,R2L,R3N), (ZA,R1A,R2L,R3O), (ZA,R1A,R2L,R3P), (ZA,R1A,R2L,R3Q), (ZA,R1A,R2L,R3R), (ZA,R1A,R2M,R3A), (ZA,R1A,R2M,R3B), (ZA,R1A,R2M,R3C), (ZA,R1A,R2M,R3D), (ZA,R1A,R2M,R3E), (ZA,R1A,R2M,R3F), (ZA,R1A,R2M,R3G), (ZA,R1A,R2M,R3H), (ZA,R1A,R2M,R3I), (ZA,R1A,R2M,R3J), (ZA,R1A,R2M,R3K), (ZA,R1A,R2M,R3L), (ZA,R1A,R2M,R3M), (ZA,R1A,R2M,R3N), (ZA,R1A,R2M,R3O), (ZA,R1A,R2M,R3P), (ZA,R1A,R2M,R3Q), (ZA,R1A,R2M,R3R), (ZA,R1A,R2N,R3A), (ZA,R1A,R2N,R3B), (ZA,R1A,R2N,R3C), (ZA,R1A,R2N,R3D), (ZA,R1A,R2N,R3E), (ZA,R1A,R2N,R3F), (ZA,R1A,R2N,R3G), (ZA,R1A,R2N,R3H), (ZA,R1A,R2N,R3I), (ZA,R1A,R2N,R3J), (ZA,R1A,R2N,R3K), (ZA,R1A,R2N,R3L), (ZA,R1A,R2N,R3M), (ZA,R1A,R2N,R3N), (ZA,R1A,R2N,R3O), (ZA,R1A,R2N,R3P), (ZA,R1A,R2N,R3Q), (ZA,R1A,R2N,R3R), (ZA,R1B,R2A,R3A), (ZA,R1B,R2A,R3B), (ZA,R1B,R2A,R3C), (ZA,R1B,R2A,R3D), (ZA,R1B,R2A,R3E), (ZA,R1B,R2A,R3F), (ZA,R1B,R2A,R3G), (ZA,R1B,R2A,R3H), (ZA,R1B,R2A,R3I), (ZA,R1B,R2A,R3J), (ZA,R1B,R2A,R3K), (ZA,R1B,R2A,R3L), (ZA,R1B,R2A,R3M), (ZA,R1B,R2A,R3N), (ZA,R1B,R2A,R3O), (ZA,R1B,R2A,R3P), (ZA,R1B,R2A,R3Q), (ZA,R1B,R2A,R3R), (ZA,R1B,R2B,R3A), (ZA,R1B,R2B,R3B), (ZA,R1B,R2B,R3C), (ZA,R1B,R2B,R3D), (ZA,R1B,R2B,R3E), (ZA,R1B,R2B,R3F), (ZA,R1B,R2B,R3G), (ZA,R1B,R2B,R3H), (ZA,R1B,R2B,R3I), (ZA,R1B,R2B,R3J), (ZA,R1B,R2B,R3K), (ZA,R1B,R2B,R3L), (ZA,R1B,R2B,R3M), (ZA,R1B,R2B,R3N), (ZA,R1B,R2B,R3O), (ZA,R1B,R2B,R3P), (ZA,R1B,R2B,R3Q), (ZA,R1B,R2B,R3R), (ZA,R1B,R2C,R3A), (ZA,R1B,R2C,R3B), (ZA,R1B,R2C,R3C), (ZA,R1B,R2C,R3D), (ZA,R1B,R2C,R3E), (ZA,R1B,R2C,R3F), (ZA,R1B,R2C,R3G), (ZA,R1B,R2C,R3H), (ZA,R1B,R2C,R3I), (ZA,R1B,R2C,R3J), (ZA,R1B,R2C,R3K), (ZA,R1B,R2C,R3L), (ZA,R1B,R2C,R3M), (ZA,R1B,R2C,R3N), (ZA,R1B,R2C,R3O), (ZA,R1B,R2C,R3P), (ZA,R1B,R2C,R3Q), (ZA,R1B,R2C,R3R), (ZA,R1B,R2D,R3A), (ZA,R1B,R2D,R3B), (ZA,R1B,R2D,R3C), (ZA,R1B,R2D,R3D), (ZA,R1B,R2D,R3E), (ZA,R1B,R2D,R3F), (ZA,R1B,R2D,R3G), (ZA,R1B,R2D,R3H), (ZA,R1B,R2D,R3I), (ZA,R1B,R2D,R3J), (ZA,R1B,R2D,R3K), (ZA,R1B,R2D,R3L), (ZA,R1B,R2D,R3M), (ZA,R1B,R2D,R3N), (ZA,R1B,R2D,R3O), (ZA,R1B,R2D,R3P), (ZA,R1B,R2D,R3Q), (ZA,R1B,R2D,R3R), (ZA,R1B,R2E,R3A), (ZA,R1B,R2E,R3B), (ZA,R1B,R2E,R3C), (ZA,R1B,R2E,R3D), (ZA,R1B,R2E,R3E), (ZA,R1B,R2E,R3F), (ZA,R1B,R2E,R3G), (ZA,R1B,R2E,R3H), (ZA,R1B,R2E,R3I), (ZA,R1B,R2E,R3J), (ZA,R1B,R2E,R3K), (ZA,R1B,R2E,R3L), (ZA,R1B,R2E,R3M), (ZA,R1B,R2E,R3N), (ZA,R1B,R2E,R3O), (ZA,R1B,R2E,R3P), (ZA,R1B,R2E,R3Q), (ZA,R1B,R2E,R3R), (ZA,R1B,R2F,R3A), (ZA,R1B,R2F,R3B), (ZA,R1B,R2F,R3C), (ZA,R1B,R2F,R3D), (ZA,R1B,R2F,R3E), (ZA,R1B,R2F,R3F), (ZA,R1B,R2F,R3G), (ZA,R1B,R2F,R3H), (ZA,R1B,R2F,R3I), (ZA,R1B,R2F,R3J), (ZA,R1B,R2F,R3K), (ZA,R1B,R2F,R3L), (ZA,R1B,R2F,R3M), (ZA,R1B,R2F,R3N), (ZA,R1B,R2F,R3O), (ZA,R1B,R2F,R3P), (ZA,R1B,R2F,R3Q), (ZA,R1B,R2F,R3R), (ZA,R1B,R2G,R3A), (ZA,R1B,R2G,R3B), (ZA,R1B,R2G,R3C), (ZA,R1B,R2G,R3D), (ZA,R1B,R2G,R3E), (ZA,R1B,R2G,R3F), (ZA,R1B,R2G,R3G), (ZA,R1B,R2G,R3H), (ZA,R1B,R2G,R3I), (ZA,R1B,R2G,R3J), (ZA,R1B,R2G,R3K), (ZA,R1B,R2G,R3L), (ZA,R1B,R2G,R3M), (ZA,R1B,R2G,R3N), (ZA,R1B,R2G,R3O), (ZA,R1B,R2G,R3P), (ZA,R1B,R2G,R3Q), (ZA,R1B,R2G,R3R), (ZA,R1B,R2H,R3A), (ZA,R1B,R2H,R3B), (ZA,R1B,R2H,R3C), (ZA,R1B,R2H,R3D), (ZA,R1B,R2H,R3E), (ZA,R1B,R2H,R3F), (ZA,R1B,R2H,R3G), (ZA,R1B,R2H,R3H), (ZA,R1B,R2H,R3I), (ZA,R1B,R2H,R3J), (ZA,R1B,R2H,R3K), (ZA,R1B,R2H,R3L), (ZA,R1B,R2H,R3M), (ZA,R1B,R2H,R3N), (ZA,R1B,R2H,R3O), (ZA,R1B,R2H,R3P), (ZA,R1B,R2H,R3Q), (ZA,R1B,R2H,R3R), (ZA,R1B,R2I,R3A), (ZA,R1B,R2I,R3B), (ZA,R1B,R2I,R3C), (ZA,R1B,R2I,R3D), (ZA,R1B,R2I,R3E), (ZA,R1B,R2I,R3F), (ZA,R1B,R2I,R3G), (ZA,R1B,R2I,R3H), (ZA,R1B,R2I,R3I), (ZA,R1B,R2I,R3J), (ZA,R1B,R2I,R3K), (ZA,R1B,R2I,R3L), (ZA,R1B,R2I,R3M), (ZA,R1B,R2I,R3N), (ZA,R1B,R2I,R3O), (ZA,R1B,R2I,R3P), (ZA,R1B,R2I,R3Q), (ZA,R1B,R2I,R3R), (ZA,R1B,R2J,R3A), (ZA,R1B,R2J,R3B), (ZA,R1B,R2J,R3C), (ZA,R1B,R2J,R3D), (ZA,R1B,R2J,R3E), (ZA,R1B,R2J,R3F), (ZA,R1B,R2J,R3G), (ZA,R1B,R2J,R3H), (ZA,R1B,R2J,R3I), (ZA,R1B,R2J,R3J), (ZA,R1B,R2J,R3K), (ZA,R1B,R2J,R3L), (ZA,R1B,R2J,R3M), (ZA,R1B,R2J,R3N), (ZA,R1B,R2J,R3O), (ZA,R1B,R2J,R3P), (ZA,R1B,R2J,R3Q), (ZA,R1B,R2J,R3R), (ZA,R1B,R2K,R3A), (ZA,R1B,R2K,R3B), (ZA,R1B,R2K,R3C), (ZA,R1B,R2K,R3D), (ZA,R1B,R2K,R3E), (ZA,R1B,R2K,R3F), (ZA,R1B,R2K,R3G), (ZA,R1B,R2K,R3H), (ZA,R1B,R2K,R3I), (ZA,R1B,R2K,R3J), (ZA,R1B,R2K,R3K), (ZA,R1B,R2K,R3L), (ZA,R1B,R2K,R3M), (ZA,R1B,R2K,R3N), (ZA,R1B,R2K,R3O), (ZA,R1B,R2K,R3P), (ZA,R1B,R2K,R3Q), (ZA,R1B,R2K,R3R), (ZA,R1B,R2L,R3A), (ZA,R1B,R2L,R3B), (ZA,R1B,R2L,R3C), (ZA,R1B,R2L,R3D), (ZA,R1B,R2L,R3E), (ZA,R1B,R2L,R3F), (ZA,R1B,R2L,R3G), (ZA,R1B,R2L,R3H), (ZA,R1B,R2L,R3I), (ZA,R1B,R2L,R3J), (ZA,R1B,R2L,R3K), (ZA,R1B,R2L,R3L), (ZA,R1B,R2L,R3M), (ZA,R1B,R2L,R3N), (ZA,R1B,R2L,R3O), (ZA,R1B,R2L,R3P), (ZA,R1B,R2L,R3Q), (ZA,R1B,R2L,R3R), (ZA,R1B,R2M,R3A), (ZA,R1B,R2M,R3B), (ZA,R1B,R2M,R3C), (ZA,R1B,R2M,R3D), (ZA,R1B,R2M,R3E), (ZA,R1B,R2M,R3F), (ZA,R1B,R2M,R3G), (ZA,R1B,R2M,R3H), (ZA,R1B,R2M,R3I), (ZA,R1B,R2M,R3J), (ZA,R1B,R2M,R3K), (ZA,R1B,R2M,R3L), (ZA,R1B,R2M,R3M), (ZA,R1B,R2M,R3N), (ZA,R1B,R2M,R3O), (ZA,R1B,R2M,R3P), (ZA,R1B,R2M,R3Q), (ZA,R1B,R2M,R3R), (ZA,R1B,R2N,R3A), (ZA,R1B,R2N,R3B), (ZA,R1B,R2N,R3C), (ZA,R1B,R2N,R3D), (ZA,R1B,R2N,R3E), (ZA,R1B,R2N,R3F), (ZA,R1B,R2N,R3G), (ZA,R1B,R2N,R3H), (ZA,R1B,R2N,R3I), 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(ZC,R1R,R2G,R3C), (ZC,R1R,R2G,R3D), (ZC,R1R,R2G,R3E), (ZC,R1R,R2G,R3F), (ZC,R1R,R2G,R3G), (ZC,R1R,R2G,R3H), (ZC,R1R,R2G,R3I), (ZC,R1R,R2G,R3J), (ZC,R1R,R2G,R3K), (ZC,R1R,R2G,R3L), (ZC,R1R,R2G,R3M), (ZC,R1R,R2G,R3N), (ZC,R1R,R2G,R3O), (ZC,R1R,R2G,R3P), (ZC,R1R,R2G,R3Q), (ZC,R1R,R2G,R3R), (ZC,R1R,R2H,R3A), (ZC,R1R,R2H,R3B), (ZC,R1R,R2H,R3C), (ZC,R1R,R2H,R3D), (ZC,R1R,R2H,R3E), (ZC,R1R,R2H,R3F), (ZC,R1R,R2H,R3G), (ZC,R1R,R2H,R3H), (ZC,R1R,R2H,R3I), (ZC,R1R,R2H,R3J), (ZC,R1R,R2H,R3K), (ZC,R1R,R2H,R3L), (ZC,R1R,R2H,R3M), (ZC,R1R,R2H,R3N), (ZC,R1R,R2H,R3O), (ZC,R1R,R2H,R3P), (ZC,R1R,R2H,R3Q), (ZC,R1R,R2H,R3R), (ZC,R1R,R2I,R3A), (ZC,R1R,R2I,R3B), (ZC,R1R,R2I,R3C), (ZC,R1R,R2I,R3D), (ZC,R1R,R2I,R3E), (ZC,R1R,R2I,R3F), (ZC,R1R,R2I,R3G), (ZC,R1R,R2I,R3H), (ZC,R1R,R2I,R3I), (ZC,R1R,R2I,R3J), (ZC,R1R,R2I,R3K), (ZC,R1R,R2I,R3L), (ZC,R1R,R2I,R3M), (ZC,R1R,R2I,R3N), (ZC,R1R,R2I,R3O), (ZC,R1R,R2I,R3P), (ZC,R1R,R2I,R3Q), (ZC,R1R,R2I,R3R), (ZC,R1R,R2J,R3A), (ZC,R1R,R2J,R3B), (ZC,R1R,R2J,R3C), (ZC,R1R,R2J,R3D), (ZC,R1R,R2J,R3E), (ZC,R1R,R2J,R3F), (ZC,R1R,R2J,R3G), (ZC,R1R,R2J,R3H), (ZC,R1R,R2J,R3I), (ZC,R1R,R2J,R3J), (ZC,R1R,R2J,R3K), (ZC,R1R,R2J,R3L), (ZC,R1R,R2J,R3M), (ZC,R1R,R2J,R3N), (ZC,R1R,R2J,R3O), (ZC,R1R,R2J,R3P), (ZC,R1R,R2J,R3Q), (ZC,R1R,R2J,R3R), (ZC,R1R,R2K,R3A), (ZC,R1R,R2K,R3B), (ZC,R1R,R2K,R3C), (ZC,R1R,R2K,R3D), (ZC,R1R,R2K,R3E), (ZC,R1R,R2K,R3F), (ZC,R1R,R2K,R3G), (ZC,R1R,R2K,R3H), (ZC,R1R,R2K,R3I), (ZC,R1R,R2K,R3J), (ZC,R1R,R2K,R3K), (ZC,R1R,R2K,R3L), (ZC,R1R,R2K,R3M), (ZC,R1R,R2K,R3N), (ZC,R1R,R2K,R3O), (ZC,R1R,R2K,R3P), (ZC,R1R,R2K,R3Q), (ZC,R1R,R2K,R3R), (ZC,R1R,R2L,R3A), (ZC,R1R,R2L,R3B), (ZC,R1R,R2L,R3C), (ZC,R1R,R2L,R3D), (ZC,R1R,R2L,R3E), (ZC,R1R,R2L,R3F), (ZC,R1R,R2L,R3G), (ZC,R1R,R2L,R3H), (ZC,R1R,R2L,R3I), (ZC,R1R,R2L,R3J), (ZC,R1R,R2L,R3K), (ZC,R1R,R2L,R3L), (ZC,R1R,R2L,R3M), (ZC,R1R,R2L,R3N), (ZC,R1R,R2L,R3O), (ZC,R1R,R2L,R3P), (ZC,R1R,R2L,R3Q), (ZC,R1R,R2L,R3R), (ZC,R1R,R2M,R3A), (ZC,R1R,R2M,R3B), (ZC,R1R,R2M,R3C), (ZC,R1R,R2M,R3D), (ZC,R1R,R2M,R3E), (ZC,R1R,R2M,R3F), (ZC,R1R,R2M,R3G), (ZC,R1R,R2M,R3H), (ZC,R1R,R2M,R3I), (ZC,R1R,R2M,R3J), (ZC,R1R,R2M,R3K), (ZC,R1R,R2M,R3L), (ZC,R1R,R2M,R3M), (ZC,R1R,R2M,R3N), (ZC,R1R,R2M,R3O), (ZC,R1R,R2M,R3P), (ZC,R1R,R2M,R3Q), (ZC,R1R,R2M,R3R), (ZC,R1R,R2N,R3A), (ZC,R1R,R2N,R3B), (ZC,R1R,R2N,R3C), (ZC,R1R,R2N,R3D), (ZC,R1R,R2N,R3E), (ZC,R1R,R2N,R3F), (ZC,R1R,R2N,R3G), (ZC,R1R,R2N,R3H), (ZC,R1R,R2N,R3I), (ZC,R1R,R2N,R3J), (ZC,R1R,R2N,R3K), (ZC,R1R,R2N,R3L), (ZC,R1R,R2N,R3M), (ZC,R1R,R2N,R3N), (ZC,R1R,R2N,R3O), (ZC,R1R,R2N,R3P), (ZC,R1R,R2N,R3Q), (ZC,R1R,R2N,R3R), (ZC,R1S,R2A,R3A), (ZC,R1S,R2A,R3B), (ZC,R1S,R2A,R3C), (ZC,R1S,R2A,R3D), (ZC,R1S,R2A,R3E), (ZC,R1S,R2A,R3F), (ZC,R1S,R2A,R3G), (ZC,R1S,R2A,R3H), (ZC,R1S,R2A,R3I), (ZC,R1S,R2A,R3J), (ZC,R1S,R2A,R3K), (ZC,R1S,R2A,R3L), (ZC,R1S,R2A,R3M), (ZC,R1S,R2A,R3N), (ZC,R1S,R2A,R3O), (ZC,R1S,R2A,R3P), (ZC,R1S,R2A,R3Q), (ZC,R1S,R2A,R3R), (ZC,R1S,R2B,R3A), (ZC,R1S,R2B,R3B), (ZC,R1S,R2B,R3C), (ZC,R1S,R2B,R3D), (ZC,R1S,R2B,R3E), (ZC,R1S,R2B,R3F), (ZC,R1S,R2B,R3G), (ZC,R1S,R2B,R3H), (ZC,R1S,R2B,R3I), (ZC,R1S,R2B,R3J), (ZC,R1S,R2B,R3K), (ZC,R1S,R2B,R3L), (ZC,R1S,R2B,R3M), (ZC,R1S,R2B,R3N), (ZC,R1S,R2B,R3O), (ZC,R1S,R2B,R3P), (ZC,R1S,R2B,R3Q), (ZC,R1S,R2B,R3R), (ZC,R1S,R2C,R3A), (ZC,R1S,R2C,R3B), (ZC,R1S,R2C,R3C), (ZC,R1S,R2C,R3D), (ZC,R1S,R2C,R3E), (ZC,R1S,R2C,R3F), (ZC,R1S,R2C,R3G), (ZC,R1S,R2C,R3H), (ZC,R1S,R2C,R3I), (ZC,R1S,R2C,R3J), (ZC,R1S,R2C,R3K), (ZC,R1S,R2C,R3L), (ZC,R1S,R2C,R3M), (ZC,R1S,R2C,R3N), (ZC,R1S,R2C,R3O), (ZC,R1S,R2C,R3P), (ZC,R1S,R2C,R3Q), (ZC,R1S,R2C,R3R), (ZC,R1S,R2D,R3A), (ZC,R1S,R2D,R3B), (ZC,R1S,R2D,R3C), (ZC,R1S,R2D,R3D), (ZC,R1S,R2D,R3E), (ZC,R1S,R2D,R3F), (ZC,R1S,R2D,R3G), (ZC,R1S,R2D,R3H), (ZC,R1S,R2D,R3I), (ZC,R1S,R2D,R3J), (ZC,R1S,R2D,R3K), (ZC,R1S,R2D,R3L), (ZC,R1S,R2D,R3M), (ZC,R1S,R2D,R3N), (ZC,R1S,R2D,R3O), (ZC,R1S,R2D,R3P), (ZC,R1S,R2D,R3Q), (ZC,R1S,R2D,R3R), (ZC,R1S,R2E,R3A), (ZC,R1S,R2E,R3B), (ZC,R1S,R2E,R3C), (ZC,R1S,R2E,R3D), (ZC,R1S,R2E,R3E), (ZC,R1S,R2E,R3F), (ZC,R1S,R2E,R3G), (ZC,R1S,R2E,R3H), (ZC,R1S,R2E,R3I), (ZC,R1S,R2E,R3J), (ZC,R1S,R2E,R3K), (ZC,R1S,R2E,R3L), (ZC,R1S,R2E,R3M), (ZC,R1S,R2E,R3N), (ZC,R1S,R2E,R3O), (ZC,R1S,R2E,R3P), (ZC,R1S,R2E,R3Q), (ZC,R1S,R2E,R3R), (ZC,R1S,R2F,R3A), (ZC,R1S,R2F,R3B), (ZC,R1S,R2F,R3C), (ZC,R1S,R2F,R3D), (ZC,R1S,R2F,R3E), (ZC,R1S,R2F,R3F), (ZC,R1S,R2F,R3G), (ZC,R1S,R2F,R3H), (ZC,R1S,R2F,R3I), (ZC,R1S,R2F,R3J), (ZC,R1S,R2F,R3K), (ZC,R1S,R2F,R3L), (ZC,R1S,R2F,R3M), (ZC,R1S,R2F,R3N), (ZC,R1S,R2F,R3O), (ZC,R1S,R2F,R3P), (ZC,R1S,R2F,R3Q), (ZC,R1S,R2F,R3R), (ZC,R1S,R2G,R3A), (ZC,R1S,R2G,R3B), (ZC,R1S,R2G,R3C), (ZC,R1S,R2G,R3D), (ZC,R1S,R2G,R3E), (ZC,R1S,R2G,R3F), (ZC,R1S,R2G,R3G), (ZC,R1S,R2G,R3H), (ZC,R1S,R2G,R3I), (ZC,R1S,R2G,R3J), (ZC,R1S,R2G,R3K), (ZC,R1S,R2G,R3L), (ZC,R1S,R2G,R3M), (ZC,R1S,R2G,R3N), (ZC,R1S,R2G,R3O), (ZC,R1S,R2G,R3P), (ZC,R1S,R2G,R3Q), (ZC,R1S,R2G,R3R), (ZC,R1S,R2H,R3A), (ZC,R1S,R2H,R3B), (ZC,R1S,R2H,R3C), (ZC,R1S,R2H,R3D), (ZC,R1S,R2H,R3E), (ZC,R1S,R2H,R3F), (ZC,R1S,R2H,R3G), (ZC,R1S,R2H,R3H), (ZC,R1S,R2H,R3I), (ZC,R1S,R2H,R3J), (ZC,R1S,R2H,R3K), (ZC,R1S,R2H,R3L), (ZC,R1S,R2H,R3M), (ZC,R1S,R2H,R3N), (ZC,R1S,R2H,R3O), (ZC,R1S,R2H,R3P), (ZC,R1S,R2H,R3Q), (ZC,R1S,R2H,R3R), (ZC,R1S,R2I,R3A), (ZC,R1S,R2I,R3B), (ZC,R1S,R2I,R3C), (ZC,R1S,R2I,R3D), (ZC,R1S,R2I,R3E), (ZC,R1S,R2I,R3F), (ZC,R1S,R2I,R3G), (ZC,R1S,R2I,R3H), (ZC,R1S,R2I,R3I), (ZC,R1S,R2I,R3J),
(ZC,R1S,R2I,R3K), (ZC,R1S,R2I,R3L), (ZC,R1S,R2I,R3M), (ZC,R1S,R2I,R3N), (ZC,R1S,R2I,R3O), (ZC,R1S,R2I,R3P), (ZC,R1S,R2I,R3Q), (ZC,R1S,R2I,R3R), (ZC,R1S,R2J,R3A), (ZC,R1S,R2J,R3B), (ZC,R1S,R2J,R3C), (ZC,R1S,R2J,R3D), (ZC,R1S,R2J,R3E), (ZC,R1S,R2J,R3F), (ZC,R1S,R2J,R3G), (ZC,R1S,R2J,R3H), (ZC,R1S,R2J,R3I), (ZC,R1S,R2J,R3J), (ZC,R1S,R2J,R3K), (ZC,R1S,R2J,R3L), (ZC,R1S,R2J,R3M), (ZC,R1S,R2J,R3N), (ZC,R1S,R2J,R3O), (ZC,R1S,R2J,R3P), (ZC,R1S,R2J,R3Q), (ZC,R1S,R2J,R3R), (ZC,R1S,R2K,R3A), (ZC,R1S,R2K,R3B), (ZC,R1S,R2K,R3C), (ZC,R1S,R2K,R3D), (ZC,R1S,R2K,R3E), (ZC,R1S,R2K,R3F), (ZC,R1S,R2K,R3G), (ZC,R1S,R2K,R3H), (ZC,R1S,R2K,R3I), (ZC,R1S,R2K,R3J), (ZC,R1S,R2K,R3K), (ZC,R1S,R2K,R3L), (ZC,R1S,R2K,R3M), (ZC,R1S,R2K,R3N), (ZC,R1S,R2K,R3O), (ZC,R1S,R2K,R3P), (ZC,R1S,R2K,R3Q), (ZC,R1S,R2K,R3R), (ZC,R1S,R2L,R3A), (ZC,R1S,R2L,R3B), (ZC,R1S,R2L,R3C), (ZC,R1S,R2L,R3D), (ZC,R1S,R2L,R3E), (ZC,R1S,R2L,R3F), (ZC,R1S,R2L,R3G), (ZC,R1S,R2L,R3H), (ZC,R1S,R2L,R3I), (ZC,R1S,R2L,R3J), (ZC,R1S,R2L,R3K), (ZC,R1S,R2L,R3L), (ZC,R1S,R2L,R3M), (ZC,R1S,R2L,R3N), (ZC,R1S,R2L,R3O), (ZC,R1S,R2L,R3P), (ZC,R1S,R2L,R3Q), (ZC,R1S,R2L,R3R), (ZC,R1S,R2M,R3A), (ZC,R1S,R2M,R3B), (ZC,R1S,R2M,R3C), (ZC,R1S,R2M,R3D), (ZC,R1S,R2M,R3E), (ZC,R1S,R2M,R3F), (ZC,R1S,R2M,R3G), (ZC,R1S,R2M,R3H), (ZC,R1S,R2M,R3I), (ZC,R1S,R2M,R3J), (ZC,R1S,R2M,R3K), (ZC,R1S,R2M,R3L), (ZC,R1S,R2M,R3M), (ZC,R1S,R2M,R3N), (ZC,R1S,R2M,R3O), (ZC,R1S,R2M,R3P), (ZC,R1S,R2M,R3Q), (ZC,R1S,R2M,R3R), (ZC,R1S,R2N,R3A), (ZC,R1S,R2N,R3B), (ZC,R1S,R2N,R3C), (ZC,R1S,R2N,R3D), (ZC,R1S,R2N,R3E), (ZC,R1S,R2N,R3F), (ZC,R1S,R2N,R3G), (ZC,R1S,R2N,R3H), (ZC,R1S,R2N,R3I), (ZC,R1S,R2N,R3J), (ZC,R1S,R2N,R3K), (ZC,R1S,R2N,R3L), (ZC,R1S,R2N,R3M), (ZC,R1S,R2N,R3N), (ZC,R1S,R2N,R3O), (ZC,R1S,R2N,R3P), (ZC,R1S,R2N,R3Q), (ZC,R1S,R2N,R3R).
다른 바람직한 태양은 이하의 식 (g) 내지 (n)에 있어서 이하의 기를 갖는 것이다.
Figure 112009066584530-PCT00046
Figure 112009066584530-PCT00047
Figure 112009066584530-PCT00048
Figure 112009066584530-PCT00049
(상기 표 중, Me는 메틸, Et는 에틸, iPr은 아이소프로필, tBu는 t-뷰틸, cHex는 사이클로헥실, Ph는 페닐을 나타낸다)
R2, R3 및 A'의 조합 (R2, R3, A')가 이하인 화합물.
(R2,R3,A')= (R2O,R3S,A1), (R2O,R3S,A2), (R2O,R3S,A3), (R2O,R3S,A4), (R2O,R3S,A5), (R2O,R3S,A6), (R2O,R3S,A7), (R2O,R3T,A1), (R2O,R3T,A2), (R2O,R3T,A3), (R2O,R3T,A4), (R2O,R3T,A5), (R2O,R3T,A6), (R2O,R3T,A7), (R2O,R3U,A1), (R2O,R3U,A2), (R2O,R3U,A3), (R2O,R3U,A4), (R2O,R3U,A5), (R2O,R3U,A6), (R2O,R3U,A7), (R2O,R3V,A1), (R2O,R3V,A2), (R2O,R3V,A3), (R2O,R3V,A4), (R2O,R3V,A5), (R2O,R3V,A6), (R2O,R3V,A7), (R2O,R3W,A1), (R2O,R3W,A2), (R2O,R3W,A3), (R2O,R3W,A4), (R2O,R3W,A5), (R2O,R3W,A6), (R2O,R3W,A7), (R2O,R3X,A1), (R2O,R3X,A2), (R2O,R3X,A3), (R2O,R3X,A4), (R2O,R3X,A5), (R2O,R3X,A6), (R2O,R3X,A7), (R2P,R3S,A1), (R2P,R3S,A2), (R2P,R3S,A3), (R2P,R3S,A4), (R2P,R3S,A5), (R2P,R3S,A6), (R2P,R3S,A7), (R2P,R3T,A1), (R2P,R3T,A2), (R2P,R3T,A3), (R2P,R3T,A4), (R2P,R3T,A5), (R2P,R3T,A6), (R2P,R3T,A7), (R2P,R3U,A1), (R2P,R3U,A2), (R2P,R3U,A3), (R2P,R3U,A4), (R2P,R3U,A5), (R2P,R3U,A6), (R2P,R3U,A7), (R2P,R3V,A1), (R2P,R3V,A2), (R2P,R3V,A3), (R2P,R3V,A4), (R2P,R3V,A5), (R2P,R3V,A6), (R2P,R3V,A7), (R2P,R3W,A1), (R2P,R3W,A2), (R2P,R3W,A3), (R2P,R3W,A4), (R2P,R3W,A5), (R2P,R3W,A6), (R2P,R3W,A7), (R2P,R3X,A1), (R2P,R3X,A2), (R2P,R3X,A3), (R2P,R3X,A4), (R2P,R3X,A5), (R2P,R3X,A6), (R2P,R3X,A7), (R2Q,R3S,A1), (R2Q,R3S,A2), (R2Q,R3S,A3), (R2Q,R3S,A4), (R2Q,R3S,A5), (R2Q,R3S,A6), (R2Q,R3S,A7), (R2Q,R3T,A1), (R2Q,R3T,A2), (R2Q,R3T,A3), (R2Q,R3T,A4), (R2Q,R3T,A5), (R2Q,R3T,A6), (R2Q,R3T,A7), (R2Q,R3U,A1), (R2Q,R3U,A2), (R2Q,R3U,A3), (R2Q,R3U,A4), (R2Q,R3U,A5), (R2Q,R3U,A6), (R2Q,R3U,A7), (R2Q,R3V,A1), (R2Q,R3V,A2), (R2Q,R3V,A3), (R2Q,R3V,A4), (R2Q,R3V,A5), (R2Q,R3V,A6), (R2Q,R3V,A7), (R2Q,R3W,A1),
(R2Q,R3W,A2), (R2Q,R3W,A3), (R2Q,R3W,A4), (R2Q,R3W,A5), (R2Q,R3W,A6), (R2Q,R3W,A7), (R2Q,R3X,A1), (R2Q,R3X,A2), (R2Q,R3X,A3), (R2Q,R3X,A4), (R2Q,R3X,A5), (R2Q,R3X,A6), (R2Q,R3X,A7), (R2R,R3S,A1), (R2R,R3S,A2), (R2R,R3S,A3), (R2R,R3S,A4), (R2R,R3S,A5), (R2R,R3S,A6), (R2R,R3S,A7), (R2R,R3T,A1), (R2R,R3T,A2), (R2R,R3T,A3), (R2R,R3T,A4), (R2R,R3T,A5), (R2R,R3T,A6), (R2R,R3T,A7), (R2R,R3U,A1), (R2R,R3U,A2), (R2R,R3U,A3), (R2R,R3U,A4), (R2R,R3U,A5), (R2R,R3U,A6), (R2R,R3U,A7), (R2R,R3V,A1), (R2R,R3V,A2), (R2R,R3V,A3), (R2R,R3V,A4), (R2R,R3V,A5), (R2R,R3V,A6), (R2R,R3V,A7), (R2R,R3W,A1), (R2R,R3W,A2), (R2R,R3W,A3), (R2R,R3W,A4), (R2R,R3W,A5), (R2R,R3W,A6), (R2R,R3W,A7), (R2R,R3X,A1), (R2R,R3X,A2), (R2R,R3X,A3), (R2R,R3X,A4), (R2R,R3X,A5), (R2R,R3X,A6), (R2R,R3X,A7), (R2S,R3S,A1), (R2S,R3S,A2), (R2S,R3S,A3), (R2S,R3S,A4), (R2S,R3S,A5), (R2S,R3S,A6), (R2S,R3S,A7), (R2S,R3T,A1), (R2S,R3T,A2), (R2S,R3T,A3), (R2S,R3T,A4), (R2S,R3T,A5), (R2S,R3T,A6), (R2S,R3T,A7), (R2S,R3U,A1), (R2S,R3U,A2), (R2S,R3U,A3), (R2S,R3U,A4), (R2S,R3U,A5), (R2S,R3U,A6), (R2S,R3U,A7), (R2S,R3V,A1), (R2S,R3V,A2), (R2S,R3V,A3), (R2S,R3V,A4), (R2S,R3V,A5), (R2S,R3V,A6), (R2S,R3V,A7), (R2S,R3W,A1), (R2S,R3W,A2), (R2S,R3W,A3), (R2S,R3W,A4), (R2S,R3W,A5), (R2S,R3W,A6), (R2S,R3W,A7), (R2S,R3X,A1), (R2S,R3X,A2), (R2S,R3X,A3), (R2S,R3X,A4), (R2S,R3X,A5), (R2S,R3X,A6), (R2S,R3X,A7), (R2T,R3S,A1), (R2T,R3S,A2), (R2T,R3S,A3), (R2T,R3S,A4), (R2T,R3S,A5), (R2T,R3S,A6), (R2T,R3S,A7), (R2T,R3T,A1), (R2T,R3T,A2), (R2T,R3T,A3), (R2T,R3T,A4), (R2T,R3T,A5), (R2T,R3T,A6), (R2T,R3T,A7), (R2T,R3U,A1), (R2T,R3U,A2), (R2T,R3U,A3), (R2T,R3U,A4), (R2T,R3U,A5), (R2T,R3U,A6), (R2T,R3U,A7), (R2T,R3V,A1), (R2T,R3V,A2), (R2T,R3V,A3), (R2T,R3V,A4), (R2T,R3V,A5), (R2T,R3V,A6), (R2T,R3V,A7), (R2T,R3W,A1), (R2T,R3W,A2), (R2T,R3W,A3), (R2T,R3W,A4), (R2T,R3W,A5), (R2T,R3W,A6), (R2T,R3W,A7), (R2T,R3X,A1), (R2T,R3X,A2), (R2T,R3X,A3), (R2T,R3X,A4), (R2T,R3X,A5), (R2T,R3X,A6), (R2T,R3X,A7), (R2U,R3S,A1), (R2U,R3S,A2), (R2U,R3S,A3), (R2U,R3S,A4), (R2U,R3S,A5), (R2U,R3S,A6), (R2U,R3S,A7), (R2U,R3T,A1), (R2U,R3T,A2), (R2U,R3T,A3), (R2U,R3T,A4), (R2U,R3T,A5), (R2U,R3T,A6), (R2U,R3T,A7), (R2U,R3U,A1), (R2U,R3U,A2), (R2U,R3U,A3), (R2U,R3U,A4), (R2U,R3U,A5), (R2U,R3U,A6), (R2U,R3U,A7), (R2U,R3V,A1), (R2U,R3V,A2), (R2U,R3V,A3), (R2U,R3V,A4), (R2U,R3V,A5), (R2U,R3V,A6), (R2U,R3V,A7), (R2U,R3W,A1), (R2U,R3W,A2), (R2U,R3W,A3), (R2U,R3W,A4), (R2U,R3W,A5), (R2U,R3W,A6), (R2U,R3W,A7), (R2U,R3X,A1), (R2U,R3X,A2), (R2U,R3X,A3), (R2U,R3X,A4), (R2U,R3X,A5), (R2U,R3X,A6), (R2U,R3X,A7).
이하에 실시예를 나타내어 본 발명을 구체적으로 설명하지만, 본 발명은 이들에 한정되는 것이 아니다. 한편, 각 약호는 이하에 나타내는 의미를 갖는다.
Me: 메틸
Et: 에틸
Bu: 뷰틸
Ac: 아세틸
TMS: 테트라메틸실레인
TMS-Cl: 트라이메틸실릴 클로라이드
DMSO: 다이메틸설폭사이드
rt: 실온
실시예 1
5-사이클로헥실-4-(2,2-다이메틸프로피오노닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-1,5-다이하이드로피롤-2-온(I-32)의 제조
Figure 112009066584530-PCT00050
에틸(트라이메틸아세토)피루베이트(1.00g, 5m㏖), 4-아이소옥사졸-3-일아닐린(0.80g, 5m㏖)과 아세트산(4mL)의 혼합액에 사이클로헥산 카보알데하이드(0.61mL, 5m㏖)을 가하여 95℃에서 5시간 교반했다. 반응 후, 실온까지 냉각하고, 석출된 결정을 아세트산에틸로 세정하면서 여과 수취하여, 5-사이클로헥실-4-(2,2-다이메틸프로피오노닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-1,5-다이하이드로피롤-2-온(0.60g, 수율: 30%)을 담황색 결정으로서 수득했다.
융점: 259 내지 260℃, 1H-NMR(δppm TMS/DMSO-d6) 0.62-1.78(11H, m), 1.27(9H, s), 5.28(1H, d, J=2.4Hz), 7.20(1H, d, J=1.8Hz), 7.75(2H, d, J=8.7Hz), 7.98(2H, d, J=8.7Hz), 9.03(1H, d, J=1.8Hz), 11.84(1H, s)
실시예 2
5-(3-플루오로페닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메톡시벤조일)-1,5-다이하이드로피롤-2-온(I-26)의 제조
Figure 112009066584530-PCT00051
메틸(4-메톡시벤조일)피루베이트(0.24g, 1mol), 4-아이소옥사졸-3-일아닐린(0.16g, 1m㏖)과 다이옥세인(1mL)의 혼합액에 3-플루오로벤즈알데하이드(0.11mL, 1m㏖)을 가하여 실온에서 2일간 교반했다. 반응 후, 다이에틸에터(3mL)를 가하고 석출한 결정을 여과 수취하여, 5-(3-플루오로페닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메톡시벤조일)-1,5-다이하이드로피롤-2-온(0.16g, 수율: 34%)을 담황색 결정으로서 수득했다.
융점: 273 내지 274℃(분해), 1H-NMR(δppm TMS/DMSO-d6) 3.83(3H, s), 6.43(1H, s), 6.90-7.02(3H, m), 7.11(1H, d, J=1.7Hz), 7.23-7.35(3H, m), 7.75-7.87(6H, m), 8.97(1H, d, J=1.7Hz), 11.75(1H, brs).
실시예 3
3-tert-뷰틸-4-사이클로헥실-5-(4-아이소옥사졸-3-일페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(I-96)의 제조
Figure 112009066584530-PCT00052
5-사이클로헥실-4-(2,2-다이메틸프로피오노닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-1,5-다이하이드로피롤-2-온(0.10g, 0.25m㏖)과 아세트산(1mL)의 혼합액에 하이드라진1수화물(0.036mL, 0.75m㏖)을 가하여 85℃에서 3시간 교반했다. 반응액에 물(80mL)을 가하여 아세트산에틸(100mL)로 추출했다. 추출액을 포화 탄산수소나트륨수(80mL×2)로 수세하고, 무수황산마그네슘으로 건조 후, 감압 농축하여 수득된 잔사(殘渣)를 실리카겔 컬럼 크로마토그래피(아세트산에틸/n-헥세인)로 정제하고 수득된 결정을 재결정(아세트산에틸)하여 3-tert-뷰틸-4-사이클로헥실-5-(4-아이소옥사졸-3-일페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.072g, 수율: 71%)을 무색 결정으로서 수득했다.
융점: 251 내지 252℃, 1H-NMR(δppm TMS/DMSO-d6) 0.50-2.03(11H, m), 1.39(9H, s), 5.60(1H, s), 7.20(1H, d, J=1.8Hz), 7.72(2H, d, J=8.7Hz), 7.96(2H, d, J=8.7Hz), 9.02(1H, d, J=1.8Hz), 13.28(1H, s).
실시예 4
4-(1-에틸프로필)-5-(4-아이소옥사졸-3-일페닐)-3-(6-옥소-1,6-다이하이드로피리딘-3-일)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(I-198)의 제조
Figure 112009066584530-PCT00053
4-(1-에틸프로필)-5-(4-아이소옥사졸-3-일페닐)-3-(6-메톡시피리딘-3-일)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.067g, 0.15m㏖)과 요오드화나트륨(0.067g, 0.45m㏖)과 아세토나이트릴(3mL)의 혼합액에 클로로트라이메틸실레인(0.058mL, 0.45m㏖)을 가하여 환류 하에서 1시간 교반했다. 반응액에 물(50mL)과 아세트산에틸(50mL)을 가하고, 석출된 결정을 여과 수취하여, 4-(1-에틸프로필)-5-(4-아이소옥사졸-3-일페닐)-3-(6-옥소-1,6-다이하이드로피리딘-3-일)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.041g, 수율: 64%)을 담황색 결정으로서 수득했다.
융점: >290℃(분해), 1H-NMR(δppm TMS/DMSO-d6) 0.50-1.55(11H, m), 6.00(1H, d, J=2.5Hz), 6.49(1H, d, J=9.4Hz), 7.18(1H, d, J=1.8Hz), 7.70-7.90(4H, m), 8.01(2H, d, J=8.4Hz), 9.02(1H, d, J=1.8Hz), 12.04(1H, brs), 13.78(1H, brs).
실시예 5
3-하이드록시-4-(4-메톡시벤조일)-1-(4-메톡시이미노메틸페닐)-5-페닐-1,5-다이하이드로피롤-2-온(I-199)의 제조
Figure 112009066584530-PCT00054
3-하이드록시-1-(4-하이드록시메틸페닐)-4-(4-메톡시벤조일)-5-페닐-1,5-다이하이드로피롤-2-온(0.125g, 0.3m㏖)과 아세톤(20mL)의 혼합액에 산화망간(Ⅳ)(0.625g, 7.18m㏖)을 가하고 실온에서 2.5시간 교반 후, 산화망간(Ⅳ)(0.625g, 7.18m㏖)을 더욱 가하여 실온에서 4.5시간 교반했다. 반응 후, 불용인 산화망간(Ⅳ)을 셀라이트(celite)로 제거하고, 액체를 농축하여 1-(4-폼일페닐)-3-하이드록시-4-(4-메톡시벤조일)-5-페닐-1,5-다이하이드로피롤-2-온의 조제물을 수득했다. 수득된 조제물에 메탄올을 가하여 0.1M의 메탄올 용액을 조제했다.
1-(4-폼일페닐)-3-하이드록시-4-(4-메톡시벤조일)-5-페닐-1,5-다이하이드로피롤-2-온의 0.1M의 메탄올용액(1mL, 0.1m㏖ 상당)에 O-메틸하이드록실암모늄클로라이드(0.025g, 0.3m㏖)와 아세트산나트륨(0.025g, 0.3m㏖)을 가하여 환류하에서 3시간 교반했다. 반응액에 물(50mL)을 가하여 아세트산에틸(50mL)로 추출했다. 추출액을 포화 식염수(50mL)로 수세하고, 무수황산나트륨으로 건조 후 감압 농축하여 수득된 잔사에 아세트산에틸을 가하고, 석출된 결정을 여과 수취하여, 3-하이드록시-4-(4-메톡시벤조일)-1-(4-메톡시이미노메틸페닐)-5-페닐-1,5-다이하이드로피롤-2-온(1.3mg, 수율: 3%)을 담황색 결정으로서 수득했다.
융점: 226 내지 229℃, 1H-NMR(δppm TMS/DMSO-d6) 3.82(3H, s), 3.85(3H, s), 6.31(1H, s), 6.95-7.75(13H, m), 8.12(1H, s), 11.63(1H, brs).
실시예 6
1-(1,3-다이옥솔레인-2-일)-3-하이드록시-4-(4-메톡시벤조일)-5-페닐-1,5-다이하이드로피롤-2-온(I-200)의 제조
Figure 112009066584530-PCT00055
1-(4-폼일페닐)-3-하이드록시-4-(4-메톡시벤조일)-5-페닐-1,5-다이하이드로피롤-2-온의 0.1M 메탄올 용액(1mL, 0.1m㏖ 상당)을 농축 후, 톨루엔(1mL), 에틸렌글라이콜(0.033mL, 0.6m㏖)과 p-톨루엔설폰산1수화물(3.8mg, 0.02m㏖)을 가하여 3시간 공비 탈수(azeotropic dehydration)를 실시했다. 반응액에 물(100mL)을 가하여 아세트산에틸(100mL)로 추출했다. 추출액을 포화 식염수(100mL)로 수세하고 무수황산나트륨으로 건조 후 감압 농축하여, 수득된 잔사에 아세트산에틸을 가하고, 석출된 결정을 여과 수취하여, 1-(1,3-다이옥솔레인-2-일)-3-하이드록시-4-(4-메톡시벤조일)-5-페닐-1,5-다이하이드로피롤-2-온(3.8mg, 수율: 8%)을 담황색 결정으로서 수득했다.
융점: 216 내지 219℃, 1H-NMR(δppm TMS/DMSO-d6) 3.81(3H, s), 3.89-4.00(4H, m), 5.63(1H, s), 6.26(1H, s), 6.94-7.75(13H, m), 11.65(1H, brs).
실시예 7
3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메톡시벤조일)-5-(4-피페리딘)-1,5-다이하이드로피롤-2-온 염산염(I-201)의 제조
Figure 112009066584530-PCT00056
5-(1-tert-뷰톡시카보닐-4-피페리딘)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메톡시벤조일)-1,5-다이하이드로피롤-2-온(0.112g, 0.2m㏖)과 메탄올(1mL)의 혼합액에 4mol/L 염산의 다이옥세인 용액(0.2mL, 0.8m㏖)을 가하고 실온에서 2.5시간 교반하고, 4mol/L 염산의 다이옥세인 용액(0.2mL, 0.8m㏖)을 더욱 가하여 환류하에서 0.5시간 교반했다. 반응 후, 감압 농축하여 3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메톡시벤조일)-5-(4-피페리딘)-1,5-다이하이드로피롤-2-온 염산염(0.098g, 수율: 100%)을 미갈색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 1.25-2.09(5H, m), 2.50-2.74(2H, m), 3.09-3.17(2H, m), 3.90(3H, s), 5.58(1H, s), 7.09(2H, d, J=8.6Hz), 7.21(1H, d, J=1.5Hz), 7.82-7.89(4H, m), 8.02(2H, d, J=8.6Hz), 8.11(1H, brs), 8.58(1H, brs), 9.04(1H, d, J=1.5Hz), 11.55(1H, brs).
실시예 8
3-(4-메톡시페닐)-5-(4-옥사졸-2-일페닐)-4-페닐-4,5-다이하이드로-1H-피롤로[3,4- c]피라졸-6-온의 제조(I-247)
Figure 112009066584530-PCT00057
5-(4-브로모페닐)-3-(4-메톡시페닐)-4-페닐-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.138g, 0.3m㏖)과 옥사졸-2-일트라이뷰틸주석(0.134g, 0.37m㏖), 트리스-(2-퓨릴)포스핀(0.014g, 0.06m㏖), 트리스(다이벤질리덴아세톤)다이팔라듐(O)(0.027g, 0.03m㏖), 다이옥세인(1.5mL)의 혼합액을 마이크로웨이브 조사 하 130℃에서 75분간 교반했다. 반응액을 실리카겔 컬럼 크로마토그래피(아세트산에틸/n-헥세인)로, 수득된 목적물의 프랙션(fraction)을 농축하면서, 석출된 결정을 여과 수취하여, 3-(4-메톡시페닐)-5-(4-옥사졸-2-일페닐)-4-페닐-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(12 mg, 수율」0%)을 무색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 3.75(3H, s), 6.86(1H, s), 6.91-7.92(13H, m), 8.17(1H, s), 14.00(1H, brs).
실시예 9
5-사이클로헥실-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-카복시벤조일)-1,5-다이하이드로피롤-2-온의 제조
Figure 112009066584530-PCT00058
5-사이클로헥실-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메톡시카보닐벤조일)-1,5-다이하이드로피롤-2-온(1.98g, 4.07m㏖), THF(20mL)과 메탄올(13mL)의 혼합액에 2N 수산화나트륨 수용액(5.09mL)을 가하여 80℃ 유욕(油浴)에서 2시간 교반했다. 반응 후, 빙냉(氷冷) 하에서 2N 염산(5.09mL)을 가한 후에, 아세트산에틸과 물을 더욱 가하여 실온에서 하룻밤 방치하고, 석출된 결정을 여과 수취하여, 5-사이클로헥실-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-카복시벤조일)-1,5-다이하이드로피롤-2-온(1.70g, 수율: 88%)을 황색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 0.73-1.80(11H, m), 5.49(1H, d, J=2.4Hz), 7.21(1H, d, J=1.7Hz), 7.80-8.11(8H, m), 9.04(1H, d, J=1.7Hz).
실시예 1O
5-사이클로헥실-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메틸카밤오일벤조일)-1,5-다이하이드로피롤-2-온의 제조
Figure 112009066584530-PCT00059
5-사이클로헥실-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-카복시벤조일)-1,5-다이하이드로피롤-2-온(0.095g, 0.2m㏖)과 DMF(2mL)의 혼합액에 메틸아민염산염(0.020g, 0.3m㏖), 1-하이드록시벤조트라이아졸(0.041g, 0.3m㏖), 4-다이메틸아미노피리딘의 0.005g, 0.04m㏖), 염산 1-에틸-3-(3-다이메틸아미노프로필)카보다이이미드(0.058g, 0.3m㏖) 및 트라이에틸아민(0.042mL, 0.3m㏖)을 가하여 실온에서 1시간 교반했다. 반응 후 아세트산에틸과 물을 가하고, 석출된 결정을 여과 수취하여, 5-사이클로헥실-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메틸카밤오일벤조일)-1,5-다이하이드로피롤-2-온(0.062g, 수율: 64%)을 담황색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 0.72-1.80(11H, m), 2.81(3H, d, J=4.5Hz), 5.48(1H, d, J=2.5Hz), 7.21(1H, d, J=1.7Hz), 7.80-8.03(8H, m), 8.64(1H, d, J=4.5Hz), 9.04(1H, d, J=1.7Hz), 11.73(1H, brs)
실시예 11
3-t-뷰틸-5-(4-아이소옥사졸-4-일페닐)-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온의 제조
Figure 112009066584530-PCT00060
5-(4-브로모페닐)-3-t-뷰틸-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.10g, 0.23m㏖), 4-(4,4,5,5-테트라메틸-1,3-2-다이옥사보레인-2-일)아이소옥사졸(0.066g, 0.34m㏖), 인산 삼칼륨(0.145g, 0.68m㏖)과 에틸렌 글라이콜 다이메틸에터(3mL)와 물(0.6mL)의 혼합액을 질소 치환한 후에[1,1'-비스(다이페닐포스피노)페로센]다이클로로팔라듐(Ⅱ)다이클로로메테인부가체(0.018g, 0.023m㏖)를 가하여, 환류 하에서 4시간 교반했다. 반응액을 실리카겔 컬럼 크로마토그래피(아세트산에틸/n-헥세인)로 정제하여, 3-t-뷰틸-5-(4-아이소옥사졸-4-일페닐)-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.012g, 수율: 12%)을 무색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 1.05(9H, s), 3.91(3H, s), 6.22-7.61(9H, m), 9.09(1H, s), 9.36(1H, s), 13.34(1H, s).
실시예 12
3-t-뷰틸-5-(4-퓨란-3-일페닐)-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온의 제조
Figure 112009066584530-PCT00061
5-(4-브로모페닐)-3-t-뷰틸-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.10g, 0.23m㏖), 퓨란-3-일보론산(0.038g, 0.34m㏖), 인산 삼칼륨(0.096g, 0.45m㏖)과 뷰탄올(1mL)의 혼합액을 질소치환한 후에 (2',4',6'-트라이아이소프로필바이페닐-2-일)포스핀(0.009g, 0.02m㏖)과 트리스(다이벤질리덴아세톤) 다이팔라듐(O)(0.004g, 0.004m㏖)을 가하여, 환류 하에서 3시간 교반했다. 반응액을 실리카겔 컬럼 크로마토그래피(아세트산에틸/n-헥세인)로 수득된 목적물의 프랙션을 농축하면서, 석출된 결정을 여과 수취하여, 3-t-뷰틸-5-(4-퓨란-3-일페닐)-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.061g, 수율: 63%)을 무색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 1.05(9H, s), 3.90(3H, s), 6.37-7.56(10H, m), 7.70(1H, s), 8.11(1H, s), 13.32(1H, s).
실시예 13
5-사이클로헥실-3-하이드록시-4-(4-하이드록시벤조일)-1-(4-아이소옥사졸-3-일페닐)-1,5-다이하이드로피롤-2-온의 제조
Figure 112009066584530-PCT00062
5-사이클로헥실-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메톡시벤조일)-1,5-다이하이드로피롤-2-온(0.229g, 0.5m㏖)과 다이클로로메테인(10mL)의 혼합액에 빙냉 하에서 1M 삼브롬화붕소다이클로로메테인 용액(5.0mL, 5m㏖)을 가하여 실온에서 3일간 교반했다. 반응 후 빙냉 하에서 소량의 탄산칼륨을 가하여 과잉의 삼브롬화붕소를 분해하고, 1N 수산화나트륨 수용액을 가한 후 아세트산에틸로 세정했다. 수층을 1N 염산으로 중화하여 석출된 결정을 여과 수취하고, 뜨거운 아세트산에틸로 세정하여 5-사이클로헥실-3-하이드록시-4-(4-하이드록시벤조일)-1-(4-아이소옥사졸-3-일페닐)-1,5-다이하이드로피롤-2-온(0.068g, 수율: 31%)을 무색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 0.73-1.80(11H, m), 5.41(1H, d, J=2.5Hz), 6.88-6.91(2H, m), 7.20(1H, d, J=1.7Hz), 7.78-8.01(6H, m), 9.03(1H, d, J=1.7Hz), 10.42(1H, brs), 11.14(1H, brs).
실시예 14
5-사이클로헥실-3-하이드록시-4-(4-하이드록시메틸벤조일)-1-(4-아이소옥사졸-3-일페닐)-1,5-다이하이드로피롤-2-온의 제조
Figure 112009066584530-PCT00063
메틸 4-(2-테트라하이드로-2H-피란옥시메틸)벤조일피루베이트(0.17g, 0.53m㏖), 4-아이소옥사졸-3-일아닐린(0.085g, 0.53m㏖)과 아세트산(1mL)의 혼합액에 사이클로헥산 카보알데하이드(0.064mL, 0.53m㏖)을 가하여 95℃에서 0.5시간 교반했다. 반응 후, 실온까지 냉각하고, 석출된 결정을 아세트산에틸로 세정하여 여과 수취하고, 수득된 조제물에 메탄올(5mL), THF(5mL) 및 p-톨루엔설폰산피리디늄(0.027g, 0.1 1m㏖)을 가하여, 60℃에서 0.5시간 교반했다. 반응액에 물을 가하여 클로로폼으로 추출한 후에 무수황산마그네슘으로 건조 후 감압 농축하고, 수득된 잔사를 재결정(아세트산에틸)하여 5-사이클로헥실-3-하이드록시-4-(4-하이드록시메틸벤조일)-1-(4-아이소옥사졸-3-일페닐)-1,5-다이하이드로피롤-2-온(0.022g, 수율: 9%)을 무색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 0.62-1.78(11H, m), 4.61(2H, d, J=5.6Hz), 5.38(1H, t, J=5.6Hz), 5.47(1H, d, J=2.0Hz), 7.21(1H, d, J=1.7Hz), 7.49-8.02(8H, m), 9.03(1H, d, J=1.7Hz), 11.40(1H, brs)
일반적 제조법 1
단리된 거울상체의 제조
Figure 112009066584530-PCT00064
[반응식 중의 기호는 상기와 같다]
화합물 (I'-1) 및 광학 분할제(예, (S)-메틸2-하이드록시-2-페닐아세테이트)를 적당한 용매 중에서 축합제(예, 아조다이카복실산아이소프로필)와 반응시켜 수득된 혼합물을, 통상적 방법(예, 컬럼크로마토그래피, 재결정 등)에 의해 정제하여 원하는 입체 배치를 갖는 부분입체이성질체(diastereomer)를 단리한다. 수득된 부분입체이성질체를 탈 보호반응(예, 수소첨가반응)에 부쳐 원하는 거울상체를 제조할 수 있다. 광학 분할제는 화합물 (I'-1)에 대하여 1 내지 4당량, 바람직하게는 1 내지 2.5당량 사용한다.
사용할 수 있는 용매로서는, 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화 탄화수소류(예, 사이클로헥세인, 헥세인 등), 에터류(예, 테트라하이드로퓨란, 다이에틸에터, 다이옥세인 등), 아마이드류(예, 다이메틸폼아마이드, 다이메틸아세토아마이드, N-메틸피롤리돈) 및 그들의 혼합 용매 등을 들 수 있다.
반응 온도는 -10 내지 150℃, 바람직하게는 0 내지 50℃이다. 반응 시간은 화합물에 따라 다르지만, 10분 내지 48시간 반응시키면 좋다.
일반적 제조법 1에 따라서 이하의 화합물을 제조했다.
실시예 15
(+)-4-(2,2-다이메틸프로피오노닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-5-(2-메톡시페닐)-1,5-다이하이드로피롤-2-온의 제조
Figure 112009066584530-PCT00065
4-(2,2-다이메틸프로피오노닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-5-(2-메톡시페닐)-1,5-다이하이드로피롤-2-온(0.43g, 1m㏖), (S)-메틸2-하이드록시-2-페닐아세테이트(0.23g, 1.4m㏖), 트라이페닐포스핀(0.34g, 1.3m㏖)과 THF(10mL)의 혼합액에 빙냉 하에서 아조다이카복실산아이소프로필(0.26mL, 1.3m㏖)을 가하여 실온에서 0.5시간 교반했다. 반응액을 감압 농축하여 실리카겔 컬럼 크로마토그래피(아세트산에틸/n-헥세인)로 정제하고, 수득된 부분입체이성질체혼합물을 재결정(아세트산에틸/n-헥세인)하여 부분입체이성질체(0.14g, 수율: 25%)를 무색 결정으로서 수득했다.
수득된 부분입체이성질체(0.058g, 0.1m㏖)를 다이옥세인(3mL)에 용해하고, 10% 팔라듐-탄소(0.026g)를 가하여, 실온에서 2시간 수소 첨가를 했다. 반응액을 셀라이트 여과 후 농축하여 수득된 잔사를 실리카겔 컬럼 크로마토그래피(아세트산 에틸/n-헥세인)로 정제하여, (+)-4-(2,2-다이메틸프로피오노닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-5-(2-메톡시페닐)-1,5-다이하이드로피롤-2-온(0.043g, 수율: 100%, 광학 순도: 100%ee)을 무색 결정으로서 수득했다.
[α]D: +62.5± 2.0°(in CHCl3), 1H-NMR(δppm TMS/DMSO-d6) 1.10(9H, s), 3.89(3H, brs), 6.39(1H, brs), 6.70-7.82(9H, m), 8.95(1H, d, J=1.8Hz), 12.08(1H, brs).
일반적 제조법 2
옥사졸체의 제조
Figure 112009066584530-PCT00066
[상기 식에서, X는 할로젠이며, 다른 기호는 상기와 같다]
화합물 (I'-2), 하이드록시이미노할로젠화물 및 염기를 적당한 용매 중에서 반응시켜 제조할 수 있다. 수득된 원하는 화합물은 필요하면 통상적 방법(예, 컬럼크로마토그래피, 재결정 등)에 의해 정제할 수 있다. 하이드록시이미노할로젠화물은 화합물 (I'-2)에 대하여 1 내지 5당량, 바람직하게는 1 내지 2.5당량 사용한다.
사용할 수 있는 용매로서는, 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화 탄화수소류(예, 사이클로헥세인, 헥세인 등), 에터류(예, 테트라하이드로퓨란, 다이에틸에터, 다이옥세인 등), 아마이드류(예, 다이메틸폼아마이드, 다이메틸아세토아마이드, N-메틸피롤리돈) 및 그들의 혼합 용매 등을 들 수 있다.
사용할 수 있는 염기로서는, 예컨대 금속수산화물(예, 수산화 나트륨, 수산화칼륨 등), 금속수소화물(예, 수소화나트륨, 수소화리튬 등), 금속탄산염(예, 탄산나트륨, 탄산칼륨, 탄산세슘 등) 등을 들 수 있고, 화합물 (I'-2)에 대하여 2당량 또는 그 이상, 바람직하게는 2 내지 10당량 사용할 수 있다.
반응 온도는 -40 내지 150℃, 바람직하게는 0 내지 50℃이다. 반응 시간은 화합물에 따라 다르지만 10분 내지 48시간 반응시키면 좋다.
상기 일반적 제조법 2에 따라서 이하의 화합물을 제조했다.
실시예 16
3-t-뷰틸-5-[4-(3-에톡시카보닐-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온의 제조
Figure 112009066584530-PCT00067
3-t-뷰틸-5-(4-에틴일페닐)-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[ 3,4-c]피라졸-6-온(1.51g, 3.9m㏖), 에틸2-클로로-2-하이드록시이미노아세테이트(1.19g, 7.8m㏖)와 THF(4mL)의 혼합액에 빙냉 하에서 트라이에틸아민(1.09mL, 7.8m㏖)의 THF(3mL)용액을 서서히 가하여, 0℃에서 4시간 교반했다. 반응액에 에틸2-클로로-2-하이드록시이미노아세테이트(1.19g, 7.8m㏖)를 가하고, 트라이에틸아민(0.81mL, 5.9m㏖)의 THF(3mL)용액을 서서히 더욱 가하여, 0℃에서 2시간 교반한 후, 하룻밤 방치했다. 석출된 결정을 제거하고, 감압 농축하고 수득된 잔사를 정제하여, 3-t-뷰틸-5-[4-(3-에톡시카보닐-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(1.26g, 수율: 64%)을 무색 고체로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 1.13(9H, s), 1.43(3H, t, J=7.1), 3.50(0.5H, s), 4.01(2.5H, s), 4.45(2H, q, J=7.3), 6.01(0.3H, s), 6.74-6.88(2.7H, m), 6.91(1H, d, J=8.6), 7.19(1H, t, J=7.4), 7.70(2H, d, J=8.6), 7.81(2H, d, J=8.6).
실시예 17
3-t-뷰틸-5-[4-(3-카복시-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온의 제조
Figure 112009066584530-PCT00068
3-t-뷰틸-5-[4-(3-에톡시카보닐-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(1.26g, 2.5m㏖), 메탄올(4mL), THF(4mL) 및 물(3mL)의 혼합액에 2N 수산화나트륨 수용액(1.5mL, 3m㏖)을 가하여, 50℃에서 1시간 교반했다. 반응 후, 물(40mL)과 1N 염산(2mL)을 가하여 아세트산에틸로 추출한 후에 포화 식염수로 세정하고, 무수황산나트륨으로 건조했다. 건조 후, 감압 농축하여 수득된 조제물을 에터에 현탁하고, 석출된 결정을 여과 수취 후, 3-t-뷰틸-5-[4-(3-카복시-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.84g, 수율: 71%)을 담황색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 1.05(9H, s), 3.96(3H, s), 6.50(0.3H, s), 6.68-6.94(2.7H, m), 7.00-7.25(2H, m), 7.29(1H, s), 7.77(2H, d, J=8.6), 7.87(2H, d, J=8.6), 13.43(1H, brs), 13.97(1H, brs).
실시예 18
3-t-뷰틸-5-[4-(3-다이메틸카밤오일-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온의 제조
Figure 112009066584530-PCT00069
3-t-뷰틸-5-[4-(3-카복시-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.080g, 0.17m㏖)과 DMF(2mL)의 혼합액에 다이메틸아민염산염(0.021g, 0.25m㏖), 1-하이드록시벤조트라이아졸(0.034g, 0.25m㏖), 4-다이메틸아미노피리딘(0.004g, 0.03m㏖), 염산 1-에틸-3-(3-다이메틸아미노프로필)카보다이이미드(0.048g, 0.25m㏖) 및 트라이에틸아민(0.035mL, 0.25m㏖)을 가하여 실온에서 2시간 교반했다. 반응 후, 아세트산에틸과 물을 가하고 석출된 결정을 여과 수취하여, 5-사이클로헥실-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-4-(4-메틸카밤오일벤조일)-1,5-다이하이드로피롤-2-온(0.055g, 수율: 65%)을 담황색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 1.05(9H, s), 3.02(3H, s), 3.39(1H, s), 6.50(0.3H, m), 6.65-6.96(2.7H, m), 7.06(1H, d, J=8.1), 7.14(1H, s), 7.19(1H, t, J=7.6), 7.76(2H, d, J=8.6), 7.84(2H, d, J=8.6), 13.32(1H, brs).
실시예 19
3-t-뷰틸-5-[4-(3-하이드록시메틸-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온의 제조
Figure 112009066584530-PCT00070
3-t-뷰틸-5-[4-(3-카복시-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.080g, 0.17m㏖), 트라이에틸아민(0.031mL, 0.22m㏖)과 THF(2mL)의 혼합액에 빙냉 하에서 클로로탄산에틸(0.019mL, 0.20m㏖)을 가하여 실온에서 2시간 교반했다. 계속해서 반응액에 수소화붕소나트륨(0.026g, 0.68m㏖)과 물(0.3mL)의 용액을 가하고, 메탄올(1mL)을 더욱 가하여 실온에서 10분간 교반했다. 반응 후, 물을 가하고 아세트산에틸로 추출한 후에 1N 염산, 포화 중조수(重曹水) 및 포화 식염수로 세정하여 무수황산나트륨으로 건조했다. 건조 후, 감압 농축하여 수득된 잔사를 다이클로로메테인, 다이에틸에터 및 아세트산에틸로 결정화하고, 석출된 결정을 여과 수취하여, 3-t-뷰틸-5-[4-(3-하이드록시메틸-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.068g, 수율: 88%)을 무색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 1.03(9H, s), 3.39(1H, s), 3.94(2H, s), 4.51(2H, d, J=26.9), 5.52(1H, t, J=5.8), 6.47(0.3H, s), 6.65-6.84(2.7H, m), 6.88(1H, s), 7.05(1H, d, J=8.1), 7.19(1H, t, J=7.6), 7.73(2H, d, J=8.6), 7.78(2H, d, J=8.6), 13.13(0.3H, brs), 13.39(0.6H, brs), 13.58(0.1H, brs).
일반적 제조법 3
Boc-보호 아민체의 제조
Figure 112009066584530-PCT00071
[반응식 중의 기호는 상기와 같다]
화합물 (I'-3), 염기 및 아지화 시약(예, 다이페닐포스포릴아자이도)을 적당한 용매 중에서 반응하고, 이어서 반응액에 t-뷰탄올과 건조제[예, 황산나트륨, 분말 분자체(molecular sieve)]를 가하여 제조할 수 있다. 수득된 원하는 화합물은, 필요하면 통상적 방법(예, 컬럼 크로마토그래피, 재결정, 추출 등)에 의해 정제할 수 있다. 아지화 시약은 화합물 (I'-3)에 대하여, 1 내지 4당량, 바람직하게는 1 내지 2.5당량 사용한다.
사용할 수 있는 용매로서는, 방향족 탄화수소류(예, 톨루엔, 벤젠, 자일렌 등), 포화탄화수소류(예, 사이클로헥세인, 헥세인 등), 에터류(예, 테트라하이드로퓨란, 다이에틸에터, 다이옥세인 등) 및 그들의 혼합 용매 등을 들 수 있다.
사용할 수 있는 염기로서는, 예컨대 금속수산화물(예, 수산화 나트륨, 수산화칼륨 등), 금속수소화물(예, 수소화나트륨, 수소화리튬 등), 금속탄산염(예, 탄산나트륨, 탄산칼륨, 탄산세슘 등) 등을 들 수 있고, 화합물 (I'-2)에 대하여 1당 량 또는 그 이상, 바람직하게는 1 내지 5당량 사용할 수 있다.
반응 온도는 0 내지 150℃, 바람직하게는 40 내지 120℃이다. 반응 시간은 화합물에 따라 다르지만 10분 내지 48시간 반응시키면 좋다.
일반적 제조법 3에 따라서 이하의 화합물을 제조했다.
실시예 20
3-t-뷰틸-5-[4-(3-t-뷰톡시카보닐아미노-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온의 제조
Figure 112009066584530-PCT00072
3-t-뷰틸-5-[4-(3-카복시-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.948g, 2.0m㏖), 트라이에틸아민(0.33mL, 2.4m㏖)과 DMF(15mL)의 혼합액에 다이페닐포스포릴아자이도(0.52mL, 2.4m㏖)를 가하여 60℃에서 2시간 교반했다. 계속해서 반응액에 t-뷰탄올(15mL)과 분말 분자체 4A(2g)를 가하고, 90℃에서 3시간 더욱 교반했다. 반응 후, 불용물을 여과로 제거하여 물을 가하고, 아세트산에틸로 추출한 후에 염화암모늄 수용액 및 포화 식염수로 세정하여, 무수황산나트륨으로 건조했다. 건조 후, 감압 농축하여 수득된 잔사를 다이클로로메테인으로 결정화하고, 석출된 결정을 여과 수취하여, 3-t-뷰틸-5-[4-(3-t-뷰톡시카보닐아미노-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.566g, 수율: 52%)을 무색 결정으로서 수득했다.
1H-NMR (δppm TMS/DMSO-d6) 1.05(9H, s), 1.47(9H, s), 3.95(3H, s), 6.77-6.80(3H, m), 7.00-7.11(2H, m), 7.19(1H, m), 7.72(2H, d, J=8.6), 7.77(2H, d, J=8.6), 10.34(1H, s), 13.24(1H, brs)
실시예 21
3-t-뷰틸-5-[4-(3-아미노-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온의 제조
Figure 112009066584530-PCT00073
3-t-뷰틸-5-[4-(3-t-뷰톡시카보닐아미노-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.036g, 0.7m㏖)과 메탄올(2mL)의 혼합액에 진한 염산(0.07mL)을 가하여 60℃에서 2시간 교반했다. 반응 후, 석출된 결정을 여과 수취하고, 수득된 결정을 재결정(메탄올/다이클로로메테인)하여 3-t-뷰틸-5-[4-(3-아미노-5-아이소옥사졸릴)페닐]-4-(2-메톡시페닐)-4,5-다이하이드로-1H-피롤로[3,4-c]피라졸-6-온(0.02g, 수율: 68%)을 담황색 결정으로 서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 1.05(9H, s), 3.38(1H, s), 3.94(2H, s), 5.60(2H, s), 6.21(1H, s), 6.44(0.3H, s), 6.65-6.94(2.7H, m), 7.04(1H, d, J=8.1), 7.19(1H, t, J=7.6), 7.67(4H, s), 13.11(0.2H, brs), 13.37(0.7H, brs), 13.56(0.1H, brs)
실시예 22
4-(1,2-다이옥소프로필)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-5-(2-메톡시페닐)-1,5-다이하이드로피롤-2-온의 제조
Figure 112009066584530-PCT00074
메틸다이메톡시(메틸)아세토피루베이트염(0.24g, 1m㏖), 4-아이소옥사졸-3-일아닐린(0.16g, 1m㏖)과 아세트산(2mL)의 혼합액에 2-메톡시벤즈알데하이드(0.14g, 1m㏖)를 가하여 실온에서 하룻밤 교반했다. 반응 후, 물을 가하고, 석출된 결정을 여과 수취하고, 수득된 결정을 재결정(다이클로로메테인/에터)하여 4-(2,2-다이메톡시프로피오노닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-5-(2-메톡시페닐)-1,5-다이하이드로피롤-2-온(0.22g, 수율: 47%)을 담황색 결정으로서 수득했다.
4-(2,2-다이메톡시프로피오노닐)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-5-(2-메톡시페닐)-1,5-다이하이드로피롤-2-온(0.08g, 0.17m㏖)에 아세트산(0.1mL)과 물(0.9mL)을 가하여 95℃에서 15분간 교반했다. 반응 후, 물을 가하고 아세트산에틸로 추출한 후에 무수황산나트륨으로 건조했다. 건조 후, 감압 농축하여 수득된 잔사를 다이클로로메테인과 에터로 결정화하고, 석출된 결정을 여과 수취하여, 4-(1,2-다이옥소프로필)-3-하이드록시-1-(4-아이소옥사졸-3-일페닐)-5-(2-메톡시페닐)-1,5-다이하이드로피롤-2-온(0.05g, 수율: 70%)을 황색 결정으로서 수득했다.
1H-NMR(δppm TMS/DMSO-d6) 2.24(3H, s), 3.80(3H, s), 6.38(1H, s), 6.82(1H, t, J=7.3), 6.93(1H, d, J=7.3), 7.08(1H, d, J=1.6), 7.13-7.18(2H, m), 7.70-7.84(4H, m), 8.96(1H, d, J=1.6).
상기 합성 경로, 일반적 제조법 및 실시예에 기재된 방법에 준하여 이하의 화합물을 수득했다. 구조 및 물성을 이하에 나타낸다.
Figure 112009066584530-PCT00075
Figure 112009066584530-PCT00076
Figure 112009066584530-PCT00077
Figure 112009066584530-PCT00078
Figure 112009066584530-PCT00079
Figure 112009066584530-PCT00080
Figure 112009066584530-PCT00081
Figure 112009066584530-PCT00082
Figure 112009066584530-PCT00083
Figure 112009066584530-PCT00084
Figure 112009066584530-PCT00085
Figure 112009066584530-PCT00086
Figure 112009066584530-PCT00087
Figure 112009066584530-PCT00088
Figure 112009066584530-PCT00089
Figure 112009066584530-PCT00090
Figure 112009066584530-PCT00091
Figure 112009066584530-PCT00092
Figure 112009066584530-PCT00093
Figure 112009066584530-PCT00094
Figure 112009066584530-PCT00095
Figure 112009066584530-PCT00096
Figure 112009066584530-PCT00097
Figure 112009066584530-PCT00098
Figure 112009066584530-PCT00099
Figure 112009066584530-PCT00100
Figure 112009066584530-PCT00101
Figure 112009066584530-PCT00102
Figure 112009066584530-PCT00103
Figure 112009066584530-PCT00104
Figure 112009066584530-PCT00105
Figure 112009066584530-PCT00106
Figure 112009066584530-PCT00107
Figure 112009066584530-PCT00108
Figure 112009066584530-PCT00109
Figure 112009066584530-PCT00110
Figure 112009066584530-PCT00111
Figure 112009066584530-PCT00112
Figure 112009066584530-PCT00113
Figure 112009066584530-PCT00114
Figure 112009066584530-PCT00115
Figure 112009066584530-PCT00116
Figure 112009066584530-PCT00117
Figure 112009066584530-PCT00118
Figure 112009066584530-PCT00119
Figure 112009066584530-PCT00120
Figure 112009066584530-PCT00121
Figure 112009066584530-PCT00122
Figure 112009066584530-PCT00123
Figure 112009066584530-PCT00124
Figure 112009066584530-PCT00125
Figure 112009066584530-PCT00126
Figure 112009066584530-PCT00127
Figure 112009066584530-PCT00128
Figure 112009066584530-PCT00129
Figure 112009066584530-PCT00130
Figure 112009066584530-PCT00131
Figure 112009066584530-PCT00132
Figure 112009066584530-PCT00133
Figure 112009066584530-PCT00134
Figure 112009066584530-PCT00135
Figure 112009066584530-PCT00136
Figure 112009066584530-PCT00137
Figure 112009066584530-PCT00138
Figure 112009066584530-PCT00139
Figure 112009066584530-PCT00140
Figure 112009066584530-PCT00141
Figure 112009066584530-PCT00142
Figure 112009066584530-PCT00143
Figure 112009066584530-PCT00144
Figure 112009066584530-PCT00145
Figure 112009066584530-PCT00146
Figure 112009066584530-PCT00147
Figure 112009066584530-PCT00148
Figure 112009066584530-PCT00149
Figure 112009066584530-PCT00150
Figure 112009066584530-PCT00151
Figure 112009066584530-PCT00152
Figure 112009066584530-PCT00153
Figure 112009066584530-PCT00154
Figure 112009066584530-PCT00155
Figure 112009066584530-PCT00156
Figure 112009066584530-PCT00157
Figure 112009066584530-PCT00158
Figure 112009066584530-PCT00159
Figure 112009066584530-PCT00160
Figure 112009066584530-PCT00161
Figure 112009066584530-PCT00162
Figure 112009066584530-PCT00163
Figure 112009066584530-PCT00164
Figure 112009066584530-PCT00165
Figure 112009066584530-PCT00166
Figure 112009066584530-PCT00167
Figure 112009066584530-PCT00168
Figure 112009066584530-PCT00169
Figure 112009066584530-PCT00170
Figure 112009066584530-PCT00171
Figure 112009066584530-PCT00172
Figure 112009066584530-PCT00173
Figure 112009066584530-PCT00174
Figure 112009066584530-PCT00175
Figure 112009066584530-PCT00176
Figure 112009066584530-PCT00177
Figure 112009066584530-PCT00178
Figure 112009066584530-PCT00179
Figure 112009066584530-PCT00180
Figure 112009066584530-PCT00181
Figure 112009066584530-PCT00182
Figure 112009066584530-PCT00183
Figure 112009066584530-PCT00184
Figure 112009066584530-PCT00185
Figure 112009066584530-PCT00186
Figure 112009066584530-PCT00187
Figure 112009066584530-PCT00188
Figure 112009066584530-PCT00189
Figure 112009066584530-PCT00190
Figure 112009066584530-PCT00191
Figure 112009066584530-PCT00192
Figure 112009066584530-PCT00193
Figure 112009066584530-PCT00194
Figure 112009066584530-PCT00195
Figure 112009066584530-PCT00196
Figure 112009066584530-PCT00197
Figure 112009066584530-PCT00198
Figure 112009066584530-PCT00199
Figure 112009066584530-PCT00200
Figure 112009066584530-PCT00201
Figure 112009066584530-PCT00202
Figure 112009066584530-PCT00203
Figure 112009066584530-PCT00204
Figure 112009066584530-PCT00205
Figure 112009066584530-PCT00206
Figure 112009066584530-PCT00207
Figure 112009066584530-PCT00208
Figure 112009066584530-PCT00209
Figure 112009066584530-PCT00210
Figure 112009066584530-PCT00211
Figure 112009066584530-PCT00212
Figure 112009066584530-PCT00213
Figure 112009066584530-PCT00214
Figure 112009066584530-PCT00215
Figure 112009066584530-PCT00216
Figure 112009066584530-PCT00217
Figure 112009066584530-PCT00218
Figure 112009066584530-PCT00219
Figure 112009066584530-PCT00220
Figure 112009066584530-PCT00221
Figure 112009066584530-PCT00222
Figure 112009066584530-PCT00223
Figure 112009066584530-PCT00224
Figure 112009066584530-PCT00225
Figure 112009066584530-PCT00226
Figure 112009066584530-PCT00227
Figure 112009066584530-PCT00228
Figure 112009066584530-PCT00229
Figure 112009066584530-PCT00230
Figure 112009066584530-PCT00231
Figure 112009066584530-PCT00232
Figure 112009066584530-PCT00233
Figure 112009066584530-PCT00234
Figure 112009066584530-PCT00235
Figure 112009066584530-PCT00236
Figure 112009066584530-PCT00237
Figure 112009066584530-PCT00238
Figure 112009066584530-PCT00239
Figure 112009066584530-PCT00240
Figure 112009066584530-PCT00242
Figure 112009066584530-PCT00243
Figure 112009066584530-PCT00244
Figure 112009066584530-PCT00245
Figure 112009066584530-PCT00246
Figure 112009066584530-PCT00247
Figure 112009066584530-PCT00248
Figure 112009066584530-PCT00249
Figure 112009066584530-PCT00250
Figure 112009066584530-PCT00251
Figure 112009066584530-PCT00252
Figure 112009066584530-PCT00253
Figure 112009066584530-PCT00254
Figure 112009066584530-PCT00255
(표 중,
Figure 112009066584530-PCT00256
는
Figure 112009066584530-PCT00257
,
Figure 112009066584530-PCT00258
는
Figure 112009066584530-PCT00259
,
Figure 112009066584530-PCT00260
는
Figure 112009066584530-PCT00261
,
Figure 112009066584530-PCT00262
는
Figure 112009066584530-PCT00263
,
Figure 112009066584530-PCT00264
는
Figure 112009066584530-PCT00265
,
Figure 112009066584530-PCT00266
는
Figure 112009066584530-PCT00267
,
Figure 112009066584530-PCT00268
는
Figure 112009066584530-PCT00269
를 나타낸다.)
시험예
인간 P2X3 수용체 유전자(GenBank 등록 배열 Y07683)를 C6BU-1세포에 도입한 안정 발현 세포주를 PDL코팅 96구 마이크로플레이트에 1구당 8,000개가 되도록 파종하고, 배지(8.3% 소(牛) 태아혈청, 8.3% 말(馬) 혈청, 1% 항생물질 항진균제 혼합 용액을 포함하는 DMEM) 중에서, 37℃, 5% 이산화탄소 하에서 1일간 배양했다. 배지를 Fluo-3-AM 4μM을 포함하는 첨가액(20mM HEPES, 137mM NaC1, 2.7mM KCl, 0.9mM MgCl2, 5.0mM CaCl2, 5.6mM D-글루코스, 2.5mM 프로베네시드, 10% BSA, 0.08% 플루로닉 F-127, pH7.5)으로 치환하여, 37℃, 5% 이산화탄소 하에서 1시간 인큐베이션했다. 세정용 완충액(20mM HEPES, 137mM NaCl, 2.7mM KCl, 0.9mM MgCl, 5.0mM CaCl, 5.6mM D-글루코스, 2.5mM프로베네시드, pH7.5)으로 세정하여, 1구당 40μl의 세정용 완충액으로 채웠다. 마이크로플레이트를 고효율 스크리닝 시스템 FDSS 3000(하마마쯔 포토닉스사)에 설치했다. FDSS 3000에 의한 형광 강도의 측정을 시작하고, 희석용 완충액(20mM HEPES, 137mM NaCl, 2.7mM KCl, 0.9mM MgCl2, 5.0mM CaCl2, 5.6mM D-글루코스, 2.5mM 프로베네시드, 0.1% 플루로닉 F-127, pH7.5)으로 다른 농도가 되도록 희석한 피검 화합물 DMSO 용액을 1구당 40μl씩 FDSS 3000에 내장된 자동분주장치로 나누어 주입했다. 5분 후, 희석용 완충액으로 희석한 40nM ATP 용액 50μl을 FDSS 3000에 내장된 자동분주장치로 나누어 주입하고, 그 후 3분간 형광 강도의 측정을 계속했다. 측정된 형광 강도의 값으로부터, ATP 용액 첨가후의 형광 강도의 최대치를 측정 개시시의 형광 강도에 대한 비로 나타낸, 비최대 형광 강도를 마이크로플레이트의 구마다 산출했다. 피검 화합물를 포함하지 않는 경우의 비최대 형광 강도의 값을 저해 0%, ATP 대신에 희석용 완충액을 첨가한 경우의 비최대 형광 강도의 값을 저해 100%로 하여, 저해 50%가 되는 농도(IC50)를 산출하여 피검 화합물의 저해 활성을 평가했다. 비최대 형광강도의 산출은 FDSS 소프트웨어(하마마쯔 포토닉스사)를 이용하여 실시했다. IC50의 산출은 마이크로소프트·엑셀(Microsoft사) 및 XLfit(idbs사)의 소프트웨어를 이용하여 실시했다.
본 발명 화합물의 시험 결과를 이하의 표에 나타낸다.
Figure 112009066584530-PCT00270
Figure 112009066584530-PCT00271
본 발명의 화합물은 P2X3 수용체에 대한 저해 활성을 나타내었다. 또한, 본 발명의 화합물은 P2X3 서브 타입에 작용하기 때문에, 마찬가지로 P2X2 서브 타입을 포함하여 구성되는 P2X2/3 수용체에 대하여도 저해 활성을 나타낸다고 생각된다.
본 발명의 화합물은 P2X3 및/또는 P2X2/3 수용체에 대한 길항 작용을 가지며, P2X3 및/또는 P2X2/3 수용체가 관여하는 질환 또는 상태, 예컨대 만성 동통, 과민성 방광에 대하여 유용하다.

Claims (21)

  1. 화학식 1로 표시되는 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 함유하는, P2X3 및/또는 P2X2/3 수용체 길항제.
    [화학식 1]
    Figure 112009066584530-PCT00272
    [상기 식에서,
    Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이며,
    Z2는 ＝Ｏ 또는 ＝N―E(E는 수소, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 또는 치환기를 갖고 있어도 좋은 아미노)이거나, 또는
    Figure 112009066584530-PCT00273
    가
    Figure 112009066584530-PCT00274
    를 형성하고(R4및 R5는 각각 독립적으로 수소 또는 저급 알킬이고, R6은 수소, 치환기를 갖고 있어도 좋은 저급 알킬 또는 아실이며, r은 0 내지 2의 정수이다),
    Ra 및 Rb는 각각 독립적으로 수소 또는 저급 알킬이고,
    q는 0 내지 4의 정수이고,
    A는 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
    R1은 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알켄일, 치환기를 갖고 있어도 좋은 저급 알킨일, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노, 나이트로, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
    n은 0 내지 3의 정수이고(단,
    Figure 112009066584530-PCT00275
    가
    Figure 112009066584530-PCT00276
    를 형성할 때, A―(Rl)n은 수소이어도 좋다),
    R2는 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
    R3은 수소, 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이다]
  2. 제 1 항 있어서,
    Z1이 하이드록시이며, Z2가 ＝Ｏ인 P2X3 및/또는 P2X2/3 수용체 길항제.
  3. 제 1 항에 있어서,
    r이 0인 P2X3 및/또는 P2X2/3 수용체 길항제.
  4. 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,
    고리 A가 페닐, 피리딜 또는 싸이아졸릴인 P2X3 및/또는 P2X2/3 수용체 길항 제.
  5. 제 1 항 내지 제 4 항 중 어느 한 항에 있어서,
    R1이 치환기를 갖고 있어도 좋은 저급 알콕시카보닐 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 P2X3 및/또는 P2X2/3 수용체 길항제.
  6. 제 1 항 내지 제 5 항 중 어느 한 항에 있어서,
    R2가 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 페닐 또는 치환기를 갖고 있어도 좋은 피리딜인 P2X3 및/또는 P2X2/3 수용체 길항제.
  7. 제 1 항 내지 제 6 항 중 어느 한 항에 있어서,
    R3이 탄소수 3 내지 10의 알킬, 사이클로알킬 또는 치환기를 갖고 있어도 좋은 페닐인 P2X3 및/또는 P2X2/3 수용체 길항제.
  8. 제 1 항 내지 제 7 항 중 어느 한 항에 있어서,
    q가 0인 P2X3 및/또는 P2X2/3 수용체 길항제.
  9. 제 1 항 내지 제 7 항 중 어느 한 항에 있어서,
    q가 1인 P2X3 및/또는 P2X2/3 수용체 길항제.
  10. 화학식 2로 표시되는 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
    [화학식 2]
    Figure 112009066584530-PCT00277
    [상기 식에서,
    Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이며,
    Z2는 ＝Ｏ 또는 ＝N―E(E는 수소, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 또는 치환기를 갖고 있어도 좋은 아미노)이거나, 또는
    Figure 112009066584530-PCT00278
    가
    Figure 112009066584530-PCT00279
    를 형성하고(R4및 R5는 각각 독립적으로 수소 또는 저급 알킬이고, R6은 수소, 치환기를 갖고 있어도 좋은 저급 알킬 또는 아실이며, r은 0 내지 2의 정수이다),
    고리 A 및 고리 B는 각각 독립적으로 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
    R1a 및 R1b는 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알켄일, 치환기를 갖고 있어도 좋은 저급 알킨일, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노 또는 나이트로이고,
    m 및 p는 각각 독립적으로 0 내지 2의 정수이고,
    R2는 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이고,
    R3은 수소, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어 도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
    단, 고리 A가 피라졸론이고, 고리 B가 페닐인 화합물을 제외한다]
  11. 제 10 항에 있어서,
    Z1이 보호되어 있어도 좋은 알킬이고, Z2가 ＝Ｏ이며, R2가 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
  12. 제 10 항에 있어서,
    r이 O이고, R2가 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
  13. 제 9 항 내지 제 12항 중 어느 한 항에 있어서,
    고리 A가 페닐, 피리딜 또는 싸이아졸릴인 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
  14. 화학식 3으로 표시되는 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
    [화학식 3]
    Figure 112009066584530-PCT00280
    [상기 식에서,
    Z1은 보호되어 있어도 좋은 하이드록시, 보호되어 있어도 좋은 하이드록시아미노 또는 치환기를 갖고 있어도 좋은 아미노이고,
    Z2는 ＝Ｏ 또는 ＝N―E(E는 수소, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 또는 치환기를 갖고 있어도 좋은 아미노)이거나, 또는
    Figure 112009066584530-PCT00281
    가
    Figure 112009066584530-PCT00282
    를 형성하고(R4 및 R5는 각각 독립적으로 수소 또는 저급 알킬이고, R6은 수소, 치 환기를 갖고 있어도 좋은 저급 알킬 또는 아실이며, r은 0 내지 2의 정수이다),
    고리 A는 사이클로알킬, 사이클로알켄일, 아릴 또는 헤테로환식기이고,
    R1a는 각각 독립적으로 할로젠, 하이드록시, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬싸이오, 치환기를 갖고 있어도 좋은 아실, 카복시, 치환기를 갖고 있어도 좋은 저급 알콕시카보닐, 치환기를 갖고 있어도 좋은 카밤오일, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 아미노, 치환기를 갖고 있어도 좋은 설팜오일, 사이아노 또는 나이트로이고,
    m은 0 내지 2의 정수이고,
    R1c 및 R1d는 각각 독립적으로는 수소 또는 치환기를 갖고 있어도 좋은 저급 알킬이고,
    R2는 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 저급 알킬카밤오일, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기이며,
    R3은 수소, 치환기를 갖고 있어도 좋은 저급 알킬, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴, 치환기를 갖고 있어도 좋은 헤테로환식기이다]
  15. 제 14 항에 있어서,
    Z1이 보호되어 있어도 좋은 하이드록시이고, Z2가 ＝Ｏ이고, R2가 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
  16. 제 14 항에 있어서,
    r이 O이고, R2가 치환기를 갖고 있어도 좋은 알킬, 치환기를 갖고 있어도 좋은 저급 알콕시, 치환기를 갖고 있어도 좋은 사이클로알킬, 치환기를 갖고 있어도 좋은 사이클로알켄일, 치환기를 갖고 있어도 좋은 아릴 또는 치환기를 갖고 있어도 좋은 헤테로환식기인 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
  17. 제 14 항 내지 제 16 항 중 어느 한 항에 있어서,
    고리 A가 페닐, 피리딜 또는 싸이아졸릴인 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물.
  18. 제 10 항 내지 제 17 항 중 어느 한 항에 따른 화합물, 또는 그 제약상 허용 되는 염 또는 그들의 용매화물을 함유하는 의약 조성물.
  19. 제 10 항 내지 제 17 항 중 어느 한 항에 따른 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 함유하는 P2X3 및/또는 P2X2/3 수용체 길항제.
  20. P2X3 및/또는 P2X2/3 수용체가 관여하는 질환의 치료 및/또는 예방을 위한, 제 10 항 내지 제 17 항 중 어느 한 항에 따른 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물의 사용.
  21. 제 10 내지 제 17 항 중 어느 한 항에 따른 화합물, 또는 그 제약상 허용되는 염 또는 그들의 용매화물을 투여하는 것을 특징으로 하는, P2X3 및/또는 P2X2/3 수용체가 관여하는 질환의 치료 및/또는 예방 방법.
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