KR20070008541A - 신규한 인데노[2,1a]인덴 및 이소인돌[2,1-a]인돌 - Google Patents
신규한 인데노[2,1a]인덴 및 이소인돌[2,1-a]인돌 Download PDFInfo
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- KR20070008541A KR20070008541A KR1020067012980A KR20067012980A KR20070008541A KR 20070008541 A KR20070008541 A KR 20070008541A KR 1020067012980 A KR1020067012980 A KR 1020067012980A KR 20067012980 A KR20067012980 A KR 20067012980A KR 20070008541 A KR20070008541 A KR 20070008541A
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Abstract
Description
Claims (15)
- 하기 화학식 1의 인데노[2,1a]인덴 및 이소인돌[2,1-a]인돌 유도체, 약제학적으로 허용 가능한 그의 염, 또는 그의 입체 이성질체:[화학식 1]상기 화학식 1에서,X는 -CH2-, -CO-, -S-, 또는 -S(O)1 또는 2, 이고;[ ---- ] 은 단일결합 또는 이중결합이고;R1, R2, R3, R4, R6, R7 , R8 및 R9 은 각각 독립적으로 수소, 할로겐, 퍼할로알킬, 퍼할로알콕시, 히드록시, (C1-C3)알킬, (C3-C5)시클로알킬, (C1-C3)알콕시, 시클로(C3-C5)알콕시, 아릴, 아릴옥시, 아랄킬, 아랄콕시, 헤테로시클릴, 모노알킬아미노, 디알킬아미노, 및 티오알킬을 나타내고;R11, R12, R13 및 R14는 각각 독립적으로 수소, 할로겐, 옥소, 티오, 퍼할로알킬, 퍼할로알콕시, 히드록시, 티올, 또는 (C1-C3)알킬을 나타낸다.
- 제 1 항에 있어서, 화합물 그룹에서 선택되는 것을 특징으로 하는 화합물 또는 약제학적으로 허용 가능한 그의 염:1. (R,S) 10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;2. (R,S) 10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;3. (R,S) 2-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴-5,5-디옥사이드;4. (R,S) 2-메톡시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;5. (R,S) 1-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;6. (R,S) 2-에톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;7. (R,S) 2-에톡시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;8. (R,S) 2-이소프로폭시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;9. (R,S) 1-이소프로폭시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;10. (R,S) 2-시클로펜틸옥시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;11. (R,S) 3-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;12. (R,S) 3-클로로-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;13. (R,S) 10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;14. (R,S) 2-메톡시-11-(1-메틸피롤리딘-3-일)-6H-이소인돌로[2,1-a]인돌;15. (S) 10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;16. (S) 10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;17. (S) 2-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴-5,5-디옥사이드;18. (S) 2-메톡시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a] 인덴 5,5-디옥사이드;19. (S) 1-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;20. (S) 2-에톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;21. (S) 2-에톡시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;22. (S) 2-이소프로폭시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;23. (S) 1-이소프로폭시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;24. (S) 2-시클로펜틸옥시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;25. (S) 3-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;26. (S) 3-클로로-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;27. (S) 10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;28. (S) 2-메톡시-11-(1-메틸피롤리딘-3-일)-6H-이소인돌로[2,1-a]인돌;29. (R) 10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;30. (R) 10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;31. (R) 2-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴-5,5-디옥사이드;32. (R) 2-메톡시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;33. (R) 1-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;34. (R) 2-에톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;35. (R) 2-에톡시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;36. (R) 2-이소프로폭시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;37. (R) 1-이소프로폭시-10-(1-에틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;38. (R) 2-시클로펜틸옥시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;39. (R) 3-메톡시-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;40. (R) 3-클로로-10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;41. (R) 10-(1-메틸피롤리딘-3-일)-5-티아-4b-아자-인데노[2,1-a]인덴 5,5-디옥사이드;42. (R) 2-메톡시-11-(1-메틸피롤리딘-3-일)-6H-이소인돌로[2,1-a]인돌.
- 하기 화학식 2의 화합물을 촉매로서 Pd(O) 또는 Pd(Ⅱ) 유도체를 이용하여 고리화하는 단계를 포함하는, 제 1항에 따른 화학식 1의 화합물의 제조방법:[화학식 2]상기 화학식 2에서,X는 -CH2-, -CO-, -S-, 또는 -S(O)1 또는 2 이고;[ ---- ] 은 단일결합 또는 이중결합이고;R1, R2, R3, R4, R6, R7 , R8 및 R9 은 각각 독립적으로 수소, 할로겐, 퍼할로알킬, 퍼할로알콕시, 히드록시, (C1-C3)알킬, (C3-C5)시클로알킬, (C1-C3)알콕시, 시클로(C3-C5)알콕시, 아릴, 아릴옥시, 아랄킬, 아랄콕시, 헤테로시클릴, 모노알킬아미노, 디알킬아미노, 및 티오알킬을 나타내고;R11, R12, R13 및 R14는 각각 독립적으로 수소, 할로겐, 옥소, 티오, 퍼할로알킬, 퍼할로알콕시, 히드록시, 티올, 또는 (C1-C3)알킬을 나타내고;R5 또는 R10 그룹 중 어느 하나는 브로모, 클로로, 또는 요오도 같은 할로겐 원자이고, 다른 하나는 수소이다.
- 제 3 항에 있어서, 화학식 1의 유용한 화화합물을 획득하기 위해화학식 1의 라세믹 화합물을 실질적으로 순수한 광학적으로 활성인 형태로 전환시키는 단계; 또는화학식 1의 한 화합물을 화학식 1의 또 다른 화합물로 전환시키는 단계; 및/또는임의의 보호기를 제거하는 단계; 및/또는화학식 1의 화합물의 약제학적으로 허용 가능한 염 또는 프로드럭을 형성시키는 단계를 더 포함하는 것을 특징으로 하는 방법.
- 제 3 항 또는 제 4 항에 있어서, 상기 Pd(O) 또는 Pd(Ⅱ) 유도체는 테트라키스 트리페닐포스핀 팔라듐, (비스-트리-o-톨릴포스핀)팔라듐로부터 선택되며, 상기 고리화는 염기의 존재 하에서 수행하는 것을 특징으로 하는 방법.
- 제 3 항 내지 제 5 항 중 어느 한 항에 있어서, 상기 고리화는 염기의 존재 하에서 수행하는 것을 특징으로 하는 방법.
- 약제학적으로 허용 가능한 부형제 이외에 제 1 항 또는 제 2 항에 따른 하나 이상의 화학식 1의 화합물 또는 약제학적으로 허용 가능한 그의 염 중 하나를 함유하는 것을 특징으로 하는 약제학적 조성물.
- CNS 질환, 섭식 장애, 위장관 질환, 혈액학적 질환, 통증 질환, 호흡기 질환, 비뇨생식기 질환, 심혈관계 질환, 및 암의 치료 또는 예방에 사용하기 위한 제 1 항에 따른 화학식 1의 화합물의 용도.
- 제 6 항에 있어서, 상기 CNS 질환은 정신병, 망상분열증, 불안증, 우울증, 조증, 정신분열증, 정신분열형 장애, 편두통, 약물 중독, 경련성 장애, 인격 장애, 고혈압, 자폐증, 외상후 스트레스 증후군, 알콜 중독, 공황 발작, 강박반응성 장애, 시간생물학적 이상 하루주기 리듬(chronobiological abnormalities and circadian rhythms), 인지 기억 장애(예: 알츠하이머병 및 나이-관련 인지 감퇴), ADHD(집중력 결핍 장애/ 과활동성 증후군), 근위축성 측삭경화증, 약물 중독(예: 코카인, 에탄올, 니코틴, 및 벤조디아제핀)의 금단 증후군, 공황 발작, 그리고 척수 외상 및/또는 수두증과 같은 머리 이상, 약한 인지 손상, 및 다른 신경퇴행성 질환(예: 알츠하이머병, 파킨슨씨병, 및 헌팅톤 무도병)과 관련된 장애인 것을 특징으로 하는 화학식 1의 화합물의 용도.
- 제 6 항에 있어서, 위장관 장애는 IBS(과민성 대장 증후군) 또는 화학요법에 인한 구토증인 것을 특징으로 하는 화학식 1의 화합물의 용도.
- 제 6 항에 있어서, 섭식장애의 조절인 것을 특징으로 하는 화학식 1의 화합물의 용도.
- 제 7 항, 제 8 항, 및 제 9 항에 열거된 임상적 상태의 치료 및/또는 예방을 위한 의약의 제조를 위한 제 1 항의 화합물의 용도.
- 제 6 항에 정의된 화학식 1의 화합물 또는 제 5 항에 정의된 약제학적 조성물의 5-HT 수용체 서브타입의 활성이 선택적으로 조절되는데 사용되는 용도.
- 5-HT 수용체의 기능을 조절하기 위한 진단 도구로서, 제 1 항에 따른 화합물 과 관련된 방사성 동위원소로 표지된 화합물의 용도.
- 제 1 항에 정의된 화학식 1의 화합물을 이용하여, CNS 질환, 섭식 장애, 위장관 장애, 혈액학적 장애, 통증 질환, 호흡기 장애, 비뇨생식기 장애, 심혈관계 질환, 및 암을 예방 또는 치료하는 방법.
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ES2568262T3 (es) * | 2009-04-23 | 2016-04-28 | Abbvie Inc. | Moduladores de receptores de 5-HT y sus métodos de uso |
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US5994352A (en) * | 1998-11-13 | 1999-11-30 | Pfizer Inc. | 5-arylindole derivatives |
HUP0400684A2 (hu) * | 2000-12-22 | 2004-07-28 | Wyeth | 5-Hidroxitriptamin-6-ligandumként használható heterociklilindazol- és -azaindazol-származékok, előállításuk és ezeket tartalmazó gyógyszerkészítmények |
CA2433351A1 (en) * | 2001-01-30 | 2002-08-08 | Eli Lilly And Company | Benzenesulfonic acid indol-5-yl esters as antagonists of the 5-ht6 receptor |
DK1438045T3 (da) * | 2001-10-23 | 2007-06-11 | Biovitrum Ab | Anvendelse af indol- og indolin-derivater ved behandling af obesitet eller til reduktion af födeindtag |
ES2187300B1 (es) * | 2001-11-14 | 2004-06-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de sulfonamidas, su preparacion y su aplicacion como medicamentos. |
CA2470863C (en) * | 2001-12-20 | 2012-05-15 | Wyeth | Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
WO2003065046A2 (en) | 2002-02-01 | 2003-08-07 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with a new human 5-ht6 receptor |
JP2005522432A (ja) | 2002-02-05 | 2005-07-28 | グラクソ グループ リミテッド | ニューロン成長の促進方法 |
ATE343580T1 (de) * | 2002-06-21 | 2006-11-15 | Suven Life Sciences Ltd | Tetracyclische arylcarbonyl indole mit serotoninrezeptoraffinität als arzneimittel, verfahren zu ihrer herstellung und pharmazeutische zubereitungen |
CN1662538A (zh) * | 2002-06-21 | 2005-08-31 | 苏文生命科学有限公司 | 可作为治疗剂的对血清素受体具有亲和力的芳烷基吲哚、其制备工艺及其含有该物质的药物组合物 |
MXPA04012832A (es) * | 2002-06-21 | 2005-05-27 | Suven Life Sciences Ltd | Arilsulfonil indoles novedosos que tienen afinidad por el receptor de la serotonina, utiles como agentes terapeuticos, proceso para su preparacion y composiciones farmaceuticas que los contienen. |
AU2003285759B2 (en) | 2002-11-28 | 2010-01-28 | Suven Life Sciences Limited | N-arylsulfonyl-3-aminoalkoxyindoles |
AU2003292508A1 (en) | 2002-11-28 | 2004-06-18 | Suven Life Sciences Limited | N-arylalkyl-3-aminoalkoxyindoles and their use as 5-ht ligands |
CA2509982C (en) | 2002-11-28 | 2011-11-08 | Suven Life Sciences Limited | N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them |
NZ540841A (en) | 2002-12-18 | 2008-08-29 | Suven Life Sciences Ltd | Tetracyclic 3-substituted indoles having serotonin receptor affinity |
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