KR950702829A - 신경계 퇴행성 질환의 치료에 유용한 아나바세인 유도체 - Google Patents

신경계 퇴행성 질환의 치료에 유용한 아나바세인 유도체 Download PDF

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KR950702829A
KR950702829A KR1019950700698A KR19950700698A KR950702829A KR 950702829 A KR950702829 A KR 950702829A KR 1019950700698 A KR1019950700698 A KR 1019950700698A KR 19950700698 A KR19950700698 A KR 19950700698A KR 950702829 A KR950702829 A KR 950702829A
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compound
hydrogen
methyl
methoxy
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윌리암 알. 켐
존 에이. 졸테위츠
에드윈 엠. 메이어
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카렌 앤 홀브르크
유니버시티 오브 플로리다 리서치 파운데이션, 인코포레이티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

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  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

신규의 아나바세인과 아나바신 유도체는 뇌콜린 전달을 촉진시키는데 유용하고, 신경계의 퇴행성 질환의 치료에 유용하다.

Description

신경계 퇴행성 질환의 치료에 유용한 아나바세인 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 다음의 약물지입에 따른 수동적 회피행동, 이때 화합물 A는 3-[(2.4-디하이드록시)벤질리딘] 아나베이신, 화합물 B는3-[(2-하이드록시-4-메톡시)벤질리딘]아나베이신, 화합물 C는 5'-메틸아나베이신을 각각 나타낸다.
제2도는 다음의 약물주입에 따른 수동적 회피행동으로, 이때 화합물A는 3-[(2,4-디프로폭시)벤질리딘] 아나베이신, 화합물 B는 3-[(2,4-디펜톡시)벤질리딘]아나베이신, 화합물 C는 3-[(2.4-디메톡시)벤질리딘]2-페닐-3,4,5,6-테트라하이드로피리딘을 각각 나타낸다.
제3도는 상이한 약량에서 활성 회피행동의 GTS 효과.
제4도는 활성 회피행동에서 CTS와 THA의 효과.

Claims (25)

  1. 다음 구조식의 또는 이의 제약학적 수용가능한 염의 화합물 :
    이때, 질소원소를 포함하는 6원소링의 1과 2위치 사이의 점선을 광학적 결합을 나타내는 것으로 Y는 질소 또는 탄소이고, R1은 수소 또는 C1-C4 알킬; 그리고 R2는 수소, C1-C4 알킬 또는 =CH-X이고 이때 X는 각 알킬에서 1내지 4개 탄소를 가지는 N, N-디알킬아미노에 의해 선택적으로 치환된 나프틸, 알킬, 퓨릴, 퓨릴아크로일 또는
    에서 1내지 4개 탄소를 가지는 N, N-디알킬아미노에 의해 선택적으로 치환된 스티릴이고, 이때 R3, R4, R5는 알킬, 아미노, 시아노, N, N-디알킬아미노, 알킬, 할로, 하이드록실과 니트로 각각에서 1내지 4개 탄소를 가지는 N, N-디알킬아미노 각각에서 1내지 4개 탄소를 가지는 N, N-디알킬아미노에 의해 선택적으로 치환된 수소, C1-C4 알킬, C1-C6 알콕시에서 선택된 것이고, 이때 질소원소를 포함하는 6 원소고리의 1내지 2위치에 이중결합이 있는 경우, R1은 수소이고, R2는 1-메틸, 벤질리딘 그리고 (4-디메틸아미노) 벤질리딘이 아니며, 또한 질소를 포함하는 6원소고리의 1내지 2위치에 단일결합이 있는 경우, R1은 수소 R2는 1-메틸이 아니며, 구조식에서 질소를 포함하는 6원소고리의 1내지 2위치에 단일결합인 경우에 R1은 2'-메틸이고, R2는 수소가 아니며 Y가 탄소이면 R2는 =CH-X이다.
  2. 제1항에 있어서, 질소를 포함하는 6-원소고리의 1과 2위치에 이중결합이 있고 Y는 질소인 것을 특징으로 하는 화합물.
  3. 제2항에 있어서, R1이 수소이고 R2는 3-메틸, 4-메틸, 5-메틸 또는 6-메틸인 것을 특징으로 하는 화합물.
  4. 제2항에 있어서, R1이 수소이고 2-메틸, 4-메틸, 5-메틸 또는 6-메틸과 R2는 것을 특징으로 하는 화합물.
  5. 제1항에 있어서, 질소를 포함하는 6원소 고리의 1과 2위치에 단일결합이 있고 Y가 질소인 것을 특징으로 하는 화합물.
  6. 제1항에 있어서, R2는 =CH-X이고 Y는 질소인 것을 특징으로 하는 화합물.
  7. 제6항에 있어서, X가 스티릴인 것을 특징으로 하는 화합물.
  8. 제7항에 있어서, 스티릴기는 4-디메틸아미노에 의해 치환된 것을 특징으로 하는 화합물.
  9. 제6항에 있어서, X는
    인 것을 특징으로 하는 화합물.
  10. 제9항에 있어서, 패닐링의 4번위치에 부착된 R3는 아미노, 하이드록실, 클로로, 시아노, 디메틸아미노, 메틸, 메톡시, 니트로에서 선택되고 R4 와 R5는 수소인 것을 특징으로 하는 화합물.
  11. 제9항에 있어서, R1은 수소이고, R3와 R4는 메톡시이고 R5는 수소인 것을 특징으로 하는 화합물.
  12. 제11항에 있어서, R3는 2-메톡시이고 R4는 4-메톡시인 것을 특징으로 하는 화합물.
  13. 제9항에 있어서, R1은 수소이고, R3, R4, R5는 모두 메톡시인 것을 특징으로 하는 화합물.
  14. 제13항에 있어서, R3는 4-메톡시인 것을 특징으로 하는 화합물.
  15. 제9항에 있어서, R1은 수소이고, 질소를 포함하는 6원소 고리의 1과 2위치에 단일결합인 것을 특징으로 하는 화합물.
  16. 제15항에 있어서, R3는 4-메틸아미노이고, R$와 R5는 수소인 것을 특징으로 하는 화합물.
  17. 제9항에 있어서, 질소를 포함하는 6원소고리의 1과 2위치에 이중결합인 것을 특징으로 하는 화합물.
  18. 제6항에 있어서, X는 퓨릴 또는 퓨릴아크로일인 것을 특징으로 하는 화합물.
  19. 제1항에 있어서, Y는 탄소이고, 질소를 포함하는 6원소고리의 1과 2위치에 이중결합인 것을 특징으로 하는 화합물.
  20. 제19항에 있어서, X는
    인 것을 특징으로 하는 화합물.
  21. 제20항에 있어서, R3과 R4는 메톡시이고, R5는 수소인 것을 특징으로 하는 화합물.
  22. 제21항에 있어서, R3과 2-메톡시이고 R4는 4-메톡시인 것을 특징으로 하는 화합물.
  23. 제1항에 따른 화합물의 치료요법적 효과량을 동물에 투여하는 것으로 구성된 퇴행성 신경질환의 치료방법.
  24. 제23항에 있어서, 동물은 사람이고, 신경성 질환은 알즈마이어 질환과 파킨슨 질환에서 선택되는 것을 특징으로 하는 방법.
  25. 제1항에 따른 화합물의 치료요법적 효과량과 제약학적 수용가능한 담체로 구성되고, 동물의 퇴행성 신경질환을 치료하는데 적합한 것을 특징으로 하는 제약학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950700698A 1992-08-31 1993-08-31 신경계의 퇴행성 질환의 치료에 유용한 아나바세인 유도체 KR100272614B1 (ko)

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US93842792A 1992-08-31 1992-08-31
US938427 1992-08-31
PCT/US1993/008192 WO1994005288A1 (en) 1992-08-31 1993-08-31 Anabaseine derivatives useful in the treatment of degenerative diseases of the nervous system

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KR100272614B1 KR100272614B1 (ko) 2000-11-15

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EP (1) EP0659078B1 (ko)
JP (1) JP3034953B2 (ko)
KR (1) KR100272614B1 (ko)
AT (1) ATE230989T1 (ko)
AU (1) AU674541B2 (ko)
CA (1) CA2142610C (ko)
DE (1) DE69332641T2 (ko)
WO (1) WO1994005288A1 (ko)

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KR100272614B1 (ko) 2000-11-15
AU674541B2 (en) 1997-01-02
CA2142610C (en) 2003-09-16
CA2142610A1 (en) 1994-03-17
JPH08509458A (ja) 1996-10-08
US5741802A (en) 1998-04-21
DE69332641D1 (de) 2003-02-20
AU5097993A (en) 1994-03-29
DE69332641T2 (de) 2003-11-27
EP0659078A1 (en) 1995-06-28
ATE230989T1 (de) 2003-02-15
WO1994005288A1 (en) 1994-03-17
JP3034953B2 (ja) 2000-04-17
EP0659078B1 (en) 2003-01-15

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