KR890008139A - 아자사이클릭 화합물 및 이의 제조방법 및 용도 - Google Patents

아자사이클릭 화합물 및 이의 제조방법 및 용도 Download PDF

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KR890008139A
KR890008139A KR1019880014814A KR880014814A KR890008139A KR 890008139 A KR890008139 A KR 890008139A KR 1019880014814 A KR1019880014814 A KR 1019880014814A KR 880014814 A KR880014814 A KR 880014814A KR 890008139 A KR890008139 A KR 890008139A
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KR1019880014814A
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닐센 론
웨트젠 프랑크
에이치. 올레센 프레벤
사우어베르그 페르
더블유 킨들러 옌스
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외르겐 부스 라센
에스/에스 페로산
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Priority claimed from DK595287A external-priority patent/DK595287D0/da
Priority claimed from DK687087A external-priority patent/DK687087D0/da
Priority claimed from DK110288A external-priority patent/DK110288D0/da
Application filed by 외르겐 부스 라센, 에스/에스 페로산 filed Critical 외르겐 부스 라센
Publication of KR890008139A publication Critical patent/KR890008139A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals 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
    • 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

Abstract

내용 없음

Description

아자사이클릭 화합물 및 이의 제조방법 및 용도
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. 다음 화합물로 이루어지는 그룹으로부터 선택되는 일반식(I)의 아자사이클릭 화합물.
    상기식에서, R1은 H 또는 C1-6알킬이고,
    -CH=N-O-R″′ 또는
    (여기에서 R'는 C3-8-알킬, 사이클로프로필, C4-8사이클로알킬, 벤질(이는 치환될 수 있다), 또는 C1-4-알콕시-C1-4-알킬이고, R″는 H 또는 C1-8-알킬 또는 C1-6-알콕시 또는 C1-4-알콕시-C1-4-알킬 또는 아릴이고, R″'는 H 또는 C1-6-알킬 또는 C4-8-사이클로알킬이다)이고, R4는 H, C1-8-알킬, 또는 CI이고,
    단, 일반식(I)의 화합물이인 경우
    R3는또는
    (여기에서, R'는 C3-8-알킬, 사이클로프로필 또는 C1-3-알콕시메틸이다)가 아니고, 또한 -CH=N-OR″'(여기에서, R″'는 H 또는 C1-6-알킬이다)가 아니다.
  2. 제1항에 있어서, 2-(3-사이클로프로필-1,2,4-옥사디아졸-5-일)-8-메틸-8아자비사이클로[3.2.1]옥트-2-엔인 화합물.
  3. 제1항에 있어서, 3-(5-프로필-1,2,4-옥사디아졸-3-일)-2,3-디데하이드로퀴누클리딘인 화합물
  4. 제1항에 있어서, 3-(3-부틸-1,2,4-옥사디아졸-5-일)-퀴누클리딘인 화합물.
  5. 제1항에 있어서, 3-(5-메톡시메틸-3-이속사졸릴)-1,2,5,6-테트라하이드로피리딘인 화합물.
  6. a)일반식(II)의 화합물로 이루어지는 그룹으로 부터 선택되는 화합물의 반응성 유도체를 일반식(III)의 화합물과 반응시켜 R3이
    (여기에서, R'는 제1항에서 정의한 바와 같다)인 일반식(I)의 화합물을 생성시키거나, b)일반식(IV)의 화합물로 이루어지는 그룹으로 부터 선택되는 화합물을 NH2OH와 반응시키고 이렇게 하여 생성된 화합물을 R'-COCI 또는 (R'CO)2O (여기에서 R1는 제1항에서 정의한 바와 같다)와 반응시켜 R3이
    (여기에서, R1는 제1항에서 정의한 바와 같다)인 일반식(I)의 화합물을 생성시키거나, c)일반식(V)의 화합물로 이루어지는 그룹으로 부터 선택되는 화합물을 알켄, 알킨 또는 이의 등가물과 반응시켜 R3이
    (여기에서, R″는 제1항에서 정의한 바와 같다)인 일반식(I)의 화합물을 생성시키거나, d)일반식(VI)의 화합물로 이루어지는 그룹으로 부터 선택되는 화합물을 일반식(VII)의 화합물과 반응시켜 R3이 -CH=N-O-R″(여기에서, R″'는 제1항에서 정의한바와 같다)인 일반식(I)의 화합물을 생성시키거나, e)일반식(VIII)의 화합물로 이루어지는 그룹으로 부터 선택되는 화합물을 일반식 CH3-1,4-페니렌(여기에서, R″'는 제1항에서 정의한 바와 같다)의 화합물과 반응시켜 R3이(여기에서, R″'는 제1항에서 정의한 바와 같다)인 일반식(I)의 화합물을 생성시키거나, f)피리딘-3-카브알데히드를 일반식 CH3-1, 4-페닐렌(여기에서, R″'는 제1항에서 정의한 바와 같다)의 화합물과 반응시킨 다음 R1-할로겐(여기에서, R1는 제1항에서 정의한 바와 같다)과 반응시키고 이렇게 하여 생성된 화합물을 NaBH4와 반응시켜 일반식(I-1)의 화합물을 생성시키거나, g)3-아세틸피리딘을 일반식의 화합물(여기에서, R"는 제1항에서 정의한 바와 같다)과 반응시킨 다음 NH2-OSO3H 및 R1-할로겐(여기에서, R1는 제1항에서 정의한 바와 같다)과 반응시키고 이렇게 하여 생성된 화합물을 NaBH4와 반응시켜 일반식(I-2)의 화합물을 생성시키거나, h)3-에티닐피리딘을 일반식 R″CN+O-의 화합물(여기에서, R″는 제1항에서 정의한 바와 같다)과 반응시킨 다음 R'는 제1항에서 정의한 바와 같다)과 반응시키고 이렇게 하여 생성된 화합물을 NaBH4와 반응시켜 일반식(I-2)의 화합물을 생성시킴을 특징으로 하여 제1항의 화합물을 제조하는 방법.
    상기식에서 R1, R4, R1, R″, R″' 및는 제1항에서 정의한 바와 같다.
  7. 약제학적으로 허용되는 담체 또는 희석제와 함께 포유동물의 전뇌 및 해마를 자극시키거나 알쯔하이머병을 치료하기에 유효한 양의 제1항의 화합물을 함유함을 특징으로 하는, 인간을 포함하는 포유동물의 전뇌 및 해마의 인지 기능의 자극 및 알쯔하이머병 치료용으로 적합한 약제학적 조성물.
  8. 제4항에 있어서, 1내지 100mg의 활성 화합물을 함유하는 경구투여 단위형인 약제학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880014814A 1987-11-13 1988-11-11 아자사이클릭 화합물 및 이의 제조방법 및 용도 KR890008139A (ko)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DK?5952/87? 1987-11-13
DK595287A DK595287D0 (da) 1987-11-13 1987-11-13 Azabicykliske forbindelser, deres fremstilling og anvendelse
DK687087A DK687087D0 (da) 1987-12-28 1987-12-28 Azacycliske forbindelser, deres fremstilling og anvendelse
DK?6870/87? 1987-12-28
DK110288A DK110288D0 (da) 1988-03-02 1988-03-02 Azacykliske forbindelser, deres fremstilling og anvendelse
DK?1102/88? 1988-03-02

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KR890008139A true KR890008139A (ko) 1989-07-10

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US (2) US5262427A (ko)
EP (1) EP0316718B1 (ko)
JP (1) JP2831362B2 (ko)
KR (1) KR890008139A (ko)
AU (1) AU619770B2 (ko)
CA (1) CA1340943C (ko)
DE (1) DE3884140T2 (ko)
ES (1) ES2059469T3 (ko)
FI (1) FI95799C (ko)
IE (1) IE63906B1 (ko)
IL (1) IL88156A (ko)
NO (1) NO171787C (ko)
NZ (1) NZ226936A (ko)
PH (1) PH25289A (ko)
PT (1) PT88993B (ko)

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IL88156A0 (en) 1989-06-30
US5356912A (en) 1994-10-18
JPH01153688A (ja) 1989-06-15
EP0316718B1 (en) 1993-09-15
FI95799B (fi) 1995-12-15
PT88993A (pt) 1989-11-30
DE3884140D1 (de) 1993-10-21
JP2831362B2 (ja) 1998-12-02
NO885052L (no) 1989-05-16
ES2059469T3 (es) 1994-11-16
AU619770B2 (en) 1992-02-06
PH25289A (en) 1991-04-30
NO171787B (no) 1993-01-25
AU2460888A (en) 1989-05-18
IE883208L (en) 1989-05-13
NO171787C (no) 1993-05-05
CA1340943C (en) 2000-04-04
NO885052D0 (no) 1988-11-11
IL88156A (en) 1997-02-18
EP0316718A3 (en) 1989-12-20
EP0316718A2 (en) 1989-05-24
PT88993B (pt) 1993-05-31
US5262427A (en) 1993-11-16
FI95799C (fi) 1996-03-25
NZ226936A (en) 1991-02-26
IE63906B1 (en) 1995-06-14
FI885223A0 (fi) 1988-11-11
FI885223A (fi) 1989-05-14

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