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

아자사이클릭 화합물 및 이의 제조방법 및 용도 Download PDF

Info

Publication number
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
Authority
KR
South Korea
Prior art keywords
compound
formula
alkyl
compounds
group
Prior art date
Application number
KR1019880014814A
Other languages
English (en)
Inventor
닐센 론
웨트젠 프랑크
에이치. 올레센 프레벤
사우어베르그 페르
더블유 킨들러 옌스
Original Assignee
외르겐 부스 라센
에스/에스 페로산
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Psychiatry (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

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
DK595287A DK595287D0 (da) 1987-11-13 1987-11-13 Azabicykliske forbindelser, deres fremstilling og anvendelse
DK?5952/87? 1987-11-13
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

Publications (1)

Publication Number Publication Date
KR890008139A true KR890008139A (ko) 1989-07-10

Family

ID=27221113

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019880014814A KR890008139A (ko) 1987-11-13 1988-11-11 아자사이클릭 화합물 및 이의 제조방법 및 용도

Country Status (15)

Country Link
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)

Families Citing this family (79)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0261763B1 (en) * 1986-06-27 1994-02-09 Beecham Group Plc Novel bridged bicyclic N-heterocycles
GB8714789D0 (en) * 1987-06-24 1987-07-29 Lundbeck & Co As H Heterocyclic compounds
IE63906B1 (en) * 1987-11-13 1995-06-14 Novo Nordisk As Azabicyclic compounds and their preparation and use
EP0322182A3 (en) * 1987-12-22 1992-01-02 Beecham Group Plc Azabicyclic compounds, process for their preparation and pharmaceutical compositions containing them
IL88846A0 (en) * 1988-01-08 1989-07-31 Merck Sharp & Dohme Lipophilic oxadiazoles,their preparation and pharmaceutical compositions containing them
EP0338723B1 (en) * 1988-04-15 1993-08-04 Beecham Group Plc Novel compounds
CA2000041A1 (en) * 1988-10-13 1990-04-13 Barry S. Orlek Compounds
DE8817121U1 (de) * 1988-11-22 1993-02-04 Boehringer Ingelheim Kg, 55218 Ingelheim Neue Quinuclidine
GB8830226D0 (en) * 1988-12-23 1989-02-22 Beecham Group Plc Novel compounds
US4937239A (en) * 1989-02-13 1990-06-26 Warner-Lambert Company Azabicycloalkane oxime & azabicycloalkene oxime muscarinic agents
US5043345A (en) * 1989-02-22 1991-08-27 Novo Nordisk A/S Piperidine compounds and their preparation and use
DK0392803T3 (da) * 1989-04-13 2004-10-18 Beecham Group Plc Hidtil ukendte forbindelser
ATE153024T1 (de) * 1989-08-16 1997-05-15 Beecham Group Plc Azabicyclische verbindungen
EP0427390B1 (en) * 1989-10-07 1996-03-27 Beecham Group Plc Azabicyclic compounds, process and intermediates for their preparation and pharmaceutical compositions containing them
DK40890D0 (da) * 1990-02-16 1990-02-16 Ferrosan As Substituerede urinstofforbindelser, deres fremstilling og anvendelse
EP0459568A3 (en) * 1990-05-31 1992-09-30 Merck Sharp & Dohme Ltd. Substituted oxadiazoles and thiadiazoles for use in the treatment of glaucoma and novel compounds having such use
US5376668A (en) * 1990-08-21 1994-12-27 Novo Nordisk A/S Heterocyclic compounds
USRE35822E (en) * 1990-08-21 1998-06-09 Novo Nordisk A/S Heterocyclic compounds
US5527813A (en) * 1990-08-21 1996-06-18 Novo Nordisk A/S Heterocyclic compounds and their preparation and use
DK198390D0 (da) * 1990-08-21 1990-08-21 Novo Nordisk As Heterocykliske forbindelser, deres fremstilling og anvendelse
US5418240A (en) * 1990-08-21 1995-05-23 Novo Nordisk A/S Heterocyclic compounds and their preparation and use
DK198490D0 (da) * 1990-08-21 1990-08-21 Novo Nordisk As Heterocykliske forbindelser, deres fremstilling og anvendelse
DK198590D0 (da) * 1990-08-21 1990-08-21 Novo Nordisk As Heterocykliske forbindelser, deres fremstilling og anvendelse
WO1992003435A1 (en) * 1990-08-24 1992-03-05 Beecham Group Plc Azabicyclic compounds, process and intermediates for their preparation and pharmaceutical compositions containing them
GB9019095D0 (en) * 1990-09-01 1990-10-17 Beecham Group Plc Novel compounds
EP0552213A1 (en) * 1990-10-12 1993-07-28 Beecham Group Plc 1,2,5,6-tetrahydropyridine oxime derivatives
DE69129203T2 (de) * 1990-11-29 1998-12-03 Allergan Inc Verwendung von pyridine derivate zur behandlung der okulären hypertomie
IE922270A1 (en) * 1991-07-26 1993-01-27 Akzo Nv Pyrazole derivatives
US5641791A (en) * 1991-08-13 1997-06-24 Novo Nordisk A.S Heterocyclic compounds and their preparation and use
GB9122988D0 (en) * 1991-10-30 1991-12-18 Ici Plc Heterocyclic compounds
GB9127279D0 (en) * 1991-12-23 1992-02-19 Ici Plc Heterocyclic derivatives
EP0619814A1 (en) * 1991-12-31 1994-10-19 Fujisawa Pharmaceutical Co., Ltd. Oxadiazole derivatives having acetylcholinesterase-inhibitory and muscarinic agonist activity
WO1993014089A1 (en) * 1992-01-13 1993-07-22 Novo Nordisk A/S Heterocyclic compounds and their preparation and use
US5212188A (en) * 1992-03-02 1993-05-18 R. J. Reynolds Tabacco Company Method for treatment of neurodegenerative diseases
US5242934A (en) * 1992-03-02 1993-09-07 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
US5242935A (en) * 1992-03-06 1993-09-07 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
US5227385A (en) * 1992-03-13 1993-07-13 Wake Forest University Method for treatment of neurodegenerative diseases
US5288872A (en) * 1992-03-13 1994-02-22 Wake Forest University Compounds for treatment of neurodegenerative diseases
US5330994A (en) * 1992-03-24 1994-07-19 Warner-Lambert Company Tetrahydropyridine isoxazoline derivatives
JPH06508377A (ja) * 1992-04-10 1994-09-22 ゼネカ　リミテッド ヘテロ環式化合物
US5187169A (en) * 1992-04-10 1993-02-16 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
US5276043A (en) * 1992-04-10 1994-01-04 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
US5214060A (en) * 1992-04-10 1993-05-25 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
SE9201478D0 (sv) * 1992-05-11 1992-05-11 Kabi Pharmacia Ab Heteroaromatic quinuclidinenes, their use and preparation
US5232932A (en) * 1992-05-21 1993-08-03 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
US5232933A (en) * 1992-05-21 1993-08-03 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
GB9211796D0 (en) * 1992-06-04 1992-07-15 Ici Plc Heterocyclic derivatives
US5248690A (en) * 1992-07-07 1993-09-28 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
US5242916A (en) * 1992-07-07 1993-09-07 R. J. Reynolds Tobacco Company Method for treatment of neurodegenerative diseases
GB9216721D0 (en) * 1992-08-06 1992-09-23 Ici Plc Therapeutic heterocyclic derivatives
GB9218334D0 (en) * 1992-08-28 1992-10-14 Ici Plc Heterocyclic compounds
ES2133416T3 (es) * 1992-10-23 1999-09-16 Merck Sharp & Dohme Ligandos de subtipos de receptores de dopamina.
GB9226573D0 (en) * 1992-12-21 1993-02-17 Ici Plc Heterocyclic compounds
AU672644B2 (en) * 1992-12-23 1996-10-10 Neurosearch A/S Aryl substituted heterocyclic compounds
AU672052B2 (en) * 1992-12-23 1996-09-19 Neurosearch A/S Antidepressant and antiparkinsonian compounds
AU671163B2 (en) * 1992-12-23 1996-08-15 Neurosearch A/S Alkyl substituted heterocyclic compounds
US5612351A (en) * 1994-11-08 1997-03-18 Novo Nordisk A/S Method of treating urinary bladder dysfunctions
US5668148A (en) * 1995-04-20 1997-09-16 Merck & Co., Inc. Alpha1a adrenergic receptor antagonists
US5583140A (en) * 1995-05-17 1996-12-10 Bencherif; Merouane Pharmaceutical compositions for the treatment of central nervous system disorders
US5733912A (en) * 1997-02-19 1998-03-31 Abbott Laboratories 7A-heterocycle substituted hexahydro-1H-pyrrolizine compounds useful in controlling chemical synaptic transmission
US6093724A (en) * 1998-08-18 2000-07-25 Ucb, S.A. Muscarinic agonists and antagonists
US6107313A (en) * 1998-10-02 2000-08-22 Combichem, Inc. Dopamine receptor antagonists
NZ533158A (en) * 2001-11-19 2006-09-29 Elan Pharm Inc 3,4-Disubstituted, 3,5-disubstituted and 3,4,5-substituted piperidines and piperazines
KR100448002B1 (ko) * 2002-02-01 2004-09-13 한국과학기술연구원 신규한 퀴누클리딘 화합물 및 그 제조방법
WO2006065217A1 (en) * 2004-12-16 2006-06-22 Astrazeneca Ab Nicotinic acetycholine receptor ligands
EP2258358A3 (en) 2005-08-26 2011-09-07 Braincells, Inc. Neurogenesis with acetylcholinesterase inhibitor
EP2275095A3 (en) 2005-08-26 2011-08-17 Braincells, Inc. Neurogenesis by muscarinic receptor modulation
JP2009512711A (ja) 2005-10-21 2009-03-26 ブレインセルス，インコーポレイティド Ｐｄｅ阻害による神経新生の調節
CA2625210A1 (en) 2005-10-31 2007-05-10 Braincells, Inc. Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
AU2007249399A1 (en) 2006-05-09 2007-11-22 Braincells, Inc. Neurogenesis by modulating angiotensin
JP2009536667A (ja) 2006-05-09 2009-10-15 ブレインセルス，インコーポレイティド ５ｈｔ受容体介在性の神経新生
KR20090064418A (ko) * 2006-09-08 2009-06-18 브레인셀즈 인코퍼레이션 4-아실아미노피리딘 유도체 포함 조합물
US20100184806A1 (en) 2006-09-19 2010-07-22 Braincells, Inc. Modulation of neurogenesis by ppar agents
US8084473B2 (en) 2007-04-24 2011-12-27 Solvay Pharmaceuticals B.V. Heterocyclic compounds with affinity to muscarinic receptors
EP2150543A2 (en) * 2007-04-24 2010-02-10 Solvay Pharmaceuticals B.V. Heterocyclic compounds with affinity to muscarinic receptors
EP2296471A4 (en) 2008-05-15 2012-03-14 Univ Toledo MUSCARIC ACID AGONISTS AS COGNITIVE ENHANCERS
WO2010099217A1 (en) 2009-02-25 2010-09-02 Braincells, Inc. Modulation of neurogenesis using d-cycloserine combinations
WO2012149524A1 (en) 2011-04-29 2012-11-01 The University Of Toledo Muscarinic agonists as enhancers of working memory and cognitive flexibility

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL132134C (ko) * 1963-03-22
US4144343A (en) * 1978-01-04 1979-03-13 Merck & Co., Inc. Heterocycle substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines
US4518601A (en) * 1982-06-16 1985-05-21 Ciba Geigy Corporation 2-(3-Pyridyl)-1,3,4-oxadiazoles and use thereof in pest control
IL81610A (en) * 1986-02-27 1990-12-23 Roussel Uclaf Derivatives of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime,their preparation and pharmaceutical compositions containing them
NZ219646A (en) * 1986-03-27 1990-10-26 Merck Sharp & Dohme Oxadiazole derivatives of azacyclics for treating cns disorders
GB8610432D0 (en) * 1986-04-29 1986-06-04 Akzo Nv Amino-thiazole & oxazole derivatives
EP0261763B1 (en) * 1986-06-27 1994-02-09 Beecham Group Plc Novel bridged bicyclic N-heterocycles
IL83275A (en) * 1986-09-08 1994-02-27 Novo Nordisk As Compounds 1,2, 4-Oxadiazolyl Pipridine Transformed, their preparation and pharmaceutical preparations containing them
US4786648A (en) * 1986-12-08 1988-11-22 Warner-Lambert Company O-substituted tetrahydropyridine oxime cholinergic agents
US4710508A (en) * 1986-12-08 1987-12-01 Warner-Lambert Company O-substituted tetrahydropyridine oxime cholinergic agents
GB8714789D0 (en) * 1987-06-24 1987-07-29 Lundbeck & Co As H Heterocyclic compounds
GB8717446D0 (en) * 1987-07-23 1987-08-26 Merck Sharp & Dohme Chemical compounds
EP0307141B1 (en) * 1987-09-10 1993-01-13 MERCK SHARP &amp; DOHME LTD. Oxazoles and thiazoles for the treatment of senile dementia
IE63906B1 (en) * 1987-11-13 1995-06-14 Novo Nordisk As Azabicyclic compounds and their preparation and use
IT1233446B (it) * 1987-12-30 1992-04-01 Roussel Maestretti Spa Derivati della 3 piperidinocarbaldeide ossima, loro procedimento di preparazione e loro applicazione come farmaci
IL88846A0 (en) * 1988-01-08 1989-07-31 Merck Sharp & Dohme Lipophilic oxadiazoles,their preparation and pharmaceutical compositions containing them
US4937239A (en) * 1989-02-13 1990-06-26 Warner-Lambert Company Azabicycloalkane oxime & azabicycloalkene oxime muscarinic agents

Also Published As

Publication number Publication date
IE883208L (en) 1989-05-13
DE3884140D1 (de) 1993-10-21
EP0316718A3 (en) 1989-12-20
PH25289A (en) 1991-04-30
FI95799C (fi) 1996-03-25
US5262427A (en) 1993-11-16
PT88993B (pt) 1993-05-31
FI885223A (fi) 1989-05-14
NO885052D0 (no) 1988-11-11
JPH01153688A (ja) 1989-06-15
PT88993A (pt) 1989-11-30
FI885223A0 (fi) 1988-11-11
IE63906B1 (en) 1995-06-14
NO171787C (no) 1993-05-05
JP2831362B2 (ja) 1998-12-02
NZ226936A (en) 1991-02-26
AU2460888A (en) 1989-05-18
DE3884140T2 (de) 1994-01-13
IL88156A0 (en) 1989-06-30
FI95799B (fi) 1995-12-15
NO171787B (no) 1993-01-25
ES2059469T3 (es) 1994-11-16
EP0316718A2 (en) 1989-05-24
EP0316718B1 (en) 1993-09-15
CA1340943C (en) 2000-04-04
NO885052L (no) 1989-05-16
US5356912A (en) 1994-10-18
IL88156A (en) 1997-02-18
AU619770B2 (en) 1992-02-06

Similar Documents

Publication Publication Date Title
KR890008139A (ko) 아자사이클릭 화합물 및 이의 제조방법 및 용도
KR880003939A (ko) 피페리딘 화합물과 이의 제조방법 및 용도
KR900018087A (ko) 옥사디아졸 및 이의염, 치매를 치료하기 위한 이의 용도, 이의 제조방법 및 제제
PT94543A (pt) Processo para a preparacao de trp-phe-e fenetilaminas alfa-substituidas por ciclo-alquilo e poli-ciclo-alquilo n-substituidos
KR940013555A (ko) 알킬 치환된 헤테로사이클릭 화합물
JP2002356472A5 (ko)
KR900016202A (ko) 2개의 헤테로원자를 갖는 5원환을 포함하는 스피로사이클릭 화합물
JPH06502144A (ja) 新規化合物
KR900001693A (ko) 아자사이클릭 화합물, 이의 제조방법 및 이의 용도
JP2000212163A (ja) アザシクロオキシムおよびアミンコリン作働剤
KR900007842A (ko) 조성물 및 화합물
KR940014332A (ko) 레트로비루스성 프로테아제 효소의 저해제로서 유용하고 항-hiv제로서 작용하는 신규한 화합물 및 이들의 생산 방법
DE69429570D1 (de) Galanthamin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikamente
HUT52376A (en) Process for producing pharmaceutical compositions comprising 3-substituted-2-oxindole-1-carboxamide derivatives as active ingredient
US5318978A (en) Azabicyclo oxime and amine cholinergic agents and methods of treatment
JP2005527495A (ja) 治療化合物
KR910000647A (ko) 나프틸아미노-및 나프틸옥시- 피리딘아민 및 관련된 화합물, 이의 제조방법 및 이의 피부소염제로서의 용도
CA2308867A1 (fr) Nouveaux composes pyridiniques ou piperidiniques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2441617A1 (fr) Nouveaux derives de s-triazine, leur procede de preparation et compositions pharmaceutiques les contenant
KR880001596A (ko) 디하이드로피리딘 화합물-함유 뇌기능이상 치료제
KR950017996A (ko) 에피-에피바티딘 유도체
RU2005136434A (ru) 7-азаиндолы и их применение в качестве лекарственых средств
KR930017882A (ko) 아미노 벤조산 유도체
NO157297C (no) Analogifremgangsmaate ved fremstilling av terapeutisk aktive 7alfa-acylthio-15,16-methylen-3-oxo-17alfa-pregna-1,4-dien-21,17-carbolactoner.
KR910000652A (ko) (1,2,3,4-테트라하이드로-9-아크리딘이미노) 사이클로헥산 카복실산 및 관련 화합물, 이들의 제조방법 및 약제로서의 용도

Legal Events

Date Code Title Description
WITN Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid