KR960702820A - 방향족 아세틸콜린에스테라제 억제제 (Aromatic acetylcholinesterase inhibitors) - Google Patents

방향족 아세틸콜린에스테라제 억제제 (Aromatic acetylcholinesterase inhibitors)

Info

Publication number
KR960702820A
KR960702820A KR1019950705440A KR19950705440A KR960702820A KR 960702820 A KR960702820 A KR 960702820A KR 1019950705440 A KR1019950705440 A KR 1019950705440A KR 19950705440 A KR19950705440 A KR 19950705440A KR 960702820 A KR960702820 A KR 960702820A
Authority
KR
South Korea
Prior art keywords
trifluoro
phenyl
compound according
alkyl
independently
Prior art date
Application number
KR1019950705440A
Other languages
English (en)
Inventor
콜라르 장-노엘
호른스페르제 장-마리
쉬를렝 다니엘
Original Assignee
스티븐 엘. 네스빗
메렐 파마슈티칼즈 인코포레이티드
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
Application filed by 스티븐 엘. 네스빗, 메렐 파마슈티칼즈 인코포레이티드 filed Critical 스티븐 엘. 네스빗
Publication of KR960702820A publication Critical patent/KR960702820A/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • 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
    • A61K31/12—Ketones
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

하기 일반식(I)의 화합물, 이의 입체이상체 및 약제학적으로 허용되는 이의 염은 콜린에스테라제 억제 활성을 지니며, 퇴행성 치매의 치료시에 사용될 수 있다.
상기 식에서, Z 및 Z′는 각각 독립적으로 H 또는 F이고; Q는또는이며; X는 H, Br, Cl, F 또는 CF3이고; Y는 H, Br, Cl, F, OH, OR5, OC(O)R4, N3, CN, NO2, SO3H, CO2R4, NH2, NHR9, NR9R′9, C(R6)(R7)(V′R8) 또는 C(O)R7이며, 단, Z 및 Z′가 모두 F일 때, Y는 H 또는 F이며, V 및 V′는 각각 독립적으로 CH2또는 0이고; R1은 H 또는 CH3이며; R2,R9및 R′9는 각각 독립적으로 (C1-6)알킬이거나; R2및 V-R3는 이에 결합된 탄소 원자와 함께 3 내지 6원환을 형성하고; R3,R6,R7및 R8은 각각 독립적으로 H, (C1-6)알킬 또는 (C3-6) 사이클로알킬이고; R4는 H, (C1-10)알킬, (C0-4)알킬렌 아릴 또는 (C3-8)사이클로알킬이고; C5는 (C1-10)알킬, 벤질, 펜에틸 또는 (C3-6)사이클로알킬이다.

Description

방향족 아세틸콜린에스테라제 억제제(Aromatic acetylcholinesterase inhibitors)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. 약제학적 활성 화합물로서 사용하기 위한 하기 일반식(I)의 화합물, 이의 입체 이성체 및 약제학적으로 허용되는 이의 염.
    상기 식에서, Z 및 Z′는 각각 독립적으로 H 또는 F이고; Q는또는이며; X는 H, Br, Cl, F 또는 CF3이고; Y는 H, Br, Cl, F, OH, OR5, OC(O)R4, N3, CN, NO2, SO3H, CO2R4, NH2, NR9R′9, C(R6)(R7)(V′R8) 또는 C(O)R7이며, 단, Z 및 Z′가 모두 F일 때, Y는 H 또는 F이며, V 및 V′는 각각 독립적으로 CH2또는 0이고; R1은 H 또는 CH3이며; R2,R9및 R′9는 각각 독립적으로 (C1-6)알킬이고; R3,R6,R7및 R8은 각각 독립적으로 H, (C1-6)알킬 또는 (C3-6) 사이클로알킬이거나; R2및 V-R3는 이에 결합된 탄소 원자와 함께 3 내지 6원환을 형성하고; R4는 H, (C1-10)알킬, (C0-4)알킬렌 아릴 또는 (C3-8)사이클로알킬이고; C5는 (C1-10)알킬, 벤질, 펜에틸 또는 (C3-6)사이클로알킬이다.
  2. 제1항에 있어서, Q가 C(O)인 화합물의 용도.
  3. 제1항에 있어서, X가 F인 화합물의 용도.
  4. 제1항에 있어서, Z,Z′ 및 Y가 각각 수소인 화합물의 용도.
  5. 제1항에 있어서, R1,R2, V 및 R3가 각각 메틸, 메틸, 메틸렌 및 수소인 화합물의 용도.
  6. 제1항에 있어서, 2,2,2-트리플루오로-1-(3-3급-부틸)페닐 에탄온; 2,2,2-트리플루오로-1-(3-3급-부틸)페닐 에탄올; [2,2,2-트리플루오로-1-(3-3급-부틸)페닐]에틸 아세테이트; 2,2,2-트리플루오로-1-[3-(2-프로필 메틸 에테르)]페닐; 2,2,2-트리플루오로-1-[3-(2-프로판올)]페닐 에탄온; 2,2,2-트리플루오로-1-[2-플루오로-5-(1-디에틸에테르)]페닐 에탄온; 2,2,2-트리플루오로-1-(2-플루오로-3-이소프로필)페닐 에탄온; 또는 2,2,2-트리플루오로-1-[2-플루오로-3-(N,N-디메틸아미노)-5-(1-디에틸에테르)]페닐 에탄온인 화합물의 용도.
  7. 퇴행성 치매의 치료시의 제1항에 따른 화합물의 용도.
  8. 퇴행성 치매의 치료를 위한 약제학적 조성물을 제조하기 위한, 임의로 약제학적으로 허용되는 담체와 배합된 제1항에 따른 화합물의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950705440A 1993-06-04 1994-05-05 방향족 아세틸콜린에스테라제 억제제 (Aromatic acetylcholinesterase inhibitors) KR960702820A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP93401431A EP0627400A1 (en) 1993-06-04 1993-06-04 Aromatic acetylcholinesterase inhibitors
EP93401431.7 1993-06-04
PCT/US1994/004957 WO1994029255A1 (en) 1993-06-04 1994-05-05 Aromatic acetylcholinesterase inhibitors

Publications (1)

Publication Number Publication Date
KR960702820A true KR960702820A (ko) 1996-05-23

Family

ID=8214719

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019950705440A KR960702820A (ko) 1993-06-04 1994-05-05 방향족 아세틸콜린에스테라제 억제제 (Aromatic acetylcholinesterase inhibitors)

Country Status (19)

Country Link
US (1) US5663448A (ko)
EP (2) EP0627400A1 (ko)
JP (1) JP3735372B2 (ko)
KR (1) KR960702820A (ko)
CN (1) CN1124953A (ko)
AT (1) ATE174895T1 (ko)
AU (1) AU676578B2 (ko)
CA (1) CA2164303C (ko)
DE (1) DE69415522T2 (ko)
DK (1) DK0701546T3 (ko)
ES (1) ES2127396T3 (ko)
FI (1) FI955795A (ko)
HU (1) HUT73484A (ko)
IL (1) IL109863A (ko)
NO (1) NO306058B1 (ko)
NZ (1) NZ267221A (ko)
TW (1) TW385247B (ko)
WO (1) WO1994029255A1 (ko)
ZA (1) ZA943787B (ko)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5804560A (en) * 1995-01-06 1998-09-08 Sibia Neurosciences, Inc. Peptide and peptide analog protease inhibitors
US6017887A (en) * 1995-01-06 2000-01-25 Sibia Neurosciences, Inc. Peptide, peptide analog and amino acid analog protease inhibitors
US6218383B1 (en) 1998-08-07 2001-04-17 Targacept, Inc. Pharmaceutical compositions for the prevention and treatment of central nervous system disorders
JP2008525439A (ja) * 2004-12-23 2008-07-17 ボイジャー・ファーマシューティカル・コーポレーション アルツハイマー病の治療のための酢酸ロイプロリド及びアセチルコリンエステラーゼインヒビターまたはｎｍｄａレセプターアゴニスト
US20060194723A1 (en) * 2005-02-28 2006-08-31 Rabinoff Michael D Novel medication treatment and delivery strategies for Alzheimer's Disease, other disorders with memory impairment, and possible treatment strategies for memory improvement
WO2008055945A1 (en) 2006-11-09 2008-05-15 Probiodrug Ag 3-hydr0xy-1,5-dihydr0-pyrr0l-2-one derivatives as inhibitors of glutaminyl cyclase for the treatment of ulcer, cancer and other diseases
ATE554085T1 (de) 2006-11-30 2012-05-15 Probiodrug Ag Neue inhibitoren von glutaminylcyclase
EP2481408A3 (en) 2007-03-01 2013-01-09 Probiodrug AG New use of glutaminyl cyclase inhibitors
EP2865670B1 (en) 2007-04-18 2017-01-11 Probiodrug AG Thiourea derivatives as glutaminyl cyclase inhibitors
EP2475428B1 (en) 2009-09-11 2015-07-01 Probiodrug AG Heterocylcic derivatives as inhibitors of glutaminyl cyclase
US20110212928A1 (en) 2010-02-09 2011-09-01 The Johns Hopkins University Methods and compositions for improving cognitive function
ES2586231T3 (es) 2010-03-03 2016-10-13 Probiodrug Ag Inhibidores de glutaminil ciclasa
CN102791704B (zh) 2010-03-10 2015-11-25 前体生物药物股份公司 谷氨酰胺酰环化酶(qc, ec 2.3.2.5)的杂环抑制剂
EP2560953B1 (en) 2010-04-21 2016-01-06 Probiodrug AG Inhibitors of glutaminyl cyclase
US8530670B2 (en) 2011-03-16 2013-09-10 Probiodrug Ag Inhibitors
CN102826985B (zh) * 2012-09-18 2015-08-19 厦门大学 一种1-(3,4,5-三羟基)苯基-1-烷基酮的制备方法
US20140206667A1 (en) 2012-11-14 2014-07-24 Michela Gallagher Methods and compositions for treating schizophrenia
US10806717B2 (en) 2013-03-15 2020-10-20 The Johns Hopkins University Methods and compositions for improving cognitive function
US11160785B2 (en) 2013-03-15 2021-11-02 Agenebio Inc. Methods and compositions for improving cognitive function
JP6899043B2 (ja) 2015-05-22 2021-07-07 エージンバイオ， インコーポレイテッド レベチラセタムの持続放出性医薬組成物
PL3461819T3 (pl) 2017-09-29 2020-11-30 Probiodrug Ag Inhibitory cyklazy glutaminylowej

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU884568A3 (ru) * 1977-10-07 1981-11-23 Сьянс Юньон Э Ко.,Сосьете Франсэз Де Решерш Медикаль(Фирма) Способ получени (арилалкил) алкановых кислот
US4835099A (en) * 1986-11-20 1989-05-30 Becton, Dickinson And Company Signal enhancement in immunoassay by modulation of enzymatic catalysis
DE3725941A1 (de) * 1987-08-05 1989-02-16 Hoechst Ag Ester von arylperfluoralkylcarbinolen, verfahren zur herstellung dieser verbindungen und der zugrundeliegenden arylbisperfluoralkylcarbinole
JP2509282B2 (ja) * 1987-09-24 1996-06-19 鹿島石油株式会社 光学活性なジフルオロアルコ―ル誘導体
US5214069A (en) * 1988-12-23 1993-05-25 Imperial Chemical Industries Plc Alcohol and ether derivatives
NZ231735A (en) * 1988-12-23 1992-04-28 Ici Plc Alcohol/ether derivatives, preparation and pharmaceutical compositions thereof
JPH02200646A (ja) * 1989-01-31 1990-08-08 Nippon Oil & Fats Co Ltd フルオロアルキル基含有芳香族誘導体及びその製造方法
EP0403713A1 (en) * 1989-06-22 1990-12-27 Merrell Dow Pharmaceuticals Inc. Novel acetylcholinesterase inhibitors
DE3927049A1 (de) * 1989-08-16 1991-02-21 Sandoz Ag Halogenalkyl-phenyl-ketone und deren hydrate, ihre herstellung und verwendung
EP0611769A1 (en) * 1993-02-16 1994-08-24 Merrell Dow Pharmaceuticals Inc. Silylated acetylcholinesterase inhibitors

Also Published As

Publication number Publication date
AU6944294A (en) 1995-01-03
NO954896D0 (no) 1995-12-01
ES2127396T3 (es) 1999-04-16
NO306058B1 (no) 1999-09-13
FI955795A0 (fi) 1995-12-01
CA2164303C (en) 2000-11-28
TW385247B (en) 2000-03-21
HU9503452D0 (en) 1996-01-29
DE69415522D1 (de) 1999-02-04
EP0701546B1 (en) 1998-12-23
JP3735372B2 (ja) 2006-01-18
US5663448A (en) 1997-09-02
DE69415522T2 (de) 1999-06-02
JPH08511019A (ja) 1996-11-19
WO1994029255A1 (en) 1994-12-22
AU676578B2 (en) 1997-03-13
NO954896L (no) 1996-02-02
NZ267221A (en) 1997-11-24
ZA943787B (en) 1995-01-30
FI955795A (fi) 1995-12-01
CA2164303A1 (en) 1994-12-22
EP0701546A1 (en) 1996-03-20
DK0701546T3 (da) 1999-08-16
CN1124953A (zh) 1996-06-19
EP0627400A1 (en) 1994-12-07
IL109863A0 (en) 1994-10-07
IL109863A (en) 1998-12-27
HUT73484A (en) 1996-08-28
ATE174895T1 (de) 1999-01-15

Similar Documents

Publication Publication Date Title
KR960702820A (ko) 방향족 아세틸콜린에스테라제 억제제 (Aromatic acetylcholinesterase inhibitors)
KR950010888A (ko) 평활근세포 증식 및 재발협착증을 억제하는 방법
ES2190469T3 (es) Derivados de isocumarina y su uso en farmacos.
DE69329386T2 (de) Substituierte benzylaminoquinuclidine als substanz p antagonisten
SE7712693L (sv) Organiska foreningar
ES538418A0 (es) Un derivado de indol-3-carboxamida
DE69305276T2 (de) Arylglycinamidderivate, Verfahren zur deren Herstellung und deren Verwendung zur Therapie der Dysurie
CA2149872A1 (en) Diabetes prevention and treatment
DK288686A (da) Farmaceutiske praeparater
ATE173252T1 (de) Arylmorpholine, herstellung und verwendung
ATE22294T1 (de) Pyrido(3,4-c)psoralene, herstellung, verwendung in der kosmetologie und als arzneimittel und diese enthaltende zubereitungen.
BG60285B2 (en) Method and herbicide for unwanted vegetation control
DE3787844D1 (de) Thioester und dessen Verwendung zur Herstellung von pharmazeutischen Zusammensetzungen zur Behandlung von Ischämie und von Reperfusion-Syndromen.
ES8504159A1 (es) Un procedimiento para la preparacion de nuevos derivados de 1,2,5,-tidiazol.
DE69200365D1 (de) Pharmazeutische Zusammensetzung zur Verbesserung von Dysuria.
NZ237066A (en) Indole derivatives and pharmaceutical preparations
PT900082E (pt) Utilizacao de piridilpiperazina e pirimidilpiperazina para o fabrico de um medicamento para o tratamento de perturbacoes de toxicomania
RU98122110A (ru) Пиридил- и пиримидил-пиперазины в лечении болезней, вызываемых злоупотреблением лекарственными и/или наркотическими веществами
ES8401456A1 (es) Procedimiento para la preparacion de 2-aminometilfenoles.
DE59009388D1 (de) Pharmazeutisch wirksame Pteridinderivate.
AU8440991A (en) Phenolic thioetheramides as 5-lipoxygenase inhibitors
ATE2786T1 (de) 1-(2-propynyloxy)-2-amino-3-propanol-aether, ihre herstellung und sie enthaltende pharmazeutische zusammensetzung.
SE9300127L (sv) Tricyliska kondenserade 1,2,4-triazoloderivat användbara såsom antiinflammatoriska medel
ATE109485T1 (de) Derivate von n-(vincristinyl-23) und n- (noranhydro-5-vinblastinyl-23) von amino-1- methylphosphonsäure, ihre verfahren zur herstellung und sie enthaltende pharmazeutische zusammensetzungen.
DK601883D0 (da) Phenyl-propanolderivater

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E601 Decision to refuse application