KR910015569A - 피페리딘화합물, 이의 제법 및 이의 용도 - Google Patents

피페리딘화합물, 이의 제법 및 이의 용도 Download PDF

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KR910015569A
KR910015569A KR1019900002108A KR900002108A KR910015569A KR 910015569 A KR910015569 A KR 910015569A KR 1019900002108 A KR1019900002108 A KR 1019900002108A KR 900002108 A KR900002108 A KR 900002108A KR 910015569 A KR910015569 A KR 910015569A
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tetrahydro
thiadiazol
methylpyridine
alkyl
alkynyl
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사우에르베르그 페르
훌벨르그 올센 프레벤
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따쥬 오노레
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • 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
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Abstract

내용 없음

Description

피페리딘화합물, 이의 제법 및 이의 용도
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (7)

  1. 일반식(Ⅰ)의 화합물 또는 약제학적으로 허용되는 산과의 염.
    상기식에서, Z는 산소 또는 황이고, R은 H, C1-3-알킬, C3-4-사이클로알킬, C2-4-알케닐, C2-4-알키닐이며, R1은 C1-15-알킬, C2-15-알케닐, C2-15-알키닐, C3-7-사이클로알킬, C4-8-사이클로알킬알킬, 페녹시, 벤질옥시, 모르폴리노, C1-6-알킬 치환된 피페리디노, 할로겐, 아미노, C1-6-아실아미노, C1-15-알킬아미노, C1-15-디알킬아미노, C1-15-알콕시아미노, S-R2또는 O-R2이고, R2는 직쇄 또는 측쇄 C1-15-알킬, 직쇄 또는 측쇄 C2-15-알케닐, 직쇄 또는 측쇄 C2-15-알키닐, R3-O-R4, R|3-NH-R4, R3-S-R4, R3-O-R4-O-R5이며, R3, R4및 R5는 독립적으로 C1-15-알킬, C2-15-알케닐, C2-15-알키닐이다.
  2. 1, 2, 5, 6-테트라하이드로-3-(4-메톡시-1, 2, 5-티아디아졸-3-일)-1-메틸피리딘; 3-(4-에톡시-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 1, 2, 5, 6-테트라하이드로-1-메틸-3-(4-프로폭시-1, 2, 5-티아디아졸-3-일)피리딘; 3-(4-부톡시-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 1, 2, 5, 6-테트라하이드로-3-(4-이소프로폭시-1, 2, 5-티아디아졸-3-일)-1-메틸피리딘; 1, 2, 5, 6-테트라하이드로-1-메틸-3-(4-펜틸옥시-1, 2, 5-티아디아졸-3-일)피리딘; 1, 2, 5, 6-테트라하이드로-3-(4-이소부톡시-1, 2, 5-티아디아졸-3-일)-1-메틸피리딘; 1, 2, 5, 6-테트라하이드로-3-(4-이소펜틸옥시-1, 2, 5-티아디아졸-3-일)-1-메틸피리딘; 3-(4-헥실옥시-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-벤질옥시-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(3-부테닐옥시)-1,2,5-티아디아졸-3-일)-1,2,5,6-테트라하이드로-1-메틸피리딘; 3-(4-(2-부티닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 1, 2, 5, 6-테트라하이드로-1-메틸-3-(4-프로파르길옥시-1, 2, 5-티아디아졸-3-일)피리딘; 3-(4-사이클로프로필메톡시-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 1, 2, 5, 6-테트라하이드로-3-(4-메톡시에톡시-1, 2, 5-티아디아졸-3-일)-1-메틸피리딘; 3-(4-클로로-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-클로로-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로피리딘 하이드로클로라이드 3-(4-부톡시-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로피리딘; 3-(4-클로로-1, 2, 5-티아디아졸-3-일)-1-에틸-1, 2, 5, 6-테트라하이드로피리딘; 3-(4-에톡시-1, 2, 5-티이디아졸-3-일)-1-에틸-1, 2, 5, 6-테트라하이드로피리딘; 3-(4-헵틸옥시-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(3-펜티닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(4-펜테닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(2-프로페닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-옥틸옥시-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(3-헥시닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(3-메틸-2-부테닐옥식)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(3-부테닐-2-옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(4-헥세닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 트랜스-3-(4-(3-헥세닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 시스-3-(4-(2-펜테닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 시스-3-(4-(2-헥세닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(5-헥세닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 시스-3-(4-(3-헥세닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 트랜스-3-(4-(2-헥세닐옥시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 1, 2, 5, 6-테트라하이드로-3-(3-헥실옥시-1, 2, 5-티아디아졸-3-일)피리딘; 3-(4-(2-(2-메톡시에톡시)에톡시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(3-에톡시-1-프로폭시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(2-에톡시에톡시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(2-부톡시에톡시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(2-(2-부톡시에톡시)에톡시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(2-(2-에톡시에톡시)에톡시)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(4-메틸피페리디노)-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-모르폴리노-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-헥실아미노-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-프로필티오-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-부틸티오-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-메틸티오-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-아미노-1, 2, 5-옥사디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-아세틸아미노-1, 2, 5-옥사디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-클로로-1, 2, 5-옥사디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(1, 2, 5-옥사디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-헥실옥시-1, 2, 5-옥사디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-부틸옥시-1, 2, 5-옥사디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-(3-헥시닐옥시-1, 2, 5-옥사디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-펜틸-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리디늄 옥살레이트 3-(4-헵틸-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리디늄 옥살레이트 3-(4-(5-헥세닐-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리디늄 옥살레이트 3-(4-옥틸-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리디늄 옥살레이트 3-(4-이소부틸-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리디늄 옥살레이트 3-(4-사이클로프로필메틸-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리디늄 옥살레이트 3-(4-프로필-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리디늄 옥살레이트 3-(4-옥틸티오-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-에틸티오-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-펜틸티오-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘; 3-(4-헥실티오-1, 2, 5-티아디아졸-3-일)-1, 2, 5, 6-테트라하이드로-1-메틸피리딘중에서 선택된 화합물 및 약제학적으로 허용되는 산과의 염.
  3. 일반식(Ⅱ)의 화합물을 알킬 할라이드로 알킬화시키고 이렇게 하여 형성된 화합물을 하이드라이드 이온으로 환원시켜 일반식(Ⅰ)의 화합물을 형성함을 특징으로 하여, 일반식(Ⅰ)의 화합물 또는 약제학적으로 허용되는 산과의 염을 제조하는 방법.
    상기식에서, Z는 산소 또는 황이고, R은 H, C1-3-알킬, C3-4-사이클로알킬, C2-4-알케닐 또는 C2-4-알키닐이며, R1은 C1-15-알킬, C2-15-알케닐, C2-15-알키닐, C3-7-사이클로알킬, C4-8-사이클로알킬알킬, 페녹시, 벤질옥시, 모르폴리노, C1-6-알킬 치환된 피페리디노, 할로겐, 아미노, C1-6-아실아미노, S-R2는 O-R2이고, R2는 직쇄 또는 측쇄 C1-15-알킬, 직쇄 또는 측쇄 C2-15-알케닐, 직쇄 또는 측쇄 C2-15-알키닐, R3-O-R4, R3-NH-R4, R3-S-R4, R3-O-R4-O-R5이며, R3, R4및 R5는 독립적으로 C1-15-알킬, C2-15-알케닐, C2-15-알키닐이다.
  4. 인간을 포함하는 포유동물의 대뇌 및 해마의 인식 작용을 자극하기에 적합하고, 알쯔하이머 질환 및/또는 심한 통증성 상태 및/또는 녹내장 치료에 적합한 일반식(Ⅰ) 화합물 (여기서, 화합물은 약제학적으로 허용되는 담체 또는 희석제와 함게 포유동물의 대뇌 및 해마 자극 또는 알쯔하이머 질환 치료에 효과적이다) 또는 약제학적으로 허용되는 산과의 염을 포함하는 약제학적 조성물.
    상기식에서, Z는 산소 또는 황이고, R은 H, C1-3-알킬, C3-4-사이클로알킬, C2-4-알케닐 또는 C2-4-알키닐이며, R1은 C1-15-알킬, C2-15-알케닐, C2-15-알키닐, C3-7-사이클로알킬, C4-8-사이클로알킬알킬, 페녹시, 벤질옥시, 모르폴리노, C1-6-알킬 치환된 피페리디노, 할로겐, 아미노, C1-6-아실아미노, C1-15-알킬아미노, C1-15-디알킬아미노, C1-15-알콕시아미노, S-R2는 O-R2이고, R2는 직쇄 또는 측쇄 C1-15-알킬, 직쇄 또는 측쇄 C2-15-알케닐, 직쇄 또는 측쇄 C2-15-알키닐, R3-O-R4, R3-NH-R4, R3-S-R4, R3-O-R4-O-R5이며, R3, R4및 R5는 독립적으로 C1-15-알킬, C2-15-알케닐, C2-15-알키닐이다.
  5. 제4항에 있어서, 일반식(Ⅰ)의 화합물 1 내지 100㎎을 함유하는 경구 단위 용량 또는 약제학적으로 허용되는 산과의 염 형태인 약제학적 조성물.
  6. 일반식(Ⅰ)의 화합물 또는 약제학적으로 허용되는 산과의 염을 자극 및/또는 치료를 필요로하는 대상에 투여하는 단계를 포함함을 특징으로 하여, 자극 및/또는 치료를 필요로하는 대상의 대뇌 및 해마의 인식 작용을 자극하므로써 알쯔하이머 질환 및/또는 심한 통증성 상태 및/또는 녹내장을 치료하는 방법.
    상기식에서, Z는 산소 또는 황이고, R은 H, C1-3-알킬, C3-4-사이클로알킬, C2-4-알케닐 또는 C2-4-알키닐이며, R1은 C1-15-알킬, C2-15-알케닐, C2-15-알키닐, C3-7-사이클로알킬, C4-8-사이클로알킬알킬, 페녹시, 벤질옥시, 모르폴리노, C1-6-알킬 치환된 피페리디노, 할로겐, 아미노, C1-6-아실아미노, C1-15-알킬아미노, C1-15-디알킬아미노, C1-15-알콕시아미노, S-R2는 O-R2이고, R2는 직쇄 또는 측쇄 C1-15-알킬, 직쇄 또는 측쇄 C2-15-알케닐, 직쇄 또는 측쇄 C2-15-알키닐, R3-O-R4, R3-NH-R4, R3-S-R4, R3-O-R4-O-R5이며, R3, R4및 R5는 독립적으로 C1-15-알킬, C2-15-알케닐, C2-15-알키닐이다.
  7. 제6항에 있어서, 일반식(Ⅰ)의 화합물을 약제학적으로 허용되는 담체 또는 희석제와 함께 약제학적 조성물 형태로 투여하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900002108A 1989-02-22 1990-02-21 피페리딘 화합물, 이의 제조방법 및 용도 KR0163763B1 (ko)

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DK825/89 1989-02-22
DK0825/89 1989-02-22
DK82589A DK82589A (da) 1989-02-22 1989-02-22 Piperidinforbindelser, deres fremstilling og anvendelse
DK2314/89 1989-05-12
DK231589A DK231589D0 (da) 1989-05-12 1989-05-12 Piperidinforbindelser og deres fremstilling og anvendelse
DK2315/89 1989-05-12

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