KR970705996A - 5알파-환원 효소 저해제(5alpha-reductase inhibitors) - Google Patents

5알파-환원 효소 저해제(5alpha-reductase inhibitors)

Info

Publication number
KR970705996A
KR970705996A KR1019970701783A KR19970701783A KR970705996A KR 970705996 A KR970705996 A KR 970705996A KR 1019970701783 A KR1019970701783 A KR 1019970701783A KR 19970701783 A KR19970701783 A KR 19970701783A KR 970705996 A KR970705996 A KR 970705996A
Authority
KR
South Korea
Prior art keywords
alkyl
compound
group
formula
phenyl
Prior art date
Application number
KR1019970701783A
Other languages
English (en)
Inventor
제임스 에드먼드 오디아
로레타 암스 맥퀘이드
블레이크 리 뉴바우어
빈센트 패트릭 로코
케빈 리 헬
토마스 제이 크레스
제임스 패트릭 웹시엑
Original Assignee
스트링거 피터 지
일라이 릴리 앤드 캄파니
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 스트링거 피터 지, 일라이 릴리 앤드 캄파니 filed Critical 스트링거 피터 지
Publication of KR970705996A publication Critical patent/KR970705996A/ko

Links

Classifications

    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/08—Antiseborrheics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/28—Antiandrogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • 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
    • 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
    • C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
    • 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
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D417/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Reproductive Health (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

일련의 벤조퀴놀린-3-온은 I-형 및 Ⅱ-형 5α -환원 효소에 의해 야기된 상태를 치료하는데 효율적인 약제이다.

Description

5알파-환원 효소 저해제(5ALPHA-REDUCTASE INHIBITORS)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (15)

  1. 하기 화학식(I)의 화합물 또는 그의 약학적으로 허용가능한 염:
    상기식에서, R 및 R1은 둘다 수소를 나타내거나 함께 단일결합을 형성하고; R2는 수소 또는 C1-C3알킬을 나타내고; R3은 메틸 또는 에틸을 나타내고; R4및 -X-R5는 각각 7-, 8-, 및 9- 위치중 하나에 위치하고; R4는 수소, 할로, 메틸, 또는 에틸을 나타내고; X는 C1-C4알킬, C2-C4알케닐, C2-C4알키닐, 단일결합, -SO-, -SO2-, -CO-Y-(CH2)n, -Y-CO-(CH2)n, -CO-, -Z-(CH2)n-, 또는 -SO3-를 나타내고(여기서, 비대칭인 X그룹은 어떠한 배향으로도 존재할 수 있다.); Y는 -S-, -O-, 또는 -NH-를 나타내고; Z는 -O- 또는 -S-를 나타내고; n은 0 내지 3을 나타내고; R5는 페닐, 나프탈레닐, 피리디닐, 피라지닐, 피리다지닐, 피리미디닐, 안트라세닐, 아새나프탈레닐, 티아졸릴, 벤즈이미다졸릴, 인다졸릴, 티오페닐, 페난트레닐, 퀴놀리닐, 플루오레닐, 이소퀴놀리닐, 인다닐, 벤조피라닐, 인돌릴, 벤즈이소퀴놀리닐, 벤즈인돌릴, 벤조티아졸릴, 벤조티오페닐, 퀴녹살리닐, 벤즈옥사졸릴, 테트라졸릴, 나프토티아졸릴, 퀴나졸리닐, 티아졸로피리디닐, 피리다지노퀴나졸리닐, 벤즈이소티아졸릴, 벤조디옥솔릴, 벤조디옥시닐, 디페닐메틸 또는 트리페닐메틸을 나타내고; 상기 R5그룹은 비치환되거나 할로, 트리플루오로메틸, 트리플로오로메톡시, C1-C4알킬, 트리플로오로메톡시, 하이드록시, C1-C3알콕시, 니트로, C1-C3알킬티오, C1-C6알킬노일, 페닐, 옥소, 페녹시, 페닐티오, C1-C3알킬설피닐, C1-C3알킬설포닐, 시아노, 아미노, C1-C3알킬아미노, 디페닐메틸아미노, 트리페닐메틸아미노, 벤질옥시, 벤질티오, (모노-할로, 니트로, 또는 CF3)벤질(옥시 또는 티옥),디(C1-C3알킬,C3-C6사이클로알킬, 또는 C4-C8사이클로알킬알킬)아미노, (모노-C1-C3알킬,C1-C3)알콕시, 또는 할로)-(페닐, 페녹시, 페닐티오, 페닐설포닐, 또는 페녹시포닐), C2-C6알카노일아미노, 벤조일아미노, 디페닐메틸아미노(C1-C3알킬), 아미노카보닐, C1-C3알킬아미노타보닐, 디(C1-C3알킬)-아미노카보닐, 할로-C1-C3알카노일, 아미노설포닐, C1-C3알킬아미노설포닐, 디(C1-C3알킬)아미노설포닐, 페닐(옥시 또는 티오)(C1-C3알킬), (할로, C1-C3알킬 또는 C1-C3알콕시)페닐(옥시 또는 티오)(C1-C3알킬),벤조일, 또는(아미노, C1-C3알킬아미노 또는 디(C1-C3알킬)아미노(C1-C3알킬)로 구성된 그룹으로부터 선택된 1 내지 3개의 그룹으로 치환되거나; 또는 상기 R5그룹은 모폴리노(C1-C3알킬)그룹, 페닐(C1-C3알킬)피페리디닐 그룹, 페닐(C1-C3알킬)피페리디닐아미노카보닐 그룹, C2-C6알카노일아미노티오페닐 그룹, 또는(아미노, C1-C3알킬아미노 또는 디(C1-C3알킬)아미노)나프탈레닐설포닐아미노 그룹으로 치환되거나; 또는 R5는 퍼할로페닐 그룹이다.
  2. 제1항에 있어서, R 및 R5둘다가 수소를 나다내는 화합물.
  3. 제2항에 있어서, R3가 메틸을 나타내는 화합물.
  4. 제3항에 있어서, R2가 메틸 또는 수소를 나타낸 화합물.
  5. 제1항에 있어서, R4가 수소를 나타낸 화합물.
  6. 제3항에 있어서, X가 -CO-, -CO-Y-(CH2)n-, -Z-(CH2)n-, 알킬, 또는 단일결합을 나타내는 화합물.
  7. 제6항에 있어서, X가 단일결합 또는 황 원자를 나타내는 화합물.
  8. 제7항에 있어서, R5가 페닐, 나프탈레닐, 피리디닐, 피라지닐, 피리다지닐, 피리미디닐, 안트라세닐, 페난트레닐, 플루오레닐, 또는 아세나프탈레닐을 나타내고, 이들 R5그룹이 치환되거나 또는 비치환되는 화합물.
  9. 제7항에 있어서, R5가 벤조피라닐, 벤조티아졸릴, 벤조티오페닐, 또는 벤즈이소티아졸릴을 나타내고, 이들 R5그룹이 치환되거나 또는 비치환되는 화합물.
  10. 제1항에 있어서, (+)-(4aR)-(10bR)-4-메틸-8-(4-에틸-2-벤조티아졸릴티오)-10b-메틸-1,2,3,4,4a,5,6,10b-옥타하이드로벤조[f]퀴놀린-3-온인 화합물 또는 그의 약학적으로 허용가능한 염.
  11. 하나 이상의 약학적으로 허용가능한 담체와 함께, 활성 성분으로서 제1항 내지 제10항 중 어느 한 항에 따른 화학싱(Ⅰ)의 화합물 또는 그의 약학적으로 허용가능한 염을 포함하는 약학 제제.
  12. 과도한 5α-환원 활성에 의해 야기된 상태를 치료하는데 사용하기 위한, 제1항 내지 제10항 중 어느한 항에 따른 화학식(Ⅰ)의 화합물 또는 그의 약학적으로 허용가능한 염.
  13. 양성 전립선 과증식증을 치료하는데 사용하기 위한. 제 1항 내지 제10항중 어느 한 항에 따른 화학식(Ⅰ)의 화합물 또는 그의 약학적으로 허용가능한 염.
  14. 테트라하이드로푸란, 디메톡시에탄, 디에톡시에탄, 및 메틸 t-부틸 에테르로 구성된 그룹으로부터 선택된 유기 용매, 및 수성 수산화 나트륨 또는 수산화 칼륨을 포함하는 반응 혼합물중에서, 하기 화학식(B)의 화합물을 요오드화 메틸, 요오드화 에틸 또는 요오드화 n-프로필과 반응시키는 것을 포함하는, 하기 화학식(A)화합물의 제조방법:
    상기식에서, R2′는 메틸, 에틸 또는 n-프로필이고; R3′는 수소 또는 메틸이고; R4는 수소, 할로, 메틸 또는 에틸이고;R5′는 할로, 니트로, 시아노, C1-C6알킬, 트리플루오로메틸 또는 C1-C6알콕시이거나; 또는 R5′는 A가 C1-C6알킬, C2-C6알케닐, 또는 C2-C6알키닐인 -A-R6그룹이거나; 또는 R5′는 X′가 C1-C4알킬, C2-C4알케닐, C2-C4알키닐 또는 단일결합인 -X′-R7그룹이고; R6은 할로, 트리플루오로메틸, 또는 C1-C6알콕시이고; R7은 페닐, 나프탈레닐, 피리디닐, 피라지닐, 피리다지닐 피리미디닐르 안트라세닐, 아세타프탈레닐, 티아졸릴, 벤즈이미다졸릴, 인다졸릴, 티오페닐, 페난트레닐, 퀴놀리닐, 플푸오레닐, 이소퀴놀리닐, 인다닐, 벤조피라닐, 인돌릴, 벤즈이소퀴놀리닐, 벤즈인돌릴, 벤조티아졸릴, 벤조티오페닐, 퀴녹살리닐, 벤즈옥사졸릴, 테트라졸릴, 나프토티아졸릴, 퀴나졸리닐, 티아졸로피리디닐, 피리다지노퀴나졸리닐, 벤즈이소티아졸릴, 벤조디옥솔릴, 벤조디옥시닐, 디페닐메틸 또는 트리페닐메틸이고; 상기 R7그룹은 비치환되거나 또는 할로, 트리플루오로메틸, 트리플루오로에톡시, C1-C4알킬, 트리플루오로메톡시, 하이드록시, C1-C3알콕시, 니트로, C1-C3알킬티오, C1-C6알카노일, 페닐, 옥시, 페녹시, 페닐티오, C1-C3알킬설포닐, 시아노, 벤질옥시, 벤질티오, (모노-할로, 니트로 또는 트리플루올메틸)벤질(옥시 또는 티오),(모노-C1-C3알킬, C1-C3알콕시 또는 할로)-(페닐, 페녹시, 페닐티오, 페닐설포닐 또는 페녹시설포닐), 할로-C1-C6알카노일, 페닐(옥시 또는 티오)(C1-C3알킬), (할로, C1-C3알콕시)페닐(옥시 또는 티오)(C1-C3알킬), 또는 벤조일로 구성된 그룹으로부터 선택된 1 내지 3개의 그룹으로 치환되거나; 또는 상기 R7그룹은 모폴리노(C1-C3알킬)그룹, 또는 페닐(C1-C3알킬)피페리디닐 그룹으로 치환되거나; 또는 R7은 퍼할로페닐 그룹이다.
  15. (a) 하기 화학식(Ⅱ)의 중간 생서물을 활성화된 형태로 화학식 X-R5의 화합물과 반응시키거나, 활성화된 형태의 화학식(Ⅱ)의 화합물을 화학시 L-X-R5의 화합물가 반응시키고;(b)화학식(Ⅱ)의 화합물을 화학식 -X-R5의 화합물과 반응시키거나. -L이 -Z에 의해 치환된 화학식(Ⅱ)의 화합물을 화학식 L-X-R5의 화합물과 반응시켜 X가 -Z-(CH2)n-인 화학식(Ⅰ)의 화합물을 제조하고; (c) -L이 -YH, -CO-L, -(CH2)n-YH, 또는 -(CH2)n-CO-L 중 하나로 치환된 화학식(Ⅱ)의 화합물을 화학식 HY-R5, L-CO-R5, HY-(CH2)n-R5, 또는 L-CO-(CH2)n-R5중 하나의 화합물과 반응시켜 X가 -CO-Y-(CH2)n- 또는 -Y-CO-(CH2)n또는 -Y-CO-(CH2)n인 화학식(Ⅰ)의 화합물을 제조하며(이 경우에, 한 반응물은 -YH그룹을 가지며 다른 반응물은 L그룹을 가지고, 하나의 반응물만이 -(CH2)n그룹을 가진다.; (d) 활성화된 형태의 화학식(Ⅱ)의 화합물을 -X-R5잔기를 제공하는 알데히드 또는 케톤과 반응시켜 X가 알칼인 화학식(Ⅰ)의 화합물을 제조하고; (e) R2가 수소인 화학식(Ⅰ)의 화합물을 화학식 R2-1의 요오드화 알킬과 반응시켜 R2가 C1-C3알킬인 화학식(Ⅰ)의 화합물을 제조하거나; 또는 (f) 생성물을 산화시켜 R 및 R1이 함께 단일결합을 형성하는 화학식(Ⅰ)의 화합물을 제조하거나; 또는 (g) X그룹을 산화 또는 환원시키거나; 또는 (h) 보호그룹을 제거하거나; 또는 (i) 염을 제조하거나; 또는 (j) 광학 이성질체를 단리하는 상기 화학식(Ⅰ)의 화합물의 제조방법 :
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019970701783A 1994-09-20 1995-09-14 5알파-환원 효소 저해제(5alpha-reductase inhibitors) KR970705996A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/309,282 US5578724A (en) 1994-09-20 1994-09-20 Process for preparation of benzo[f]quinolinones
US08/309,282 1994-09-20
PCT/US1995/011521 WO1996009046A1 (en) 1994-09-20 1995-09-14 5α-REDUCTASE INHIBITORS

Publications (1)

Publication Number Publication Date
KR970705996A true KR970705996A (ko) 1997-11-03

Family

ID=23197530

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019970701783A KR970705996A (ko) 1994-09-20 1995-09-14 5알파-환원 효소 저해제(5alpha-reductase inhibitors)

Country Status (17)

Country Link
US (4) US5578724A (ko)
EP (1) EP0703221B1 (ko)
JP (1) JPH08225533A (ko)
KR (1) KR970705996A (ko)
AU (2) AU3510295A (ko)
BR (1) BR9509015A (ko)
CA (1) CA2158609C (ko)
CZ (1) CZ82197A3 (ko)
DE (1) DE69526475T2 (ko)
ES (1) ES2173940T3 (ko)
FI (1) FI971156A (ko)
HU (1) HUT77947A (ko)
MX (1) MX9702035A (ko)
NO (1) NO307930B1 (ko)
NZ (1) NZ292819A (ko)
PL (1) PL319163A1 (ko)
WO (1) WO1996009046A1 (ko)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5635197A (en) * 1995-03-21 1997-06-03 Eli Lilly And Company Treatment and prevention of prostatic cancer metastasis
US5629007A (en) * 1995-03-21 1997-05-13 Eli Lilly And Company Method of preventing prostatic cancer development
US5550134A (en) * 1995-05-10 1996-08-27 Eli Lilly And Company Methods for inhibiting bone loss
US6111110A (en) * 1996-10-30 2000-08-29 Eli Lilly And Company Synthesis of benzo[f]quinolinones
JP2001504816A (ja) * 1996-10-30 2001-04-10 イーライ・リリー・アンド・カンパニー ベンゾ［ｆ］キノリノンの合成
AU5594398A (en) * 1996-12-09 1998-07-03 Merck & Co., Inc. Methods and compositions for preventing and treating bone loss
US6037326A (en) * 1996-12-31 2000-03-14 Styczynski; Peter Reduction of hair growth
EP0926148A1 (en) * 1997-12-23 1999-06-30 Applied Research Systems Ars Holding N.V. Benzo (C)quinolizine derivatives, their preparation and use as 5-alphareductases inhibitors
US6632447B1 (en) 1998-05-07 2003-10-14 The University Of Tennessee Research Corporation Method for chemoprevention of prostate cancer
US6410043B1 (en) 1998-05-07 2002-06-25 The University Of Tennessee Research Corporation Method for chemoprevention of prostate cancer
US6048869A (en) * 1998-07-29 2000-04-11 Merck & Co., Inc. Tricyclic compounds
US6481721B1 (en) 1999-07-15 2002-11-19 Lucent Technologies Inc. Method and apparatus for overcladding a glass rod
US20020010528A1 (en) * 2000-03-31 2002-01-24 Imx Labs, Inc. Nail Polish color selection system
GB201102913D0 (en) 2011-02-18 2011-04-06 Univ Birmingham Novel therapeutic
US11370757B2 (en) * 2017-10-18 2022-06-28 Board Of Regents, The University Of Texas System Photocleavable nitroindoline-based crosslinkers
US11820439B2 (en) * 2020-12-16 2023-11-21 Steering Solutions Ip Holding Corporation Power-assist assembly

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE8302361D0 (sv) * 1983-04-27 1983-04-27 Astra Laekemedel Ab New tricyclic amines
US4760071A (en) * 1984-02-27 1988-07-26 Merck & Co., Inc. 17β-N-monosubstituted carbamoyl-4-aza-5α-androst-1-en-3-ones which are active as testosterone 5α-reductase inhibitors
ZA883034B (en) * 1987-04-29 1989-03-29 Smithkline Beckman Corp Steroid 5-alpha-reductase inhibitors
US4923868A (en) * 1989-02-21 1990-05-08 American Cyanamid Company 8-fluoro and 7,8,10-trifluoro-9-(substituted)-6-oxo-6H-benzo(C)quinolizine-5-carboxylic acids
CA2011640A1 (en) * 1989-03-20 1990-09-20 Rene Imhof Quinoline derivatives
US5300294A (en) * 1990-06-27 1994-04-05 Smithkline Beecham Corporation Method of treating prostatic adenocarcinoma
IE76452B1 (en) * 1990-10-29 1997-10-22 Sankyo Co Azasteroid compounds for the treatment of prostatic hypertrophy their preparation and use
US5239075A (en) * 1991-08-21 1993-08-24 Eli Lilly And Company Process for the preparation of benzo (f) quinolinones
US5250539A (en) * 1991-08-21 1993-10-05 Eli Lilly And Company Hexahydrobenzo[f]quinolinones
ES2169026T3 (es) * 1991-08-21 2002-07-01 Lilly Co Eli Benzo(f)quinolinonas como inhibidores de 5-alfa-reductasa.
ES2125884T3 (es) * 1991-08-21 1999-03-16 Lilly Co Eli Hexahidrobenzo(f)quinolinonas como inhibidores de la 5-alfa-reductasa.
US5175155A (en) * 1991-10-07 1992-12-29 Sterling Winthrop Inc. Win 49596-finasteride method of use and compositions
TW224091B (ko) * 1992-04-03 1994-05-21 Lilly Co Eli
US5356935A (en) * 1993-12-13 1994-10-18 Eli Lilly And Company Reduced phenanthrenes

Also Published As

Publication number Publication date
NZ292819A (en) 1999-01-28
CA2158609C (en) 2006-07-11
NO307930B1 (no) 2000-06-19
AU692123B2 (en) 1998-05-28
WO1996009046A1 (en) 1996-03-28
DE69526475D1 (de) 2002-05-29
US5622962A (en) 1997-04-22
MX9702035A (es) 1997-06-28
PL319163A1 (en) 1997-07-21
AU1898197A (en) 1997-06-26
EP0703221B1 (en) 2002-03-27
BR9509015A (pt) 1998-01-06
CA2158609A1 (en) 1996-03-21
NO971248D0 (no) 1997-03-18
FI971156A0 (fi) 1997-03-19
JPH08225533A (ja) 1996-09-03
DE69526475T2 (de) 2002-09-26
EP0703221A1 (en) 1996-03-27
FI971156A (fi) 1997-03-19
US5578724A (en) 1996-11-26
US5622961A (en) 1997-04-22
AU3510295A (en) 1996-04-09
US6150375A (en) 2000-11-21
NO971248L (no) 1997-03-18
ES2173940T3 (es) 2002-11-01
HUT77947A (hu) 1998-12-28
CZ82197A3 (cs) 1998-01-14

Similar Documents

Publication Publication Date Title
KR970705996A (ko) 5알파-환원 효소 저해제(5alpha-reductase inhibitors)
EP1242404B1 (fr) Phenoxypropanolamines, leur preparation et leur application en therapeutique
YU19002A (sh) Derivati hinolil-propil-piperidina, njihovo dobivanje i smeše koje ih sadrže
BR0214164A (pt) Ligantes do receptor canabinóide
RU98102128A (ru) Производные бензо[g]хинолина
EP1354878A3 (en) Tetrahydroquinoline derivatives having selective activity for retinoid x receptors
EA199900937A1 (ru) Фармацевтические композиции, содержащие вориконазол
RU93056600A (ru) Фенокси- и феноксиалкилпиперидиновые соединения и антивирусная композиция
TR200301723T4 (tr) 1,3 Dihidro-2H-indol-2 one türevleri ve bunların, arginin-vasopressin' in V1B veya V1B reseptörleri için bağ maddeleri olarak kullanımı
CA2011087A1 (en) Use of trifluoromethylphenylazolylmethyloxiranes as crop protection agents
CO5251438A1 (es) Derivados del acido hidroxamico sustituidos por arilsul- fonamido, compuestos y composiciones farmaceuticas que los contienen y procedimiento para su aplicacion y preparacion
DE69921151D1 (de) Fluorszierende marker
RU2000102902A (ru) Состав минеральной ваты и термо-звукоизоляционный продукт на его основе
KR900018048A (ko) 환 치환된 2-아미노-1,2,3,4-테트라하이드로나프탈렌
AR033300A1 (es) Compuestos de cefem
EP1106167A3 (en) Dye compositions for keratin fibers comprising a nonionic compound
DE50105454D1 (de) Verfahren zur katalytischen Reduktion von Alkinverbindungen
BR9914438A (pt) Processo aperfeiçoado para a preparação de novos agentes anti-diabéticos
KR840002363A (ko) 살충제조성물 및 그 제조방법
BR9812085A (pt) "método para a sìntese de derivados de quinolina"
KR910011880A (ko) 신규 화합물
Conte et al. Enantioselective oxidation of β-hydroxythioethers. Synthesis of optically active alcohols and epoxides
PE20030327A1 (es) 3-5-dihidroxi-2,2-dimetil-valeronitrilos protegidos para la sintesis de epotilonas y sus derivados y metodo para su obtencion
ATE187160T1 (de) Verfahren zur herstellung eines substituierten 2,5-diamino-3-hydroxy hexanes
WO2001051004A3 (en) Anti-cancer agent containing naphthoquinone compound

Legal Events

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