KR920008006A - 류코트리엔 길항제로서의 불포화 하이드록시 알킬퀴놀린산 - Google Patents

류코트리엔 길항제로서의 불포화 하이드록시 알킬퀴놀린산 Download PDF

Info

Publication number
KR920008006A
KR920008006A KR1019910017953A KR910017953A KR920008006A KR 920008006 A KR920008006 A KR 920008006A KR 1019910017953 A KR1019910017953 A KR 1019910017953A KR 910017953 A KR910017953 A KR 910017953A KR 920008006 A KR920008006 A KR 920008006A
Authority
KR
South Korea
Prior art keywords
compound
independently
substituted
alkyl
pharmaceutically acceptable
Prior art date
Application number
KR1019910017953A
Other languages
English (en)
Other versions
KR100227716B1 (ko
Inventor
엘. 벨리 미셀
레거 서지
로이 패트릭
빈 지앙 이
라벨르 마크
궤이 다니엘
Original Assignee
제임스 에프. 너튼
머크 프로스트 캐나다 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27082671&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=KR920008006(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by 제임스 에프. 너튼, 머크 프로스트 캐나다 인코포레이티드 filed Critical 제임스 에프. 너튼
Publication of KR920008006A publication Critical patent/KR920008006A/ko
Application granted granted Critical
Publication of KR100227716B1 publication Critical patent/KR100227716B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/10—Expectorants
    • 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
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/14—Decongestants or antiallergics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Rheumatology (AREA)
  • Immunology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Quinoline Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)

Abstract

내용 없음

Description

류코트리엔 길항제로서의 불포화 하이드록시 알킬퀴놀린산
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (17)

  1. 하기 일반식(Ⅰ)의 화합물 및 이의 약제학적으로 허용되는 염 :
    (I)
    상기식에서, R1은 H, 할로겐, -CF3, -CN, -NO2또는 N3이고; R2은 저급 알킬, 저급 알켄일, 저급 알킨일, -CF3, -CH2F, -CHF2, CH2CF3, 치환되거나 비치환된 페닐, 치환되거나 비치환된 벤질, 치환되거나 비치환된 2-펜에틸이거나, 동일한 탄소원자에 결합된 2개의 R2그룹은 O, S 및 N중에서 선택된 0내지 2개의 헤테로원자를 함유하는 8원 이하의 환을 형성할 수 있고; R3는 H 또는 R2이고; CR3R22는 표준 아미노산 라디칼일 수 있고; R4는 할로겐, -NO2, -CN, -OR3, -SR3, NR3R3, NR3C(O)R7또는 R3이고; R5는 H, 할로겐, -NO2, -N3, -CN, -SR2, -NR3R3, -OR3, 저급 알킬 또는 -C(O)R3이고; R6는-(CH2)s-C(R7R7)-(CH2)s-R3또는 -CH2C(O)NR12R12이고; R7은 H 또는 C1-C4알킬이고; R8은 (A)3내지 12개의 핵 탄소원자 및 N, S및 O중에서 선택된 1개 또는 2개의 핵 헤테로원자를 함유하는 모노사이클릭 또는 비사이클릭 헤테로사이클릭 라디칼(헤테로사이클릭 라디칼의 각각의 환은 5개 또는 6개의 원자로 이루어진다) 또는,(B)라디칼 W-R9이고; R9은 20개 이하의 탄소원자를 함유하는, (1)알킬 그룹이거나 (2)환에 0내지 1개의 헤테로 원자를 함유하는 유기 비환식 또는 모노사이클릭 카복실산의 알킬카보닐 그룹이고; R10은 -SR11, -OR12또는 -NR12R12이고; R11은 저급 알킬, -C(O)R14, 비치환된 페닐 또는 비치환된 벤질이고; R12는 H 또는 R11이거나, 동일한 N원자에 결합된 2개의 R12그룹은 O, S 및 N중에서 선택된 1내지 2개의 헤테로원자를 함유하는 5또는 6원 환을 형성할 수 있고; R13은 저급 알킬, 저급 알켄일, 저급 알킨일, -CF3또는 치환되거나 비치환된 페닐, 벤질 또는 2-펜에틸이고; R14는 H 또는 R13이고; R16은 H, C1-C4알킬 또는 OH이고; R17은 저급 알킬, 저급 알켄일, 저급 알킨일, 또는 치환되거나 비치환된 페닐, 벤질 또는 2-펜에틸이고; R18은 저급 알킬, 저급 알켄일, 저급 알킨일, -CF3또는 치환되거나 비치환된 페닐, 벤질 또는 2-펜에틸이고; R19은 저급알킬, 저급 알켄일, 저급 알킨일, -CF3또는 치환되거나 비치환된 페닐, 벤질 또는 2-펜에틸이고: R20은 H, C1- C4알킬, 치환되거나 비치환된 페닐, 벤질, 펜에틸 또는 피리딜이거나, 동일한 N 원자에 결합된 2개의 R20그룹은 O, S 및 N 중에서 선택된 1내지 2개의 헤테로원자를 함유하는 5 또는 6원의 포화된 환을 형성할 수 있고; R21은 H 또는 R17이고; R22는 R4, CHR7OR3또는 CHR7SR2이고; m 및 m'은 독립적으로 0내지 8이고; n 및 n'은 독립적으로 0 또는 1이고; p 및 p' 독립적으로 0 내지 8이고; m+n+p는 r이 1이고 X2가 O, S, S(0)또는 S(0)2일때 1내지 10이고; m+n+p는 r이 1이고 X2가 CR3R16일때 0내지 10이고; m+n+p는 r이 0일때 0내지 10이고; m'+n'+p'은 0내지 10이고; r 및 r'은 독립적으로 0 또는 1이고; s는 0내지 3이고; Q1은 -C(O)OR3, -1H(또는 2H)-테트라졸-5-일, -C(O)OR6, C(O)NHS(O)2R13, -CN, -C(O)NR12R12, -NR21S(O)2R13, -NR12C(O)NR12R12, -NR21C(O)R18, -OC(O)NR12R12, -C(O)R19, -S(O)R18, -S(O)2R18, -S(O)2NR12R12, -NO2, -NR21C(O)OR17, -C(NR12R12=NR12, -(R13)=NOH이거나; Q1이 -C(O)OH 이고 R22가 -OH, -SH, -CHR7OH또는 -NHR3일때, Q1및 R22는 이들이 결합한 탄소원자와 함께 물을 상실하여 헤테로사이클릭 환을 형성할 수 있고; Q2는 OH 또는 NR20R20이고; W는 O, S 또는 NR3이고 X2및 X3는 독립적으로 O,S,S(O), S(O)2또는 CR3R16이고; Y는 -CR3=R3- 또는 -C=C-이고: Z1및 Z2는 독립적으로 -HET (-R3-R5)-이고; HET 는 벤젠, 피리딘, 푸란 또는 티오펜의 이라디칼이다.
  2. 제1항에 있어서, R1이 H, 할로겐, -CF3또는 -CN이고; R2는 C1-C4알킬, -CF3, -CH2F, -CHF2이거나, 동일한 탄소원자에 결합된 2개의 R2그룹은 6개 이하의 탄소원자로 이루어지는 환을 형성할 수 있고; R3는 H 또는 R2이고; CR3R22는 표준 아미노산 라디칼일 수 있고; R4는 -OR3, -SR3, NR3R3, NHC(O)CH3또는 R3이고; R5는 H 또는 할로겐이고; R6는 -(CH2)s-C(R7R7)-(CH2)s-R8또는 -CH2C(O)NR12R12이고; R7은 H또는 C1-C4알킬이고; R8은 (A)3내지 12개의 핵 탄소원자 및 N, S 및 O중에서 선택됨 1 또는 2개의 핵 헤테로원자를 함유하는 모노사이클릭 또는 비사이클릭 헤테로사이클릭 라디칼(헤테로 사이클릭 라디칼의 각각의 환은 5 또는 6개의 원자로 이루어진다) 또는 (B)라디칼 W-R9이고; R9은 20개 이하의 탄소원자를 함유하며, (1)알킬 그룹이거나 (2)알킬카보닐 그룹이고; R10은 -SR11, OR12또는 -NR12R12이고;R11은 저급 알킬, -C(O)R14, 비치환된 페닐 또는 비치환된 벤질이고; R12는 H 또는 R11이거나, 동일한 N원자에 결합된 2개의 R12그룹은 O, S 및 N중에서 선택된 1 내지 2개의 헤테로원자를 함유하는 5또는 6원 환을 형성할 수 있거나; R13은 저급알킬, -CF3, 또는 치환되거나 비치환된 페닐, 벤질 또는 2-펜에틸이고; R14는 H 또는 R13이고; R16은 H, C1-C4알킬 또는 OH이고; R22는 R4, -CH2OR3또는 -CH2SR2이고; m 및 m'은 독립적으로 0내지 4이고; n 및 n'은 독립적으로 0또는 1이고; p 및 p'은 독립적으로 0내지 4이고 m＋n＋P는 r이 1이고 X2가 0 또는 2일 때 1내지 9이고; m+n+p는 r이 1이고 X2가 CR3R16일때 0 내지 9이고; m+n+p는 r이 0일때 0 내지 9이고; m'+n'+p'은 1내지 9이고; r 및 r'은 독립적으로 0 또는 1이고; s는 0 내지 3이고; Q1은 -C(O)OR3, -1H(또는 2H)-테트라졸-5-일, -C(O)OR6, C(O)NHS(O)2R13, -C(O)NR12R12, -NHS(O)2R13이거나; Q1이 -C(O)OH이고 R22가 -OH, -SH, -CH2OH 또는 -NHR3일때 Q1및 R22는 이들이 결합한 탄소원자들과 함께 물을 상실하여 헤테로사이클릭 환을 형성할 수 있고; Q2는 OH이고; W는 O, S 또는 NH 이고; X2및 X3는 독립적으로 O, S 또는 CR3R16이고; Y는 (E)-CH=CH-이고; Z1및 Z2는 독립적으로 -HET(-R3-R5)-이고; HET는 벤젠, 피리딘, 푸란 또는 티오펜의 이라디칼인 일반식( I )의 화합물 및 이의 약제학적으로 허용되는 염.
  3. 제1항에 있어서, Q1에 대해위치에 존재하는 R22가 저급 알킬, CF3또는 치환되거나 비치환된 페닐인 일반식(l)의 화합물 및 이의 약제학적으로 허용되는 염.
  4. 제1항에 있어서, 하기 일반식(Ia)의 화합물 및 이의 약제학적으로 허용되는 염:
    (Ia)
    상기식에서, R1은 H, 할로겐, CF3또는 CN이고; R22는 R3, -CH2OR3또는 -CH2SR2이고; Q1은 -C(O)OH, 1H(또는 2H)-테트라졸-5-일, -C(O)NHS(O)2R13, -C(O)NR12R12또는 -NHS(O)2R13이고; m'은 2또는 3이고; p'은 0또는 1이고; m+p는 1내지 5이고; 나머지 치환체들은 제1항에서 정의한 바와 같다.
  5. 제4항에 있어서, m'이 0이 일반식(Ia)의 화합물 및 이의 약제학적으로 허용되는 염.
  6. 제4항에 있어서, Q1에 대해 α위치에 존재하는 탄소 원자가 저급 알킬-치환된 일반식(Ia)의 화합물 및 이의 약제학적으로 허용되는 염.
  7. 제1항에 있어서, 하기 일반식(Ib)의 화합물 및 이의 약제학적으로 허용되는 염:
    (Ib)
    상기식에서, R1은 H, 할로겐, CF3또는 CN이고; R22는 R3, -CH2OR3또는 -CH2SR2이고; Q1은 -C(O)OH, 1H(또는 2H)-테트라졸-5-일, -C(O)NHS(O)2R13, -C(O)NR12R12또는 -NHS(O)2R13이고; m은 0,2 또는 3이고; p는 0또는 1이고; p'은 1내지 4이고; m+p는 0내지 4이고; 나머지 치환체들은 제1항에서 정의한 바와 같다.
  8. 제8항에 있어서, 하기 일반식(I′)의 화합물 및 이의 약제학적으로 허용되는 염.
    (I')
    상기식에서, 치환체들은 하기와 같다 :
  9. 치료학적 유효량의 제1항에 따른 일반식(I)의 화합물 및 약제학적으로 허용되는 담체를 포함하는 약제학적 조성물.
  10. 제9항에 있어서, 비-스테로이드성 소염제; 말초 진통제; 사이클로옥시게나제 억제제; 류코트리엔 길항제; 류코트리엔 생합성 억제제; H2-수용체 길항제; 항히스타민제; 프로스타글란딘 길항제; 트롬복산 길항제; 트롬복산 신테타제 억제제; 및 ACE길항제 중에서 선택된 제2활성성분 유효량을 추가로 포함하는 약제학적 조성물.
  11. 제10항에 있어서, 제2활성성분이 비-스테로이드성 소염제인 약제학적 조성물.
  12. 제11항에 있어서, 제2활성성분에 대한 제1항의 화합물의 중량비가 약1000 ; 1내지 1 : 1000인 약제학적 조성물.
  13. 유효량의 제1항의 화합물을 포유동물에 투여함을 특징으로 하여, 포유동물에서 SRS-A 또는 류코트리엔의 합성, 작용 또는 억제하는 방법.
  14. 제13항에 있어서, 포유동물이 사람인 방법.
  15. 천식 치료를 필요로 하는 포유 동물에게 치료학적 유효량의 제1항의 화합물을 투여함을 특징으로 하여, 포유동물의 천식을 치료하는 방법.
  16. 염증성 안 질환의 치료를 필요로 하는 포유동물에게 치료학적 유효량의 제1항의 화합물을 투여함을 특징으로 하여, 포유동물의 염증성 안 질환을 치료하는 방법.
  17. 제16항에 있어서, 포유동물이 사람인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910017953A 1990-10-12 1991-10-12 류코트리엔 길항제로서의 불포화 하이드록시알킬퀴놀린산 및 이를 함유하는 약제학적 조성물 KR100227716B1 (ko)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US59688790A 1990-10-12 1990-10-12
US7/596,887 1990-10-12
US07/596,887 1990-10-12
US74188891A 1991-08-08 1991-08-08
US07/741,888 1991-08-08
US7/741,888 1991-08-08

Publications (2)

Publication Number Publication Date
KR920008006A true KR920008006A (ko) 1992-05-27
KR100227716B1 KR100227716B1 (ko) 1999-11-01

Family

ID=27082671

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019910017953A KR100227716B1 (ko) 1990-10-12 1991-10-12 류코트리엔 길항제로서의 불포화 하이드록시알킬퀴놀린산 및 이를 함유하는 약제학적 조성물

Country Status (27)

Country Link
EP (1) EP0480717B1 (ko)
JP (1) JP2501385B2 (ko)
KR (1) KR100227716B1 (ko)
CN (1) CN1046711C (ko)
AT (1) ATE165088T1 (ko)
CA (1) CA2053209C (ko)
CY (1) CY2094B1 (ko)
CZ (1) CZ281274B6 (ko)
DE (2) DE69129257T2 (ko)
DK (1) DK0480717T3 (ko)
ES (1) ES2114882T3 (ko)
FI (2) FI104897B (ko)
HK (1) HK1027473A1 (ko)
HR (1) HRP930751B1 (ko)
HU (2) HU222344B1 (ko)
IE (1) IE913609A1 (ko)
IL (3) IL99726A (ko)
LU (1) LU90284I2 (ko)
LV (1) LV12187B (ko)
MX (1) MX9101551A (ko)
NL (1) NL990009I2 (ko)
NO (1) NO914004D0 (ko)
NZ (1) NZ240194A (ko)
PT (1) PT99213B (ko)
SI (1) SI9111647B (ko)
SK (1) SK279944B6 (ko)
YU (1) YU48742B (ko)

Families Citing this family (91)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5270324A (en) * 1992-04-10 1993-12-14 Merck Frosst Canada, Inc. Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists
CA2111372C (en) * 1992-12-22 2007-01-16 Robert N. Young Diaryl 5,6-fusedheterocyclic acids as leukotriene antagonists
US5472964A (en) * 1992-12-22 1995-12-05 Merck Frosst Canada, Inc. Diaryl 5,6-fused heterocyclic acids as leukotriene antagonists
US5438141A (en) * 1993-05-21 1995-08-01 Merck Frosst Canada, Inc. Heteroaryl and haloaryl quinoline derivatives of cyclopropaneacetic acid as leukotriene antagonists
ES2080656B1 (es) * 1993-07-19 1996-10-16 Merck Frosst Canada Inc Acidos de hidroxialquilquinolina fluorados como antagonistas del leucotrieno.
CA2130723C (en) * 1993-09-03 2006-01-31 Wilhelm Quittmann Process for preparing y-mercaptocarboxylic acid derivatives
DE4339724C1 (de) * 1993-11-22 1995-01-19 Siemens Ag Gasarmatur
TW448160B (en) * 1993-12-28 2001-08-01 Merck & Co Inc Novel dicyclohexylamine salt and process for the preparation of leukotriene antagonists
CA2145735A1 (en) * 1994-04-21 1995-10-22 Paul Hanselmann Process for producing 5-oxaspiro[2.4]heptan-6-one and novel intermediate products obtained therein
US5523477A (en) * 1995-01-23 1996-06-04 Merck & Co., Inc. Process for the preparation of 1-(thiomethyl)-cyclopropaneacetic acid
US5750539A (en) * 1995-06-07 1998-05-12 Merck Frosst Canada Heteroaryl diol acids as leukotriene antagonists
US5714488A (en) * 1995-10-03 1998-02-03 Abbott Laboratories Bis-heteroarylylmethoxyphenyl ketone derivatives as inhibitors of leukotriene biosynthesis
US5668150A (en) * 1996-07-26 1997-09-16 Abbott Laboratories Non-symmetrical bis-heteroarylmethoxyphenylalkyl carboxylates as inhibitors of leukotriene biosynthesis
FR2751969B1 (fr) * 1996-08-01 1998-12-04 Centre Nat Rech Scient Composes activateurs du canal cftr, et compositions pharmaceutiques les contenant
US6262066B1 (en) 1998-07-27 2001-07-17 Schering Corporation High affinity ligands for nociceptin receptor ORL-1
US6221880B1 (en) 1998-10-09 2001-04-24 Schering Corporation Composition and method for treating allergic diseases
IT1320162B1 (it) 2000-02-09 2003-11-18 Rotta Research Lab Derivati della tirosina ad attivita' anti leucotrienica, procedimentoper la loro preparazione e loro uso farmaceutico.
CA2371048C (en) 2002-02-06 2011-01-04 Delmar Chemicals Inc. Process for the preparation of 1-(mercaptomethyl)-cyclopropaneacetic acid
CN1318400C (zh) * 2002-02-06 2007-05-30 戴尔玛化学品股份有限公司 制备1－(巯基甲基)－环丙烷乙酸的方法
AU2003209043A1 (en) * 2002-02-07 2003-09-02 Dr. Reddy's Laboratories Ltd. Novel anhydrous amorphous forms of montelukast sodium salt
US8450491B2 (en) 2003-06-06 2013-05-28 Morepen Laboratories Limited Method for the preparation of montelukast acid and sodium salt thereof in amorphous form
EP1678139B1 (en) 2003-10-10 2011-08-31 Synhton B.V. Solid-state montelukast
EP1709001A2 (en) * 2004-01-28 2006-10-11 Pliva Istrazivanje i Razvoj d.o.o. Solid forms of montelukast acid
US20050187243A1 (en) * 2004-01-30 2005-08-25 Valerie Niddam-Hildesheim Montelukast free acid polymorphs
EP1760077A1 (en) * 2004-01-30 2007-03-07 Teva Pharmaceutical Industries Ltd. Montelukast free acid polymorphs
BRPI0506610A (pt) * 2004-02-03 2007-05-02 Chemagis Ltd montelucaste sódico amorfo, processo de preparação de montelucaste sódico amorfo, composição farmacêutica, método de tratamento utilizando a administração de montelucaste sódico amorfo, co-precipitado amorfo de montelucaste sódico e processo de preparação de co-precipitado amorfo de montelucaste sódico
MXPA06012220A (es) * 2004-04-21 2007-07-18 Teva Pharma Procesos para preparar sodio de montelukast.
US7501517B2 (en) 2004-04-30 2009-03-10 Synthon Ip, Inc. Process for making montelukast and intermediates therefor
US7829716B2 (en) 2004-04-30 2010-11-09 Synthon Pharmaceuticals, Inc. Process for making montelukast and intermediates therefor
WO2006008750A2 (en) 2004-07-19 2006-01-26 Matrix Laboratories Ltd Methyl 2-[(3s)-[3-[(2e)-(7-chloro quinolin-2-yl) ethenyl] phenyl]-3-halopropyl] benzoates
US20090143590A1 (en) * 2004-07-19 2009-06-04 Matrix Laboratories Ltd. Process for the Preparation of Montelukast and its Salts
WO2006008562A1 (en) * 2004-07-23 2006-01-26 Pliva-Istrazivanje I Razvoj D.O.O. Process
WO2006021974A1 (en) * 2004-08-23 2006-03-02 Morepen Laboratories Limited A process for synthesizing diol (viii)-an intermediate of montelukast sodium
PL205637B1 (pl) * 2004-10-22 2010-05-31 Inst Farmaceutyczny Sposób wytwarzania kwasu (R,E)-(1-{1-{3-[2-(7-chlorochinolin-2-ylo)etenylo]fenylo}-3-[2-(1-hydroksy-1-metyloetylo)fenylo] propylosulfanylometylo}cyklopropylo)octowego i/lub jego farmaceutycznie dopuszczalnych soli
US20080214822A1 (en) * 2004-11-30 2008-09-04 Medichem, S.A. Process For the Preparation of a Leukotriene Antagonist
WO2006131782A1 (en) * 2005-06-07 2006-12-14 Glade Organics Private Limited Process for the manufacture of methyl-2-(3-(2-(7-chloro-2-quinolinyl-ethenyl)-phenyl)-3-oxopropyl) benzoate
US7812168B2 (en) 2005-07-05 2010-10-12 Teva Pharmaceutical Industries Ltd. Purification of montelukast
US20070161796A1 (en) * 2005-11-16 2007-07-12 Ilan Kor-Sade Drying methods of montelukast sodium by azeotropic removal of the solvent
AR057908A1 (es) 2005-11-18 2007-12-26 Synthon Bv Proceso para preparar montelukast e intermediarios del mismo
EP1968943B1 (en) 2005-12-13 2013-01-23 MSN Laboratories Limited An improved process for the preparation of montelukast and its pharmaceutically acceptable salts
US7572930B2 (en) 2006-02-02 2009-08-11 Chemagis Ltd. Process for preparing 1-(mercaptomethyl)cyclopropaneacetic acid, a useful intermediate in the preparation of montelukast and salts thereof
WO2007096889A2 (en) 2006-02-27 2007-08-30 Chemagis Ltd. Process for preparing montelukast and salts thereof
EP2004609A2 (en) * 2006-03-06 2008-12-24 Farmaprojects, S.A. Process for preparing a leukotriene antagonist
EP1996552A1 (en) 2006-03-17 2008-12-03 Synthon B.V. Montelukast amantadine salt
CA2649189A1 (en) 2006-04-12 2007-10-18 Glade Organics Private Limited An improved process for the manufacture of montelukast sodium
US20060223999A1 (en) * 2006-05-10 2006-10-05 Chemagis Ltd. Process for preparing montelukast and precursors thereof
GB0614485D0 (en) * 2006-07-21 2006-09-27 Pliva Istrazivanje I Razvoj D Process
EP1886998A1 (en) * 2006-08-09 2008-02-13 Esteve Quimica, S.A. Purification process of montelukast and its amine salts
GB0618703D0 (en) * 2006-09-22 2006-11-01 Almac Sciences Ltd Synthesis of leikotriene compounds
US7700776B2 (en) 2006-10-24 2010-04-20 Formosa Laboratories, Inc. Compounds and preparation for montelukast sodium
WO2008062478A2 (en) 2006-11-20 2008-05-29 Manne Satyanarayana Reddy Improved process for pure montelukast sodium through pure intermediates as well as novel amine salts
US7271268B1 (en) 2006-12-22 2007-09-18 Formosa Laboratories Inc. Process for preparation of [1-(mercaptomethyl)cyclopropyl]acetic acid and related derivatives
EP1958936A1 (en) * 2007-02-14 2008-08-20 Inke, S.A. Process for obtaining montelukast
EP1988079A1 (en) * 2007-04-25 2008-11-05 Lonza Ag Process for the preparation of optically active ethenylphenyl-alcohols
PL205444B1 (pl) 2007-05-02 2010-04-30 Zak & Lstrok Ady Farmaceutyczn Sposób wytwarzania soli sodowej kwasu 1-(((1(R)-(3-(2-(7--chloro-2- chinolinylo)-etenylo)fenylo)-3-(2-(1-hydroksy-1- metyloetylo)fenylo)propylo)sulfanylo)metylo)-cyklopropanooctowego
ES2320077B1 (es) 2007-07-31 2010-02-26 Moehs Iberica, S.L. Proceso de preparacion de un antagonista de leucotrienos y de un intermedio del mismo.
KR101072896B1 (ko) 2007-10-09 2011-10-17 한미홀딩스 주식회사 이온성 액체 매개체를 이용한 몬테루카스트산의 제조 방법
EP2053043A1 (en) 2007-10-26 2009-04-29 Inke, S.A. Crystalline salt of montelukast
DE102007061630B4 (de) 2007-12-20 2013-07-04 Formosa Laboratories, Inc. Neue Verbindungen und Herstellung von Montelukast-Natrium
CN101817818B (zh) * 2008-03-06 2011-10-26 台耀化学股份有限公司 一种用于制备孟鲁司特钠的化合物
ES2605473T3 (es) 2008-05-26 2017-03-14 Laurus Labs Private Limited Un procedimiento mejorado para la preparación de Montelukast y sus sales
TR200806298A2 (tr) 2008-08-22 2010-03-22 Bi̇lgi̇ç Mahmut Farmasötik formülasyon
KR101123292B1 (ko) * 2008-09-26 2012-03-19 주식회사 엘지생명과학 몬테루카스트 나트륨염의 제조방법
WO2010064109A2 (en) 2008-12-02 2010-06-10 Mayuka Labs Private Limited An improved process for the preparation of montelukast sodium and its intermediates
WO2010107404A1 (en) 2009-03-16 2010-09-23 Mahmut Bilgic Stable pharmaceutical combinations
AR077101A1 (es) 2009-06-16 2011-08-03 Schering Corp Esteroides de heteroarilo (3,2-c), como agonistas de receptor glucocorticoide, composiciones y usos de los mismos
WO2011004298A1 (en) 2009-07-09 2011-01-13 Alembic Limited Montelukast hexamethylenediamine salt and its use for the preparation of montelukast sodium
EP2287154A1 (en) 2009-07-14 2011-02-23 KRKA, D.D., Novo Mesto Efficient synthesis for the preparation of montelukast
CN101638381B (zh) * 2009-09-02 2012-08-29 鲁南制药集团股份有限公司 孟鲁司特钠中间体的合成方法
EP2486015A1 (en) 2009-10-09 2012-08-15 DSM IP Assets B.V. Sythesis of optically active intermediate for the preparation of montelukast
US20120259121A1 (en) 2009-12-23 2012-10-11 Pharmathen S.A. Process for the preparation of montelukast and salts thereof
WO2011121091A1 (en) 2010-03-31 2011-10-06 Krka, D.D., Novo Mesto Efficient synthesis for the preparation of montelukast and novel crystalline form of intermediates therein
KR100990046B1 (ko) * 2010-07-30 2010-10-26 동국제약 주식회사 신규한 몬테루카스트 4-할로 벤질아민염 및 이를 이용한 몬테루카스트 나트륨염의 제조방법
HUP1000425A2 (en) 2010-08-11 2012-03-28 Richter Gedeon Nyrt Process for the production of montelukast sodium
TR201009394A2 (tr) 2010-11-11 2012-06-21 Bi̇lgi̇ç Mahmut Geliştirilmiş montelukast formülasyonları.
TR201009398A2 (tr) 2010-11-11 2012-05-21 Bi̇lgi̇ç Mahmut Fiziksel özellikleri geliştirilmiş tablet formülasyonları
US8471030B2 (en) 2010-12-06 2013-06-25 Orochem Technologies Inc. Purification of montelukast using simulated moving bed
EP2502910A1 (en) 2011-03-15 2012-09-26 Laboratorios Lesvi, S.L. Camphorsulfonic salt of a key Montelukast intermediate
CN102690229B (zh) * 2011-03-23 2016-06-08 上海相辉医药科技有限公司 一种孟鲁司特钠的合成及其制备中间体
AU2012320010B2 (en) * 2011-07-26 2017-03-30 Sun Pharma Advanced Research Company Ltd. Quinoline-, quinoxaline or benzothiazole based cysteinyl leukotriene antagonists (LTD4)
WO2013077829A1 (en) 2011-11-21 2013-05-30 Mahmut Bilgic Water-soluble pharmaceutical granules
WO2014118796A1 (en) 2013-01-31 2014-08-07 Melody Healthcare Pvt. Ltd. An in-situ process for the preparation of highly pure montelukast sodium
CN104109122B (zh) * 2013-04-16 2017-03-29 浙江奥翔药业股份有限公司 用于合成孟鲁司特的中间体化合物及其制备方法
CN104370810B (zh) * 2013-08-13 2016-10-05 天津汉瑞药业有限公司 孟鲁司特钠化合物
CN103554017B (zh) * 2013-10-25 2014-12-17 河北序能生物技术有限公司 一种孟鲁司特钠手性中间体的制备方法
CN103936671B (zh) * 2014-05-06 2015-10-28 启东东岳药业有限公司 孟鲁司特钠中间体的制备方法
CN105294556A (zh) * 2014-06-06 2016-02-03 上海迪赛诺化学制药有限公司 一种制备孟鲁司特酸的方法
CN105085391B (zh) 2015-06-10 2017-08-22 广东默泰同创医药科技有限公司 用作白三烯受体拮抗剂的环丙基不饱和喹啉化合物及应用
CN108273039B (zh) * 2015-12-16 2021-04-30 新乡医学院第一附属医院 一种治疗溶血性贫血的药物组合物及其应用
CN108530355B (zh) * 2018-06-08 2019-09-10 福州华博立乐新材料科技有限公司 一种3-[2-(7-氯-2-喹啉基)乙烯基]苯甲醛的合成方法
CN108435257A (zh) * 2018-06-08 2018-08-24 福州华博立乐新材料科技有限公司 一种用于合成3-[2-(7-氯-2-喹啉基)乙烯基]苯甲醛的催化剂

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0206751A3 (en) * 1985-06-18 1988-05-25 Merck Frosst Canada Inc. 2-substituted quinolines, their preparation and use
IE59889B1 (en) * 1986-02-14 1994-04-20 Merck Frosst Canada Inc 2-substituted quinoline dioic acids
US4851409A (en) * 1986-02-14 1989-07-25 Merck Frosst Canada Inc. 2-substituted quinoline dioic acids and pharmaceutical compositions
JPS62258362A (ja) * 1986-05-02 1987-11-10 Terumo Corp アミド誘導体およびこれを含有する５−リポキシゲナ−ゼ作用阻害剤
EP0271287A3 (en) * 1986-12-11 1990-06-13 Merck Frosst Canada Inc. Quinoline dioic acids and amides
EP0318093A3 (en) * 1987-11-25 1990-12-05 Merck Frosst Canada Inc. Diarylquinoline diacids and their use as medicaments
NZ233752A (en) * 1989-05-24 1993-05-26 Merck Frosst Canada Inc Substituted quinoline derivatives, preparation and pharmaceutical compositions thereof
WO1990015801A1 (en) * 1989-06-22 1990-12-27 Pfizer Inc. Substituted sulfonamides and related compounds in the treatment of asthma, arthritis and related diseases

Also Published As

Publication number Publication date
HU211294A9 (en) 1995-11-28
DE19875039I2 (de) 2003-05-22
AU639610B2 (en) 1993-07-29
HRP930751A2 (en) 1995-06-30
KR100227716B1 (ko) 1999-11-01
JPH05105665A (ja) 1993-04-27
ES2114882T3 (es) 1998-06-16
IL117147A (en) 2000-10-31
SK279944B6 (sk) 1999-06-11
NL990009I2 (nl) 1999-07-01
FI914796A (fi) 1992-04-13
LU90284I2 (fr) 1998-11-03
CN1061407A (zh) 1992-05-27
HK1027473A1 (en) 2001-01-12
SI9111647A (en) 1997-12-31
ATE165088T1 (de) 1998-05-15
NZ240194A (en) 1995-03-28
IL99726A (en) 1998-02-22
PT99213A (pt) 1992-09-30
LV12187A (lv) 1998-12-20
CN1046711C (zh) 1999-11-24
AU8579491A (en) 1992-04-16
IE913609A1 (en) 1992-04-22
HU913217D0 (en) 1992-01-28
YU48742B (sh) 1999-09-27
FI20000250A (fi) 2000-02-07
HUT61981A (en) 1993-03-29
JP2501385B2 (ja) 1996-05-29
NO914004D0 (no) 1991-10-11
EP0480717B1 (en) 1998-04-15
DE69129257D1 (de) 1998-05-20
CA2053209C (en) 1998-12-08
DK0480717T3 (da) 1999-02-08
MX9101551A (es) 1992-06-05
IL117147A0 (en) 1996-06-18
SI9111647B (en) 2001-06-30
NL990009I1 (nl) 1999-06-01
PT99213B (pt) 1999-01-29
CA2053209A1 (en) 1992-04-13
LV12187B (en) 1999-02-20
IL99726A0 (en) 1992-08-18
DE69129257T2 (de) 1998-11-05
HU222344B1 (hu) 2003-06-28
HRP930751B1 (en) 2000-06-30
EP0480717A1 (en) 1992-04-15
FI104897B (fi) 2000-04-28
CZ281274B6 (cs) 1996-08-14
CS309591A3 (en) 1992-04-15
CY2094B1 (en) 2002-04-05
FI914796A0 (fi) 1991-10-11
YU164791A (sh) 1994-04-05

Similar Documents

Publication Publication Date Title
KR920008006A (ko) 류코트리엔 길항제로서의 불포화 하이드록시 알킬퀴놀린산
KR920008004A (ko) 류코트리엔 길항제로서의 포화하이드록시알킬 퀴놀린산
ES8204739A1 (es) Un procedimiento para preparar compuestos de cefem
DK116480A (da) Fremgangsmaade til fremstilling af substituerede chromoner
DK160877C (da) Fremgangsmaade til fremstilling af 2-penemforbindelser
ZA804146B (en) 2-alkoxyphenyl-imidazo(4,5-b)pyridines, processes for their proparation, pharmaceutical compositions and use thereof
KR940014384A (ko) 항바이러스제로서의 페녹시- 및 페녹시알킬-피페리딘
KR920008005A (ko) 류코트리엔 길항제로서의 하이드록시 알킬퀴놀린 에테르 산
KR920016423A (ko) 루코트리엔 길항제로서의 퀴놀린-함유 케토산
ES502264A0 (es) Procedimiento de preparacion de nuevos derivados de acido 4-hidroxi-3-quinolein-carboxilico,sustituidos en posicion 2
SE8006365L (sv) Cyklohexankarboxylsyraderivat
NO832828L (no) Fremgangsmaate ved fremstilling av nye cefalosporinforbindelser
KR940011450A (ko) 살진균성 2-알콕시-2-이미다졸린-5-온 유도체
IE44765L (en) N-substituted benzamides.
SE7907953L (sv) Substituerade furaner
KR930021638A (ko) 이미다조피리딘
ES519606A0 (es) Procedimiento para la preparacion de nuevas piridobenzodiazepinonas.
DE69001004D1 (de) Zusammensetzung gegen leberkrankheiten.
GB1008470A (en) New cyanacetamide derivatives
JPS5754175A (ja) Shinkina33aminoindazoorujudotai
ATE92496T1 (de) Pradimicin-derivate.
DE3068456D1 (en) 2-(n-(2-fluoro-6-bromophenyl)-n-(thiemyl-2-methyl)-amino)-2-imidazoline, its addition salts, pharmaceutical compositions containing them and processes for their preparation
SE7910387L (sv) 7alfa-metoxicefalosporinderivat och forfarande for framstellning derav
SE8003476L (sv) Isokinolinderivat
MC1555A1 (fr) Dérivés de l'acridanone

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
N231 Notification of change of applicant
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20050330

Year of fee payment: 12

EXPY Expiration of term