[go: up one dir, main page]

KR900011739A - β-차단/안기 오텐신 Ⅱ 차단 혈압강하제 혼합물 - Google Patents

β-차단/안기 오텐신 Ⅱ 차단 혈압강하제 혼합물 Download PDF

Info

Publication number
KR900011739A
KR900011739A KR1019900000556A KR900000556A KR900011739A KR 900011739 A KR900011739 A KR 900011739A KR 1019900000556 A KR1019900000556 A KR 1019900000556A KR 900000556 A KR900000556 A KR 900000556A KR 900011739 A KR900011739 A KR 900011739A
Authority
KR
South Korea
Prior art keywords
compound
formula
alkyl
preparing
reacting
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
KR1019900000556A
Other languages
English (en)
Other versions
KR920001672B1 (ko
Inventor
죤 카리니 데이비드
죠너스 바이터타스 던키아 죤
Original Assignee
도날드 에이. 호스
이. 아이. 듀 퐁 드 네모어 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 도날드 에이. 호스, 이. 아이. 듀 퐁 드 네모어 앤드 캄파니 filed Critical 도날드 에이. 호스
Publication of KR900011739A publication Critical patent/KR900011739A/ko
Application granted granted Critical
Publication of KR920001672B1 publication Critical patent/KR920001672B1/ko
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/68—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • C07D405/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • C07D409/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음

Description

β-차단/안기 오텐신 Ⅱ 차단 혈압강하제 혼합물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 골을 제거한 래트에서, 비히클-처리군과 실시예 1(3 및 30㎎/㎏ 정맥내)의, AⅡ에 대한 투여량-혈압상승반응을 비교한 그래프이다.

Claims (11)

  1. 다음 일반식(I)의 혈압강하제 화합물 및 이들 화합물의 약제학적으로 허용가능한 염:
    상기식에서, Q,Q1;Q2,Q4,Q5및 Q6은 독립적으로 수소 및 C1-4알킬 중에서 선택되며; P는 각각이 Ar에 결합된 N 및 O를 갖는 카보닐그룹 또는또는이고; B는 C1-6알킬그룹이며; -(CH2)c-그룹은 모두 독립적으로 임의로 1 또는 2개의 C1-4알킬에 의해 치환되고; Ar은 임의로 하나 이상의 할로겐원자에 의해 치환된 C1-4알킬그룹; C1-9알콕시, 할로겐, 니트로, 아미노, 카복시, C1-4알콕시카보닐 및 히드록시 중에서 독립적으로 선택된 하나 이상의 치환체에 의해 어떠한 위치에서라도 임의로 치환되는 벤젠환 또는 인돌릴환계이며;
    NHSO2CF3또는 NHOR9이고; R2는 H,F,Cl,Br,I,NO2, C1-6알킬, C1-6퍼플루오로알킬, 페닐, 펜타플루오로페닐, CN 또는 COR16이며; R3은 C2-10알킬, C3-10알케닐 또는 알키닐, 또는 C2-10알킬티오이고, R4는 H, Cl, Br, F, NO2, C1-4알킬, C1-4아실옥시, C1-4알콕시, CO2H, CO2R7, NHSO2CH3, NHSO2CF3, CONHOR9, SO2NH2, 아릴 또는 푸릴이며; R5는 H, Cl, Br, I, F, C1-4알킬 또는 C1-4알콕시이고;
    또는이며;
    R7은이고; R8은 H, C1-6알킬, C3-6시클로알킬, 페닐 또는 벤질이며; R9는 H, 메틸 또는 벤질이고; R11은 C1-6알킬, -NR12R|13또는이며; R12및 R13은 독립적으로, H, C1-6알킬 또는 벤질이거나, R12와 R13은 함께 (CH2)u를 형성하고, 여기에서 u는 3 내지 6이고; R14는 H, CH3또는 -C6H5이며; R15는 CN, NO2또는 CO2R8이고; R16은 H, C1-6알킬, 페닐; 알킬이 C1-6인 페닐알킬; OH, C1-6알콕시, 페녹시, 벤질옥시, NH2; 알킬이 C1-6인 알킬아미노 또는 디알킬아미노; 또는 모르폴리노이며; X는 C-C단일결합, -CO-, -O-, -S-, -NH-, -NHCO-, -CONH-, -OCH2-, -CH2O-, -CH=CH-, -SCH2-, -NHCH2-, -CH2-, -CH2S- 또는 -CH2NH-이고; Z는 O 또는 S이며; c는 1 내지 10이고; r은 0 내지 2이다.
  2. 제1항에 있어서, 5-〔4-(3-(N-이소프로필아미노)히드록시프로폭시)인돌-2-카복스아미도메틸〕-2-n-부틸-1-〔(2′-카복시비페닐-4-일)메틸〕-4-클로로이미다졸인 화합물.
  3. 약제학적으로 적합한 담체 및 제1항의 화합물을 함유하는 약제학적 조성물.
  4. 동물에게, 동물혈압을 강하시키기에 유효한 양의 제1항의 화합물을 투여하는 단계를 포함하여, 온혈동물의 고혈압을 치료하는 방법.
  5. 동물에게, 심장에 부담을 주는 혈액동력을 교정하여 충혈을 완화시키기에 유효한 양의 제1항의 화합물을 투여하는 단계를 포함하여, 온혈동물의 충혈성 심기능부전을 치료하는 방법:
  6. 제1항의 화합물을 제조하는 방법에 있어서, 둘다 적합하게 보호된 형태의 다음 일반식(1)의 화합물을 다음 일반식(2)와 반응시키는 단계를 포함하는 방법;
    상기식에서, Q, Q1, Q2, Q3, Q4, Q5, Q6, B, Ar, R1, R2, R3, c 및 r은 상기에서 정의한 바와같고; P1은 -COOH; -COCl 또는 -CO- 활성 에스테르와 같은 -COOH의 활성화된 유도체; 이소시아네이트(O=C=N-); 및 활성된 카바메이트 전구체 L=CO=O〔여기에서, L은 Cl 또는 N-이미다졸과 같은 활성화된 이탈기이다〕이다.
  7. 제1항의 화합물을 제조하는 방법에 있어서, (a) 둘다 적합하게 보호된 형태의 다음 일반식(3)의 화합물의 산소 음이온을 다음 일반식(4)의 화합물과 반응시켜 에폭시 에테르를 형성시킨 다음; (b)에폭시 에테르를 아민 HNQ-B〔여기에서, Q 및 B는 제1항에서 정의한 바와같다〕와 반응시키는 단계를 포함하는 방법;
    상기식에서, 상기식에서, Q, Q1, Q2, Q3, Q4, Q5, Q6, Ar, P, R1, R2, R3, c 및 r은 제1항에서 정의한 바와같고; X1은 이탈기이다.
  8. 제1항의 화합물을 제조하는 방법에 있어서, 다음 일반식(3)의 화합물의 산소 음이온을 다음 일반식(4a) 또는 (4b)의 화합물과 반응시켜 다음 일반식(5)의 화합물을 수득하는 단계를 포함하는 방법;
    상기식에서, Q, Q1, Q2, Q3, Q4, Q5, Q6, Ar, P, R1, R2, R3, c 및 r은 제1항에서 정의한 바와같고; D는 -N(Q)(P2)〔여기에서, P2는 보호기이다〕또는 -N3이다
  9. 제1항의 화합물을 제조하는 방법에 있어서, (a) 다음 일반식(3)의 화합물을 다음 일반식(4c)의 화합물과 반응시켜 다음 일반식(6)의 화합물을 형성시킨 다음; (b) 다음 일반식(6)의 화합물을 탈실릴화시키고 아민 HNQ-B〔여기에서, Q 및 B는 제1항에서 정의한 바와같다〕와 반응시킴으로써 다음 일반식(1a)의 화합물로 전환시키는 단계를 포함하는 방법;
    상기식에서, Ar, P, Q6, R1, R2, R3, c 및 r은 제1항에서 정의한 바와같고; Ms는 메실레이트이다.
  10. 제1항의 화합물을 제조하는 방법에 있어서, (a) 다음 일반식(3)의 화합물의 산호 음이온을 다음 일반식(4d)의 화합물과 반응시켜 다음 일반식(9) 또는 (11)의 화합물을 수득하고; (b) 다음 일반식(9)의 화합물이 단계(a)에서 형성된 경우에는 이 화합물을 다음 일반식(11)의 화합물로 전환시키고; (c) 다음 일반식(11)의 화합물을 아민 HNQ-B〔여기에서, Q 및 B는 제1항에서 정의한 바와같다〕와 반응시켜 다음 일반식(Ia)의 화합물을 제조하는 단계를 포함하는 방법:
    상기식에서, Q6, Ar, P, R1, R2, R3, c 및 r은 제1항에서 정의한 바와같고; Q1, Q2, Q3, Q4및 Q5는 수소이며; X1은 OH이다.
  11. 제1항의 화합물을 제조하는 방법에 있어서, 다음 일반식(3)의 화합물의 산소 음이온을 다음 일반식(15)의 옥사졸리디논과 반응시킨 다음 염기 가수분해시켜 다음 일반식(Ia)의 화합물을 수득하는 단계를 포함하는 방법;
    상기식에서, Ar, P, Q6, R1, R2, R3, B, c 및 r은 제1항에서 정의한 바와같고; Ms는 메실레이트이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900000556A 1989-01-19 1990-01-18 β-차단/안지오텐신 II차단 혈압강하제 화합물 Expired KR920001672B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US299709 1981-09-08
US299,709 1989-01-19
US07/299,709 US4916129A (en) 1989-01-19 1989-01-19 Combination β-blocking/angiotensin II blocking antihypertensives

Publications (2)

Publication Number Publication Date
KR900011739A true KR900011739A (ko) 1990-08-02
KR920001672B1 KR920001672B1 (ko) 1992-02-22

Family

ID=23155938

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019900000556A Expired KR920001672B1 (ko) 1989-01-19 1990-01-18 β-차단/안지오텐신 II차단 혈압강하제 화합물

Country Status (14)

Country Link
US (1) US4916129A (ko)
EP (1) EP0380959A1 (ko)
JP (1) JPH032169A (ko)
KR (1) KR920001672B1 (ko)
AU (1) AU618503B2 (ko)
CA (1) CA2006604A1 (ko)
FI (1) FI900294A7 (ko)
HU (1) HU205352B (ko)
IL (1) IL93105A (ko)
MY (1) MY104864A (ko)
NO (1) NO900264L (ko)
NZ (1) NZ232140A (ko)
PT (1) PT92897A (ko)
ZA (1) ZA90402B (ko)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2015812A1 (en) * 1989-05-02 1990-11-02 Shiro Nakayama Piezoelectric acceleration sensor and piezoelectric acceleration sensor device
IE70593B1 (en) * 1989-09-29 1996-12-11 Eisai Co Ltd Biphenylmethane derivative the use of it and pharmacological compositions containing same
CA2028925A1 (en) * 1989-11-06 1991-05-07 Gerald R. Girard Substituted n-(imidazolyl)alkyl alanine derivatives
US5073566A (en) * 1989-11-30 1991-12-17 Eli Lilly And Company Angiotensin ii antagonist 1,3-imidazoles and use thereas
PH30484A (en) * 1990-02-19 1997-05-28 Ciba Geigy Acy compounds pharmaceutical composition containing said compound and method of use thereof
US5179113A (en) * 1990-03-20 1993-01-12 E. I. Du Pont De Nemours And Company Treatment of central nervous disorders with imidazole compounds
US5210092A (en) * 1990-09-25 1993-05-11 Fujisawa Pharmaceutical Co., Ltd. Angiotensin ii antagonizing heterocyclic derivatives
DE4036706A1 (de) * 1990-11-17 1992-05-21 Hoechst Ag Verfahren zur behandlung der cardialen sowie der vasculaeren hypertrophie und hyperplasie
FI112942B3 (fi) 1991-02-21 2012-03-13 Daiichi Sankyo Co Ltd Menetelmä kohonneen verenpaineen hoitoon ja ennaltaehkäisyyn käyttökelpoisten 4'-(1H-imidatsol-1-yylimetyyli)-1,1' -bifenyylijohdannaisten valmistamiseksi
US5616599A (en) * 1991-02-21 1997-04-01 Sankyo Company, Limited Angiotensin II antagosist 1-biphenylmethylimidazole compounds and their therapeutic use
FR2673427B1 (fr) * 1991-03-01 1993-06-18 Sanofi Elf Derives heterocycliques diazotes n-substitues par un groupement biphenylmethyle, leur preparation, les compositions pharmaceutiques en contenant.
GB9110636D0 (en) * 1991-05-16 1991-07-03 Glaxo Group Ltd Chemical compounds
FR2677984B1 (fr) * 1991-06-21 1994-02-25 Elf Sanofi Derives d'imidazoline n-substitues, leur preparation, les compositions pharmaceutiques en contenant.
JPH06510763A (ja) * 1991-08-19 1994-12-01 イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー アンジオテンシン２受容体遮断イミダゾリノン誘導体
EP0599999A1 (en) * 1991-08-19 1994-06-08 E.I. Du Pont De Nemours And Company Angiotensin ii receptor blocking imidazolinone derivatives
US5256654A (en) * 1991-10-24 1993-10-26 American Home Products Corporation Substituted pyrrolopyrimidines, azepinopyrimidines and pyridopyrimidines useful as angiotensin II antagonists
US5149699A (en) * 1991-10-24 1992-09-22 American Home Products Corporation Substituted pyridopyrimidines useful as antgiotensin II antagonists
US5401851A (en) * 1992-06-03 1995-03-28 Eli Lilly And Company Angiotensin II antagonists
US5612360A (en) * 1992-06-03 1997-03-18 Eli Lilly And Company Angiotensin II antagonists
CA2111662C (en) * 1992-12-17 2004-11-23 Hiroaki Yanagisawa Biphenyl derivatives, their preparation and their use for the treatment of hypertension and cardiac disease
RU2123847C1 (ru) * 1994-03-16 1998-12-27 Санкио Компани Лимитед Лекарственное средство и способ лечения повышенного глазного давления и/или глаукомы
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
US7879802B2 (en) 2007-06-04 2011-02-01 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
AU2009256157B2 (en) 2008-06-04 2014-12-18 Bausch Health Ireland Limited Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
JP2011528375A (ja) 2008-07-16 2011-11-17 シナジー ファーマシューティカルズ インコーポレイテッド 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
AU2014235209B2 (en) 2013-03-15 2018-06-14 Bausch Health Ireland Limited Guanylate cyclase receptor agonists combined with other drugs
JP2016514671A (ja) 2013-03-15 2016-05-23 シナジー ファーマシューティカルズ インコーポレイテッド グアニル酸シクラーゼのアゴニストおよびその使用
AU2014274812B2 (en) 2013-06-05 2018-09-27 Bausch Health Ireland Limited Ultra-pure agonists of guanylate cyclase C, method of making and using same

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3705907A (en) * 1970-02-19 1972-12-12 Sandoz Ltd 4-(2-hydroxy)-3-aminopropoxy)-indole derivatives
JPS54148788A (en) * 1978-05-15 1979-11-21 Takeda Chem Ind Ltd 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative and its preparation
JPS5671073A (en) * 1979-11-12 1981-06-13 Takeda Chem Ind Ltd Imidazole derivative
JPS5671074A (en) * 1979-11-12 1981-06-13 Takeda Chem Ind Ltd 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative
JPS58157768A (ja) * 1982-03-16 1983-09-19 Takeda Chem Ind Ltd ４−クロロ−２−フエニルイミダゾ−ル−５−酢酸誘導体
PT78388B (en) * 1983-04-12 1986-09-15 Smithkline Beckman Corp Dopamine-beta-hydroxylase inhibitors
GB8422165D0 (en) * 1984-09-01 1984-10-03 Wellcome Found Compounds
CA1334092C (en) * 1986-07-11 1995-01-24 David John Carini Angiotensin ii receptor blocking imidazoles
ZA902794B (en) * 1989-04-18 1991-04-24 Duphar Int Res New 3-n substituted carbamoyl-indole derivatives

Also Published As

Publication number Publication date
NO900264L (no) 1990-07-20
AU618503B2 (en) 1991-12-19
MY104864A (en) 1994-06-30
AU4854590A (en) 1990-07-26
KR920001672B1 (ko) 1992-02-22
HU205352B (en) 1992-04-28
HUT53618A (en) 1990-11-28
NO900264D0 (no) 1990-01-18
NZ232140A (en) 1991-06-25
EP0380959A1 (en) 1990-08-08
JPH032169A (ja) 1991-01-08
PT92897A (pt) 1990-07-31
CA2006604A1 (en) 1990-07-19
US4916129A (en) 1990-04-10
HU900184D0 (en) 1990-03-28
FI900294A7 (fi) 1990-07-20
IL93105A0 (en) 1990-11-05
IL93105A (en) 1994-02-27
ZA90402B (en) 1991-09-25
FI900294A0 (fi) 1990-01-18

Similar Documents

Publication Publication Date Title
KR900011739A (ko) β-차단/안기 오텐신 Ⅱ 차단 혈압강하제 혼합물
KR910009692A (ko) 인돌 유도체
KR920701167A (ko) 약제학적 활성 화합물
KR960037673A (ko) 벤조퓨란
KR900701268A (ko) 헤테로사이클릭 펩타이드 레닌 억제제
RU99119545A (ru) Производные дитиолана, лекарственные средства
NO167917C (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive, nye derivater av ((4-(4-(4-fenyl-1-piperazinyl)fenoksymetyl)-1,3-dioksolan-2-yl)metyl)-1h-imidazoler og -1h-1,2,4-triazoler
US5137902A (en) 4-alkylimidazole derivatives and anti-hypertensive use thereof
KR870008873A (ko) 2-아졸릴메틸-2-아릴-1,3-디옥솔란 및 그의 제조방법
KR910015562A (ko) 뇌부전 질환치료용 약제, 신규 2-(1-피페라지닐)-4-페닐시클로알카노 피리미딘 유도체, 및 그의 제법
RU2221788C2 (ru) Оксоциклические соединения мочевины, фармацевтическая композиция, способ лечения
DE69017593D1 (de) Substituierte N-(Imidazolyl)alkyl-alanin-Derivate.
KR840006236A (ko) 디하이드로 피리딘의 제조방법
RU99101341A (ru) 4-оксоциклические соединения мочевины, фармацевтическая композиция, способ лечения
KR930004262A (ko) 메타노안트라센 화합물
ATE202342T1 (de) 5-(4-subst.-piperidinyl-1)-3-aryl-pentansäure derivate als tachykinin rezeptor antagonisten
DK484787A (da) Bis-dioxopiperazin-derivater
ES8203354A1 (es) Un procedimiento para la produccion de nuevos derivados heterociclicos,.
KR970074773A (ko) 신규한 항바이러스성 6-아릴옥시 및 6-아릴카르보닐 2, 4-피리미딘디온 유도체 및 그의 제조 방법
JP2002509144A5 (ko)
KR870011105A (ko) 1,3-치환된 이미다졸륨 염
RU2227740C2 (ru) Композиции, снижающие внутриглазное давление, для местного применения
KR930017896A (ko) 술포닐벤질 치환 이미다졸릴프로펜산 유도체
KR890016002A (ko) 항 고혈압성 설폰 아닐리드
FR1602627A (en) 3 omega-subst alkyl indoles

Legal Events

Date Code Title Description
A201 Request for examination
PA0109 Patent application

St.27 status event code: A-0-1-A10-A12-nap-PA0109

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

G160 Decision to publish patent application
PG1605 Publication of application before grant of patent

St.27 status event code: A-2-2-Q10-Q13-nap-PG1605

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U11-oth-PR1002

Fee payment year number: 1

LAPS Lapse due to unpaid annual fee
PC1903 Unpaid annual fee

St.27 status event code: A-4-4-U10-U13-oth-PC1903

Not in force date: 19950223

Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

PC1903 Unpaid annual fee

St.27 status event code: N-4-6-H10-H13-oth-PC1903

Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

Not in force date: 19950223

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000