KR900011739A - β-차단/안기 오텐신 Ⅱ 차단 혈압강하제 혼합물 - Google Patents
β-차단/안기 오텐신 Ⅱ 차단 혈압강하제 혼합물 Download PDFInfo
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- 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
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- 230000003276 anti-hypertensive effect Effects 0.000 title 1
- 230000000903 blocking effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 6
- 241001465754 Metazoa Species 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- -1 nitro, amino, carboxy Chemical group 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910004013 NO 2 Inorganic materials 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000004593 Epoxy Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 230000036772 blood pressure Effects 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- VGTOIASHMOKVPR-UHFFFAOYSA-N 2-[4-[[2-butyl-4-chloro-5-[[[4-[3-hydroxy-3-(propan-2-ylamino)propoxy]-1h-indole-2-carbonyl]amino]methyl]imidazol-1-yl]methyl]phenyl]benzoic acid Chemical compound CCCCC1=NC(Cl)=C(CNC(=O)C=2NC3=CC=CC(OCCC(O)NC(C)C)=C3C=2)N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O VGTOIASHMOKVPR-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 235000014653 Carica parviflora Nutrition 0.000 claims 1
- 241000243321 Cnidaria Species 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 241000700159 Rattus Species 0.000 description 1
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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Abstract
내용 없음
Description
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)
- 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.
- 제1항에 있어서, 5-〔4-(3-(N-이소프로필아미노)히드록시프로폭시)인돌-2-카복스아미도메틸〕-2-n-부틸-1-〔(2′-카복시비페닐-4-일)메틸〕-4-클로로이미다졸인 화합물.
- 약제학적으로 적합한 담체 및 제1항의 화합물을 함유하는 약제학적 조성물.
- 동물에게, 동물혈압을 강하시키기에 유효한 양의 제1항의 화합물을 투여하는 단계를 포함하여, 온혈동물의 고혈압을 치료하는 방법.
- 동물에게, 심장에 부담을 주는 혈액동력을 교정하여 충혈을 완화시키기에 유효한 양의 제1항의 화합물을 투여하는 단계를 포함하여, 온혈동물의 충혈성 심기능부전을 치료하는 방법:
- 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.
- 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.
- 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
- 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.
- 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.
- 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.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US299709 | 1989-01-19 | ||
| US07/299,709 US4916129A (en) | 1989-01-19 | 1989-01-19 | Combination β-blocking/angiotensin II blocking antihypertensives |
| US299,709 | 1989-01-19 |
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 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) | FI900294A0 (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 (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR940006950B1 (ko) * | 1989-05-02 | 1994-07-30 | 후지꾸라 가부시끼가이샤 | 압전형 가속도센서 및 압전형 가속도센서장치 |
| 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 |
| ATE134624T1 (de) * | 1990-02-19 | 1996-03-15 | Ciba Geigy Ag | Acylverbindungen |
| 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. |
| WO1993004046A1 (en) * | 1991-08-19 | 1993-03-04 | E.I. Du Pont De Nemours And Company | Angiotensin ii receptor blocking imidazolinone derivatives |
| WO1993004045A1 (en) * | 1991-08-19 | 1993-03-04 | 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 |
| US5612360A (en) * | 1992-06-03 | 1997-03-18 | Eli Lilly And Company | Angiotensin II antagonists |
| US5401851A (en) * | 1992-06-03 | 1995-03-28 | Eli Lilly And Company | Angiotensin II antagonists |
| JP3501484B2 (ja) * | 1992-12-17 | 2004-03-02 | 三共株式会社 | ビフェニル誘導体 |
| MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
| 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 |
| CA2726917C (en) | 2008-06-04 | 2018-06-26 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2010009319A2 (en) | 2008-07-16 | 2010-01-21 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| WO2014151200A2 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| JP6606491B2 (ja) | 2013-06-05 | 2019-11-13 | 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ｃの超高純度アゴニスト、その作成および使用方法 |
Family Cites Families (9)
| 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 |
-
1989
- 1989-01-19 US US07/299,709 patent/US4916129A/en not_active Expired - Fee Related
- 1989-12-22 CA CA002006604A patent/CA2006604A1/en not_active Abandoned
-
1990
- 1990-01-17 NZ NZ232140A patent/NZ232140A/en unknown
- 1990-01-17 EP EP90100874A patent/EP0380959A1/en not_active Withdrawn
- 1990-01-18 IL IL9310590A patent/IL93105A/en not_active IP Right Cessation
- 1990-01-18 JP JP2007287A patent/JPH032169A/ja active Pending
- 1990-01-18 FI FI900294A patent/FI900294A0/fi not_active Application Discontinuation
- 1990-01-18 PT PT92897A patent/PT92897A/pt not_active Application Discontinuation
- 1990-01-18 NO NO90900264A patent/NO900264L/no unknown
- 1990-01-18 KR KR1019900000556A patent/KR920001672B1/ko not_active IP Right Cessation
- 1990-01-18 HU HU90184A patent/HU205352B/hu not_active IP Right Cessation
- 1990-01-19 AU AU48545/90A patent/AU618503B2/en not_active Ceased
- 1990-01-19 MY MYPI90000092A patent/MY104864A/en unknown
- 1990-01-19 ZA ZA90402A patent/ZA90402B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2006604A1 (en) | 1990-07-19 |
| NO900264L (no) | 1990-07-20 |
| US4916129A (en) | 1990-04-10 |
| HU900184D0 (en) | 1990-03-28 |
| HUT53618A (en) | 1990-11-28 |
| FI900294A0 (fi) | 1990-01-18 |
| PT92897A (pt) | 1990-07-31 |
| HU205352B (en) | 1992-04-28 |
| NO900264D0 (no) | 1990-01-18 |
| IL93105A0 (en) | 1990-11-05 |
| ZA90402B (en) | 1991-09-25 |
| JPH032169A (ja) | 1991-01-08 |
| IL93105A (en) | 1994-02-27 |
| EP0380959A1 (en) | 1990-08-08 |
| KR920001672B1 (ko) | 1992-02-22 |
| NZ232140A (en) | 1991-06-25 |
| AU618503B2 (en) | 1991-12-19 |
| AU4854590A (en) | 1990-07-26 |
| MY104864A (en) | 1994-06-30 |
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