KR890012983A - 강심제 알카노일 및 아로일 옥사졸론 - Google Patents
강심제 알카노일 및 아로일 옥사졸론 Download PDFInfo
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- KR890012983A KR890012983A KR1019890001825A KR890001825A KR890012983A KR 890012983 A KR890012983 A KR 890012983A KR 1019890001825 A KR1019890001825 A KR 1019890001825A KR 890001825 A KR890001825 A KR 890001825A KR 890012983 A KR890012983 A KR 890012983A
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- -1 aroyl oxazolone Chemical compound 0.000 title claims 26
- 125000001589 carboacyl group Chemical group 0.000 title 1
- 230000002526 effect on cardiovascular system Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 18
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 11
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 11
- 125000004414 alkyl thio group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000002883 imidazolyl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims 4
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000001725 pyrenyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- ATAHUPIWBCIFEH-UHFFFAOYSA-N 5-(4-imidazol-1-ylbenzoyl)-4-methyl-3h-1,3-oxazol-2-one Chemical compound N1C(=O)OC(C(=O)C=2C=CC(=CC=2)N2C=NC=C2)=C1C ATAHUPIWBCIFEH-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005594 diketone group Chemical group 0.000 claims 1
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
- C07D263/36—One oxygen atom
- C07D263/38—One oxygen atom attached in position 2
-
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (18)
- 하기 구조식 1의 화합물 및 이들의 제약학적으로 허용되는 염.상기 식중, Q 및 T는 각각 독립적으로 2가 황 또는 산소원자이고 ; R1은 수소 또는 (C1-C4)알킬기이며 ; R2는 (C1-C6)알킬이거나, 또는 R2는 (C1-C4)알킬, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 아미노, 모노 및 디(C1-C4)-알킬치환 아미노, (C2-C5)알카노일 아미노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸, 또는 이미다졸릴기 중 1개 또는 2개에 의해 임의로 치환된 페닐 또는 벤질기이거나, 또는 R2는 (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 카르복시, 카르브(C1-C4)알콕시,카르바미도, 트리플루오로메틸 또는 이미다졸릴기에 의해 임의로 치환된 피리딜이거나, 또는 R2는 하기 구조식(상기 식중, R'는 수소 또는 (C1-C4알킬기임)의 인돌-2-온이거나 또는 R2는 푸라닐, 티에닐 또는 피릴기이다.
- 제1항에 있어서, Q 및 T가 각각 2가 산소원자인 화합물.
- 제1항 또는 제2항중 하나의 항에 있어서, R2가 (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸 또는 이미다졸릴기 중 1개 또는 2개에 의해 임의로 치환된 페닐기인 화합물.
- 제3항에 있어서, R1이 메틸 또는 에틸기인 화합물.
- 제1항 또는 제2항중 하나의 항에 있어서, R2가 (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸 또는 이미다졸릴기에 의해 임의로 치환된 피리딜기인 화합물.
- 제5항에 있어서, R1이 메틸 또는 에틸기인 화합물.
- 제1항 또는 제2항중 하나의 항에 있어서, R2가 4-위치에서 (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸 또는 이미다졸릴기에 의해 임의로 치환된 페닐기인 화합물.
- 제1항 또는 제2항중 하나의 항에 있어서, R2가 이미다조일기에 의해 치환된 페닐기인 화합물.
- 제8항에 있어서, R1이 메틸 또는 에틸기인 화합물.
- 제1항 또는 제2항중 하나의 항에 있어서, R2가 4-위치에서 이미다조일기에 의해 치환된 페닐기인 화합물.
- 제10항에 있어서, R1이 메틸 또는 에틸기인 화합물.
- 제1항 또는 제2항중 하나의 항에 있어서, 5-[4-(1H-이미다졸-1-일)벤조일]-4-메틸-2(3H)옥사졸론인 화합물.
- 제1항 또는 제2항중 하나의 항에 있어서, R2가 (C1-C6)알킬기인 화합물.
- 제13항에 있어서, R1이 메틸 또는 에틸기인 화합물.
- 하기 구조식(2a)의 화합물을 (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸 또는 이미다졸릴기에 의해 임의로 치환된 푸라노일 할라이드, 티에노일 할라이드, 피롤릴 할라이드, 피리도오일 할라이드, 또는 (C1-C4)알킬기에 의해 임의로 치환된 (C2-C7)알카노일 할라이드, 또는 인돌-2-온오일 할라이드, 또는 (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 아미노, 모노 및 디(C1-C4)알킬치환아미노, (C2-C5)알카노일아미노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸 또는 이미다졸릴기 중의 1개 또는 2개에 의해 임의로 치환된 벤조일 할라이드 또는 벤질카르보닐 할라이드로 되는 군 중에서 선택된 아실화제와 반응시키는 것으로 되는, 하기 구조식(1)의 화합물의 제조방법.상기 식중, Q 및 T는 각각 독립적으로 2가 황 또는 산소원자이고 ; R1은 수소 또는 (C1-C4)알킬기이며 ; R2는 (C1-C6)알킬이거나, 또는 R2는 (C1-C4)알킬, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 아미노, 모노 및 디(C1-C4)-알킬치환아미노, (C2-C5)알카노일 아미노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸, 또는 이미다졸릴기 중 1개 또는 2개에 의해 임의로 치환된 페닐 또는 벤질기이거나, R2는 (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸 또는 이미다졸릴기에 의해 임의로 치환된 피리딜기이거나, 또는 R2는 하기 구조식(상기식중, R'는 수소 또는 (C1-C4알킬기임)의 인돌-2-온이거나 또는 R2는 푸라닐, 티에닐 또는 피릴기이다.
- (a)하기 구조식(Ⅲ)의 1,3-디케톤을 브롬화수소산과 반응시켜 하기 구조식(Ⅳ)의 2-브로모-1,3-디케톤을 생성하고, (b)2-브로모-1,3-디케톤을 아세트산 칼륨과 반응시켜 하기 구조식(Ⅴ)의 2-아세톡시-1,3-디케톤을 생성하고, (c)하기 구조식(Ⅴ)의 2-아세톡시-1,3-디케톤을 염산과 반응시켜 하기 구조식(Ⅳ)의 2-히드록시-1,3-디케톤을 생성하고, (d)구조식(Ⅵ)의 2-히드록시-1,3-디케톤을 티오시안산 칼륨과 반응시키는 것으로 되는, 하기 구조식(Ⅱ)의 화합물의 제조방법.상기식중, R1은 수소 또는 (C1-C4)알킬기이며, R2는 (C1-C6)알킬이거나, 또는 R2는 (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 할로겐, 시아노, 아미노, 모노 및 디(C1-C4)-알킬치환아미노, (C2-C5)알카노일 아미노, 카르복시, 카르브(C1-C4)알콕시, 카르바미도, 트리플루오로메틸, 또는 이미다졸릴기중 1개 또는 2개에 의해 임의로 치환된 페닐 또는 벤질기이거나, 또는 R2(C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알킬술피닐, (C1-C4)알킬술포닐, 히드록시, 카르바미도, 트리플루오로메틸 또는 이미다졸릴기에 의해 임의로 치환된 피리딜기이거나, 또는 R2는 하기 구조식(상기식중, R'는 수소 또는 (C1-C4알킬기임)의 인돌-2-온이거나 또는 R2는 푸라닐, 티에닐 또는 피릴기이다.
- 제15항의 방법에 의하여 제조한 화합물 중 T가 2가 산소원자인 화합물을 오황화인과 더 한층 반응시켜 T가 2가 황원자인 구조식 1의 화합물을 제조하는 방법.
- 제16항 방법에 의하여 제조한 화합물을 오황화인과 더 한층 반응시켜 T가 2가 황원자인 구조식 1의 화합물을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US157430 | 1988-02-18 | ||
| US07/157,430 US4866182A (en) | 1988-02-18 | 1988-02-18 | Cardiotonic alkanoyl and aroyl oxazolones |
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| Publication Number | Publication Date |
|---|---|
| KR890012983A true KR890012983A (ko) | 1989-09-20 |
| KR960014794B1 KR960014794B1 (en) | 1996-10-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR89001825A KR960014794B1 (en) | 1988-02-18 | 1989-02-17 | Cardiotonic alkanoyl and aroyl oxazolones |
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| Country | Link |
|---|---|
| US (1) | US4866182A (ko) |
| EP (1) | EP0329070B1 (ko) |
| JP (1) | JP2811577B2 (ko) |
| KR (1) | KR960014794B1 (ko) |
| CN (1) | CN1022035C (ko) |
| AT (1) | ATE99681T1 (ko) |
| AU (1) | AU614029B2 (ko) |
| CA (1) | CA1334201C (ko) |
| DE (1) | DE68911944T2 (ko) |
| DK (1) | DK74889A (ko) |
| ES (1) | ES2061748T3 (ko) |
| FI (1) | FI890694A (ko) |
| HU (1) | HU206880B (ko) |
| IL (1) | IL89302A (ko) |
| NO (1) | NO890681L (ko) |
| NZ (1) | NZ227977A (ko) |
| PH (1) | PH26260A (ko) |
| PT (1) | PT89749B (ko) |
| ZA (1) | ZA891111B (ko) |
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| US5437491A (en) * | 1994-04-07 | 1995-08-01 | Illinois Tool Works Inc. | Fuel door housing |
| DE4429461A1 (de) * | 1994-08-19 | 1996-02-22 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| ES2125161B1 (es) | 1996-03-21 | 1999-11-16 | Grupo Farmaceutico Almirall S | Nuevos derivados de 2-(3h)-oxazolona. |
| CN102993075A (zh) * | 2012-11-29 | 2013-03-27 | 江苏长青农化股份有限公司 | 硫脲类杀虫杀螨剂丁醚脲的合成工艺 |
| HUE045546T2 (hu) | 2015-06-03 | 2020-01-28 | Bristol Myers Squibb Co | 4-hidroxi-3-(heteroaril)piridin-2-on APJ agonisták felhasználásra cardiovascularis megbetegedések kezelésében |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3514465A (en) * | 1966-12-30 | 1970-05-26 | Degussa | Certain thiazolyl- and pyridinylaminoketones |
| US4303439A (en) * | 1979-10-01 | 1981-12-01 | Monsanto Company | 2-Substituted-4-alkyl or trihaloalkyl-5-oxazolecarboxylic acids as safening agents |
| JPS59100977A (ja) * | 1982-12-01 | 1984-06-11 | Omron Tateisi Electronics Co | 記録情報出力方法 |
| DE3246957A1 (de) * | 1982-12-18 | 1984-06-20 | Varta Batterie Ag, 3000 Hannover | Galvanisches element |
| DE3370170D1 (en) * | 1982-12-18 | 1987-04-16 | Rinninger Hans & Sohn | Paving block |
| US4623651A (en) * | 1985-10-15 | 1986-11-18 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic heterocyclocarbonyl- and acetyl-thiazolones |
| US4762849A (en) * | 1985-10-15 | 1988-08-09 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic alkanoylthiazolones |
| CA1266268C (en) * | 1985-10-15 | 1990-02-27 | CARDIOTONIC AROYLTHIAZOLONES | |
| US4670450A (en) * | 1985-11-13 | 1987-06-02 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic thiazolones |
| US4728661A (en) * | 1985-11-13 | 1988-03-01 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic phenyl oxazolones |
| US4689353A (en) * | 1986-02-21 | 1987-08-25 | The Dow Chemical Company | Hydroxy and amino-functional polyahls containing carbonate, urethane and/or urea moieties |
-
1988
- 1988-02-18 US US07/157,430 patent/US4866182A/en not_active Expired - Lifetime
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1989
- 1989-02-13 AU AU29906/89A patent/AU614029B2/en not_active Ceased
- 1989-02-13 ZA ZA891111A patent/ZA891111B/xx unknown
- 1989-02-14 DE DE68911944T patent/DE68911944T2/de not_active Expired - Fee Related
- 1989-02-14 AT AT89102496T patent/ATE99681T1/de not_active IP Right Cessation
- 1989-02-14 FI FI890694A patent/FI890694A/fi not_active Application Discontinuation
- 1989-02-14 EP EP89102496A patent/EP0329070B1/en not_active Expired - Lifetime
- 1989-02-14 NZ NZ227977A patent/NZ227977A/xx unknown
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- 1989-02-17 DK DK074889A patent/DK74889A/da not_active Application Discontinuation
- 1989-02-17 NO NO89890681A patent/NO890681L/no unknown
- 1989-02-17 PT PT89749A patent/PT89749B/pt not_active IP Right Cessation
- 1989-02-17 KR KR89001825A patent/KR960014794B1/ko not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| IL89302A0 (en) | 1989-09-10 |
| HU206880B (en) | 1993-01-28 |
| CN1036761A (zh) | 1989-11-01 |
| EP0329070B1 (en) | 1994-01-05 |
| AU2990689A (en) | 1989-08-24 |
| IL89302A (en) | 1993-02-21 |
| US4866182A (en) | 1989-09-12 |
| CA1334201C (en) | 1995-01-31 |
| JPH02149571A (ja) | 1990-06-08 |
| PH26260A (en) | 1992-04-01 |
| HUT54148A (en) | 1991-01-28 |
| DK74889A (da) | 1989-08-19 |
| JP2811577B2 (ja) | 1998-10-15 |
| NZ227977A (en) | 1990-10-26 |
| CN1022035C (zh) | 1993-09-08 |
| EP0329070A1 (en) | 1989-08-23 |
| AU614029B2 (en) | 1991-08-15 |
| FI890694A0 (fi) | 1989-02-14 |
| KR960014794B1 (en) | 1996-10-19 |
| ATE99681T1 (de) | 1994-01-15 |
| PT89749A (pt) | 1989-10-04 |
| DK74889D0 (da) | 1989-02-17 |
| PT89749B (pt) | 1994-03-31 |
| DE68911944D1 (de) | 1994-02-17 |
| ES2061748T3 (es) | 1994-12-16 |
| DE68911944T2 (de) | 1994-05-19 |
| FI890694A (fi) | 1989-08-19 |
| NO890681D0 (no) | 1989-02-17 |
| NO890681L (no) | 1989-08-21 |
| ZA891111B (en) | 1989-10-25 |
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