CA2132981A1 - Phenol and pyridinol derivatives as lusitropic agents - Google Patents
Phenol and pyridinol derivatives as lusitropic agentsInfo
- Publication number
- CA2132981A1 CA2132981A1 CA002132981A CA2132981A CA2132981A1 CA 2132981 A1 CA2132981 A1 CA 2132981A1 CA 002132981 A CA002132981 A CA 002132981A CA 2132981 A CA2132981 A CA 2132981A CA 2132981 A1 CA2132981 A1 CA 2132981A1
- Authority
- CA
- Canada
- Prior art keywords
- naphthyl
- formula
- compound
- oxo
- tetrazolyl
- 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.)
- Abandoned
Links
- 230000003295 lusitropic effect Effects 0.000 title claims abstract description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title description 2
- 230000003205 diastolic effect Effects 0.000 claims abstract description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 3
- -1 5-tetrazolyl Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000010117 myocardial relaxation Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- XJQFJIRQMZZIOB-UHFFFAOYSA-N 6-(2-pentoxynaphthalen-1-yl)-3-(2H-tetrazol-5-yl)-1H-pyridin-2-one Chemical compound C(CCCC)OC1=C(C2=CC=CC=C2C=C1)C1=CC=C(C(N1)=O)C1=NN=NN1 XJQFJIRQMZZIOB-UHFFFAOYSA-N 0.000 claims 1
- ZBBCZHQAXDJXPG-UHFFFAOYSA-N 6-naphthalen-2-yl-3-(2H-tetrazol-5-yl)-1H-pyridin-2-one Chemical compound C1=C(C=CC2=CC=CC=C12)C1=CC=C(C(N1)=O)C1=NN=NN1 ZBBCZHQAXDJXPG-UHFFFAOYSA-N 0.000 claims 1
- OEFCBKWZTOGVSR-UHFFFAOYSA-N [1-(2,2-dimethylpropanoyloxymethyl)-6-naphthalen-1-yl-2-oxopyridin-3-yl]-ethoxyphosphinic acid Chemical compound CC(C)(C)C(=O)OCN1C(=O)C(P(O)(=O)OCC)=CC=C1C1=CC=CC2=CC=CC=C12 OEFCBKWZTOGVSR-UHFFFAOYSA-N 0.000 claims 1
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 230000002526 effect on cardiovascular system Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 101000922391 Amanita phalloides Cycloamanide C Proteins 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241001289435 Astragalus brachycalyx Species 0.000 description 1
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 description 1
- 108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 description 1
- 235000002917 Fraxinus ornus Nutrition 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000003540 papillary muscle Anatomy 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9203747A FR2689012A1 (fr) | 1992-03-27 | 1992-03-27 | Utilisation de composés aryliques dans le traitement d'affections cardio-vasculaires. |
| FR92/03747 | 1992-03-27 | ||
| PCT/GB1993/000615 WO1993019754A1 (en) | 1992-03-27 | 1993-03-25 | Phenol and pyridinol derivatives as lusitropic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2132981A1 true CA2132981A1 (en) | 1993-10-14 |
Family
ID=9428178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002132981A Abandoned CA2132981A1 (en) | 1992-03-27 | 1993-03-25 | Phenol and pyridinol derivatives as lusitropic agents |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0632724A1 (enExample) |
| JP (1) | JPH07508707A (enExample) |
| KR (1) | KR950700736A (enExample) |
| AU (1) | AU3764693A (enExample) |
| CA (1) | CA2132981A1 (enExample) |
| FR (1) | FR2689012A1 (enExample) |
| TW (1) | TW234086B (enExample) |
| WO (1) | WO1993019754A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2753722A1 (fr) * | 1996-09-26 | 1998-03-27 | Smithkline Beecham Lab | Procede de detection de modulateurs de relaxation cardiaque et modulateurs ainsi obtenus |
| TWI486165B (zh) | 2011-02-15 | 2015-06-01 | Univ China Medical | 用於抑制血管狹窄之醫藥組合物及萃取物與該等之應用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ234186A (en) * | 1989-07-07 | 1991-10-25 | Janssen Pharmaceutica Nv | Imidazo quinazolin-one derivatives and pharmaceutical compositions |
| AU642743B2 (en) * | 1990-05-21 | 1993-10-28 | Smith Kline & French Laboratories Limited | Phenol and pyridinol derivatives as pharmaceuticals |
| AU644016B2 (en) * | 1990-09-28 | 1993-12-02 | Smith Kline & French Laboratories Limited | Phenylpyridinol derivatives as medicaments |
-
1992
- 1992-03-27 FR FR9203747A patent/FR2689012A1/fr active Pending
-
1993
- 1993-03-25 JP JP5517196A patent/JPH07508707A/ja active Pending
- 1993-03-25 EP EP93906752A patent/EP0632724A1/en not_active Withdrawn
- 1993-03-25 WO PCT/GB1993/000615 patent/WO1993019754A1/en not_active Ceased
- 1993-03-25 AU AU37646/93A patent/AU3764693A/en not_active Abandoned
- 1993-03-25 CA CA002132981A patent/CA2132981A1/en not_active Abandoned
- 1993-04-09 TW TW082102673A patent/TW234086B/zh active
-
1994
- 1994-09-26 KR KR1019940703385A patent/KR950700736A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07508707A (ja) | 1995-09-28 |
| KR950700736A (ko) | 1995-02-20 |
| WO1993019754A1 (en) | 1993-10-14 |
| FR2689012A1 (fr) | 1993-10-01 |
| AU3764693A (en) | 1993-11-08 |
| EP0632724A1 (en) | 1995-01-11 |
| TW234086B (enExample) | 1994-11-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |