JPH0552813B2 - - Google Patents
Info
- Publication number
- JPH0552813B2 JPH0552813B2 JP63164713A JP16471388A JPH0552813B2 JP H0552813 B2 JPH0552813 B2 JP H0552813B2 JP 63164713 A JP63164713 A JP 63164713A JP 16471388 A JP16471388 A JP 16471388A JP H0552813 B2 JPH0552813 B2 JP H0552813B2
- Authority
- JP
- Japan
- Prior art keywords
- heart failure
- compound
- formula
- animals
- group
- 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.)
- Expired - Lifetime
Links
- 206010019280 Heart failures Diseases 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 description 15
- 230000002861 ventricular Effects 0.000 description 15
- 229940126062 Compound A Drugs 0.000 description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 210000004351 coronary vessel Anatomy 0.000 description 7
- QPNKYNYIKKVVQB-UHFFFAOYSA-N crotaleschenine Natural products O1C(=O)C(C)C(C)C(C)(O)C(=O)OCC2=CCN3C2C1CC3 QPNKYNYIKKVVQB-UHFFFAOYSA-N 0.000 description 7
- QVCMHGGNRFRMAD-XFGHUUIASA-N monocrotaline Chemical compound C1OC(=O)[C@](C)(O)[C@@](O)(C)[C@@H](C)C(=O)O[C@@H]2CCN3[C@@H]2C1=CC3 QVCMHGGNRFRMAD-XFGHUUIASA-N 0.000 description 7
- QVCMHGGNRFRMAD-UHFFFAOYSA-N monocrotaline Natural products C1OC(=O)C(C)(O)C(O)(C)C(C)C(=O)OC2CCN3C2C1=CC3 QVCMHGGNRFRMAD-UHFFFAOYSA-N 0.000 description 7
- 208000010125 myocardial infarction Diseases 0.000 description 6
- 230000035488 systolic blood pressure Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 230000003449 preventive effect Effects 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 3
- 208000006029 Cardiomegaly Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- 230000002685 pulmonary effect Effects 0.000 description 3
- 210000005241 right ventricle Anatomy 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 208000000924 Right ventricular hypertrophy Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JQVLCBFYULYLPO-UHFFFAOYSA-N 6-(1h-imidazol-2-ylmethyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid;hydrochloride Chemical compound Cl.C1CC2=CC(C(=O)O)=CC=C2CC1CC1=NC=CN1 JQVLCBFYULYLPO-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010039163 Right ventricular failure Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000007522 mineralic acids 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SLZHLQUFNFXTHB-UHFFFAOYSA-M sodium;5-butan-2-yl-5-ethyl-2-sulfanylidenepyrimidin-3-ide-4,6-dione Chemical compound [Na+].CCC(C)C1(CC)C([O-])=NC(=S)NC1=O SLZHLQUFNFXTHB-UHFFFAOYSA-M 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Treatment Of Sludge (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- External Artificial Organs (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63164713A JPH01104013A (ja) | 1987-07-01 | 1988-07-01 | 心不全予防治療剤 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16438787 | 1987-07-01 | ||
| JP62-164387 | 1987-07-01 | ||
| JP63164713A JPH01104013A (ja) | 1987-07-01 | 1988-07-01 | 心不全予防治療剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01104013A JPH01104013A (ja) | 1989-04-21 |
| JPH0552813B2 true JPH0552813B2 (https=) | 1993-08-06 |
Family
ID=15792156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63164713A Granted JPH01104013A (ja) | 1987-07-01 | 1988-07-01 | 心不全予防治療剤 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4933349A (https=) |
| EP (1) | EP0297593B1 (https=) |
| JP (1) | JPH01104013A (https=) |
| KR (1) | KR960007752B1 (https=) |
| AT (1) | ATE88634T1 (https=) |
| AU (1) | AU609834B2 (https=) |
| CA (1) | CA1309028C (https=) |
| DE (1) | DE3880564T2 (https=) |
| DK (1) | DK360388A (https=) |
| IL (1) | IL86846A (https=) |
| PH (1) | PH24636A (https=) |
| ZA (1) | ZA884697B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL91542A0 (en) * | 1988-10-06 | 1990-04-29 | Erba Carlo Spa | N-imidazolyl-and n-imidazolyl-methyl derivatives of substituted bicyclic compounds,their preparation and pharmaceutical compositions containing them |
| US5354770A (en) * | 1989-02-27 | 1994-10-11 | Daiichi Pharmaceutical Co., Ltd. | Using imidazolyl tetrahydronaphthalene carboxylic acids to inhibit restenosis |
| ZA901416B (en) * | 1989-02-27 | 1990-12-28 | Daiichi Seiyaku Co | Post-ptca restenosis inhibitor |
| CA2080130A1 (en) * | 1990-04-09 | 1991-10-10 | Satoshi Kitamura | Remedy for obstructive pulmonary diseases |
| WO2002039002A1 (en) * | 2000-11-07 | 2002-05-16 | Lozon Llc | Splicing device and method for sealing conduit spaces |
| US8764674B2 (en) * | 2012-03-08 | 2014-07-01 | Medtronic, Inc. | Heart sound monitoring of pulmonary hypertension |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH22076A (en) * | 1983-08-25 | 1988-05-20 | Daiichi Seiyaku Co | Benzocycloalkane derivative |
-
1988
- 1988-06-23 IL IL86846A patent/IL86846A/xx not_active IP Right Cessation
- 1988-06-28 CA CA000570611A patent/CA1309028C/en not_active Expired - Lifetime
- 1988-06-28 US US07/212,743 patent/US4933349A/en not_active Expired - Fee Related
- 1988-06-29 KR KR1019880007872A patent/KR960007752B1/ko not_active Expired - Lifetime
- 1988-06-30 AU AU18550/88A patent/AU609834B2/en not_active Ceased
- 1988-06-30 ZA ZA884697A patent/ZA884697B/xx unknown
- 1988-06-30 DE DE8888110501T patent/DE3880564T2/de not_active Expired - Fee Related
- 1988-06-30 AT AT88110501T patent/ATE88634T1/de not_active IP Right Cessation
- 1988-06-30 EP EP88110501A patent/EP0297593B1/en not_active Expired - Lifetime
- 1988-06-30 DK DK360388A patent/DK360388A/da not_active Application Discontinuation
- 1988-07-01 PH PH37175A patent/PH24636A/en unknown
- 1988-07-01 JP JP63164713A patent/JPH01104013A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| PH24636A (en) | 1990-08-17 |
| EP0297593A2 (en) | 1989-01-04 |
| ZA884697B (en) | 1989-03-29 |
| EP0297593A3 (en) | 1990-08-01 |
| AU1855088A (en) | 1989-01-05 |
| US4933349A (en) | 1990-06-12 |
| ATE88634T1 (de) | 1993-05-15 |
| DK360388A (da) | 1989-01-02 |
| EP0297593B1 (en) | 1993-04-28 |
| KR960007752B1 (ko) | 1996-06-12 |
| JPH01104013A (ja) | 1989-04-21 |
| KR890001540A (ko) | 1989-03-27 |
| DK360388D0 (da) | 1988-06-30 |
| DE3880564T2 (de) | 1993-08-12 |
| IL86846A (en) | 1992-03-29 |
| DE3880564D1 (de) | 1993-06-03 |
| AU609834B2 (en) | 1991-05-09 |
| CA1309028C (en) | 1992-10-20 |
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