DE3305690A1 - Glycerinmononitrate zur behandlung der angina pectoris - Google Patents
Glycerinmononitrate zur behandlung der angina pectorisInfo
- Publication number
- DE3305690A1 DE3305690A1 DE19833305690 DE3305690A DE3305690A1 DE 3305690 A1 DE3305690 A1 DE 3305690A1 DE 19833305690 DE19833305690 DE 19833305690 DE 3305690 A DE3305690 A DE 3305690A DE 3305690 A1 DE3305690 A1 DE 3305690A1
- Authority
- DE
- Germany
- Prior art keywords
- nitrate
- glycerol
- gtn
- treatment
- oral
- 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.)
- Withdrawn
Links
- 206010002383 Angina Pectoris Diseases 0.000 title claims abstract description 12
- OTKCDFNVBPBSNB-UHFFFAOYSA-N nitric acid;propane-1,2,3-triol Chemical compound O[N+]([O-])=O.OCC(O)CO OTKCDFNVBPBSNB-UHFFFAOYSA-N 0.000 title 1
- HXWLJBVVXXBZCM-UHFFFAOYSA-N 2,3-dihydroxypropyl nitrate Chemical compound OCC(O)CO[N+]([O-])=O HXWLJBVVXXBZCM-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001990 intravenous administration Methods 0.000 claims abstract description 14
- QYZBMMOLPVKAPU-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl nitrate Chemical compound OCC(CO)O[N+]([O-])=O QYZBMMOLPVKAPU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 208000002815 pulmonary hypertension Diseases 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 229940079593 drug Drugs 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 44
- 241000282472 Canis lupus familiaris Species 0.000 description 21
- 241000700159 Rattus Species 0.000 description 21
- 230000000694 effects Effects 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- 239000003826 tablet Substances 0.000 description 13
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 11
- 102000002852 Vasopressins Human genes 0.000 description 11
- 108010004977 Vasopressins Proteins 0.000 description 11
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 11
- 229960003726 vasopressin Drugs 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000035488 systolic blood pressure Effects 0.000 description 8
- -1 Glycerin-1-nitrate-sorbitol Chemical compound 0.000 description 7
- 230000003257 anti-anginal effect Effects 0.000 description 7
- 230000001077 hypotensive effect Effects 0.000 description 7
- 238000001802 infusion Methods 0.000 description 7
- 241000283973 Oryctolagus cuniculus Species 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 230000036772 blood pressure Effects 0.000 description 5
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 5
- 229960000201 isosorbide dinitrate Drugs 0.000 description 5
- 239000002207 metabolite Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 206010003225 Arteriospasm coronary Diseases 0.000 description 4
- 239000000006 Nitroglycerin Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229960003711 glyceryl trinitrate Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002823 nitrates Chemical class 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 3
- 229960004704 dihydroergotamine Drugs 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
- 230000003285 pharmacodynamic effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000001960 triggered effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FSJWCCRNAOECDK-RJMJUYIDSA-N OCC(O)CO[N+]([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O Chemical compound OCC(O)CO[N+]([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O FSJWCCRNAOECDK-RJMJUYIDSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 2
- 239000006190 sub-lingual tablet Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 229940124345 antianginal agent Drugs 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 208000012929 large congenital melanocytic nevus Diseases 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001839 systemic circulation Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Storage Of Web-Like Or Filamentary Materials (AREA)
- Beans For Foods Or Fodder (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833305690 DE3305690A1 (de) | 1983-02-18 | 1983-02-18 | Glycerinmononitrate zur behandlung der angina pectoris |
| EP84101527A EP0116944B1 (de) | 1983-02-18 | 1984-02-15 | Glycerinmononitrate zur Behandlung der Angina pectoris |
| DE8484101527T DE3460493D1 (en) | 1983-02-18 | 1984-02-15 | Glycerine mononitrate for the treatment of angina pectoris |
| AT84101527T ATE21483T1 (de) | 1983-02-18 | 1984-02-15 | Glycerinmononitrate zur behandlung der angina pectoris. |
| IL70990A IL70990A0 (en) | 1983-02-18 | 1984-02-17 | Pharmaceutical compositions containing glyceryl mononitrates |
| DK74184A DK74184A (da) | 1983-02-18 | 1984-02-17 | Anti-angina-middel |
| JP59028414A JPS59210016A (ja) | 1983-02-18 | 1984-02-17 | グリセリルモノニトレ−ト組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833305690 DE3305690A1 (de) | 1983-02-18 | 1983-02-18 | Glycerinmononitrate zur behandlung der angina pectoris |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3305690A1 true DE3305690A1 (de) | 1984-08-30 |
Family
ID=6191227
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833305690 Withdrawn DE3305690A1 (de) | 1983-02-18 | 1983-02-18 | Glycerinmononitrate zur behandlung der angina pectoris |
| DE8484101527T Expired DE3460493D1 (en) | 1983-02-18 | 1984-02-15 | Glycerine mononitrate for the treatment of angina pectoris |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484101527T Expired DE3460493D1 (en) | 1983-02-18 | 1984-02-15 | Glycerine mononitrate for the treatment of angina pectoris |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0116944B1 (enExample) |
| JP (1) | JPS59210016A (enExample) |
| AT (1) | ATE21483T1 (enExample) |
| DE (2) | DE3305690A1 (enExample) |
| DK (1) | DK74184A (enExample) |
| IL (1) | IL70990A0 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5001151A (en) * | 1987-08-11 | 1991-03-19 | Fujisawa Usa, Inc. | Aqueous nitroglycerin injection and manufacturing process |
| US4879308A (en) * | 1987-08-11 | 1989-11-07 | Lyphomed, Inc. | Aqueous nitroglycerin injection and manufacturing process |
| JPH0645538B2 (ja) * | 1987-09-30 | 1994-06-15 | 日本化薬株式会社 | ニトログリセリンスプレー剤 |
| NL8802276A (nl) * | 1988-09-15 | 1990-04-02 | Cedona Pharm Bv | Geneesmiddel met relaxerende werking, dat als aktieve stof een nitraatester bevat. |
| US5278192A (en) * | 1992-07-02 | 1994-01-11 | The Research Foundation Of State University Of New York | Method of vasodilator therapy for treating a patient with a condition |
-
1983
- 1983-02-18 DE DE19833305690 patent/DE3305690A1/de not_active Withdrawn
-
1984
- 1984-02-15 EP EP84101527A patent/EP0116944B1/de not_active Expired
- 1984-02-15 AT AT84101527T patent/ATE21483T1/de not_active IP Right Cessation
- 1984-02-15 DE DE8484101527T patent/DE3460493D1/de not_active Expired
- 1984-02-17 DK DK74184A patent/DK74184A/da not_active Application Discontinuation
- 1984-02-17 IL IL70990A patent/IL70990A0/xx unknown
- 1984-02-17 JP JP59028414A patent/JPS59210016A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3460493D1 (en) | 1986-09-25 |
| ATE21483T1 (de) | 1986-09-15 |
| JPS59210016A (ja) | 1984-11-28 |
| EP0116944B1 (de) | 1986-08-20 |
| JPH0414644B2 (enExample) | 1992-03-13 |
| DK74184A (da) | 1984-08-19 |
| EP0116944A1 (de) | 1984-08-29 |
| IL70990A0 (en) | 1984-05-31 |
| DK74184D0 (da) | 1984-02-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |