US3784684A - Coronary dilator in a pharmaceutical dosage unit form - Google Patents

Coronary dilator in a pharmaceutical dosage unit form Download PDF

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Publication number
US3784684A
US3784684A US00282476A US3784684DA US3784684A US 3784684 A US3784684 A US 3784684A US 00282476 A US00282476 A US 00282476A US 3784684D A US3784684D A US 3784684DA US 3784684 A US3784684 A US 3784684A
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United States
Prior art keywords
parts
weight
shell
gelatine
dihydropyridine
Prior art date
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Expired - Lifetime
Application number
US00282476A
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English (en)
Inventor
F Bossert
W Vater
K Bauer
K Adams
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Bayer AG
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Bayer AG
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Priority claimed from DE19722209526 external-priority patent/DE2209526C3/de
Application filed by Bayer AG filed Critical Bayer AG
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Publication of US3784684A publication Critical patent/US3784684A/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S206/00—Special receptacle or package
    • Y10S206/828—Medicinal content

Definitions

  • the present invention relates to a new dosage unit form I for a known coronary dilator, 4-(2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine, and a method for its production. See US. Pats. 3,485,847; 3,644,627; and Canadian Pats. 868,909; 868,910; 868,911.
  • Disturbances of the coronary blood flow resembling an attack and manifesting themselves clinically in the form of a so-called angina pectoris attack are a vitally important indication and demand immediate treatment with a drug.
  • An attack of angina pectoris is usually accompanied by intolerable pain and feelings of extreme anxiety. Physiologically, the impaired blood flow through the heart during an attack can result in permanent damage to the cardiac muscle which in an extreme case can lead to death. Drugs which are employed in the therapy of angina pectoris must therefore become fully efliective in the shortest possible time (within a few minutes).
  • 1,4-dihydropyridine derivatives act as coronary dilators and can be used in the treatment Patented Jan, 8, 1974 of the above disease. Substances which belong to this group of compounds do not dissolve readily and are extremely light-sensitive.
  • So labile is the redox system of 1,4-dihydropyridines, that the addition of reducing agents, oxidizing agents, or redox systems (e.g. Fe II/Fe III, ascorbic acid/dehydroascorbic acid) cannot check rapid decomposition.
  • reducing agents e.g. Fe II/Fe III, ascorbic acid/dehydroascorbic acid
  • redox systems e.g. Fe II/Fe III, ascorbic acid/dehydroascorbic acid
  • perlingually administered drugs are rapidly absorbed and that they therefore have a rapid onset of action (e.g. nitroglycerol) (Sollman, T., A Manual of Pharmacology, W. B. Saunders Co., Philadelphia, Pa., 1957, p. 631).
  • the present invention provides an instant oral-release capsule having a shell of gelatine preferably incorporating an opacifier and a dye, said shell containing a mixture of:
  • the shell incorporates a dye that absorbs light of wavelength 250-460 nm. and an opacifier, and the mixture contains 1 to 10, preferably 5 to 8, parts by weight of the at least one alcohol.
  • a particularly preferred proportion of the at least one polyalkylene glycol in the mixture is 15 to 35 parts by weight.
  • the invention also provides a process for the production of the capsules of the invention, comprising mixing the ingredients (1) to (3) and any other ingredients, and enclosing the resultant mixture in the gelatine capsule.
  • instant oral-release capsule means a capsule, having a shell, generally of gelatine, containing a fluid pharmaceutical composition which can be released from the shell by biting and breaking the latter; the subject bites this capsule thereby releasing its contents into his mouth from where the medicament is immediately absorbed into his system.
  • Each capsule will generally contain a specific measured amount of the pharmaceutical composition which is enough for a single dose.
  • capsules according to the present invention containing 4-(2 nitrophenyl)-2,6-dimethyl-3,5-dicarbo methoxy-l,4-dihydropyridine has the following advantages: the capsule can be taken immediately by the patient himself in the event of a heart attack and takes elfect within a few minutes. There can be no doubt about the dosage, as it is fixed by the amount of active ingredient contained in the instant oral-release capsule. Administration is extremely simple: it is carried out perlingually, which dispenses with the necessity, for example, of first counting out a certain number of drops containing the active ingredient. Such procedure is impossible in the present case anyway because the active ingredient is too light-sensitive.
  • the active ingredient used in the capsules of the invention is a known compound, 4-(2-nitrophenyl)-2,6-dimethyl-3,S-dicarbomethoxy 1,4 dihydropyridine which has been administered in a variety of conventional pharmaceutical formulations including common gelatine capsules and with conventional carriers including polyalkylene glycols.
  • This compound has the formula Polyalkylene glycols having a mean molecular weight of 200 to 4000 suitable for use according to the invention are also known.
  • Polyethylene and/or polypropylene glycol having a mean molecular weight of 300 to 600 are preferably used.
  • polyglycols Hoechst
  • Lutrol 9 BASF
  • Polydiols Haills
  • Carbowaxes Union Carbide
  • Lower alcohols having 2 to 8 carbon atoms and 1 to 3 hydroxy groups suitable for use in accordance with the invention are also known.
  • Glycerol, propylene glycol, butylene glycol or benzyl alcohol are preferably used.
  • the mixture contained in the capsule may also contain one or more further ingredients apart from those specifically mentioned above.
  • auxiliary agents may be employed: flavoring agents (aromas), essential oils, preferably peppermint oil, fennel oil, anise oil, caraway oil, lemon oil or eucalyptus oil), and sweetening agents (e.g. saccharin, sodium saccharin (soluble saccharin) and glycyrrhizinic acid ammonium salt).
  • the dye incorporated into the gelatine shell of the capsule preferably absorbs light in the wavelength range 280-420 nm.
  • a preferred dye is the foodstulf dye Gelborange-S (Sunset Yellow) (Color Index No. 15 985).
  • the dye should, of course, have no toxic effect when used according to the invention.
  • a preferred opaeifier for incorporation into the gelatine shell is titanium dioxide.
  • the gelatine shell used in accordance with the invention preferably consists, in its ready-to-use state, of 54% to 80% of gelatine, 10% to 36% of glycerol or sorbitol and 7% to 15% of water and 0.5% to of an opacifier such as titanium dioxide, an iron oxide (such as yellow iron oxide, red iron oxide or brown iron oxide) or calcium carbonate, and the dye Gelborange-S (Color Index No. 15 985).
  • the gelatine composition for the capsule shell can conveniently be prepared by mixing 40% to 66% of pure gelatine with 8% to 36% of glycerol (or sorbitol) and 22% to 34% of water and by allowing the mixture to swell for some time.
  • this composi- 4 tion is melted at 60 C. until free of bubbles and the opaeifier and the dye Gelborange-S (Color Index No. 15 985) and, if desired, preservatives (e.g. p-aminobenzoic acid, sorbic acid, and benzyl alcohol) are homogeneously worked into the composition.
  • preservatives e.g. p-aminobenzoic acid, sorbic acid, and benzyl alcohol
  • the mixture constituting the filling of the capsule according to the invention is conveniently prepared by dissolving 4-(2' nitrophenyl)-2,6-dimethyl-3,S-dicarbomethoxy-l,4-dihydropyridine in the alcohol and polyalkylene glycol with slight heating and stirring.
  • the filling into the gelatine capsules can be carried out according to known methods; for example, with Scherer, Leiner, Norton or Accogel machines. After filling, the capsules are generally dried and are then ready to use.
  • the accompanying drawing is a graph showing the very rapid onset of action with perlingual absorption, in particular in comparison with oral administration of the active ingredient of the invention in tragacanth.
  • the graph illustrates the action of the active ingredient according to the invention upon administration in various ways to dogs which have been anaesthetized and catheterized in the coronary sinus.
  • the rise in oxygen pressure in the blood of the coronary veins after perlingual administration of 1 mg./kg. of the active ingredient according to the invention in the form of a mixture of glycerol, polyethylene glycol and water was recorded in comparison with the application into the stomach of 1 mg./kg. of the active ingredient (micronized substance in tragacanth)
  • the mean values are given for 5 tests each.
  • the curve clearly shows the immediate onset of action following perlingual administration. After five minutes the maximal value is almost reached, whereas after administration into the stomach the oxygen pressure only attains the same value after 60 minutes. Administration of the active ingredient in solid formulation, such as tablets, drages or the like reveals even less favorable values.
  • An instant oral-release gelatine shell perlingual capsule having a dye that absorbs light of wave lengths of from 250 to 460 nm. and an opacifier in the shell of gelatine, said shell being capable of being broken by biting, and enclosed within said shell a fluid mixture of:
  • An instant oral-release capsule according to claim 1 which contains to 35 parts by weight of said at least one polyalkylene glycol.
  • An instant oral-release capsule according to claim 1 wherein said at least one alcohol is glycerol, propylene glycol, butylene glycol, benzyl alcohol or a mixture of 2 or more thereof.
  • An instant oral-release capsule according to claim 1 wherein the opacifier is titanium dioxide, an iron oxide or calcium carbonate.
  • An instant oral-release capsule according to claim 11 wherein the iron oxide is yellow iron oxide, red iron oxide or brown iron oxide.

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  • 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)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medical Preparation Storing Or Oral Administration Devices (AREA)
  • Hydrogenated Pyridines (AREA)
US00282476A 1971-08-24 1972-08-21 Coronary dilator in a pharmaceutical dosage unit form Expired - Lifetime US3784684A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2142316 1971-08-24
DE19722209526 DE2209526C3 (de) 1972-02-29 1972-02-29 Coronartherapeutlkum in Form von Gelatine-BeiBkapseln

Publications (1)

Publication Number Publication Date
US3784684A true US3784684A (en) 1974-01-08

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US00282476A Expired - Lifetime US3784684A (en) 1971-08-24 1972-08-21 Coronary dilator in a pharmaceutical dosage unit form

Country Status (25)

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US (1) US3784684A (no)
JP (2) JPS5434048B2 (no)
KR (1) KR780000433B1 (no)
BE (1) BE787951A (no)
BG (1) BG27728A3 (no)
CA (1) CA981582A (no)
CY (1) CY918A (no)
DD (1) DD99729A5 (no)
DK (1) DK130628B (no)
EG (1) EG10633A (no)
ES (1) ES406047A1 (no)
FI (1) FI53922C (no)
FR (1) FR2150848B1 (no)
GB (1) GB1362627A (no)
HK (1) HK44877A (no)
IE (1) IE36891B1 (no)
IL (1) IL40165A (no)
KE (1) KE2756A (no)
LU (1) LU65929A1 (no)
MY (1) MY7800003A (no)
NL (1) NL176836C (no)
NO (1) NO138167C (no)
RO (1) RO88521B (no)
SG (1) SG34877G (no)
SU (1) SU432703A3 (no)

Cited By (72)

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US4056610A (en) * 1975-04-09 1977-11-01 Minnesota Mining And Manufacturing Company Microcapsule insecticide composition
US4088750A (en) * 1974-02-22 1978-05-09 Burroughs Wellcome Co. Method and preparation for increasing bioavailability of digoxin
DE2822882A1 (de) * 1977-06-07 1978-12-21 Yamanouchi Pharma Co Ltd Nifedipine-enthaltende feste praeparatzusammensetzung, verfahren zu ihrer herstellung und ihre verwendung
US4198391A (en) * 1973-07-20 1980-04-15 R. P. Scherer Ltd. Pharmaceutical compositions
US4366145A (en) * 1981-06-24 1982-12-28 Sandoz, Inc. Soft gelatin capsule with a liquid ergot alkaloid center fill solution and method of preparation
WO1984003417A1 (en) * 1983-03-02 1984-09-13 Scherer Corp R P Soft gelatin capsules and fill achieving optimum hardness and flexibility during storage
US4537898A (en) * 1983-03-03 1985-08-27 Bayer Aktiengesellschaft Liquid formulations of dihydropyridines
EP0164587A2 (de) * 1984-05-23 1985-12-18 Bayer Ag Nifedipinpräparate und Verfahren zu ihrer Herstellung
EP0165450A2 (de) * 1984-05-23 1985-12-27 Bayer Ag Nifedipinkombinationspräparate und Verfahren zu ihrer Herstellung
US4620974A (en) * 1983-07-07 1986-11-04 American Home Products Corporation Pharmaceutical composition containing a liquid lubricant
US4689233A (en) * 1986-01-06 1987-08-25 Siegfried Aktiengesellschaft Coronary therapeutic agent in the form of soft gelatin capsules
US4693892A (en) * 1985-09-10 1987-09-15 Bayer Aktiengesellschaft Gelatin containing β-carotene
US4777048A (en) * 1983-07-07 1988-10-11 American Home Products Corporation Pharmaceutical composition containing a liquid lubricant
US4780316A (en) * 1983-03-02 1988-10-25 R.P. Scherer Corporation Gelatin capsule
AU584122B2 (en) * 1984-08-23 1989-05-18 Kuhlemann & Co. Metered dose aerosol of nifedipin
US4832952A (en) * 1983-07-07 1989-05-23 American Home Products Corporation Pharmaceutical composition containing a liquid lubricant
US4857312A (en) * 1985-12-18 1989-08-15 Bayer Aktiengesellschaft Dihydropyridine spray, process for its preparation and its pharmaceutical use
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US5200192A (en) * 1987-11-11 1993-04-06 Walter Wimmer Instant oral-release capsule containing nifedipine
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CN101300010B (zh) * 2005-10-31 2012-06-06 兴和株式会社 光稳定性优异的医药制剂
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SU432703A3 (no) * 1971-08-24 1974-06-15 Фридрих Боссерт, Вульф Фатер, Курт Бауер
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CA2056032A1 (en) * 1990-11-29 1992-05-30 Minoru Aoki Hard capsule preparation
JP4730985B2 (ja) * 1997-09-10 2011-07-20 武田薬品工業株式会社 安定化された医薬製剤

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FR2150848A1 (no) 1973-04-13
BE787951A (fr) 1973-02-26
JPS5434048B2 (no) 1979-10-24
CY918A (en) 1977-12-23
IE36891B1 (en) 1977-03-16
LU65929A1 (no) 1973-01-15
IL40165A0 (en) 1972-10-29
NO138167C (no) 1978-07-26
GB1362627A (en) 1974-08-07
RO88521B (ro) 1987-05-01
CA981582A (en) 1976-01-13
JPS53121921A (en) 1978-10-24
KE2756A (en) 1977-10-14
FR2150848B1 (no) 1976-04-16
EG10633A (en) 1976-08-31
DK130628B (da) 1975-03-17
KR780000433B1 (en) 1978-10-14
IE36891L (en) 1973-02-24
NL7211565A (no) 1973-02-27
NO138167B (no) 1978-04-10
ES406047A1 (es) 1981-08-16
BG27728A3 (en) 1979-12-12
NL176836C (nl) 1985-06-17
DK130628C (no) 1975-08-25
MY7800003A (en) 1978-12-31
NL176836B (nl) 1985-01-16
FI53922C (fi) 1979-09-07
HK44877A (en) 1977-09-09
IL40165A (en) 1975-03-13
DD99729A5 (no) 1973-08-20
RO88521A (ro) 1987-04-30
JPS4828621A (no) 1973-04-16
SU432703A3 (no) 1974-06-15
FI53922B (fi) 1978-05-31
SG34877G (en) 1987-04-03

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