CH639659A5 - NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE. - Google Patents

NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE. Download PDF

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Publication number
CH639659A5
CH639659A5 CH1283578A CH1283578A CH639659A5 CH 639659 A5 CH639659 A5 CH 639659A5 CH 1283578 A CH1283578 A CH 1283578A CH 1283578 A CH1283578 A CH 1283578A CH 639659 A5 CH639659 A5 CH 639659A5
Authority
CH
Switzerland
Prior art keywords
compounds
formula
ch2ch
new
production
Prior art date
Application number
CH1283578A
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German (de)
Inventor
Peter Dr Neumann
Original Assignee
Sandoz Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH1283578A priority Critical patent/CH639659A5/en
Priority to DE19792949491 priority patent/DE2949491A1/en
Priority to SE7910188A priority patent/SE445219B/en
Priority to BE1/9643A priority patent/BE880591A/en
Priority to IT51095/79A priority patent/IT1164097B/en
Priority to NL7909024A priority patent/NL193066C/en
Priority to GB7943113A priority patent/GB2037766B/en
Priority to CY1321A priority patent/CY1321A/en
Priority to GB08215988A priority patent/GB2103203B/en
Priority to NZ192422A priority patent/NZ192422A/en
Priority to FR7930829A priority patent/FR2444681A1/en
Priority to AU53896/79A priority patent/AU536055B2/en
Priority to IE2445/79A priority patent/IE49496B1/en
Priority to JP16396579A priority patent/JPS5583783A/en
Priority to IE1165/83A priority patent/IE49497B1/en
Priority to ZA00796842A priority patent/ZA796842B/en
Priority to PH24383A priority patent/PH19536A/en
Priority to NZ199437A priority patent/NZ199437A/en
Priority to US06/359,751 priority patent/US4466972A/en
Publication of CH639659A5 publication Critical patent/CH639659A5/en
Priority to SG975/85A priority patent/SG97585G/en
Priority to MY130/85A priority patent/MY8500130A/en
Priority to KE3593A priority patent/KE3593A/en
Priority to HK160/86A priority patent/HK16086A/en
Priority to NL990014C priority patent/NL990014I1/en

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Classifications

    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Description

Die Erfindung betrifft organische Verbindungen der Formel I, The invention relates to organic compounds of the formula I

R„OOC R "OOC

COOR COOR

CH CH

worin Ri, R2 und X folgende Bedeutungen haben und y die Stellung des Dihydropyridinrestes angibt: where Ri, R2 and X have the following meanings and y indicates the position of the dihydropyridine radical:

R. R.

R; R;

y y

X X

CHj CHj

CH3 CH3

4 4th

O O

C2H5 C2H5

C2H5 C2H5

5 5

O O

CH2CH(CH3>2 CH2CH (CH3> 2

C2H5 C2H5

4 4th

S S

CH2CH(CH3)2 CH2CH (CH3) 2

C2H5 C2H5

4 4th

0 0

C(CH3)3 C (CH3) 3

C(CH3)3 C (CH3) 3

4 4th

0 0

CH2CH(CH3)2 CH2CH (CH3) 2

CH2CH(CH3)2 CH2CH (CH3) 2

4 4th

0 0

(CH2)20C2HS (CH2) 20C2HS

C2H5 C2H5

4 4th

0 0

(CH2)2OC2HS (CH2) 2OC2HS

C2H5 C2H5

4 4th

s s

(CH2)20C2HS (CH2) 20C2HS

C2H5 C2H5

5 5

s s

Es wurde gefunden, dass die oben genannten Verbindungen besonders wertvolle pharmakologische Wirkungen besitzen. It has been found that the compounds mentioned above have particularly valuable pharmacological effects.

Die Herstellung der Verbindungen der Formel I kann nach der Methode, beschrieben im Beispiel 1, ausgeführt werden. Die dabei verwendeten Ausgangsverbindungen sind entweder bekannt oder analog zu den bekannten Verbindungen herstellbar. The compounds of the formula I can be prepared by the method described in Example 1. The starting compounds used are either known or can be prepared analogously to the known compounds.

Die erfindungsgemäss erhaltenen Verbindungen der Formel I besitzen günstige pharmakodynamische Eigenschaften. Insbesondere bewirken die Verbindungen der Formel I eine Erweiterung der Herzkranzgefässe, wie dies Resultaten von Versuchen zu entnehmen ist, wobei der Blut-fluss zum Myokard einer anästhetisierten Katze mit Hilfe der Mikrosphärenmethode nach Verabreichung der Wirksubstanz in Dosen von 30 bis 50 ji.g/kg i.v. oder 150 p.g/kg i.d. gemessen wird. Die Verbindungen der Formel I besitzen ebenfalls eine günstige Wirkung gegen Angina pectoris, wie dies der Erhöhung der Koronardurchblutung bei einer anästhetisierten Katze nach Verabreichung der Wirksubstanz zu entnehmen ist. The compounds of formula I obtained according to the invention have favorable pharmacodynamic properties. In particular, the compounds of the formula I cause an enlargement of the coronary arteries, as can be seen from the results of experiments, the blood flow to the myocardium of an anesthetized cat using the microsphere method after administration of the active substance in doses of 30 to 50 ji.g / kg iv or 150 p.g / kg i.d. is measured. The compounds of the formula I also have a favorable action against angina pectoris, as can be seen from the increase in coronary blood flow in an anesthetized cat after administration of the active substance.

Die Verbindungen der Formel I sind deshalb zur Behandlung von Koronarinsuffizienz geeignet. Die Verbindungen steigern ferner die Durchblutung der Beinmuskulatur bei der anästhesierten Katze, wie dies mit Hilfe der Mikrosphärenmethode in Dosen von 30-50 ug/kg i.v. oder 150 ug/kg i.d. gezeigt werden kann. Die Verbindungen sind daher zur Gefässerweiterung in diesem Bereich geeignet. The compounds of formula I are therefore suitable for the treatment of coronary insufficiency. The compounds also increase blood flow to the leg muscles in the anesthetized cat, as is done with the microsphere method in doses of 30-50 µg / kg IV. or 150 ug / kg i.d. can be shown. The connections are therefore suitable for vessel expansion in this area.

Die zu verwendenden Dosen variieren naturgemäss je nach Art der Substanz, der Administration und des zu behandelnden Zustandes. Zufriedenstellende Resultate erhält man bei Verabreichung von Verbindungen der Formel I in einer täglichen Dosis von 0,01 bis 10 mg/kg Tierkörpergewicht. Bei grösseren Säugetieren ist eine täglich zu verabreichende Menge zwischen 5 und 100 mg angezeigt. Diese Dosis kann auch in kleineren Dosen 2 bis 4 mal täglich oder in Retardform verabreicht werden. Eine Einheitsdosis, beispielsweise eine zur oralen Verabreichung geeignete Tablette kann zwischen 1 und 50 mg des Wirkstoffes zusammen mit geeigneten pharmazeutisch indifferenten Hilfsstoffen enthalten. The doses to be used naturally vary depending on the type of substance, the administration and the condition to be treated. Satisfactory results are obtained when compounds of the formula I are administered in a daily dose of 0.01 to 10 mg / kg of animal body weight. For larger mammals, a daily dose of between 5 and 100 mg is indicated. This dose can also be administered in smaller doses 2 to 4 times a day or in extended release. A unit dose, for example a tablet suitable for oral administration, can contain between 1 and 50 mg of the active ingredient together with suitable pharmaceutically indifferent auxiliaries.

Die Verbindungen der Formel I wirken überdies auf den Blutdruck. Insbesondere besitzen sie antihypertensive Eigenschaften, wie sich bei Tierversuchen an der hypertonen Grollman-Ratte (Methoden nach A. Grollman [Proc. Soc. Exptl. Biol. and Med. 57,104,1944]) bei Dosen von 0,1 bis 10 mg/kg zeigt. Die Verbindungen der Formel I sind daher zur Behandlung der Hypertonie geeignet. Die zu verwendenden Dosen variieren naturgemäss je nach Art der Substanz, der Administration und des zu behandelnden Zustandes. Zufriedenstellende Resultate erhält man bei Verabreichung von Verbindungen der Formel I in einer täglichen Dosis von 0,5 bis 50 mg/kg Tierkörpergewicht. Bei grösseren Säugetieren ist eine täglich zu verabreichende Menge zwischen 5 und 1000 mg angezeigt. Diese Dosis kann auch in kleineren Dosen 2-4 mal täglich oder in Retardform verabreicht werden. Eine Einheitsdosis, beispielsweise eine zur oralen Verabreichung geeignete Tablette kann zwischen 1,25 und 500 mg des Wirkstoffes zusammen mit geeigneten pharmazeutisch indifferenten Hilfsstoffen enthalten. The compounds of formula I also act on blood pressure. In particular, they have antihypertensive properties, as found in animal experiments on the hypertonic Grollman rat (methods according to A. Grollman [Proc. Soc. Exptl. Biol. And Med. 57,104,1944]) at doses of 0.1 to 10 mg / kg shows. The compounds of formula I are therefore suitable for the treatment of hypertension. The doses to be used naturally vary depending on the type of substance, the administration and the condition to be treated. Satisfactory results are obtained when compounds of the formula I are administered in a daily dose of 0.5 to 50 mg / kg of animal body weight. For larger mammals, a daily dose of between 5 and 1000 mg is indicated. This dose can also be administered in smaller doses 2-4 times a day or in sustained release. A unit dose, for example a tablet suitable for oral administration, can contain between 1.25 and 500 mg of the active ingredient together with suitable pharmaceutically indifferent auxiliaries.

Die Verabreichung von Verbindungen der Formel I kann entweder oral in Form von Tabletten, Granulaten, Kapseln oder Dragees, oder parenteral in Form von Injektionslösungen erfolgen. The compounds of the formula I can be administered either orally in the form of tablets, granules, capsules or dragées, or parenterally in the form of injection solutions.

In den nachfolgenden Beispielen sind die Temperaturen in Grad-Celsius angegeben und sind unkorrigiert. In the following examples, the temperatures are given in degrees Celsius and are uncorrected.

Beispiel 1 example 1

4-(2,1,3-Benzoxadiazolyl-4)-3-methoxy-carbonyl-1,4-dihydro-2,6-dimethylpyridin-5-carbonsäure-isobutylester 3 g 2,l,3-Benzoxadiazol-4-aldehyd, 3,2 g Acetessigsäure- Isobutyl 4- (2,1,3-benzoxadiazolyl-4) -3-methoxy-carbonyl-1,4-dihydro-2,6-dimethylpyridine-5-carboxylic acid 3 g 2, 1,3-benzoxadiazol-4-aldehyde 3.2 g acetoacetic acid

2 2nd

5 5

10 10th

15 15

20 20th

25 25th

30 30th

35 35

40 40

45 45

50 50

55 55

60 60

65 65

3 3rd

639 659 639 659

isobutylester, 2,3 g /J-Aminocrotonsäuremethylester und 10 isobutyl ester, 2.3 g / J-aminocrotonic acid methyl ester and 10

Rl Rl

R2 R2

y y

X X

Smp. M.p.

ml Äthanol werden zusammen unter Rühren 3 Stunden zum ml of ethanol together with stirring for 3 hours

Rückfluss erhitzt. Das Reaktionsgemisch wird anschliessend Reflux heated. The reaction mixture is then

CH.3 CH.3

CH3 CH3

4 4th

0 0

215-221 215-221

eingedampft und der Rückstand über Silicagel mit Chloro evaporated and the residue over silica gel with chloro

C:Hs C: Hs

C2H5 C2H5

5 5

0 0

173-174 173-174

form/Essigester (8:1) chromatographiert, wobei man die s CH2CH(CHj): form / ethyl acetate (8: 1) chromatographed, taking the s CH2CH (CHj):

C2H5 C2H5

4 4th

s s

85-95 85-95

Titelverbindung, die aus Diisopropyläther kristallisiert bei Title compound that crystallizes from diisopropyl ether

CH:CH(CH3): CH: CH (CH3):

C2H5 C2H5

4 4th

0 0

145-146,5 145-146.5

148-158° (aus Methylcyclohexan) schmilzt, erhält. 148-158 ° (from methylcyclohexane) melts, obtained.

C(CH.<)3 C (CH. <) 3

C(CH3)3 C (CH3) 3

4 4th

0 0

207-210 207-210

Analog Beispiel 1 und unter Verwendung entsprechender Analogously to Example 1 and using the corresponding

CH:CH(CH3): CH: CH (CH3):

CH2CH(CH3)2 CH2CH (CH3) 2

4 4th

0 0

135,5-137 135.5-137

Ausgangsverbindungen gelangt man zu folgenden Verbin Output connections lead to the following connection

(CH:):OC:H5 (CH :): OC: H5

C2H5 C2H5

4 4th

0 0

126-128 126-128

dungen der Formel I, worin Ri. R: und X folgende Bedeu io (CH:):OC:Hj of formula I, in which Ri. R: and X have the following meaning io (CH :): OC: Hj

C2H5 C2H5

4 4th

s s

Öl tungen haben und y die Stellung des Dihydropyridinrestes Oil lines and y have the position of the dihydropyridine residue

(CHÔ2OC2H5 (CHÔ2OC2H5

C2H5 C2H5

5 5

s s

72-78 72-78

angibt: indicates:

Claims (2)

639 659 639 659 PATENTANSPRÜCHE 1. Verbindungen der Formel 1, PATENT CLAIMS 1. Compounds of Formula 1, COOR COOR CH CH worin Ri, R: und X folgende Bedeutungen haben und y die Stellung des Dihydropyridinrestes angibt: where Ri, R: and X have the following meanings and y indicates the position of the dihydropyridine radical: R, R, R: R: y y X X CH; CH; CHs CHs 4 4th O O C2H5 C2H5 C2H5 C2H5 5 5 O O CH2CH(CH3)2 CH2CH (CH3) 2 C2H5 C2H5 4 4th S S CH2CH(CH3)2 CH2CH (CH3) 2 C2H5 C2H5 4 4th 0 0 C(CH3); C (CH3); C(CH3)3 C (CH3) 3 4 4th 0 0 CH2CH(CH3)2 CH2CH (CH3) 2 CH2CH(CH3)2 CH2CH (CH3) 2 4 4th 0 0 (CH:)20C2H5 (CH:) 20C2H5 C2H5 C2H5 4 4th 0 0 (CH2)2OC2H5 (CH2) 2OC2H5 C2H5 C2H5 4 4th s s (CH2)20C2HS (CH2) 20C2HS C2H5 C2H5 5 5 s s 2. Arzneimittel, eine Verbindung der Formel I enthaltend. 2. Medicament containing a compound of formula I.
CH1283578A 1977-06-20 1978-12-18 NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE. CH639659A5 (en)

Priority Applications (24)

Application Number Priority Date Filing Date Title
CH1283578A CH639659A5 (en) 1978-12-18 1978-12-18 NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE.
DE19792949491 DE2949491A1 (en) 1978-12-18 1979-12-08 1,4-DIHYDROPYRIDINE, THEIR PRODUCTION AND USE
SE7910188A SE445219B (en) 1978-12-18 1979-12-11 1,4-DIHYDROPYRIDINE DERIVATIVES, PROCEDURES FOR PREPARING THEREOF, AND PHARMACEUTICAL COMPOSITION
BE1/9643A BE880591A (en) 1978-12-18 1979-12-13 NOVEL 1,4-DIHYDROPYRIDINES, THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS
IT51095/79A IT1164097B (en) 1978-12-18 1979-12-14 "1,4-DI HYDROPYRIDINE THEIR PREPARATION AND THEIR APPLICATION AS MEDICATIONS"
NL7909024A NL193066C (en) 1978-12-18 1979-12-14 Methyl, isopropyl-4- (2,1,3-benzoxadiazol-4-yl) -2,6-dimethyl-1,4-dihydro pyridine-3,5-dicarboxylate and pharmaceutical composition containing this compound.
GB7943113A GB2037766B (en) 1978-12-18 1979-12-14 1,4-dihydropyridines their preparation and pharmaceutical compositions containing them
CY1321A CY1321A (en) 1978-12-18 1979-12-14 1,4-dihydropyridines their preparation and pharmaceutical compositions containing them
GB08215988A GB2103203B (en) 1978-12-18 1979-12-14 1,4-dihydropyridines, their preparation and pharmaceutical compositions containing them
AU53896/79A AU536055B2 (en) 1978-12-18 1979-12-17 Derivatives of 1,4 dihydropyridine substituted by benzoxadiazole or benzthiadiazole
FR7930829A FR2444681A1 (en) 1978-12-18 1979-12-17 NOVEL 1,4-DIHYDROPYRIDINES, THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS
NZ192422A NZ192422A (en) 1978-12-18 1979-12-17 Benzoxadiazoles and benzothiadiazoles with 1,4-dihydropyridine moiety pharmaceutical compositions
IE2445/79A IE49496B1 (en) 1978-12-18 1979-12-17 A 1,4-dihydropyridine derivative,its preparation and pharmaceutical compositions containing it
JP16396579A JPS5583783A (en) 1978-12-18 1979-12-17 1*44dihydropyridine derivative
IE1165/83A IE49497B1 (en) 1978-12-18 1979-12-17 1,4-dihydropyridines,their preparation and pharmaceutical compositions containing them
ZA00796842A ZA796842B (en) 1978-12-18 1979-12-18 1,4-dihydropyridines, their preparation and pharmaceutical compositions containing them
PH24383A PH19536A (en) 1977-06-20 1980-08-01 Benzoxadiazoles and benzothiadiazoles and pharmaceutical composition containing them
NZ199437A NZ199437A (en) 1978-12-18 1982-01-07 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxycarbonylpyridine-5-carboxylic acid isopropyl ester and pharmaceutical compositions
US06/359,751 US4466972A (en) 1977-06-20 1982-03-19 Benzoxadiazoles and benzothiadiazoles, their preparation and pharmaceutical compositions containing them
SG975/85A SG97585G (en) 1978-12-18 1985-12-20 A 1,4-dihydropyridine derivative,its preparation and pharmaceutical compositions containing it
MY130/85A MY8500130A (en) 1978-12-18 1985-12-30 A 1,4-dihydropyridine derivative its preparation and pharmaceutical compositions containing it
KE3593A KE3593A (en) 1978-12-18 1986-01-08 A 1,4-dihydropyridine derivative its preparation and pharmaceutical compositions containing it
HK160/86A HK16086A (en) 1978-12-18 1986-03-06 A 1,4-dihydropyridine derivate its preparation and pharmaceutical compositions containing it
NL990014C NL990014I1 (en) 1978-12-18 1999-05-11 Methyl, isopropyl-4- (2,1,3-benzoxadiazol-4-yl) -2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and pharmaceutical composition containing this compound.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1283578A CH639659A5 (en) 1978-12-18 1978-12-18 NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE.

Publications (1)

Publication Number Publication Date
CH639659A5 true CH639659A5 (en) 1983-11-30

Family

ID=4386824

Family Applications (1)

Application Number Title Priority Date Filing Date
CH1283578A CH639659A5 (en) 1977-06-20 1978-12-18 NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE.

Country Status (18)

Country Link
JP (1) JPS5583783A (en)
AU (1) AU536055B2 (en)
BE (1) BE880591A (en)
CH (1) CH639659A5 (en)
CY (1) CY1321A (en)
DE (1) DE2949491A1 (en)
FR (1) FR2444681A1 (en)
GB (2) GB2037766B (en)
HK (1) HK16086A (en)
IE (1) IE49496B1 (en)
IT (1) IT1164097B (en)
KE (1) KE3593A (en)
MY (1) MY8500130A (en)
NL (2) NL193066C (en)
NZ (1) NZ192422A (en)
SE (1) SE445219B (en)
SG (1) SG97585G (en)
ZA (1) ZA796842B (en)

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DE3022030A1 (en) * 1980-06-12 1981-12-17 Bayer Ag, 5090 Leverkusen 4-THIAZOLE or 4-IMIDAZOLE-SUBSTITUTED, 1,4-DIHYDROPYRIDINE, METHOD FOR THE PRODUCTION THEREOF AND THE MEDICINAL PRODUCTS CONTAINING THEM
CH655658B (en) * 1980-09-18 1986-05-15
DE3269219D1 (en) * 1981-11-17 1986-03-27 Fisons Plc Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals
ZA83959B (en) * 1982-03-10 1984-09-26 Sandoz Ltd 1,4-dihydropyridine derivatives,their preparation and pharmaceutical compositions containing them
US4414213A (en) * 1982-03-22 1983-11-08 Mead Johnson & Company Dihydropyridyl cyclic imidate esters and their pharmaceutical use
IL68975A (en) * 1982-06-15 1987-01-30 Sandoz Ag 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid ester derivatives in optically active form,their preparation and pharmaceutical compositions containing them
FR2528431B1 (en) * 1982-06-15 1986-01-10 Sandoz Sa NOVEL 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS
JPS5978186A (en) * 1982-10-27 1984-05-04 Yoshitomi Pharmaceut Ind Ltd 1,4-dihydropyridine-3,5-dicarboxylic acid ester derivative
US4794111A (en) * 1984-05-23 1988-12-27 Bayer Aktiengesellschaft Dihydropyridine preparations containing β-blockers
HU198844B (en) * 1984-06-14 1989-12-28 Sandoz Ag Process for producing new galenic pharmaceutical composition ensuring retarded release of active ingredient
US5260321A (en) * 1984-11-12 1993-11-09 Sandoz Ltd. Use of 1,4-dihydropyridine derivatives and combinations thereof with calcitonins
HU197201B (en) * 1985-10-01 1989-03-28 Sandoz Ag Process for producing oral pharmaceutical compositions of controlled solubility of the active components
DE3542794A1 (en) * 1985-12-04 1987-06-11 Bayer Ag ANTI-HYPERTENSIVE COMBINATION PREPARATION
GB8626217D0 (en) * 1986-11-03 1986-12-03 Sandoz Ltd Pharmaceutical compositions
US4816263A (en) * 1987-10-02 1989-03-28 Alza Corporation Dosage form for treating cardiovascular diseases comprising isradipine
KR940003492B1 (en) * 1988-10-27 1994-04-23 주식회사 유한양행 Process for preparation of 1,4 dihydropyridine derivatives
DE4222770A1 (en) * 1992-07-10 1994-01-13 Bayer Ag Light-activated 1- (2-nitrobenzyl) -substituted 1,4-dihydropyridines
EP2316468A1 (en) 2002-02-22 2011-05-04 Shire LLC Delivery system and methods for protecting and administering dextroamphetamine
AU2003269482A1 (en) * 2003-09-10 2005-03-29 Shasun Chemicals And Drugs Limited Process for the manufacture of 2,1,3-benzoxadiazole-4-carboxaldehyde
CN103613584B (en) * 2013-11-27 2016-04-27 沈阳药科大学 The method of a kind of Isrodipine synthetic product aftertreatment

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Publication number Priority date Publication date Assignee Title
DE1670824C3 (en) * 1967-03-20 1978-08-03 Bayer Ag, 5090 Leverkusen 1,4-Dihydropyridine-33-dicarboxylic acid alkyl ester
FR2320750A1 (en) * 1975-08-12 1977-03-11 Hexachimie 1,4-DIHYDRO PYRIDINES AND THEIR THERAPEUTIC APPLICATION
DE2616991A1 (en) * 1976-04-17 1977-10-27 Bayer Ag Thio-substd. dihydro-pyridine derivs. - coronary vasodilators and antihypertensives prepd. e.g. by reacting dicarbonyl cpds. with amines and thio-substd. ketones
JPS5373327A (en) * 1976-12-13 1978-06-29 Matsushita Electric Ind Co Ltd Power source system
FI64938C (en) * 1977-06-20 1984-02-10 Sandoz Ag PROCEDURE FOR THE FRAMEWORK OF THERAPEUTIC THERAPEUTIC BENSOX A- AND OX BENZOTIADIAZOLYL-1,4-DIHYDROPYRID DERIVATIVES

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NL193066C (en) 1998-09-08
GB2037766B (en) 1983-02-16
NL7909024A (en) 1980-06-20
JPS5583783A (en) 1980-06-24
NZ192422A (en) 1982-09-14
KE3593A (en) 1986-02-07
SE445219B (en) 1986-06-09
GB2103203A (en) 1983-02-16
SE7910188L (en) 1980-06-19
AU536055B2 (en) 1984-04-19
IE49496B1 (en) 1985-10-16
IE792445L (en) 1980-06-18
HK16086A (en) 1986-03-14
FR2444681B1 (en) 1982-10-29
NL990014I1 (en) 1999-07-01
IT7951095A0 (en) 1979-12-14
MY8500130A (en) 1985-12-31
ZA796842B (en) 1981-07-29
NL193066B (en) 1998-05-06
CY1321A (en) 1986-06-27
JPH0369910B2 (en) 1991-11-05
FR2444681A1 (en) 1980-07-18
AU5389679A (en) 1980-06-26
IT1164097B (en) 1987-04-08
SG97585G (en) 1986-07-18
GB2103203B (en) 1983-06-08
DE2949491C2 (en) 1988-10-27
BE880591A (en) 1980-06-13
GB2037766A (en) 1980-07-16
DE2949491A1 (en) 1980-06-26

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