CH639659A5 - New 1,4-dihydropyridine derivatives, their preparation and use. - Google Patents

New 1,4-dihydropyridine derivatives, their preparation 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
c2h5
ch3
ch
compounds
formula
Prior art date
Application number
CH1283578A
Other languages
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 claimed from IE1165/83A external-priority patent/IE49497B1/en
Priority claimed from PH24383A external-priority patent/PH19536A/en
Priority claimed from NZ199437A external-priority patent/NZ199437A/en
Priority claimed from US06/359,751 external-priority patent/US4466972A/en
Publication of CH639659A5 publication Critical patent/CH639659A5/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/04Heterocyclic 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

Description

Die Erfindung betrifft organische Verbindungen der Formel I, The invention relates to organic compounds of 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: wherein Ri, R2 and X have the following meanings and y indicates the position of the Dihydropyridinrestes:

R. R.

R; R;

y y

X X

CHj CHj

CH3 CH3

4 4

O O

C2H5 C2H5

C2H5 C2H5

5 5

O O

CH2CH(CH3>2 CH 2 CH (CH3> 2

C2H5 C2H5

4 4

S S

CH2CH(CH3)2 CH2CH (CH3) 2

C2H5 C2H5

4 4

0 0

C(CH3)3 C (CH3) 3

C(CH3)3 C (CH3) 3

4 4

0 0

CH2CH(CH3)2 CH2CH (CH3) 2

CH2CH(CH3)2 CH2CH (CH3) 2

4 4

0 0

(CH2)20C2HS (CH2) 20C2HS

C2H5 C2H5

4 4

0 0

(CH2)2OC2HS (CH2) 2OC2HS

C2H5 C2H5

4 4

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 above compounds have particularly useful pharmacological effects.

Die Herstellung der Verbindungen der Formel I kann nach der Methode, beschrieben im Beispiel 1, ausgeführt werden. The preparation of the compounds of Formula I may according to the method described in Example 1 are carried out. Die dabei verwendeten Ausgangsverbindungen sind entweder bekannt oder analog zu den bekannten Verbindungen herstellbar. The starting compounds used are either known or analogous to the known compounds to produce.

Die erfindungsgemäss erhaltenen Verbindungen der Formel I besitzen günstige pharmakodynamische Eigenschaften. The present invention compounds of formula I obtained have favorable pharmacodynamic properties. 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 iv oder 150 pg/kg id gemessen wird. In particular, the compounds cause of formula I is an enlargement of the coronary vessels, as can be seen from results of experiments, wherein the blood flow to the myocardium of anesthetized cat using the microspheres method of administration of the active substance in doses of 30 to 50 ji.g / kg iv or 150 pg / kg id is measured. 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 also have a beneficial effect against angina pectoris, as can be seen at a anesthetized cat after administration of the active substance of the increase in coronary blood flow.

Die Verbindungen der Formel I sind deshalb zur Behandlung von Koronarinsuffizienz geeignet. The compounds of formula I are therefore suitable for the treatment of coronary insufficiency. 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 iv oder 150 ug/kg id gezeigt werden kann. The compounds also increase the blood flow to the leg muscles in the anesthetized cat, as / kg using the microspheres method in doses of 30-50 ug iv or 150 ug / kg id can be shown. Die Verbindungen sind daher zur Gefässerweiterung in diesem Bereich geeignet. The compounds are therefore suitable for vasodilatation in this area.

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

Die Verbindungen der Formel I wirken überdies auf den Blutdruck. The compounds of formula I act also on the blood pressure. 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. In particular, they possess antihypertensive properties, as is in animal experiments on the hypertonic Grollman rat (according to methods A. Grollman [Proc. Soc. Exptl. Biol. And Med. 57,104,1944]) at doses of 0.1 to 10 mg / kg shows. Die Verbindungen der Formel I sind daher zur Behandlung der Hypertonie geeignet. The compounds of formula I are therefore suitable for the treatment of hypertension. Die zu verwendenden Dosen variieren naturgemäss je nach Art der Substanz, der Administration und des zu behandelnden Zustandes. The doses to be used naturally vary depending on the nature of the substance, the administration and the condition to be treated. Zufriedenstellende Resultate erhält man bei Verabreichung von Verbindungen der Formel I in einer täglichen Dosis von 0,5 bis 50 mg/kg Tierkörpergewicht. gives satisfactory results when administering compounds of Formula I in a daily dose of 0.5 to 50 mg / kg of animal body weight. Bei grösseren Säugetieren ist eine täglich zu verabreichende Menge zwischen 5 und 1000 mg angezeigt. For larger mammals one to be administered daily amount between 5 and 1000 mg is indicated. Diese Dosis kann auch in kleineren Dosen 2-4 mal täglich oder in Retardform verabreicht werden. This dose may be administered once daily or in retard 2-4 in smaller doses. 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. A unit dose, for example one suitable for oral administration may be tablet from 1.25 to 500 mg of the active ingredient contained together with suitable pharmaceutically inert excipients.

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 administration of compounds of formula I may be either granules, capsules or dragees be administered orally in the form of tablets, 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 temperatures are in degrees Celsius are shown, 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- 4- (2,1,3-benzoxadiazolyl-4) -3-methoxy-carbonyl-1,4-dihydro-2,6-dimethylpyridine-5-carboxylic acid isobutyl ester 3 g of 2, l, 3-benzoxadiazole-4-aldehyde , 3.2 g acetoacetic

2 2

5 5

10 10

15 15

20 20

25 25

30 30

35 35

40 40

45 45

50 50

55 55

60 60

65 65

3 3

639 659 639659

isobutylester, 2,3 g /J-Aminocrotonsäuremethylester und 10 isobutyl, 2,3 g / J-aminocrotonate and 10

Rl rl

R2 R2

y y

X X

Smp. Mp.

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

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

CH.3 CH.3

CH3 CH3

4 4

0 0

215-221 215-221

eingedampft und der Rückstand über Silicagel mit Chloro evaporated and the residue chromatographed on 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 / Essigester (8: 1) to give the s CH 2 CH (CHj):

C2H5 C2H5

4 4

s s

85-95 85-95

Titelverbindung, die aus Diisopropyläther kristallisiert bei Title compound which crystallized from diisopropyl at

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

C2H5 C2H5

4 4

0 0

145-146,5 145 to 146.5

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

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

C(CH3)3 C (CH3) 3

4 4

0 0

207-210 207-210

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

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

CH2CH(CH3)2 CH2CH (CH3) 2

4 4

0 0

135,5-137 135.5 to 137

Ausgangsverbindungen gelangt man zu folgenden Verbin Starting compounds leads to the following Verbin

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

C2H5 C2H5

4 4

0 0

126-128 126-128

dungen der Formel I, worin Ri. R: und X folgende Bedeu io (CH:):OC:Hj compounds of formula I wherein Ri R:. X and the following significance io (CH :): OC: Hj

C2H5 C2H5

4 4

s s

Öl tungen haben und y die Stellung des Dihydropyridinrestes Oil have obligations and y is the position of the Dihydropyridinrestes

(CHÔ2OC2H5 (CHÔ2OC2H5

C2H5 C2H5

5 5

s s

72-78 72-78

angibt: indicating:

Claims (2)

  1. 639 659 639659
    PATENTANSPRÜCHE 1. Verbindungen der Formel 1, 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: wherein Ri, R: and X have the following meanings and y indicates the position of the Dihydropyridinrestes:
    R, R
    R: R:
    y y
    X X
    CH; CH;
    CHs CHs
    4 4
    O O
    C2H5 C2H5
    C2H5 C2H5
    5 5
    O O
    CH2CH(CH3)2 CH2CH (CH3) 2
    C2H5 C2H5
    4 4
    S S
    CH2CH(CH3)2 CH2CH (CH3) 2
    C2H5 C2H5
    4 4
    0 0
    C(CH3); C (CH3);
    C(CH3)3 C (CH3) 3
    4 4
    0 0
    CH2CH(CH3)2 CH2CH (CH3) 2
    CH2CH(CH3)2 CH2CH (CH3) 2
    4 4
    0 0
    (CH:)20C2H5 (CH:) 20C2H5
    C2H5 C2H5
    4 4
    0 0
    (CH2)2OC2H5 (CH2) 2OC2H5
    C2H5 C2H5
    4 4
    s s
    (CH2)20C2HS (CH2) 20C2HS
    C2H5 C2H5
    5 5
    s s
  2. 2. Arzneimittel, eine Verbindung der Formel I enthaltend. 2. A pharmaceutical composition a compound of the formula I containing.
CH1283578A 1978-12-18 1978-12-18 New 1,4-dihydropyridine derivatives, their preparation and use. CH639659A5 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1283578A CH639659A5 (en) 1978-12-18 1978-12-18 New 1,4-dihydropyridine derivatives, their preparation and use.

Applications Claiming Priority (24)

Application Number Priority Date Filing Date Title
CH1283578A CH639659A5 (en) 1978-12-18 1978-12-18 New 1,4-dihydropyridine derivatives, their preparation and use.
DE19792949491 DE2949491C2 (en) 1978-12-18 1979-12-08
SE7910188A SE445219B (en) 1978-12-18 1979-12-11 1,4-dihydropyridine derivatives, process for the tell accession derav and pharmaceutical composition
BE1/9643A BE880591A (en) 1978-12-18 1979-12-13 New 1,4-dihydropyridine, their preparation and their use as medicines
GB7943113A GB2037766B (en) 1978-12-18 1979-12-14 1,4-dihydropyridines their preparation and pharmaceutical compositions containing them
IT5109579A IT1164097B (en) 1978-12-18 1979-12-14 "1,4-di idropiridine their preparation and their application as medicaments"
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 said compound.
CY132179A 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
FR7930829A FR2444681B1 (en) 1978-12-18 1979-12-17
IE244579A IE49496B1 (en) 1978-12-18 1979-12-17 A 1,4-dihydropyridine derivative,its preparation and pharmaceutical compositions containing it
NZ19242279A NZ192422A (en) 1978-12-18 1979-12-17 Benzoxadiazoles and benzothiadiazoles with 1,4-dihydropyridine moiety pharmaceutical compositions
JP54163965A JPH0369910B2 (en) 1978-12-18 1979-12-17
AU53896/79A AU536055B2 (en) 1978-12-18 1979-12-17 Derivatives of 1,4 dihydropyridine substituted by benzoxadiazole or benzthiadiazole
IE1165/83A IE49497B1 (en) 1978-12-18 1979-12-17 1,4-dihydropyridines,their preparation and pharmaceutical compositions containing them
ZA00796842A ZA7906842B (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
SG97585A SG97585G (en) 1978-12-18 1985-12-20 A 1,4-dihydropyridine derivative,its preparation and pharmaceutical compositions containing it
MY8500130A MY8500130A (en) 1978-12-18 1985-12-30 A 1,4-dihydropyridine derivative its preparation and pharmaceutical compositions containing it
KE359386A KE3593A (en) 1978-12-18 1986-01-08 A 1,4-dihydropyridine derivative its preparation and pharmaceutical compositions containing it
HK16086A 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-dihydro pyridine-3,5-dicarboxylate, and pharmaceutical composition containing said compound.

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) 1978-12-18 1978-12-18 New 1,4-dihydropyridine derivatives, their preparation and use.

Country Status (18)

Country Link
JP (1) JPH0369910B2 (en)
AU (1) AU536055B2 (en)
BE (1) BE880591A (en)
CH (1) CH639659A5 (en)
CY (1) CY1321A (en)
DE (1) DE2949491C2 (en)
FR (1) FR2444681B1 (en)
GB (2) GB2103203B (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) ZA7906842B (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3022030A1 (en) * 1980-06-12 1981-12-17 Bayer Ag 4-thiazole and 4-imidazol-substituted 1,4-dihydropyridines, processes for their preparation and pharmaceutical compositions 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
ZA8300959B (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
FR2528431B1 (en) * 1982-06-15 1986-01-10 Sandoz Sa New derivatives of 1,4-dihydropyridine, their preparation and their use as medicines
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
JPS6340432B2 (en) * 1982-10-27 1988-08-11 Yoshitomi Pharmaceutical
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
NL194822C (en) * 1985-10-01 2003-04-03 Novartis Ag A composition for oral administration with controlled release and the method for its preparation.
DE3542794A1 (en) * 1985-12-04 1987-06-11 Bayer Ag antihypertensive kombinationspraeparat
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 연만희 Process for preparation of 1,4 dihydropyridine derivatives
DE4222770A1 (en) * 1992-07-10 1994-01-13 Bayer Ag Photoactivatable 1- (2-nitrobenzyl) substituted 1,4-dihydropyridines
KR20040088519A (en) 2002-02-22 2004-10-16 뉴 리버 파마슈티칼스, 인크. Active Agent Delivery Systems and Methods for Protecting and Administering Active Agents
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 latter method of processing synthetic products isradipine

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1670824C3 (en) * 1967-03-20 1978-08-03 Bayer Ag, 5090 Leverkusen
FR2320750B1 (en) * 1975-08-12 1979-09-28 Hexachimie
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 Foerfarande Foer framstaellning of nya terapeutiskt anvaendbara bensoxa- Science bensotiadiazolyl-1,4-dihydropyridinderivat

Also Published As

Publication number Publication date
GB2037766B (en) 1983-02-16
NL990014I1 (en) 1999-07-01
GB2103203B (en) 1983-06-08
FR2444681B1 (en) 1982-10-29
SE7910188L (en) 1980-06-19
IT7951095D0 (en) 1979-12-14
JPS5583783A (en) 1980-06-24
NL7909024A (en) 1980-06-20
NZ192422A (en) 1982-09-14
IE49496B1 (en) 1985-10-16
GB2037766A (en) 1980-07-16
ZA7906842B (en) 1981-07-29
IE792445L (en) 1980-06-18
DE2949491C2 (en) 1988-10-27
NL193066C (en) 1998-09-08
NL193066B (en) 1998-05-06
SE445219B (en) 1986-06-09
JPH0369910B2 (en) 1991-11-05
FR2444681A1 (en) 1980-07-18
HK16086A (en) 1986-03-14
BE880591A (en) 1980-06-13
DE2949491A1 (en) 1980-06-26
GB2103203A (en) 1983-02-16
MY8500130A (en) 1985-12-31
KE3593A (en) 1986-02-07
AU5389679A (en) 1980-06-26
SG97585G (en) 1986-07-18
AU536055B2 (en) 1984-04-19
IT1164097B (en) 1987-04-08
CY1321A (en) 1986-06-27
BE880591A1 (en)

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