CH639659A5 - NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE. - Google Patents
NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE. Download PDFInfo
- 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
Links
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
Landscapes
- 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)
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) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Family Cites Families (5)
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 |
-
1978
- 1978-12-18 CH CH1283578A patent/CH639659A5/en not_active IP Right Cessation
-
1979
- 1979-12-08 DE DE19792949491 patent/DE2949491A1/en active Granted
- 1979-12-11 SE SE7910188A patent/SE445219B/en not_active IP Right Cessation
- 1979-12-13 BE BE1/9643A patent/BE880591A/en not_active IP Right Cessation
- 1979-12-14 GB GB7943113A patent/GB2037766B/en not_active Expired
- 1979-12-14 NL NL7909024A patent/NL193066C/en not_active IP Right Cessation
- 1979-12-14 GB GB08215988A patent/GB2103203B/en not_active Expired
- 1979-12-14 CY CY1321A patent/CY1321A/en unknown
- 1979-12-14 IT IT51095/79A patent/IT1164097B/en active Protection Beyond IP Right Term
- 1979-12-17 NZ NZ192422A patent/NZ192422A/en unknown
- 1979-12-17 FR FR7930829A patent/FR2444681A1/en active Granted
- 1979-12-17 IE IE2445/79A patent/IE49496B1/en not_active IP Right Cessation
- 1979-12-17 AU AU53896/79A patent/AU536055B2/en not_active Expired
- 1979-12-17 JP JP16396579A patent/JPS5583783A/en active Granted
- 1979-12-18 ZA ZA00796842A patent/ZA796842B/en unknown
-
1985
- 1985-12-20 SG SG975/85A patent/SG97585G/en unknown
- 1985-12-30 MY MY130/85A patent/MY8500130A/en unknown
-
1986
- 1986-01-08 KE KE3593A patent/KE3593A/en unknown
- 1986-03-06 HK HK160/86A patent/HK16086A/en not_active IP Right Cessation
-
1999
- 1999-05-11 NL NL990014C patent/NL990014I1/en unknown
Also Published As
Publication number | Publication date |
---|---|
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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH639659A5 (en) | NEW 1,4-DIHYDROPYRIDINE DERIVATIVES, THEIR PRODUCTION AND USE. | |
DE2904552C2 (en) | 2,6-Dimethyl-4- (3'-nitrophenyl) -1,4-dihydropyridine-3,5-dicarboxylic acid 3- (1-benzylpyrrolidin-3-yl) ester-5-lower alkyl ester | |
DE2815578C2 (en) | New pharmaceutical use of nimodipine | |
DE69014351T2 (en) | Pyridinecarboxamide derivatives and pharmaceutical compositions containing them. | |
DE3008056C2 (en) | ||
DE2117571A1 (en) | Asymmetrical 1,4-dihydropyridine carboxylic acid esters, process for their preparation and their use as pharmaceuticals I. Arfm: Farbenfabriken Bayer AG, 5090 Leverkusen | |
DE2210672A1 (en) | UNSYMMETRIC N-SUBSTITUTED DIHYDROPYRIDINS, THE METHOD OF MANUFACTURING AND THEIR USE AS A MEDICINAL PRODUCT | |
DE2117572A1 (en) | Asymmetrical 1,4-dihydropyridines, process for their preparation and their use as pharmaceuticals II | |
DE3426419A1 (en) | NEW OXINDOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS, AND INTERMEDIATE PRODUCTS | |
DE3200304A1 (en) | 3-AMINOPROPOXYARYL DERIVATIVES, THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THEM | |
DE3112055A1 (en) | BISPIDINE DERIVATIVES, THEIR PRODUCTION AND THE MEDICINAL PRODUCTS CONTAINING THEM | |
DD237165A5 (en) | PROCESS FOR THE PREPARATION OF CARBONYL COMPOUNDS AND THEIR SALTS | |
DE69012650T2 (en) | Piperidine derivative, process for its preparation and pharmaceutical composition containing the same. | |
EP0497121A1 (en) | Tetrazole derivatives, process for their production and their application | |
EP0010130B1 (en) | Sila-substituted 1,4-dihydropyridine derivatives, processes for their preparation, pharmaceutical compositions and process for their preparation | |
DE2523103A1 (en) | NEW PROPARGYL-2-PHENYLAMINO-IMIDAZOLINE- (2), THEIR ACID-ADDITIONAL SALTS, THESE MEDICINAL PRODUCTS AND METHOD FOR MANUFACTURING THE SAME | |
CH647519A5 (en) | HIGH PRESSURE REDUCING AMINES. | |
DE3216843C2 (en) | 3-Thiomethyl-pyridine derivatives, processes for their preparation and pharmaceuticals containing these compounds | |
DE2650013C3 (en) | 1,4-Dihydro-2,6-dimethyl-4- (3-nitrophenyl) -3,5-pyridinedicarboxylic acid isopropyl (2-propoxy-ethyl) ester, process for its preparation and medicinal products containing it | |
DE2404050A1 (en) | NEW HETEROCYCLIC BINDINGS AND METHODS FOR THEIR PRODUCTION | |
DE69629931T2 (en) | 1- (HETERO) ARYL-4- (CONDENSED THIAZOL-2-YLALKYL) PIPERAZINE DERIVATIVES, THEIR PRODUCTION AND THEIR USE IN TREATING 5-HT1A RECEPTOR MEDIATED DISEASES | |
CA1181402A (en) | Substituted 2-amino-3,4-dihydropyridine derivatives, their production and their medicinal use | |
DE3023717A1 (en) | NEW SULFURIZED ISOCHINOLINE DERIVATIVES, THE PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS, AND METHOD FOR PRODUCING THE NEW COMPOUNDS | |
DE1917432A1 (en) | Thiazoline compounds, their production and use as pharmaceuticals | |
DE2831671A1 (en) | NEW SUBSTITUTED 2-PHENYLAMINO-IMIDAZOLINE (2), THE ACID ADDITION SALTS THEREOF, THE MEDICINAL PRODUCTS CONTAINING THE SAME AND METHOD FOR THE PRODUCTION THEREOF |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PFA | Name/firm changed |
Owner name: SANDOZ AG TRANSFER- NOVARTIS AG |
|
PL | Patent ceased |