DE1795792B2 - Verwendung von 5-Fluornikotinsäure - Google Patents
Verwendung von 5-FluornikotinsäureInfo
- Publication number
- DE1795792B2 DE1795792B2 DE1795792A DE1795792A DE1795792B2 DE 1795792 B2 DE1795792 B2 DE 1795792B2 DE 1795792 A DE1795792 A DE 1795792A DE 1795792 A DE1795792 A DE 1795792A DE 1795792 B2 DE1795792 B2 DE 1795792B2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- serum
- lipoid
- concentration
- fluoronicotinic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Purses, Travelling Bags, Baskets, Or Suitcases (AREA)
Description
oder deren therapeutisch verträgliche Salze.
Therapeutisch verträgliche Salze sind solche Säureadditionssalze, die physiologisch unschädlich sind, wenn
sie in einer Dosis und einer Verabreichungsfrequenz verabreicht werden, die den therapeutischen Effekt
ergeben. Typische therapeutisch verträgliche Säureadditionssalze sind beispielsweise aber nicht ausschließlich
Salze von Mineralsäure, wie Salzsäure, Bromwasserstoffsäure, Phosphorsäure oder ^Schwefelsäure, von
organischen Säuren, wie Essigsäure, Milchsäure, Lävulinsäure. Zitronensäure, Fumarsäure, Maleinsäure, Bernsteinsäure,
Weinsäure oder Benzoesäure, und Sulfonsäuren, wie Methansulfonsäure und Sulfaminsäure.
In der "klinischen Praxis werden die 5-Fluornikotinsäure
oder deren Salze normalerweise oral oder durch Injektionen in der Form pharmazeitischer Präparate
verabreicht. Diese enthalten beispielsweise das Hydrochlorid oder Hydrosulfat der 5-Fluornikotinsäure
ίο
5-Fluornikotinsäure ist aus der US-PS 25 16 830 bekannt. Aus dieser US-PS sowie aus »Chemical
Abstracts«, 52,3028 d (1958) und 58,4836 b (1963) ist die
Verwendung von 5-Fluornikotinsäure als antibakterielles Mittel bekannt.
Im Hinblick auf sich mehrende Anzeichen, daß eine übermäßige Serumlipoidkonzentration in Wechselwirkung
mit pathogenen Mechanismen und Symptomen verschiedener Krankheiten, wie Gefäßkrankheiten,
Diabetes mellitus und Hyperthyroidismus, steht, ist eine
Herabsetzung der Serumlipoidkonzentration während der Behandlung solcher Krankheiten wichtig.
Die Herabsetzung der Serumlipoidkonzentration kann man durch Hemmung der Lipoidmobilisierung,
wie beispielsweise durch die Herabsetzung der Gesamtabgabe von Lipoiden an den Kreislauf in Form freier
Fettsäuren aus gespeicherten Triglyceriden in Adiposegewebe, erreichen.
Weiterhin ist aus »The Lancet«, I, Seiten 191 und 192
(1965) bekannt, daß Nikotinsäure den durch Noradrenalin induzierten Serumspiegel freier Fettsäuren senkt.
Die der Erfindung zugrundeliegende Aufgabe bestand nun darin, ein Mittel zur Herabsetzung der
Serumlipoidkonzentration bzw. Hemmung der Lipoidmobilisierung mit erhöhter Aktivität und möglichst
geringer Toxizität zu erhalten.
Erfindungsgemäß verwendet man bei der Herabsetzung der Serumlipoidkonzentration bzw. Hemmung der
Lipoidmobilisierung 5-Fluornikotinsäure der Formel
F COOH
mit einem pharmazeutisch verträglichen Trägermaterial
Das Trägermaterial kann ein festes, halbfestes oder flüssiges Verdünnungsmittel oder eine einnehmbare
Kapsel sein. Gewöhnlich wird die aktive Substanz zwischen 0,1 und 95 Gew.-% des Präparares, spezieller
zwischen 0,5 und 20 Gew.-°/o von Präparaten, die für die Injektion bestimmt sind, und zwischen 2 und 50 Gew.-%
von Präparaten, die für die orale Verabreichung geeignet sind, ausmachen. Flüssige Präparate für die
orale Verabreichung können in der Forn von Sirupen oder Suspensionen vorliegen, wie beispielsweise als
Lösungen mit einem Gehalt von 0,2 bis 20 Gew.-% der aktiven Substanz. Lösungen für die parenter&le
Verabreichung durch Injektion können wäßrige Lösungen eines wasserlöslichen, pharmazeutisch verträglichen
Salzes der aktiven Substanz sein, vorzugsweise in einer Konzentration von 0,5 bis 10 Gew.-%.
5-Fluornikotinsäure wurde hinsichtlich der Verminderung
der Konzentration freier Fettsäuren im Serum von Hunden gemäß der von Carlson und Liljedahr in
»Acta Med. Scand.« 1963, (173), Seiten 787 bis 791 und
von Bergström, Carlson und Orö in »Acta Physiol. Scand.«, 1964 (60), Seiten 170 bis 180,
beschriebenen Methode untersucht und mit Nikotinsäure verglichen.
Bei dieser Methode wurde die jeweilige Testverbindung bei einer vorgetäuschten Streß-Situation untersucht,
in der Noradrenalin bekanntermaßen die Lipoidmobilisierung stimuliert. Anästhesierte Hunde
erhielten kontinuierliche Infusion von Noradrenalin in einer konstanten Geschwindigkeit. Nach 60minütiger
Infusion wurde eine Lösung der Testverbindung intravenös injiziert. Arterielle Blutproben wurden
abgenommen, das Blut wurde unmittelbar zentrifugiert und das Plasma zur Bestimmung der freien Fettsäuren
gemäß Dole, »J. Clin. Invest 1«, 1956(35), Seite 150,
modifiziert nach Trout et al, »J. Lipid. Res.«, 1960 (1),
Seite 199, extrahiert Die Verbindungen wurden danach
beurteilt, in welchem Maß sie die durch Noradrenalininfusionen hervorgerufene Erhöhung der Konzentration
freier Fettsäuren im Serum kompensierten und wie lange ihre Wirkungsdauer dabei war. Der Wert a
bedeutet den Prozentsatz der relativen Senkung der Konzentration der freien Fettsäuren im Serum gegenüber
dem durch das Noradrenalin hervorgerufenen erhöhten Wert, und der Wert b bedeutet die
Wirkungsdauer in Minuten, während der diese relative Senkung der Konzentration der freien Fettsäuren im
Serum mehr als 50% beträgt. Die Testverbindungen wurden in einer Dosis von 25 mg/kg verabreicht Für die
Bewertung der Verbindungen wurde folgende Bewertungsskala aufgestellt wobei für die relative Senkung
der Konzentration der freien Fettsäuren im Serum das Überschreiten von 80% und für die Wirkungsdauer das
Überschreiten einer Zeit von 100 Minuten gewählt wurde.
Relative Senkung
Wirkungsdauer
in Minuten
in Minuten
Effekt
mindestens 80
b5 mindestens 80
höchstens 79
höchstens 79
b5 mindestens 80
höchstens 79
höchstens 79
mindestens 100
weniger als 100
mindestens 100
weniger als 100
weniger als 100
mindestens 100
weniger als 100
Effekt Dauer einer mehr als 50 %igen Senkung des Spiegeis freier Fettsäuren im Serum
Nikotinsäure 5-FIuornikotinsäure
+++ 1,0 Stdn. ++++ 1,9 Stdn.
Die 5-Fluornikotinsäure besitzt eine äußerst niedrige Toxizität, der LD» (i. p.) bei Mäusen liegt über 2 g/kg, der
für die Vergleichsverbindung Nikotinsäure bei etwa 0,5 g/kg.
Claims (1)
- Patentanspruch:Verwendung von 5-Fluornikotinsäure der Formel F COOHoder deren therapeutisch verträglichen Salzen bei der Herabsetzung der Serumlipoidkonzentration bzw. Hemmung der Lipoidmobilisierung.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE15717/66A SE327987B (de) | 1966-11-16 | 1966-11-16 | |
GB03687/67A GB1213162A (en) | 1966-11-16 | 1967-03-23 | Serum lipid lowering pyridine derivatives and their preparation |
GB19174/67A GB1157186A (en) | 1966-11-16 | 1967-04-26 | Serum Lipid Lowering Pyridine Derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
DE1795792A1 DE1795792A1 (de) | 1975-06-19 |
DE1795792B2 true DE1795792B2 (de) | 1979-07-19 |
DE1795792C3 DE1795792C3 (de) | 1980-03-20 |
Family
ID=27257023
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1795792A Expired DE1795792C3 (de) | 1966-11-16 | 1967-11-13 | Verwendung von 5-Fluornikotinsäure |
DE1967A0057350 Granted DE1670003B2 (de) | 1966-11-16 | 1967-11-13 | 3-hydroxymethyl-5-fluorpyridin |
DE1912352A Expired DE1912352C3 (de) | 1966-11-16 | 1969-03-12 | Pyridin-N-oxyd-Derivale und Verfahren zu ihrer Herstellung |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1967A0057350 Granted DE1670003B2 (de) | 1966-11-16 | 1967-11-13 | 3-hydroxymethyl-5-fluorpyridin |
DE1912352A Expired DE1912352C3 (de) | 1966-11-16 | 1969-03-12 | Pyridin-N-oxyd-Derivale und Verfahren zu ihrer Herstellung |
Country Status (15)
Country | Link |
---|---|
US (2) | US3637714A (de) |
JP (1) | JPS5023030B1 (de) |
AT (2) | AT289113B (de) |
BE (1) | BE706471A (de) |
CH (1) | CH508625A (de) |
DE (3) | DE1795792C3 (de) |
DK (1) | DK125709B (de) |
ES (1) | ES347190A1 (de) |
FI (1) | FI49962C (de) |
FR (3) | FR8017M (de) |
GB (3) | GB1213162A (de) |
IE (1) | IE32127B1 (de) |
NL (2) | NL150440B (de) |
NO (1) | NO124927B (de) |
SE (1) | SE364510B (de) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3737542A (en) * | 1966-11-16 | 1973-06-05 | Lars Anders Fritz Carlsson | Lowering excessive serum lipid concentrations and preparations containing fluoro-pyridine derivatives |
GB1312775A (en) * | 1969-07-07 | 1973-04-04 | Mar Pha Etu Expl Marques | Aryloxyalkyl nicotinates |
FR2074707B1 (de) * | 1970-01-20 | 1973-01-12 | Centre Etd Ind Pharma | |
US4115393A (en) * | 1974-03-28 | 1978-09-19 | Siegfried Aktiengesellschaft | Pyridyl alkyl esters of substituted phenoxy alkanoic acids having the ability to reduce the level of fatty substances in the blood |
FR2270878B1 (de) * | 1974-05-15 | 1978-02-03 | Fabre Sa Pierre | |
DE2443539C3 (de) * | 1974-09-11 | 1978-11-23 | Karl Dr.Med. 4044 Kaarst Credner | Ester der 5-n-Butyl-pyridin-carbonsäure- (2), Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate |
BE826867A (fr) * | 1974-11-20 | 1975-07-16 | Medicament hypolipidemiant et hydrocholesterolemiant | |
US4058534A (en) * | 1975-03-14 | 1977-11-15 | Solco Basel Ag | Therapeutically effective nicotinates and N-oxide nicotinates of aliphatic amines |
ES438246A1 (es) * | 1975-06-04 | 1977-01-16 | Alter Sa | Un procedimiento de preparacion del glicol 2-(p-clorofenoci)-2-metilpropinato nicotinato. |
ES438245A1 (es) * | 1975-06-04 | 1977-01-16 | Alter Sa | Procedimiento de purificacion del ester mixto 1-(2-(p-cloro-fenoxi)-2metilpropionato), 2-nicotinato de etilenglicol. |
JPS5387531A (en) * | 1977-01-11 | 1978-08-02 | Takenaka Komuten Co | Foldable hanging scaffold for building |
JPS53101827A (en) * | 1977-02-17 | 1978-09-05 | Takenaka Komuten Co | Method of temporarily building scaffold |
JPS5422927A (en) * | 1977-07-22 | 1979-02-21 | Takenaka Komuten Co | Method of tentatively building scaffold* and scaffold for effecting said method |
DE2962915D1 (en) * | 1979-11-02 | 1982-07-08 | Stauffer Chemical Co | Pyridylalkyl esters, insect repellent compositions and method of repelling insects |
IT1168389B (it) * | 1981-05-06 | 1987-05-20 | Alfa Farmaceutici Spa | Derivati di alcandioli con attivita' ipolipidemizzante,metodi per la loro preparazione e composizioni farmaceutiche che li contengono |
AT383346B (de) * | 1983-05-02 | 1987-06-25 | Merz & Co Gmbh & Co | Verfahren zur herstellung von neuen n-oxiden von pyridylcarbonsaeureestern |
DE3315877A1 (de) * | 1983-05-02 | 1984-11-08 | Merz + Co GmbH & Co, 6000 Frankfurt | N-oxide von pyridyl-carbonsaeureestern, ein verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten |
FR2612189B1 (fr) * | 1987-03-13 | 1989-06-23 | Roussel Uclaf | Nouveaux derives de la pyridine, leur procede de preparation et les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions les renfermant |
LU87821A1 (fr) * | 1990-10-12 | 1992-05-25 | Cird Galderma | Composes bi-aromatiques,et leur utilisation en medecine humaine et veterinaire et en cosmetique |
US5436344A (en) * | 1990-11-29 | 1995-07-25 | Pfizer Inc. | 3-bromo-5-chloro-pyridines used as intermediates in the synthesis of azatetralones |
WO1993011768A1 (en) * | 1991-12-13 | 1993-06-24 | Smithkline Beecham Corporation | Pyridyl compounds for psoriasis treatment |
ATE429915T1 (de) * | 2002-10-10 | 2009-05-15 | Arena Pharm Inc | 5-substituierte 2h-pyrazon-3-carbonsäure-derivate als antilipolytische mittel zur behandlung von stoffwechselstörungen, wie z.b. dyslipidemie |
WO2005011677A1 (en) * | 2003-06-13 | 2005-02-10 | Arena Pharmaceuticals, Inc. | 5-substituted 2h-pyrazole-3-carboxylic acid derivatives as agonists for the nicotinic acid receptor rup25 for the treatment of dyslipidemia and related diseases |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE322214B (de) * | 1965-06-28 | 1970-04-06 | Bofors Ab | |
FR1498459A (de) * | 1965-07-30 | 1968-01-08 |
-
1967
- 1967-03-23 GB GB03687/67A patent/GB1213162A/en not_active Expired
- 1967-04-26 GB GB19174/67A patent/GB1157186A/en not_active Expired
- 1967-11-13 DE DE1795792A patent/DE1795792C3/de not_active Expired
- 1967-11-13 DE DE1967A0057350 patent/DE1670003B2/de active Granted
- 1967-11-14 CH CH1586267A patent/CH508625A/de not_active IP Right Cessation
- 1967-11-14 BE BE706471D patent/BE706471A/xx unknown
- 1967-11-14 NO NO170525A patent/NO124927B/no unknown
- 1967-11-15 ES ES347190A patent/ES347190A1/es not_active Expired
- 1967-11-15 AT AT1028267A patent/AT289113B/de not_active IP Right Cessation
- 1967-11-15 GB GB52041/67A patent/GB1171509A/en not_active Expired
- 1967-11-15 US US689751A patent/US3637714A/en not_active Expired - Lifetime
- 1967-11-16 NL NL676715616A patent/NL150440B/xx unknown
- 1967-11-16 FR FR128477A patent/FR8017M/fr not_active Expired
- 1967-11-16 DK DK573567AA patent/DK125709B/da unknown
- 1967-11-16 FI FI673086A patent/FI49962C/fi active
- 1967-11-16 FR FR128479A patent/FR1544594A/fr not_active Expired
- 1967-11-17 SE SE15867/67A patent/SE364510B/xx unknown
-
1968
- 1968-04-08 IE IE400/68A patent/IE32127B1/xx unknown
-
1969
- 1969-03-12 DE DE1912352A patent/DE1912352C3/de not_active Expired
- 1969-03-17 US US807948A patent/US3622587A/en not_active Expired - Lifetime
- 1969-03-19 AT AT268069A patent/AT294089B/de active
- 1969-03-24 FR FR6908585A patent/FR2004661A1/fr not_active Withdrawn
- 1969-03-25 NL NL6904594A patent/NL6904594A/xx unknown
-
1971
- 1971-04-09 JP JP46021827A patent/JPS5023030B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
DE1795792A1 (de) | 1975-06-19 |
NO124927B (de) | 1972-06-26 |
NL6904594A (de) | 1969-09-29 |
FI49962C (fi) | 1975-11-10 |
GB1213162A (en) | 1970-11-18 |
NL150440B (nl) | 1976-08-16 |
DE1670003A1 (de) | 1971-11-04 |
SE364510B (de) | 1974-02-25 |
FR2004661A1 (de) | 1969-11-28 |
US3622587A (en) | 1971-11-23 |
DE1912352B2 (de) | 1975-04-17 |
GB1157186A (en) | 1969-07-02 |
DE1912352C3 (de) | 1975-11-27 |
IE32127L (en) | 1968-10-26 |
DE1912352A1 (de) | 1969-10-09 |
GB1171509A (en) | 1969-11-19 |
AT294089B (de) | 1971-11-10 |
IE32127B1 (en) | 1973-04-18 |
AT289113B (de) | 1971-04-13 |
FR1544594A (fr) | 1968-10-31 |
FR8017M (de) | 1970-08-03 |
DE1670003B2 (de) | 1976-06-16 |
DE1795792C3 (de) | 1980-03-20 |
US3637714A (en) | 1972-01-25 |
NL6715616A (de) | 1968-05-17 |
ES347190A1 (es) | 1969-05-01 |
BE706471A (de) | 1968-05-14 |
CH508625A (de) | 1971-06-15 |
DK125709B (da) | 1973-03-26 |
FI49962B (de) | 1975-07-31 |
JPS5023030B1 (de) | 1975-08-05 |
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