DE2140712A1 - MEDICINAL PRODUCTS CONTAINING 2-PYRIDONES - Google Patents
MEDICINAL PRODUCTS CONTAINING 2-PYRIDONESInfo
- Publication number
- DE2140712A1 DE2140712A1 DE2140712A DE2140712A DE2140712A1 DE 2140712 A1 DE2140712 A1 DE 2140712A1 DE 2140712 A DE2140712 A DE 2140712A DE 2140712 A DE2140712 A DE 2140712A DE 2140712 A1 DE2140712 A1 DE 2140712A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- optionally substituted
- cooh
- radical
- compounds
- 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.)
- Pending
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
- C07D213/60—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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
2-Pyridone enthaltende ArzneimittelMedicines containing 2-pyridone
Die Erfindung betrifft neue Arzneimittel mit psychopharmakologischer, antiphlogistischer, chemotherapeutischer, besonders antibakterieller, und/oder Kreislauf-Wirkung. Manche der Mittel haben auch eine Wirkung auf die Blutgerinnung.The invention relates to new drugs with psychopharmacological, anti-inflammatory, chemotherapeutic, especially antibacterial and / or circulatory effects. Some the remedies also have an effect on blood clotting.
Aus der Dissertation von Roland Gren, Freie Universität Berlin, Mathematisch-Naturwissenschaftliche Fakultät, Berlin 1968, sind einige l-Phenyl-4-methoxy(bzw. 4-benzoyloxy)~2-pyridone bekannt, welche in ^-Stellung einen Methyl-, Styryl-, Phenyläthyl- oder Phenylbutadienylrest aufweisen und in 5-Stellung ein Wasserstoffatom oder einen Carboxyl- oder Carbäthoxylrest besitzen. Eine arzneiliche Wirkung dieser Verbindungen ist dort nicht beschrieben.From the dissertation by Roland Gren, Free University of Berlin, Faculty of Mathematics and Natural Sciences, Berlin 1968, some are l-phenyl-4-methoxy (or 4-benzoyloxy) ~ 2-pyridones known which have a methyl, styryl, phenylethyl or phenylbutadienyl radical in the ^ -position and in the 5-position have a hydrogen atom or a carboxyl or carbethoxyl radical. A medicinal effect of these compounds is not described there.
3Q98Q7/13023Q98Q7 / 1302
070671070671
Gegenstand der Erfindung sind neue Arzneimittel mit insbesondere psychopharmakologiseher oder antiphlogistischer Wirkung, die dadurch gekennzeichnet sind, dass sie als Wirkstoff ein 2-Pyridon der allgemeinen FormelThe invention relates to new medicaments with, in particular, psychopharmacological or anti-inflammatory drugs Effect, which are characterized in that they are a 2-pyridone of the general formula as active ingredient
RJ
oder ein Salz solcher Verbindungen enthalten, worin bedeuten:R J
or contain a salt of such compounds, in which:
R C^-Cg-Alkyl, Cycloalkyl, gegebenenfalls substituiertes Aryl,R C ^ -Cg-alkyl, cycloalkyl, optionally substituted aryl,
R2 C1-C,--Alkyl, Aralkyl oder Acyl,R 2 C 1 -C, - alkyl, aralkyl or acyl,
R Wasserstoff, Carboxyl oder verestertes Carboxyl undR is hydrogen, carboxyl or esterified carboxyl and
R Alkyl, gegebenenfalls substituiertes 2-Aryläthenyl, gegebenenfalls substituiertes 2-Aryläthyl, gegebenenfalls substituiertes 4-Arylbutadienyl, gegebenenfalls substituiertes 4-Aryl- . butyl, 2-(C1-C/{-Alkyl)-äthenyl, 2-(Arylalkyl)-äthenyl, 2-(C1-C11-Alkyl)-äthyl oder 2-(Arylalkyl)-äthyl.R alkyl, optionally substituted 2-arylethyl, optionally substituted 2-arylethyl, optionally substituted 4-arylbutadienyl, optionally substituted 4-aryl-. butyl, 2- (C 1 -C / { -alkyl) -ethenyl, 2- (arylalkyl) -ethhenyl, 2- (C 1 -C 11 -alkyl) -ethyl or 2- (arylalkyl) -ethyl.
Bevorzugt hat der Rest R folgende Bedeutungen:" R = C1-Cg-AIlCyI bedeutet vorzugsweise Methyl oder Äthyl.The radical R preferably has the following meanings: "R = C 1 -Cg-AIlCyI preferably denotes methyl or ethyl.
R = gegebenenfalls substituiertes Aryl bedeutet insbesondere Phenyl, Halogenphenyl, vorzugsweise Chlor- oder Bromphenyl, Cj-C^-Alkoxyphenyl, vorzugsweise Methoxy- oder Äthoxyphenyl, C^C^-Alkylthiphenyl, Di-CC^-C^-alkyl)-aminophenyl, besonders Dimethylamxnophenyl, oder Trifluormethylphenyl, wobei sich diese Substituenten vorzugsweise in ο- oder p-Stellung befinden.R = optionally substituted aryl means in particular phenyl, halophenyl, preferably chloro- or bromophenyl, Cj-C ^ alkoxyphenyl, preferably methoxy or Ethoxyphenyl, C ^ C ^ -alkylthiphenyl, di-CC ^ -C ^ -alkyl) aminophenyl, especially dimethylaminophenyl, or trifluoromethylphenyl, these substituents are preferably in the ο- or p-position.
R = substituiertes Aryl kann auch einen 3,^-Methylendioxyphenyl-R = substituted aryl can also be a 3, ^ - methylenedioxyphenyl-
rest bedeuten.rest mean.
3 0 9 8 0 7/13023 0 9 8 0 7/1302
070671 2 070671 2
R = Cycloalkyl bedeutet insbesondere Cyclopentyl oder Cyclohexyl. R = cycloalkyl means in particular cyclopentyl or cyclohexyl.
2
Als Beispiele für R = Cj-C^-Alkyl seien genannt Methyl, Äthyl,2
Examples of R = Cj-C ^ -alkyl are methyl, ethyl,
Propyl und Butyl, wobei Methyl besonders bevorzugt ist. R =Propyl and butyl, with methyl being particularly preferred. R =
Aralkyl bedeutet bevorzugt Benzyl oder Phenyläthyl und R =Aralkyl is preferably benzyl or phenylethyl and R =
Acyl ist bevorzugt Benzoyl.Acyl is preferably benzoyl.
Wenn R einen veresterten Carboxylrest bedeutet, so kann dies ein Aryl-, Aralkyl-, Cycloalkyl- oder Alky!ester sein. Von diesen sind bevorzugt die C^-C^-Alkylester, insbesondere Methyl-, Äthyl- und tert.-Butylester.If R denotes an esterified carboxyl radical, this can an aryl, aralkyl, cycloalkyl or alkyl ester. Of these are preferred the C ^ -C ^ alkyl esters, especially methyl, Ethyl and tert-butyl esters.
Wenn R ein Alkylrest ist, so enthält dieser insbesondere 1 bis 4 Kohlenstoffatome und bedeutet vorzugsweise Methyl. Wenn im Rest R ein Arylrest vorkommt, so ist dies vorzugsweise ein Phenylrest, der in o- und/oder p-Stellung substituiert sein kann durch Halogen, insbesondere Chlor oder Brom, C ^-Cj,-Alkoxy, insbesondere Methoxy, C^-C^-Alkylthio, Di-(C1-CiJ-alkyl)-amino, insbesondere. Dimethylamine, oder Trifluormethyl. Ein solcher Phenylsübstituent des Restes R kann auch eine Methylendioxygruppe aufweisen. Von R = Arylalkyläthenyl ist Benzyläthenyl bevorzugt.If R is an alkyl radical, this contains in particular 1 to 4 carbon atoms and is preferably methyl. If an aryl radical occurs in the radical R, this is preferably a phenyl radical, which can be substituted in the o- and / or p-position by halogen, in particular chlorine or bromine, C ^ -Cj, alkoxy, especially methoxy, C ^ - C 1-4 alkylthio, di- (C 1 -C iJ -alkyl) -amino, in particular. Dimethylamine, or trifluoromethyl. Such a phenyl substituent of the radical R can also have a methylenedioxy group. Of R = arylalkylethenyl, benzylethenyl is preferred.
Die Wirkstoffe der erfindungsgemässen Arzneimittel können auch in Form ihrer Salze mit Basen vorliegen, wenn R^ einen Carboxylrest bedeutet. Hier kommen besonders die Alkali-, Erdalkali- und Aminsalze, beispielsweise das Salz mit Di-(hydroxyäthyl)-amin in Betracht. Wenn der Rest R durch einen Dialkylaminoarylrest substituiert ist, so können die Wirkstoffe der erfindungsgemässen Arzneimittel auch in Form ihrer Säureadditionssalze vorliegen.The active ingredients of the medicaments according to the invention can also be present in the form of their salts with bases if R ^ is a carboxyl radical means. Here come the alkali, alkaline earth and amine salts, for example the salt with di (hydroxyethyl) amine into consideration. When the radical R is replaced by a dialkylaminoaryl radical is substituted, the active ingredients of the medicaments according to the invention can also be present in the form of their acid addition salts.
In einer bevorzugten Gruppe von erfindungsgemäss verwendeten Wirkstoffen bedeutet R einen Äthylrest. Andere bevorzugte WirIn a preferred group of those used according to the invention Active ingredients, R means an ethyl radical. Others preferred us
-j stoffgruppen sind solche, bei denen R p-Chlorphenyl oder p--j substance groups are those in which R is p-chlorophenyl or p-
309807/1302309807/1302
070671 u ■ 070671 u ■ ■-'.-'■ -'.- '
2 "5 k 2 "5 k
Methoxyphenyl, R Methoxy oder Äthoxy, R^ Carboxy und RMethoxyphenyl, R methoxy or ethoxy, R ^ carboxy and R
gegebenenfalls in p-Stellung durch Chlor, Methoxy oder Dimethylamino substituiertes Phenyläthenyl bedeutet.optionally in the p-position by chlorine, methoxy or dimethylamino means substituted phenylethenyl.
Die erfindunsgemäss verwendetm Wirkstoffe können beispielsweise wie im folgenden beschrieben erhalten werden.The active ingredients used according to the invention can, for example can be obtained as described below.
Man setzt eine ß-Dicarbonylverbindung, wie Acetessigester, mit einem Amin zu einem Enamin um (vgl. H. Henecka in Houben Weyl-Müller, Methoden der organischen Chemie, Band 8 (1952), Seite 627) und dieses Enamin mit Malonsäure oder Malonsäuredichlorid zu einem Pyridon der allgemeinen FormelA ß-dicarbonyl compound, such as acetoacetic ester, is used with an amine to an enamine (cf. H. Henecka in Houben Weyl-Müller, Methods of Organic Chemistry, Volume 8 (1952), Page 627) and this enamine with malonic acid or malonic acid dichloride to form a pyridone of the general formula
C2H5OOC-C 2 H 5 OOC-
(vgl. E. Ziegler und F. Hradetzky, Mh. Chem. Band 95 Seite 1247). Die erhaltene 4-Hydroxyverbindung wird in an(see E. Ziegler and F. Hradetzky, Mh. Chem. Volume 95 Page 1247). The 4-hydroxy compound obtained is in an
sich bekannter Weise zu der 4-OR -Verbindung umgesetzt, beispielsweise durch Alkylierung mit Dimethylsulfat in Aceton in Gegenwart von Kaliumcarbonat. Aus den so erhaltenen Verbindungen kann man die Estergruppe in 5-Stellung entfernen, beispielsweise durch Umsetzung mit Bariumhydroxid. Man kann die 5-Carboxy1-Gruppe,falls gewünscht, nunmehr entfernen, z.B. durch Erhitzen. Die erhaltenen Verbindungen, die in 5~Stellung ein Wasserstoffatom oder eine gegebenenfalls veresterte Carboxyl-Gruppe aufweisen, kann man zur Herstellung der in 6-Stellung ungesättigten Verbindungen mit dem entsprechenden Aldehyd umsetzen, beispielsweise mit Benzaldehyd oder Zimtaldehyd in Äthanol unter Zugabe von Natriumäthylat. Bei dieser Umsetzung wird eine in 5-Stellung noch vorhandene Estergruppe verseift, so dass man die Estergruppe gegebenenfalls wieder in 5-Stellung einführenimplemented in a known manner to the 4-OR compound, for example by alkylation with dimethyl sulfate in acetone in the presence of potassium carbonate. From the compounds thus obtained the ester group in the 5-position can be removed, for example by reaction with barium hydroxide. One can use the 5-carboxy1 group, if now remove, e.g. by heating. The compounds obtained which have a hydrogen atom in the 5 ~ position or an optionally esterified carboxyl group can be used to prepare those unsaturated in the 6-position React compounds with the corresponding aldehyde, for example with benzaldehyde or cinnamaldehyde in ethanol Addition of sodium ethylate. In this implementation, an in The ester group still present in the 5-position is saponified, so that the ester group can optionally be reintroduced in the 5-position
309807/1302309807/1302
070671 ^ ."..'. 070671 ^. ".. '.
muss. Andererseits kann man die 5-Carboxyl-Gruppe auch wiederum jgot to. On the other hand, the 5-carboxyl group can also be used again j
entfernen. Durch Hydrierung der Doppe!bindung(en), die sich . jremove. By hydrogenating the double bond (s) that j
i im Rest in 6-Stellung findet (finden), beispielsweise mit Wasser- j stoff und einem Hydrierungskatalysator (z.B. Palladium/Kohle), j stellt man die entsprechenden in 6-Stellung gesättigten Verbindungen her.i in the remainder is (find) in the 6-position, for example with water j substance and a hydrogenation catalyst (e.g. palladium / carbon), the corresponding compounds which are saturated in the 6-position are prepared here.
Die erfindungsgemäss verwendeten Wirkstoffe sind kristalline
Substanzen. Nachfolgend ist eine Aufstellung von erfindungsgemäss verwendbaren Verbindungen wiedergegeben:The active ingredients used according to the invention are crystalline
Substances. A list of compounds that can be used according to the invention is given below:
3<L9Ä$7/13.Q23 <L9Ä $ 7 / 13th Q2
ORIGINAL INSPECTEDORIGINAL INSPECTED
Nr.No.
R"R "
R"R "
SchmelzpunktMelting point
235 224 221 241 219 176 228 140 241 234 217 150 110 238 2 35 202 288 166 130 171 202 129235 224 221 241 219 176 228 140 241 234 217 150 110 238 2 35 202 288 166 130 171 202 129
ο ..■■'■'.■ο .. ■■ '■'. ■
070671 ψ 070671 ψ
Weitere erfindungsgemäss verwendbare Wirkstoffe sind die folgenden:Further active ingredients which can be used according to the invention are following:
Rx R* R^ RR x R * R ^ R
Ph CH3 HPh CH 3 H
Ph CH3 COOHPh CH 3 COOH
Ph CH3 COOCH3 Ph CH 3 COOCH 3
Ph CH3 COOC2H5 Ph CH 3 COOC 2 H 5
Ph CH3 HPh CH 3 H
Ph CH3 COOHPh CH 3 COOH
Ph CH3 COOCH3 Ph CH 3 COOCH 3
Ph CH3 COOHPh CH 3 COOH
p-N(CH3)2-Ph CH HpN (CH 3 ) 2 -Ph CH H
p-N(CH3)2-Ph CH COOHpN (CH 3 ) 2 -Ph CH COOH
p-N(CH3)2-Ph CH3 COOC2HpN (CH 3 ) 2 -Ph CH 3 COOC 2 H
p-N(CH3)2-Ph CH3 HpN (CH 3 ) 2 -Ph CH 3 H
p-N(CH3)2-Ph CH3 COOHpN (CH 3 ) 2 -Ph CH 3 COOH
p-N(CH3)2-Ph CH3 COOCH3 pN (CH 3 ) 2 -Ph CH 3 COOCH 3
p-N(CH3)2-Ph CH3 COOHpN (CH 3 ) 2 -Ph CH 3 COOH
2 42 4
sowie entsprechende Verbindungen mit R = C2H,- und/oder Ras well as corresponding compounds with R = C 2 H, - and / or R
CH = CH-<S\ 0 bzw. CH2-CH2-CH = CH- <S \ 0 or CH 2 -CH 2 -
Die erfindungsgemäss verwendeten Verbindungen können zu Lösungen, Suspensionen, Tabletten, Dragees und Suppositorien verarbeitet wei-den.The compounds used according to the invention can be converted into solutions Processes suspensions, tablets, coated tablets and suppositories know.
Die verwendeten Wirkstoffmengen betragen 10 - 200 mg je Einzeldosis und I-*! Dosen pro Tag bei Dragees, Tabletten und Suppositorien, 2 - 100 mg je Einzeldosis und 1-3 Dosen pro Tag bei Injektionen. .The amounts of active ingredient used are 10-200 mg per single dose and I- *! Doses per day for dragees, tablets and suppositories, 2-100 mg per single dose and 1-3 doses per day for injections. .
309807/1302309807/1302
070671070671
Beispiel 1 Man stellt Tabletten folgender Zusammensetzung her: Example 1 Tablets are produced with the following composition:
N-(p-Methoxyphenyl)-4-methoxy-5-carboxy-6-(p-methoxy-styryl)-2-pyridon 150 mgN- (p-Methoxyphenyl) -4-methoxy-5-carboxy-6- (p-methoxystyryl) -2-pyridone 150 mg
Milchzucker 50 mgMilk sugar 50 mg
Maisstärke 23 mgCorn starch 23 mg
Talkum ■ 7 mgTalc ■ 7 mg
ψ Wirkstoff und Milchzucker werden mit Isopropanol granuliert; das Granulat wird mit den übrigen Bestandteilen gemuht und zu Tabletten gepresst. ψ The active ingredient and milk sugar are granulated with isopropanol; the granulate is milled with the other ingredients and pressed into tablets.
- Beispiel 2 - Example 2
Man verwendet die Mischung des Beispiels 1. Nach Pressen der Kerne werden diese auf übliche Weise dragiert.The mixture from Example 1 is used. After pressing the Cores are coated in the usual way.
Man stellt Kapseln der folgenden Zusammensetzung her:Capsules are made with the following composition:
N-(p-Methoxyphenyl)-4-methoxy-5-carboxy-6-(p-methoxy-styryl)-2-pyridon 150 mgN- (p-Methoxyphenyl) -4-methoxy-5-carboxy-6- (p-methoxystyryl) -2-pyridone 150 mg
Milchzucker _ 47 mgMilk sugar _ 47 mg
D-(+)-Lactose 23 ragD - (+) - lactose 23 rag
Wirkstoff und Milchzucker werden mit Isopropanol granuliert, mit der D-(+)-Lactose gemischt und in Hartgelatine-Kapseln eingefüllt. The active ingredient and milk sugar are granulated with isopropanol, mixed with the D - (+) - lactose and filled into hard gelatine capsules.
Beispiel H Man stellt Suppositorien folgender Zusammensetzung her: Example H Suppositories are made with the following composition:
309807/130309807/130
ν ·; ■■ ■■;;; ;. ,"2Ϊ40-712ν ·; ■■ ■■ ;;; ;. , "2Ϊ40-712
070671 V ' .070671 V '.
N-Cp-MethoxyphenyD-M-methoxy-S-carboxy-" 6-(p-methoxy-styryl)-2-pyridon 150 mgN-Cp-methoxyphenyD-M-methoxy-S-carboxy- " 6- (p-methoxystyryl) -2-pyridone 150 mg
Suppositorienmasse I85O mgSuppository mass I85O mg
Der Wirkstoff mit einer Korngrösse von 10 - 50 μ wird in der bei 40° C geschmolzenen Supposito: Zäpfchenformen a 2 g ausgegossen.The active ingredient with a particle size of 10 - 50 μ is in the Supposito melted at 40 ° C: suppository forms a 2 g poured out.
bei 40° C geschmolzenen Suppositorienmasse dispergiert und inat 40 ° C melted suppository mass dispersed and in
3~098"07/13Ö23 ~ 098 "07 / 13Ö2
Claims (1)
R Alkyl, gegebenenfalls substituiertes 2-Aryläthenyl, gegebenen·Ij
R alkyl, optionally substituted 2-arylethyl, given
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE787523D BE787523A (en) | 1971-08-13 | PYRIDONE-2 MEDICINAL PRODUCT | |
| DE2140712A DE2140712A1 (en) | 1971-08-13 | 1971-08-13 | MEDICINAL PRODUCTS CONTAINING 2-PYRIDONES |
| NL7210798A NL7210798A (en) | 1971-08-13 | 1972-08-07 | |
| FR7228676A FR2150750B1 (en) | 1971-08-13 | 1972-08-09 | |
| ZA725519A ZA725519B (en) | 1971-08-13 | 1972-08-11 | Medicines containing 2-pyridones |
| GB3765072A GB1388001A (en) | 1971-08-13 | 1972-08-11 | 2-pyridones and preparations comprising them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2140712A DE2140712A1 (en) | 1971-08-13 | 1971-08-13 | MEDICINAL PRODUCTS CONTAINING 2-PYRIDONES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2140712A1 true DE2140712A1 (en) | 1973-02-15 |
Family
ID=5816721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2140712A Pending DE2140712A1 (en) | 1971-08-13 | 1971-08-13 | MEDICINAL PRODUCTS CONTAINING 2-PYRIDONES |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE787523A (en) |
| DE (1) | DE2140712A1 (en) |
| FR (1) | FR2150750B1 (en) |
| GB (1) | GB1388001A (en) |
| NL (1) | NL7210798A (en) |
| ZA (1) | ZA725519B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1928454T1 (en) * | 2005-05-10 | 2015-01-30 | Intermune, Inc. | Pyridone derivatives for modulating stress-activated protein kinase system |
| JP5627574B2 (en) | 2008-06-03 | 2014-11-19 | インターミューン， インコーポレイテッド | Compounds and methods for treating inflammatory and fibrotic diseases |
| AR092742A1 (en) | 2012-10-02 | 2015-04-29 | Intermune Inc | ANTIFIBROTIC PYRIDINONES |
| KR102373700B1 (en) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | Anti-fibrotic pyridinones |
-
0
- BE BE787523D patent/BE787523A/en unknown
-
1971
- 1971-08-13 DE DE2140712A patent/DE2140712A1/en active Pending
-
1972
- 1972-08-07 NL NL7210798A patent/NL7210798A/xx not_active Application Discontinuation
- 1972-08-09 FR FR7228676A patent/FR2150750B1/fr not_active Expired
- 1972-08-11 ZA ZA725519A patent/ZA725519B/en unknown
- 1972-08-11 GB GB3765072A patent/GB1388001A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2150750A1 (en) | 1973-04-13 |
| FR2150750B1 (en) | 1976-08-20 |
| NL7210798A (en) | 1973-02-15 |
| BE787523A (en) | 1973-02-12 |
| ZA725519B (en) | 1973-04-25 |
| GB1388001A (en) | 1975-03-19 |
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