DE3050999C2 - Medicines containing 2-isopropylamino-4-hydroxypyrimidine - Google Patents
Medicines containing 2-isopropylamino-4-hydroxypyrimidineInfo
- Publication number
- DE3050999C2 DE3050999C2 DE3050999A DE3050999A DE3050999C2 DE 3050999 C2 DE3050999 C2 DE 3050999C2 DE 3050999 A DE3050999 A DE 3050999A DE 3050999 A DE3050999 A DE 3050999A DE 3050999 C2 DE3050999 C2 DE 3050999C2
- Authority
- DE
- Germany
- Prior art keywords
- isopropylamino
- hydroxypyrimidine
- medicaments
- contain
- effect
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Beispiel
2-Isopropylamino-4-hydroxypyrimidinexample
2-isopropylamino-4-hydroxypyrimidine
Das Ausgangs-Methylthiouracil wird dadurch erhalten, daß man Methyljodid mit Thiouracil in Gegenwart von Natriummethanolat umsetzt. Das so erhaltene Methylthiouracil (20 g; 0,14 Mol) wird zusammen mit 200 ml trockenem Toluol und 200 ml Isopropylamin in einen 1-1-Druckreaktor gebracht. Die Reaktion wird 24 h bei 110 bis 120°C unter Druck durchgeführt. Das resultierende Gemisch wird zur Trockene eingedampft, mit Aceton und Diäthyläther (50/50) behandelt, filtriert, mit Wasser gewaschen und in Isopropylacetat umkristallisiert. Auf diese Weise werden 17 g eines weißen kristallinen Produkts (Ausbeute 84%) mit einem Schmelzpunkt von 14O0C erhalten. Die Analyse des Produkts zeigt eine gute Übereinstimmung mit der Formel C7HnN3O. Es wird auch das Hydrochlorid dieser Verbindung (Schmelzpunkt 233 bis 234° C (Tottoli)) hergestellt, das gleichfalls ein weißes kristallines Produkt ist. Die entsprechenden Werte des UV-Spektrums sind wie folgt:The starting methylthiouracil is obtained by reacting methyl iodide with thiouracil in the presence of sodium methoxide. The methylthiouracil thus obtained (20 g; 0.14 mol) is placed in a 1-1 pressure reactor together with 200 ml of dry toluene and 200 ml of isopropylamine. The reaction is carried out under pressure at 110 to 120 ° C. for 24 hours. The resulting mixture is evaporated to dryness, treated with acetone and diethyl ether (50/50), filtered, washed with water and recrystallized from isopropyl acetate. In this manner, 17 g of a white crystalline product (yield 84%) with a melting point of 14O 0 C was obtained. Analysis of the product shows good agreement with the formula C 7 H n N 3 O. The hydrochloride of this compound (melting point 233 to 234 ° C. (Tottoli)) is also prepared, which is also a white crystalline product. The corresponding values of the UV spectrum are as follows:
In Wasser (für das Hydrochlorid)In water (for the hydrochloride)
In Methanol (für die Base)In methanol (for the base)
£lcmr-1%
£ lcm
£lcmr-1%
£ lcm
Xmax: = 293 nm
Xmax\ = 222 nm X max : = 293 nm
X max = 222 nm
E\'L = 510 E[L = 730 E \ 'L = 510 E [L = 730
Die Base ist ein weißes kristallines Produkt (Molekulargewicht 153,18), das in Wasser unlöslich, jedoch in Chloroform löslich ist.The base is a white crystalline product (molecular weight 153.18) which is insoluble in water but in Chloroform is soluble.
Toxizitättoxicity
Die akute Toxizität (mg/kg) von 2-Isopropylamino-4-hydroxypyrimidin wurde bei der Maus intraperitoneal und per os bestimmt. Die erhaltenen Werte sind in der folgenden Tabelle zusammengestellt:The acute toxicity (mg / kg) of 2-isopropylamino-4-hydroxypyrimidine was determined intraperitoneally in the mouse and determined per os. The values obtained are summarized in the following table:
VerabreichungswegRoute of administration
2-Isopropylamino-4-hydroxypyrimidin 2-isopropylamino-4-hydroxypyrimidine
2-IsopropyIamino-2-isopropylamino-
pyrimidin-ortho-pyrimidine-ortho-
phosphatphosphate
(DE 27 07 095)(DE 27 07 095)
Intraperitoneal Per osIntraperitoneal per os
1530 28301530 2830
Pharmakologiepharmacology
Die pharmakologische Aktivität von 2-Isopropy!amino-4-hydroxypyrimidin wurde durch die folgenden Ver gleichsversuche über die Regenerierung des Ischiasnervs von männlichen ausgewachsenen Ratten (Wistar) ermittelt.The pharmacological activity of 2-isopropylamino-4-hydroxypyrimidine was determined by the following Ver Similar experiments on the regeneration of the sciatic nerve in male adult rats (Wistar) determined.
Eine Läsion des Ischiasnervs von Ratten wurde dadurch bewirkt, daß 20 min lang eine Thennosonde von -20° C an den Nerv angelegt wurde. Sodann wurden die Ratten intraperitoneal mit dem Vergleichsprodukt oder mit 2-Isopropylamino-4-hydroxypyrimidin während einer vorbestimmten Dauer behandelt Danach wurden die Ratten getötet, und der Ischiasnerv wurde herausgetrennt. Dieser wurde mit einer Reihe von 70 dünnen parallelen Platindrähten (Abstand 1 mm) in Kontakt gebracht. Ein elektrisches Signal, das stromaufwärts der Läsionsstelle ausgesandt wurde, wurde mittels der Platindrähte erfaßt: der entferntere Draht, an dem das Signal empfangen werden kann, ergibt die regenerierte Länge.A rat sciatic nerve lesion was caused by a thennoprobe of -20 ° C was applied to the nerve. The rats were then given the comparative product intraperitoneally or treated with 2-isopropylamino-4-hydroxypyrimidine for a predetermined period Rats were killed and the sciatic nerve was excised. This one was made with a series of 70 thin parallels Platinum wires (distance 1 mm) brought into contact. An electrical signal that is upstream of the lesion site was detected by means of the platinum wires: the more distant wire on which the signal was received can be, gives the regenerated length.
Für jede Testzusammensetzung und jede Behandlungsdauer wurde eine Gruppe von 8 Ratten verwendet.A group of 8 rats was used for each test composition and treatment period.
Zwei Mittel wurden intraperitoneal getestet: die Verbindung des Beispiels und als Vergleichssubstanz 2-Isopropylaminopyrimidin-orthophosphat (DE 27 07 095). Die Kontrolltiere erhielten überhaupt keine Behandlung. Fünf Gruppen mit je 8 Tieren wurden für jede Dauer (7,11,14,17 und 21 Tage) sowohl für die Kontrollprobe als auch für die Verbindung des Beispiels oder die Vergleichsverbindung verwendet.Two agents were tested intraperitoneally: the compound of the example and, as a comparison substance, 2-isopropylaminopyrimidine orthophosphate (DE 27 07 095). The control animals received no treatment at all. Five groups of 8 animals each were given for each duration (7, 11, 14, 17 and 21 days) for both the control sample as well as used for the connection of the example or the comparison connection.
Die erhaltenen Versuchsergebnisse sind in der folgenden Tabelle zusammen mit den für die Kontrolltiere erhaltenen Werten zusammengestellt. Die Länge der regenerierten Nerven ist in mm in den entsprechenden Spalten der Tage angegeben. Es handelt sich um einen Mittelwert der Längen, die bei allen Tieren jeder Gruppe gemessen wurden. Wenn kein Wert angegeben ist (17 und 21 Tage), dann bedeutet dies, daß die Regenerierungslänge über die Länge der genommenen Probe hinausging. The test results obtained are in the following table together with those for the control animals values obtained. The length of the regenerated nerves is in mm in the corresponding Columns of days given. It is an average of the lengths found in all animals in each group were measured. If no value is given (17 and 21 days) it means that the regeneration length exceeded the length of the sample taken.
1010
2020th
Verbindung und Dosis intraperitonealConnection and dose intraperitoneally
Versuchsdauer (Tage) 7 11 14Test duration (days) 7 11 14
1717th
2121
2525th
10 mg/kgConnection of the example
10 mg / kg
(DE 27 07 095)
145 mg/kg (entsprechend 87 mg/kg freie Base)2-isopropylaminopyrimidine orthophosphate
(DE 27 07 095)
145 mg / kg (corresponding to 87 mg / kg free base)
17,817.8
22,422.4
Die erfindungsgemäß verwendete Verbindung zeigt überraschenderweise eine günstigere Relation von wirksamer zu letaler Dosis als die Vergleichsverbindung bei größerer Regenerierungslänge nach 14 Tagen.The compound used according to the invention surprisingly shows a more favorable ratio of more effective a lethal dose than the comparison compound with a longer regeneration length after 14 days.
Darreichung - DosiologiePresentation - Dosiology
2-Isopropylamino-4-hydroxypyrimidin kann in jeder beliebigen therapeutisch annehmbaren Form, beispielsweise in Tabletten oder in Gelatinekapseln, die 5 mg Wirkstoff pro Dosiseinheit zusammen mit einem Streckmittel enthalten, verabreicht werden. Für injizierbare Zubereitungen kann das Produkt in Ampullen dosiert werden, die mindestens 1 mg Wirkstoff in Form des Hydrochlorids, gelöst in Wasser, enthalten. In der Humanmedizin erfordert die orale Verabreichung 20 mg bis 1 g pro Tag, während injizierbare Zubereitungen in Dosen zwischen 1 mg und 50 mg pro Tag verabreicht werden können.2-Isopropylamino-4-hydroxypyrimidine can be in any therapeutically acceptable form, for example in tablets or in gelatin capsules containing 5 mg of active ingredient per dose unit together with an excipient contain, are administered. For injectable preparations, the product can be dosed in ampoules that contain at least 1 mg of active ingredient in the form of the hydrochloride dissolved in water. In human medicine Oral administration requires 20 mg to 1 g per day while injectable preparations are in doses between 1 mg and 50 mg per day can be administered.
Nachstehend wird ein Beispiel für eine Tablettenform angegeben:An example of a tablet shape is given below:
100 mg100 mg
3030th
3535
4040
4545
5050
5555
6060
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB7908494 | 1979-03-10 | ||
GB7914987 | 1979-04-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE3050999A1 DE3050999A1 (en) | 1985-08-14 |
DE3050999C2 true DE3050999C2 (en) | 1986-08-14 |
Family
ID=26270867
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3050999A Expired DE3050999C2 (en) | 1979-03-10 | 1980-03-10 | Medicines containing 2-isopropylamino-4-hydroxypyrimidine |
DE3009071A Expired DE3009071C2 (en) | 1979-03-10 | 1980-03-10 | 2-isopropylamino-hydroxypyrimidine compounds, processes for their preparation and pharmaceuticals containing these compounds |
DE19803016752 Granted DE3016752A1 (en) | 1979-03-10 | 1980-04-30 | METHOD FOR PRODUCING 2-ISOPROPYLAMINOPYRIMIDINE HYDROXY DERIVATIVES |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3009071A Expired DE3009071C2 (en) | 1979-03-10 | 1980-03-10 | 2-isopropylamino-hydroxypyrimidine compounds, processes for their preparation and pharmaceuticals containing these compounds |
DE19803016752 Granted DE3016752A1 (en) | 1979-03-10 | 1980-04-30 | METHOD FOR PRODUCING 2-ISOPROPYLAMINOPYRIMIDINE HYDROXY DERIVATIVES |
Country Status (24)
Country | Link |
---|---|
JP (1) | JPS55122768A (en) |
AR (1) | AR222691A1 (en) |
AU (1) | AU533547B2 (en) |
BE (1) | BE881752A (en) |
CA (1) | CA1132561A (en) |
CH (1) | CH644368A5 (en) |
DE (3) | DE3050999C2 (en) |
EG (1) | EG14282A (en) |
FI (1) | FI66357C (en) |
FR (2) | FR2451370A1 (en) |
GB (1) | GB2045756B (en) |
HK (1) | HK55383A (en) |
IE (1) | IE49547B1 (en) |
IN (1) | IN153791B (en) |
LU (1) | LU82185A1 (en) |
MX (1) | MX6218E (en) |
MY (1) | MY8400200A (en) |
NL (1) | NL184833C (en) |
NO (1) | NO154054C (en) |
NZ (1) | NZ192927A (en) |
OA (1) | OA06484A (en) |
PT (1) | PT70882A (en) |
SE (1) | SE435180B (en) |
SG (1) | SG22683G (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE894517A (en) * | 1981-10-16 | 1983-01-17 | Sod Conseils Rech Applic | NEW ISOPROPYLAMINO PYRIMIDINE DERIVATIVE, ITS PREPARATION AND THERAPEUTIC COMPOSITION BASED ON ITS COMPOUNDS |
US4554276A (en) * | 1983-10-03 | 1985-11-19 | Pfizer Inc. | 2-Amino-5-hydroxy-4-methylpyrimidine derivatives |
US4673677A (en) * | 1983-10-03 | 1987-06-16 | Pfizer Inc. | Method for treatment of gastrointestinal disorders |
US4711888A (en) | 1985-07-24 | 1987-12-08 | Pfizer Inc. | Hydroxy and alkoxy pyrimidines |
WO1989000423A1 (en) * | 1987-07-09 | 1989-01-26 | Pfizer Inc. | 2-amino-5-hydroxy-4-pyrimidones |
US4910204A (en) * | 1988-06-28 | 1990-03-20 | Pfizer Inc. | 2-amino-5-hydroxy-4-pyrimidones |
US5264435A (en) * | 1988-12-29 | 1993-11-23 | Mitsui Petrochemical Industries, Ltd. | Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines |
HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
US4940712A (en) * | 1989-05-26 | 1990-07-10 | Pfizer Inc. | Derivatives of hydroxyprimidines as leukotriene synthesis inhibitors |
US5270319A (en) * | 1991-09-09 | 1993-12-14 | Warner-Lambert Company | 5-hydroxy-2-pyrimidinylmethylene derivatives useful as antiinflammatory agents |
US5196431A (en) * | 1992-02-24 | 1993-03-23 | Warner-Lambert Company | 2-substituted amino-4, 6-di-tertiary-buthyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents |
US5220025A (en) * | 1992-02-24 | 1993-06-15 | Warner-Lambert Company | 2-substituted amino-4, 6-di-tertiary-butyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents |
US9133212B1 (en) * | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB741667A (en) * | 1952-12-05 | 1955-12-07 | Ici Ltd | New pyrimidine derivatives |
GB756189A (en) * | 1954-02-01 | 1956-08-29 | Ici Ltd | New pyrimidine derivatives |
ZA711152B (en) * | 1970-03-02 | 1971-11-24 | Ici Ltd | Manufacture of pyrimidines |
GB1525995A (en) * | 1976-02-18 | 1978-09-27 | Soc D Etudes Prod Chimique | Aminopyrimidine salt |
-
1980
- 1980-02-12 IN IN103/DEL/80A patent/IN153791B/en unknown
- 1980-02-15 BE BE0/199421A patent/BE881752A/en not_active IP Right Cessation
- 1980-02-20 NZ NZ192927A patent/NZ192927A/en unknown
- 1980-02-20 LU LU82185A patent/LU82185A1/en unknown
- 1980-02-26 FI FI800566A patent/FI66357C/en not_active IP Right Cessation
- 1980-02-27 AR AR280106A patent/AR222691A1/en active
- 1980-02-29 PT PT70882A patent/PT70882A/en unknown
- 1980-03-03 CH CH165080A patent/CH644368A5/en not_active IP Right Cessation
- 1980-03-04 NL NLAANVRAGE8001289,A patent/NL184833C/en not_active IP Right Cessation
- 1980-03-04 CA CA346,981A patent/CA1132561A/en not_active Expired
- 1980-03-07 IE IE477/80A patent/IE49547B1/en unknown
- 1980-03-07 GB GB8007908A patent/GB2045756B/en not_active Expired
- 1980-03-07 SE SE8001812A patent/SE435180B/en not_active IP Right Cessation
- 1980-03-07 AU AU56248/80A patent/AU533547B2/en not_active Ceased
- 1980-03-07 NO NO800664A patent/NO154054C/en unknown
- 1980-03-09 EG EG131/80A patent/EG14282A/en active
- 1980-03-10 DE DE3050999A patent/DE3050999C2/en not_active Expired
- 1980-03-10 MX MX808702U patent/MX6218E/en unknown
- 1980-03-10 FR FR8005278A patent/FR2451370A1/en active Granted
- 1980-03-10 FR FR8005277A patent/FR2451191A1/en active Granted
- 1980-03-10 JP JP2931280A patent/JPS55122768A/en active Granted
- 1980-03-10 OA OA57049A patent/OA06484A/en unknown
- 1980-03-10 DE DE3009071A patent/DE3009071C2/en not_active Expired
- 1980-04-30 DE DE19803016752 patent/DE3016752A1/en active Granted
-
1983
- 1983-04-28 SG SG226/83A patent/SG22683G/en unknown
- 1983-11-17 HK HK553/83A patent/HK55383A/en unknown
-
1984
- 1984-12-30 MY MY200/84A patent/MY8400200A/en unknown
Non-Patent Citations (1)
Title |
---|
NICHTS-ERMITTELT |
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