EP0000334A1 - 2,4-Diamino-5-benzylpyrimidines, procédé pour leur préparation et médicaments les contenant - Google Patents
2,4-Diamino-5-benzylpyrimidines, procédé pour leur préparation et médicaments les contenant Download PDFInfo
- Publication number
- EP0000334A1 EP0000334A1 EP78100180A EP78100180A EP0000334A1 EP 0000334 A1 EP0000334 A1 EP 0000334A1 EP 78100180 A EP78100180 A EP 78100180A EP 78100180 A EP78100180 A EP 78100180A EP 0000334 A1 EP0000334 A1 EP 0000334A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- radical
- trimethoxybenzyl
- carbon atoms
- amino
- general formula
- 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
- 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
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Definitions
- the invention relates to new benzylpyrimidines of the general formula I.
- R 1 , R 2 and R 3 which are the same or different from one another, denote hydrogen, methyl, methoxy or chlorine
- R 4 denotes a straight-chain or branched, saturated or unsaturated alkyl radical having 1 to 10 C atoms, the carbon chain of which can be interrupted by 1 to 3 oxygen atoms and / or can form a cycloaliphatic ring with 5 or 6 carbon atoms in the ring and can be substituted by a chlorine atom, a hydroxyl group or a secondary amino group, the nitrogen atom of which is also part of a can be aliphatic ring-shaped amine, or is -alk-R 5 , where alk is a straight or branched alkylene radical having 1 to 4 carbon atoms and R 5 is the phenyl radical which is optionally substituted by chlorine or C 2-4 -alkyl or a heteroaromatic ring with
- Substituents R 4 can be, for example, methoxymethyl, n-butyloxymethyl, cyclohexyloxymethyl, ß-chloroethyloxymethyl, ⁇ -ethoxyethoxymethyl, ß-methoxyäthoxymethyl, ⁇ -chloro- ⁇ -methyl-äthoxymethyl, ß-dimethylaminoethyl, ß-morpholinoethyl, ß-morpholinoethyl, ß Dimethylaminopropyl, allyloxymethyl, benzyloxymethyl, benzyl, 4-chlorobenzyl, phenethyl, 3-methylisoxazolylmethyl-2, 3-tertiary butylisoxazolylmethyl-2, ß-hydroxyethyl.
- R 4 is a methyl radical which is substituted by an alkoxy radical having 1 to 6 C atoms, the alkyl radical of which is optionally additionally substituted by a chlorine atom or an alkoxy group having 1 to 2 C atoms in the Alkyl radical, which in turn can be substituted by an alkoxy radical having 1 to 4 carbon atoms, an allyloxy radical, a cyclohexyloxy radical or a benzyloxy radical, or R 4 denotes allyl or an alkyl radical having 1 to 3 carbon atoms, which is substituted by phenyl, chlorophenyl, Hydroxy, alkoxy with 1 to 2 carbon atoms, dialkylamino with 1 to 2 carbon atoms in the alkyl or a pyrrolidino or morpholino radical is substituted or R 4 is a 3-alkylisoxazolyl-5-methyl radical with 1 to 4 carbon atoms in alkyl.
- the substituents R 1 , R 2 and R 3 are preferably in the 3, 4 and 5 positions of the benzene ring.
- R 4 is the radical -alk-OR 6 , where R 6 is hydrogen, a straight-chain or branched chain, optionally with chlorine or lower alkoxy having 1 to 4 carbon atoms sub substituted alkyl radical with 1 to 6 carbon atoms, the cyclohexyl, phenyl or benzyl radical and alk represents a straight or branched chain alkylene radical with 1 to 4 carbon atoms.
- the compounds of the formula I and their salts are antimicrobially active in diseases caused by bacteria and protozoa and potentiate, combined with sulfonamides, their antimicrobial action. They can be used, for example, for bacterial diseases of the respiratory, digestive and urinary tract, as well as for throat, nose and ear infections and general systemic infectious diseases and malaria.
- Examples of such sulfonamides are: 2-sulfanilamidopyrimidine, 2-sulfanilamido-5-methoxypyrimidine, 4-sulfanilamido-2,6-dimethoxypyrimidine, 3-sulfanilamido-5-methylisoxazole, 2-sulfanilamido-4,5-dimethyloxazole, 3 -Sulfanilamido-6-methoxypyridazine, 4-sulfanilamido-2,6-dimethylpyrimidine, 4-sulfanilamido-5,6-dimethoxypyrimidine, 2-sulfanilamido-3-methoxypyrazine.
- the compounds of the formula I and their salts can be combined with the sulfonamides mentioned by way of example in various mixing ratios, the ratio of substance according to formula I: sulfonamide can vary in the range from 1:10 to 5: 1. However, preferred mixing ratios are 1: 1 to 1: 5. As a rule, 20 to 500 mg of an active ingredient of the formula I are suitable as doses.
- Procedure a) is generally carried out in an aprotic diluent, such as, for example, dioxane, tetrahydrofuran, benzene, chlorobenzene, chloroform or pyridine, the reaction temperatures being between 0 and 200 ° C., depending on the reactivity of the compound of the general formula III.
- an aprotic diluent such as, for example, dioxane, tetrahydrofuran, benzene, chlorobenzene, chloroform or pyridine
- Procedure b) is carried out in alcohols, preferably in methanol or ethanol, or in dimethylformamide or dimethyl sulfoxide as the solvent, the reaction temperatures being between 50 and 150.degree. Temperatures around 150 ° C are required when the leaving group X is a difficult to react aliphatic amino group.
- the leaving group in formula IV means an alkoxy group, preferably the methoxy and the ethoxy group, or a secondary aliphatic amino group, preferably a morpholino or dimethylamino group, or a primary aromatic amino group, preferably the anilino group or the imidazolyl-1 radical.
- the present invention accordingly also relates to chemotherapeutic agents which, in addition to conventional carriers and diluents, contain a compound of the formula I, in particular in combination with a sulfonamide, as active ingredients, and the use of the compounds of the formula I as sulfonamide potentiators.
- chemotherapeutic agents or preparations are produced in a known manner with the usual carriers or diluents and the commonly used pharmaceutical-technical auxiliaries in accordance with the desired type of application.
- the preferred preparations are in a dosage form which is suitable for oral administration.
- Dosage forms of this type are, for example, tablets, film-coated tablets, dragees, capsules, pills, powders, solutions or suspensions.
- the active ingredients are mixed with corn starch and granulated with an aqueous gelatin solution.
- the dry granulate is sieved and mixed with the aggregates. Tablets are pressed from this mixture in the usual way.
- the active ingredients are granulated with aqueous gelatin solution and, after drying, mixed with corn starch, talc and magnesium stearate. Tablets are pressed from this mixture in the usual way.
- the finely ground active ingredients are suspended in the aqueous tylose mucus. Then all other ingredients are added in succession with stirring. Finally, make up to 100.0 g with water.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19772730467 DE2730467A1 (de) | 1977-07-06 | 1977-07-06 | Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
DE2730467 | 1977-07-06 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000334A1 true EP0000334A1 (fr) | 1979-01-24 |
EP0000334B1 EP0000334B1 (fr) | 1981-08-12 |
Family
ID=6013252
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100180A Expired EP0000334B1 (fr) | 1977-07-06 | 1978-06-16 | 2,4-Diamino-5-benzylpyrimidines, procédé pour leur préparation et médicaments les contenant |
Country Status (17)
Country | Link |
---|---|
US (1) | US4279899A (fr) |
EP (1) | EP0000334B1 (fr) |
JP (1) | JPS5416482A (fr) |
AR (1) | AR223465A1 (fr) |
AT (1) | AT361931B (fr) |
AU (1) | AU515661B2 (fr) |
CA (1) | CA1102324A (fr) |
DE (2) | DE2730467A1 (fr) |
DK (1) | DK142578C (fr) |
FI (1) | FI782173A (fr) |
HU (1) | HU179407B (fr) |
IE (1) | IE781308L (fr) |
IL (1) | IL55018A (fr) |
IN (1) | IN149577B (fr) |
IT (1) | IT7825220A0 (fr) |
NO (1) | NO782340L (fr) |
ZA (1) | ZA783873B (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT385033B (de) * | 1981-06-26 | 1988-02-10 | Egyt Gyogyszervegyeszeti Gyar | Verfahren zur herstellung von 2,4-diamino-5(3',4',5'-trimethoxy-benzyl)-pyrimidin |
AT387961B (de) * | 1981-06-26 | 1989-04-10 | Egyt Gyogyszervegyeszeti Gyar | Verfahren zur herstellung von alpha-(3,4,5-trimethoxybenzyl)-beta-(2alkoxy|thoxy)-acrylnitrilen |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4438267A (en) * | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
DE3045720A1 (de) * | 1980-12-04 | 1982-07-08 | Basf Ag, 6700 Ludwigshafen | N-pyrimidinyl-carbaminsaeureester, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
JP4460292B2 (ja) * | 2001-10-17 | 2010-05-12 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | ピリミジン誘導体、これらの化合物を含む医薬組成物、その使用及びその調製方法 |
AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
EP2560488B1 (fr) | 2010-04-23 | 2015-10-28 | Cytokinetics, Inc. | Aminopyridines et aminotriazines, leurs compositions et leurs procédés d'utilisation |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2649449A (en) * | 1952-04-04 | 1953-08-18 | Nepera Chemical Co Inc | 2-cyclohexylamino-4-amino-5-benzylpyrimidine |
US2723975A (en) * | 1952-04-03 | 1955-11-15 | Nepera Chemical Co Inc | 2, 4-di-piperidino-5-benzylpyrimidine |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3049544A (en) * | 1962-08-14 | Method for the preparation of | ||
CH376115A (de) * | 1957-12-06 | 1964-03-31 | Ciba Geigy | Verfahren zur Herstellung neuer substituierter Pyrimidine |
US3515783A (en) | 1967-10-20 | 1970-06-02 | Hoffmann La Roche | Antibacterial composition containing 5-methyl - 3 - sulfanilamidoisoxazole and trimethoxybenzyl pyrimidine |
US4115650A (en) * | 1976-11-17 | 1978-09-19 | Hoffmann-La Roche Inc. | Process for preparing 2,4-diamino-5-(substituted benzyl)-pyrimidines |
-
1977
- 1977-07-06 DE DE19772730467 patent/DE2730467A1/de not_active Withdrawn
-
1978
- 1978-06-16 EP EP78100180A patent/EP0000334B1/fr not_active Expired
- 1978-06-16 DE DE7878100180T patent/DE2860928D1/de not_active Expired
- 1978-06-27 US US05/919,505 patent/US4279899A/en not_active Expired - Lifetime
- 1978-06-27 IL IL55018A patent/IL55018A/xx unknown
- 1978-06-29 IE IE781308A patent/IE781308L/xx unknown
- 1978-06-30 AU AU37644/78A patent/AU515661B2/en not_active Expired
- 1978-06-30 IT IT7825220A patent/IT7825220A0/it unknown
- 1978-07-04 AR AR272831A patent/AR223465A1/es active
- 1978-07-04 CA CA306,732A patent/CA1102324A/fr not_active Expired
- 1978-07-04 HU HU78BA3672A patent/HU179407B/hu unknown
- 1978-07-05 NO NO782340A patent/NO782340L/no unknown
- 1978-07-05 FI FI782173A patent/FI782173A/fi not_active Application Discontinuation
- 1978-07-05 AT AT487478A patent/AT361931B/de not_active IP Right Cessation
- 1978-07-05 DK DK303178A patent/DK142578C/da active
- 1978-07-05 ZA ZA00783873A patent/ZA783873B/xx unknown
- 1978-07-06 JP JP8153078A patent/JPS5416482A/ja active Pending
- 1978-07-06 IN IN747/CAL/78A patent/IN149577B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2723975A (en) * | 1952-04-03 | 1955-11-15 | Nepera Chemical Co Inc | 2, 4-di-piperidino-5-benzylpyrimidine |
US2649449A (en) * | 1952-04-04 | 1953-08-18 | Nepera Chemical Co Inc | 2-cyclohexylamino-4-amino-5-benzylpyrimidine |
Non-Patent Citations (1)
Title |
---|
JOURNAL OF MEDICINAL AND PHARMACEUTICAL CHEMISTRY, vol. 5, Nov. 1962 Seiten 1.103-1.123 (The American Chemical Society): 5-Benzyl-2,4-diamino-pyrimidines as Antibaterial Agents. I. Synthesis and Antibacterial Activity in vitro: by B. Roth, E.A. Falco, G.H. Hitchings & S.R.M. Bushby. * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT385033B (de) * | 1981-06-26 | 1988-02-10 | Egyt Gyogyszervegyeszeti Gyar | Verfahren zur herstellung von 2,4-diamino-5(3',4',5'-trimethoxy-benzyl)-pyrimidin |
AT387961B (de) * | 1981-06-26 | 1989-04-10 | Egyt Gyogyszervegyeszeti Gyar | Verfahren zur herstellung von alpha-(3,4,5-trimethoxybenzyl)-beta-(2alkoxy|thoxy)-acrylnitrilen |
Also Published As
Publication number | Publication date |
---|---|
ZA783873B (en) | 1979-08-29 |
AT361931B (de) | 1981-04-10 |
FI782173A (fi) | 1979-01-07 |
AR223465A1 (es) | 1981-08-31 |
IL55018A (en) | 1983-03-31 |
IN149577B (fr) | 1982-01-30 |
NO782340L (no) | 1979-01-09 |
ATA487478A (de) | 1980-09-15 |
AU515661B2 (en) | 1981-04-16 |
IT7825220A0 (it) | 1978-06-30 |
JPS5416482A (en) | 1979-02-07 |
US4279899A (en) | 1981-07-21 |
AU3764478A (en) | 1980-01-03 |
DK142578B (da) | 1980-11-24 |
DE2860928D1 (en) | 1981-11-12 |
HU179407B (en) | 1982-10-28 |
CA1102324A (fr) | 1981-06-02 |
DK142578C (da) | 1981-07-20 |
IE781308L (en) | 1979-01-06 |
DK303178A (da) | 1979-01-07 |
EP0000334B1 (fr) | 1981-08-12 |
IL55018A0 (en) | 1978-08-31 |
DE2730467A1 (de) | 1979-01-18 |
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