US3846428A - Nitrofurylpyrimidines - Google Patents

Nitrofurylpyrimidines Download PDF

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Publication number
US3846428A
US3846428A US00235426A US23542672A US3846428A US 3846428 A US3846428 A US 3846428A US 00235426 A US00235426 A US 00235426A US 23542672 A US23542672 A US 23542672A US 3846428 A US3846428 A US 3846428A
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Prior art keywords
furyl
pyrimidine
ethoxy
nitro
compound
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E Schroder
R Albrecht
H Kessler
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Bayer Pharma AG
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Schering AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • ABSTRACT Compounds of the formula I I N /R 0 wherein R is saturated or unsaturated, straight-chain or branched hydrocarbon aliphatic group of 1-6 carbon atoms or cyclic alkyl of 3-7 carbon atoms, alkyl Fa ho 19 1 einl $199!
  • om are substituted by hydroxy or by acyloxy of l-6 carbon atoms or one carbon atom thereof is substituted by alkoxy of l-6 carbon atoms, by dialkylamino wherein each alkyl group contains l-6 carbon atoms, by tetrahydrofuryl or phenyl and R is hydrogen or acyl of l-6 carbon atoms possess systemic anti-bacterial activity in addition to activity against Trichomonas vaginalis.
  • alkyl and acyl in each instance contain l-6 carbon atoms and cyclic alkyl preferably contains 3-7 carbon atoms.
  • R is H or acetyl
  • b/R is alkyl of l-6 carbon'atoms, preferably l-4, in-
  • R can also be a corresponding unsaturated group, e.g., allyl and ethynyl;
  • R is alkyl as defined in (b) substituted with l-2 of a hydroxy and acyloxy, e.g.,.acetoxy, preferably in the l or 2 position, e;g., those of (a);
  • R is alkyl as defined in (b) substituted with dialkylamino, e.g., dimet'hylamino, methylethylamino, dicthylamino, preferably in the 2 position, e.g., those of (a);
  • dialkylamino e.g., dimet'hylamino, methylethylamino, dicthylamino, preferably in the 2 position, e.g., those of (a);
  • the compound is in the form of an acid addition salt, e.g., hemisulfate of hydrochloride including those of (a), (b), (c) and (d).
  • acid addition salt e.g., hemisulfate of hydrochloride
  • cycloalkyl are cyclopropyl, cyclopentyl and cyclohexyl.
  • acyloxy examples are formyloxy, acetoxy, propionyloxy, butyryloxy and other alkanoyloxy.
  • alkoxy examples are methoxy, ethoxy, propoxy, i-propoxy and n-butoxy.
  • the tetrahydrofuryl substituent is preferably at the 1 -position and preferably attached by the 2-carbon atom thereof.
  • the phenyl group is preferably at the 1-position.
  • the compounds of this invention which are sufficiently basic to form acid addition salts can be in-the form of physiologically acceptable acid addition salts.
  • this invention embraces compounds of Formula I both in free base form and in the form of an acid addition salt with a physiologically compatible acid.
  • physiologically acceptable acids are hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid, succinic acid, tartaric acid, citric acid, benzoic acid, salicylic acid, nicotinic acid and heptagluconic acid.
  • acid addition salts i.e., of acids which do not materially increase the toxicity of the compounds of this v invention, include salts of other mineral acids, such as, forexample, hydriodic, hydrobromic, metaphospho'ric and .nitric as well as salts of organic acids, such as, for example, malic, glycolic, gluconic and arylsulfonic, e.g., p-toluenesulfonic acids. H I f
  • the acid addition salts of this invention are not limited to those formed with pharmaceutically acceptable acids.
  • Other acids e.g., those formed with perchloric and other toxic and/or unstable acids are useful for isolation, characterization and purification of the free base. These acid addition salts can, if desired, thereafter be converted back to the free base and acid addition salts of pharmeceutically acceptable acids, employing conventional procedures.
  • This invention relates both to single compounds of Formula I and to mixtures of one or more thereof.
  • the compounds of Formula I are produced by reacting a compound of the general Formula II 'ocrr CH-Z o N 2 2 wherein R" is hydrogen or nitro, and Z is a sulfonic acid ester group, a bromine or chlorine, with a primary amine of the general Formula R-NH (Ill) wherein R has the values given above; and subsequently hitrating the thus-obtained compounds wherein R" H and, optionally, prior to or after thenitration, acylating the amino group and/or any hydroxy groups present and/or saponifying the acylamino group and/or any acyloxy groups present; and optionally isolating the amino compounds of general Formula I from the reaction product in the form of the acid addition salts thereof; or optionally converting the free amino compounds of general Formula I, with organic or inorganic acids, into the acid addition salts thereof orliberating the free amino compounds of Formula I fromthe acid addition salts with bases.
  • the compounds according to Formula I can be produced in acid addition salt form by isolating them directly from the reactions conducted in an acidic medium, e.g., nitration, acidic saponification, for example, in the form of the hydrochlorides, acid sulfates, or'neutral sulfates, or by preparing them from the free base by subsequent treatment with an acid.
  • an acidic medium e.g., nitration, acidic saponification
  • Compounds acpounds in concentrated sulfuric acid or acetic anhydride and mixing with concentrated nitric acid or a mixture of concentrated nitric acid and concentrated sulfuric acid. In general, this reaction is conducted at a temperature from C. to +40 C.
  • the acylations are conducted by treating the secondary amino compounds with an acid anhydride, or reacting same in a basic medium, e.g., pyridine, with an acid halogenide.
  • a basic medium e.g., pyridine
  • the saponification of the acylamino group and/or of the acyloxy group is conducted in a conventional manner.
  • the novel compounds possess anti-bacteria activity as well as activity against Trichomonas vaginalis.
  • the minimum inhibitory concentrations (MIC) of several compounds of Formula I against several pathogenic germs are set forth in Table I.
  • the MIC values of the commercially available nitrofurantoin, determined under identical conditions are ethoxy ]-pyrimidine
  • the above-mentioned compounds of this invention can also be detected in the bloodstream. Consequently, these compoundsexhibit a systemic effect, not shown by nitrofurantoin, even in case of model infections, e.g., staphylococci, as shown in Table II.
  • the compounds of this invention can be employed in the treatment of trichomoniasis and in bacterial infections, e.g., staph. infections. They can be administered in forms customarily employed in pharmaceuticals.
  • suitable are tablets, dragees, capsules, pills, suspensions and solutions.
  • Suitable excipients for tablets are, for example, lactose, amylose, talc, gelatin, magnesium stearate, etc.
  • aqueous and oily solutions or suspensions can be employed.
  • the compounds of this invention are formulated so as to provide, for example, 005 0.5 g. of the effective agent in admixture with 0,1 to 5 g. of a pharmacologically indifferent excipient, e.g., a pharmaceutically acceptable carrier, per unit dosage, e.g., per tablet.
  • a pharmacologically indifferent excipient e.g., a pharmaceutically acceptable carrier
  • novel effective agents are usually administered in amountsof between 0.1 and 4.0 g. per patient per day.
  • EXAMPLE 1 a 2-(2-Furyl)-5-(2-methylaminoethoxy)-pyrimidine 5.4 g. of 2-(2-furyl)-5-(2-toluenesulfonyloxyethoxy)-pyrimidine is refluxed for 18 hours in ml. of ethanol and 50 ml. of aqueous methylamine solution (35 percent strength). Then, 25 ml. of methylamine solution is again added, and the refluxing continued for 6 hours. Thereafter, the reaction mixture is concentrated, mixed with water, made alkaline with 2N NaOH, and the product is extracted with ethyl acetate.
  • the mixture is agitated for 1 hour at 0 C. and then for 2 hours at room temperature. Then, the mixture is poured into ice water, neutralized with NaOH, saturated with NaCl, and the product is extracted with ethyl acetate. The ethyl acetate solution is dried, mixed with ethanolic HCl,
  • mice robiologically Active ED (mg/kg.)
  • EXAMPLE 2 a 2-(2-Furyl)-5-(2-n-propylaminoethoxy)-pyrimidine 18.0 g. of 2-(2-furyl)-5-(Z-p-toluenesulfonyloxyethoxy)-pyrimidine and 41 ml. of n-propylamine are refluxed in 200 ml. of ethanol for 30 hours. Then, the mixture is concentrated, mixed with water, made alkaline with 2N NaOH; the product is extracted with ethyl acetate, the ethyl acetate solution is washed, dried, evaporated, and the residue is recrystallized from diisopropyl ether. Yield: 9.3 g., m.p. 74 C.
  • EXAMPLE 5 2-(2-Furyl)-5-[2-(N-acetyl-l-acetoxy- 2-n-butylamino)-ethoxy]-pyrimidine 36.0 g. of 2-(2-furyl)-5-(2-p-toluenesulfonyloxyethoxy)-pyrimidine and 44.5 g. of 2-amino-l-n-butanol are reacted analogously toExample 3(a). The uncrystallized oily crude product (60 g.) is further processed as such. b.
  • EXAMPLE 8 2-( 5-Nitro-2-fury1)-5- 2-( 3 methoxy-n-propylamino ethoxy]-pyrimidine Hydrochloride 4.0 g. of 2-(5-nitro-2-furyl)-5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine is refluxed with 2.7 g. of 3-methoxy-n-propylamine in 20 ml. of dioxane for 6 hours. The mixture is mixed with water, made alkaline with NaOH, and extracted with ethyl acetate. The ethyl acetate solution is dried, evaporated, and the residue (about 4 g.) is chromatographed on g.
  • EXAMPLE 9 a 2-(2-Furyl)-5-[2-(N-acetyl-Z-dimethylaminoethylamino)-ethoxy]-pyrimidine 18.0 g. of 2-(2-furyl)-5-(2-p-toluenesulfonyloxyethoxy)-pyrimidine and 33.0 g. of 2-dimethylaminoethylamine are refluxed in 150 ml. of ethanol for 48 hours. The mixture is then poured into water, made alkaline, taken up in ethyl acetate, and evaporated. The residue is dissolved in 50 ml.
  • EXAMPLE 1 l 2-(2-Furyl)-5-[2-(N-acetyl-2- diethylaminoethylamino)-ethoxy]-pyrimidine
  • the compound is produced analogously to Example 9(a) from 3.6 g. of 2-(2-furyl)-5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 5.8 g. of 2-diethylaminoethylamine.
  • the uncrystallizable crude product (2.9 g.) is further processed as such.
  • b 2-(2-Furyl)-5-[2-(N-acetyl-2- diethylaminoethylamino)-ethoxy]-pyrimidine
  • the compound is produced analogously to Example 9(a) from 3.6 g. of 2-(2-furyl)-5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 5.8 g. of 2-dieth
  • EXAMPLE 12 2-(5-Nitro-2-furyl)-5-[2-(2-diethylaminoethylamino)-ethoxy]-pyrimidine
  • Dihydrochloride 1.9 g. of 2-(5-nitro-2-furyl)-5-[2-(N-acetyl-2- diethylaminoethylamino)-ethoxy]-pyrimidine is refluxed in ml. of 5N l-lCl for l 178 hours. The reaction mixture is completely evaporated under vacuum, and the residue is recrystallized from ethanol. Yield: 0.98 g., m.p. l86187 C. b.
  • EXAMPLE 16 a 2-(2-Fury1)-5-[2-(N-acetyl-n-propylamino)-ethoxy]- pyrimidine
  • This compound is produced analogously to Example 15(a) from 10.8 g. of 2-(2-furyl)-5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 17.7 g. of n-propylamine.
  • the product is recrystallized from ethyl acetate/diisopropyl ether 1:2. Yield: 6.2 g., m.p. 116 C b.
  • EXAMPLE 17 a 2-(2-Furyl)-5-[2-(N-acetyl-isopropylamino)- ethoxy]-pyrimidine
  • This compound is prepared analogously to Example 15(a) from 5.4 g. of 2-(2-furyl)-5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 4.43 g. of isopropylamine.
  • the product is recrystallized from diisopropyl ether. Yield: 2.9 g., m.p. 100 C.
  • EXAMPLE 18 EXAMPLE 10 a. 2-(2-Furyl)-5-[2-(N-acetyl-Z-butylamino)-ethoxy]- pyrimidine 19 This compound is prepared in analogy to Example 15(a) from 3.60 g. of 2-(2-furyl)-5,-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 3.65 g. of 2-butylamine. The product is recrystallized from toluene. Yield: 2.1 g., m.p. 100-101 C. b.
  • EXAMPLE 20 a 2-(2-Furyl)-5-[2-(N-acetyl-cyclopentylamino)- ethoxyI-pyrimidine
  • the compound is prepared analogously to Example 15(a) from 3.6 g. of 2-(2-furyl) 5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 4.25 g. of cyclopentylamine.
  • the product is recrystallized from toluene. Yield: 2.73 g., m.p. ll0-1 1 1 C.
  • EXAMPLE 21 a 2-(2-Furyl)-5-[2-(N-acetyl-cyclohexylamino)- ethoxyl-pyrimidine
  • This compound is produced according to Example 15(a) from 3.6 g. of 2-(2-furyl)-5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 9.9 g. of cyclohexylamine.
  • the product is recrystallized from toluene. Yield: 2.1 g., m.p. 136137 C.
  • EXAMPLE 22 b 2-(2-Furyl)-5-[2-(N-acetyl-2-methoxyethylamino)- ethoxyl-pyrimidine
  • This compound is prepared analogously to Example 15(a) from 27.0 g. of 2-(2-furyl)-5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 28.2 g. of 2-methoxyethylamine.
  • the product is recrystallized from diisopropyl ether/tetrahydrofuran. 2:1. Yield: 15.2 g., m.p. 113 C.
  • b 2-(2-Furyl)-5-[2-(N-acetyl-2-methoxyethylamino)- ethoxyl-pyrimidine
  • EXAMPLE 23 a 2-(2-Furyl)-5-[2-(N-acetyl-benzylamino)-ethoxy]- pyrimidine
  • This compound is prepared analogously to Example 15(a) from 2.52 g. of 2-(2-furyl)-5-(2-ptoluenesulfonyloxyethoxy)-pyrimidine and 3.75 g. of benzylamine.
  • the product is further processed as the crude product. Yield: 1.30 g., m.p. 107-109 C.
  • EXAMPLE 24 a 2-(2-Furyl)-5-(N-formyl-2-n-propylaminoethoxy)- pyrimidine 2.47 g. of 2-(2-furyl)-5-(2-n-propylaminoethoxy)- pyrimidine is dissolved in 20 ml. of formic acid and 6 ml. of acetic anhydride and allowed to stand overnight. The reaction mixture is completely evaporated under vacuum, and the residue is recrystallized from diisopropyl ether. Yield: 1.70 g., m.p. 98 C.
  • EXAMPLE 25 a 2-(2-Furyl)-5-[2-(N-n-butyryl-n-propylamino)- ethoxy]-pyrimidine 1.20 g. of 2-(2-furyl)-5-(2-n-propylaminoethoxy)- pyrimidine is dissolved in 20 ml. of pyridine; 0.51 ml. of n-butyryl chloride is added and the mixture is agitated at room temperature for 1 hour, then poured into water, acidified with hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate solution is dried, concentrated, and recrystallized from ethanol.
  • EXAMPLE 29 a 2-(2-Furyl)-5-[2-(2-hydroxypropylamino)-ethoxy]- pyrimidine 18.2 g. of 2-(2-furyl)-5-(2-p-toluenesulfonyloxyethoxy)-pyrimidine is refluxed with 18.8 g. of 2- hydroxypropylamine in 200 ml. of ethanol for hours. The mixture is concentrated, mixed with .water and 1N NaOH, extracted with ethyl acetate, and the ethyl acetate solution is evaporated. The residue is recrystallized from diisopropyl ether. Yield: 9.3 g., m.p. 100 C. b.
  • EXAMPLE 31 a 2-(2-Furyl)-5-[2-(2,3-dihydroxypropylamino)- ethoxy]-pyrimidine 51.0 g. of 2-(2-furyl)-5-(2-p-toluenesulfonyloxyethoxy)-pyrimidine is refluxed with 77.9 g. of l-amino- 2,3-propanediol in 500 ml. of ethanol for 7 hours. The mixture is concentrated, mixed with water and NaOH, and extracted with ethyl acetate. The ethyl acetate solution is evaporated and the residue chromatographed on 300 g.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-[2- -acetyll acemy: ir butyi am'm'a enian 7 pyrimidine.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-[2- (N-acetyl-Z-diethylaminoethylamino)-ethoxy]- pyrimidine.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-[2- (N-acetyl-Z-butylamino)-ethoxyl-pyrimidine.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-[2- (N-acetyl-cyclopentylamino)-ethoxy]-pyrimidine.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-[2- (N-acetyl-cyclohexylamino )-ethoxy]-pyrimidine.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-[2- (N-acetyl-benzylamino)-ethoxy]-pyrimidine.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-(nformyl-2-n-propylaminoethoxy)-pyrimidine.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-[2- (N-n-butyrl-n-ropylamino)-ethoxy]-pyrimidine.
  • a compound of claim 1 2-(5-nitro-2-furyl)-5-[2- (N-acetyl-2,3-diacetoxy-propylamino)-ethoxy]- pyrimidine.

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  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US00235426A 1971-03-17 1972-03-16 Nitrofurylpyrimidines Expired - Lifetime US3846428A (en)

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Publication number Priority date Publication date Assignee Title
US3707485A (en) * 1969-07-19 1972-12-26 Schering Ag 2-(5-nitro-furyl-2)-5-aminoethoxy pyrimidines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3707485A (en) * 1969-07-19 1972-12-26 Schering Ag 2-(5-nitro-furyl-2)-5-aminoethoxy pyrimidines

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AU463550B2 (en) 1975-07-14
ZA721689B (en) 1972-12-27
CA945557A (en) 1974-04-16
BE780879A (fr) 1972-09-18
FR2130327A1 (forum.php) 1972-11-03
DE2113529A1 (de) 1972-12-14
HU163178B (forum.php) 1973-06-28
AT312589B (de) 1974-01-10
DD96950A5 (forum.php) 1973-04-12
IL38962A (en) 1975-10-15
AU3976972A (en) 1973-09-13
DE2113529B2 (de) 1979-08-02
SU458130A3 (ru) 1975-01-25
IL38962A0 (en) 1972-05-30
DK126999B (da) 1973-09-10
PL83278B1 (forum.php) 1975-12-31
ES400560A1 (es) 1975-02-01
CH575943A5 (forum.php) 1976-05-31
GB1391933A (en) 1975-04-23
DE2113529C3 (de) 1980-04-30
FR2130327B1 (forum.php) 1975-04-25

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