US3560504A - Virostatically effective substituted 3-alkenyl-5-ethyl uracil compounds - Google Patents

Virostatically effective substituted 3-alkenyl-5-ethyl uracil compounds Download PDF

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US3560504A
US3560504A US757146A US3560504DA US3560504A US 3560504 A US3560504 A US 3560504A US 757146 A US757146 A US 757146A US 3560504D A US3560504D A US 3560504DA US 3560504 A US3560504 A US 3560504A
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ethyl
uracil
allyl
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chloro
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Kaliash Kumar Gauri
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Robugen GmbH
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    • 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

Definitions

  • Examples of such compounds are 1,5-diethyl-3-allyl-4-chloro uracil, 1-methyl-3-allyl or crotyl-4-chloro-5-ethyl uracils, 1- methyl or ethyl-3-allyl or crotyl-S-ethyl uracils. They are preferably obtained by alkenylation in 3-position of the corresponding S-ethyl uracil compounds which have in 3-position hydrogen. They are preferably topically applied to the virus-affected areas of the body in the form of solutions, ointments, powders, sprays, or the like which contain between about 0.5% and about 50% thereof.
  • the present invention relates to new and valuable uracil compounds and more particularly to virostatically effective S-ethyl uracil compounds, to a process of their manufacture, to pharmaceutical compositions containing same, and to a method of using same in the therapy of virus infections.
  • Another object of the present invention is to provide a simple and effective process of producing such substituted S-ethyl uracil compounds.
  • a further object of the present invention is to provide virostatically effective compositions containing such substituted S-ethyl uracil compounds as active ingredients.
  • Still another object of the present invention is to provide a method of treating patients affected by virus infections with such disubstituted S-ethyl uracil compounds.
  • R indicates straight chain or branched alkyl with 1 to 4 carbon atoms, preferably methyl or ethyl, cycloalkyl, aryl, or aralkyl, which alkyl, aryl, or aralkyl may be substituted;
  • R indicates straight chain or branched alkenyl with 3 to 6 carbon atoms, preferably allyl or crotyl
  • X indicates hydrogen or halogen, preferably chlorine.
  • a preferred process of producing such compounds comprises reacting S-ethyl uracil compounds of Formula II 0 II o wherein R and X represent the same substituents as indicated above, with an alkenyl halogenide, such as al1ylbromide, in the presence of a basic agent capable of binding acids, for instance, potassium carbonate, in a suitable solvent or solvent mixture or even without solvent whereby the alkenyl halogenide serves as solvent.
  • an alkenyl halogenide such as al1ylbromide
  • Example 1 20.3 g. of 1,5-diethyl-4-chloro uracil are heated under reflux with 36.3 g. of allylbromide and 16.6 g. of freshly calcined potassium carbonate in 120 cc. of dried acetone and cc. of dried dimethylformamide for 2.4 hours. Care is taken that moisture is excluded during the reaction. After cooling, the reaction mixture is filtered to remove solid matter. The mixture of solvents and excess allylbromide is distilled off in a vacuum and the residue is subjected to fractional distillation in a vacuum. The resulting 1,5-diethyl-3-allyl-4-chloro uracil has a boiling point of -120" C./O.1 mm.
  • Example 10.0 g. of 1-methyl-3-crotyl-4-chloro-S-ethyl uracil are incorporated into an ointment base consisting of 3.0 g. of cetyl alcohol, 5.0 g. of anhydroud lanolin, and 82.0 g.
  • equimolecu- 20 lar amounts for instance, of isopropyl-4-chloro-5-ethyl uracil, 1-n-butyl-4-bromo-5-ethyl uracil, 1-phenyl-4-iodo- S-ethyl uracil, 1-p-tolyl-4-chloro-S-ethyl uracil, l-benzyl- 4-chloro-5-ethyl uracil, 4-chloro-5-ethyl uracil, l-cyclohexyl-4-chloro-5-ethyl uracil, and the like compounds while otherwise the procedure is the same as described hereinabove.
  • the new substituted S-ethyl uracil compounds are topically applied to the Virus-infected areas of the body in the form of solutions, emulsions, creams, ointments, powders, sprays, and the like preparations.
  • the amount of the active agent in such pharmaceutical preparations may vary. Amounts between 0.5% and and even more may be admixed to the pharmaceutical excipients, ointment bases, solvents, and the like.
  • Preferred amounts of the virostatically active agent in such preparations are amounts between about 1.0% and 10.0%.
  • Example 6 10.0 g. of 1,5-diethyl-3-allyl-4-chloro uracil are dissolved in 10.0 g. of propylene glycol and 80 g. of 50% ethanol. The resulting solution is repeatedly applied to the virus aiTected area of the skin or to the lips.
  • Example 7 50.0 g. of 1,S-diethyl-3-allyl-4-chloro uracil are dissolved in 50.0 g. of dimethylsulfoxide. The resulting solution is repeatedly applied to the virus-affected areas of the body.
  • Example 8 1.0 g. of 1,5-diethyl-3-allyl-4-chloro uracil is dissolved in 3.0 g. of the polyoxy ethylene ester of castor oil sold under the trademark ORPE by Fabenfabriken Bayer of Opladen, Germany, and 96 g. of physiological (0.9%) sodium chloride solution is added. The resulting mixture is applied to the virus affected parts of the body.
  • Example 9 0.5 g. of 1-methyl-3-allyl-4-chloro-5-ethyl uracil is dissolved in 99.5 g. of the liquid saturated fatty alcohol mixture consisting mainly of 2-octyl dodecanol and sold under the trademark Eutanol G by Deutsche Hydrierwerke G.m.b.H. of Duesseldorf, Germany.
  • EXAMPLE 12 1.0 g. of l-methyl-crotlyl-S-ethyl uracil are mixed with 5 .0 g. of ethanol and enclosed into a spray container with 94.0 g. of a propellant such as trichlorofluoro methane. The resulting preparation is applied by spraying to virusaffected parts of the body.
  • Example 13 5 g. of 1,5-diethyl3-allyl-4-chloro uracil and 5 g. of a non-ionogenic emulsifier sold under the trademark Cremophor EL by Badische Anilin- & Soda-Fabrik of Ludwigshafen, Germany, which is a condensation prodnet of ethylene oxide with castor oil, are intimately mixed with cc. of physiological (0.9%) sodium chloride solution. The resulting mixture is repeatedly applied to the virus-affected parts of the body.
  • Cremophor EL by Badische Anilin- & Soda-Fabrik of Ludwigshafen, Germany
  • Example 14 2 g. of 1,S-diethyl-3-allyl-4-chloro uracil are emulsified with 2 g. of Tween 60 sold by Atlas Powder Company of Wilmington and being a polyoxyethylene sorbitan mono-stearate, 6 g. of Arlacel 60, sold by Atlas Powder Company of Wilmington, Del., and being a sorbitan mono-stearate, 10 g. of stearic acid, and 4 g. of Witocan H, sold by Chemische Werke Witten G.m.b.H. of Witten (Ruhr), Germany, which is a mixture of fatcontaining saturated fatty acids with 12 to 18 carbon atoms, in 76 cc. of distilled water. The resulting composition has proved of value in the treatment of virus infections.
  • Tween 60 sold by Atlas Powder Company of Wilmington and being a polyoxyethylene sorbitan mono-stearate
  • 6 g. of Arlacel 60 sold by Atlas Powder Company of Wilmington, Del.
  • Witocan H
  • Example 15 10 g. of 1,S-diethyl-3-allyl-4-chloro uracil are incorporated into an ointment of 10' g. petrolatum (Vaseline), 40 g. of anhydrous lanolin, 7 g. of liquid petrolatum (liquid parafiin), and 33 cc. of water. The resulting ointment is useful for topical application.
  • petrolatum Vaseline
  • 40 g. of anhydrous lanolin 7 g. of liquid petrolatum (liquid parafiin)
  • 33 cc. of water 33 cc.
  • compositions may be prepared with other solvents, ointment bases, excipients, and the like.
  • composition containing the above mentioned substituted S-ethyl uracil compounds according to the present invention are useful for topical application to the virus-affected parts of the human body. They may be applied not only to the skin of the patient but also to mucous membranes, such as the mucous membranes of the mouth and of the genital organs.
  • UTILITY The virostatic activity of the substituted S-ethyl uracil compounds according to the present invention has been demonstrated in vitro in tissue cultures and in vivo on the rabbits eye according to the method of Kaufman et al. Arch. Ophthalm., vol. 67 (1962), page 583. These tests have shown that said compounds are highly effective against DNA-viruses such as herpes, vaccinia, varicella virus as well as against RNA-viruses, such as foot-andmouth-disease, Sindbis virus and others.
  • DNA-viruses such as herpes, vaccinia, varicella virus
  • RNA-viruses such as foot-andmouth-disease, Sindbis virus and others.
  • the preparations of these examples were applied externally by means of a swab stick to the respective parts of the body in the beginning of the treatment five times daily and later once to five times daily for a total period of from one day to five days. It may be mentioned that only patients who were suffering for more than three years from such herpes infections were treated with the preparations according to the present invention.
  • Treatment with the preparations according to the present invention has the advantage that the herpes blisters, for instance, of Herpes simplex became disiccated and healed within one to five days while without such a treatment healing required eight to ten days. It is to be assumed that irritation is not caused by the compounds of this invention but by the solvent dimethyl sulfoxide, especially since dimethyl sulfoxide applied without medicament to fresh Herpes blisters causes a burning sensation.
  • R is a member selected from the group consisting of alkyl with 1 to 4 carbon atoms, cyclohexyl, phenyl, tolyl, and benzyl;
  • R is a member selected from the group consisting of allyl and crotyl
  • X is a member selected from the group consisting of hydrogen and halogen. 21.
  • R is a member selected from the group consisting of allyl and crotyl
  • X is a member selected from the group consisting of hydrogen and halogen. 3.
  • X is chlorine.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

HIGHLY EFFECTIVE VIROSTATIC AGENTS ARE SUBSTITUTED 5-ETHYL URACIL COMPOUNDS WHICH HAVE ALKENYL WITH 3 TO 6 CARBON ATOMS IN 3-POSITION AND MAY BE SUBSTITUTED IN 1POSITION BY ALKYL WITH 1 TO 4 CARBON ATOMS, CYCLOALKYL, ARYL, OR ARALKYL AND IN 4-POSITION BY HALOGEN. EXAMPLES OF SUCH COMPOUNDS ARE 1,5-DIETHYL-3-ALLYL-4-CHLORO URACIL, 1-METHYL-3-ALLYL OR CROTYL-4-CHLORO-5-ETHYL URACILS, 1METHYL OR ETHYL-3-ALLYL OR CROTYL-5-ETHYL URACILS. THEY ARE PREFERABLY OBTAINED BY ALKENYLATION IN 3-POSITION OF THE CORRESPONDING 5-ETHYL URACIL COMPOUNDS WHICH HAVE IN 3-POSITION HYDROGEN. THEY ARE PREFERABLY TOPICALLY APPLIED TO THE VIRUS-AFFECTED AREAS OF THE BODY IN THE FORM OF SOLUTIONS, OINTMENTS, POWDERS, SPRAYS, OR THE LIKE WHICH CONTAIN BETWEEN ABOUT 0.5% AND ABOUT 50% THEREOF.

Description

United States Patent Otfice Patented Feb. 2, 1971 US. Cl. 260-260 12 Claims ABSTRACT OF THE DISCLOSURE Highly effective virostatic agents are substituted S-ethyl uracil compounds which have alkenyl with 3 to 6 carbon atoms in 3-position and may be substituted in 1- position by alkyl with 1 to 4 carbon atoms, cycloalkyl, aryl, or aralkyl and in 4-position by halogen. Examples of such compounds are 1,5-diethyl-3-allyl-4-chloro uracil, 1-methyl-3-allyl or crotyl-4-chloro-5-ethyl uracils, 1- methyl or ethyl-3-allyl or crotyl-S-ethyl uracils. They are preferably obtained by alkenylation in 3-position of the corresponding S-ethyl uracil compounds which have in 3-position hydrogen. They are preferably topically applied to the virus-affected areas of the body in the form of solutions, ointments, powders, sprays, or the like which contain between about 0.5% and about 50% thereof.
BACKGROUND OF THE INVENTION 1) Field of the invention The present invention relates to new and valuable uracil compounds and more particularly to virostatically effective S-ethyl uracil compounds, to a process of their manufacture, to pharmaceutical compositions containing same, and to a method of using same in the therapy of virus infections.
(2) Description of the prior art -alkyl substituted uracil compounds are known (M. Muraoka, A. Takada, and T. Ueda Keio J. Med., vol. 11 (1962) page 95; see Chem. Abstracts, vol. 57 (1962), page 171921)). These compounds were found to be virostatically ineffective. 1,5-disubstituted uracil compounds have also no virostatic activity.
SUMMARY OF THE INVENTION It is one object of the present invention to provide highly virostatically effective compounds of the uracil group which are characterized by being substituted in 3- position or, respectively, in 3-, and 4-position and may be substituted in l-position and which have ethyl in 5- position.
Another object of the present invention is to provide a simple and effective process of producing such substituted S-ethyl uracil compounds.
A further object of the present invention is to provide virostatically effective compositions containing such substituted S-ethyl uracil compounds as active ingredients.
Still another object of the present invention is to provide a method of treating patients affected by virus infections with such disubstituted S-ethyl uracil compounds.
Other objects of the present invention and advantageous features thereof will become apparent as the description proceeds.
In principle the virostatically effective S-ethyl uracil compounds according to the present invention are compounds of the following Formula I:
o=o CX R2 (1) In said formula R indicates straight chain or branched alkyl with 1 to 4 carbon atoms, preferably methyl or ethyl, cycloalkyl, aryl, or aralkyl, which alkyl, aryl, or aralkyl may be substituted;
R indicates straight chain or branched alkenyl with 3 to 6 carbon atoms, preferably allyl or crotyl; and
X indicates hydrogen or halogen, preferably chlorine.
A preferred process of producing such compounds comprises reacting S-ethyl uracil compounds of Formula II 0 II o wherein R and X represent the same substituents as indicated above, with an alkenyl halogenide, such as al1ylbromide, in the presence of a basic agent capable of binding acids, for instance, potassium carbonate, in a suitable solvent or solvent mixture or even without solvent whereby the alkenyl halogenide serves as solvent.
phenyl alanine. In addition thereto they are of surprisingly low toxicity.
DESCRIPTION OF THE PREFERRED EMBODIMENTS The following examples serve to illustrate the present invention without, however, limiting the same thereto.
Example 1 20.3 g. of 1,5-diethyl-4-chloro uracil are heated under reflux with 36.3 g. of allylbromide and 16.6 g. of freshly calcined potassium carbonate in 120 cc. of dried acetone and cc. of dried dimethylformamide for 2.4 hours. Care is taken that moisture is excluded during the reaction. After cooling, the reaction mixture is filtered to remove solid matter. The mixture of solvents and excess allylbromide is distilled off in a vacuum and the residue is subjected to fractional distillation in a vacuum. The resulting 1,5-diethyl-3-allyl-4-chloro uracil has a boiling point of -120" C./O.1 mm. Hg, refractive index 4 Example 10.0 g. of 1-methyl-3-crotyl-4-chloro-S-ethyl uracil are incorporated into an ointment base consisting of 3.0 g. of cetyl alcohol, 5.0 g. of anhydroud lanolin, and 82.0 g.
5 of white petrolatum. The resulting ointment is applied to the virus-affected parts of the body.
TABLE I Analysis, percent Boiling point Calculated Found Empirical Molecular Example No. R1 R2 X C. mm. Hg formula weight C H N C H N CHZCH=OH2 01 140-141 0.3 CmHraClNzOz 228.69 62.52 5.73 12. 52.57 6.69 12.22 CH2CH=CHCH 01 145447 0.4 CnHrsClNzOz 242.70 54.44 6.23 11. 54 54. 42 6.30 11.54 CH20H=GH H 138 0.3 C11H15N2O2 208.26 63.43 7.74 13. 63.38 7.78 13.49 CzH5 CHz-CH=CHCH H 150-152 0.2 CrzHrsNzOz 222.29 64.84 8.16 12.60 64. 78 8.24 12.59
In place of the starting uracil compounds used in the Example 11 preceding examples, there may be employed equimolecu- 20 lar amounts, for instance, of isopropyl-4-chloro-5-ethyl uracil, 1-n-butyl-4-bromo-5-ethyl uracil, 1-phenyl-4-iodo- S-ethyl uracil, 1-p-tolyl-4-chloro-S-ethyl uracil, l-benzyl- 4-chloro-5-ethyl uracil, 4-chloro-5-ethyl uracil, l-cyclohexyl-4-chloro-5-ethyl uracil, and the like compounds while otherwise the procedure is the same as described hereinabove.
In place of the alkenyl halogenides used as the other reaction component in the preceding examples, there may be employed equimolecular amounts, for instance, of 1-chloro-2-pentene, l-bromo-Z-hexene, 1-chl0ro-3-methyl-2-butene, 1=bromo-2,3-dimethyl-2-butene, 1-chloro-3- butene, and the like compounds while otherwise the procedure is the same as indicated above.
As stated hereinabove, the new substituted S-ethyl uracil compounds are topically applied to the Virus-infected areas of the body in the form of solutions, emulsions, creams, ointments, powders, sprays, and the like preparations. The amount of the active agent in such pharmaceutical preparations may vary. Amounts between 0.5% and and even more may be admixed to the pharmaceutical excipients, ointment bases, solvents, and the like. Preferred amounts of the virostatically active agent in such preparations are amounts between about 1.0% and 10.0%.
The following examples serve to illustrate the preparation of suitable pharmaceutical preparations according to the present invention without, however, being limited thereto.
Example 6 10.0 g. of 1,5-diethyl-3-allyl-4-chloro uracil are dissolved in 10.0 g. of propylene glycol and 80 g. of 50% ethanol. The resulting solution is repeatedly applied to the virus aiTected area of the skin or to the lips.
Example 7 50.0 g. of 1,S-diethyl-3-allyl-4-chloro uracil are dissolved in 50.0 g. of dimethylsulfoxide. The resulting solution is repeatedly applied to the virus-affected areas of the body.
Example 8 1.0 g. of 1,5-diethyl-3-allyl-4-chloro uracil is dissolved in 3.0 g. of the polyoxy ethylene ester of castor oil sold under the trademark ORPE by Fabenfabriken Bayer of Opladen, Germany, and 96 g. of physiological (0.9%) sodium chloride solution is added. The resulting mixture is applied to the virus affected parts of the body.
Example 9 0.5 g. of 1-methyl-3-allyl-4-chloro-5-ethyl uracil is dissolved in 99.5 g. of the liquid saturated fatty alcohol mixture consisting mainly of 2-octyl dodecanol and sold under the trademark Eutanol G by Deutsche Hydrierwerke G.m.b.H. of Duesseldorf, Germany.
5.0 g. of 1-methyl-3-allyl-5-ethyl uracil are intimately mixed with 10.0 g. of glycine, 10.0 g. of lactose, and g. of finely divided silicic acid sold under the trademark Aerosil are intimately mixed with each other to yield a virostatically eflective powder.
EXAMPLE 12 1.0 g. of l-methyl-crotlyl-S-ethyl uracil are mixed with 5 .0 g. of ethanol and enclosed into a spray container with 94.0 g. of a propellant such as trichlorofluoro methane. The resulting preparation is applied by spraying to virusaffected parts of the body.
Example 13 5 g. of 1,5-diethyl3-allyl-4-chloro uracil and 5 g. of a non-ionogenic emulsifier sold under the trademark Cremophor EL by Badische Anilin- & Soda-Fabrik of Ludwigshafen, Germany, which is a condensation prodnet of ethylene oxide with castor oil, are intimately mixed with cc. of physiological (0.9%) sodium chloride solution. The resulting mixture is repeatedly applied to the virus-affected parts of the body.
Example 14 2 g. of 1,S-diethyl-3-allyl-4-chloro uracil are emulsified with 2 g. of Tween 60 sold by Atlas Powder Company of Wilmington and being a polyoxyethylene sorbitan mono-stearate, 6 g. of Arlacel 60, sold by Atlas Powder Company of Wilmington, Del., and being a sorbitan mono-stearate, 10 g. of stearic acid, and 4 g. of Witocan H, sold by Chemische Werke Witten G.m.b.H. of Witten (Ruhr), Germany, which is a mixture of fatcontaining saturated fatty acids with 12 to 18 carbon atoms, in 76 cc. of distilled water. The resulting composition has proved of value in the treatment of virus infections.
Example 15 10 g. of 1,S-diethyl-3-allyl-4-chloro uracil are incorporated into an ointment of 10' g. petrolatum (Vaseline), 40 g. of anhydrous lanolin, 7 g. of liquid petrolatum (liquid parafiin), and 33 cc. of water. The resulting ointment is useful for topical application.
Of course, other solutions, lotions, ointments, powders, sprays, and the like compositions may be prepared with other solvents, ointment bases, excipients, and the like.
The composition containing the above mentioned substituted S-ethyl uracil compounds according to the present invention are useful for topical application to the virus-affected parts of the human body. They may be applied not only to the skin of the patient but also to mucous membranes, such as the mucous membranes of the mouth and of the genital organs.
UTILITY The virostatic activity of the substituted S-ethyl uracil compounds according to the present invention has been demonstrated in vitro in tissue cultures and in vivo on the rabbits eye according to the method of Kaufman et al. Arch. Ophthalm., vol. 67 (1962), page 583. These tests have shown that said compounds are highly effective against DNA-viruses such as herpes, vaccinia, varicella virus as well as against RNA-viruses, such as foot-andmouth-disease, Sindbis virus and others.
Clinical tests have been carried out especially with 1,5-diethyl-3-allyl-4-chloro uracil which was used in herpes diseases of the skin and the mucosa. The following Table II shows the results achieved by a treatment:
(a) with the composition according to Example 6, (b) with the composition according to Example 7, and (c) with the composition according to Example 8.
The preparations of these examples were applied externally by means of a swab stick to the respective parts of the body in the beginning of the treatment five times daily and later once to five times daily for a total period of from one day to five days. It may be mentioned that only patients who were suffering for more than three years from such herpes infections were treated with the preparations according to the present invention.
TABLE II Patients Complete Improve- Irrita- Ex. Virus infection treated cure ment tion 6- Herpes labialis. 8 6 2 Herpes solemn. 1 1 0 Herpes labialis 5 2 2 1 7 Herpes simplex 6 3 1 2 7 Herpes genitalia" 2 2 0 0 7.. Stomatitis aphthosau 2 1 1 0 8 Herpes labialt's 8 6 2 0 Herpes simplex- 3 2 1 0 8 herpes genitalia. l 1 0 0 8 Stomatt'tt's aphthosan 2 0 2 0 Total 38 23 12 3 The rate of complete cure in these preliminary clinical tests thus is at least 60%. Treatment with the preparations according to the present invention has the advantage that the herpes blisters, for instance, of Herpes simplex became disiccated and healed within one to five days while without such a treatment healing required eight to ten days. It is to be assumed that irritation is not caused by the compounds of this invention but by the solvent dimethyl sulfoxide, especially since dimethyl sulfoxide applied without medicament to fresh Herpes blisters causes a burning sensation.
Of course, many changes and variations in the starting materials, unsaturated halogenides, and basic acid-burning agents used, in the reaction conditions, temperature, and duration, in the preparation and composition of pharmaceutical preparations containing the substituted S-ethyl uracil compounds of the present invention, in the mode of administration and the amounts administered and the like may be made by those skilled in this art in accordance with the principles set forth herein and in the claimed annexed hereto.
I claim:
1. A substituted S-ethyl uracil compound of the formula:
wherein R is a member selected from the group consisting of alkyl with 1 to 4 carbon atoms, cyclohexyl, phenyl, tolyl, and benzyl;
R is a member selected from the group consisting of allyl and crotyl; and
X is a member selected from the group consisting of hydrogen and halogen. 21. A substituted S-ethyl uracil compound of the formu a:
methyl and ethyl; R is a member selected from the group consisting of allyl and crotyl; and X is a member selected from the group consisting of hydrogen and halogen. 3. The compound as defined in claim 1, wherein X is chlorine.
4. The compound as defined in claim 1, wherein R is methyl.
5. The compound as defined in claim 1, wherein R is ethyl.
6. The compound as defined in claim 1, wherein R is allyl.
7. The compound as defined in claim 1, wherein R is crotyl.
8. The compound as defined in claim 1, wherein R is ethyl, R is allyl, and X is chlorine, said compound being 1,5-diethyl-3-allyl-4-chloro uracil.
9. The compound as defined in claim 1, wherein R is methyl, R is allyl, and X is chlorine, said compound being 1-methyl-3-allyl-4-chloro-5-ethyl-uracil.
10. The compound as defined in claim 1, wherein R is methyl, R is crotyl, and X is chlorine, said compound being 1-methyl-3-crotyl-4-chloro-5-ethyl uracil.
11. The compound as defined in claim 1, wherein R is ethyl, R is allyl, and X is hydrogen, said compound being 1,5-diethyl-3-allyl uracil.
12. The compound as defined in claim 1, wherein R is ethyl, R is crotyl, and X is hydrogen, said compound being 1,5-diethyl-3-crotyl uracil.
References Cited UNITED STATES PATENTS 2/1966 Luckenbaugh et al. 260-260 7/1967 Luckenbaugh 260-260 US. Cl. X.R. 424-251
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5914399A (en) * 1997-10-22 1999-06-22 Sumika Fine Chemicals Co., Ltd. Method for producing 5-isopropyluracil

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5914399A (en) * 1997-10-22 1999-06-22 Sumika Fine Chemicals Co., Ltd. Method for producing 5-isopropyluracil

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