US3020277A - 1-(2-n-propyl-4-amino-5-pyrimidyl-methyl)-2(or 4)-methyl pyridinium salts - Google Patents

1-(2-n-propyl-4-amino-5-pyrimidyl-methyl)-2(or 4)-methyl pyridinium salts Download PDF

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Publication number
US3020277A
US3020277A US829979A US82997959A US3020277A US 3020277 A US3020277 A US 3020277A US 829979 A US829979 A US 829979A US 82997959 A US82997959 A US 82997959A US 3020277 A US3020277 A US 3020277A
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Prior art keywords
amino
methyl
propyl
pyrimidylmethyl
pyridinium
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US829979A
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English (en)
Inventor
Edward F Rogers
Lewis H Sarett
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Merck and Co Inc
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Merck and Co Inc
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Priority to BE587330D priority Critical patent/BE587330A/xx
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Priority to US829979A priority patent/US3020277A/en
Priority to GB3698/60A priority patent/GB911551A/en
Priority to DEM44190A priority patent/DE1149010B/de
Priority to CH163960A priority patent/CH381694A/de
Priority to FI0327/60A priority patent/FI43598B/fi
Priority to FR820636A priority patent/FR1291531A/fr
Priority to SE2942/60A priority patent/SE308105B/xx
Priority to ES0257622A priority patent/ES257622A1/es
Priority to US38449A priority patent/US3020200A/en
Priority to US38451A priority patent/US3065132A/en
Application granted granted Critical
Publication of US3020277A publication Critical patent/US3020277A/en
Priority to SE7084/63A priority patent/SE311801B/xx
Priority to OA51542A priority patent/OA02621A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Definitions

  • This invention relates generally to new chemical coutpounds. More specifically, it is concerned with chemical compounds which are useful in the prevention and the cure of. coccidiosis. Still more particularly, it is concerned with a series of new pyridinium quaternary salts which are efiective in controlling coccidiosis when fed in small amounts to poultry. Still more specifically, it relates to 1 (2 loweralkyl 4 amino pyrimidylmethyl)-lowera.lkyl-pyridinium quaternary salts where the lower alkyl radical in the pyrimidine ring contains at least two carbons, and with methods for preparing such compounds. It is further concerned with novel compositions containing such substances.
  • Coccidiosis is a common and widespread poultry disease caused by' several species of protozoan parasites of the genus Eimeria, such as E. tenella, E. necatrix, E.
  • E. tenella is the causative agent of a severe and often fatal infection of the ceca of chickens which is manifested by extensive hemorrhage, accumulation of blood in the ceca, and the passage of blood in the droppings.
  • E. necatrix as well as certain other species attack the small intestine of the chick causing what is known as intestinal coccidiosis.
  • Related species of coccidia such as E. melagridis and E. adenoides are causative organisms of coccidioss in turkeys. When left untreated, the severe forms of coccidiosis lead to poor weight gain, reduced feed efficiency and high mortality in fowl. The elimination or control of coccidiosis is. therefore, of paramount importance in the poultry raising industry.
  • l (2 lon-eralkyl 4 amino 5 pyrimidylmethyl) loweralkyl-pyridinium quaternary salts wherein the pyridine ring is substituted with from one to three lower alkyl groups and the lower alkyl radical at the 2-position of the pyrimidine ring contains at least two carbon atoms, are very effective in preventing and treating coccidiosis.
  • the preferred compounds of our invention are quaternary salts of the formula ESQ-cures in) wherein R is a lower alkyl radical containing at least two carbon atoms, R is a lower alkyl radical, n has a value of l, 2 or 3, and X is an anion; b and c are posttive numbers having values such that the positive charge of 1) moles of cation is neutralized by c moles of anion X.
  • X is a monovending anion such as a halide
  • b is l and c is 2.
  • snore than one lower alkyl group is present in the pyridine ring. i.e. when n is 2 or 3, such lower alkyl groups may be the same or different.
  • these compounds are prepared by reaction of a 2-loweralkyl-4-amino-5- substituted methyl pyrimidine with an appropriately alkylated pyridine.
  • the compounds described herein may be considered as substituted pyridines.
  • the pyridine ring is substituted at the l-position by a 2-loweralkyl-4-amino- 5-pyrirnidylmethyl radical; it is further substituted with one or more lower alkyl groups, such as methyl, Cthylv propyl, isopropyl, butyl and amyl groups, such substituents being in at least one of the 2, 3 and/or 4 positions of the ring.
  • the pyrimidine moiety also contains a lower alkyl group at the 2-position of the pyrimidine ring.
  • which group is one containing at least two carbon atoms, e.g. ethyl, propyl, isopropyl, isobutyl and the like.
  • the lower alkyl groups present in the pyrimidine and pyridine portions of these salts need not, of course, be the same in any particular compound.
  • the compounds of the invention are active generally against coccidiosis, certain of the quaternary salts are particularly advantageous in that they possess a broader anticoccidial spectrum, i.e. are active at low levels against more of the most troublesome strains of coccidia, than others, and in that they exhibit minimal undesirable side eifects.
  • the preferred compounds are the 1- (2 ethyl or 2 propyl 4 amino 5 py rimidylmethyl)-loweralkyl pyridinium quaternary salts having a lower alkyl radical at either the 2 or 4 position of the pyridine ring.
  • l-(2- ethyl 4 amino 5 pyrimidylmethyl) 2 methyl pyridinium salts 1 (2 ethyl 4 amino -5 pyrimidyl- 7 methyl)-4-methyl pyridinium salts, l-(2-propyl-4-amino- S-pyrimidylmethyl)-2-methyl pyridinlum salts, and l-(2 propylA-amino-S-pyrimidylmethyl)-4-mcthyl pyridinium salts, which substances exhibit a very favorable spectrum of anticoccidial activity and therapeutic index.
  • 1-(2- butyl 4 amino 5 pyrimidylmethyl) 2 methylpyridinium salts are likewise preferred since they are particularly effective against E. acervulina.
  • the anion of the quaternary compound may be an inorganic anion such as chloride, bromide, iodide, nitrate, sulfate, phosphate and the like, or the anion of an organic acid such as citric, tartaric, acetic, picric, stearic, succinic, benzoic, phthalic, phenoxyacetic, embonic, abietic. Z-naphthalene sulfonic or ethylencdiamine tctracctic acids. It may also be the anion of a polymer such as a polyphosphate or polystyrenesultonate ion.
  • anion is not critical and any anion may be employed as long at it is not unduly toxic for poultry when the compounds of the invention are employed as coccidiostats. It will be realized by those skilled in this art that an acid addition salt of the primary amino group present in these compounds will also be formed concurrently with the quaternary salt.
  • the compounds of this invention are synthesized by reacting together an appropriately substituted pyrimidine and a lower alkylated pyridine.
  • a pyrimidine reactant we may employ an ester of a S-hydroxymethyl pyrimidine and a strong inorganic acid such as a hydrohalic acid.
  • a 2-loweralkyl-4-amino-S-halomethyl pyrimidine dihydrohalide in which the halogen is bromine or chlorine and the lowcralkyl radical contains at least two carbon atoms, is reacted directly with the alkylated pyridine.
  • esters of the 2-loweralkyl-4-amino5-hydroxymethyl pyrimidine such as the nitrate ester.
  • suitable esters are those of organic sulfinic and sulfonic acids such as the methylsulfinate, p-toluenesulfonate and benzenesulfonate esters.
  • the quaternization may be conducted so that the particular salt desired is obtained directly. Alternatively, the
  • quaternary salt recovered from the synthetic reaction medium may be conveniently metathesized to another salt by techniques known in the art.
  • compositions are provided in which compounds of Formula 1 above are present as an active anticoccidial ingredient.
  • Such compositions comprise the quaternary salts intimately dispersed in or admixed with an inert carrier or diluent.
  • an inert carrier is meant one that is nonreactive with respect to the quaternary and that may be administered with safety to the animals.
  • the carrier or diluent is preferably one that is or may be an ingredient of the animal feed.
  • compositions which are a preferred feature of this aspect of the invention are the so-called feed suppler tents in which the active ingredient is present in relatively large amounts and which are suitable for addition to the poultry feed either directly or after an intermediate dilution or blending step.
  • carriers or diluents suitable for such compositions are solid orally ingestable carriers such as distillers dried grains, corn meal, citrus meal, fermentation residues, ground oyster shells, Attapulgus clay, wheat shorts, molasses solubles, corn cob meal, edible vegetable substances, toasted dehulled soya flour, soybean mill feed, antibiotic mycelia, soya grits, crushed limestone and the like.
  • the quaternary salts are intimately dispersed or admixed throughout the solid inert carrier by methods such as grinding, stirring, milling or tumbling.
  • compositions of any desired concentration may be prepared.
  • Formulations containing from about 1% to about 40% by weight, and preferably from about 225% by weight of active ingredient are particularly suitable for addition to poultry feeds, and compositions containing from about 5-15 by weight of coccidiostat are very satisfactory.
  • the active compound is normally dispersed or mixed uniformly in the diluent but in some instances may be sorbed on the carrier.
  • the optimal concentration of coccidiostat in these feed supplements will depend to some extent on the particular compound employed. Since it is convenient for the feed manufacturer to use about one pound of feed supplement for each ton of finished feed, the preferred concentration of any one of our coccidiostats in a feed supplement is partly a function of the level of active ingredient desired in he fin shed feed.
  • Examples of typical feed supplements containing a l- (2-loweralkyl-4-amino-5-pyrimidylmethyl)-loweralkylated pyridinium quaternary salt (where the lower alkyl radical in the pyrimidine ring has at least two carbon atoms) dispersed in a solid inert carrier are:
  • feed supplements are prepared by uniformly mixing the quaternary salt with the carrier or carriers.
  • the feed supplements of the type illustrated hereinabove are usually further diluted with materials such as corn meal or soybean meal before being incorporated in the animalfecd.
  • the level of coccidiostat in the carrier is brought down to from about 0.1% to about 1.0% by weight. This dilution serves to facilitate uniform distribution of the substance in the finished feed.
  • the finished feed is one that contains a source of fat, protein, carbohydrate, minerals, vitamins and other nutritional factors.
  • the amount of pyridinium quaternary salt required for optimum control of coccidiosis in poultry will, of course, vary somewhat with the specific compound or compounds empolyed.
  • the compounds of Formula I above are efl'ective when administered at levels of less than about 0.05% by weight of the feed. With the preferred compounds of the invention, i.e.
  • the poultry feed contain between about 0.0025% and 0.025% by weight of pyridinium salt.
  • the pyridinium salts are to be employed as therapeutic agents, the higher levels may be used for relaoutbreak of coccidiosis. It is desirable to employ the lowest levels that afford fully adequate control of coccidiosis in order to eliminate as far as possibleany risk of side eti'ects that might appear on prolonged feeding of the compounds.
  • pyridinium quaternary salts are desirably or advantageouslyadministered to poultry by way ..of the drinking water of the birds. This method of treatment is often employed in the therapestic use of our compounds since poultry with coccidiosis are apt to consume less solid feed than normal birds.
  • the watersoluble. quaternary salts may be added directly tothe drinking fwater; Alternatively; water-soluble powders may be prepared, in which the coccidiostat is intimately admixed with 'a suitable carrier. such as dcrtrose or sucrose, and these powdersaddedto the drinltiig water of poultry as necessary.
  • Such water-soluble ipowders may contain: any desired'concentration of coccidiostat,
  • EXAMPLE 3 One gram of 2-propyl-4-amino-5-pyrimidylmethyl bromide dihydrobromide was dissolved or suspended in 7 ml. of dry dimethylformamide, and to this solution was added 5 ml. of 2-methyl pyridine. A clear solution formed from which crystals of l-(2-propyl-4-amino-5- pyrimidyl-methyD-Z-methyl pyr'idinium bromide hydrobromide soon precipitated. These were collected by filtration and dried, melting point 242-3 "Y C. (dec.). The material was purified by recrystallization'from a methanol-ethanol mixture.
  • EXAMPLE 5 1.9 grams of p-toluene sulfonyl chloride was added gradually with shaking to a cooled (0-5 C.) solution of 1.67 grams of 2-n-propyl-4-amino-S-hydroxy-rnethyl py-- rimidine in 10 m1- of Z-rnethylpyridine. The reaction mixture, after standing threevhours in an ice bath, and 15 hours at room'temperature, was evaporated to dryness in vacuo. . The residue was dissolved in 20 ml. of water,
  • EXAMPLE 8 The pyridinium quaternary salts set forth in Table l below were synthesized utilizing processes described in preceding examples. In most experiments a 2-loweralkyl- 4-amino-5-halomethylpyrimidine was employed as the pyrimidine reactant, although in'soine cases an ester of a S-hydroxymethyl pyrimidinewas utilized.
  • B through R are hydrogen unless specified otherwise.
  • EXAMPLE 9 1 Table '50 The coecidiostatio activity of two of the pyridinium Pam; of compounds of the invention was determined by the fol-' Percent Percent o vsts lowing mcthod Compound pound Mor- Weight X10" in In Feed taiity Gain Surviving Groups of ten two-week old White Leghorn chicks were fed a mash diet containing various amounts of the compounds. The 7 compounds were uniformly dispersed in 1 ethyl 4- wny- 0015 -0 90 a the feed.
  • mm Controls 4 2 were mm Controls 4 2; also infected after 24 hours and served as positive or Norm! 00mm" 0 90 infected controls.
  • positive controls two to four groups of ten chicks each were employed. other groups of ten chicks each were fed the mash free of coccidiostat and s5 EXAMPLE 10 were not infected with coccidiosis. These served as norm1 I ls.
  • Z-Ib weralkyl-fiamino-S-broma methylpyn'midine.
  • the 2-n-propyl-4-amino-5-hydroxy methylpyrimidine obtained in Part C above is dissolved in 15 m1. of acetic acid saturated with hydrogen bromide, andthe mixture 12 bromo methylpyrimidine dihydrobromide, melting point 191-2 (3., 2-butyl-4-amino-5-bromo methylpyrimidine dihydrobromide, melting point l45l50 C., and 2-amyl-4- amino-S-bromo methylpyrimidine dih drobromide.
  • Fujita et al. Journ. of Biol. Chem, vol. 196, pages 297-303, pages 313-320 (1952).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fodder In General (AREA)
  • Plural Heterocyclic Compounds (AREA)
US829979A 1959-04-13 1959-07-28 1-(2-n-propyl-4-amino-5-pyrimidyl-methyl)-2(or 4)-methyl pyridinium salts Expired - Lifetime US3020277A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
BE587330D BE587330A (en)van) 1959-04-13
US829979A US3020277A (en) 1959-04-13 1959-07-28 1-(2-n-propyl-4-amino-5-pyrimidyl-methyl)-2(or 4)-methyl pyridinium salts
GB3698/60A GB911551A (en) 1959-04-13 1960-02-02 1-[2-(c alkyl)-4-amino-5-pyrimidylmethyl]-(c alkyl)-pyridinium quaternary salts and compositions containing them
DEM44190A DE1149010B (de) 1959-04-13 1960-02-03 Verfahren zur Herstellung von 1-[2-Alkyl-4-aminopyrimidyl-(5)-methyl]-alkylpyridiniumsalzen
CH163960A CH381694A (de) 1959-04-13 1960-02-15 Verfahren zur Herstellung von quaternären Pyridiniumsalzen
FI0327/60A FI43598B (en)van) 1959-04-13 1960-02-29
FR820636A FR1291531A (fr) 1959-04-13 1960-03-07 Fabrication de sels de pyridinium quaternaire tels que les sels de 1-(2-alkylinferieur-4-amino-5-pyrimidylméthyl)-alkylinférieur-pyridinium quaternaire
SE2942/60A SE308105B (en)van) 1959-04-13 1960-03-23
ES0257622A ES257622A1 (es) 1959-04-13 1960-04-12 Procedimiento para la preparaciën de compuestos de piridinio
US38449A US3020200A (en) 1959-04-13 1960-06-24 1-(2-alkyl-4-amino-5-pyrimidinylmethyl)-alkyl-pyridinium quaternary salts for treating coccidiosis
US38451A US3065132A (en) 1959-04-13 1960-06-24 1-(2-methyl-4-amino-5-pyrimidylmethyl)-lower alkyl pyridinium quaternary salts for treating coccidiosis
SE7084/63A SE311801B (en)van) 1959-04-13 1963-06-26
OA51542A OA02621A (fr) 1959-04-13 1964-12-31 Fabrication de sels de pyridinium quaternaire tels que les sels de 1-(2-alkylinférieur-4-amino-5-pyrimidylméthyl)-alkyinférieur-pyridinium quaternaire.

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US80568859A 1959-04-13 1959-04-13
US82997859A 1959-07-28 1959-07-28
US829979A US3020277A (en) 1959-04-13 1959-07-28 1-(2-n-propyl-4-amino-5-pyrimidyl-methyl)-2(or 4)-methyl pyridinium salts
US38451A US3065132A (en) 1959-04-13 1960-06-24 1-(2-methyl-4-amino-5-pyrimidylmethyl)-lower alkyl pyridinium quaternary salts for treating coccidiosis
US38449A US3020200A (en) 1959-04-13 1960-06-24 1-(2-alkyl-4-amino-5-pyrimidinylmethyl)-alkyl-pyridinium quaternary salts for treating coccidiosis

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US38451A Expired - Lifetime US3065132A (en) 1959-04-13 1960-06-24 1-(2-methyl-4-amino-5-pyrimidylmethyl)-lower alkyl pyridinium quaternary salts for treating coccidiosis
US38449A Expired - Lifetime US3020200A (en) 1959-04-13 1960-06-24 1-(2-alkyl-4-amino-5-pyrimidinylmethyl)-alkyl-pyridinium quaternary salts for treating coccidiosis

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US38451A Expired - Lifetime US3065132A (en) 1959-04-13 1960-06-24 1-(2-methyl-4-amino-5-pyrimidylmethyl)-lower alkyl pyridinium quaternary salts for treating coccidiosis
US38449A Expired - Lifetime US3020200A (en) 1959-04-13 1960-06-24 1-(2-alkyl-4-amino-5-pyrimidinylmethyl)-alkyl-pyridinium quaternary salts for treating coccidiosis

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CH (1) CH381694A (en)van)
DE (1) DE1149010B (en)van)
FI (1) FI43598B (en)van)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3305443A (en) * 1962-09-06 1967-02-21 Ici Ltd Anticoccidial composition and method of using same
US3374236A (en) * 1965-08-23 1968-03-19 Ciba Geigy Corp Quaternary 5-ammoniummethyl-4-amino-2-alkylmercaptoalkylene pyrimidine salts

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1545721B1 (de) * 1964-12-29 1971-01-21 Chinoin Gyogyszer Es Vegyeszet Verfahren zur Herstellung von 1-(2-Alkyl-4-amino-5-pyrimidylmethyl)-pyridinium-Verbindungen
GB1168801A (en) * 1966-05-13 1969-10-29 May & Baker Ltd Quinoline Derivatives
DE2251687A1 (de) * 1971-11-01 1973-05-10 Chinoin Gyogyszer Es Vegyeszet Neue quaternaere ammoniumverbindungen und verfahren zur herstellung derselben
US4044133A (en) * 1974-04-18 1977-08-23 Merck & Co., Inc. Anticoccidial compositions
US4369172A (en) * 1981-12-18 1983-01-18 Forest Laboratories Inc. Prolonged release therapeutic compositions based on hydroxypropylmethylcellulose
CN105434362B (zh) * 2015-11-11 2018-01-19 浙江大洋生物科技集团股份有限公司 高纯度颗粒型盐酸氨丙啉的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2587262A (en) * 1952-02-26 Chs chzghjoh
US2823160A (en) * 1955-03-29 1958-02-11 Whitmoyer Lab Inc Substituted pyrimidines compositions for chemotherapy of coccidiosis
US2895874A (en) * 1953-03-27 1959-07-21 Whitmoyer Lab Inc Diamino-pyrimidine compositions for chemotherapy of coccidiosis

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2587262A (en) * 1952-02-26 Chs chzghjoh
US2895874A (en) * 1953-03-27 1959-07-21 Whitmoyer Lab Inc Diamino-pyrimidine compositions for chemotherapy of coccidiosis
US2823160A (en) * 1955-03-29 1958-02-11 Whitmoyer Lab Inc Substituted pyrimidines compositions for chemotherapy of coccidiosis

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3305443A (en) * 1962-09-06 1967-02-21 Ici Ltd Anticoccidial composition and method of using same
US3374236A (en) * 1965-08-23 1968-03-19 Ciba Geigy Corp Quaternary 5-ammoniummethyl-4-amino-2-alkylmercaptoalkylene pyrimidine salts

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SE308105B (en)van) 1969-02-03
US3020200A (en) 1962-02-06
FR1291531A (fr) 1962-04-27
BE587330A (en)van) 1900-01-01
SE311801B (en)van) 1969-06-23
DE1149010B (de) 1963-05-22
FI43598B (en)van) 1971-02-01
US3065132A (en) 1962-11-20
CH381694A (de) 1964-09-15
GB911551A (en) 1962-11-28

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