GB911551A - 1-[2-(c alkyl)-4-amino-5-pyrimidylmethyl]-(c alkyl)-pyridinium quaternary salts and compositions containing them - Google Patents

1-[2-(c alkyl)-4-amino-5-pyrimidylmethyl]-(c alkyl)-pyridinium quaternary salts and compositions containing them

Info

Publication number
GB911551A
GB911551A GB3698/60A GB369860A GB911551A GB 911551 A GB911551 A GB 911551A GB 3698/60 A GB3698/60 A GB 3698/60A GB 369860 A GB369860 A GB 369860A GB 911551 A GB911551 A GB 911551A
Authority
GB
United Kingdom
Prior art keywords
amino
moles
anion
reacting
alkyl
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
Application number
GB3698/60A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB911551A publication Critical patent/GB911551A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Fodder In General (AREA)

Abstract

The anion, X, in quaternary salts of the general formula <FORM:0911551/IV(a)/1> may be derived from a polymer, especially it may be a polystyrenesulphonate ion; otherwise R and R1 are C1-5 alkyl groups n is 1, 2 or 3, and b and c are whole numbers such that the charge on b moles of cation is neutralized by c moles of the anion X (see also Group IV(b)).ALSO:The invention comprises pyrimidylmethylalkylpyridinium salts of the general formula <FORM:0911551/IV (b)/1> (including salts formed with polymers such as polystyrenesulphonic acid (see Group IV(a)) where R and R1 are lower alkyl radicals, n has a value 1, 2 or 3, X is an anion and b and c are positive numbers such that the positive charge of b moles of cation is neutralised by c moles of anion X, "lower" indicating 1-5 carbon atoms in the group so described; the preparation thereof by reacting a lower alkylpyridine and a 2-lower alkyl-4-amino-5-hydroxymethylpyrimidin ester of a strong acid, optionally in the form of its acid addition salt; and compositions comprising the compounds of the invention and an inert diluent. 2-Propyl-4-amino-5-bromomethyl pyrimidine dihydrobromide is prepared by reacting butyramidine with ethoxymethylene-malonitrile to give 2-propyl-4-amino-5-cyanopyrimidine, reducing this to give the 5-aminomethylpyrimidine dihydrochloride, reacting this with nitrous acid to give the -5-hydroxymethylpyrimidine and reacting this with hydrogen bromide. The 2-isopropyl-2-butyl- and 2-amyl-analogues are also prepared. Compositions for veterinary use against coccidinosis are in the form of poultry feed supplements preferably containing 1-40% of the active ingredient together with solid orally ingestible carriers, or in the form of a watersoluble powder preferably containing 1-25% of the active ingredient dispersed in an edible water-soluble carrier, or an animal feedstuff preferably containing 0.0005-0.05% of the active ingredient.
GB3698/60A 1959-04-13 1960-02-02 1-[2-(c alkyl)-4-amino-5-pyrimidylmethyl]-(c alkyl)-pyridinium quaternary salts and compositions containing them Expired GB911551A (en)

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

Publications (1)

Publication Number Publication Date
GB911551A true GB911551A (en) 1962-11-28

Family

ID=27534658

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3698/60A Expired 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

Country Status (8)

Country Link
US (3) US3020277A (en)
BE (1) BE587330A (en)
CH (1) CH381694A (en)
DE (1) DE1149010B (en)
FI (1) FI43598B (en)
FR (1) FR1291531A (en)
GB (1) GB911551A (en)
SE (2) SE308105B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB984375A (en) * 1962-09-06 1965-02-24 Ici Ltd Veterinary compositions of sulphaquinoxaline and pyrimidine derivatives
DE1545721B1 (en) * 1964-12-29 1971-01-21 Chinoin Gyogyszer Es Vegyeszet Process for the preparation of 1- (2-alkyl-4-amino-5-pyrimidylmethyl) pyridinium compounds
US3374236A (en) * 1965-08-23 1968-03-19 Ciba Geigy Corp Quaternary 5-ammoniummethyl-4-amino-2-alkylmercaptoalkylene pyrimidine salts
GB1168801A (en) * 1966-05-13 1969-10-29 May & Baker Ltd Quinoline Derivatives
DE2251687A1 (en) * 1971-11-01 1973-05-10 Chinoin Gyogyszer Es Vegyeszet NEW QUATERNAERE AMMONIUM COMPOUNDS AND METHOD OF MAKING THE SAME
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 (en) * 2015-11-11 2018-01-19 浙江大洋生物科技集团股份有限公司 The preparation method of high-purity granular pattern Amprolium Hydrochloride

Family Cites Families (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

Also Published As

Publication number Publication date
US3020277A (en) 1962-02-06
SE311801B (en) 1969-06-23
DE1149010B (en) 1963-05-22
US3065132A (en) 1962-11-20
SE308105B (en) 1969-02-03
FR1291531A (en) 1962-04-27
FI43598B (en) 1971-02-01
CH381694A (en) 1964-09-15
US3020200A (en) 1962-02-06
BE587330A (en) 1900-01-01

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