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 themInfo
- 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
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.
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)
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)
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 |
-
0
- BE BE587330D patent/BE587330A/xx unknown
-
1959
- 1959-07-28 US US829979A patent/US3020277A/en not_active Expired - Lifetime
-
1960
- 1960-02-02 GB GB3698/60A patent/GB911551A/en not_active Expired
- 1960-02-03 DE DEM44190A patent/DE1149010B/en active Pending
- 1960-02-15 CH CH163960A patent/CH381694A/en unknown
- 1960-02-29 FI FI0327/60A patent/FI43598B/fi active
- 1960-03-07 FR FR820636A patent/FR1291531A/en not_active Expired
- 1960-03-23 SE SE2942/60A patent/SE308105B/xx unknown
- 1960-06-24 US US38449A patent/US3020200A/en not_active Expired - Lifetime
- 1960-06-24 US US38451A patent/US3065132A/en not_active Expired - Lifetime
-
1963
- 1963-06-26 SE SE7084/63A patent/SE311801B/xx unknown
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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