Patent GB-1479879-A (GB)
Title: Pyridine sulphonamides their preparation and their use for controlling coccidiosis
IPC: C07D213/70
Filed: 1976-05-04
Abstract: 1479879 Pyridine sulphonamides SANKYO CO Ltd 4 May 1976 [15 May 1975 9 Dec 1975] 18130/76 Heading C2C Novel compounds of formula wherein: R<SP>1</SP> represents a hydrogen atom, R<SP>2</SP> represents a nitro group, and R<SP>3</SP> and R<SP>4</SP> are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or an alkoxyalkyl group having from 1 to 4 carbon atoms in the alkoxy moiety and from 2 to 4 carbon atoms in the alkyl moiety, or R<SP>3</SP> represents a hydrogen atom and R<SP>4</SP> represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxyalkyl group having from 1 to 4 carbon atoms in the alkoxy moiety and from 2 to 4 carbon atoms in the alkyl moiety, an alkenyl group having 3 or 4 carbon atoms, an alkanoyl group having from 1 to 18 carbon atoms or a benzyl group which is unsubstituted or has one or more halogen, cyano, C 1-4  alkyl or C 1-4  alkoxy substituents; or R<SP>1</SP> represents a hydrogen atom, R<SP>2</SP> represents an amino group or a monoalkylamino group having from 1 to 3 carbon atoms, and each of R<SP>3</SP> and R<SP>4</SP> represents a hydrogen atom or each represents the same or different alkyl group having from 1 to 4 carbon atoms; or R<SP>1</SP> represents an amino group, R<SP>2</SP> represents a nitro group, and R<SP>3</SP> and R<SP>4</SP> are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or R<SP>3</SP> represents a hydrogen atom and R<SP>4</SP> represents an alkyl group having from 1 to 4 carbon atoms or an alkenyl group having 3 or 4 carbon atoms; or R<SP>1</SP> represents a group of formula -NR<SP>5</SP>R<SP>6</SP> (in which R<SP>5</SP> and R<SP>6</SP> are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or R<SP>5</SP> represents a hydrogen atom and R<SP>6</SP> represents an alkyl group having from 1 to 4 carbon atoms, an alkenyl group having 3 or 4 carbon atoms or a benzyl group which is unsubstituted or has one or more halogen, cyano, C 1-4  alkyl or C 1-4  alkoxy substituents), R<SP>2</SP> represents a nitro group, and R<SP>3</SP> and R<SP>4</SP> are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or R<SP>3</SP> represents a hydrogen atom and R<SP>4</SP> represents an alkyl group having from 1 to 4 carbon atoms, an alkenyl group having 3 or 4 carbon atoms or a benzyl group which is unsubstituted or has one or more halogen, cyano, C 1-4  alkyl or C 1-4  alkoxy substituents, are used in anticoccidial compositions. Preferred compounds are in four groups (a) where R<SP>1</SP> represents a hydrogen atom, R<SP>2</SP> represents a nitro group and R<SP>3</SP> and R<SP>4</SP> are the same or different and each represents an alkyl or alkoxyalkyl, or R<SP>3</SP> represents a hydrogen atom and R<SP>4</SP> represents a hydrogen atom, or alkyl, alkoxyalkyl or alkanoyl (2-8C), (b) where R<SP>1</SP> represents hydrogen, R<SP>2</SP> an amino group, R<SP>3</SP> and R<SP>4</SP> are the same or different and each represents a methyl or ethyl group, (c) R<SP>1</SP> represents an amino group, R<SP>2</SP> a nitro group and R<SP>3</SP> and R<SP>4</SP> are the same or different and each represents a methyl or ethyl group or R<SP>3</SP> represents a hydrogen atom and R<SP>4</SP> represents a methyl or ethyl group and (d) R<SP>1</SP> represents -NR<SP>5</SP>R<SP>6</SP> (in which R<SP>5</SP> and R<SP>6</SP> are the same or different and each represents methyl or ethyl or R<SP>5</SP> represents a hydrogen and R<SP>6</SP> a methyl or ethyl, R<SP>2</SP> a nitro group and R<SP>3</SP> and R<SP>4</SP> are the same or different and each represents a methyl or ethyl group or R<SP>3</SP> represents a hydrogen and R<SP>4</SP> a methyl or ethyl group. The compounds of type (a) are prepared by reacting 5-bromo-3- pyridinesulphonamide with ammonia, optionally converting the amino to nitro and optionally acylating to the N-alkanoyl (5-nitro- 3-pyridine)sulphonamide with an acyl anhydride or chloride; of type (b) by hydrolysing 5-bromo-3-pyridine sulphonyl chloride to the acid, aminating and oxidizing with sulphuric acid and hydrogen peroxide which is chlorinated with phosphorus pentachloride and reacted with an amine; of type (c) by reacting 5-bromo- 3-pyridinesulphonyl chloride with an amine which is reacted with ammonia or an alkylamine in the presence of cupric sulphate; (d) by reacting 6-amino-5-nitro-3-pyridine sulphonic acid with phosphorus pentachloride followed by an amine or by reacting a 6-chloro-5-nitro- 3-pyridine sulphonyl chloride with an amine. The compounds may be used in compositions in concentrations from 0À004 to 0À1% by weight of feed and formulations are given with anticoccidial activity.