Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/72—Two oxygen atoms, e.g. hydantoin
  • C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Definitions

• This invention relates to 1-(5-nitrofurfurylideneamino) hydantoins substituted in the 3-position of the hydantoin nucleus which may be represented by the formula:
• R represents a member of the group consisting of acetonyl, hydroxyethyl and 2-(4-pyridy1)ethyl.
• hydantoins are highly effective, relatively nontoxic systemic antimicrobial agents. They control systemic infections in animals caused by microorganisms such as Staphylococcus aureus and Eimeria tenella. Mice lethally infected with S. aureus are protected by the peroral administration of a single dose of from 105-210 mg./ kg. of these compounds given post infection as a suspension in carboxylmethylcellulose. Chickens infected with E. tenella are protected against the morbidity and mortality associated with coccidiosis provoked by that organism through the administration of these compounds incorporated in their feed at a level of 0.022% by weight.
• mice tolerable doses of these compounds range from 7702200 mg./kg. In chickens no evidence of toxic side elfect is seen at the level employed to combat coccidiosis.
• the methods which I have employed for the production of these compounds involve reacting a l-(alkylideneamino)hydantoin or a salt thereof with a compound containing a functional unit to introduce the substituent above defined as R and treating the formed 3-R-substituted-l-(alkylideneamino)hydantoin under hydrolytic conditions if necessary to free the 3-R-substituted-1-aminohydantoin for reaction with 5-nitro-2-furaldehyde or a derivative thereof hydrolyzable thereto.
• a representative schema In order to convert the I i-substituted-l-(alkylideneamino) hydantoins depicted in the above representative schema (I and II) to the desired S-nitro furfurylidene compound, I have found it to be advantageous to hydrolyze them in an acidified aqueous medium such as aqueous mineral acid under the influence of heat and to add 5- nitrofuraldehyde or an equivalent thereof, such as S-nitrofuraldehyde diacetate which is readily hydrolyzed under the reaction conditions, to the medium. Where the alkylidene component is volatile, steam distillation in the presence of acid is an effective means for removing the volatile component from the reaction mixture and at the same time effecting hydrolysis.
• 5-nitro-2-furaldehyde diaoetate may be used accompanied by heating to effect its hydrolysis.

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

Priority Applications (14)

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Cited By (3)

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Citations (1)

Family Cites Families (1)

• 0
  • FR FR1310188D patent/FR1310188A/fr not_active Expired
• 1960
  • 1960-12-27 US US78315A patent/US3097202A/en not_active Expired - Lifetime
• 1961
  • 1961-11-29 DE DEN20887A patent/DE1147590B/de active Pending
  • 1961-11-29 DE DEN20886A patent/DE1147589B/de active Pending
  • 1961-12-06 CH CH1413961A patent/CH414651A/de unknown
  • 1961-12-06 GB GB43775/61A patent/GB1002644A/en not_active Expired
  • 1961-12-06 CH CH667866A patent/CH416652A/de unknown
  • 1961-12-06 CH CH1528665A patent/CH411909A/de unknown
  • 1961-12-21 SE SE12807/61A patent/SE300107B/xx unknown
  • 1961-12-21 FR FR882730A patent/FR1706M/fr not_active Expired
  • 1961-12-22 BE BE611940D patent/BE611940A/xx unknown
  • 1961-12-26 BR BR135262/61A patent/BR6135262D0/pt unknown
  • 1961-12-26 ES ES0273245A patent/ES273245A1/es not_active Expired
  • 1961-12-27 NL NL272956D patent/NL272956A/xx unknown

Patent Citations (1)

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