ES268859A1 - Pyrazine derivatives - Google Patents

Pyrazine derivatives

Info

Publication number
ES268859A1
ES268859A1 ES0268859A ES268859A ES268859A1 ES 268859 A1 ES268859 A1 ES 268859A1 ES 0268859 A ES0268859 A ES 0268859A ES 268859 A ES268859 A ES 268859A ES 268859 A1 ES268859 A1 ES 268859A1
Authority
ES
Spain
Prior art keywords
methyl
aminopyrazine
alkyl
chloro
hydroxy
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
ES0268859A
Other languages
Spanish (es)
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.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
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 Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Publication of ES268859A1 publication Critical patent/ES268859A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
    • C07D241/20—Nitrogen atoms
    • C07D241/22—Benzenesulfonamido pyrazines

Landscapes

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

Abstract

The invention comprises 3-alkoxy-2-sulphapyrazines of the formula <FORM:0922725/IV(a)/1> wherein R1 and/or R2 are H or alkyl (at least one being alkyl), R3 = H or Ac, R4 = -SO2-C6H4-NHAc, -SO2-C6H4-NH2 or -SO2-C6H4-NO2, Alk represents an alkyl radical of 1-4 carbon atoms and Ac represents an aliphatic monocarboxylic acyl radical of 1-4 carbon atoms and the preparation of these compounds by treating the corresponding aminopyrazine with a p-acylaminobenzene-sulphonyl halide in the presence of a tertiary amine and if desired hydrolysing the resulting p-acylamino-derivative with alkali or acid or by treating the aminopyrazine with a p-nitrobenzenesulphonyl halide and reducing the resulting nitrobenzenesulphonamido-pyrazine with hydrogen in the presence of a hydrogenation catalyst such as palladium/charcoal. Startinb materials. 5-Methyl- 3-chloro-2-aminopyrazine is made by treating 5-methyl-3-hydroxy-2-aminopyrazine with POCl3. 6-Methyl-3-chloro-2-aminopyrazine is made by converting 6-methyl-3-hydroxy- 2-carbamoylpyrazine into 6-methyl-3-hydroxy -2-aminopyrazine by Hoffmann reaction and chlorinating with POCl3. The 5-methyl-3-chloro-2-aminopyrazine may be converted into the 6-methyl-3-chloro-2-aminopyrazine and vice versa by treating successively with nitrous acid to give a 2-hydroxy-3-chloro-(5 or 6)-methyl-pyrazine, ammonia to give 2-hydroxy-3-amino-(5 or 6) methyl-pyrazine, and finally with POCl3.ALSO:Pharmaceutical preparations for treatment of bacterial infections comprise compounds of the formula <FORM:0922725/VI/1> wherein R1 and/or R2 are H or alkyl (at least one being alkyl), R3 = H or Ac, R4 = -SO2-C6H4-NHAc, -SO2-C6H4-NH2 or -SO2 -C6H4-NO2, Alk represents an alkyl radical of 1-4 carbon atoms and Ac represents an aliphatic monocarboxylic acyl radical of 1-4 carbon atoms, optionally admixed with other sulphonamides or antibiotics, and a carrier. The preparations may take the form of powders, tablets, pills or syrups and may be mixed with animal foods.
ES0268859A 1960-07-08 1961-07-07 Pyrazine derivatives Expired ES268859A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT1210860 1960-07-08

Publications (1)

Publication Number Publication Date
ES268859A1 true ES268859A1 (en) 1961-12-16

Family

ID=11139461

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0268859A Expired ES268859A1 (en) 1960-07-08 1961-07-07 Pyrazine derivatives

Country Status (3)

Country Link
BE (1) BE605897A (en)
ES (1) ES268859A1 (en)
GB (1) GB922725A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE943301C (en) * 1951-10-17 1956-05-17 Busch Jaeger Duerener Metall Socket for fluorescent tubes
CA2209465C (en) * 1996-07-11 2008-04-29 Lonza Ag Process for preparing 3-alkoxy-5-alkylpyrazin-2-amines
CA2241933C (en) * 1997-07-03 2008-10-07 Lonza Ag Process for preparing alkoxypyrazine derivatives

Also Published As

Publication number Publication date
GB922725A (en) 1963-04-03
BE605897A (en) 1962-01-08

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