GB922725A - Pyrazine derivatives - Google Patents

Pyrazine derivatives

Info

Publication number
GB922725A
GB922725A GB2396861A GB2396861A GB922725A GB 922725 A GB922725 A GB 922725A GB 2396861 A GB2396861 A GB 2396861A GB 2396861 A GB2396861 A GB 2396861A GB 922725 A GB922725 A GB 922725A
Authority
GB
United Kingdom
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
GB2396861A
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 GB922725A publication Critical patent/GB922725A/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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic 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.
GB2396861A 1960-07-08 1961-07-03 Pyrazine derivatives Expired GB922725A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
GB922725A true GB922725A (en) 1963-04-03

Family

ID=11139461

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2396861A Expired GB922725A (en) 1960-07-08 1961-07-03 Pyrazine derivatives

Country Status (3)

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

Cited By (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
US5877319A (en) * 1996-07-11 1999-03-02 Lonza, Ag Process for preparing 3-alkoxy-5-alkylpyrazin-2-amines
JPH1171354A (en) * 1997-07-03 1999-03-16 Lonza Ag Production of alkoxypyrazine derivative

Cited By (7)

* 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
US5877319A (en) * 1996-07-11 1999-03-02 Lonza, Ag Process for preparing 3-alkoxy-5-alkylpyrazin-2-amines
US5998618A (en) * 1996-07-11 1999-12-07 Lonza Ag Process for preparing 3-alkoxy-5-alkypyrazin-2-amines
JPH1171354A (en) * 1997-07-03 1999-03-16 Lonza Ag Production of alkoxypyrazine derivative
US6066736A (en) * 1997-07-03 2000-05-23 Lonza Ag Process for preparing alkoxypyrazine derivatives
US6291674B2 (en) 1997-07-03 2001-09-18 Lonza Ag Process for preparing alkoxypyrazine derivatives
JP4660862B2 (en) * 1997-07-03 2011-03-30 ロンザ リミテッド Process for producing alkoxypyrazine derivative

Also Published As

Publication number Publication date
ES268859A1 (en) 1961-12-16
BE605897A (en) 1962-01-08

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