FR2283129A1 - 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine prodn - strong bacteri-cide, for increasing activity of sulpha drugs - Google Patents

2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine prodn - strong bacteri-cide, for increasing activity of sulpha drugs

Info

Publication number
FR2283129A1
FR2283129A1 FR7407043A FR7407043A FR2283129A1 FR 2283129 A1 FR2283129 A1 FR 2283129A1 FR 7407043 A FR7407043 A FR 7407043A FR 7407043 A FR7407043 A FR 7407043A FR 2283129 A1 FR2283129 A1 FR 2283129A1
Authority
FR
France
Prior art keywords
bacteri
cide
trimethoxybenzyl
prodn
diamino
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.)
Granted
Application number
FR7407043A
Other languages
French (fr)
Other versions
FR2283129B1 (en
Inventor
Norio Tokutake
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation Ltd
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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to FR7407043A priority Critical patent/FR2283129A1/en
Publication of FR2283129A1 publication Critical patent/FR2283129A1/en
Application granted granted Critical
Publication of FR2283129B1 publication Critical patent/FR2283129B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C07D239/62—Barbituric acids
    • 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
    • C07D239/30—Halogen atoms or nitro radicals
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim

Landscapes

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

Abstract

The following process is new: (VI) is a barteriocide. Bactericidal activity of sulpha drugs is strongly increased by admixture with (VI). 5.494 g. (I), 4.004 g. (II) (R=Et), 256 mg. piperidine, 120 mg. acetic acid and 20 ml. dry benzene are stirred overnight at room temp. then refluxed for 3.5 hr. with azeotropic distln. of H2O. The cooled reaction mixt. is diluted with ether and unreacted (I) is removed by shaking with 5% aq. sodium hydrogensulphite. The ether layer is washed (H2O, aq. NaHCO3, H2O), dried and distld. to give 7.645 g. diethyl 3,4,5-trimethoxybenzylidene malonate. This in soln. in 35 ml. EtOAc is mixed with 0.2 g. of 10% Pd/C and treated with H2 at 40 degrees C for 2 hrs. to give 7.349 g. (III) (R=Et), recrystd. hexane, m.p. 78-78.5 degrees C. (VI) is obtd. via intermediates (IV) and (V) from (III).
FR7407043A 1974-03-01 1974-03-01 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine prodn - strong bacteri-cide, for increasing activity of sulpha drugs Granted FR2283129A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7407043A FR2283129A1 (en) 1974-03-01 1974-03-01 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine prodn - strong bacteri-cide, for increasing activity of sulpha drugs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7407043A FR2283129A1 (en) 1974-03-01 1974-03-01 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine prodn - strong bacteri-cide, for increasing activity of sulpha drugs

Publications (2)

Publication Number Publication Date
FR2283129A1 true FR2283129A1 (en) 1976-03-26
FR2283129B1 FR2283129B1 (en) 1978-06-02

Family

ID=9135671

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7407043A Granted FR2283129A1 (en) 1974-03-01 1974-03-01 2,4-Diamino-5-(3,4,5-trimethoxybenzyl) pyrimidine prodn - strong bacteri-cide, for increasing activity of sulpha drugs

Country Status (1)

Country Link
FR (1) FR2283129A1 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1459417A (en) * 1964-11-12 1966-04-29 Hoffmann La Roche Process for the preparation of pyrimidine derivatives
FR1563925A (en) * 1967-02-27 1969-04-18
DE2258238A1 (en) * 1971-12-01 1973-06-07 Plantex Ltd 5-Benzylpyrimidines prepn - from benzaldehyde and cyanoacetic acid ester via 2,4-diamino-5-benzyl-6-hydroxypyrimidine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1459417A (en) * 1964-11-12 1966-04-29 Hoffmann La Roche Process for the preparation of pyrimidine derivatives
FR1563925A (en) * 1967-02-27 1969-04-18
DE2258238A1 (en) * 1971-12-01 1973-06-07 Plantex Ltd 5-Benzylpyrimidines prepn - from benzaldehyde and cyanoacetic acid ester via 2,4-diamino-5-benzyl-6-hydroxypyrimidine

Also Published As

Publication number Publication date
FR2283129B1 (en) 1978-06-02

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