CA1108611A - 2,4-diamino-5-benzylpyrimidines and process for the manufacture thereof - Google Patents

2,4-diamino-5-benzylpyrimidines and process for the manufacture thereof

Info

Publication number
CA1108611A
CA1108611A CA315,867A CA315867A CA1108611A CA 1108611 A CA1108611 A CA 1108611A CA 315867 A CA315867 A CA 315867A CA 1108611 A CA1108611 A CA 1108611A
Authority
CA
Canada
Prior art keywords
denotes
alkylthio
alkoxy
so2r
mercapto
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
CA315,867A
Other languages
English (en)
French (fr)
Inventor
Ivan Kompis
Alexander E. Wick
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Application granted granted Critical
Publication of CA1108611A publication Critical patent/CA1108611A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/02—Monothiocarbamic acids; Derivatives thereof
    • C07C333/08—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
CA315,867A 1977-11-10 1978-11-06 2,4-diamino-5-benzylpyrimidines and process for the manufacture thereof Expired CA1108611A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
LU78,487 1977-11-10
LU78487 1977-11-10
CH9776/78 1978-09-19
CH977678 1978-09-19

Publications (1)

Publication Number Publication Date
CA1108611A true CA1108611A (en) 1981-09-08

Family

ID=25705315

Family Applications (1)

Application Number Title Priority Date Filing Date
CA315,867A Expired CA1108611A (en) 1977-11-10 1978-11-06 2,4-diamino-5-benzylpyrimidines and process for the manufacture thereof

Country Status (22)

Country Link
EP (3) EP0032395B1 (OSRAM)
JP (1) JPS5476586A (OSRAM)
AR (2) AR228423A1 (OSRAM)
AT (1) AT359070B (OSRAM)
AU (1) AU527943B2 (OSRAM)
BR (1) BR7807425A (OSRAM)
CA (1) CA1108611A (OSRAM)
DE (1) DE2847825A1 (OSRAM)
DK (1) DK144418C (OSRAM)
ES (2) ES474921A1 (OSRAM)
FI (1) FI783368A7 (OSRAM)
FR (4) FR2422647A1 (OSRAM)
GB (3) GB2087378B (OSRAM)
GR (1) GR71725B (OSRAM)
IL (1) IL55869A (OSRAM)
IT (1) IT1100210B (OSRAM)
MC (1) MC1222A1 (OSRAM)
NL (1) NL7811170A (OSRAM)
NO (1) NO783775L (OSRAM)
PH (1) PH15918A (OSRAM)
PT (1) PT68773A (OSRAM)
SE (1) SE7811593L (OSRAM)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1138146B (it) * 1981-08-11 1986-09-17 Proter Spa Processo per la produzione della 2,4-diammino-(3,5-dimetossi-4-metos sietossi-benzil)-pirimidina
JPS5888368A (ja) * 1981-11-09 1983-05-26 ザ・ウエルカム・フアウンデ−シヨン・リミテツド ベンジルピリミジン誘導体の製造法
DE3304202A1 (de) * 1983-02-08 1984-08-09 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von aromatischen aldehyden
DE3603577A1 (de) * 1986-02-06 1987-08-13 Joachim K Prof Dr Seydel Neue substituierte 2,4-diamino-5-benzylpyrimidine, deren herstellung und deren verwendung als arzneimittel mit antibakterieller wirksamkeit
IE913974A1 (en) * 1990-11-14 1992-05-20 Protos Corp Specific inhibition of dihydrofolate reductase and compounds¹therefor

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2165362A1 (de) * 1970-12-29 1972-07-27 Nisshin Flour Milling Co. Ltd., Tokio .-Verfahren zur Herstellung von Pyrimidinderivaten
NL7200058A (OSRAM) * 1971-01-21 1972-07-25
IL38276A (en) * 1971-12-01 1976-09-30 Plantex Ltd Process for the preparation of 2,4-diamino-5-substituted benzylpyrimidines
BE798724A (fr) * 1973-04-26 1973-08-16 En Abrege Socechim Soc Et Chim Nouveaux composes chimiques
DK136470B (da) * 1973-11-08 1977-10-17 Hoffmann La Roche Analogifremgangsmåde til fremstilling af 2,4-diamino-5-benzylpyrimidinderivater eller salte deraf.
CH605828A5 (OSRAM) * 1974-12-24 1978-10-13 Hoffmann La Roche
DE2635765C3 (de) * 1976-08-09 1979-02-08 Ludwig Heumann & Co Gmbh, 8500 Nuernberg Verfahren zur Herstellung von 2,4-EMamino-5-(3',4'r5'-trimethoxybenzyl)-pyrimidin

Also Published As

Publication number Publication date
FR2422404B1 (OSRAM) 1983-02-04
EP0032395A1 (de) 1981-07-22
GB2007669A (en) 1979-05-23
FR2422648B1 (OSRAM) 1983-02-04
FR2422632B1 (OSRAM) 1983-02-04
EP0035624B1 (de) 1984-07-04
FR2422648A1 (fr) 1979-11-09
IT7829638A0 (it) 1978-11-09
JPS5476586A (en) 1979-06-19
ES481038A1 (es) 1980-04-01
NL7811170A (nl) 1979-05-14
ATA803378A (de) 1980-03-15
FI783368A7 (fi) 1979-05-11
PT68773A (en) 1978-12-01
GB2007669B (en) 1982-10-20
IT1100210B (it) 1985-09-28
DK500178A (da) 1979-05-11
SE7811593L (sv) 1979-05-11
GB2086882A (en) 1982-05-19
AU4132378A (en) 1979-05-17
IL55869A (en) 1983-05-15
FR2422647B1 (OSRAM) 1983-02-04
GB2086882B (en) 1982-12-15
FR2422632A1 (fr) 1979-11-09
EP0032395B1 (de) 1983-03-23
EP0035624A2 (de) 1981-09-16
FR2422647A1 (fr) 1979-11-09
AR228423A1 (es) 1983-03-15
ES474921A1 (es) 1979-12-01
MC1222A1 (fr) 1979-07-20
AT359070B (de) 1980-10-27
NO783775L (no) 1979-05-11
PH15918A (en) 1983-04-22
GR71725B (OSRAM) 1983-06-22
FR2422404A1 (fr) 1979-11-09
EP0003212A1 (de) 1979-08-08
AR222831A1 (es) 1981-06-30
GB2087378B (en) 1983-01-06
DE2847825A1 (de) 1979-05-17
EP0003212B1 (de) 1982-03-17
IL55869A0 (en) 1979-01-31
DK144418B (da) 1982-03-08
BR7807425A (pt) 1979-07-24
GB2087378A (en) 1982-05-26
EP0035624A3 (en) 1981-09-23
AU527943B2 (en) 1983-03-31
DK144418C (da) 1982-08-09

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