GB1206232A - Improvements in or relating to sulphanilamide derivatives - Google Patents

Improvements in or relating to sulphanilamide derivatives

Info

Publication number
GB1206232A
GB1206232A GB74568A GB74568A GB1206232A GB 1206232 A GB1206232 A GB 1206232A GB 74568 A GB74568 A GB 74568A GB 74568 A GB74568 A GB 74568A GB 1206232 A GB1206232 A GB 1206232A
Authority
GB
United Kingdom
Prior art keywords
cyclopropyl
group
methoxy
sulphanilamide
pyrimidinol
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
GB74568A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB1206232A publication Critical patent/GB1206232A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56One oxygen atom and one sulfur atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60Three or more oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/69Benzenesulfonamido-pyrimidines

Landscapes

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

Abstract

1,206,232. Sulphanilamide derivatives. J. R. GEIGY A.G. 5 Jan., 1968 [6 Jan., 1967], No. 745/68. Heading C2C. Compounds (I) (including salts with organic and inorganic bases) wherein R 1 and R 2 signify hydrogen or cyclopropyl (one of R 1 and R 2 being cyclopropyl) and R 3 signifies an alkyl or alkoxy group, are prepared by reducing a compound related to that illustrated above wherein in place of R 1 and R 2 are the groups R<SP>1</SP> 1 and R<SP>1</SP> 2 signifying cyclopropyl or alkylthio (one of R<SP>1</SP> 1 and R<SP>1</SP> 2 being cyclopropyl), R 3 is as defined above and in place of the -NH 2 group is the group -X signifying the amino group or a nitrogencontaining group which is convertible into the amino group. 6 - Cyclopropyl - 5 - methoxy - 2 - mercapto - 4 - pyrimidinol, obtained by refluxing α-methoxy- #-oxo-cyclopropane propionic acid ethyl ester and thiourea in ethanol in the presence of sodium, is converted to 6-cyclopropyl-5 -methoxy 2 - methylthio - 4 - pyrimidinol utilizing methyl iodide and sodium hydroxide; the 4-pyrimidinol is converted to the corresponding 4- chloropyrimidine by heating with phosphorus oxychloride, which in turn is converted to N<SP>1</SP> - (6 - cyclopropyl - 5 - methoxy - 2 - methylthio- 4 - pyrimidinyl) - sulphanilamide utilizing the sodium salt of sulphanilamide in the presence of trimethylamine, dimethyl sulphoxide and dimethyl formamide. Pharmaceutical preparations suitable for the treatment of virus diseases contain as active ingredient compounds (I); administration is orally or parenterally.
GB74568A 1967-01-06 1968-01-05 Improvements in or relating to sulphanilamide derivatives Expired GB1206232A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH20167A CH476739A (en) 1967-01-06 1967-01-06 Process for the preparation of new derivatives of sulfanilamide

Publications (1)

Publication Number Publication Date
GB1206232A true GB1206232A (en) 1970-09-23

Family

ID=4181546

Family Applications (1)

Application Number Title Priority Date Filing Date
GB74568A Expired GB1206232A (en) 1967-01-06 1968-01-05 Improvements in or relating to sulphanilamide derivatives

Country Status (12)

Country Link
AT (1) AT275529B (en)
BE (1) BE709034A (en)
CH (1) CH476739A (en)
DE (1) DE1695106A1 (en)
DK (1) DK116593B (en)
ES (1) ES348964A1 (en)
FR (1) FR1567151A (en)
GB (1) GB1206232A (en)
NL (1) NL6800191A (en)
NO (1) NO122651B (en)
SE (1) SE339472B (en)
YU (1) YU33108B (en)

Also Published As

Publication number Publication date
CH476739A (en) 1969-08-15
NO122651B (en) 1971-07-26
ES348964A1 (en) 1969-03-16
FR1567151A (en) 1969-05-16
DE1695106A1 (en) 1971-04-08
NL6800191A (en) 1968-07-08
BE709034A (en) 1968-07-05
YU33108B (en) 1976-04-30
DK116593B (en) 1970-01-26
AT275529B (en) 1969-10-27
SE339472B (en) 1971-10-11
YU1868A (en) 1975-10-31

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees