ES338265A1 - New sulphanilamide derivatives - Google Patents

New sulphanilamide derivatives

Info

Publication number
ES338265A1
ES338265A1 ES338265A ES338265A ES338265A1 ES 338265 A1 ES338265 A1 ES 338265A1 ES 338265 A ES338265 A ES 338265A ES 338265 A ES338265 A ES 338265A ES 338265 A1 ES338265 A1 ES 338265A1
Authority
ES
Spain
Prior art keywords
cyclopropyl
alkyl
formula
compounds
compound
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
ES338265A
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.)
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 ES338265A1 publication Critical patent/ES338265A1/en
Expired legal-status Critical Current

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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
    • C07D239/30—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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • 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
    • C07D239/52—Two oxygen 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
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy 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
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
    • 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
    • C07D239/56—One oxygen atom and one sulfur atom
    • 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
    • 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
    • C07D239/69—Benzenesulfonamido-pyrimidines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of general formula wherein R 1 is hydrogen, chlorine, C 1-3 alkyl, or C 1-2 alkoxy or alkylthio R 2 is hydrogen, chlorine, C 1-3 alkyl, C 1-2 alkoxy or alkylthio, or cyclopropyl R 3 is hydrogen, C 1-3 alkyl, C 1-2 alkoxy or cyclopropyl one of R 2 and R 3 being cyclopropyl and salts thereof and their preparation by: (a) reaction of a compound of Formula II with one of Formula III (wherein X is NH 2 or a nitrogen-containing group convertible thereinto by hydrolysis or reduction, one of A 1 and A 2 is imino while the other represents a direct bond, Y and Z are reactive atoms or radicals which can be split off together) and, if necessary, converting the group X of the reaction product into NH 2 (b) reaction of a compound of Formula V with one of Formula VI, or an acetal, enol ether, enamine or ketal thereof (wherein R 1 1 is hydrogen or C 1-3 alkyl, R 2 1 is hydrogen, C 1-3 alkyl or cyclopropyl, X and R 3 are as above, one of R 2 1 and R 3 being cyclopropyl), and if necesary, converting X in the reaction product to NH 2 , to give a compound of Formula I wherein R 1 and R 2 have the values of R 1 1 and R 2 1 respectively and (c) reacting a compound of Formula V above with a dialkyl ester of cyclopropyl malonic acid or with an alkyl ester of a #-oxo-carboxylic acid of Formula VIII wherein R 2 1 and R 3 are as above, one of them being cyclopropyl, to form a compound of Formula IX (wherein R 2 11 is hydrogen, C 1-3 alkyl, cyclopropyl, or hydroxyl) and reacting this with an inorganic acid chloride to produce a compound of Formula I wherein R 1 and possibly R 2 is chlorine, and if necessary, converting the group X of the reaction product into NH 2 . Products of processes (a) and (c) wherein R 1 and/or R 2 is chlorine may be converted to the corresponding compounds in which R 1 and/or R 2 is hydrogen, alkoxy, or alkylthio. Any product may be converted into a salt. Pyrimidine compounds of Formula III wherein As is a direct bond, Z is alkylsulphonyl or chlorine and R 3 is cyclopropyl are made by condensing a cyclopropyl malonic acid dialkyl ester with thiourea followed by methylation, or with S-methyl isourea in either case to form 2-methylthio-5-cyclopropyl-pyrimidine-4,6-diol, which is then converted either to (a) the corresponding 4,6-dichloro or 4,6-dialkoxy compounds followed by oxidation of the 2-methylthio group to a methylsulphonyl group, or to (b) the corresponding 2,4,6-trichloro compound (via the 2,4,6-triol). Compounds of Formula III wherein A is a direct bond, Z is alkylsulphonyl or chlorine, and R 2 is cyclopropyl are made by condensing a #-oxo-#-cyclopropylpropionic acid ester optionally bearing an [alpha]-alkyl or alkoxy group with thiourea or an S-alkyl isourea to form a 2-mercapto- or 2- alkylthio-6-cyclopropyl-pyrimidin-4-ol optionally bearing a 5-alkyl or alkoxy group, which are converted into 2-chloro or 2-alkylsulphonyl compounds analogously to as described above. Compounds of Formula III wherein A 2 is a direct bond, Z is alkylsulphonyl or chlorine, one of R 2 and R 3 is cyclopropyl, the other and R 1 being hydrogen or alkyl, are made by condensing a compound of Formula VI above or an acetal, enol ether, enamine or ketal thereof with thiourea or an S-alkyl isourea to form a 2- mercapto or alkylthio- 5 or 6-cyclopropylpyrimidine optionally bearing an alkyl group at position 4 or 6 which is converted into a 2- alkylsulphonyl compound as described above, the 2-chloro compounds being obtained from the 2-mercapto compounds via the 2-hydroxy compounds. Compounds of Formula III wherein A 2 is imino and Z is hydrogen are prepared either by reacting 2-alkylsulphonyl pyrimidines described above with ammonia, or by reacting guanidine with alkyl esters of cyclopropyl malonic acid or #-oxo-#-cyclopropyl-propionic acid optionally bearing an [alpha]-alkyl or alkoxy group, to form a 2-amino- 5 or 6-cyclopropyl-pyrimidine-4-ol possibly with a 5-alkyl or alkoxy group, which is converted into the corresponding 4-chloro, 4- alkoxy, or 4-alkylthio compound. The preparation of compounds of Formula III wherein A 2 is imino and Z is nitro or cyano is also described. Diketones of Formula VI are prepared by reacting cyclopropyl methyl ketone with an ester of an alkane carboxylic acid. 1-Cyclopropyl-3-dimethylamino-prop-2-en-1-one is prepared from cyclopropyl methyl ketone and bisdimethylamino methoxymethane. Pharmaceutical compositions suitable for oral or parenteral administration in the treatment of infections by gram positive and gram negative bacteria comprise a compound of Formula I or acceptable salt thereof and at least one inert carrier.
ES338265A 1966-03-21 1967-03-20 New sulphanilamide derivatives Expired ES338265A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH407066 1966-03-21

Publications (1)

Publication Number Publication Date
ES338265A1 true ES338265A1 (en) 1968-05-01

Family

ID=4269249

Family Applications (3)

Application Number Title Priority Date Filing Date
ES338264A Expired ES338264A1 (en) 1966-03-21 1967-03-20 New sulphanilamide derivatives
ES338265A Expired ES338265A1 (en) 1966-03-21 1967-03-20 New sulphanilamide derivatives
ES338263A Expired ES338263A1 (en) 1966-03-21 1967-03-20 New sulphanilamide derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES338264A Expired ES338264A1 (en) 1966-03-21 1967-03-20 New sulphanilamide derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES338263A Expired ES338263A1 (en) 1966-03-21 1967-03-20 New sulphanilamide derivatives

Country Status (7)

Country Link
AT (1) AT268292B (en)
BE (1) BE695790A (en)
ES (3) ES338264A1 (en)
FR (1) FR6676M (en)
GB (1) GB1136686A (en)
GR (1) GR36363B (en)
NL (1) NL6704127A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8389534B2 (en) * 2008-05-19 2013-03-05 The University Of Tennessee Research Foundation Pyrimidine non-classical cannabinoid compounds and related methods of use

Also Published As

Publication number Publication date
AT268292B (en) 1969-02-10
GB1136686A (en) 1968-12-11
FR6676M (en) 1969-02-03
ES338264A1 (en) 1968-06-16
NL6704127A (en) 1967-09-22
ES338263A1 (en) 1968-06-16
GR36363B (en) 1969-02-04
BE695790A (en) 1967-09-20

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