ES340430A1 - Benzenesulphonyl-Ureas and process for preparing them - Google Patents

Benzenesulphonyl-Ureas and process for preparing them

Info

Publication number
ES340430A1
ES340430A1 ES340430A ES340430A ES340430A1 ES 340430 A1 ES340430 A1 ES 340430A1 ES 340430 A ES340430 A ES 340430A ES 340430 A ES340430 A ES 340430A ES 340430 A1 ES340430 A1 ES 340430A1
Authority
ES
Spain
Prior art keywords
benzenesulphonyl
radical
urea
alkyl
prepared
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
ES340430A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of ES340430A1 publication Critical patent/ES340430A1/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Novel benzenesulphonyl-ureas I (including salts thereof) in which R represents an alkyl radical (C 1 to C 3 ) and may also represent a grouping derived from said radical which is bound at the oposition of the benzene nucleus to which the nitrogen atom is bound thus forming a heterocyclic ring, R1 represents: (a) an alkyl or alkenyl radical (C 3 -C 6 ), (b) an endoalkylene-cyclohexyl, endoalkylene-cyclohexenyl, endoalkylene-cyclohexylmethyl or endoalkylenecyclohexenylmethyl radical containing 1 or 2 endoalkylene carbon atoms, (c) a C 1 to C 4 alkyl-cyclohexyl or dialkyl-oyclohexyl radical, (d) a cycloalkyl radical containing 5 to 8 carbons which may be substituted by alkyl or linked to the nitrogen atom by means of alkylene, (e) a cyclohexenyl or cyclohexenylmethyl radical, or (f) a nortricyolyl or adamantyl radical, X and X1 may be the same or different and represent a hydrogen atom, alkyl or alkoxy radical or halogen atom or when X is hydrogen X1 may also be a -CF 3 or -NO 2 group or X and X1 may together represent a methylenedioxy group and Y represents a hydrocarbon straight or branched chain containing 2 or 3 carbons, are prepared: (a) by the interaction of an amine, R1NH 2 , or salt thereof and a benzenesulphonyl-isocyanate, -carbamic acid ester, -thiolcarbamic acid ester, -urea, -semicarbazide or -carbazone which is substituted at the 4-position by the Group II (b) by the interaction of a corresponding benzenesulphonamide (prepared by acylating the appropriate amino-alkylbenzene-sulphonamide) substituted at the 4-position by the Group II and an R1-substituted isocyanate, carbamic acid ester, thiolcarbamic acid ester, carbamic acid halide or urea, (c) by hydrolysis of compounds comprising the above group attached at -Y- to the 4-position of a benzenesulphonylisourea ether, -isothiourea ether, -haloformic acid amidine or -parabamic acid, (d) by replacement of the thiocarbonyl sulphur atom in the corresponding benzenesulphonylthioureas by an oxygen atom, (e) by hydrogenating the corresponding benzenesulphonylureas containing unsaturation, or (f) by acylating a benzene-sulphonyl-urea of the formula N- [4 - (# -Indolino - carbamoylethyl ) benzenesulphonyl]-urea and N-[4-(#-<N-phenyl-N-methylureido> -ethyl) benzenesulphonyl]-urea are prepared by the interaction of the corresponding benzenesulphonamide and potassiumisocyanate. N.[4.-(#-Indolino-carbamoylethyl) benzenesulphonyl] - N1 - (2,5 - endomethylene - cyclohexylmethyl)-thiourea and N-[4-(#- <N-methyl-N- phenyl - ureido> ethyl) - benzenesulphonyl]-N1- cyclohexyl-thiourea are prepared by the interaction of the corresponding benzenesulphonamide and 2,5-endomethylene-cyclohexylmethyl isothiocyanate or cyclohexyl isothiocyanate respectively. N - [4 - (# - Indolinocarbamoylethyl) benzenesulphonyl] - N1 - (2,5 - endomethylene-cyclohexylmethyl) - isoureamethylether is obtained by treating the above corresponding thiourea with HgO(MeOH. 4 - [# - (N - 4 - Chlorophenyl - - N - methyl - ureido) ethyl]-benzenesulphonyl-methyl-urethane is prepared from the corresponding benzenesulphonamide and methyl chloroformate. Pharmaceutical preparations having hypoglycaemic activity comprise compounds I in admixture or conjunction with a carrier, preferably in a form adapted to oral administration, e.g. tablets.
ES340430A 1966-05-14 1967-05-11 Benzenesulphonyl-Ureas and process for preparing them Expired ES340430A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1966F0049207 DE1670700B2 (en) 1966-05-14 1966-05-14 Benzenesulfonylureas, process for their preparation and their use

Publications (1)

Publication Number Publication Date
ES340430A1 true ES340430A1 (en) 1968-06-01

Family

ID=7102821

Family Applications (1)

Application Number Title Priority Date Filing Date
ES340430A Expired ES340430A1 (en) 1966-05-14 1967-05-11 Benzenesulphonyl-Ureas and process for preparing them

Country Status (13)

Country Link
AT (2) AT326683B (en)
BE (1) BE698498A (en)
CH (1) CH491878A (en)
DE (1) DE1670700B2 (en)
DK (1) DK130679B (en)
ES (1) ES340430A1 (en)
FI (1) FI45962C (en)
FR (1) FR6904M (en)
GB (1) GB1185395A (en)
LU (1) LU53629A1 (en)
NL (1) NL152256B (en)
NO (1) NO122417B (en)
SE (1) SE335126B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MTP848B (en) * 1978-06-27 1980-06-24 Hoechst Ag Sulfonyl ureas process for their manufacture pharmaceutical preparation on the basis of there compounds and their use
DE2951135A1 (en) * 1979-12-19 1981-06-25 Hoechst Ag, 6230 Frankfurt SULFONYL UREAS, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICAL PREPARATIONS BASED ON THESE COMPOUNDS AND THEIR USE
DE69632402T2 (en) * 1995-06-30 2005-05-19 Zymogenetics, Inc., Seattle 4- (2- (N - (- 2-CARBOXAMIDOINDOLE) AMINIETHYL) -BENZENESULFONAMIDE OR SULPHONYL HARVES AS PDGF ANTAGONIST
HRP20090186A2 (en) 2009-03-31 2010-10-31 Institut Ruđer Bošković Adamantane bisurea derivates, method of their preparation and application in anion sensing

Also Published As

Publication number Publication date
NO122417B (en) 1971-06-28
DE1670700A1 (en) 1970-11-12
GB1185395A (en) 1970-03-25
NL152256B (en) 1977-02-15
ATA382974A (en) 1975-03-15
SE335126B (en) 1971-05-17
BE698498A (en) 1967-11-16
AT326683B (en) 1975-12-29
FR6904M (en) 1969-04-28
DK130679B (en) 1975-03-24
DK130679C (en) 1975-08-25
FI45962B (en) 1972-07-31
NL6706679A (en) 1967-11-15
AT323190B (en) 1975-06-25
DE1670700B2 (en) 1978-06-22
FI45962C (en) 1972-11-10
LU53629A1 (en) 1969-02-10
CH491878A (en) 1970-06-15

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