GB835390A - New orally-effective antidiabetic compounds - Google Patents

New orally-effective antidiabetic compounds

Info

Publication number
GB835390A
GB835390A GB25918/58A GB2591858A GB835390A GB 835390 A GB835390 A GB 835390A GB 25918/58 A GB25918/58 A GB 25918/58A GB 2591858 A GB2591858 A GB 2591858A GB 835390 A GB835390 A GB 835390A
Authority
GB
United Kingdom
Prior art keywords
urea
sulphonyl
converting
isocyanate
amino group
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
GB25918/58A
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.)
Roche Diagnostics GmbH
Original Assignee
Boehringer Mannheim GmbH
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 Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Publication of GB835390A publication Critical patent/GB835390A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

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

Abstract

The invention comprises metanilyl ureas of the formula <FORM:0835390/IV (b)/1> wherein R is an alkyl or cycloalkyl radical, e.g. n-butyl, 2-pentyl or cyclohexyl, and their preparation by the following methods: (a) treating a benzene sulphonamide of the formula <FORM:0835390/IV (b)/2> or an alkali-metal salt thereof, in which W is a nitro or acylamino group with a carbamoyl chloride Cl-CO-NHR and W is then converted into an amino group by reduction or hydrolysis; (b) reacting (I) or its alkali-metal salt with an isocyanate RNCO or a compound which is converted to such an isocyanate under the reaction conditions, and subsequently converting W into an amino group; (c) reacting a benzene sulphonyl isocyanate <FORM:0835390/IV (b)/3> with an amine RNH2 and then converting W into an amino group; (d) reacting a compound which is converted into the sulphonyl isocyanate (II) under the reaction conditions such as a sulphonyl urethane or sulphonyl urea, especially a bis-sulphonyl urea, e.g. di-(acetylmetanilyl)-urea with an amine RNH2, the amine being preferably present at the commencement of the reaction to react with the isocyanate as soon as it is formed, and then converting W into an amino group; (e) reacting a benzenesulphonyl chloride, meta-substituted by the group W, with an isourea alkyl ether H2N C(OR11)NR wherein R11 is an alkyl radical, decomposing the resulting metanilyl isourea with an hydrogen halide and then converting W into an amino group; (f) converting a benzenesulphonyl guanidine W.C6H4.SO2.NH C( : NH).NHR into the corresponding sulphonyl urea by alkaline hydrolysis and then converting W into an amino group, and (g) converting a thiourea W.C6H4.SO2.NH.CS.NHR into the corresponding sulphonyl urea by oxidation. In the above process, benzene sulphinyl or sulphenyl compounds may be used in place of the benzenesulphonyl compounds and the resultant sulphinyl or sulphenyl ureas may be oxidized to the benzenesulphonyl compounds. N1 - Di - acetylmetanilyl - N2 - n - butyl urea is made by treating di-(acetylmetanilyl)-urea (obtained from acetyl metanilic amide and phosgene) with n-butylamine and heating the resulting n-butylamine salt. N1 - Acetylmetanilyl - N2 - cyclohexyl urea is made by treating acetyl metanilic amide with ethyl chloroformate and treating the resulting ethyl acetylmetanilyl-carbamate with cyclohexylamine. N1 - (m - nitrobenzene - sulphonyl) - N2 - (n-butyl)-urea is made by treating m-nitrobenzene sulphonamide with n-butyl isocyanate.
GB25918/58A 1957-08-13 1958-08-12 New orally-effective antidiabetic compounds Expired GB835390A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0045676 1957-08-13

Publications (1)

Publication Number Publication Date
GB835390A true GB835390A (en) 1960-05-18

Family

ID=6967700

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25918/58A Expired GB835390A (en) 1957-08-13 1958-08-12 New orally-effective antidiabetic compounds

Country Status (5)

Country Link
AT (1) AT216008B (en)
BE (1) BE570228A (en)
CH (1) CH366526A (en)
DK (2) DK90602C (en)
GB (1) GB835390A (en)

Also Published As

Publication number Publication date
DK94132C (en) 1962-08-20
CH366526A (en) 1963-01-15
DK90602C (en) 1961-03-20
AT216008B (en) 1961-07-10
BE570228A (en) 1958-08-30

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