GB863451A - New sulphonyl-ureas and preparations containing them - Google Patents

New sulphonyl-ureas and preparations containing them

Info

Publication number
GB863451A
GB863451A GB34894/59A GB3489459A GB863451A GB 863451 A GB863451 A GB 863451A GB 34894/59 A GB34894/59 A GB 34894/59A GB 3489459 A GB3489459 A GB 3489459A GB 863451 A GB863451 A GB 863451A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
benzenesulphonyl
radical
methyl
ureas
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
GB34894/59A
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 GB863451A publication Critical patent/GB863451A/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
    • 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
    • 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
    • C07D295/12—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 singly or doubly bound nitrogen atoms
    • 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
    • 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

Landscapes

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

Abstract

The invention comprises benzenesulphonylureas of the formula R1SO2NH,CO,NR2R3 and salts thereof, wherein R1 is a phenyl radical bearing one or two alkyl, alkoxy or halogen substituents e.g. methyl, ethyl, methoxy or chloro, R2 is an aliphatic hydrocarbon radical of 1-4 carbon atoms, an alicyclic hydrocarbon radical of 5-7 carbon atoms or a benzyl or phenethyl radical and R3 is an aliphatic hydrocarbon radical of 1-4 carbon atoms, R2 and R3 together containing at least 3 carbon atoms, or R2 and R3 together with the nitrogen atom form a saturated heterocyclic ring system comprising at most 7 carbon atoms. The products are made by known methods for the production of sulphonyl ureas for example benzenesulphonylcarbamic esters or halides or benzenesulphonyl isocyanates or compounds convertible to benzenesulphonyl isocyanates under the reaction conditions are treated with amines HNR2R3 or benzenesulphonamides are reacted with N:N-di-substituted carbamic halides or urethanes or other compounds yielding the residue -NHCONR2R3. Also benzenesulphonyl-isourea ethers and benzenesulphonyl-thioureas may be converted into the desired benzenesulphonyl ureas by hydrolyses or oxidation. The compounds are used pharmaceutically as anti-diabetic agents (see Group VI). Many products are exemplified in which R1 is a p-methylphenyl, p-chlorophenyl, p-ethylphenyl, p-methoxyphenyl or m-chloro-p-methyl-phenyl radical and NR2R3 is a pyrrolidino, diethylamino, piperidino, methylcyclohexylamino, methylethylamino, hexamethyleneamino, dipropylamino, dibutylamino, methylbenzylamino, ethylpropylamino, ethylbutylamino, ethylcyclohexylamino or 1 : 1-dimethyl-trimethyleneimino radical. 4-Chlorobenzenesulphonyl isocyanate and 3-chloro-4-methyl-benzenesulphonyl isocyanate used as intermediates are made by treating the corresponding benzenesulphonamides with phosgene. N-Benzenesulphonyl - N1 - acetyl - ureas such as N- pmethyl, p-ethyl- and p-chlorobenzenesulphonyl-N1-acetyl ureas are made by treating the corresponding benzenesulphonylureas with acetic anhydride and sulphuric acid. Methyl p-methoxybenzenesulphonylcarbamate is made by the action of methyl chloroformate on p-methoxybenzenesulphonamide.ALSO:Preparations for oral treatment of diabetes comprise compounds of the formula R1SO2NHCONR2R3 or salts thereof, wherein R1 is a phenyl radical bearing one or two alkyl, alkoxy or halogen substituents, e.g. methyl, ethyl, methoxy or chloro, R2 is an aliphatic hydrocarbon radical of 1-4 carbon atoms, an alicyclic hydrocarbon radical of 5-7 carbon atoms or a benzyl or phenethyl radical and R3 is an aliphatic hydrocarbon radical of 1-4 carbon atoms, R2 and R3 together containing at least 3 carbon atoms, or R2 and R3 together with the nitrogen atom form a saturated heterocyclic ring (see Group IV (b)) in admixture or conjunction with a pharmaceutically suitable carrier. The preparations may take the form of pills, capsules, cachets, mixtures, solutions, powders or more particularly tablets in which the active constituent, e.g. N - p - tolylsulphonyl - N1 : N1-tetramethylene urea, is admixed with such diluents as starch, lactose, talc, tragacanth and magnesium stearate.
GB34894/59A 1958-10-14 1959-10-14 New sulphonyl-ureas and preparations containing them Expired GB863451A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF26804A DE1157599B (en) 1958-10-14 1958-10-14 Process for the preparation of sulfonylureas

Publications (1)

Publication Number Publication Date
GB863451A true GB863451A (en) 1961-03-22

Family

ID=7092170

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34894/59A Expired GB863451A (en) 1958-10-14 1959-10-14 New sulphonyl-ureas and preparations containing them

Country Status (6)

Country Link
BE (1) BE583616A (en)
CH (3) CH395058A (en)
DE (1) DE1157599B (en)
FR (6) FR1312411A (en)
GB (1) GB863451A (en)
NL (1) NL244329A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4448491A2 (en) * 2021-12-16 2024-10-23 The United States of America, as represented by the Secretary, Department of Health and Human Services N-((adamantan-1-yl)carbamoyl)-benzenesulfonamide derivatives as soluble epoxide hydrolase inhibitors for the treatment of hypertension

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1003716B (en) * 1956-01-07 1957-03-07 Hoechst Ag Process for the preparation of new benzenesulfonylureas

Also Published As

Publication number Publication date
DE1157599B (en) 1963-11-21
FR544M (en) 1961-05-29
FR1312411A (en) 1962-12-21
FR546M (en) 1961-05-29
FR545M (en) 1961-05-29
BE583616A (en)
CH385818A (en) 1964-12-31
FR548M (en) 1961-05-29
FR547M (en) 1961-05-29
CH395059A (en) 1965-07-15
CH395058A (en) 1965-07-15
NL244329A (en) 1964-01-27

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