GB929054A - Improvements in and relating to heterocyclic compounds and the manufacture thereof - Google Patents

Improvements in and relating to heterocyclic compounds and the manufacture thereof

Info

Publication number
GB929054A
GB929054A GB474062A GB474062A GB929054A GB 929054 A GB929054 A GB 929054A GB 474062 A GB474062 A GB 474062A GB 474062 A GB474062 A GB 474062A GB 929054 A GB929054 A GB 929054A
Authority
GB
United Kingdom
Prior art keywords
reacting
benzenesulphonyl
amino
piperidino
piperidine
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
GB474062A
Inventor
John Brenton Wright
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Priority to GB474062A priority Critical patent/GB929054A/en
Priority to FR888647A priority patent/FR1492759A/en
Publication of GB929054A publication Critical patent/GB929054A/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
    • C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues

Landscapes

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

Abstract

The invention comprises benzenesulphonyl ureas of the formula <FORM:0929054/IV(a)/1> wherein X and X1 are hydrogen, halogen, e.g. Cl, Br or F, or C1-4 alkyl or alkoxy groups, R is hydrogen or a C1-4 alkyl group and R1 is a C1-4 alkyl group and pharmacologically acceptable acid addition salts thereof; and their preparation by (a) reacting a benzenesulphonyl-urethane with a 1-aminopiperidine; (b) reacting a benzenesulphonylisocyanate with a 1-amino-piperidine; (c) reacting a benzenesulphonyl-urea with a 1-amino-piperidine; (d) reacting a benzenesulphonyl-carbamic halide with a 1-aminopiperidine; (e) reacting a benzenesulphonamide or an alkali-metal salt thereof with a piperidino-isocyanate; (f) reacting a benzenesulphonamide or an alkali-metal salt thereof with a piperidino-carbamoyl halide; (g) reacting an O-methyl-piperidino-isourea with a benzenesulphonyl halide and hydrolysing the resulting product; (h) reacting a benzenesulphonyl-cyanamide with a 1-amino-piperidine and hydrolysing the resulting guanidine; (i) reacting an alkali-metal salt of a benzenesulphonamide with a piperidino-isothiocyanate and oxidising the resulting thiourea or (j) reacting a piperidinourethane with an aryl sulphonamide. The products may be converted into their salts with acids such as hydrochloric, hydrobromic sulphuric, phospheric, tartaric, acetic, citric, succinic, maleic, benzoic and salicylic. Starting materials. 1-Amino-4-alkylpiperidines and 1-amino-4,4-dialkylpiperidines are made by treating the appropriate piperidine with nitrous acid and reducing the resulting 1-nitroso-4-alkyl (or 4,4-dialkyl)-piperidine. 4-Methyl-piperidino-isocyanate is prepared from 1-amino-4-methylpiperidine and phosgene. Pharmaceutical preparations, suitable for the treatment of diabetes, comprise the above compounds of the invention in admixture with a pharmaceutical carrier, preferably for oral administration, but also if desired for intravenous administration in a liquid carrier. The preparations may suitably take the form of capsules, tablets, powders, pills, solutions and suspensions. Specification 808,071 is referred to.
GB474062A 1962-02-07 1962-02-07 Improvements in and relating to heterocyclic compounds and the manufacture thereof Expired GB929054A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB474062A GB929054A (en) 1962-02-07 1962-02-07 Improvements in and relating to heterocyclic compounds and the manufacture thereof
FR888647A FR1492759A (en) 1962-02-07 1962-10-20 Production of new nu-arylsulfonyl-nu'-piperidinoureas

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB474062A GB929054A (en) 1962-02-07 1962-02-07 Improvements in and relating to heterocyclic compounds and the manufacture thereof

Publications (1)

Publication Number Publication Date
GB929054A true GB929054A (en) 1963-06-19

Family

ID=9782893

Family Applications (1)

Application Number Title Priority Date Filing Date
GB474062A Expired GB929054A (en) 1962-02-07 1962-02-07 Improvements in and relating to heterocyclic compounds and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB929054A (en)

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