GB1263561A - New sulphanilamide derivatives, their production and compositions containing same - Google Patents

New sulphanilamide derivatives, their production and compositions containing same

Info

Publication number
GB1263561A
GB1263561A GB03513/69A GB1351369A GB1263561A GB 1263561 A GB1263561 A GB 1263561A GB 03513/69 A GB03513/69 A GB 03513/69A GB 1351369 A GB1351369 A GB 1351369A GB 1263561 A GB1263561 A GB 1263561A
Authority
GB
United Kingdom
Prior art keywords
butyl
tert
diamine
compounds
propionamide
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
GB03513/69A
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
Priority claimed from CH388168A external-priority patent/CH504443A/en
Priority claimed from CH388368A external-priority patent/CH504444A/en
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB1263561A publication Critical patent/GB1263561A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C07D203/24—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/30—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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1,263,561. Imidazolidine derivatives. J. R. GEIGY A.G. 14 March, 1969 [14 March, 1968 (2)], No. 13513/69. Heading C2C. Novel Compounds I (including salts thereof) wherein R 1 signifies alkyl or alkenyl of at most 5 carbons or an optionally alkyl-substituted cycloalkyl or cycloalkenyl group or a cycloalkyl-alkyl or cycloalkenyl-alkyl group of at most 7 carbons and R 2 is Me or Et, are obtained: (a) by reacting a Compound II (R 3 signifies H, Me, allyl, aryldiaryl- or triarylmethyl and X signifies NH 2 or a group which can be converted into NH 2 by hydrolysis, reduction or reductive cleavage) with a reactive cyanic acid derivative; (b) by reacting a Compound III with a nitrile, R 1 NH.CN or with an alkali or alkaline earth metal salt thereof; (c) by reducing a Compound V (R 1 <SP>1</SP> signifies C 3-5 alkenyl or C 5-7 cycloalkenyl); or (d) by reacting a functional derivative of a sulphonic acid VI with an imidazoline VII (also described as the hydrobromide) Compounds II, III and VII are in general prepared by standard methods. Intermediates to Compounds I, e.g. compounds wherein in place of NH 2 in I there is an MeCONH- group may be produced by methods (a) to (d). N - Tert. butyl - (2 - benzylamino) - propionamide (also described as the hydrochloride), obtained by the interaction of benzylamine and N - tert. - butyl - 2 - chloro - propionamide, reacts with lithium aluminium hydride to afford N<SP>1</SP>- tert.-butyl-N<SP>2</SP>-benzyl-1,2-propane-diamine; the diamine is debenzylated to give N<SP>1</SP>-tert.-butyl- 1,2 - propane - diamine dihydrobromide. The following related compounds are also described: N-butyl-2-benzylamino-propionamide and -butyramide, N<SP>1</SP>-butyl-N<SP>2</SP>-benzyl-1,2-propanediamine and -1,2-butanediamine,and N<SP>1</SP>-butyl-1,2-propane diamine and -1,2-butane-diamine. N-Butyl-andbenzyl-2-chloro-propionamides are obtained by reacting 2-chloro-propionyl chloride with butyl amine or benzylamine (N-butyl-2-chloro-butyramide is similarly obtained); N-benzyl-2-tert.- butylamino -propionamide, N<SP>1</SP>-benzyl-N<SP>2</SP>-tert.- butyl-1,2-propanediamine and N<SP>2</SP>-tert.-butyl-1,2- propane diamine hydrobromide are also described. Pharmaceutical preparations showing hypoglycaemic action contain I as active-ingredient; administration may be orally or parenterally.
GB03513/69A 1968-03-14 1969-03-14 New sulphanilamide derivatives, their production and compositions containing same Expired GB1263561A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH388168A CH504443A (en) 1968-03-14 1968-03-14 Hypoglycaemic sulphanilamide derivs.
CH388368A CH504444A (en) 1968-03-14 1968-03-14 Hypoglycaemic sulphanilamide derivs.

Publications (1)

Publication Number Publication Date
GB1263561A true GB1263561A (en) 1972-02-09

Family

ID=25694076

Family Applications (1)

Application Number Title Priority Date Filing Date
GB03513/69A Expired GB1263561A (en) 1968-03-14 1969-03-14 New sulphanilamide derivatives, their production and compositions containing same

Country Status (11)

Country Link
BE (1) BE729834A (en)
BG (3) BG16747A3 (en)
DE (1) DE1912849A1 (en)
DK (1) DK125323B (en)
FR (1) FR2003885A1 (en)
GB (1) GB1263561A (en)
IE (1) IE32985B1 (en)
IL (1) IL31801A (en)
NL (1) NL6903830A (en)
NO (1) NO123805B (en)
SE (1) SE354070B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8517854D0 (en) * 1985-07-15 1985-08-21 Roussell Lab Ltd Chemical compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1224812A (en) * 1956-12-28 1960-06-27 Geigy Ag J R Novel 2-imino-1.3-di-n-heterocycles and their preparation process

Also Published As

Publication number Publication date
NL6903830A (en) 1969-09-16
SE354070B (en) 1973-02-26
FR2003885A1 (en) 1969-11-14
BG17009A3 (en) 1973-04-25
IL31801A (en) 1972-09-28
NO123805B (en) 1972-01-17
DE1912849A1 (en) 1969-10-02
IE32985B1 (en) 1974-02-06
DK125323C (en) 1973-07-23
BE729834A (en) 1969-09-15
BG16747A3 (en) 1973-02-15
BG15572A3 (en) 1976-06-21
IL31801A0 (en) 1969-05-28
IE32985L (en) 1969-09-14
DK125323B (en) 1973-02-05

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