IE32985B1 - Process for the production of new sulphanilamide derivatives - Google Patents

Process for the production of new sulphanilamide derivatives

Info

Publication number
IE32985B1
IE32985B1 IE331/69A IE33169A IE32985B1 IE 32985 B1 IE32985 B1 IE 32985B1 IE 331/69 A IE331/69 A IE 331/69A IE 33169 A IE33169 A IE 33169A IE 32985 B1 IE32985 B1 IE 32985B1
Authority
IE
Ireland
Prior art keywords
butyl
tert
diamine
compounds
propionamide
Prior art date
Application number
IE331/69A
Other versions
IE32985L (en
Original Assignee
Ciba 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 Ciba Geigy Ag filed Critical Ciba Geigy Ag
Publication of IE32985L publication Critical patent/IE32985L/en
Publication of IE32985B1 publication Critical patent/IE32985B1/en

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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic 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. [GB1263561A]
IE331/69A 1968-03-14 1969-03-13 Process for the production of new sulphanilamide derivatives IE32985B1 (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 (2)

Publication Number Publication Date
IE32985L IE32985L (en) 1969-09-14
IE32985B1 true IE32985B1 (en) 1974-02-06

Family

ID=25694076

Family Applications (1)

Application Number Title Priority Date Filing Date
IE331/69A IE32985B1 (en) 1968-03-14 1969-03-13 Process for the production of new sulphanilamide derivatives

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
IL31801A (en) 1972-09-28
SE354070B (en) 1973-02-26
IL31801A0 (en) 1969-05-28
GB1263561A (en) 1972-02-09
BG15572A3 (en) 1976-06-21
BG16747A3 (en) 1973-02-15
BG17009A3 (en) 1973-04-25
NL6903830A (en) 1969-09-16
NO123805B (en) 1972-01-17
IE32985L (en) 1969-09-14
DE1912849A1 (en) 1969-10-02
DK125323C (en) 1973-07-23
FR2003885A1 (en) 1969-11-14
BE729834A (en) 1969-09-15
DK125323B (en) 1973-02-05

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