GB1026409A - New imidazole derivatives and processes for their production - Google Patents

New imidazole derivatives and processes for their production

Info

Publication number
GB1026409A
GB1026409A GB2395763A GB2395763A GB1026409A GB 1026409 A GB1026409 A GB 1026409A GB 2395763 A GB2395763 A GB 2395763A GB 2395763 A GB2395763 A GB 2395763A GB 1026409 A GB1026409 A GB 1026409A
Authority
GB
United Kingdom
Prior art keywords
reacting
alkyl
phenyl
methyl
iii
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
GB2395763A
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
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB1026409A publication Critical patent/GB1026409A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/90—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
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/70—One oxygen atom
    • 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
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/84—Sulfur atoms

Landscapes

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

Abstract

The invention comprises imidazoles of the general formula <FORM:1026409/C2/1> and the non-toxic salts with inorganic or organic acids, wherein R is -OH or -SH; R1 is H, methyl, carboxy or carbalboxy; R2 is C1- 10-alkyl, C2- 6-alkenyl, C3- 7-cycloalkyl, o , o -dialkoxyalkyl (at most 6C), dialkylamino alkyl (in all at most 10C and wherein the two alkyl groups together with N can form a 5-7 membered ring), phenyl, phenylalkyl (at most 4C in the alkylene residue) the phenyl group being optionally substituted by halogen, OH, CN, NO2, CF3, CO2H, CH3CO2, CO2C2H5, alkylthio, alkanoyl (at most 4C) or 1-3 alkyl or alkoxy groups (at most 4C in each radical) and the preparation thereof (wherein R is OH) by reacting HCHO, and amine R2NH2 and a ketone <FORM:1026409/C2/2> wherein R11 is methyl or carbalkoxy in a polar solvent, or first forming the Schiffs base and reacting this with III; or (wherein R is SH) by reacting HCHO, R2NH2 and III in a polar solvent, with a reactant which gives off the hydrosulphide ion; or (wherein R is OA and R1 is H) by reacting an isocyanate R2NCO with an alkanol <FORM:1026409/C2/3> and oxidizing the reaction product, e.g. Opponauer reaction. 1 -(N-phenyl-N1-ureido)-propanol-(2) is prepared from 2-hydroxypropylamine and PhNCO. Pharmaceutical compositions comprise compounds I (or their salts) and a pharmaceutically acceptable carrier therefor. The compositions, which possess analgetic, central nervous system depressant, antipyretic and anti-inflammatory activity may be formulated as tablets, dragees, suppositories or solutions for injection.
GB2395763A 1962-06-22 1963-06-17 New imidazole derivatives and processes for their production Expired GB1026409A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US20464362A 1962-06-22 1962-06-22

Publications (1)

Publication Number Publication Date
GB1026409A true GB1026409A (en) 1966-04-20

Family

ID=22758808

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2395763A Expired GB1026409A (en) 1962-06-22 1963-06-17 New imidazole derivatives and processes for their production

Country Status (11)

Country Link
AT (1) AT236947B (en)
BE (1) BE633977A (en)
CH (3) CH427825A (en)
DE (2) DE1203269B (en)
DK (2) DK104741C (en)
ES (3) ES289662A1 (en)
FI (2) FI44238B (en)
FR (1) FR1367746A (en)
GB (1) GB1026409A (en)
NL (1) NL294421A (en)
SE (2) SE318884B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2732531A1 (en) * 1977-07-19 1979-02-01 Hoechst Ag IMIDAZOLE CARBONIC ACIDS AND THEIR DERIVATIVES
PH19153A (en) * 1981-11-04 1986-01-15 Merrell Dow Pharma Treatment of cardiac failure using imidazolecarboxylic acid derivatives
GB8516573D0 (en) * 1985-07-01 1985-08-07 Janssen Pharmaceuticaa Nv Controlling weeds
US5616601A (en) * 1994-07-28 1997-04-01 Gd Searle & Co 1,2-aryl and heteroaryl substituted imidazolyl compounds for the treatment of inflammation
US6613789B2 (en) 1994-07-28 2003-09-02 G. D. Searle & Co. Heterocyclo-substituted imidazoles for the treatment of inflammation

Also Published As

Publication number Publication date
ES289662A1 (en) 1963-10-16
DK104741C (en) 1966-06-27
BE633977A (en) 1963-12-23
FR1367746A (en) 1964-07-24
CH427825A (en) 1967-01-15
DE1203269B (en) 1965-10-21
FI44239B (en) 1971-06-30
ES289663A1 (en) 1963-10-16
DK105469C (en) 1966-10-03
FI44238B (en) 1971-06-30
ES289661A1 (en) 1963-10-16
SE318884B (en) 1969-12-22
CH426852A (en) 1966-12-31
CH427824A (en) 1967-01-15
SE318883B (en) 1969-12-22
NL294421A (en)
DE1203270B (en) 1965-10-21
AT236947B (en) 1964-11-25

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