GB1046248A - Substituted imidazoles - Google Patents

Substituted imidazoles

Info

Publication number
GB1046248A
GB1046248A GB2979162A GB2979162A GB1046248A GB 1046248 A GB1046248 A GB 1046248A GB 2979162 A GB2979162 A GB 2979162A GB 2979162 A GB2979162 A GB 2979162A GB 1046248 A GB1046248 A GB 1046248A
Authority
GB
United Kingdom
Prior art keywords
nitro
remainder
those
amino
compounds
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
GB2979162A
Inventor
Colin Fitzmaurice
George Harry Lord
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.)
BENGER LAB Ltd
Original Assignee
BENGER LAB Ltd
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 BENGER LAB Ltd filed Critical BENGER LAB Ltd
Priority to GB2979162A priority Critical patent/GB1046248A/en
Publication of GB1046248A publication Critical patent/GB1046248A/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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
    • 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/93—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by halogen atoms, attached to other ring members
    • 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
    • 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

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

Abstract

Compounds of the formula <FORM:1046248/C2/1> and/or <FORM:1046248/C2/2> and their salts, wherein R1 is H or a C1- 10-alkyl group; R2 is H, a C1- 10 alkyl, hydroxyalkyl, carboxyalkyl, esterified carboxyalkyl, dialkyl-aminoalkyl, cyanoalkyl or pyridylethyl group; R3 is H or a nitro group; R4, R5, R6, R7 and R8 are H or halogen atoms, phenyl, amino, acylamino, or nitro groups, not more than four of R4 to R8 being H and not more than one of R4 to R8 being nitro, amino, acylamino or phenyl; and n is 0 or 1; excluding those compounds where R6 is amino, acetylamino, or nitro, R3 is H or a nitro group and the remainder of R1 to R8 are H; those in which R4 or R5 are nitro, the remainder of R1 to R8 being H; those in which R6 is halogen, the remainder of R1 to R8 being H; and those in which R3, R4 or R6, or R3 and R6 are nitro groups, the remainder of R1 to R8 being H, are prepared by reacting either an appropriately substituted phenacy halide with formamide (R1, R2 and R3 in the product are H) or an appropriately substituted phenacyl alcohol or simple ester thereof with an appropriate aliphatic aldehyde and ammonia (R1 is alkyl, R2 and R3 are H), or by nitrating either of the products of the two previous processes or substituting a 1-unsubstituted imidazole derivative formed in the above processes (R2 is other than H). 2,3,4-Trichloroacetophenone is prepared from 2,3,4-trichlorobenzene and acetyl chloride. Pharmaceutical compositions comprise the compounds of the invention and a carrier therefore. The compositions, which show antiprotozoal and antifungal activity, may be in a form for oral, parenteral or topical administration.
GB2979162A 1962-08-02 1962-08-02 Substituted imidazoles Expired GB1046248A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2979162A GB1046248A (en) 1962-08-02 1962-08-02 Substituted imidazoles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2979162A GB1046248A (en) 1962-08-02 1962-08-02 Substituted imidazoles

Publications (1)

Publication Number Publication Date
GB1046248A true GB1046248A (en) 1966-10-19

Family

ID=10297215

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2979162A Expired GB1046248A (en) 1962-08-02 1962-08-02 Substituted imidazoles

Country Status (1)

Country Link
GB (1) GB1046248A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995004724A1 (en) * 1993-08-11 1995-02-16 Nippon Soda Co., Ltd. Imidazole derivative, process for producing the same, and pest control drug
US7157483B2 (en) * 2001-06-14 2007-01-02 Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) Imidazole derivatives modulating the sodium channels

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995004724A1 (en) * 1993-08-11 1995-02-16 Nippon Soda Co., Ltd. Imidazole derivative, process for producing the same, and pest control drug
US7157483B2 (en) * 2001-06-14 2007-01-02 Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) Imidazole derivatives modulating the sodium channels
US7402602B2 (en) * 2001-06-14 2008-07-22 Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S) Imidazole derivatives modulating the sodium channels

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