GB1270810A - Nitroimidazole derivatives - Google Patents

Nitroimidazole derivatives

Info

Publication number
GB1270810A
GB1270810A GB3270369A GB3270369A GB1270810A GB 1270810 A GB1270810 A GB 1270810A GB 3270369 A GB3270369 A GB 3270369A GB 3270369 A GB3270369 A GB 3270369A GB 1270810 A GB1270810 A GB 1270810A
Authority
GB
United Kingdom
Prior art keywords
alkyl
compound
nitro
formula
group
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
GB3270369A
Inventor
William James Ross
William Boffey Jamieson
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.)
Lilly Industries Ltd
Original Assignee
Lilly Industries 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 Lilly Industries Ltd filed Critical Lilly Industries Ltd
Priority to IL32760A priority Critical patent/IL32760A0/en
Priority to US847406A priority patent/US3658797A/en
Priority to BE737093D priority patent/BE737093A/xx
Priority to NL6911939A priority patent/NL6911939A/xx
Priority to IE1091/69A priority patent/IE33544B1/en
Priority to CA058,622A priority patent/CA939342A/en
Priority to CH763572A priority patent/CH550805A/en
Priority to CH1191269A priority patent/CH543517A/en
Priority to FR6927079A priority patent/FR2015181A1/fr
Priority to AT759669A priority patent/AT306714B/en
Priority to SE6910995A priority patent/SE372013B/xx
Priority to DE19691940045 priority patent/DE1940045A1/en
Priority to OA53704A priority patent/OA03610A/en
Publication of GB1270810A publication Critical patent/GB1270810A/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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • 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

Abstract

1,270,810. Nitroimidazole derivatives. LILLY INDUSTRIES Ltd. 6 Aug., 1969 [6 Aug., 1968; 9 Sept., 1968; 27 June, 1969], Nos. 37562/68, 42784/68 and 32703/69. Heading C2C. Novel compounds of Formula I wherein R is either: (i) phenyl optionally substituted by from 1 to 3 groups, which may be the same or different, selected from alkyl, cycloalkyl, phenyl, alkoxy, halogen, trifluoromethyl, nitro, amino, dialkylamino; aminoalkyl in which the amino nitrogen optionally forms part of a heterocyclic ring; carboxy and salts, esters and amides thereof; hydroxymethyl and esters thereof with alkanoic acids; or formyl and its acetals and thioacetals (open or cyclic), oximes, oxime ethers, semicarbazones, thiosemicarbazones, anils, and hydrazones such as those formed with phenylhydrazine, N-aminomorpholine and N-aminohydantoin; (ii) naphthyl optionally substituted by alkyl or alkoxy; or (iii) a heterocyclic ring selected from those having the Formulµ II to VIII wherein R<SP>3</SP> and R<SP>4</SP> are independently hydrogen or alkyl of 1 to 4 carbon atoms, and R<SP>1</SP> and R<SP>2</SP> are independently hydrogen, alkyl, phenylalkyl, halogen, trifluoromethyl, nitro, amino or dialkylamino; and X is the group -CR<SP>a</SP>=CHR<SP>b</SP> and additionally, when R is not unsubstituted phenyl, unsubstituted furyl, halophenyl or tolyl, X is the group -CHR<SP>a</SP>-CHR<SP>b</SP>-OR<SP>c</SP> where R<SP>a</SP> and R<SP>b</SP> are independently hydrogen or alkyl and R<SP>c</SP> is hydrogen, alkyl or a good leaving group, e.g. acyl or sulphonyl; any alkyl or alkylcontaining group in the above defined substituents, unless otherwise stated, having no more than 8 carbons, are prepared by reacting a compound of Formula IX in the presence of a strong base with an aldehyde of formula RCHO, and optionally subjecting a resulting compound to one or more of the following reactions: (a) when R<SP>c</SP> is H, converting Re to a good leaving group by reaction with the acid chloride of the good leaving group, (b) when R<SP>c</SP> is a good leaving group, reacting the compound with a strong base to produce the corresponding compound in which X is CR<SP>a</SP>=CH<SP>b</SP>, and (c) converting the substituent R to another substituent within the values of R. 2-Methyl-5-nitro-1-vinylimidazole is prepared by reacting 2 - methy 1- 5 - nitro - imidazole - 1- ethanol with p-toluene-sulphonyl chloride and treating the resulting tosylate with sodium in ethanol. Pharmaceutical compositions having antiparasitic activity comprise a compound of Formula I and a pharmaceutically acceptable carrier.
GB3270369A 1968-08-06 1968-08-06 Nitroimidazole derivatives Expired GB1270810A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
IL32760A IL32760A0 (en) 1968-08-06 1969-08-03 5-nitro-imidazole derivatives
US847406A US3658797A (en) 1968-08-06 1969-08-04 Novel 5-nitroimidazole antiparasitic agents
BE737093D BE737093A (en) 1968-08-06 1969-08-05
NL6911939A NL6911939A (en) 1968-08-06 1969-08-05
IE1091/69A IE33544B1 (en) 1968-08-06 1969-08-05 Nitroimidazole derivatives
CA058,622A CA939342A (en) 1968-08-06 1969-08-05 Heterocyclic compounds
CH763572A CH550805A (en) 1968-08-06 1969-08-05 PROCESS FOR THE PREPARATION OF NEW CHEMICAL ANTIPEST COMPOUNDS.
CH1191269A CH543517A (en) 1968-08-06 1969-08-05 Process for the preparation of new chemical antiparasitic compounds
FR6927079A FR2015181A1 (en) 1968-08-06 1969-08-06
AT759669A AT306714B (en) 1968-08-06 1969-08-06 Process for the preparation of new nitroimidazole derivatives
SE6910995A SE372013B (en) 1968-08-06 1969-08-06
DE19691940045 DE1940045A1 (en) 1968-08-06 1969-08-06 Heterocyclic compounds
OA53704A OA03610A (en) 1968-09-09 1969-08-11 Process for the preparation of new chemical compounds endowed with parasitocidal properties.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3756268 1968-08-06

Publications (1)

Publication Number Publication Date
GB1270810A true GB1270810A (en) 1972-04-19

Family

ID=10397402

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3270369A Expired GB1270810A (en) 1968-08-06 1968-08-06 Nitroimidazole derivatives

Country Status (1)

Country Link
GB (1) GB1270810A (en)

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