GB1528639A - 1-(2-aryl-1,3-dioxolan-2-yl methyl)-1h-imidazoles methods for their preparation and compositions containing them - Google Patents

1-(2-aryl-1,3-dioxolan-2-yl methyl)-1h-imidazoles methods for their preparation and compositions containing them

Info

Publication number
GB1528639A
GB1528639A GB846/76A GB84676A GB1528639A GB 1528639 A GB1528639 A GB 1528639A GB 846/76 A GB846/76 A GB 846/76A GB 84676 A GB84676 A GB 84676A GB 1528639 A GB1528639 A GB 1528639A
Authority
GB
United Kingdom
Prior art keywords
dioxolan
imidazoles
aryl
methyl
preparation
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
GB846/76A
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.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica NV
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 US05/544,157 external-priority patent/US3936470A/en
Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Priority claimed from US05/732,826 external-priority patent/US4101666A/en
Publication of GB1528639A publication Critical patent/GB1528639A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
    • C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
    • C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/16—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

Novel 1,3-dioxolan-2-ylmethylimidazoles of the general formula I <IMAGE> where the substituents are defined in claim 1, their salts with acids and the optical isomers are obtained by reacting a reactive ketal of the formula II with imidazole of the formula III or a metal salt thereof in an organic solvent and, if appropriate, converting the resulting compounds of the general formula I into their salts using an acid. The compounds of the general formula I which can be prepared according to the invention are used as active ingredients in biocides.
GB846/76A 1975-01-27 1976-01-09 1-(2-aryl-1,3-dioxolan-2-yl methyl)-1h-imidazoles methods for their preparation and compositions containing them Expired GB1528639A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US05/544,157 US3936470A (en) 1975-01-27 1975-01-27 1,3-Dioxolan-2-ylmethylimidazoles
US61986375A 1975-10-06 1975-10-06
US71099476A 1976-08-02 1976-08-02
US05/732,826 US4101666A (en) 1975-10-06 1976-10-15 1-(2-Ar-4-R-1,3-dioxolan-2-ylmethyl)imidazoles
US05/732,828 US4101664A (en) 1975-10-06 1976-10-15 1-(2-Ar-4-aryloxymethyl-1,3-dioxolan-2-ylmethyl)-imidazoles

Publications (1)

Publication Number Publication Date
GB1528639A true GB1528639A (en) 1978-10-18

Family

ID=27541875

Family Applications (1)

Application Number Title Priority Date Filing Date
GB846/76A Expired GB1528639A (en) 1975-01-27 1976-01-09 1-(2-aryl-1,3-dioxolan-2-yl methyl)-1h-imidazoles methods for their preparation and compositions containing them

Country Status (8)

Country Link
JP (1) JPS6135196B2 (en)
AU (1) AU503981B2 (en)
CA (1) CA1065873A (en)
CH (1) CH626361A5 (en)
DE (1) DE2602770A1 (en)
FR (1) FR2298328A1 (en)
GB (1) GB1528639A (en)
NL (1) NL181906C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0049565A2 (en) * 1980-08-25 1982-04-14 Syntex (U.S.A.) Inc. Derivatives of substituted N-alkylimidazoles, their preparation and pharmaceutical compositions containing them
EP0052905A1 (en) * 1980-11-24 1982-06-02 Janssen Pharmaceutica N.V. Novel (2-aryl-4-phenylthioalkyl-1,3-dioxolan-2-yl-methyl)azole derivatives

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4160841A (en) * 1977-01-31 1979-07-10 Janssen Pharmaceutica, N.V. Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
US4144346A (en) * 1977-01-31 1979-03-13 Janssen Pharmaceutica N.V. Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
CH637392A5 (en) * 1978-07-24 1983-07-29 Janssen Pharmaceutica Nv 2-Phenyl-2-azolylmethyl-cyclohexa(d)-1,3-dioxolane derivatives, processes for their preparation, compositions containing these active substances as microbicides, and their use
CH634842A5 (en) * 1978-07-25 1983-02-28 Janssen Pharmaceutica Nv 2-Phenyl-2-(1(H)-imidazolylmethyl)-1,3-dioxane derivatives, processes for their preparation, microbicides containing these active substances, and their use
US4277486A (en) * 1979-03-09 1981-07-07 Syntex (U.S.A.) Inc. 1-[(Substituted-naphthyl)ethyl]-imidazole derivatives
DE3039087A1 (en) 1980-10-16 1982-05-19 Hoechst Ag, 6000 Frankfurt 1- (1,3-DIOXOLAN-2-YLMETHYL) -AZOLES, THEIR SALTS, METHOD FOR THE PRODUCTION AND THEIR USE
DE3144318A1 (en) * 1981-11-07 1983-05-19 Bayer Ag, 5090 Leverkusen 2-IMIDAZOLYLMETHYL-2-PHENYL-1, 3-DIOXOLANE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES
JPS58134089A (en) * 1982-02-02 1983-08-10 Yoshiki Hamada 1,3-dioxolane benzoate derivative and preparation thereof
DK354185A (en) * 1984-08-31 1986-03-01 Hoffmann La Roche 1,3-dioxolane derivatives
US4940799A (en) * 1987-07-20 1990-07-10 Ciba-Geigy Corporation Preparation of the diastereomeric mixture 2R,4S-1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
EP3925957A4 (en) 2019-02-15 2022-11-02 Tohoku University 1, 3-dioxolan derivative

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3575999A (en) * 1968-08-19 1971-04-20 Janssen Pharmaceutica Nv Ketal derivatives of imidazole
SU557755A3 (en) * 1968-08-19 1977-05-05 Янссен Фармасьютика Н.В. (Фирма) Method for preparing imidazole derivatives
US3658813A (en) * 1970-01-13 1972-04-25 Janssen Pharmaceutica Nv 1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles
DE2037610A1 (en) * 1970-07-29 1972-02-03 Bayer Ag New alpha-substituted benzyl-azoles, processes for their production and their use as pharmaceuticals
DE2041771C3 (en) * 1970-08-22 1979-07-26 Bayer Ag, 5090 Leverkusen derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0049565A2 (en) * 1980-08-25 1982-04-14 Syntex (U.S.A.) Inc. Derivatives of substituted N-alkylimidazoles, their preparation and pharmaceutical compositions containing them
EP0049565A3 (en) * 1980-08-25 1982-05-12 Syntex (U.S.A.) Inc. Derivatives of substituted n-alkylimidazoles, their preparation and pharmaceutical compositions containing them
EP0052905A1 (en) * 1980-11-24 1982-06-02 Janssen Pharmaceutica N.V. Novel (2-aryl-4-phenylthioalkyl-1,3-dioxolan-2-yl-methyl)azole derivatives

Also Published As

Publication number Publication date
AU503981B2 (en) 1979-09-27
CA1065873A (en) 1979-11-06
AU1049676A (en) 1977-07-28
NL181906C (en) 1987-12-01
CH626361A5 (en) 1981-11-13
NL181906B (en) 1987-07-01
NL7514381A (en) 1976-07-29
DE2602770A1 (en) 1976-07-29
JPS51100073A (en) 1976-09-03
FR2298328B1 (en) 1978-08-18
FR2298328A1 (en) 1976-08-20
JPS6135196B2 (en) 1986-08-12

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Legal Events

Date Code Title Description
PS Patent sealed
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19940109