FR2436780A1 - Prepn. of 5-nitro-imidazole deriv. esp. 1-methyl-2-isopropyl cpd. - by reaction of 1-amino-2-nitro-ethylene cpd. and a N-halo-amidine, to give antimicrobial, antibacterial and amoebicide - Google Patents

Prepn. of 5-nitro-imidazole deriv. esp. 1-methyl-2-isopropyl cpd. - by reaction of 1-amino-2-nitro-ethylene cpd. and a N-halo-amidine, to give antimicrobial, antibacterial and amoebicide

Info

Publication number
FR2436780A1
FR2436780A1 FR7833416A FR7833416A FR2436780A1 FR 2436780 A1 FR2436780 A1 FR 2436780A1 FR 7833416 A FR7833416 A FR 7833416A FR 7833416 A FR7833416 A FR 7833416A FR 2436780 A1 FR2436780 A1 FR 2436780A1
Authority
FR
France
Prior art keywords
opt
cpd
nitro
halo
methyl
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.)
Granted
Application number
FR7833416A
Other languages
French (fr)
Other versions
FR2436780B1 (en
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.)
Farchemia SpA
Original Assignee
Farchemia SpA
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 Farchemia SpA filed Critical Farchemia SpA
Publication of FR2436780A1 publication Critical patent/FR2436780A1/en
Application granted granted Critical
Publication of FR2436780B1 publication Critical patent/FR2436780B1/fr
Granted 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

Landscapes

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

Abstract

Prepn. of nitroimidazole derivs. of formula (I) by reaction of 1-amino-2-nitroethylene cpd. (R2)2N-CH=CH-NO2 (II) with a N-haloamidine of formula RNH-CR1=NX (III) is claimed. R = opt branched, opt. unsaturated, 1-8C monovalent aliphatic hydrocarbyl group, which is opt. substd. by one or more aryl (pref. phenyl, alpha- or beta- naphthyl), halo, hydroxy, 1-4C alkoxy, aryloxy, nitro or perhaloalkyl e.g. CF3; R1 is an R group or 6-10C aryl opt. substd. by one or more substituents, such as lower alkyl, hydroxy, lower alkoxy, nitro, opt. alkylated, arylated or acylated amino, carboxy and alkoxycarbonyl; the two R2 gps. independently are lower alkyl (e.g. methyl, ethyl, propyl) or 5-6C cycloalkyl or the 2 groups together with N atom form a satd. heterocyclic opt. contg. further heteroatoms e.g. pyrrolidino, piperidino, morpholino or N-methylpiperazino and X=halo pref. Cl. (I) are antimicrobials e.g. bactericides active against Trichomonas and amoebicides. A pref. cpd. is 2-isopropyl-1-methyl-5-nitroimidazole(ipronidazole) used to treat Histomonas meleagridis infections and which has good activity against E. histolytica, Trichomonas vaginalis and Trichomonas foetus. The present process gives high yields (5-70%) of pure prod. which is readily isolated and avoids toxic by-products and difficutly controllable reactions found in known processes.
FR7833416A 1978-09-19 1978-11-27 Prepn. of 5-nitro-imidazole deriv. esp. 1-methyl-2-isopropyl cpd. - by reaction of 1-amino-2-nitro-ethylene cpd. and a N-halo-amidine, to give antimicrobial, antibacterial and amoebicide Granted FR2436780A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT27866/78A IT1098864B (en) 1978-09-19 1978-09-19 PROCESS FOR THE PREPARATION OF NITROIMIDAZOLI

Publications (2)

Publication Number Publication Date
FR2436780A1 true FR2436780A1 (en) 1980-04-18
FR2436780B1 FR2436780B1 (en) 1982-04-09

Family

ID=11222488

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7833416A Granted FR2436780A1 (en) 1978-09-19 1978-11-27 Prepn. of 5-nitro-imidazole deriv. esp. 1-methyl-2-isopropyl cpd. - by reaction of 1-amino-2-nitro-ethylene cpd. and a N-halo-amidine, to give antimicrobial, antibacterial and amoebicide

Country Status (2)

Country Link
FR (1) FR2436780A1 (en)
IT (1) IT1098864B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0049913A2 (en) * 1980-09-17 1982-04-21 Gist-Brocades N.V. New ethenylimidazole derivatives, processes for their preparation and pharmaceutical compositions containing them; intermediates, useful in their preparation and a process for the preparation thereof
EP0057365A2 (en) * 1981-01-30 1982-08-11 BASF Aktiengesellschaft Vinyl azoles, process for their preparation and their application as fungicides
FR2504134A1 (en) * 1981-04-21 1982-10-22 Bononi Loris NOVEL DERIVATIVES OF NITROIMIDAZOLE, PROCESS FOR THEIR PREPARATION AND TRICHOMONOACID THERAPEUTIC COMPOSITIONS CONTAINING THE SAME
EP0103100A1 (en) * 1982-08-20 1984-03-21 Euroresearch S.R.L. 1-Methyl-5-nitro-imidazoline derivatives and therapeutic compositions which contain them as active principle
EP0111657A2 (en) * 1982-10-27 1984-06-27 Pietro Tommaso Tessitore New 2-(1-alkyl-5-nitro)-imidazolyl-1-(2-hydroxy-5-alkyl)-phenyl carbinols, method for the preparation thereof and pharmaceutical compositions containing them
FR2625997A1 (en) * 1988-01-15 1989-07-21 Rhone Poulenc Sante Process for the preparation of 1,2-dimethyl-5-nitroimidazole
EP0325512A1 (en) * 1988-01-15 1989-07-26 Rhone-Poulenc Sante Process for the preparation of 1-alkyl-5-nitro-imidazoles

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1119636A (en) * 1966-04-12 1968-07-10 Hoffmann La Roche A novel imidazole derivative and a novel intermediate therefor

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1119636A (en) * 1966-04-12 1968-07-10 Hoffmann La Roche A novel imidazole derivative and a novel intermediate therefor

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0049913A2 (en) * 1980-09-17 1982-04-21 Gist-Brocades N.V. New ethenylimidazole derivatives, processes for their preparation and pharmaceutical compositions containing them; intermediates, useful in their preparation and a process for the preparation thereof
EP0049913A3 (en) * 1980-09-17 1982-10-06 Gist - Brocades N.V. New ethenylimidazole derivatives, processes for their preparation and pharmaceutical compositions containing them; intermediates, useful in their preparation and a process for the preparation thereof
EP0057365A2 (en) * 1981-01-30 1982-08-11 BASF Aktiengesellschaft Vinyl azoles, process for their preparation and their application as fungicides
EP0057365A3 (en) * 1981-01-30 1982-09-01 Basf Aktiengesellschaft Vinyl azoles, process for their preparation and their application as fungicides
EP0063401A3 (en) * 1981-04-21 1983-09-21 Loris Jacopo Bononi Nitroimidazoles having trichomonacidal activity, a process for their preparation and related pharmaceutical compositions
EP0063401A2 (en) * 1981-04-21 1982-10-27 Loris Jacopo Bononi Nitroimidazoles having trichomonacidal activity, a process for their preparation and related pharmaceutical compositions
FR2504134A1 (en) * 1981-04-21 1982-10-22 Bononi Loris NOVEL DERIVATIVES OF NITROIMIDAZOLE, PROCESS FOR THEIR PREPARATION AND TRICHOMONOACID THERAPEUTIC COMPOSITIONS CONTAINING THE SAME
US4463012A (en) * 1981-04-21 1984-07-31 Bononi Loris J Nitroimidazoles having trichomonacidal activity and pharmaceutical compositions thereof
EP0103100A1 (en) * 1982-08-20 1984-03-21 Euroresearch S.R.L. 1-Methyl-5-nitro-imidazoline derivatives and therapeutic compositions which contain them as active principle
US4476138A (en) * 1982-08-20 1984-10-09 Farmatis S.R.L. 1-Methyl-5-nitro-(2-substituted)-2H-imidazole derivatives, and use as bactericidal and protozoacidal agents
EP0111657A2 (en) * 1982-10-27 1984-06-27 Pietro Tommaso Tessitore New 2-(1-alkyl-5-nitro)-imidazolyl-1-(2-hydroxy-5-alkyl)-phenyl carbinols, method for the preparation thereof and pharmaceutical compositions containing them
EP0111657A3 (en) * 1982-10-27 1984-07-25 Pietro Tommaso Tessitore New 2-(1-alkyl-5-nitro)-imidazolyl-1-(2-hydroxy-5-alkyl)-phenyl carbinols, method for the preparation thereof and pharmaceutical compositions containing them
US4478846A (en) * 1982-10-27 1984-10-23 Tessitore Pietro T 2-(1-Alkyl-5-nitro)-imidazolyl-1-(2-hydroxy-5-alkyl)-phenyl carbinols and pharmaceutical compositions containing them
FR2625997A1 (en) * 1988-01-15 1989-07-21 Rhone Poulenc Sante Process for the preparation of 1,2-dimethyl-5-nitroimidazole
EP0325512A1 (en) * 1988-01-15 1989-07-26 Rhone-Poulenc Sante Process for the preparation of 1-alkyl-5-nitro-imidazoles

Also Published As

Publication number Publication date
IT1098864B (en) 1985-09-18
IT7827866A0 (en) 1978-09-19
FR2436780B1 (en) 1982-04-09

Similar Documents

Publication Publication Date Title
MY102919A (en) Pleuromutilin derivatives process for their preparation and their use.
AU546200B2 (en) Mono-n-substituted 1,2,4-triazoles
GR3024285T3 (en) Process for the preparation of chlorothiazole derivatives
KR900018099A (en) 3-Pyrrolidinyl thio 1-azabicyclo [3.2.0] -hept-2-ene-2-carboxylic acid compound
FR2436780A1 (en) Prepn. of 5-nitro-imidazole deriv. esp. 1-methyl-2-isopropyl cpd. - by reaction of 1-amino-2-nitro-ethylene cpd. and a N-halo-amidine, to give antimicrobial, antibacterial and amoebicide
ES8306182A1 (en) A process for enzymatic replacement of the B-30 amino acid in insulins.
KR880012604A (en) (1R, 5S, 6S) -2-substituted thio-6 [(R) -1-hydroxyethyl] -1-methyl-carbapenem-3-carboxylic acid derivative
KR950700292A (en) Nitrosation process
HU913462D0 (en) Process for the production of heteroaroyl derivatives of moncyclic betha-lactame antibiotics and of medical preparations containing them
FR2167171A5 (en) Hetero-substd 1,2,3-triazoles - as plant growth regulants and pesticides
ES485222A1 (en) Pharmaceutical composition containing 3,4-dihydro-3-oxo-2-quinoxalines, novel such quinoxalines and processes for the production thereof.
FI882002A (en) Process for the preparation of therapeutically active phenylpiperidine derivatives
UY23600A1 (en) PROCEDURE FOR THE PREPARATION OF BENZODIAZEPINES
ES2005165A6 (en) Pharmaceutical composition comprising an organic zinc complex and a process for preparing the active substance
GB1417322A (en) Acylamines of bicyclic hydrocarbons for the regulation of plant growth
ES289110A1 (en) Improvements in or relating to ergolene derivatives
ES420853A1 (en) Process for the stabilization of methionine
GB1002644A (en) Improvements in or relating to nitrofurfurylideneamino hydantoins
GB1341339A (en) Pyridyl thiourea derivatives and preparation thereof
ES8302093A1 (en) Novel beta-lactam compounds, process for production thereof, and medicines containing them.
AU567101B2 (en) Imidazole and triazole pesticides
ES451449A1 (en) Penicillins
GB1496100A (en) Ureidoacetic acid derivatives
ES295188A1 (en) Procedure for the preparation of pure, well crystallized, hardly soluble salts of fenoximetilpenicillina (Machine-translation by Google Translate, not legally binding)
FR2079575A5 (en) Dehydrohalogenation of organic compounds - with quaternary ammonium phosphates or phosphoonates

Legal Events

Date Code Title Description
ST Notification of lapse