GB1312056A - 2-5,-nitro-2,-imidazolyl-benzimidazoles - Google Patents

2-5,-nitro-2,-imidazolyl-benzimidazoles

Info

Publication number
GB1312056A
GB1312056A GB1874370A GB1874370A GB1312056A GB 1312056 A GB1312056 A GB 1312056A GB 1874370 A GB1874370 A GB 1874370A GB 1874370 A GB1874370 A GB 1874370A GB 1312056 A GB1312056 A GB 1312056A
Authority
GB
United Kingdom
Prior art keywords
nitro
reacting
prepared
group
ethyl
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
GB1874370A
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.)
Bayer Pharma AG
Original Assignee
Schering 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 Schering AG filed Critical Schering AG
Publication of GB1312056A publication Critical patent/GB1312056A/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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/325—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups reduction by other means than indicated in C07C209/34 or C07C209/36
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • 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
    • C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members

Landscapes

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

Abstract

1312056 Nitroimidazole derivatives SCHERING AG 20 April 1970 [19 April 1969] 18743/70 Heading C2C Novel compounds of Formula I in which A is H, C 1-5 alkyl, C 2-5 hydroxyalkyl which may be esterified, C 2-5 haloalkyl, (tosyloxy-C 2-5 alkyl), phenyl or alk-NR 3 R 4 , where each of R 3 and R 4 is a saturated or unsaturated acyclic C 1-5 hydrocarbyl group or -NR 3 R 4 is a cyclic group which may be substituted by a C 1-5 alkyl group and/or may contain a further heteroatom selected from nitrogen, sulphur and oxygen atoms, and alk is C 2-5 alkylene, each of R 1 and R 2 is H, C 1-4 alkyl, C 1-4 alkoxy, halogen, nitro, trifluoromethyl or carboxy, and X is a saturated or unsaturated acyclic C 1-5 hydrocarbyl which may be substituted in the 2- position by hydroxy, acyloxy containing up to 5 carbon atoms or benzoyloxy, and their salts, are prepared by (a) reacting a compound of Formula II or a salt thereof, with an acid of Formula III or a reactive derivative thereof, or (b) reacting a compound of Formula II or a salt thereof in the presence of an oxidizing agent with an aldehyde of Formula IV and then, if desired, in the resulting compound, converting the hydroxyl group in any hydroxyalkyl group represented by A into a tosyloxy group, a chlorine atom or an -NR 3 R 4 group, and/or hydrolysing any ester group into a hydroxyl group, and/or, if desired, converting a resulting free base or acid into a salt thereof, and/or converting a resulting salt into the corresponding free compound. 2 - (3<SP>1</SP> - Dibutylamino - propylamino) - aniline is prepared by reacting o-nitro-bromobenzene with 3-dibutylaminopropylamine to form 2-(3<SP>1</SP>- dibutylamino - propylamino) - nitrobenzene and reducing this with hydrazine hydrate and palladium. 2 - (3<SP>1</SP> - Morpholino - propylamino) - aniline, 2 - (3<SP>1 </SP>- dimethylamino - propylamino) - aniline and 3 - amino - 4 - (2<SP>1 </SP>- dimethylaminoethylamino) -toluene are similarly prepared via the corresponding nitro compounds. N-methyl-orthophenylene-diamine is prepared by reduction of 2- nitro-N-methylaniline. 5 - Nitro - 1 - ethyl - 2 - hydroxymethyl - imidazole is prepared by reacting 5-nitro-1-ethylimidazole with formaldehyde. 5 - Nitro - 1 - (ethyl or butyl) - 2 - imidazoleiminocarboxylic acid ethyl ester is prepared by reacting 5 - nitro - 1 - (ethyl or butyl) - 2- hydroxymethyl with lead tetracetate to give 5- nitro - 1 - (ethyl or butyl) - 2 - imidazole - aldehyde, reacting this with hydroxylamine to give the corresponding oxime, reacting this with phosphorus oxychloride to give 5-nitro-1-(ethyl or butyl) - 2 - imidazole - carboxylic acid nitrile (the 1-methyl nitrite compound is also prepared by this method from the oxime) and reacting this with ethanol. Antimicrobial compositions comprise one of the above novel compounds together with a pharmaceutical carrier. The compositions may be in the form of pills, dragees, capsules, syrups or solutions.
GB1874370A 1969-04-19 1970-04-20 2-5,-nitro-2,-imidazolyl-benzimidazoles Expired GB1312056A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1920635A DE1920635C3 (en) 1969-04-19 1969-04-19 2- (1-methyl-5-nitro-2-imidazolyl) benzimidazoles

Publications (1)

Publication Number Publication Date
GB1312056A true GB1312056A (en) 1973-04-04

Family

ID=5732064

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1874370A Expired GB1312056A (en) 1969-04-19 1970-04-20 2-5,-nitro-2,-imidazolyl-benzimidazoles

Country Status (15)

Country Link
JP (1) JPS4914231B1 (en)
AT (1) AT294075B (en)
BE (1) BE749102A (en)
CH (2) CH546774A (en)
CS (1) CS167896B2 (en)
DE (1) DE1920635C3 (en)
DK (1) DK137758B (en)
ES (1) ES378368A1 (en)
FI (1) FI52861C (en)
FR (1) FR2042351B1 (en)
GB (1) GB1312056A (en)
NL (1) NL7005703A (en)
NO (1) NO126624B (en)
SE (1) SE364962B (en)
ZA (1) ZA702577B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0122109A2 (en) * 1983-04-07 1984-10-17 Smith Kline & French Laboratories Limited Preparation of cyano- or aminoalkyl substituted aromatic amines

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053472A (en) * 1969-04-19 1977-10-11 Schering Aktiengesellschaft 2-(5-nitro-2-imidazolyl)-benzimidazoles
IT1043840B (en) * 1971-05-08 1980-02-29 Poli Ind Chimica Spa PYRIMIDINES 2 5 REPLACED AND PROCESS FOR THEIR PREPARATION
US3996238A (en) * 1972-02-08 1976-12-07 Ciba-Geigy Corporation 4- or 5-Nitroimidazoles and processes for their manufacture
BE795636A (en) * 1972-02-19 1973-08-20 Schering Ag NITROIMIDAZOLYLPYRIMIDINES, AND THEIR PREPARATION PROCESS
CA2168016C (en) * 1994-05-31 2000-09-26 Akio Matsunaga Benzimidazole derivatives
EP0777656B1 (en) * 1994-08-26 2004-04-14 Auckland Division Cancer Society Of New Zealand (Incorporated) Novel dna-targeted alkylating agents

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0122109A2 (en) * 1983-04-07 1984-10-17 Smith Kline & French Laboratories Limited Preparation of cyano- or aminoalkyl substituted aromatic amines
EP0122109A3 (en) * 1983-04-07 1986-03-12 Smith Kline & French Laboratories Limited Preparation of cyano- or aminoalkyl substituted aromatic amines

Also Published As

Publication number Publication date
DK137758B (en) 1978-05-01
AT294075B (en) 1971-11-10
FI52861B (en) 1977-08-31
CH546774A (en) 1974-03-15
FR2042351B1 (en) 1973-07-13
ES378368A1 (en) 1972-06-16
BE749102A (en) 1970-10-19
DE1920635C3 (en) 1979-06-28
DE1920635A1 (en) 1970-10-29
CH546768A (en) 1974-03-15
JPS4914231B1 (en) 1974-04-05
FR2042351A1 (en) 1971-02-12
ZA702577B (en) 1971-01-27
CS167896B2 (en) 1976-05-28
FI52861C (en) 1977-12-12
DE1920635B2 (en) 1978-11-02
NL7005703A (en) 1970-10-21
SE364962B (en) 1974-03-11
DK137758C (en) 1978-10-09
NO126624B (en) 1973-03-05

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee