GB1310998A - 4,5,6,7-tetrahydrobenzimidazoles - Google Patents

4,5,6,7-tetrahydrobenzimidazoles

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Publication number
GB1310998A
GB1310998A GB4385070A GB4385070A GB1310998A GB 1310998 A GB1310998 A GB 1310998A GB 4385070 A GB4385070 A GB 4385070A GB 4385070 A GB4385070 A GB 4385070A GB 1310998 A GB1310998 A GB 1310998A
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GB
United Kingdom
Prior art keywords
group
carbon atoms
radical
alkyl group
group containing
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
GB4385070A
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.)
Pliva Farmaceutika dd
Original Assignee
Pliva Farmaceutska Kemijska Prehrambena I Kozmeticka Industrija dd
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 Pliva Farmaceutska Kemijska Prehrambena I Kozmeticka Industrija dd filed Critical Pliva Farmaceutska Kemijska Prehrambena I Kozmeticka Industrija dd
Publication of GB1310998A publication Critical patent/GB1310998A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08Radicals containing only hydrogen and carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/10Radicals substituted by halogen atoms or nitro radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/16Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/20Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
    • C10M2215/222Triazines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/223Five-membered rings containing nitrogen and carbon only
    • C10M2215/224Imidazoles
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1310998 Tetrahydrobenzimidazoles PLIVA PHARMACEUTICAL & CHEMICAL WORKS 14 Sept 1970 [26 Sept 1969] 43850/70 Heading C2C [Also in Divisions C3 and C5] Novel 4,5,6,7 - tetrahydrobenzimidazoles of the formula in which R 1 represents a hydrogen atom, a straight or branched alkyl group containing 1 to 18 carbon atoms, a hydroxyalkyl or carboxyalkyl group containing 1 to 4 carbon atoms in the alkyl group, a 5 or 6 membered cycloalkyl, alkylcycloalkyl or cycloalkylalkyl group, an arylalkyl group containing 1 to 4 carbon atoms in the alkyl group, a glucosyl, arabinosyl, xylosyl or ribosyl group or other sugar residue derived from hexoses, pentoses or tetroses, or R 1 is the group A-Z, in which A is a straight or branched alkylene group containing 1 to 4 carbon atoms and Z is an amino, lower monoalkylamino, lower dialkylamino, morpholino, N-pyrrolidino, N-piperidino, N-piperazino, N<SP>1</SP>-lower alkyl-N-piperazino, N<SP>1</SP>- (# - hydroxy - lower alkyl) - N - piperazino or N<SP>1</SP> - (# - hydroxy - alkoxy - lower alkyl) - N- piperazino group, R 2 represents a hydrogen atom, a straight or branched alkyl group containing 1 to 20 carbon atoms, a trifluoromethyl, hydroxymethyl or carboxyl group, a carboxyalkyl group containing 1 to 4 carbon atoms, a phenyl-lower alkyl or cyclohexyl-lower alkyl group, a dialkylaminoethylaminocarbonylalkyl, dialkylaminoethylaminocarbonyl or dialkylaminoethoxycarbonylalkyl group containing 1 to 4 carbon atoms in the alkyl group, the 3-(2,3- dihydroxy propionic acid) group, the 3-(2,3- diacetoxy propionic acid methyl ester) group or the 3 - (2,3 - diacetoxy propionic acid dialkylaminoethylamide) group containing 1 to 4 carbon atoms in the alkyl group, the 5-(2,3,4,5- tetrahydroxy valeric acid) group, a polyhydroxyalkyl group containing 4 to 6 carbon atoms, a cyclopentyl or cyclohexyl radical, an alkylcyclohexyl radical containing 1 to 4 carbon atoms in the alkyl group, the carboxyoyclohexyl radical, the 2-, 3- or 4-piperidyl radical, a phenyl, mono or dialkylphenyl radical containing 1 to 4 carbon atoms in the alkyl group, a mono- or dialkoxy phenyl, mono- or dialkoxybenzyl or mono- or dialkoxyphenylethyl radical containing 1 to 4 carbon atoms in the alkoxy group, a 3,4-methylene dioxyphenyl, 3,4-methylene dioxybenzyl or 3,4-methylene dioxyphenylethyl radical, a tetrahydrofuryl group, an acylaminophenyl radical in which the acyl groups are derived from an aliphatic carboxylic acid containing 1 to 3 carbon atoms, the fluorophenyl radical, the 4,5,6,7-tetrahydrobenzimidazolyl - (2) - 1,2 - dihydroxyethyl or 4,5,6,7 - tetrahydrobenzimidazolyl - (2) - 1,2,3,4- tetrahydroxybutyl radical, an imidazolylalkyl, triazolylalkyl or tetrazolylalkyl group containing 1 to 4 carbon atoms in the alkyl group, R 3 represents a hydrogen atom, a straight or branched alkyl group containing 1 to 18 carbon atoms, a carboxyl group or an alkoxycarbonyl radical containing 1 to 4 carbon atoms in the alkoxy group, and R 4 represents a hydrogen atom, or a straight or branched alkyl group containing 1 to 4 carbon atoms, and the acid addition salts and quaternary ammonium salts of the compounds of Formula I above, excepting specifically 4, 5, 6, 7-tetrahydrobenzimidazole and 2-methyl, 5-methyl, 1,2-dimethyl, 2,5- dimethyl, 2-ethyl, 2-ethyl-5-methyl, 2-n-propyl, 2-n-propyl-5-methyl, 2-isopropyl, 2-isobutyl, 2- hexyl, 2-cyolohexyl, 2-phenyl and 2-amisyl- 4,5,6,7-tetrahydrobenzimidazoles, are prepared by hydrogenating a benzimidazole of formula where R 1 , R 2 , R 3 and R 4 are as above, or the unsaturated precursors thereof which can be hydrogenated, (a) in the form of acid addition salts or (b) in the form of free bases and in the presence of at least one equivalent of an acid for each basic group, in the presence of rhodium catalysts, and a polar solvent and, if required, the salt of the 4,5,6,7-tetrahydrobenzimidazole obtained is converted into the free base in known manner and, if required, the free base is converted into an acid addition salt or quaternary ammonium salt by reaction with an inorganic or organic acid or alkylating agent.
GB4385070A 1969-09-26 1970-09-14 4,5,6,7-tetrahydrobenzimidazoles Expired GB1310998A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19691948795 DE1948795A1 (en) 1969-09-26 1969-09-26 4,5,6,7-Tetrahydrobenzimidazoles, process for their preparation and their use as corrosion inhibitors and anti-aging agents

Publications (1)

Publication Number Publication Date
GB1310998A true GB1310998A (en) 1973-03-21

Family

ID=5746643

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4385070A Expired GB1310998A (en) 1969-09-26 1970-09-14 4,5,6,7-tetrahydrobenzimidazoles

Country Status (4)

Country Link
JP (1) JPS4924072B1 (en)
DE (1) DE1948795A1 (en)
FR (1) FR2062636A5 (en)
GB (1) GB1310998A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015086513A1 (en) * 2013-12-09 2015-06-18 Ucb Biopharma Sprl Tetrahydrobenzimidazole derivatives as modulators of tnf activity

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR69291B (en) * 1979-06-25 1982-05-13 May & Baker Ltd
DE2948056A1 (en) * 1979-11-29 1981-06-04 Boehringer Mannheim Gmbh, 6800 Mannheim NEW AMINOPROPANOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
CA2004911A1 (en) * 1988-12-22 1990-06-22 Mitsuaki Ohta 4,5,6,7-tetrahydrobenzimidazole derivatives
US6437147B1 (en) 2000-03-17 2002-08-20 Novo Nordisk Imidazole compounds
US10696558B2 (en) * 2017-03-21 2020-06-30 Exxonmobil Research & Engineering Company Zeolitic imidazolate framework materials, their synthesis and use

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015086513A1 (en) * 2013-12-09 2015-06-18 Ucb Biopharma Sprl Tetrahydrobenzimidazole derivatives as modulators of tnf activity
US10093652B2 (en) 2013-12-09 2018-10-09 Ucb Biopharma Sprl Tetrahydrobenzimidazole derivatives as modulators of TNF activity

Also Published As

Publication number Publication date
FR2062636A5 (en) 1971-06-25
DE1948795A1 (en) 1971-04-08
JPS4924072B1 (en) 1974-06-20

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PLNP Patent lapsed through nonpayment of renewal fees