Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
  • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
  • C07D487/06—Peri-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
  • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
  • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
  • C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups

Definitions

• the invention relates to 2- [(3-nitro-benzyl) amino] alkyl-a ine and a process for the preparation of 4,5,6,7-tetra-hydro-imidazo- [4,5, ljk] [1.4] -benzodiazepin-2 (IH) thiones via the 2- [(3-nitro-benzyl) amino] alkylamines as intermediates.
• the invention relates to an improved process for the preparation of 4,5,6,7-tetrahydro-imidazo- [4,5, ljk] [1.4] - benzodiazepine-2 (IH) thiones of the general formula I
• R1 is a hydrogen atom or a straight-chain or branched alkyl radical having 1-6 carbon atoms
• R2 represents a hydrogen atom, a straight-chain or branched alkyl radical having 1-6 carbon atoms, a straight-chain or branched alkenyl radical having 3-6 carbon atoms, a C 3 -C 6 alkynyl radical, a C 3 -C 5 cycloalkyl radical or a C ⁇ _-Cg- Alkyl radical which can also be substituted by a phenyl radical or a C3-Cg-cycloalkyl radical, 3 and R4 are identical or different and, independently of one another, denote hydrogen, halogen, hydroxyl, Ci-Cg-alkoxy, Cx-Cg-alkyl or amino.
• R * L represents a hydrogen atom or a straight-chain or branched alkyl group with 1-6 carbon atoms.
• the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl and isohexyl groups are preferred
• 2 can represent a hydrogen atom or a straight-chain or branched C 1 -C 6 -alkyl group.
• the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl and isohexyl group are preferred.
• R2 can also be a straight-chain or branched C3-C6-
• Alkylene group mean.
• the allyl, 2-methylallyl, isobutenyl, pentenyl, isopentenyl, hexenyl and isohexenyl group are preferred.
• R2 can also mean a straight-chain or branched C3-C6 alkynyl group. This means in particular a 2-propynyl, 2-butynyl, 3-butynyl, pentynyl or hexynyl radical.
• a C3 ⁇ C5-C cloalkyl radical for R3 means a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl radical.
• R3 and R4 can be the same or different and independently of one another are hydrogen, halogen, such as fluorine, chlorine or bromine, hydroxy, alkyl, such as methyl or ethyl, or alkoxy, such as methoxy or ethoxy,
• the compounds of general formula I can have one or more
• REPLACEMENT LEAF have asymmetric carbon atoms.
• the invention therefore also relates to all optically active and diastereomeric forms and racemic and diastereomeric mixtures.
• R * j_, 2, R 3 and R4 have the meanings given, are prepared by using a compound of the general formula II,
• R ⁇ _, R 2 , R3 and R4 have the meanings given, according to a conventional method with a reagent which transfers the thiocarbonyl group, such as, for example, carbon disulfide, thiocarbonyldiimidazole, thiophosgene or thiourea.
• a reagent which transfers the thiocarbonyl group such as, for example, carbon disulfide, thiocarbonyldiimidazole, thiophosgene or thiourea.
• R 1, R 2, R 3 and R 4 have the meanings indicated and convert the nitro group into an amino group by a conventional method known to the person skilled in the art.
• the compounds of general formula III can be prepared by using a compound of general
• X represents a halogen atom or a sulfonic ester grouping.
• the compounds of general formula IV can be prepared by using a compound of general formula VI,
• REPLACEMENT LEAF in which R_, 3 and 4 have the meanings given and Y represents a halogen atom, is subjected to a cyclization reaction.
• R] _, R3, R4 and Y have the meanings given, is subjected to a reduction using hydrogen boron or diborane.
• the compounds of the general formula VII can be prepared by using a compound of the general formula VII
• R, R 3 , R4 and Y have the meanings given, and R5 is hydrogen or an alkyl radical, is subjected to an amidation reaction by methods known to those skilled in the art.
• the compounds of the general formula VIII can be prepared by using a compound of the general formula VIII
• Ri has the meanings given and R 5 is hydrogen or an alkyl radical, brings about the reaction in the customary manner.
• the compounds of the general formula IX are known from the literature or can be prepared by methods known from the literature.
• REPLACEMENT LEAF are and relate to racemates or optically active compounds.
• the reactions of the compounds of the general formula II with a reagent transferring a thiocarbonyl group to a compound of the general formula I are carried out by, for example, reacting a compound of the general formula II with carbon disulfide in an aqueous-alcoholic solution in the presence of alkali by a method known to those skilled in the art or by reacting a compound of the general formula II with thiocarbonyldiimidazole in an inert solvent, such as, for example, Dimethylformamide brings to reaction.
• the compounds of the general formula II are prepared by converting the nitro group into an amino group in a compound of the general formula by a method known to those skilled in the art.
• the compounds of the general formula IV are reacted with compounds of the general formula V to give compounds of the general formula III by reacting the compounds of the general formula IV with compounds of the general formula V in an inert solvent, such as, for example, dimethylformamide, dimethylacetamide, acetone, methyl ethyl ketone or alcohol at at temperatures between room temperature and reflux temperature of the solvent, tion agent such as sodium carbonate or potassium carbonate to the skilled person by methods known brings preferably between 40 "C and 60 C in the presence of a ⁇ alkaline Kondensa ⁇ to the reaction.
• an inert solvent such as, for example, dimethylformamide, dimethylacetamide, acetone, methyl ethyl ketone or alcohol
• the cyclization of a compound of general formula VI to a compound of general formula IV can be carried out by using a compound of general Formula VI in an inert solvent such as dimethyl formamide, dimethylacetamide, acetone, methyl ethyl ketone or alcohol in the presence of an alkaline condensing agent such as sodium carbonate or potassium carbonate to react at temperatures between room temperature and the reflux temperature of the solvent.
• an inert solvent such as dimethyl formamide, dimethylacetamide, acetone, methyl ethyl ketone or alcohol
• an alkaline condensing agent such as sodium carbonate or potassium carbonate
• the cyclization reaction of a compound of the general formula VI to a compound of the general formula IV can also be carried out by heating a compound of the general formula IV in the presence of an alkaline condensing agent, such as, for example, sodium carbonate or potassium carbonate, without the addition of a solvent to temperatures between 100 "C and 200 ⁇ C, preferably between 130 ⁇ C and 170 ° C.
• an alkaline condensing agent such as, for example, sodium carbonate or potassium carbonate
• the compounds of the general formula VI are shown in that a compound of the general formula VII with hydrogen boron or diborane in an inert solvent, such as e.g. Tetrahydrofuran, dioxane, diethyl ether or methylene chloride at temperatures between room temperature and reflux temperature of the solvent or by reacting a compound of general formula VI in an inert solvent such as e.g. Subjects methylene chloride reduction with a tetraalkylammonium borohydride.
• an inert solvent such as e.g. Tetrahydrofuran, dioxane, diethyl ether or methylene chloride
• B a borane-ammonia complex, borane-tert-butylamine complex, borane-N, N-diethylaniline complex, borane-dimethylamine complex, borane-4-dimethylaminopyridine complex, borane-dimethyl sulfide complex, borane -Dimethyl sulfide complex, borane-N-ethyldiisopropylamine complex, borane-N-ethylmorpholine complex, borane-2,6-lutidine complex, borane-N-methylmorpholine complex, borane-morpholine complex, borane-1,4 -Oxathian complex, borane-N-phenylmorpholine complex, borane-piperazine complex,
• the compounds of the general formula VII are illustrated by subjecting a compound of the general formula VIII to an amide formation reaction according to the person skilled in the art and methods known from the literature.
• the compounds of general formula VIII can be prepared by reacting a compound of general formula IX with a compound of general formula X by methods known to those skilled in the art.
• the invention relates in particular to a new and economical process for the production of

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (2)

• 1990
  • 1990-11-16 DE DE4036552A patent/DE4036552C1/de not_active Expired - Lifetime
• 1991
  • 1991-10-29 CA CA002096238A patent/CA2096238A1/en not_active Abandoned
  • 1991-10-29 WO PCT/EP1991/002038 patent/WO1992008706A1/de not_active Ceased
  • 1991-10-29 AU AU88559/91A patent/AU8855991A/en not_active Abandoned
  • 1991-10-29 EP EP91918424A patent/EP0557307A1/de not_active Withdrawn
  • 1991-10-29 JP JP3517660A patent/JPH06502400A/ja active Pending
  • 1991-11-11 IL IL100033A patent/IL100033A0/xx unknown
  • 1991-11-15 IE IE397991A patent/IE913979A1/en unknown
  • 1991-11-15 ZA ZA919050A patent/ZA919050B/xx unknown

Patent Citations (2)

Non-Patent Citations (1)

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