ES278486A1 - A procedure for the preparation of benzodiazepine derivatives (Machine-translation by Google Translate, not legally binding) - Google Patents

A procedure for the preparation of benzodiazepine derivatives (Machine-translation by Google Translate, not legally binding)

Info

Publication number
ES278486A1
ES278486A1 ES0278486A ES278486A ES278486A1 ES 278486 A1 ES278486 A1 ES 278486A1 ES 0278486 A ES0278486 A ES 0278486A ES 278486 A ES278486 A ES 278486A ES 278486 A1 ES278486 A1 ES 278486A1
Authority
ES
Spain
Prior art keywords
hydrogen
general formula
alkyl groups
radical
pyrrhyl
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
ES0278486A
Other languages
Spanish (es)
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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
Priority claimed from US118243A external-priority patent/US3405122A/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of ES278486A1 publication Critical patent/ES278486A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A process for the preparation of benzodiazepine derivatives of the general formula ** (See formula) ** in which R and R1 represent hydrogen or alkyl groups, R2 represents a radical furyl, pyrrhyl, thienyl or pyridyl, and R3 represents hydrogen, halogen or nitro or alkoxy radicals, and its acid addition salts, characterized in that it consists of: a) reacting a ketone of the general formula ** (See formula) ** in which R represents hydrogen or alkyl groups, R2 represents a furyl, pyrrhyl, thienyl or pyridyl radical R3 represents a hydrogen atom, a halogen atom, a nitro group or an alkoxy radical, with an alpha-amino acid of the general formula ** (See formula) ** wherein R1 represents hydrogen or alkyl groups, or an ester of said amino acid, O well b) reacting a ketone of the general formula ** (See formula) ** in which R represents hydrogen or alkyl groups, R2 represents a furyl, pyrrhyl, thienyl or pyridyl radical R3 represents a hydrogen atom, a halogen atom, a nitro group or an alkoxy radical, with a haloacyl halide of the general formula ** (See formula) ** heating the resulting haloacylamino derivative with ammonia and cyclizing the amino-acylamino derivative formed, O well c) reacting a ketone of the general formula ** (See formula) ** in which R represents hydrogen or alkyl groups, R2 represents a furyl, pyrrhyl, thienyl or pyridyl radical R3 represents a hydrogen atom, a halogen atom, a nitro group or an alkoxy radical, with a carbobenzoxy glycine, hydrolyze the carbobenzoxyamino-acylamino derivative obtained with a mixture of hydrobromic acid and acetic acid and cyclize the amino-acylamino derivative formed O well d) treating a benzodiazepine derivative of the general formula ** (See formula) ** in which R and R1 represent hydrogen or alkyl groups, R2 represents a furyl, pyrrhyl, thienyl or pyridyl radical R3 represents hydrogen, halogen, nitro or alkoxy radicals, with a phosphorus halide or with hydrogen in the presence of a catalyst and, if desired, transforming the reaction product into an acid addition salt. (Machine-translation by Google Translate, not legally binding)
ES0278486A 1961-06-20 1962-06-19 A procedure for the preparation of benzodiazepine derivatives (Machine-translation by Google Translate, not legally binding) Expired ES278486A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US118243A US3405122A (en) 1961-06-20 1961-06-20 Novel 3h-1, 4-benzodiazepin-2-(1h)-ones
US130757A US3100770A (en) 1961-06-20 1961-08-11 5-pyridyl-1,4-benzodiazepine compounds

Publications (1)

Publication Number Publication Date
ES278486A1 true ES278486A1 (en) 1962-12-01

Family

ID=26816119

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0278486A Expired ES278486A1 (en) 1961-06-20 1962-06-19 A procedure for the preparation of benzodiazepine derivatives (Machine-translation by Google Translate, not legally binding)

Country Status (3)

Country Link
BE (1) BE619101A (en)
ES (1) ES278486A1 (en)
OA (1) OA02394A (en)

Also Published As

Publication number Publication date
BE619101A (en) 1962-12-10
OA02394A (en) 1970-05-05

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