GB1012260A - Benzdiaz[1,4]epines and the manufacture thereof - Google Patents

Benzdiaz[1,4]epines and the manufacture thereof

Info

Publication number
GB1012260A
GB1012260A GB15610/64A GB1561064A GB1012260A GB 1012260 A GB1012260 A GB 1012260A GB 15610/64 A GB15610/64 A GB 15610/64A GB 1561064 A GB1561064 A GB 1561064A GB 1012260 A GB1012260 A GB 1012260A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
pyridine
condensing
halogen atom
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
GB15610/64A
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
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1012260A publication Critical patent/GB1012260A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:1012260/C2/1> (wherein R represents a halogen atom or a nitro or trifluoromethyl group, the lower alkyl groups each contain not more than seven carbon atoms, and the broken lines denote optional substituents) and acid addition salts thereof, pharmaceutical preparations containing them, and their preparation by (a) reducing a compound of the formula <FORM:1012260/C2/2> (wherein R1 represents a halogen atom or trifluoromethyl group) with lithium aluminium hydride, (b) reducing a compound of the formula <FORM:1012260/C2/3> with Raney nickel, (c) condensing a compound of the formula <FORM:1012260/C2/4> with a compound of the formula <FORM:1012260/C2/5> (d) condensing a compound of the formula (d) condensing a compound of the formula <FORM:1012260/C2/6> (wherein R2 represents a halogen atom or nitro group) with a b -acylaminoethyl halide and cyclizing the condensation product of the formula <FORM:1012260/C2/7> (wherein R3 represents the acylamino residue of the b -acylaminoethyl halide), or (e) condensing a compound of the formula <FORM:1012260/C2/8> (wherein hal represents a halogen atom) with a compound of the formula <FORM:1012260/C2/9> the condensation either proceeding directly or via an intermediate of the formula <FORM:1012260/C2/100> which is cyclized, optionally followed in each case (when appropriate) by introduction of the 1-alkyl and/or 7-nitro groups, and/or acid addition salt formation. The following intermediates are prepared from the starting materials indicated in parentheses: 7 - bromo - 5 - [pyridyl - (2)]-1, 3- dihydro - 2H - benzdiaz [1,4]epin - 2 - one (2-(2-amino - 5 - bromobenzoyl) pyridine, via 2 - (2 - bromoacetamido - 5 - bromobenzoyl) pyridine hydrobromide and the corresponding free base); 2 - (2 - chlor - 5 - nitrobenzoyl)pyridine (2-bromopyridine and o-chlorobenzonitrile, 2-(2-chlorophenyl) pyridyl carbinol, or 2-bromochlorobenzene and 2-cyanopyridine, in each case via 2 - (2 - chlorobenzoyl)pyridine); 2 - (2 - chloro-5 - trifluoromethylbenzoyl)pyridine (2 - bromopyridine and 2-chloro-5-trifluoromethylbenzonitrile). The compounds of the invention are muscle relaxants, sedatives and anticonvulsants, and may be administered enterally or parenterally in the form of pharmaceutical preparations (e.g. tablets, drag<\>ees, suppositories, capsules, solutions, emulsions or suspensions) containing them, with or without other (unspecified) active ingredients, together with a carrier. Specification 948,888 is referred to.
GB15610/64A 1963-04-19 1964-04-15 Benzdiaz[1,4]epines and the manufacture thereof Expired GB1012260A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US27430363A 1963-04-19 1963-04-19

Publications (1)

Publication Number Publication Date
GB1012260A true GB1012260A (en) 1965-12-08

Family

ID=23047643

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15610/64A Expired GB1012260A (en) 1963-04-19 1964-04-15 Benzdiaz[1,4]epines and the manufacture thereof

Country Status (9)

Country Link
BE (1) BE646617A (en)
BR (1) BR6458448D0 (en)
CH (1) CH455809A (en)
DK (1) DK112449B (en)
ES (1) ES298897A1 (en)
FR (2) FR3682M (en)
GB (1) GB1012260A (en)
NL (1) NL138937B (en)
SE (2) SE313572B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2034541A1 (en) * 1969-02-12 1970-12-11 Sumitomo Chemical Co

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2034541A1 (en) * 1969-02-12 1970-12-11 Sumitomo Chemical Co

Also Published As

Publication number Publication date
ES298897A1 (en) 1964-10-16
BR6458448D0 (en) 1973-08-16
DE1445892B2 (en) 1975-05-28
NL6404216A (en) 1964-10-20
CH455809A (en) 1968-05-15
DE1445892A1 (en) 1969-02-06
FR3682M (en) 1965-11-15
BE646617A (en) 1964-10-16
SE313572B (en) 1969-08-18
NL138937B (en) 1973-05-15
FR1398185A (en) 1965-05-07
SE329857B (en) 1970-10-26
DK112449B (en) 1968-12-16

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