GB984707A - Novel benzodiazepine derivatives and a process for the manufacture thereof - Google Patents

Novel benzodiazepine derivatives and a process for the manufacture thereof

Info

Publication number
GB984707A
GB984707A GB8239/63A GB823963A GB984707A GB 984707 A GB984707 A GB 984707A GB 8239/63 A GB8239/63 A GB 8239/63A GB 823963 A GB823963 A GB 823963A GB 984707 A GB984707 A GB 984707A
Authority
GB
United Kingdom
Prior art keywords
formula
acid
halo
alkyl
benzophenone
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
GB8239/63A
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 GB984707A publication Critical patent/GB984707A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 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
    • C07D211/56—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0984707/C2/1> (wherein R1 stands for a halogen atom or an alkyl, alkoxy or trifluoromethyl group, R2 and R3 each stand for an alkyl group or, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heteromonocyclic group which may contain an oxygen atom or one further nitrogen atom, the broken lines radiating from the rings denote that the substituents attached thereby are optional and the broken line within the diazepine ring indicates that the double bond in the 4,5-position is optional) and acid addition and quaternary ammonium salts thereof, pharmaceutical preparations containing them, and their preparation by either reacting a benzophenone of the formula <FORM:0984707/C2/2> or a salt thereof with a strong acid, with an a amino acid of the formula <FORM:0984707/C2/3> or an ester thereof, or a salt of this acid or ester with a strong acid, or with an a -halo-acid halide of the formula <FORM:0984707/C2/4> and treating the resulting 2-(a -halo-alkanoyl-amido)-benzophenone with ammonia or, in the case where R2 and R3 in the product are to be alkyl groups, reductively alkylating a nitro compound of the formula <FORM:0984707/C2/5> and, if desired, N1-alkylating any 1-unsubstituted cyclized compound and/or converting it or any 1-substituted cyclized compound into an acid addition or quaternary ammonium salt, the process including, if required, a reduction of any cyclized compound containing a double bond in the 4,5-position of the diazepine ring. The term "alkyl" is defined as meaning a C1-7 alkyl group. The benzophenone starting materials are prepared by reacting a corresponding 5-halo-2-aminobenzophenone with a peracid, treating the resulting 5 - halo - 2 - nitrobenzophenone with the appropriate secondary amine, reducing the 5 - (substituted amino) - 2 - nitrobenzophenone obtained and, if desired, alkylating the reduction product. The compounds of the invention are sedatives, muscle relaxants and anticonvulsants, and may be administered orally, parenterally or rectally in the form of pharmaceutical preparations (e.g. tablets, dragees, suppositories, capsules, solutions, emulsions or suspensions) containing them together with a carrier, with or without other (unspecified) therapeutically useful substances. Specification 972,968 is referred to.
GB8239/63A 1962-03-09 1963-03-01 Novel benzodiazepine derivatives and a process for the manufacture thereof Expired GB984707A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US178566A US3202665A (en) 1962-03-09 1962-03-09 5-piperidino-and 5-diloweralkylamino-2-amino-benzophenones

Publications (1)

Publication Number Publication Date
GB984707A true GB984707A (en) 1965-03-03

Family

ID=22653052

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8239/63A Expired GB984707A (en) 1962-03-09 1963-03-01 Novel benzodiazepine derivatives and a process for the manufacture thereof

Country Status (6)

Country Link
US (1) US3202665A (en)
AT (1) AT242157B (en)
CH (2) CH440298A (en)
ES (1) ES285855A1 (en)
GB (1) GB984707A (en)
SE (2) SE318885B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU167950B (en) * 1973-07-26 1976-01-28
US4064121A (en) * 1973-07-26 1977-12-20 Richter Gedeon Vegyeszeti Gyar Rt. Substituted nitrobenzophenone derivatives and a process for the preparation thereof
WO2006044753A2 (en) * 2004-10-19 2006-04-27 Smithkline Beecham Corporation Chemical compounds

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2893992A (en) * 1959-07-07 I ii i i
US3109843A (en) * 1963-11-05 Process for preparing
CH345342A (en) * 1954-03-03 1960-03-31 Ciba Geigy Process for the preparation of new basic substituted heterocycles
US2914563A (en) * 1957-08-06 1959-11-24 Wm S Merrell Co Therapeutic composition
US2926180A (en) * 1957-06-18 1960-02-23 Universal Oil Prod Co Condensation of aromatic ketones with carbohydrates and related materials
US2914564A (en) * 1957-08-06 1959-11-24 Wm S Merrell Co Amine derivatives of 1, 1, 2-triphenylethane
US3045008A (en) * 1960-02-16 1962-07-17 Pfizer & Co C Novel 1, 4-diazepines

Also Published As

Publication number Publication date
CH457462A (en) 1968-06-15
CH440298A (en) 1967-07-31
AT242157B (en) 1965-09-10
DE1445871A1 (en) 1969-03-13
ES285855A1 (en) 1963-08-16
SE317681B (en) 1969-11-24
US3202665A (en) 1965-08-24
SE318885B (en) 1969-12-22

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