GB943604A - Dibenzocycloheptane derivatives - Google Patents

Dibenzocycloheptane derivatives

Info

Publication number
GB943604A
GB943604A GB11550/60A GB1155060A GB943604A GB 943604 A GB943604 A GB 943604A GB 11550/60 A GB11550/60 A GB 11550/60A GB 1155060 A GB1155060 A GB 1155060A GB 943604 A GB943604 A GB 943604A
Authority
GB
United Kingdom
Prior art keywords
compounds
acid
dibenzo
reduced
cycloheptadienone
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
GB11550/60A
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.)
Koninklijke Pharmaceutische Fabrieken NV
Original Assignee
Koninklijke Pharmaceutische Fabrieken NV
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 Koninklijke Pharmaceutische Fabrieken NV filed Critical Koninklijke Pharmaceutische Fabrieken NV
Publication of GB943604A publication Critical patent/GB943604A/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
    • C07D207/04—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
    • C07D207/06—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 radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/33—Polycyclic acids
    • C07C63/331—Polycyclic acids with all carboxyl groups bound to non-condensed rings
    • 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
    • C07D211/40—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

943,604. Dibenzocycloheptane derivatives. KONINKLIJKE PHARMACEUTISCHE FABRIEKEN V/H BROCADES-STHEEMAN & PHARMACIA N.V. April 1, 1960 [April 1, 1959], No. 11550/60. Heading C2C. The invention comprises compounds of the formula: (wherein R 1 and R 2 are hydrogen or halogen atoms or alkyl groups having not more than 4 carbon atoms, provided that not more than one is a hydrogen atom, and X is -CH 2 -CH 2 - or -CH=CH-) and the preparation of the compound wherein X is an ethylene group by cyclizing compounds of the formula: and reducing the resulting ketones to the corresponding alcohols. The preferred cyclizing agent is polyphosphoric acid, or the cyclization may be effected by converting the acid to the corresponding halide and ring-closing this with a Friedel Crafts catalyst such as anhydrous aluminium chloride. The reduction is preferably effected with sodium amalgum and ethanol. The compounds wherein X is a vinylene group are preferably obtained from the compounds wherein X is an ethylene group by conventional method. In examples (1) 1-p-tolyl-2-(o-carboxyphenyl)- ethane is cyclized to 3-methyl-dibenzo-(a,d)-1 À4- cycloheptadienone-(5) and this is reduced to the 5-ol; (2) 1-(p-chlorophenyl)-2-(o-carboxyphenyl)- ethane is converted to the acid chloride, this is cyclized to 3-chloro-dibenzo-(a,d)-1 À4-cycloheptadienone-(5) and this is reduced to the 5-ol; and (3) the intermediate 5-one of (1) is brominated with N-bromo-succinimide to give a monobromo compound: this is dehydrohalogenated by heating with pyridine to give 3-methyl-dibenzo-(a,c)-1 :3:5- cycloheptatrienone-(5), and this is reduced to the 5-ol. Compounds of the second general formula above are prepared by condensing a phenylacetic acid with a phthalic anhydride with concurrent decarboxylation, saponifying the reaction product, and reducing the resulting enol with hydriodic acid and phosphorus. The dibenzocycloheptane derivatives of the invention, which are stated to have a biocidal activity, may be made up into pharmaceutical preparations with suitable carriers. Specification 943,603 is referred to.
GB11550/60A 1959-04-01 1960-04-01 Dibenzocycloheptane derivatives Expired GB943604A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL237663 1959-04-01
US277013A US3209007A (en) 1959-04-01 1963-04-30 (dibenzo (a, d) 1, 4-cycloheptene-5-yloxy) amines

Publications (1)

Publication Number Publication Date
GB943604A true GB943604A (en) 1963-12-04

Family

ID=31497751

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11550/60A Expired GB943604A (en) 1959-04-01 1960-04-01 Dibenzocycloheptane derivatives

Country Status (6)

Country Link
US (1) US3209007A (en)
CH (2) CH400108A (en)
DE (1) DE1470127A1 (en)
DK (1) DK106732C (en)
FR (1) FR3745M (en)
GB (1) GB943604A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1091910A (en) * 1964-08-18 1967-11-22 Koninklijke Pharma Fab Nv New dibenzocycloheptenylamines
US4569944A (en) * 1984-06-21 1986-02-11 Warner-Lambert Company Dibenzosuberone as a non-steroidal anti-inflammatory compound and compositions thereof

Also Published As

Publication number Publication date
DE1470127A1 (en) 1969-05-08
US3209007A (en) 1965-09-28
FR3745M (en) 1965-12-13
CH400108A (en) 1965-10-15
CH410931A (en) 1966-04-15
DK106732C (en) 1967-03-13

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