GB858186A - Novel dibenzoheptaenes and salts thereof and a process for the manufacture of same - Google Patents

Novel dibenzoheptaenes and salts thereof and a process for the manufacture of same

Info

Publication number
GB858186A
GB858186A GB10089/59A GB1008959A GB858186A GB 858186 A GB858186 A GB 858186A GB 10089/59 A GB10089/59 A GB 10089/59A GB 1008959 A GB1008959 A GB 1008959A GB 858186 A GB858186 A GB 858186A
Authority
GB
United Kingdom
Prior art keywords
alkyl
dimethylaminopropyl
chloro
hydroxy
aminoalkyl
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
GB10089/59A
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 GB858186A publication Critical patent/GB858186A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
    • C07C63/72—Polycyclic acids

Abstract

The invention comprises 5-hydroxy-5-aminoalkyl-dibenzo-cyclohepta di (and tri) enes and their acid addition and quaternary salts having a nucleus of the formula: <FORM:0858186/IV(b)/1> wherein the broken line denotes an optional double bond, the 5-aminoalkyl group being an alkyl group of more than 2 carbon atoms, e.g. propyl, bearing one or more di-substituted amino groups (for example a dialkylamino group or a heterocyclic amino group in which the two alkyl groups are joined directly or through a hetero-atom to form a 5-or 6-membered ring such as a piperidine, morpholine or thiamorpholine ring) and optionally containing one or more alkyl, alkoxy and/or halogeno substituents on the dibenzoheptaene ring. The compounds are prepared by condensing a dibenzocycloheptadi (or tri) enone-(5) with a saturated aminoalkyl organo-metallic compound, hydrolysing the condensation product and if desired converting from a salt to a free base or from a free base to an acid addition or quaternary salt. The organo-metallic compound may suitably be a magnesium-, lithium- or zinc-organic compound. The compounds are used pharmaceutically, suitably in the form of salts such as hydrohalides, sulphates, phosphates, acetates, tartrates, maleates, citrates, lactates, oxalates or ethanesulphonates or quaternary salts derived from alkyl or aralkyl halides or dialkyl sulphates. Preferred products include the 5-dimethylaminopropyl, 5-piperidinopropyl and 3-chloro-5-dimethylaminopropyl-, 5-hydroxy-dibenzocyclo - heptadienes and 5-hydroxy-5-dimethylaminopropyl-dibenzocycloheptatriene. Dibenzocycloheptadienones used as starting materials are prepared by reducing the corresponding benzal-phthalides to give a dibenzylorthocarboxylic acid, e.g. 4-chlorodibenzyl-(21)-carboxylic acid, which is then cyclized to the desired heptadienone, e.g. 3-chloro-dibenzocyclo-heptadienone. The corresponding trienones are made by brominating the dibenzocycloheptadienones and splitting off hydrogen bromide. 4-Chloro-benzalphthalide is made by heating phthalic anhydride with 4-chlorophenyl-acetic acid and sodium acetate. Specifications 858,187 and 858,188 are referred to.
GB10089/59A 1958-04-03 1959-03-24 Novel dibenzoheptaenes and salts thereof and a process for the manufacture of same Expired GB858186A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH858186X 1958-04-03

Publications (1)

Publication Number Publication Date
GB858186A true GB858186A (en) 1961-01-11

Family

ID=4542879

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10089/59A Expired GB858186A (en) 1958-04-03 1959-03-24 Novel dibenzoheptaenes and salts thereof and a process for the manufacture of same

Country Status (2)

Country Link
GB (1) GB858186A (en)
MY (1) MY6500159A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3126411A (en) * 1964-03-24 Processes and intermediates for pre-
US3167541A (en) * 1961-04-27 1965-01-26 Koninklijke Pharma Fab Nv 5-(diazacycloalkyl)-10, 11-dihydrodibenzocycloheptenes
US3257404A (en) * 1962-06-15 1966-06-21 Rhone Poulenc Sa Piperazine derivatives of dibenzo[a,d] cycloheptadiene
US3275689A (en) * 1962-08-13 1966-09-27 Merck & Co Inc 3-alkylsulfonyl-5-(tertiaryaminopropylidene)-and 5-hydroxy-5-(tertiaryaminopropyl)-5h-dibenzo[a, d] cycloheptenes
US3281469A (en) * 1962-08-10 1966-10-25 Lilly Co Eli Process for preparing 5-hydroxy-5-(3-aminoalkynyl) dibenzo [a, d] cyclohepta [1, 4] denes
US3309404A (en) * 1962-04-04 1967-03-14 Merck & Co Inc Derivatives of dibenzocycloheptenes and a process for their preparation
US3366635A (en) * 1963-04-24 1968-01-30 Schering Corp Aza-5h-dibenzo-[a,d]-(cycloheptenes and cycloheptene-5-ones) and the corresponding 10, 11-dihydro derivatives thereof
US3384663A (en) * 1959-03-27 1968-05-21 Hoffmann La Roche 5-tertiaryaminoalkylidene dibenzocycloheptadiene compounds, and salts thereof

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3126411A (en) * 1964-03-24 Processes and intermediates for pre-
US3384663A (en) * 1959-03-27 1968-05-21 Hoffmann La Roche 5-tertiaryaminoalkylidene dibenzocycloheptadiene compounds, and salts thereof
US3167541A (en) * 1961-04-27 1965-01-26 Koninklijke Pharma Fab Nv 5-(diazacycloalkyl)-10, 11-dihydrodibenzocycloheptenes
US3309404A (en) * 1962-04-04 1967-03-14 Merck & Co Inc Derivatives of dibenzocycloheptenes and a process for their preparation
US3257404A (en) * 1962-06-15 1966-06-21 Rhone Poulenc Sa Piperazine derivatives of dibenzo[a,d] cycloheptadiene
US3281469A (en) * 1962-08-10 1966-10-25 Lilly Co Eli Process for preparing 5-hydroxy-5-(3-aminoalkynyl) dibenzo [a, d] cyclohepta [1, 4] denes
US3275689A (en) * 1962-08-13 1966-09-27 Merck & Co Inc 3-alkylsulfonyl-5-(tertiaryaminopropylidene)-and 5-hydroxy-5-(tertiaryaminopropyl)-5h-dibenzo[a, d] cycloheptenes
US3366635A (en) * 1963-04-24 1968-01-30 Schering Corp Aza-5h-dibenzo-[a,d]-(cycloheptenes and cycloheptene-5-ones) and the corresponding 10, 11-dihydro derivatives thereof

Also Published As

Publication number Publication date
MY6500159A (en) 1965-12-31

Similar Documents

Publication Publication Date Title
SE7907811L (en) AZETIDINYL COMPOUND FOR THE PREPARATION OF CEFEM COMPOUNDS AND PROCEDURE FOR ITS PREPARATION
GB858186A (en) Novel dibenzoheptaenes and salts thereof and a process for the manufacture of same
ES2006994A6 (en) Process for the preparation of quinoline carboxylic acid derivatives.
AU1572188A (en) Process for the preparation of quinoline carboxylic acids
GB831920A (en) New phenthiazine derivatives and processes for their preparation
GB1125112A (en) New derivatives of diazabicyclo-decane and process for preparing them
GB858188A (en) Novel dibenzocycloheptaenes and salts thereof and a process for the manufacture of same
GB1450452A (en) Derivatives of pyrazolo 3,4-2,3- pyrido 4,5-e- b-benzo-1,5- diazepinones
GB819852A (en) Improvements in or relating to new phenthiazine derivatives and processes for their preparation
GB1412377A (en) Oxazolo- 5,4-d azepines
GB954146A (en) Improvements in or relating to steroid derivatives
GB863699A (en) Hydroxy-alkyl-4-piperazinyl-alkyl-thiaxanthenes
GB1439838A (en) Process for the preparation of diphenylamine and substituted derivatives thereof
US3528977A (en) Substituted t-aminophenylalanines
GB1369578A (en) Pharmaceutical compositions containing indole-caboxylic acid derivatives
GB1163876A (en) Pyrazolyl-triazolyl Coumarins
ES430320A1 (en) Amino acid ester
IE33364B1 (en) Pyrimidine carboxylic acid ester derivatives
ES8201522A1 (en) Dibenzo[a,d]cycloheptene derivatives and process for production thereof
GB1282896A (en) New 4-oxo-1,4-dihydro-3-quinolyl-carboxylic acid derivatives and process for their preparation
GB879954A (en) Process for the manufacture of tertiary alkylamine phthalazones
GB783050A (en) Steroid compounds and the preparation thereof
GB1393486A (en) 2,1-benzoxathian-1,1-dioxide-3-carboxamide derivatives methods for their preparation and compositions containing them
GB928317A (en) New cyclopentano-naphthalene derivatives and processes for their production and use
GB1025423A (en) Dibenzocycloheptene derivatives