GB1274262A - Dibenzocycloheptene derivatives - Google Patents

Dibenzocycloheptene derivatives

Info

Publication number
GB1274262A
GB1274262A GB28705/71A GB2870571A GB1274262A GB 1274262 A GB1274262 A GB 1274262A GB 28705/71 A GB28705/71 A GB 28705/71A GB 2870571 A GB2870571 A GB 2870571A GB 1274262 A GB1274262 A GB 1274262A
Authority
GB
United Kingdom
Prior art keywords
compound
methyl
formula
prepared
hydroxy
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
GB28705/71A
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 CH661268A external-priority patent/CH501581A/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1274262A publication Critical patent/GB1274262A/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
    • C07C63/33—Polycyclic acids
    • C07C63/331—Polycyclic acids with all carboxyl groups bound to non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/38—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
    • C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,274,262. 1,5-Disubstituted-dibenzocycloheptene derivatives. F. HOFFMANN-LA ROCHE & CO. A.G. 1 May, 1969 [3 May, 1968], No. 28705/71. Divided out of 1,274,261. Heading C2C. Novel compounds of Formula Ia and Formula Ib wherein R 1 is H or methyl and R<SP>1</SP> is methyl or an acetyl group ketalized by a C 1-7 alkanol or glycol and N-oxides of compounds where R 1 is methyl, are prepared by one of the following methods:- When a compound of Formula Ia in which R 1 represents a methyl group is to be prepared, a corresponding 5H - dibenzo[a,d]cyclohepten-5- one or 10,11 - dihydro - 5H - dibenzo[a,d]cyclohepten-5-one is reacted directly, for example, with 3-dimethylaminopropyl magnesium chloride and the reaction product is subsequently hydrolysed. When a compound of Formula Ia in which R 1 represents a hydrogen atom is to be prepared, it is recommended to use N-methyl- N-benzyl-aminopropyl magnesium chloride as the reagent for the reaction. After completion of the reaction and subsequent hydrolysis, the resulting product is reacted with chloroformic acid ethyl ester and the resulting 5-hydroxy-5- [3 - (N - methyl - N - carbethoxy - amino) - propyl] compound is subsequently hydrolysed, spontaneous decarboxylation occurring with the formation of the corresponding 5-hydroxy-5- (3-methylaminopropyl) compound. Compounds of Formula Ib are obtained, for example, by reacting an appropriate 5H- dibenzo[a,d]cyclohepten-5-one or 10,11-dihydro- 5H - dibenzo[a,d]cyclohepten-5-one with ethyl magnesium bromide and hydrolysing the reaction product. The resulting 5-hydroxy-5-ethyl compound is dehydrated with acetyl chloride and subsequently treated with formic acid and hydrogen peroxide. There results a 5-hydroxy-5- (1-hydroxy-ethyl) compound which is dehydrated with aqueous sulphuric acid to the corresponding 5-acetyl compound. By treatment with formaldehyde and methyl- or dimethylamine hydrochloride there is obtained a 5-(methyl- or dimethylaminopropionyl) compound which, after reduction with sodium borohydride is converted into the corresponding compound of Formula Ib. The compounds of Formulµ Ia and Ib in which R 1 represents a methyl group can be converted by oxidation into the corresponding N-oxides. The oxidation can be carried out, for example, by treatment with hydrogen peroxide in a solvent such as, for example, methanol or ethanol at a temperature of from room temperature up to the boiling point of the oxidation mixture. 1 - Methyl - 5 - keto - dibenzocycloheptene is prepared by dehydrogenation of the cycloheptene compound using N-bromo succinimide. 1 - (2 - Methyl - 1,3 - dioxolan - 2 - yl) - 10,11- dihydro - 5H - dibenzocyclohepten - 5 - one is prepared by ketalization of the corresponding 1 -acetyl compound which is obtained by action of Mg diethylmalonate on the 1-chlorocarbonyl compound obtained by preparation of the acid chloride of 1 - carboxy - 10,11 - dihydro - 5H- dibenzocyclohepten-5-one obtained by cyclization of α,α<SP>1</SP>-bis-o-toluic acid prepared by hydrolysis of the dinitrile obtained by treatment of ocyanobenzyl chloride with Gilman alloy. Reference has been directed by the Comptroller to Specifications 986,577 and 858,186.
GB28705/71A 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives Expired GB1274262A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH661268A CH501581A (en) 1968-05-03 1968-05-03 Process for the preparation of tricyclic compounds
GB22175/69A GB1274261A (en) 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives and the manufacture thereof

Publications (1)

Publication Number Publication Date
GB1274262A true GB1274262A (en) 1972-05-17

Family

ID=25699863

Family Applications (4)

Application Number Title Priority Date Filing Date
GB28705/71A Expired GB1274262A (en) 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives
GB28709/71A Expired GB1274266A (en) 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives
GB28706/71A Expired GB1274263A (en) 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives
GB28707/71A Expired GB1274264A (en) 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB28709/71A Expired GB1274266A (en) 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives
GB28706/71A Expired GB1274263A (en) 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives
GB28707/71A Expired GB1274264A (en) 1968-05-03 1969-05-01 Dibenzocycloheptene derivatives

Country Status (1)

Country Link
GB (4) GB1274262A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995015959A1 (en) * 1993-12-06 1995-06-15 Schering Corporation Tricyclic derivatives and their use in pharmaceuticals
US5464840A (en) * 1993-12-06 1995-11-07 Schering Corporation Tricyclic derivatives, compositions and methods of use

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995015959A1 (en) * 1993-12-06 1995-06-15 Schering Corporation Tricyclic derivatives and their use in pharmaceuticals
US5464840A (en) * 1993-12-06 1995-11-07 Schering Corporation Tricyclic derivatives, compositions and methods of use
US5574173A (en) * 1993-12-06 1996-11-12 Schering Corporation Tricyclic derivatives, compositions and methods of use
US5688805A (en) * 1993-12-06 1997-11-18 Schering Corporation Tricyclic derivatives, compositions and methods of use

Also Published As

Publication number Publication date
GB1274266A (en) 1972-05-17
GB1274263A (en) 1972-05-17
GB1274264A (en) 1972-05-17

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee