GB1017696A

GB1017696A – Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenes
– Google Patents

GB1017696A – Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenes
– Google Patents
Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenes

Info

Publication number
GB1017696A

GB1017696A
GB3514262A
GB3514262A
GB1017696A
GB 1017696 A
GB1017696 A
GB 1017696A
GB 3514262 A
GB3514262 A
GB 3514262A
GB 3514262 A
GB3514262 A
GB 3514262A
GB 1017696 A
GB1017696 A
GB 1017696A
Authority
GB
United Kingdom
Prior art keywords
dibenzo
cyclohepten
dihydro
compound
radical
Prior art date
1961-09-25
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
GB3514262A
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.)

Merck and Co Inc

Original Assignee
Merck and Co Inc
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.)
1961-09-25
Filing date
1962-09-14
Publication date
1966-01-19

1962-09-14
Application filed by Merck and Co Inc
filed
Critical
Merck and Co Inc

1966-01-19
Publication of GB1017696A
publication
Critical
patent/GB1017696A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

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

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System

C07F1/02—Lithium compounds

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System

C07F1/08—Copper compounds

Abstract

The invention comprises substituted 5H-dibenzo[a,d]cycloheptene and their 10,11-dihydro derivatives which compounds have the general formulae wherein Z represents -CH2CH2CH2- or -C­CCH2-which may be further substituted by a C1-C4 alkyl radical, each of R and R1 represents a C1-C6 alkyl radical or a cycloalkyl, phenyl or benzyl radical provided that when R and R1 are other than alkyl radicals the total number of carbon atoms in R and R1 does not exceed 9 and provided further that when Z is the radical -CH2CH2CH2-which radical may by further substituted by a C1-C4 alkyl radical and R and R1 are both alkyl radicals they are linked together through a nitrogen atom to form a 1-lower alkyl-4-piperazinyl radical, and when Z is the radical -C­CH2-which radical may be further substituted with a C1-C4 alkyl radical, R and R1 may be linked together through a carbon, nitrogen or oxygen atom to form a 1-piperidyl, 4-morpholinyl, 1-pyrrolidyl or 1 – (C1- 4 alkyl) – 4 – piperazinyl ring, and each of X and X1 represents a hydrogen or a halogen atom or a C1- 4 alkoxy, C1- 4 alkylmercapto, C1- 4 alkylsulphonyl or C2- 8 dialkylsulphamoyl group and acid addition salts thereof; and a process for the preparation of compounds of the above general formulae wherein Z represents -CH2CH2CH2- or -C­CCH2-which may be further substituted by a C1-C4 alkyl radical, and each of R and R1 is a C1-C6 alkyl radical or a cycloalkyl, phenyl or benzyl radical provided that when R and R1 are other than alkyl radicals the total number of carbon atoms in R and R1 does not exceed 9 and provided further that when R and R1 are both alkyl radicals, they may be linked together through carbon, nitrogen or oxygen atoms to form a 1-piperidyl, 4-morpholinyl, 1-pyrrolidyl or 1-C1- 4 alkyl-4-piperazinyl ring, by reacting the required 5-halo-substituted 5H-dibenzo[a,d]cycloheptene or 10,11-dihydro derivative thereof with the required organo-metal compound of the formula wherein Y represents lithium or Hal-Mg. Acid addition salts of the compound defined above are also mentioned. Pharmaceutical compositions useful as anti-depressants contain as the active ingredients the substituted 5H-dibenzo[a,d]cycloheptenes and their 10,11-dihydro derivatives defined above. The compositions may be administered in the form of powders, capsules, tablets, elixirs, solutions or aqueous suspensions. 5 – Chloro – 3 – methylmercapto – 5H – dibenzo[a,d]cycloheptene is prepared by reacting methyl mercaptan and cuprous chloride, reacting the resulting cuprous methyl mercaptide with 3-bromo – 5H – dibenzo[a,d]cyclohepten – 5 – one to form 3 – methylmercapto – 5H – dibenzo[a,d]-cyclohepten-5-one, reducing this compound with potassium borohydride to form 3-methyl-mercapto – 5H – dibenzo[a,d]cyclohepten – 5 – ol, treating this compound with hydrogen chloride to form the desired corresponding 5-chloro compound. 5 – Chloro – 3 – dimethylsulphamoyl – 5H – dibenzo[a,d]cyclohepten is prepared by reacting 3 – bromo – 10,11 – dihydro – 5H – dibenzo[a,d]-cyclohepten-5-one with fluosulphonic acid to form 3 – bromo – 7 – fluorosulphonyl – 10,11 – dihydro – 5H – dibenzo[a,d]cyclohepten – 5 – one, treating this compound with dimethylamine to form 3 – bromo – 7 – dimethylsulphamoyl – 10,11 -dihydro – 5H – dibenzo[a,d]cyclohepten – 5 – one, hydrogenating this compound in the presence of palladium on charcoal to form 3-dimethylsulphamoyl – 10,11 – dihydro – 5H – dibenzo[a,d]-cyclohepten-5-one, treating this compound with N-bromosuccinimide and benzoyl peroxide to form 3 – dimethylsulphamoyl – 5H – dibenzo[a,d]-cyclohepten-3-one, reducing this compound with potassium borohydride to form 3-dimethylsulphamoyl – 5H – dibenzo[a,d]cyclohepten – 5 – ol, and treating this compound with hydrogen chloride to form the desired 5-chloro compound. 5 – Chloro – 3 – dimethylsulphamoyl – 10,11 -dihydro – 5H – dibenzo[a,d]cycloheptene is prepared by reducing 3-dimethylsulphamoyl-10,11-dihydro – 5H – dibenzo[a,d]cyclohepten-5-one with potassium borohydride and treating the resulting 3 – dimethylsulphamoyl – 10,11 – dihydro – 5H – dibenzo[a,d]cyclohepten – 5 – ol with hydrogen chloride. Organo-metal compounds of the general formula wherein Y represents lithium or Hal-Mg in which Hal is a halogen, preferably chlorine or bromine, and R, R1 and Z have the significance indicated in the first paragraph above, are prepared by the usual methods from magnesium and the required organo-halides, and from phenyl-lithium and the required substituted hydrocarbon. Reference has been directed by the Comptroller to Specifications 858,188 and 975,465.

GB3514262A
1961-09-25
1962-09-14
Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenes

Expired

GB1017696A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US14022261A

1961-09-25
1961-09-25

Publications (1)

Publication Number
Publication Date

GB1017696A
true

GB1017696A
(en)

1966-01-19

Family
ID=22490268
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB3514262A
Expired

GB1017696A
(en)

1961-09-25
1962-09-14
Substituted 5h-dibenzo[a, d]cycloheptenes and 10,11-dihydro-5h-dibenzo[a, d]cycloheptenes

Country Status (2)

Country
Link

AT
(1)

AT244323B
(en)

GB
(1)

GB1017696A
(en)

Cited By (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

EP0056617A2
(en)

*

1981-01-16
1982-07-28
F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft
Cycloheptene derivatives, process and intermediates for their preparation, and pharmceuticals containing them

EP0056616A2
(en)

*

1981-01-16
1982-07-28
F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft
Cycloheptene derivatives, process for their preparation, and pharmaceuticals containing them

1962

1962-09-14
GB
GB3514262A
patent/GB1017696A/en
not_active
Expired

1962-09-18
AT
AT742362A
patent/AT244323B/en
active

Cited By (5)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

EP0056617A2
(en)

*

1981-01-16
1982-07-28
F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft
Cycloheptene derivatives, process and intermediates for their preparation, and pharmceuticals containing them

EP0056616A2
(en)

*

1981-01-16
1982-07-28
F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft
Cycloheptene derivatives, process for their preparation, and pharmaceuticals containing them

EP0056616A3
(en)

*

1981-01-16
1982-10-27
F. Hoffmann-La Roche & Co. Aktiengesellschaft
Cycloheptene derivatives, process and intermediates for their preparation, and pharmaceuticals containing them

EP0056617A3
(en)

*

1981-01-16
1982-11-17
F. Hoffmann-La Roche & Co. Aktiengesellschaft
Cycloheptene derivatives, process and intermediates for their preparation, and pharmceuticals containing them

US4513002A
(en)

*

1981-01-16
1985-04-23
Hoffmann-La Roche Inc.
Cycloheptene derivatives

Also Published As

Publication number
Publication date

AT244323B
(en)

1965-12-27

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