GB1182639A - Novel Tricyclic Amines and a Process for the Manufacture Thereof - Google Patents

Novel Tricyclic Amines and a Process for the Manufacture Thereof

Info

Publication number
GB1182639A
GB1182639A GB50467/67A GB5046767A GB1182639A GB 1182639 A GB1182639 A GB 1182639A GB 50467/67 A GB50467/67 A GB 50467/67A GB 5046767 A GB5046767 A GB 5046767A GB 1182639 A GB1182639 A GB 1182639A
Authority
GB
United Kingdom
Prior art keywords
dibenzo
cycloheptene
general formula
substituted
reaction
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
GB50467/67A
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 GB1182639A publication Critical patent/GB1182639A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • 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
    • 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
    • C07C63/74—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1,182,639. Dibenzo[a,d]cycloheptene derivatives. F. HOFFMANN-LA ROCHE & CO. A.G. 7 Nov., 1967 [8 Nov., 1966; 2 Feb., 1967], No. 50467/67. Heading C2C. Novel dibenzo[a,d]cycloheptene derivatives of the general formula wherein R is a chlorine or fluorine atom, R<SP>1</SP> is a methyl group, R<SP>2</SP> and R<SP>3</SP> are each a chlorine or fluorine atom and X is an ethylene group or a vinylene group which may be substituted by a halogen atom and the broken lines denote optional bonds, and acid addition salts thereof are prepared (i) by reduction or dehydration of a hydroxy compound of the general formula wherein one of Y<SP>1</SP> and Y<SP>2</SP> is a hydrogen atom and the other is a hydroxy group; (ii) reaction of a 5-halo-substituted dibenzo[a,d]cycloheptene of the general formula wherein W is a halogen atom, with a dimethylaminopropyl magnesium halide; or (iii) by treatment of a 5-substituted dibenzo[a,d]cycloheptene of the general formula wherein Z is a halogen atom or a substituted sulphonyloxy residue, with methylamine or dimethylamine; followed optionally by demethylation of a dimethylamino compound by reaction with cyanogen bromide and treatment of the resulting N-cyamo-N-methylamino compound with glacial acetic acid, water and concentrated hydrochloric acid under reflux; and followed optionally by conversion of the basic product into an acid addition salt thereof. 5 - Substituted dibenzo[a,d]cycloheptenes of the fourth general formula above are prepared by reaction of the corresponding dibenzo[a,d]- cyclohepten-5-one with a 3-methoxypropylmagnesium halide, treatment of the resulting 5 - hydroxy - 5 - (3 - methoxypropyl) - dibenzo [a,d]cycloheptene with methanolic hydrogen chloride and reaction of the obtained 5-(3-methoxypropylidene) - dibenzo[a,d]cycloheptene with boron trichloride. Pharmaceutical compositions, having antidepressive, narcosis-potentiating, adrenolytic, sedative, anti-histamine-like and local anaesthetic activity, comprise, as active ingredient, a dibenzo[a,d]cycloheptene derivative of the first general formula above or a pharmaceutically acceptable acid addition salt thereof in association with a compatible pharmaceutical carrier, and may be administered enterally, percutaneously or parenterally.
GB50467/67A 1966-11-08 1967-11-07 Novel Tricyclic Amines and a Process for the Manufacture Thereof Expired GB1182639A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1614466A CH484044A (en) 1966-11-08 1966-11-08 Process for the preparation of tricyclic amines
CH165167 1967-02-02

Publications (1)

Publication Number Publication Date
GB1182639A true GB1182639A (en) 1970-02-25

Family

ID=25688271

Family Applications (2)

Application Number Title Priority Date Filing Date
GB50467/67A Expired GB1182639A (en) 1966-11-08 1967-11-07 Novel Tricyclic Amines and a Process for the Manufacture Thereof
GB40602/69A Expired GB1182640A (en) 1966-11-08 1967-11-07 Tricyclic Compounds

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB40602/69A Expired GB1182640A (en) 1966-11-08 1967-11-07 Tricyclic Compounds

Country Status (12)

Country Link
JP (1) JPS5015791B1 (en)
BE (1) BE706089A (en)
CA (1) CA968351A (en)
CH (1) CH484044A (en)
DE (1) DE1668208C3 (en)
ES (1) ES346885A1 (en)
FR (2) FR1583624A (en)
GB (2) GB1182639A (en)
GR (1) GR37775B (en)
IL (1) IL28854A (en)
NL (1) NL157799B (en)
SE (1) SE356741B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58168318U (en) * 1982-05-06 1983-11-10 株式会社レマン skin cleanser
JPS58188030U (en) * 1982-06-10 1983-12-14 株式会社レマン skin cleanser
JPS58188029U (en) * 1982-06-10 1983-12-14 株式会社レマン skin cleanser

Also Published As

Publication number Publication date
DE1668208B2 (en) 1980-11-06
DE1668208C3 (en) 1981-06-25
FR8358M (en) 1971-02-08
DE1668208A1 (en) 1971-09-02
FR1583624A (en) 1969-11-21
NL6715103A (en) 1968-05-09
NL157799B (en) 1978-09-15
SE356741B (en) 1973-06-04
JPS5015791B1 (en) 1975-06-07
CA968351A (en) 1975-05-27
GB1182640A (en) 1970-02-25
BE706089A (en) 1968-05-06
IL28854A (en) 1972-08-30
ES346885A1 (en) 1969-05-16
CH484044A (en) 1970-01-15
GR37775B (en) 1969-07-14

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Legal Events

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