GB1268070A - A novel tetrahydrobenzazepine derivative, processes for its production and composition containing same - Google Patents

A novel tetrahydrobenzazepine derivative, processes for its production and composition containing same

Info

Publication number
GB1268070A
GB1268070A GB3975569A GB3975569A GB1268070A GB 1268070 A GB1268070 A GB 1268070A GB 3975569 A GB3975569 A GB 3975569A GB 3975569 A GB3975569 A GB 3975569A GB 1268070 A GB1268070 A GB 1268070A
Authority
GB
United Kingdom
Prior art keywords
give
formula
reacting
acid addition
pharmaceutically acceptable
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
GB3975569A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB1268070A publication Critical patent/GB1268070A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,268,070. Benzazepine derivative. J. R. GEIGY A.G. 8 Aug., 1969 [9 Aug., 1968], No. 39755/69. Addition to 1,221,324. Heading C2C. The novel compound 2-methyl-7-chloro- 2,3,4,5 - tetrahydro - 1H - 3 - benzazepine of Formula I: and its pharmaceutically acceptable acid addition salts, are prepared by treating a compound of Formula II: wherein X is chlorine, bromine or iodine, or an inorganic acid addition salt thereof, with a Lewis acid, preferably at temperatures between 100‹ and 300‹ C., and isolating the product of Formula I from the reaction mixture, and, if desired, converting this product into a pharmaceutically acceptable acid addition salt. 1 - (p - Chlorophenyl) - 2 - (2 - chloroethylamino)-propane hydrochloride is prepared by reacting chlorobenzene with propionic acid anhydride to give p-chloropropiophenone, reacting this with sodium borohydride to give 1-(pchlorophenyl)-propanol, treating this with sodium hydrogen sulphate to give p-chloro-#-methylstyrene, reacting this with ethyleneimine to give 1 - (p - chlorophenyl - 2 - (1 - aziridinyl) - propane, and reacting this with hydrogen chloride. Pharmaceutical compositions having an anorexigenic effect, for oral, rectal or parenteral administration, comprise the novel compound of Formula I, or a pharmaceutically acceptable acid addition salt thereof, together with a carrier.
GB3975569A 1968-08-09 1969-08-08 A novel tetrahydrobenzazepine derivative, processes for its production and composition containing same Expired GB1268070A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US75138168A 1968-08-09 1968-08-09

Publications (1)

Publication Number Publication Date
GB1268070A true GB1268070A (en) 1972-03-22

Family

ID=25021727

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3975569A Expired GB1268070A (en) 1968-08-09 1969-08-08 A novel tetrahydrobenzazepine derivative, processes for its production and composition containing same

Country Status (6)

Country Link
AT (1) AT289812B (en)
DE (1) DE1940512A1 (en)
ES (1) ES370334A2 (en)
FR (1) FR2015400A6 (en)
GB (1) GB1268070A (en)
NL (1) NL6912141A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2016136A1 (en) * 1970-04-04 1971-10-14 C H Boehnnger Sohn, 6507 Ingel heim New 7 acyl 1,2,4,5 tetrahydro (3H) 3 benzazepine
DE2207430C3 (en) * 1972-02-14 1982-05-13 Pennwalt Corp., 19102 Philadelphia, Pa. 1,2,4,5-Tetrahydro-3H-3-benzazepine, a process for their preparation and a pharmaceutical agent containing them

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2520264A (en) * 1947-08-26 1950-08-29 Maltbie Lab Inc Substituted 3, 1-benz-2, 3, 4, 5-tetrahydroazepines
CH481110A (en) * 1967-02-17 1969-11-15 Geigy Ag J R Process for the preparation of 1,2,4,5-tetrahydro-3-azepines

Also Published As

Publication number Publication date
DE1940512A1 (en) 1970-10-01
NL6912141A (en) 1970-02-11
FR2015400A6 (en) 1970-04-24
AT289812B (en) 1971-05-10
ES370334A2 (en) 1971-04-16

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