GB1181959A - 6,7-Dimethoxy-3,4-Dihydroisoquinoline Derivatives - Google Patents

6,7-Dimethoxy-3,4-Dihydroisoquinoline Derivatives

Info

Publication number
GB1181959A
GB1181959A GB522369A GB522369A GB1181959A GB 1181959 A GB1181959 A GB 1181959A GB 522369 A GB522369 A GB 522369A GB 522369 A GB522369 A GB 522369A GB 1181959 A GB1181959 A GB 1181959A
Authority
GB
United Kingdom
Prior art keywords
general formula
dimethoxy
styryl
rendering
ambient temperature
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
GB522369A
Inventor
Fritz Markwardt
Gottfried Faust Werner Fiedler
Gunther Dietz
Ernst Carstens
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.)
AWD Pharma GmbH and Co KG
Original Assignee
Arzneimittelwerk Dresden GmbH
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 Arzneimittelwerk Dresden GmbH filed Critical Arzneimittelwerk Dresden GmbH
Priority to GB522369A priority Critical patent/GB1181959A/en
Publication of GB1181959A publication Critical patent/GB1181959A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1,181,959. 1 - Styryl - 6,7 - dimethoxy - 3,4 - dihydroisoquinoline derivatives. ARZNEIMITTELWERK DRESDEN VEB. 30 Jan., 1969, No. 5223/69. Heading C2C. Novel 1 - styryl - 6,7 - dimethoxy - 3,4 - dihydroisoquinoline derivatives of the general formula wherein either (a) R 1 is a phenyl radical and R 2 is a hydrogen atom or a methyl radical or (b) R 1 is a p-chlorophenyl radical and R 2 is a hydrogen atom, and physiologically compatible acid addition salts thereof are prepared (i) by cyclization of a compound of the general formula in the presence of a condensation agent of the type used in the Bisohler-Napieralski synthesis; (ii) by cyclization of a compound of the general formula wherein R 5 is an alkyl or phenyl radical; (iii) by mixing a styrene derivative of the general formula with a nitrile of the general formula R 1 CH= CHCN and concentrated sulphuric acid, leaving the mixture to stand for some time at ambient temperature and then heating it to 80-150‹ C., followed by cooling and rendering it alkaline; (iv) by dissolving a styrene derivative of the fourth general formula above in an aromatic hydrocarbon, mixing with at least an equimolar amount of a carboxylic acid amide of the general formula R 1 CH = CHCONH 2 or of an oxime of the general formula R 1 CH = CHCH = NOH, and heating for several hours to 70- 150‹ C. in the presence of a condensation agent, followed by decomposing the condensation agent and rendering the reaction mixture alkaline; and (v) by mixing a phenethyl halide of the general formula wherein Hal is a chlorine or bromine atom, at ambient temperature with a complex of a nitrile of the fifth general formula above with aluminium chloride or tin tetrachloride, heating the reaction mixture for several hours at 80- 160‹ C. and thereafter cooling to ambient temperature and rendering alkaline, followed optionally by salification of the product. N-#-3,4-Dimethoxyphenylethyl - p - chlorocinnamic acid amide is prepared by reaction of homoveratryl amine and p-chlorocinnamic acid chloride. 2 - (21 - Acetylaminopropyl) - 4,5 - dimethoxyphenyl styryl ketone is prepared by condensation of benzaldehyde with 2-(2<SP>1</SP>- acetylaminopropyl) - 4,5 - dimethoxy - acetophenone. Pharmaceutical compositions which are useful for the inhibition of thrombocyte functions comprise, as active ingredient, at least one 1- styryl - 6,7 - dimethoxy - 3,4 - dihydroisoquinoline derivative of the first general formula above or a physiologically compatible acid addition salt thereof, in admixture with a solid or liquid pharmaceutical diluent or carrier.
GB522369A 1969-01-30 1969-01-30 6,7-Dimethoxy-3,4-Dihydroisoquinoline Derivatives Expired GB1181959A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB522369A GB1181959A (en) 1969-01-30 1969-01-30 6,7-Dimethoxy-3,4-Dihydroisoquinoline Derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB522369A GB1181959A (en) 1969-01-30 1969-01-30 6,7-Dimethoxy-3,4-Dihydroisoquinoline Derivatives

Publications (1)

Publication Number Publication Date
GB1181959A true GB1181959A (en) 1970-02-18

Family

ID=9792025

Family Applications (1)

Application Number Title Priority Date Filing Date
GB522369A Expired GB1181959A (en) 1969-01-30 1969-01-30 6,7-Dimethoxy-3,4-Dihydroisoquinoline Derivatives

Country Status (1)

Country Link
GB (1) GB1181959A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0170524A2 (en) * 1984-08-01 1986-02-05 The Wellcome Foundation Limited Nitrogen containing heterocyclic compounds
WO2001009101A1 (en) * 1999-07-29 2001-02-08 EGIS Gyógyszergyár Rt. Isoquinoline derivatives, pharmaceutical compositions containing the same, and a process for the preparation of the active substance

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0170524A2 (en) * 1984-08-01 1986-02-05 The Wellcome Foundation Limited Nitrogen containing heterocyclic compounds
JPS6187665A (en) * 1984-08-01 1986-05-06 ザ　ウエルカム　フアウンデ−シヨン　リミテツド Di-or tetrahydroisoquinoline derivatives, manufacture and medicinal composition
EP0170524A3 (en) * 1984-08-01 1988-05-25 The Wellcome Foundation Limited Nitrogen containing heterocyclic compounds
US4963562A (en) * 1984-08-01 1990-10-16 Burroughs Wellcome Co Nitrogen containing heterocyclic compounds
US4968698A (en) * 1984-08-01 1990-11-06 Burroughs Wellcome Co. Nitrogen containing heterocyclic compounds
JPH0688903B2 (en) 1984-08-01 1994-11-09 ザ ウエルカム フアウンデ−シヨン リミテツド Di- or tetrahydroisoquinoline derivatives, a process for their preparation, and pharmaceutical compositions containing them
WO2001009101A1 (en) * 1999-07-29 2001-02-08 EGIS Gyógyszergyár Rt. Isoquinoline derivatives, pharmaceutical compositions containing the same, and a process for the preparation of the active substance

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