GB1079520A - Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof - Google Patents

Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof

Info

Publication number
GB1079520A
GB1079520A GB30549/65A GB3054965A GB1079520A GB 1079520 A GB1079520 A GB 1079520A GB 30549/65 A GB30549/65 A GB 30549/65A GB 3054965 A GB3054965 A GB 3054965A GB 1079520 A GB1079520 A GB 1079520A
Authority
GB
United Kingdom
Prior art keywords
group
alkyl
acid addition
together form
manufacture
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
GB30549/65A
Inventor
John Mervyn Osbond
Graham Alwyn Fothergill
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.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
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 Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB30549/65A priority Critical patent/GB1079520A/en
Priority to CH919866A priority patent/CH464922A/en
Priority to CH1597868A priority patent/CH477444A/en
Priority to IL26040A priority patent/IL26040A/en
Priority to DE19661695147 priority patent/DE1695147A1/en
Priority to US563396A priority patent/US3450704A/en
Priority to BR181255/66A priority patent/BR6681255D0/en
Priority to BE684185D priority patent/BE684185A/xx
Priority to ES0329218A priority patent/ES329218A1/en
Priority to NL6610093A priority patent/NL6610093A/xx
Priority to DK373466AA priority patent/DK117704B/en
Priority to FR69810A priority patent/FR5796M/fr
Publication of GB1079520A publication Critical patent/GB1079520A/en
Expired legal-status Critical Current

Links

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
    • 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
    • C07D217/04—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 with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Novel compounds of the formula <FORM:1079520/C2/1> where R is C1- 4 alkyl or H, R1 and R2 are each C1- 4 alkoxy or together form a methylene group, R3 and R4 are each C1- 4 alkyl or together form a -(CH2)3-, -(CH2)4- or buta-1,3-dien-4-yl group, and A is a carbonyl or -CHOH- group, and acid addition salts thereof, are prepared by reacting the appropriate 6,7- or 1,6,7-substituted tetrahydroisoquinoline or an acid addition salt thereof with formaldehyde and a 3,4-substituted acetophenone, and, if desired, reducing the ketone formed with an alkali-metal aluminium- or boro-hydride, or catalytically using a palladium or platinum catalyst. The condensation preferably is performed in an inert organic solvent (e.g. ethanol) under reflux. Pharmaceutical preparations having analgesic and antitussive action contain the above compounds with a conventional carrier, for oral or parenteral administration.
GB30549/65A 1965-07-19 1965-07-19 Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof Expired GB1079520A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
GB30549/65A GB1079520A (en) 1965-07-19 1965-07-19 Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof
CH919866A CH464922A (en) 1965-07-19 1966-06-24 Process for the preparation of tetrahydroisoquinoline derivatives
CH1597868A CH477444A (en) 1965-07-19 1966-06-24 Process for the preparation of tetrahydroisoquinoline derivatives
IL26040A IL26040A (en) 1965-07-19 1966-06-27 Tetrahydroisoquinoline derivatives and process for the manufacture thereof
DE19661695147 DE1695147A1 (en) 1965-07-19 1966-06-28 Process for the preparation of tetrahydroisoquinoline derivatives
US563396A US3450704A (en) 1965-07-19 1966-07-07 Substituted 2 - (3 - aryl - 3 - keto (or 3-hydroxy)-propyl) - 1,2,3,4 - tetrahydroisoquinolines
BR181255/66A BR6681255D0 (en) 1965-07-19 1966-07-13 NEW QUINOLINIC TETRAHYDRO-ISO DERIVATIVES AND A PROCESS FOR ITS MANUFACTURING
BE684185D BE684185A (en) 1965-07-19 1966-07-15
ES0329218A ES329218A1 (en) 1965-07-19 1966-07-16 A procedure for the preparation of tetrahydro-isoquinoline derivatives. (Machine-translation by Google Translate, not legally binding)
NL6610093A NL6610093A (en) 1965-07-19 1966-07-18
DK373466AA DK117704B (en) 1965-07-19 1966-07-19 Analogous process for the preparation of tetrahydroisoquinoline derivatives.
FR69810A FR5796M (en) 1965-07-19 1966-07-19

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB30549/65A GB1079520A (en) 1965-07-19 1965-07-19 Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof

Publications (1)

Publication Number Publication Date
GB1079520A true GB1079520A (en) 1967-08-16

Family

ID=10309382

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30549/65A Expired GB1079520A (en) 1965-07-19 1965-07-19 Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof

Country Status (11)

Country Link
US (1) US3450704A (en)
BE (1) BE684185A (en)
BR (1) BR6681255D0 (en)
CH (1) CH464922A (en)
DE (1) DE1695147A1 (en)
DK (1) DK117704B (en)
ES (1) ES329218A1 (en)
FR (1) FR5796M (en)
GB (1) GB1079520A (en)
IL (1) IL26040A (en)
NL (1) NL6610093A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3903091A (en) * 1970-02-06 1975-09-02 Sumitomo Chemical Co 1,2,3,4-Tetrahydroisoquinoline derivatives
EP2865381A1 (en) * 2006-05-18 2015-04-29 Pharmacyclics, Inc. ITK inhibitors for treating blood cell malignancies

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT190517B (en) * 1954-06-22 1957-07-10 Wander Ag Dr A Process for the preparation of new, substituted tetrahydroisoquinoline compounds
GB1032054A (en) * 1963-07-19 1966-06-08 Roche Products Ltd Substituted isoquinoline and piperazine derivatives and a process for the manufacture thereof

Also Published As

Publication number Publication date
BE684185A (en) 1967-01-16
BR6681255D0 (en) 1973-12-26
DK117704B (en) 1970-05-25
FR5796M (en) 1968-02-12
ES329218A1 (en) 1967-08-16
US3450704A (en) 1969-06-17
NL6610093A (en) 1967-01-20
CH464922A (en) 1968-11-15
DE1695147A1 (en) 1970-12-17
IL26040A (en) 1970-04-20

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