GB1079520A - Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereof - Google Patents
Novel tetrahydro-isoquinoline derivatives and a process for the manufacture thereofInfo
- 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
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.
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)
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)
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 |
-
1965
- 1965-07-19 GB GB30549/65A patent/GB1079520A/en not_active Expired
-
1966
- 1966-06-24 CH CH919866A patent/CH464922A/en unknown
- 1966-06-27 IL IL26040A patent/IL26040A/en unknown
- 1966-06-28 DE DE19661695147 patent/DE1695147A1/en active Pending
- 1966-07-07 US US563396A patent/US3450704A/en not_active Expired - Lifetime
- 1966-07-13 BR BR181255/66A patent/BR6681255D0/en unknown
- 1966-07-15 BE BE684185D patent/BE684185A/xx unknown
- 1966-07-16 ES ES0329218A patent/ES329218A1/en not_active Expired
- 1966-07-18 NL NL6610093A patent/NL6610093A/xx unknown
- 1966-07-19 FR FR69810A patent/FR5796M/fr not_active Expired
- 1966-07-19 DK DK373466AA patent/DK117704B/en unknown
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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