GB1235002A - Improvements in or relating to oxazoloisoquinoline derivatives - Google Patents
Improvements in or relating to oxazoloisoquinoline derivativesInfo
- Publication number
- GB1235002A GB1235002A GB38266/68A GB3826668A GB1235002A GB 1235002 A GB1235002 A GB 1235002A GB 38266/68 A GB38266/68 A GB 38266/68A GB 3826668 A GB3826668 A GB 3826668A GB 1235002 A GB1235002 A GB 1235002A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- acid addition
- addition salt
- phenyl
- tetrahydroisoquinoline
- 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
-
- 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
- C07D217/18—Aralkyl radicals
-
- 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
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
1,235,002. 1 - Phenyl - 3 - imino - 1,5,6,10btetrahydro - 3H - oxazolo[4,3-a]isoquinolines. SANDOZ Ltd. 9 Aug., 1968 [25 Aug., 1967; 21 May, 1968], No. 38266/68. Heading C2C. Novel 1 - phenyl - 3 - imino - 1,5,6,10b - tetrahydro - 3H - oxazolo[4,3-a]isoquinolines of the general formula wherein R, R 1 , R 2 and R 3 are each a hydrogen, fluorine or chlorine atom or a trifluoromethyl group, R 4 and R 5 are each a hydrogen, fluorine or chlorine atom or a straight chain C 1-4 alkyl group and R 6 is a hydrogen atom or a straight chain C 1-4 alkyl group, with the provisos (i) that no more than three of R, R 1 , R 2 , R 3 , R 4 and R 5 are other than a hydrogen atom and. (ii) R, R 1 , R 2 and R 3 are such that there is never a trifluoromethyl group on each of two adjacent carbon atoms, the compounds being in free base or acid addition salt form when R 6 is a hydrogen atom and in acid addition salt form when R 6 is an alkyl group, are prepared as follows: (a) obtaining a hydrochloride by reaction of a 1-(α- hydroxybenzyl) - 1,2,3,4 - tetrahydroisoquinoline-2-carboxamide of the general formula with thionyl chloride; (b) obtaining a mixed salt of a compound of the first general formula above wherein R 6 is a hydrogen atom by reaction of an α-phenyl-1,2,3,4-tetrahydroisoquinoline-1-methanol of the general formula with cyanogen bromide and lithium, sodium, potassium or calcium acetate in the presence of an inert organic solvent; (c) obtaining an acid addition salt of a compound of the first general formula above wherein R 6 is a straight chain C 1-4 alkyl group by reaction of an α-phenyl- 1, 2, 3,4-tetrahydroisoquinoline-1-methanol of the general formula wherein R<SP>1</SP> 6 is a straight chain C 1-4 alkyl group, with cyanogen bromide and the acetate of lithium, sodium, potassium or calcium, and reaction of the resulting 1-(α-hydroxybenzyl)- 1,2,3,4 - tetrahydroisoquinoline - 2 - carbonitrile of the general formula with an acid; (d) obtaining a compound of the first general formula above wherein R 6 is a hydrogen atom or an acid addition salt thereof by basifying an acid addition salt of the general formula wherein A is a chlorine or bromine atom or an acetate group, and, when an acid addition salt is required, reacting the resulting compound of the first general formula above wherein R 6 is a hydrogen atom with an acid; and (e) obtaining an acid addition salt of a compound of the first general formula above wherein R 6 is a straight chain C 1-4 alkyl group by basifying and then acidifying the corresponding hydrochloride salt. Pharmaceutical compositions having antidepressant and anorexic activity comprise, as active ingredient, a 1-phenyl-3-imino-1,5,6,10btetrahydro - 3H - oxazolo[4,3-a]isoquinoline of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, the compound being in the form of a said acid addition salt unless R 6 is a hydrogen atom, in association with a pharmaceutically acceptable carrier or diluent, and may be administered orally or parenterally. 1 - (α - Hydroxybenzyl) - 1,2,3,4 - tetrahydroisoquinoline-2-carboxamides of the second general formula above are prepared by treatment of an α - phenyl - 1,2,3,4 - tetrahydroisoquinoline- 1-methanol of the general formula under acidic conditions with an alkali metal isocyanate in an inert organic solvent. α - Phenyl - 1,2,3,4 - tetrahydroisoquinoline- 1 -methanols of the general formula immediately above are prepared (a) by cyclization of an N- phenethyl - 2 - phenyl - acetamide of the general formula with phosphorus pentoxide in an inert solvent at 75-150 C., treatment of the resulting 1 - benzyl - 3,4 - dihydroisoquinoline of the general formula with air or oxygen and reduction of the obtained 1 - benzoyl - 3,4 - dihydroisoquinoline of the general formula at 20-50 C. in an inert solvent with hydrogen in the presence of a platinum catalyst; or (b) by reaction of a 1-cyano-2-benzoyl-1,2-dihydroisoquinoline with a lithium compound and a benzaldehyde derivative, followed by catalytic hydrogenation.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US66321867A | 1967-08-25 | 1967-08-25 | |
US73095768A | 1968-05-21 | 1968-05-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1235002A true GB1235002A (en) | 1971-06-09 |
Family
ID=27098701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38266/68A Expired GB1235002A (en) | 1967-08-25 | 1968-08-09 | Improvements in or relating to oxazoloisoquinoline derivatives |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS4826019B1 (en) |
BE (1) | BE719921A (en) |
CH (2) | CH498144A (en) |
DE (1) | DE1795189A1 (en) |
ES (3) | ES357503A1 (en) |
FR (2) | FR1587682A (en) |
GB (1) | GB1235002A (en) |
SE (1) | SE333144B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51147818A (en) * | 1975-06-11 | 1976-12-18 | Aisin Seiki Co Ltd | Seat slide adjusting device |
DE102007006795B3 (en) * | 2007-02-12 | 2008-04-03 | Takraf Gmbh | Dust-free bulk material transfer device e.g. for ship loader, has annular seal provided between transfer chute and rotational cute |
-
1968
- 1968-08-02 CH CH1157968A patent/CH498144A/en not_active IP Right Cessation
- 1968-08-02 CH CH1327170A patent/CH498145A/en not_active IP Right Cessation
- 1968-08-09 GB GB38266/68A patent/GB1235002A/en not_active Expired
- 1968-08-20 SE SE1118068A patent/SE333144B/en unknown
- 1968-08-21 DE DE19681795189 patent/DE1795189A1/en active Pending
- 1968-08-23 ES ES357503A patent/ES357503A1/en not_active Expired
- 1968-08-23 FR FR1587682D patent/FR1587682A/fr not_active Expired
- 1968-08-23 BE BE719921D patent/BE719921A/xx unknown
- 1968-11-21 FR FR174697A patent/FR8101M/fr not_active Expired
-
1969
- 1969-11-14 ES ES373529A patent/ES373529A1/en not_active Expired
-
1971
- 1971-04-01 ES ES389793A patent/ES389793A1/en not_active Expired
- 1971-09-17 JP JP7185671A patent/JPS4826019B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
ES357503A1 (en) | 1970-03-16 |
FR1587682A (en) | 1970-03-27 |
JPS4826019B1 (en) | 1973-08-03 |
BE719921A (en) | 1969-02-24 |
ES389793A1 (en) | 1974-03-01 |
CH498145A (en) | 1970-10-31 |
SE333144B (en) | 1971-03-08 |
FR8101M (en) | 1970-07-27 |
CH498144A (en) | 1970-10-31 |
DE1795189A1 (en) | 1972-01-05 |
ES373529A1 (en) | 1972-06-01 |
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