GB1054095A - - Google Patents
Info
- Publication number
- GB1054095A GB1054095A GB2507065A GB2507065A GB1054095A GB 1054095 A GB1054095 A GB 1054095A GB 2507065 A GB2507065 A GB 2507065A GB 2507065 A GB2507065 A GB 2507065A GB 1054095 A GB1054095 A GB 1054095A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- general formula
- hydrogen
- group
- compounds
- 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
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1,054,095. Isoquinoline derivatives. F. HOFFMANN-LA ROCHE & CO. A.G. June 14, 1965 [June 16, 1964], No. 25070/65. Heading C2C. New 7-oxo-cyclopent[i,j]-isoquinoline derivatives of general formula wherein R 1 and R 2 represent hydrogen or an alkyl or alkanoyl group of up to seven carbon atoms, or together represent the methylene group, and R 3 represents hydrogen or an alkyl, alkenyl group of up to seven carbon atoms, aralkyl or cycloalkyl alkyl group or the acyl group derived from a lower aliphatic or aromatic carboxylic acid, and acid addition salts, quaternary salts and quaternary bases thereof, are prepared by cyclizing a tetrahydroisoquinoline compound of general formula wherein R 1 , R 2 and R 3 have the above significance and X represents carboxyl, halocarbonyl, alkoxycarbonyl, aryloxycarbonyl or arylkoxycarbonyl group, or an acid addition salt, a quarternary salt or a quaternary base thereof. for example using polyphosphoric, concentrated phosphoric, hydrofluoric, or sulphuric acid at elevated temperatures in the case where X represents a carbonyl group, and by using a Friedel-Crafts type catalyst such as an aluminium trihalide, boron trifluoride or zinc chloride in the case where X represents halo-carbonyl and, when required, converting the product into an acid-addition, quaternary salt or quaternary base thereof. If required, R<SP>1</SP> and/or R<SP>2</SP> may be modified in that an alkyl group may be replaced by hydrogen, for example by reaction with hydrobromic acid, and hydrogen values may be converted into alkanoyl values, for example by reaction with an acid anhydride. In addition, when R<SP>3</SP> is hydrogen, the hydrogen may be replaced by any other value for R<SP>3</SP>, for example by reaction with the appropriate organo-halide or anhydride to introduce a benzyl, allyl, cyclopropylmethyl, acetyl or 4-chloro-benzoyl group at the 1-position. Epoxy compounds of the general formula wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> have the above significance and R<SP>4</SP> is hydrogen, alkoxycarbonyl, aryloxycarbonyl or aralkoxycarbonyl, are prepared by reacting the compounds of the first general formula above with a trimethylsulphonium- or trimethylsulphoxonium halide in the presence of a base, a halo-acetic acid alkyl, aryl or aralkyl ester in the presence of a base, or diazomethane. Compounds of the general formula wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> have the above significance and R<SP>5</SP> is alkyl, are prepared by reacting the compounds of the first general formula above with a triphenylphosphonium compound having a cation of the formula wherein R<SP>5</SP> has the above significance. 7.Formyl compounds of the general formula wherein R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> have the above significance, are prepared by treating the above epoxy compounds with a Lewis acid, a strong mineral acid or trifluoro-acetic acid when R<SP>4</SP> is hydrogen, or with a strong base when R<SP>4</SP> is other than hydrogen, or by treating the compounds of the previous general formula with a strong mineral acid or a Lewis acid. 1 - Carboxymethyl - 2 - methyl - 6,7 - dimethoxy - 1,2,3,4 - tetrahydro - isoquinoline hydrochloride is obtained by reacting 1-ethoxycarbonylmethyl - 6,7 - dimethoxy 1,2,3,4-tetrahydroisoquinoline with formic acid and formaldehyde and treating the reaction product with aqueous hydrochloric acid. 1 - Carboxymethyl - 6,7 - dimethoxy - 1,2,3,4- tetrahydro-isoquinoline hydrochloride is obtained by steam distilling the corresponding 1-methoxycarbonylmethyl compound in the presence of hydrochloric acid. Pharmaceutical compositions having blood pressure lowering activity and also analgesic, antiphlogistic, µdema-inhibiting and antipyretic action, and which can be administered enterally, or parenterally in the form of tablets, dragees, suppositories, or capsules, or as solutions, suspensions, or emulsions, contain a compound of the first general formula above, as the active ingredient.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH786164A CH446341A (en) | 1964-06-16 | 1964-06-16 | Process for the preparation of cyclopent (ij) isoquinoline derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1054095A true GB1054095A (en) | 1967-01-14 |
Family
ID=4331519
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2507065A Expired GB1054095A (en) | 1964-06-16 | 1965-06-14 |
Country Status (7)
Country | Link |
---|---|
BE (1) | BE665445A (en) |
CH (1) | CH446341A (en) |
DE (1) | DE1545945A1 (en) |
ES (1) | ES314222A1 (en) |
FR (2) | FR1443504A (en) |
GB (1) | GB1054095A (en) |
NL (1) | NL6507700A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4930759A (en) * | 1988-05-25 | 1990-06-05 | Potter Arthur C | Cutting board |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4198414A (en) * | 1977-12-29 | 1980-04-15 | A. H. Robins Company, Inc. | Compounds and methods for treating diabetic complications |
-
1964
- 1964-06-16 CH CH786164A patent/CH446341A/en unknown
-
1965
- 1965-05-14 DE DE1965H0056028 patent/DE1545945A1/en active Pending
- 1965-06-14 GB GB2507065A patent/GB1054095A/en not_active Expired
- 1965-06-15 BE BE665445D patent/BE665445A/xx unknown
- 1965-06-15 ES ES0314222A patent/ES314222A1/en not_active Expired
- 1965-06-15 FR FR20760A patent/FR1443504A/en not_active Expired
- 1965-06-15 FR FR20761A patent/FR4532M/fr not_active Expired
- 1965-06-16 NL NL6507700A patent/NL6507700A/xx unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4930759A (en) * | 1988-05-25 | 1990-06-05 | Potter Arthur C | Cutting board |
Also Published As
Publication number | Publication date |
---|---|
CH446341A (en) | 1967-11-15 |
FR4532M (en) | 1966-11-28 |
DE1545945A1 (en) | 1969-12-11 |
ES314222A1 (en) | 1966-04-01 |
BE665445A (en) | 1965-12-15 |
FR1443504A (en) | 1966-06-24 |
NL6507700A (en) | 1965-12-17 |
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