GB1022940A - Novel substituted quinolines and method of preparing the same - Google Patents
Novel substituted quinolines and method of preparing the sameInfo
- Publication number
- GB1022940A GB1022940A GB4754/65A GB475465A GB1022940A GB 1022940 A GB1022940 A GB 1022940A GB 4754/65 A GB4754/65 A GB 4754/65A GB 475465 A GB475465 A GB 475465A GB 1022940 A GB1022940 A GB 1022940A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- acid
- alkylamine
- toxic
- 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
- C07D221/04—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
New quinoline derivatives of the Formula I <FORM:1022940/C2/1> and non-toxic, acid-addition salts thereof, wherein R represents hydrogen, chlorine, bromine, trifluoromethyl, C1-4 alkyl or C1-C4 alkoxy: A represents a C2-C6 alkylene radical; R1 represents a mono-C1-C4-alkylamine, di-C1-C4-alkylamine, morpholino, piperidino, piperazino or pyrrolidino and n is 3 or 4, produced by reacting at least one molecular proportion of a compound of the formula XAR1, wherein X is halogen, with one molecular proportion of a compound of the Formula II <FORM:1022940/C2/2> in the presence of sodium hydride and an inert solvent and recovering the product from the reaction mixture and, if desired, reacting the free base so obtained with an acid. The compounds of Formula I may also be obtained by refluxing an amine of formula R1H with a compound of the Formula III <FORM:1022940/C2/3> in the presence of a solvent. Reactants of the Formula II above may be prepared by refluxing equimolar proportions of cyclohextanone or cyclooctanone and an R substituted 2-aminobenzoic acid in an inert solvent with continuous removal of water. The quinoline derivatives of Formula I are pharmaceutically active and can be employed with non-toxic, pharmaceutical liquid or solid carriers in the form of tablets, solutions, suspensions or emulsions as anti-hypotensive agents, anti-depressants and as tranquillizers. These compositions may be employed orally, intravenously or intramuscularly.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34229364A | 1964-02-03 | 1964-02-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1022940A true GB1022940A (en) | 1966-03-16 |
Family
ID=23341195
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4754/65A Expired GB1022940A (en) | 1964-02-03 | 1965-02-03 | Novel substituted quinolines and method of preparing the same |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE658695A (en) |
CH (1) | CH435279A (en) |
DE (1) | DE1232148B (en) |
ES (1) | ES308636A1 (en) |
FR (1) | FR4483M (en) |
GB (1) | GB1022940A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4108998A (en) | 1976-11-08 | 1978-08-22 | American Home Products Corp. | Furo[3,4-b]quinoline derivatives and pharmaceutical compositions and methods employing them |
US4800203A (en) * | 1987-09-24 | 1989-01-24 | Hoechst-Roussel Pharmaceuticals, Inc. | Pyrrolo(1,2-b)cinnolines |
US4897400A (en) * | 1987-02-13 | 1990-01-30 | Hoeschst-Roussel Pharmaceuticals, Inc. | 9-amino-1,4-ethano-1,2,3,4-tetrahydroacridine and related compounds useful for incresing the cholinergic function in a mammal |
US4916135A (en) * | 1989-05-08 | 1990-04-10 | Hoechst Roussel Pharmaceuticals Inc. | N-heteroaryl-4-quinolinamines |
US5013741A (en) * | 1987-09-08 | 1991-05-07 | Hoechst-Roussel Pharmaceuticals Incorporated | N-[substituted alkylidene]-1,2,3,4-tetrahydro-9-acridinamines useful for enhancing the cholinergic function in a mammal |
US5037833A (en) * | 1988-07-25 | 1991-08-06 | Hoechst-Roussel Pharmaceuticals Inc. | N-[substituted alkylidene]fused-bicycloalkylidene quinolinamines useful for enhancing the cholinergic function in a mammal |
US5391553A (en) * | 1987-03-17 | 1995-02-21 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted 9-amino-tetrahydroacridines and related compounds |
US6248750B1 (en) | 1987-04-20 | 2001-06-19 | Hoechst Roussel Pharmaceuticals | 9-hydroxyamino tetrahydroacridine and related compounds |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE564863C (en) * | 1927-02-25 | 1932-11-23 | Gen Electric Co Ltd | Arrangement for generating tilting vibrations with glow tubes |
-
1965
- 1965-01-22 BE BE658695D patent/BE658695A/xx unknown
- 1965-01-27 ES ES0308636A patent/ES308636A1/en not_active Expired
- 1965-01-28 DE DEA48263A patent/DE1232148B/en active Pending
- 1965-02-01 CH CH132865A patent/CH435279A/en unknown
- 1965-02-03 GB GB4754/65A patent/GB1022940A/en not_active Expired
- 1965-04-14 FR FR13268A patent/FR4483M/fr not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4108998A (en) | 1976-11-08 | 1978-08-22 | American Home Products Corp. | Furo[3,4-b]quinoline derivatives and pharmaceutical compositions and methods employing them |
US4897400A (en) * | 1987-02-13 | 1990-01-30 | Hoeschst-Roussel Pharmaceuticals, Inc. | 9-amino-1,4-ethano-1,2,3,4-tetrahydroacridine and related compounds useful for incresing the cholinergic function in a mammal |
US5401749A (en) * | 1987-02-13 | 1995-03-28 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,4ethano-1,2,3,4-tetrahydroacridine and related compounds |
US5391553A (en) * | 1987-03-17 | 1995-02-21 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted 9-amino-tetrahydroacridines and related compounds |
US6248750B1 (en) | 1987-04-20 | 2001-06-19 | Hoechst Roussel Pharmaceuticals | 9-hydroxyamino tetrahydroacridine and related compounds |
US5013741A (en) * | 1987-09-08 | 1991-05-07 | Hoechst-Roussel Pharmaceuticals Incorporated | N-[substituted alkylidene]-1,2,3,4-tetrahydro-9-acridinamines useful for enhancing the cholinergic function in a mammal |
US4800203A (en) * | 1987-09-24 | 1989-01-24 | Hoechst-Roussel Pharmaceuticals, Inc. | Pyrrolo(1,2-b)cinnolines |
US5037833A (en) * | 1988-07-25 | 1991-08-06 | Hoechst-Roussel Pharmaceuticals Inc. | N-[substituted alkylidene]fused-bicycloalkylidene quinolinamines useful for enhancing the cholinergic function in a mammal |
US4916135A (en) * | 1989-05-08 | 1990-04-10 | Hoechst Roussel Pharmaceuticals Inc. | N-heteroaryl-4-quinolinamines |
Also Published As
Publication number | Publication date |
---|---|
FR4483M (en) | 1966-10-03 |
BE658695A (en) | 1965-07-22 |
CH435279A (en) | 1967-05-15 |
ES308636A1 (en) | 1965-05-16 |
DE1232148B (en) | 1967-01-12 |
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