GB774858A - Tropane and -Î-tropane derivatives and process for preparation thereof - Google Patents
Tropane and -Î-tropane derivatives and process for preparation thereofInfo
- Publication number
- GB774858A GB774858A GB29364/55A GB2936455A GB774858A GB 774858 A GB774858 A GB 774858A GB 29364/55 A GB29364/55 A GB 29364/55A GB 2936455 A GB2936455 A GB 2936455A GB 774858 A GB774858 A GB 774858A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzene
- tropane
- triethylamine
- diphenylmalonyl
- reacted
- 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
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises acid amide derivatives of the tropane and q -tropane series, of the general formula: <FORM:0774858/IV(b)/1> (wherein R1 represents hydrogen or an alkoxy group, and wherein n is 1 and R2 represents a nicotinoyl, salicyloyl, benzoyl, p-nitrobenzoyl, benziloyl, Alkyl-O-CO-or (Alkyl)2N-CO-group, or n is 2 and R2 represents a malonyl, diphenylmalonyl or -CO- group, and the preparation thereof by reducing tropinone oxime or a 6-alkoxy derivative thereof (e.g. by catalytic hydrogenation or by means of sodium and an aliphatic alcohol) and reacting the resulting 3-amino-tropane or -q -tropane with the chloride or azide of a mono- or di-carboxylic acid R2(OH)n. Reference is also made to compounds containing a diphenylmalonyl group substituted in either or both of the phenyl groups by chlorine or bromine. The products are useful as pharmacodynamic agents for regulating the heart rhythm, or as intermediates in the manufacture of medicaments. In examples: (1)-(5) and (19) tropinone oxime is reduced with hydrogen at room temperature and 60 atmospheres pressure in the presence of Raney nickel in alcohol and acetic acid, and the resulting crude 3-aminotropane (containing 20-30 per cent of 3-amino-q -tropane) is reacted with (1) an ethereal solution of benzilic acid azide (prepared by adding an aqueous solution of sodium nitrite to a solution of benzilic acid hydrazide in dilute hydrochloric acid); (2) nicotinic acid azide (analogously prepared) in ether and ethyl acetate; (3) salicylic acid azide (analogously prepared) in ethyl acetate; (4) ethyl chlorocarbonate in benzene in the presence of triethylamine; (5) phosgene in benzene; and (19) diphenylmalonyl dichloride in chloroform in the presence of triethylamine; (6)-(12) and (20) 3-amino-q -tropane is reacted with (6) nicotinic acid chloride in benzene; (7a) salicylic acid chloride in benzene; (7b) salicylic acid azide in ethyl acetate; (8) benzilic acid azide in ether; (9) malonyl dichloride in benzene; (10) ethyl chlorocarbonate in benzene in the presence of triethylamine; (11) phosgene in benzene; (12) dimethylcarbamyl chloride in benzene in the presence of triethylamine; and (20) diphenylmalonyl dichloride similarly; (13)-(16) 6-ethoxytropinone is reacted with hydroxylamine hydrochloride in the presence of caustic potash, the oxime is reduced with sodium and amyl alcohol, and the resulting 6-ethoxy - 3 - amino - q - tropane is reacted with (13) nicotinic acid chloride in benzene; (14) salicylic acid azide in ethyl acetate; (15) benzilic acid azide in ethyl acetate; and (16) ethyl chlorocarbonate in benzene in the presence of triethylamine; (17) and (22) 6-methoxy-3-amino-q -tropane (prepared analogously to the ethoxy compound and characterized by reaction with phenyl isothiocyanate to form N-(6-methoxy - q - tropyl - 3) - N1 - phenylthiourea) is reacted with (17) malonyl dichloride in chloroform in the presence of triethylamine; and (22) diphenylmalonyl dichloride similarly; (18), (21) and (23) 6-methoxytropinone oxime hydrochloride is reduced with hydrogen at room temperature and 50 atmospheres pressure in the presence of Raney nickel in methanol, and the resulting 6-methoxy-3-aminotropane is reacted with (18) benzoyl chloride in chloroform in the presence of triethylamine; (21) diphenylmalonyl dichloride similarly; and (23) p-nitrobenzoyl chloride similarly. The hydrochlorides of the products of (1)-(16) are described.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH774858X | 1954-10-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB774858A true GB774858A (en) | 1957-05-15 |
Family
ID=4535725
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29364/55A Expired GB774858A (en) | 1954-10-20 | 1955-10-14 | Tropane and -Î-tropane derivatives and process for preparation thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB774858A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0013138A1 (en) * | 1978-12-30 | 1980-07-09 | Beecham Group Plc | Azabicycloalkyl derivatives, a process for their preparation and pharmaceutical compositions containing them |
US4321378A (en) * | 1979-01-16 | 1982-03-23 | Delalande S.A. | 8-(5-Pyrimidinecarboxamide)nor-tropane derivatives |
US4424358A (en) | 1979-01-16 | 1984-01-03 | Delalande S.A. | β-3-Amino nor-tropane compounds |
US4434170A (en) | 1980-11-07 | 1984-02-28 | Delalande S.A. | Nor-tropane derivatives, and their application in therapeutics |
US4471120A (en) * | 1979-01-16 | 1984-09-11 | Delalande S.A. | Nor-tropane derivatives |
US4797406A (en) * | 1983-08-26 | 1989-01-10 | Sandoz Ltd. | Amides and esters containing bridged piperidines and use as serotonin M antagonists |
US4803199A (en) * | 1982-06-29 | 1989-02-07 | Peter Donatsch | Pharmaceutically useful heterocyclic and carbocyclic acid esters and amides of alkylene bridged piperidines |
US5001133A (en) * | 1983-12-23 | 1991-03-19 | Sandoz Ltd. | Benzoic acid derivatives |
CN102993197A (en) * | 2012-12-27 | 2013-03-27 | 蕾硕医药化工(长沙)有限公司 | Tropinone derivative, and preparation method and application thereof |
-
1955
- 1955-10-14 GB GB29364/55A patent/GB774858A/en not_active Expired
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0013138A1 (en) * | 1978-12-30 | 1980-07-09 | Beecham Group Plc | Azabicycloalkyl derivatives, a process for their preparation and pharmaceutical compositions containing them |
EP0220339A1 (en) * | 1978-12-30 | 1987-05-06 | Beecham Group Plc | Azabicycloalkyl derivatives |
EP0081054A2 (en) * | 1978-12-30 | 1983-06-15 | Beecham Group Plc | Azabicyclo alkyl derivatives |
EP0081054A3 (en) * | 1978-12-30 | 1983-08-24 | Beecham Group Plc | Azabicyclo alkyl derivatives |
US4471120A (en) * | 1979-01-16 | 1984-09-11 | Delalande S.A. | Nor-tropane derivatives |
US4424358A (en) | 1979-01-16 | 1984-01-03 | Delalande S.A. | β-3-Amino nor-tropane compounds |
US4321378A (en) * | 1979-01-16 | 1982-03-23 | Delalande S.A. | 8-(5-Pyrimidinecarboxamide)nor-tropane derivatives |
US4434170A (en) | 1980-11-07 | 1984-02-28 | Delalande S.A. | Nor-tropane derivatives, and their application in therapeutics |
US4803199A (en) * | 1982-06-29 | 1989-02-07 | Peter Donatsch | Pharmaceutically useful heterocyclic and carbocyclic acid esters and amides of alkylene bridged piperidines |
US4910207A (en) * | 1982-06-29 | 1990-03-20 | Peter Donatsch | Method of treating psychosis with N-quinuclidinyl-benzamides |
US5017582A (en) * | 1982-06-29 | 1991-05-21 | Sandoz Ltd. | Method of inducing a serotonin M receptor antagonist effect with N-quinuclidinyl-benzamides |
US4797406A (en) * | 1983-08-26 | 1989-01-10 | Sandoz Ltd. | Amides and esters containing bridged piperidines and use as serotonin M antagonists |
US5001133A (en) * | 1983-12-23 | 1991-03-19 | Sandoz Ltd. | Benzoic acid derivatives |
CN102993197A (en) * | 2012-12-27 | 2013-03-27 | 蕾硕医药化工(长沙)有限公司 | Tropinone derivative, and preparation method and application thereof |
CN102993197B (en) * | 2012-12-27 | 2015-09-02 | 蕾硕医药化工(长沙)有限公司 | Tropinone derivative and its preparation method and application |
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