GB869775A - 3-indolyl ketones - Google Patents
3-indolyl ketonesInfo
- Publication number
- GB869775A GB869775A GB31457/59A GB3145759A GB869775A GB 869775 A GB869775 A GB 869775A GB 31457/59 A GB31457/59 A GB 31457/59A GB 3145759 A GB3145759 A GB 3145759A GB 869775 A GB869775 A GB 869775A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- aralkyl
- ketones
- groups
- aralkoxy
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0869775/IV (b)/1> wherein A and B represent hydrogen or C1-8 branched-chain alkyl group, and the preparation of 3-indoyl ketones by reacting an indole unsubstituted in the 3-position with phosphorus oxychloride and a carboxylic acid amide of a hydrocarbon carboxylic acid optionally substituted by one or more inert substituents such as halo, cyano, nitro, tertiary amino, alkoxy, aryloxy, aralkoxy, alkylmercapto, aralkylmercapto or arylmercapto and a C1-8 alkylamine. The indoles may be substituted in the 1-position by C1-8 alkyl or C7-13 aralkyl groups, in the 2 position by C1-8 alkyl, C7-13 aralkyl, C6-12 aryl or haloaryl groups and in the 4,5,6 and -7 positions by C1-8 alkyl or alkoxy, C7-13 aralkyl or aralkoxy, C6-12 aryl or aryloxy, hydroxy groups, or halogen atoms. Indolyl ketones containing free hydroxy groups in the 4,5,6 or 7 positions are prepared from the corresponding benzyloxy compound, e.g. by catalytic hydrogenation. Specification 744,774 and German Specification 614,326 are referred to.ALSO:Pharmaceutical compositions comprise compounds of the general formula <FORM:0869775/VI/1> wherein A and B are hydrogen atoms or C1-5 alkyl radicals and R5 is a branched-chain C4-8 alkyl group and a solid or liquid pharmaceutical carrier. The compositions may be in the form of tablets, powder packets or capsules or dissolved or suspended in a solvent, for oral or parenteral administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US869775XA | 1958-09-24 | 1958-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB869775A true GB869775A (en) | 1961-06-07 |
Family
ID=22202086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31457/59A Expired GB869775A (en) | 1958-09-24 | 1959-09-15 | 3-indolyl ketones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB869775A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226399A (en) * | 1964-08-07 | 1965-12-28 | American Cyanamid Co | Substituted 3-formylindoles |
| US3259622A (en) * | 1962-09-07 | 1966-07-05 | Merck & Co Inc | 1-benzyl-3-indolyl-alpha-haloalkyl and alkylidenyl acetic acids |
| US3352856A (en) * | 1965-12-20 | 1967-11-14 | Upjohn Co | 2-(p-alkoxyphenyl)-3-substituted indoles |
| EP0022634A1 (en) * | 1979-06-28 | 1981-01-21 | Teijin Limited | Acylated indole derivatives, processes for their preparation and pharmaceutical compositions and drugs comprising them |
| AU574383B2 (en) * | 1983-09-28 | 1988-07-07 | Nippon Zoki Pharmaceutical Co., Ltd. | Acylindole derivatives |
| WO2001032621A1 (en) * | 1999-10-29 | 2001-05-10 | Wakunaga Pharmaceutical Co., Ltd. | Novel indole derivatives and drugs containing the same as the active ingredient |
| US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
-
1959
- 1959-09-15 GB GB31457/59A patent/GB869775A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259622A (en) * | 1962-09-07 | 1966-07-05 | Merck & Co Inc | 1-benzyl-3-indolyl-alpha-haloalkyl and alkylidenyl acetic acids |
| US3226399A (en) * | 1964-08-07 | 1965-12-28 | American Cyanamid Co | Substituted 3-formylindoles |
| US3352856A (en) * | 1965-12-20 | 1967-11-14 | Upjohn Co | 2-(p-alkoxyphenyl)-3-substituted indoles |
| EP0022634A1 (en) * | 1979-06-28 | 1981-01-21 | Teijin Limited | Acylated indole derivatives, processes for their preparation and pharmaceutical compositions and drugs comprising them |
| AU574383B2 (en) * | 1983-09-28 | 1988-07-07 | Nippon Zoki Pharmaceutical Co., Ltd. | Acylindole derivatives |
| WO2001032621A1 (en) * | 1999-10-29 | 2001-05-10 | Wakunaga Pharmaceutical Co., Ltd. | Novel indole derivatives and drugs containing the same as the active ingredient |
| US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
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