GB1030623A - 3-substituted-indoles and their preparation - Google Patents
3-substituted-indoles and their preparationInfo
- Publication number
- GB1030623A GB1030623A GB48378/62A GB4837862A GB1030623A GB 1030623 A GB1030623 A GB 1030623A GB 48378/62 A GB48378/62 A GB 48378/62A GB 4837862 A GB4837862 A GB 4837862A GB 1030623 A GB1030623 A GB 1030623A
- Authority
- GB
- United Kingdom
- Prior art keywords
- indole
- formula
- alkyl
- pyrrolidinyl
- reducing
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Abstract
The invention comprises compounds of the Formulae I, V and XV, wherein R represents a C1-4 alkyl group, R1, R2, R3, and R4 represent hydrogen atoms or C1-4 alkyl groups and R5 represents a hydrogen atom or a benzyl or C1-4 alkyl group, and the preparation of compounds of the Formula XVI, wherein Z represents a 2-pyrrolidinyl group of the Formula XVII or a 2-piperidyl group of the Formula XVIII, by reacting an indole of the Formula XIX with the required 2-pyrrolidone or 2-piperidone, in the presence of phosphorus oxychloride at a temperature between about 50 DEG and 150 DEG C. and reducing the thus obtained products of the Formulae V and XV respectively, and, when R5 represents a hydrogen atom, if desired replacing it by an alkyl or benzyl group by reacting the product with an alkyl or benzyl halide in the presence of an alkaline condensing agent; and the preparation of compounds of the Formula VIII by reacting a compound of the Formula IX, wherein R7 and R8 represent hydrogen atoms or aryl, aralkyl or alkyl groups or when joined represent with the nitrogen atom a saturated heterocyclic amino radical, with a compound of the formula R1R2CHNO2 to produce a 3-(4-nitrobutyryl) indole of the Formula XI and reducing and concomitantly cyclizing said indole with hydrogen in the presence of Raney nickel and reducing the thus produced compound with an alkali metal complex hydride or by catalytic hydrogenation in the presence of a noble metal catalyst to produce a 3-(2-pyrrolidinyl)indole of the Formula XII and alkylating said compound, or by reducing and concomitantly cyclizing a compound of the Formula XIII, alkylating the pyrrolidinyl nitrogen atom of the resulting compound, making basic to obtain the 3-(1-alkyl-2-pyrrolidinylidene)-3H-indole and either reducing with an alkali metal complex hydride or alkylating or benzylating with an alkyl or benzyl halide to produce a 3 - (1 - alkyl - 2 - pyrrolidinylidene) - 3H - indole quaternary ammonium salt of the Formula XIV where R6 represents a benzyl or C1-4 alkyl and Y represents a halogen atom and reducing the quaternary salt with an alkali metal complex hydride. <FORM:1030623/C2/1> <FORM:1030623/C2/2> <FORM:1030623/C2/3> 3 - (1 - Formyl - 5 - methyl - 2 - pyrrolidinyl)indole is prepared by refluxing 3-(5-methyl-2-pyrrolidinyl)indole with methyl formate. 3 - (1 - Acetyl - 5,5 - dimethyl - 2 - pyrrolidinly)indole is prepared by treating 3-(5,5-dimethyl-2-pyrrolidinyl)indole with acetic anhydride.ALSO:Pharmaceutical compositions for the treatment of neuroses to psychotic conditions or oral and parenteral application comprise 3-(2-pyrrolidinyl) indoles (and 3-(2-piperidyl) indoles <FORM:1030623/A5-A6/1> <FORM:1030623/A5-A6/2> where R is an alkyl group of 1 to 4 carbon atoms, R1, R2, R3 and R4 are hydrogen atoms or alkyl groups of 1 to 4 carbon atoms and R5 is a hydrogen atom or a benzyl or alkyl group of 1 to 4 carbon atoms, or addition salts thereof, m associations with a pharmaceutical carrier. Examples of suitable dosage forms are tablets, capsules, pills, troches, powder packets, granules, wafers, sachets, syrups, elixirs, suspensions and, for veterinary application, a food premix. Other active agents which may be present include analgetic agents, e.g. codeine, aspirin, acetophenetidine, salicylamide and N-acetyl-p-aminophenol; hypnotic agents, e.g. barbiturates and chloral hydrate; steroids, e.g. hydrocortisone, prednisolone, fluprednisolone and methylprednisolone; muscle relaxants, e.g. chlorzoxazone, carisoprodol, mephenesin; meprobamate, phenaglycodal zoxazolamine, and antihistaminics, e.g. chloropheniramine maleate, prophenpyridamine maleate and pyrilamine. Parental fluids may contain local anasthetics.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US16692662A | 1962-01-17 | 1962-01-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1030623A true GB1030623A (en) | 1966-05-25 |
Family
ID=22605238
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB48378/62A Expired GB1030623A (en) | 1962-01-17 | 1962-12-21 | 3-substituted-indoles and their preparation |
Country Status (5)
Country | Link |
---|---|
BR (1) | BR6245725D0 (en) |
CH (1) | CH475240A (en) |
DK (2) | DK105066C (en) |
FR (1) | FR2966M (en) |
GB (1) | GB1030623A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0021924A2 (en) * | 1979-06-12 | 1981-01-07 | Roussel-Uclaf | Indole derivatives, process for their preparation, their use as medicines and pharmaceutical compositions containing them |
FR2486081A2 (en) * | 1979-06-12 | 1982-01-08 | Roussel Uclaf | 4-Piperidinyl 1H-indole minus isomer - prepd. by resolving racemic mixt. with D minus tartaric acid |
FR2510111A1 (en) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | NOVEL DERIVATIVES OF PIPERIDIN-3-YL INDOLE, THEIR SALTS, PROCESS FOR PREPARING THEM, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THEM |
-
1962
- 1962-12-21 GB GB48378/62A patent/GB1030623A/en not_active Expired
- 1962-12-28 BR BR145725/62A patent/BR6245725D0/en unknown
-
1963
- 1963-01-15 CH CH48563A patent/CH475240A/en not_active IP Right Cessation
- 1963-01-16 DK DK38564AA patent/DK105066C/en active
- 1963-01-16 DK DK20863AA patent/DK106331C/en active
- 1963-04-12 FR FR931450A patent/FR2966M/en active Active
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0021924A2 (en) * | 1979-06-12 | 1981-01-07 | Roussel-Uclaf | Indole derivatives, process for their preparation, their use as medicines and pharmaceutical compositions containing them |
EP0021924A3 (en) * | 1979-06-12 | 1981-02-18 | Roussel-Uclaf | Indole derivatives, process for their preparation, their use as medicines, pharmaceutical compositions containing them and intermediates |
FR2486081A2 (en) * | 1979-06-12 | 1982-01-08 | Roussel Uclaf | 4-Piperidinyl 1H-indole minus isomer - prepd. by resolving racemic mixt. with D minus tartaric acid |
FR2510111A1 (en) * | 1981-07-24 | 1983-01-28 | Roussel Uclaf | NOVEL DERIVATIVES OF PIPERIDIN-3-YL INDOLE, THEIR SALTS, PROCESS FOR PREPARING THEM, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THEM |
EP0071520A1 (en) * | 1981-07-24 | 1983-02-09 | Roussel-Uclaf | 3-Piperidinylindole derivatives, their salts and preparation, their use in medicines and pharmaceutical preparations containing them |
Also Published As
Publication number | Publication date |
---|---|
BR6245725D0 (en) | 1973-05-24 |
CH475240A (en) | 1969-07-15 |
FR2966M (en) | 1964-11-30 |
DK106331C (en) | 1967-01-23 |
DK105066C (en) | 1966-08-15 |
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