IE43972B1 - Piperidine derivatives of indole - Google Patents
Piperidine derivatives of indoleInfo
- Publication number
- IE43972B1 IE43972B1 IE2396/76A IE239676A IE43972B1 IE 43972 B1 IE43972 B1 IE 43972B1 IE 2396/76 A IE2396/76 A IE 2396/76A IE 239676 A IE239676 A IE 239676A IE 43972 B1 IE43972 B1 IE 43972B1
- Authority
- IE
- Ireland
- Prior art keywords
- indole
- ethyl
- piperidine
- process according
- general formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1510765 Piperidinoalkylindoles BOEHRINGER MANNHEIM GmbH 4 Nov 1976 [7 Nov 1975] 45918/76 Heading C2C The invention comprises compounds of formula and their pharmacologically compatible salts, wherein R 1 , R 2 and R 3 are each H or C 1-6 alkyl, or R 3 may be halogen or C 1-6 alkoxy, and X is C 2 or C 3 alkylene. In examples, these compounds are prepared by either reacting a 3-bromoalkyl- or toxyloxyalkylindole with a 4-phenoxymethylpiperidine or introducing R 1 = alkyl. Therapeutic compositions having antihypertensive activity comprise compounds of the above formula, and may be administered orally or parenterally.
Description
The present invention is concerned with new piperidine derivatives of indole and with the preparation thereof.
The new piperidine derivatives of indole according to the present invention are compounds of the general formula:-
wherein R^ and Rg, which may be the same or different, are hydrogen atoms or lower alkyl radicals, R- is a hydrogen or halogen atom or a lower alkyl or alkoxy radical and X is a straight-chain or branched alkylene radical containing 2 or 5 carbon atoms; and the salts thereof with pharmacologically compatible acids.
The lower alkyl radicals R^, Rg and R^ can be straight-chained or branched and contain up to 6 and preferably up to 4 carbon atoms. The lower alkoxy radicals R^ preferably contain up to 4 carbon atoms. The preferred halogen atoms R^ are fluorine, chlorine and. bromine atoms.
Examples of straight-chain and branched alkylene radicals containing 2 or 5 carbon atoms represented by X include ethylene, methylmethylene, trimethylene, dimethylmethylene and aethylethylene, ethylene and trimethylene being preferred.
The new-compounds of general formula (I) according to the-present invention, and the pharmacologically compatible salts thereof, have an anti-hypertensive action.
Ihe new compounds of general formula (I) according to the present invention can be prepared by reacting an indole
-243973 derivative of the general formula:-
R (II)
R, '2 wherein R^, R2 and X have the same meanings as above and Y is a reactive residue, with a piperidine derivative of the general 'formula:-
wherein R^ has the same meaning as above, or with an acid addition salt thereof, and, when R1 in general formula (II) represents a hydrogen atom, this is, if desired, replaced by a lower alkyl radical subsequent to the condensation, the reaction product obtained then, if desired, being converted into a pharmacologically compatible salt.
The reactive residue'Y in compounds of general formula (II) can be, for example, a chlorine or bromine atom or a mesyloxy or tosyloxy radical.
The reaction of the indole derivatives (II) with the piperidine derivatives (III) is preferably carried out in a solvent, for example, dioxan, isopropanol or ΪΓ,Ν-dimethyl formamide, in the presence of an organic or inorganic base, for example, M-ethyl-diisopropylamine, triethylamine or potassium carbonate, or in the presence of an excess of the piperidine derivative (III), at a temperature of from 20°0. to the reflux temperature.
•343972
The compounds of general formula (II) are either known or can he easily prepared from known compounds. The compounds of general formula (III) are described in Patent Specification Noa 43866.
The subsequent introduction of a lower alkyl radical as substituent R^ can be carried out by reaction of a compound of general formula (I), in which R^ is a hydrogen atom, with an appropriate reactive alkyl compound, for example an alkyl halide, according to known methods.
The pharmacologically compatible salts can be prepared in conventional manner, for example, by neutralisation of the compounds (I) with non-toxic inorganic or organic acids, for example hydrochloric acid, sulphurip ' acid, phosphoric aoid, hydrobromic acid, acetic acid,
L5 lactic acid, citric aoid, malic acid, salicylic acid, malonic acid., maleic acid or succinic acid.
The new compounds (I) according to the present invention and the salts thereof can be administered enterally and parenterally in liquid or solid, form. Thus, !O the present invention also provides pharmaceutical compos-.
itions comprising at least one of the new compounds, in admixture with a solid or liquid pharmaceutical diluent or carrier. For this purpose, there can be used the conventional forms of administration, for example, tablets, capsules, dragees, syrups, solutions aid suspensions.
As injection meaiuEi,. it is preferred to use water which contains the additives usual in the case of injection solutions, for example, stabilising agents, solubilising agents and buffers. Additives of this type include, for
-443372 example, tartrate and citrate buffers, ethanol, complex formers (such as ethylenediamine-tetraacetic acid and the non-toxic salts thereof) and high molecular weight polymers (such as liquid polyethylene oxide) for viscosity regulation.
liquid carrier materials for injection solutions must be sterile and are preferably placed into ampoules. Solid carrier materials include, for example, starch, lactose·, mannitol, methyl cellulose, talc, highly dispersed silicic acids, high molecular weight fatty acids (sueh as stearic acid), gelatine, agar-agar, calcium phosphate, magnesium stearate, animal and vegetable fats and solid high molecular weight polymers (such as polyethylene glycols). Compositions suitable for oral administration can, if desired, contain flavouring and sweetening materials.
The following Examples are given for the purpose of illustrating the present invention:Example 1.
-/2-(4-Phenoxymethylpiperidino)-ethyl7-indole.
A mixture of 8.96 g. (0.04 mol) 5-(2-bromoethyl)20 indole, 7.65 g. (0.04 mol) 4-phenoxymethylpiperidine,
7.76 g. (0.06 mol) Ιϊ-ethyl-diisopropylamine and 100 ml. dioxan is heated under reflux for 9 hours. After cooling, the reaction mixture is filtered, the filtrate is evaporated in a vacuum and the residue is taken up in diethyl ether, washed with water, dried over anhydrous sodium sulphate and evaporated. After recrystallisation from isopropanol/ligroin, there are obtained 5·55 g. 5-/2-(4-phenoxymethyl)-piperidino)ethyl/-indole (41% of theory); m.p. 115 - 114°0.
By the addition of excess ethereal hydrogen chloride solution to the isopropanolic solution, there is obtained the hydrochloride; m.p. 215°C.
-543972
The following compounds are obtained in an analogous manner:
product and starting materials Yield % m.p. C. (solvent used for recryst- allisation) 3- ί2-/4-(2-bromophenoxymethyl)piperidino7-ethyl} -indole from 3-(2-bromoethyl)-indole and 4-(2bromophenoxymethyl)-piperidine 33 101 - 102 (isopropanol) 3- ί2-/4-(2-ohlorophenoxymethyl)piperidino/-ethyl)· -indole from 3-(2-bromoethyl)-indole and 4-(2ohlorophenoxymethyl)-piperidine 37 ' 113 - 114 (diethyl ether) 3- { 2-/4-(3-chlorophenoxymethyl)piperiaino/-ethylj -indole from 3-(2-bromoethyl)-indole and 4-(3chlorophenoxymethyl)-piperidine 51 133 - 135 (ethyl acetate) 3- { 2-/4-(4-chlorophenoxymethyl)piperiaino/-ethyl} -indole from 3-(2-bromoethyl)-indole and 4-(4chlorophenoxymethyl)-piperidine 32 141 - 142 (diethyl ether) 3- £2-/4-(2-fluorophenoxymethyl)piperidino7-ethyl}- -indole from 3-(2-bromoethyl)-indole and 4-(2fluor ophenoxymethyl)-piperidine 48- 120 - 121 (ethyl acetate) 3-ί 2-/4-(4-fluorophenoxymethyl)piperidino/-ethyl} -indole from 3-(2-bromoethyl)-indole and 4-(4fluorophenoxymethyl)-piperidine 36 130 - 131 (diethyl ether) 3- f2-/4-(2-methoxy-phenoxymethyl)piperidino/-ethyl} -indole from 3-(2-bromoethyl)-indole and 4-(2methoxy-phenoxymethyl) -piperidine 32 107 - 108 (isopropanol) 3- ί 2-/4-(3-methoxy-phen0xymethyl)piperidino/-ethyl} -indole from 3-(2-bromoethyl)-indole and 4-(3methoxy-phenoxymethyl)-piperidine 38 100 - 102 (ethyl acetate) 3- £ 2-/4-(4-methoxy-phenoxymethyl)piperidino7-ethyl} -indole from 3-(2-bromoethyl)-indole and 4-(4methoxy-phenoxymethyl)-piperidine 44 120 - 121 (ethyl acetate) 3- { 2-/4-(2-n-butoxy-phenoxymethyl)piperidino7-ethyl) -indole from 3-(2-bromoethyl)-indole and 4-(2-nbutoxy-phenoxymethyl)-piperidine ~ 35 90 - 91 (ethyl acetate)
-643972
product and starting materials Yield # m.p. °C. (solvent used for recrystallisation) 5- ί 2-/4-(2-methyl-phenoxymethyl)piperidino7-ethyl} -indole from 5-(2-bromoethyl)-indole and 4-(2methyl-phenoxymethyl)-piperidine 41 102 - 105 (isopropanol) 5- £ 2-/4-(3-methyl-phenoxymethyl)piperidinoZ-etliyl} -indole from 5-(2-bromoethyl)-indole and 4-(3methyl-phenoxymethyl)-piperidine 32 98 - 100 (diethyl ether) 5- ί 2-/4-(4-methyl-phenoxymethyl)piperidino7-ethyl} -indole from 5-(2-bromoethyl)-indole and 4-(4methyl-phenoxymethyl)-piperidine 58 150 - 152 (ethyl acetate) 1-methyl-5-/2-(4-nhenoxymethylpiperidino)-ethyl7-indole from 1-methyl-5-(2-bromoethyl)-indole and 4-phenoxymethyl-piperidine 45 89 - 90 (isopropanol) 2-methyl-5-/2-(4-phenoxymethylpiperidino)-ethyl7-indole from 2-methyl-5-(2-bromo ethyl)-indole and 4-phenoxymethyl-piperidine 45 hydrochloride 214 - 216 (isopropanol) 5-/3-(4-phenoxymethyl-piperidino)propyl7-indole from 5-(3-tosyloxypropyl)-indole and 4-phenoxymethylpiperidine 45 hydrochloride 222 - 224 (methanol)
Example 2.
1-Methyl-5-/2-(4-phenoxymethylpiueridino)-ethyl7-lndole.
To a solution of 0.1 g. ferric nitrate and 1.25 g.
sodium in 250 ml. liquid ammonia are added 9.0 g. (0.027 mol)
-/2-(4-phenoxymethylpiperidino)-ethyl7-indole. After stirring for 1 hour, there is added dropwise a solution of
3.9 g. (Ο.Ο58 mol) methyl iodide in 50 ml. diethyl ether, followed by stirring for 5 hours at reflux temperature.
After the addition of 5.3 g. ammonium chloride, the ammonia is left to evaporate off overnight. The residue is extracted with diethyl ether and purified by chromatography on silica •7439^ 2 gel, using chloroform/methanol (9:1 v/v). The first eluate is evaporated and the residue is recrystallised from isopropanol to give 4.9 g. 1-methyl-3-/2-(4-phenoxymethyl-piperidino)-ethyl7-indole (52% of theory); m.p.
89 - 90°C.
Example 5.
Preparation of pharmaceutical compositions.
Composition:
g. active material according to the present 0 , invention
150 g. lactose
100 g. polyvinylpyrrolidone solution (5% in water)
g. magnesium stearate ' g· sodium amylopeotin glycolate ,The active material is carefully mixed with the lactose in a kneader, thoroughly moistened with the polyvinylpyrrolidone solution and the resultant mass passed through a sieve with a mesh size of 1.9 mm. The resultant granulate is dried and freed from coarse components by passing through a sieve with a mesh size of 1.2 mm. and freed from fines by passing through a sieve with a mesh size of 0.6 mm.
The granules thus obtained can be filled directly into hard gelatine capsules (180 mg./capsule) and admini’ stered in this form.
The granules can also be mixed with the magnesium stearate and sodium amylopeotin glycolate and pressed into tablets. The diameter of the tablets is 8 mm., the weight is 200 mg., the hardness is 2.0 kg. and the content of * active material is 25 mg./tablet.
Claims (25)
1. CLAIMS :1. Piperidine derivatives of indole of the general formula :- wherein R^ and Rg, which may he the same or different, are l hydrogen atoms or lower alkyl radicals, R- is a hydrogen or halogen atom or a lower alkyl or alkoxy i’adical and X is a straight-chained or branched alkylene radical contain· ing 2 or ρ carbon atoms; and the pharmacologically compatible salts thereof.
2.
3. -/2-(4-Phenoxymethylpiperidino)-ethyl/-indole. 5. 3-f 2-/4-(2-Bromophenoxymethyl)-piperidino7-ethyl} indole.
4. 3- f 2-/4-(2-0hlorophenoxymethyl)-piperidino7-ethyl} · indole.
5. 3- {· 2-/4-(3-Chlorophenoxymethyl)-piperidino7-ethyl} indole.
6. 3- { 2-/4-(4-0hlorophenoxymethyl)-piperidino7-ethyl} · indole.
7. 5- f2-/4~(2-Fluorophenoxymethyl)-piperidino7-ethyl} indole.
8. 3- { 2-/4-(4-Fluorophenoxymethyl)-piperidino7-ethyl} indole.
9. 5- f2-/4-(2-Methoxyphenoxymethyl)-piperidino7-ethyl } indole.
10. 5- { 2-/4-(3-Methoxyphenoxymethyl)-piperidino7-ethylJ indole. -943972
11. 3-f 2-/4-(4-Hethoxyphenoxymethyl)-piperidino7-ethyl} indole.
12. 3- ί2-/4-(2-n-Sutoxyphenoxymethyl)-piperidino7ethyl} -indole. 5
13. · 3- ί2-/4-(2-Hethylphenoxymethyl)-piperidino7-ethyl } indole.
14. 3- (2-/4-(3-Kethylphenoxymethyl)-piperidino7-ethyl} indole.
15. 3- { 2-/4-(4-Methylphenoxymethyl)-piperidino7-ethyl} 10 indole.
16. 1-I-lethyl-3-/2-(4-phenoxymethylpiperidino)-ethyl7indole. i 7. 2-Hethyl-3-/2-(4-phenoxymethylpiperidino)-ethyl7indole. 15 18, 3-/3-(4-Rhenoxymethylpiperidino)-propyl7-indole.
17. 19. Process for the preparation of piperidine derivatives of indole of the general formula given in claim 1, wherein an indole derivative of the general formula:-
18. 20 in which R^, Rg have the same meanings as in claim 1 and Y is a reactive residue, is reacted with a piperidine derivative of the general formula:- in which R^ has the same meaning as in claim 1, or with an 25 acid addition salt thereof. -1043873 20. Process according to claim 19» wherein, when a product is obtained in which is a hydrogen atom, said product is subsequently alkylated,
19. 21. Process according to claim 19 or 20, wherein the 5 reaction is carried out in a solvent.
20. 22. Process according to any of claims 19 tc 21, wherein the reaction is carried out in the presence of an organic or inorganic base or of an excess of the piperidine derivative. 10
21. 23. Process according to any of claims 19 to 22, wherein the reaction is carried out at a temperature of from 20°C. to reflux temperature.
22. 24. Process according to any of claims 19 to 23, wherein the product obtained is converted into a salt by neutralis15 ation with a non-toxic inorganic or organic acid.
23. 25. Process for the preparation of piperidine derivatives of indole according to claim 1, substantially as hereinbefore described and exemplified.
24. 26. Piperidine derivatives of indole according to claim 1, 20 whenever prepared by the process according to any of claims 19 to 25.
25. 27. Pharmaceutical compositions, comprising at least one piperidine derivative of indole according to claim 1, in admixture with a solid or liquid pharmaceutical diluent or 25 carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752550001 DE2550001A1 (en) | 1975-11-07 | 1975-11-07 | NEW INDOL DERIVATIVES AND PROCESS FOR THEIR PRODUCTION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43972L IE43972L (en) | 1977-05-07 |
| IE43972B1 true IE43972B1 (en) | 1981-07-15 |
Family
ID=5961169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2396/76A IE43972B1 (en) | 1975-11-07 | 1976-10-29 | Piperidine derivatives of indole |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5259164A (en) |
| AT (1) | AT352727B (en) |
| BE (1) | BE847975A (en) |
| CA (1) | CA1077941A (en) |
| DE (1) | DE2550001A1 (en) |
| DK (1) | DK141529C (en) |
| FI (1) | FI763150A (en) |
| FR (1) | FR2330396A1 (en) |
| GB (1) | GB1510765A (en) |
| IE (1) | IE43972B1 (en) |
| LU (1) | LU76143A1 (en) |
| NL (1) | NL7612288A (en) |
| SE (1) | SE7612236L (en) |
| SU (1) | SU628816A3 (en) |
| ZA (1) | ZA766379B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2905876A1 (en) | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | NEW PIPERIDINOPROPYL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| US4327103A (en) * | 1980-07-07 | 1982-04-27 | Hoechst-Roussel Pharmaceuticals Incorporated | 3-{3-[4-(4-Fluorobenzoyl)piperidyl]propyl}-2-methyl indole |
-
1975
- 1975-11-07 DE DE19752550001 patent/DE2550001A1/en not_active Withdrawn
-
1976
- 1976-10-25 ZA ZA766379A patent/ZA766379B/en unknown
- 1976-10-28 CA CA264,610A patent/CA1077941A/en not_active Expired
- 1976-10-29 IE IE2396/76A patent/IE43972B1/en unknown
- 1976-11-02 DK DK495076A patent/DK141529C/en active
- 1976-11-02 SU SU762415646A patent/SU628816A3/en active
- 1976-11-03 FI FI763150A patent/FI763150A/fi not_active Application Discontinuation
- 1976-11-03 SE SE7612236A patent/SE7612236L/en not_active Application Discontinuation
- 1976-11-04 GB GB45918/76A patent/GB1510765A/en not_active Expired
- 1976-11-04 BE BE172070A patent/BE847975A/en unknown
- 1976-11-05 JP JP51133141A patent/JPS5259164A/en active Pending
- 1976-11-05 LU LU76143A patent/LU76143A1/xx unknown
- 1976-11-05 NL NL7612288A patent/NL7612288A/en not_active Application Discontinuation
- 1976-11-05 FR FR7633391A patent/FR2330396A1/en active Granted
- 1976-11-05 AT AT823976A patent/AT352727B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5259164A (en) | 1977-05-16 |
| AT352727B (en) | 1979-10-10 |
| DK141529B (en) | 1980-04-14 |
| DE2550001A1 (en) | 1977-05-12 |
| CA1077941A (en) | 1980-05-20 |
| LU76143A1 (en) | 1977-05-18 |
| ZA766379B (en) | 1977-10-26 |
| NL7612288A (en) | 1977-05-10 |
| BE847975A (en) | 1977-05-04 |
| FI763150A (en) | 1977-05-08 |
| FR2330396A1 (en) | 1977-06-03 |
| ATA823976A (en) | 1979-03-15 |
| DK141529C (en) | 1980-09-01 |
| IE43972L (en) | 1977-05-07 |
| DK495076A (en) | 1977-05-08 |
| GB1510765A (en) | 1978-05-17 |
| SE7612236L (en) | 1977-05-08 |
| FR2330396B1 (en) | 1979-06-29 |
| SU628816A3 (en) | 1978-10-15 |
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