GB959203A - Indole derivatives and salts thereof - Google Patents
Indole derivatives and salts thereofInfo
- Publication number
- GB959203A GB959203A GB31373/60A GB3137360A GB959203A GB 959203 A GB959203 A GB 959203A GB 31373/60 A GB31373/60 A GB 31373/60A GB 3137360 A GB3137360 A GB 3137360A GB 959203 A GB959203 A GB 959203A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- alkoxy
- halogen
- substituted
- group
- 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
- 150000003839 salts Chemical class 0.000 title abstract 3
- 150000002475 indoles Chemical class 0.000 title abstract 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- -1 N-substituted aminomethyl Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000002184 metal Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0959203/C2/1> or its acid addition salts wherein R1 represents hydrogen, halogen, C1-5 alkyl or alkoxy, R2 and R3 which may be the same or different, represent hydrogen, halogen, C1-5 alkyl or alkoxy, acyl, benzyl, phenyl or phenyl groups substituted by halogen C1-5 alkyl or alkoxy or hydroxy groups and X is an N-substituted aminoalkyl group (where the alkyl group is straight or branched and contains 1-5 carbon atoms and where one or both substituents are either alkyl or cycloalkyl groups or they form together with the adjacent N-atom a saturated heterocyclic ring) and the preparation thereof by reacting an indole of the formula: <FORM:0959203/C2/2> wherein Z is a hydrogen or a metal atom, with a reactive ester of an alcohol XOH, optionally in the presence of a condensation agent or (wherein X is an N-substituted aminomethyl group) reacting an N-unsubstituted indole with formaldehyde and a secondary amine corresponding to the N-substituted aminomethyl group desired. Analgetic compositions containing salts of the compounds of the invention may take the form of tablets.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK326559AA DK96884C (en) | 1959-09-14 | 1959-09-14 | Process for the preparation of indole derivatives or their salts. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB959203A true GB959203A (en) | 1964-05-27 |
Family
ID=8120951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31373/60A Expired GB959203A (en) | 1959-09-14 | 1960-09-12 | Indole derivatives and salts thereof |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE595038A (en) |
| CH (1) | CH398595A (en) |
| DK (1) | DK96884C (en) |
| FR (1) | FR652M (en) |
| GB (1) | GB959203A (en) |
| NL (1) | NL113675C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3429886A (en) * | 1964-11-11 | 1969-02-25 | Ciba Geigy Corp | 1-tertiaryaminoalkyl-3-(4-pyridyl)-indoles |
| EP0025501A1 (en) * | 1979-08-02 | 1981-03-25 | Kali-Chemie Pharma GmbH | N-aminoalkyl indole derivatives and their salts, processes for their preparation and medicaments containing these compounds |
| EP1147107A4 (en) * | 1999-01-20 | 2002-05-22 | Merck & Co Inc | ANGIOGENESIS INHIBITORS |
| CN105218426A (en) * | 2014-06-17 | 2016-01-06 | 中国科学院兰州化学物理研究所 | A kind of method of Synthesis of Indole and isoquinilone derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3022648A1 (en) * | 1979-06-29 | 1981-01-15 | Sandoz Ag | NEW ORGANIC COMPOUNDS, THEIR PRODUCTION AND PHARMACEUTICAL PREPARATIONS THAT CONTAIN THESE COMPOUNDS |
-
1959
- 1959-09-14 DK DK326559AA patent/DK96884C/en active
-
1960
- 1960-09-12 GB GB31373/60A patent/GB959203A/en not_active Expired
- 1960-09-13 CH CH1034060A patent/CH398595A/en unknown
- 1960-09-13 FR FR838483A patent/FR652M/en not_active Expired
- 1960-09-14 NL NL255890A patent/NL113675C/en active
- 1960-09-14 BE BE595038A patent/BE595038A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3429886A (en) * | 1964-11-11 | 1969-02-25 | Ciba Geigy Corp | 1-tertiaryaminoalkyl-3-(4-pyridyl)-indoles |
| EP0025501A1 (en) * | 1979-08-02 | 1981-03-25 | Kali-Chemie Pharma GmbH | N-aminoalkyl indole derivatives and their salts, processes for their preparation and medicaments containing these compounds |
| US4374846A (en) | 1979-08-02 | 1983-02-22 | Kali-Chemie Pharma Gmbh | N-Amino alkyl indole compounds compositions containing same, and a method of using same in therapy of disorders of gastrointestinal motility |
| EP1147107A4 (en) * | 1999-01-20 | 2002-05-22 | Merck & Co Inc | ANGIOGENESIS INHIBITORS |
| CN105218426A (en) * | 2014-06-17 | 2016-01-06 | 中国科学院兰州化学物理研究所 | A kind of method of Synthesis of Indole and isoquinilone derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR652M (en) | 1961-06-19 |
| BE595038A (en) | 1961-01-02 |
| CH398595A (en) | 1966-03-15 |
| NL113675C (en) | 1967-05-16 |
| DK96884C (en) | 1963-09-16 |
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