GB851780A - New indole derivatives - Google Patents
New indole derivativesInfo
- Publication number
- GB851780A GB851780A GB5100/59A GB510059A GB851780A GB 851780 A GB851780 A GB 851780A GB 5100/59 A GB5100/59 A GB 5100/59A GB 510059 A GB510059 A GB 510059A GB 851780 A GB851780 A GB 851780A
- Authority
- GB
- United Kingdom
- Prior art keywords
- products
- diastereoisomers
- alkyl group
- alcohol
- indolyl
- 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
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000002934 diuretic Substances 0.000 abstract 2
- 229940030606 diuretics Drugs 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 238000002844 melting Methods 0.000 abstract 2
- 230000008018 melting Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- ZDLSWUIHNOOYCF-UHFFFAOYSA-N 2-(pyridin-3-ylmethyl)-1h-indole Chemical compound C=1C2=CC=CC=C2NC=1CC1=CC=CN=C1 ZDLSWUIHNOOYCF-UHFFFAOYSA-N 0.000 abstract 1
- KLTNBISVXAYPGG-UHFFFAOYSA-N 2-[2-(methoxymethyl)pyridin-3-yl]-1H-indole Chemical compound N1C(=CC2=CC=CC=C12)C=1C(=NC=CC1)COC KLTNBISVXAYPGG-UHFFFAOYSA-N 0.000 abstract 1
- NQAIQKCDQAOHIA-UHFFFAOYSA-N 3-(piperidin-2-ylmethyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CC1CCCCN1 NQAIQKCDQAOHIA-UHFFFAOYSA-N 0.000 abstract 1
- FDYZWMQKFRZTEX-UHFFFAOYSA-N [3-(1H-indol-2-yl)piperidin-2-yl]methanol Chemical compound N1C(=CC2=CC=CC=C12)C1C(NCCC1)CO FDYZWMQKFRZTEX-UHFFFAOYSA-N 0.000 abstract 1
- LQICLTIEKJHHJW-UHFFFAOYSA-N [3-(1H-indol-2-yl)pyridin-2-yl]methanol Chemical compound N1C(=CC2=CC=CC=C12)C=1C(=NC=CC1)CO LQICLTIEKJHHJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- -1 elixirs Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0851780/IV(b)/1> where R represents an alkyl group having 1 to 5 carbon atoms, in the form of diastereoisomers or mixtures of diastereoisomers, and acidaddition salts thereof; the preparation thereof by etherifying the corresponding free hydroxy compound with an alcohol ROH, the reaction being carried out if desired at about 50 DEG C. to yield one diastereoisomer or below 5 DEG C. to yield the other, or by hydrogenating a compound of the formula: <FORM:0851780/IV(b)/2> where B represents a <FORM:0851780/IV(b)/3> , <FORM:0851780/IV(b)/4> , or <FORM:0851780/IV(b)/5> group in aqueous alcoholic medium where the alcohol is ROH, and, if desired converting the products of any of the above processes into their acid-addition salts; and pharmaceutical compositions containing the products. Lower melting point diastereoisomers may be converted into their higher melting point forms by treatment with a solution of hydrogen chloride in an alcohol ROH at between 20 DEG . and 50 DEG C., the alcohol being one in which the alkyl group R is the same as the alkyl group R of the ether being treated. The products are diuretics. 3-Indolyl 2-piperidyl methanol and 3-(2-piper-idylmethyl)-indole are obtained as by-products in the catalytic hydrogenation of 3-picolylindole. 3-Indolyl 2-pyridyl methoxymethane is prepared by the action of methanolic hydrogen chloride on 3-indolyl 2-pyridyl methanol.ALSO:Pharmaceutical compositions comprise compounds of the general formula: <FORM:0851780/VI/1> where R represents an alkyl group having 1 to 5 carbon atoms, in the form of diastereoisomers or mixtures thereof; or acid addition salts thereof; with suitable pharmaceutical diluents. Oral preparations may be in the form of emulsions, solutions, suspensions, syrups, elixirs, capsules, tablets, pills, dispersible powders and granules. The products are diuretics.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR851780X | 1958-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB851780A true GB851780A (en) | 1960-10-19 |
Family
ID=9325338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5100/59A Expired GB851780A (en) | 1958-02-25 | 1959-02-13 | New indole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB851780A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992006973A1 (en) * | 1990-10-15 | 1992-04-30 | Pfizer Inc. | Indole derivatives |
| US5545644A (en) * | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
| US5559246A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc. | Indole derivatives |
| US5559129A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc | Indole derivatives |
| US5578612A (en) * | 1990-10-15 | 1996-11-26 | Pfizer Inc. | Indole derivatives |
| US5607951A (en) * | 1990-10-15 | 1997-03-04 | Pfizer Inc | Indole derivatives |
| US5849739A (en) * | 1993-08-31 | 1998-12-15 | Pfizer Inc. | 5-arylindole derivatives |
| US5994352A (en) * | 1998-11-13 | 1999-11-30 | Pfizer Inc. | 5-arylindole derivatives |
| US6110940A (en) * | 1994-08-27 | 2000-08-29 | Pfizer Inc. | Salts of an anti-migraine indole derivative |
| CN106957254A (en) * | 2017-02-09 | 2017-07-18 | 郑州大学 | A kind of 3 alkoxyalkyl indole derivativeses and its preparation method and application |
-
1959
- 1959-02-13 GB GB5100/59A patent/GB851780A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5607951A (en) * | 1990-10-15 | 1997-03-04 | Pfizer Inc | Indole derivatives |
| US5545644A (en) * | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
| US5559246A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc. | Indole derivatives |
| US5559129A (en) * | 1990-10-15 | 1996-09-24 | Pfizer Inc | Indole derivatives |
| US5578612A (en) * | 1990-10-15 | 1996-11-26 | Pfizer Inc. | Indole derivatives |
| WO1992006973A1 (en) * | 1990-10-15 | 1992-04-30 | Pfizer Inc. | Indole derivatives |
| AU651637B2 (en) * | 1990-10-15 | 1994-07-28 | Pfizer Inc. | Indole derivatives |
| US6093822A (en) * | 1993-08-31 | 2000-07-25 | Pfizer Inc. | 5-arylindole derivatives |
| US5849739A (en) * | 1993-08-31 | 1998-12-15 | Pfizer Inc. | 5-arylindole derivatives |
| US6110940A (en) * | 1994-08-27 | 2000-08-29 | Pfizer Inc. | Salts of an anti-migraine indole derivative |
| US6380226B1 (en) | 1994-08-27 | 2002-04-30 | Pfizer Inc | Salts of an anti-migraine indole derivatives |
| US5994352A (en) * | 1998-11-13 | 1999-11-30 | Pfizer Inc. | 5-arylindole derivatives |
| CN106957254A (en) * | 2017-02-09 | 2017-07-18 | 郑州大学 | A kind of 3 alkoxyalkyl indole derivativeses and its preparation method and application |
| CN106957254B (en) * | 2017-02-09 | 2019-11-15 | 郑州大学 | A kind of 3-alkoxyalkylindole derivative and its preparation method and application |
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