JPS574987A - Pyridoindolecarboxylic acid derivative and its preparation - Google Patents
Pyridoindolecarboxylic acid derivative and its preparationInfo
- Publication number
- JPS574987A JPS574987A JP7732080A JP7732080A JPS574987A JP S574987 A JPS574987 A JP S574987A JP 7732080 A JP7732080 A JP 7732080A JP 7732080 A JP7732080 A JP 7732080A JP S574987 A JPS574987 A JP S574987A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- formula
- compound shown
- pyridoindolecarboxylic
- thionyl
- 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.)
- Pending
Links
- KEVVIZLJCBTAQB-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline-2-carboxylic acid Chemical class N1=CC=CC2=C(NC(C(=O)O)=C3)C3=CC=C21 KEVVIZLJCBTAQB-UHFFFAOYSA-N 0.000 title abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KOVRZNUMIKACTB-UHFFFAOYSA-N 9H-pyrido[3,4-b]indole-3-carboxylic acid ethyl ester Chemical compound N1C2=CC=CC=C2C2=C1C=NC(C(=O)OCC)=C2 KOVRZNUMIKACTB-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 etc.) Chemical compound 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 230000000506 psychotropic effect Effects 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
NEW MATERIAL:A pyridoindolecarboxylic acid derivative shown by the formula I (X is H, lower alkyl, lower alkoxy, OH, or halogen; R is alkyl) and its acid addition salt.
EXAMPLE: β-Carboline-3-carboxylic acid ethyl ester.
USE: A drug having psychotropic actions.
PROCESS: A compound shown by the formula II and an alcohol shown by the formula R-OH are subjected to contact reaction in the presence of a hydrogen halide (e.g., hydrogen chloride, hydrogen bromide, etc.), sulfuric acid or thionyl halide (e.g., thionyl chloride, thionyl bromide etc.), to give a compound shown by the formula I. Pharmaceutically acceptable acid addition salts of the compound shown by the formula I, for example, include acid addition salts of inorganic acids, e.g., hydrochloric acid, sulfuric acid, etc. or those of organic acids, e.g., maleic acid, tartaric acid, etc.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7732080A JPS574987A (en) | 1980-06-09 | 1980-06-09 | Pyridoindolecarboxylic acid derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7732080A JPS574987A (en) | 1980-06-09 | 1980-06-09 | Pyridoindolecarboxylic acid derivative and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS574987A true JPS574987A (en) | 1982-01-11 |
Family
ID=13630635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7732080A Pending JPS574987A (en) | 1980-06-09 | 1980-06-09 | Pyridoindolecarboxylic acid derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS574987A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57123180A (en) * | 1980-12-17 | 1982-07-31 | Schering Ag | 3-substituted beta-carboline, manufacture and psychotropic drug containing same |
| JPS6041676A (en) * | 1983-05-27 | 1985-03-05 | シエ−リング・アクチエンゲゼルシヤフト | Beta-carboline-3-carboxylic acid derivative, manufacture andpsychotic agent |
| JPS60100577A (en) * | 1983-09-27 | 1985-06-04 | シエ−リング・アクチエンゲゼルシヤフト | Substituted beta-carboline derivative, manufacture and psychotropic drug |
| JPS6140284A (en) * | 1984-05-15 | 1986-02-26 | シエ−リング・アクチエンゲゼルシヤフト | Beta-carboline_3_carboxylic acid derivative, manufacture and psychotropic and pharmaceutical composition |
| EP0222693A2 (en) * | 1985-11-13 | 1987-05-20 | Schering Aktiengesellschaft | 3-Oxadiazolyl and 3-carboxylic-acid beta-carboline derivatives, their preparation and their use as medicaments |
-
1980
- 1980-06-09 JP JP7732080A patent/JPS574987A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57123180A (en) * | 1980-12-17 | 1982-07-31 | Schering Ag | 3-substituted beta-carboline, manufacture and psychotropic drug containing same |
| JPS6041676A (en) * | 1983-05-27 | 1985-03-05 | シエ−リング・アクチエンゲゼルシヤフト | Beta-carboline-3-carboxylic acid derivative, manufacture andpsychotic agent |
| JPS60100577A (en) * | 1983-09-27 | 1985-06-04 | シエ−リング・アクチエンゲゼルシヤフト | Substituted beta-carboline derivative, manufacture and psychotropic drug |
| JPH0586390B2 (en) * | 1983-09-27 | 1993-12-10 | Schering Ag | |
| JPS6140284A (en) * | 1984-05-15 | 1986-02-26 | シエ−リング・アクチエンゲゼルシヤフト | Beta-carboline_3_carboxylic acid derivative, manufacture and psychotropic and pharmaceutical composition |
| EP0222693A2 (en) * | 1985-11-13 | 1987-05-20 | Schering Aktiengesellschaft | 3-Oxadiazolyl and 3-carboxylic-acid beta-carboline derivatives, their preparation and their use as medicaments |
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