GB975835A - Process for the preparation of new ª-carboline-carboxylic acid amide derivatives - Google Patents
Process for the preparation of new ª-carboline-carboxylic acid amide derivativesInfo
- Publication number
- GB975835A GB975835A GB1653/62A GB165362A GB975835A GB 975835 A GB975835 A GB 975835A GB 1653/62 A GB1653/62 A GB 1653/62A GB 165362 A GB165362 A GB 165362A GB 975835 A GB975835 A GB 975835A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- carboline
- hydrogen
- alkyl
- carboxylic acid
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0975835/C1/1> (wherein R is hydrogen, alkyl of at most 5 carbon atoms, trifluoromethyl, phenyl or benzyl; -NR1R2 is amino, hydrazino, mono- or dialkylamino with at most 3 carbon atoms per alkyl group, dialkylaminoalkylamino of at most 6 carbon atoms, hydroxyalkylamino of at most 3 carbon atoms, anilino, phenylalkylamino with at most 3 carbon atoms in the alkylene chain, pyridylamino, or pyridylalkylamino with at most 3 carbon atoms in the alkylene chain; R3 is hydrogen, alkyl of at most 5 carbon atoms or benzyl; R4 is hydrogen or alkyl of at most 5 carbon atoms; either R5 is hydrogen or alkyl of at most 5 carbon atoms and Z1, Z2 and Z3 are each hydrogen or R5 and Z3 as well as Z1 and Z2 is an additional bond, or R5 and Z3 is an additional bond and Z1 and Z2 each a hydrogen atom; and X is oxygen) and salts thereof with inorganic and organic acids; and their preparation by reaction of the amine NHR1R2 with the appropriate carboxylic acid or reactive derivative thereof, or by hydrolysis of the corresponding nitrile, or by reaction of a compound of the formula <FORM:0975835/C1/2> with the aldehyde RCHO; and, if the product is a 1, 2, 3, 4-tetrahydro-b -carboline and a fully unsaturated b -carboline is required, dehydrogenating the tetrahydro compound. Examples are given. 1, 2, 3, 4-Tetrahydro-b -carboline-3-carboxylic acid alkyl esters are prepared by condensing tryptophenes with aldehydes and esterifying the acids produced or by esterifying trypophanes with alcohols and condensing the trypophane alkyl esters with aldehydes. The products may be dehydrogenated to give b -carboline-3-carboxylic acid alkyl esters. The esters on saponification give the corresponding acids. 3-Cyano-b -carbolines are prepared by halogenating b -carbolines and reacting the 3-halogeno-b -carboline products with metal cyanides. 3-Cyano-1, 2, 3, 4-tetrahydro-b -carbolines are prepared by converting indole-3-acetaldehydro by Strecker synthesis into a -amino-b -(indole-3)-propionitriles and then cyclizing these with aldehydes. 1-Methyl-3, 4-dehydro-b -carboline-3-carboxylic acid methyl ester is prepared from the free acid and methanol, and isolated as the hydrochloride, or from N-acetyl-tryptophane-methyl ester which is heated with phosphorus trichloride and then with ethanol and hydrochloric acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8339061A | 1961-01-18 | 1961-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB975835A true GB975835A (en) | 1964-11-18 |
Family
ID=22177990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1653/62A Expired GB975835A (en) | 1961-01-18 | 1962-01-17 | Process for the preparation of new ª-carboline-carboxylic acid amide derivatives |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT239788B (en) |
| BE (4) | BE612728A (en) |
| ES (6) | ES273769A1 (en) |
| FR (3) | FR1837M (en) |
| GB (1) | GB975835A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030254A1 (en) * | 1979-08-29 | 1981-06-17 | Schering Aktiengesellschaft | Beta-carbolin-3-carboxylic acid derivatives, pharmaceutical compositions containing them and their therapeutical use |
| EP0031741A1 (en) * | 1979-12-07 | 1981-07-08 | SCIENCE UNION ET Cie SOCIETE FRANCAISE DE RECHERCHE MEDICALE | Substituted imino-acids, process for their preparation and their use as enzyme inhibitors |
| EP0054507A2 (en) * | 1980-12-17 | 1982-06-23 | Schering Aktiengesellschaft | 3-Substituted beta-carbolines, process for their production and compositions containing them |
| EP0347980A1 (en) * | 1988-06-20 | 1989-12-27 | Duphar International Research B.V | 8,9-Annelated beta-carbolines and 8,9-anelated-3,4-dihydro-beta-carbolines |
| EP0357122A2 (en) * | 1988-08-29 | 1990-03-07 | Duphar International Research B.V | Use of beta-carbolines, their bio-isosteric benzofuran and benzothiophene analogues for the manufacture of a medicament having cytostatic properties |
| WO1996011197A1 (en) * | 1994-10-10 | 1996-04-18 | Gerhard Bringmann | HALOGENATED β-CARBOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND USE OF THESE SUBSTANCES FOR INHIBITING THE RESPIRATORY CHAIN |
| US9440966B2 (en) | 2011-03-28 | 2016-09-13 | Sjt Molecular Research, S.L. | Compounds for treatment of metabolic syndrome |
| WO2017125952A1 (en) * | 2016-01-22 | 2017-07-27 | Council Of Scientific And Industrial Research | N-((1-phenyl-9h-pyrido[3,4-b]indol-3-yl)methyl)cinnamamides as anticancer agents and preparation thereof |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1084256A (en) * | 1963-11-06 | |||
| DE3247615A1 (en) * | 1982-12-23 | 1984-07-05 | Hoechst Ag, 6230 Frankfurt | SUBSTITUTED PHENYLSULFONYLOXYBENZIMIDAZOLE CARBAMINATES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MEDICINAL PRODUCT |
| GB2140797A (en) * | 1983-06-04 | 1984-12-05 | Tanabe Seiyaku Co | Tetrahydro-b-carboline derivatives |
| GB8330260D0 (en) * | 1983-11-12 | 1983-12-21 | Tanabe Seiyaku Co | Tetrahydro-beta-carboline derivatives |
| DE3535928A1 (en) * | 1985-10-04 | 1987-04-09 | Schering Ag | TETRAHYDRO (BETA) CARBOLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MEDICINAL PRODUCT |
| FR2724384B1 (en) * | 1994-09-14 | 1999-04-16 | Cemaf | NOVEL 3,4-DIHYDRO BETA-CARBOLINE DERIVATIVES OF MELATONIN AGONISTS, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MEDICAMENTS |
| US7115621B2 (en) * | 2001-04-25 | 2006-10-03 | Lilly Icos Llc | Chemical compounds |
| CN100503607C (en) * | 2003-06-02 | 2009-06-24 | 新疆华世丹药物研究有限责任公司 | Yageine derivative compounds and their uses |
-
1962
- 1962-01-16 ES ES0273769A patent/ES273769A1/en not_active Expired
- 1962-01-17 ES ES0273999A patent/ES273999A1/en not_active Expired
- 1962-01-17 ES ES0273997A patent/ES273997A1/en not_active Expired
- 1962-01-17 BE BE612728A patent/BE612728A/en unknown
- 1962-01-17 BE BE612725A patent/BE612725A/en unknown
- 1962-01-17 AT AT124063A patent/AT239788B/en active
- 1962-01-17 BE BE612726A patent/BE612726A/en unknown
- 1962-01-17 BE BE612727A patent/BE612727A/en unknown
- 1962-01-17 GB GB1653/62A patent/GB975835A/en not_active Expired
- 1962-01-17 ES ES0273783A patent/ES273783A1/en not_active Expired
- 1962-01-17 ES ES0273995A patent/ES273995A1/en not_active Expired
- 1962-01-17 ES ES0273996A patent/ES273996A1/en not_active Expired
- 1962-04-16 FR FR894620A patent/FR1837M/en active Active
- 1962-04-16 FR FR894619A patent/FR1836M/en active Active
- 1962-04-16 FR FR894618A patent/FR1825M/en active Active
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0030254A1 (en) * | 1979-08-29 | 1981-06-17 | Schering Aktiengesellschaft | Beta-carbolin-3-carboxylic acid derivatives, pharmaceutical compositions containing them and their therapeutical use |
| EP0031741A1 (en) * | 1979-12-07 | 1981-07-08 | SCIENCE UNION ET Cie SOCIETE FRANCAISE DE RECHERCHE MEDICALE | Substituted imino-acids, process for their preparation and their use as enzyme inhibitors |
| US4404206A (en) | 1979-12-07 | 1983-09-13 | Science Union Et Cie | Substituted iminoacid derivatives, process for preparing them and their use as enzyme inhibitors |
| EP0054507A2 (en) * | 1980-12-17 | 1982-06-23 | Schering Aktiengesellschaft | 3-Substituted beta-carbolines, process for their production and compositions containing them |
| EP0054507A3 (en) * | 1980-12-17 | 1982-09-15 | Schering Aktiengesellschaft Berlin Und Bergkamen | 3-substituted beta-carbolines, process for their production and compositions containing them |
| US5332746A (en) * | 1988-06-20 | 1994-07-26 | Duphar International Research B.V. | 8,9-annelated-β-carbolines and 8,9-annelated 3,4-dihydro-β-carbolines |
| EP0347980A1 (en) * | 1988-06-20 | 1989-12-27 | Duphar International Research B.V | 8,9-Annelated beta-carbolines and 8,9-anelated-3,4-dihydro-beta-carbolines |
| EP0357122A2 (en) * | 1988-08-29 | 1990-03-07 | Duphar International Research B.V | Use of beta-carbolines, their bio-isosteric benzofuran and benzothiophene analogues for the manufacture of a medicament having cytostatic properties |
| EP0357122A3 (en) * | 1988-08-29 | 1991-10-23 | Duphar International Research B.V | Use of beta-carbolines, their bio-isosteric benzofuran and benzothiophene analogues for the manufacture of a medicament having cytostatic properties |
| WO1996011197A1 (en) * | 1994-10-10 | 1996-04-18 | Gerhard Bringmann | HALOGENATED β-CARBOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND USE OF THESE SUBSTANCES FOR INHIBITING THE RESPIRATORY CHAIN |
| US9440966B2 (en) | 2011-03-28 | 2016-09-13 | Sjt Molecular Research, S.L. | Compounds for treatment of metabolic syndrome |
| WO2017125952A1 (en) * | 2016-01-22 | 2017-07-27 | Council Of Scientific And Industrial Research | N-((1-phenyl-9h-pyrido[3,4-b]indol-3-yl)methyl)cinnamamides as anticancer agents and preparation thereof |
| US10392385B2 (en) | 2016-01-22 | 2019-08-27 | Council Of Scientific & Industrial Research | N-((1-phenyl-9H-pyrido[3,4-b]indol-3-yl)methyl)cinnamamides as potential anticancer agents and preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AT239788B (en) | 1965-04-26 |
| ES273996A1 (en) | 1962-06-01 |
| FR1825M (en) | 1963-05-20 |
| ES273999A1 (en) | 1962-06-01 |
| BE612725A (en) | 1962-07-17 |
| BE612726A (en) | 1962-07-17 |
| ES273997A1 (en) | 1962-06-01 |
| BE612728A (en) | 1962-07-17 |
| FR1837M (en) | 1963-05-27 |
| BE612727A (en) | 1962-07-17 |
| ES273995A1 (en) | 1962-06-01 |
| ES273783A1 (en) | 1962-06-01 |
| FR1836M (en) | 1963-05-27 |
| ES273769A1 (en) | 1962-06-01 |
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