ES273769A1 - Process for the preparation of new -carboline-carboxylic acid amide derivatives - Google Patents

Process for the preparation of new -carboline-carboxylic acid amide derivatives

Info

Publication number
ES273769A1
ES273769A1 ES0273769A ES273769A ES273769A1 ES 273769 A1 ES273769 A1 ES 273769A1 ES 0273769 A ES0273769 A ES 0273769A ES 273769 A ES273769 A ES 273769A ES 273769 A1 ES273769 A1 ES 273769A1
Authority
ES
Spain
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
Application number
ES0273769A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
JR Geigy AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of ES273769A1 publication Critical patent/ES273769A1/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-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.
ES0273769A 1961-01-18 1962-01-16 Process for the preparation of new -carboline-carboxylic acid amide derivatives Expired ES273769A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US8339061A 1961-01-18 1961-01-18

Publications (1)

Publication Number Publication Date
ES273769A1 true ES273769A1 (en) 1962-06-01

Family

ID=22177990

Family Applications (6)

Application Number Title Priority Date Filing Date
ES0273769A Expired ES273769A1 (en) 1961-01-18 1962-01-16 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273999A Expired ES273999A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273997A Expired ES273997A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273783A Expired ES273783A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273995A Expired ES273995A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273996A Expired ES273996A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives

Family Applications After (5)

Application Number Title Priority Date Filing Date
ES0273999A Expired ES273999A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273997A Expired ES273997A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273783A Expired ES273783A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273995A Expired ES273995A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -carboline-carboxylic acid amide derivatives
ES0273996A Expired ES273996A1 (en) 1961-01-18 1962-01-17 Process for the preparation of new -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)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1084256A (en) * 1963-11-06
NZ194747A (en) * 1979-08-29 1988-11-29 Schering Ag 9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives
FR2487829A2 (en) * 1979-12-07 1982-02-05 Science Union & Cie NOVEL SUBSTITUTED IMINO ACIDS, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS AN ENZYME INHIBITOR
JPS57123180A (en) * 1980-12-17 1982-07-31 Schering Ag 3-substituted beta-carboline, manufacture and psychotropic drug containing same
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
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
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
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
DE4436190A1 (en) * 1994-10-10 1996-04-11 Gerhard Prof Dr Bringmann Halogenated β-carboline derivatives, process for their preparation and use of these substances for inhibiting the respiratory chain
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
DK2691394T3 (en) * 2011-03-28 2017-08-28 Sjt Molecular Res S L RELATIONSHIPS FOR TREATMENT OF METABOLIC SYNDROME
EP3405469B1 (en) * 2016-01-22 2021-05-05 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

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
GB975835A (en) 1964-11-18
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

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