GB749810A - New derivatives of demethylcolchicine - Google Patents

New derivatives of demethylcolchicine

Info

Publication number
GB749810A
GB749810A GB31850/54A GB3185054A GB749810A GB 749810 A GB749810 A GB 749810A GB 31850/54 A GB31850/54 A GB 31850/54A GB 3185054 A GB3185054 A GB 3185054A GB 749810 A GB749810 A GB 749810A
Authority
GB
United Kingdom
Prior art keywords
solvent
formula
demethyl
hydroxyalkyl
atom
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
GB31850/54A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB749810A publication Critical patent/GB749810A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises demethylcolchiceine amides of the formula <FORM:0749810/IV(a)/1> in which R and R1 are hydrogen, alkyl, hydroxyalkyl or together form a ring with the N atom. These are made by reacting HNRR1 with 2-demethylcolchicine ("Substance C") in a solvent, which may be water, an aqueous or anhydrous organic liquid or an excess of the amine reactant. The reaction may take place from room temperature to 100 DEG C., under pressure if necessary, e.g. when using alcohol as solvent. The excess of base is then eliminated, the solvent (if any) removed by distillation or extraction with a non-solvent for the products, and the latter recrystallised from an organic solvent, e.g. alcohol. Examples show the preparation of 2-demethyl-colchiceinamide and the following N-substituted derivatives:-methyl, dimethyl, ethyl, diethyl, b -hydroxyethyl, n-propyl, n-butyl, n-pentyl, n-hexyl; also 2-demethyl-colchiceine morpholide and piperidide. The compounds are the aglucones of the colchicoside derivatives of Specification 739,944.ALSO:Compounds of the formula <FORM:0749810/I/1> in association with a solvent or carrier are used for the modification of karyokinesis and the production of polyploids, especially for spreading on cultivated soils or for the pre-treatment of seeds. In the formula R and R1 are hydrogen, alkyl, hydroxyalkyl or together form a ring with the N atom. Specification 739,944 is referred to.
GB31850/54A 1953-11-12 1954-11-03 New derivatives of demethylcolchicine Expired GB749810A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR749810X 1953-11-12

Publications (1)

Publication Number Publication Date
GB749810A true GB749810A (en) 1956-05-30

Family

ID=9149265

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31850/54A Expired GB749810A (en) 1953-11-12 1954-11-03 New derivatives of demethylcolchicine

Country Status (1)

Country Link
GB (1) GB749810A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1209122B (en) * 1963-05-07 1966-01-20 Roussel Uclaf Process for the preparation of 1-cyano-colchiceinamides
DE1210868B (en) * 1962-12-21 1966-02-17 Roussel Uclaf Process for the preparation of desacetylamino-N-methylcolchiceinamide

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1210868B (en) * 1962-12-21 1966-02-17 Roussel Uclaf Process for the preparation of desacetylamino-N-methylcolchiceinamide
DE1209122B (en) * 1963-05-07 1966-01-20 Roussel Uclaf Process for the preparation of 1-cyano-colchiceinamides

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