GB749810A - New derivatives of demethylcolchicine - Google Patents
New derivatives of demethylcolchicineInfo
- 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
Links
- 239000002904 solvent Substances 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- VHIVSZXYLQFNPC-UHFFFAOYSA-N 2-Demethyl-colchicein Natural products C1CC(NC(C)=O)C2=CC(=O)C(O)=CC=C2C2=C1C=C(OC)C(O)=C2OC VHIVSZXYLQFNPC-UHFFFAOYSA-N 0.000 abstract 1
- UXAFRQPVHYZDED-ZZEDUEFDSA-N Colchicoside Chemical class C1([C@@H](NC(C)=O)CCC2=C3)=CC(=O)C(OC)=CC=C1C2=C(OC)C(OC)=C3O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UXAFRQPVHYZDED-ZZEDUEFDSA-N 0.000 abstract 1
- DPOVAJCRYIUTBD-UHFFFAOYSA-N O2-Demethyl-colchicin Natural products C1CC(NC(C)=O)C2=CC(=O)C(OC)=CC=C2C2=C1C=C(OC)C(O)=C2OC DPOVAJCRYIUTBD-UHFFFAOYSA-N 0.000 abstract 1
- 208000020584 Polyploidy Diseases 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- -1 b -hydroxyethyl Chemical group 0.000 abstract 1
- PRGILOMAMBLWNG-UHFFFAOYSA-N colchicceine Natural products C1CC(NC(C)=O)C2=CC(=O)C(O)=CC=C2C2=C1C=C(OC)C(OC)=C2OC PRGILOMAMBLWNG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- VHIVSZXYLQFNPC-AWEZNQCLSA-N n-[(7s)-2,10-dihydroxy-1,3-dimethoxy-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(O)=CC=C1C1=C2C=C(OC)C(O)=C1OC VHIVSZXYLQFNPC-AWEZNQCLSA-N 0.000 abstract 1
- DPOVAJCRYIUTBD-HNNXBMFYSA-N n-[(7s)-2-hydroxy-1,3,10-trimethoxy-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(O)=C1OC DPOVAJCRYIUTBD-HNNXBMFYSA-N 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000002203 pretreatment Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002689 soil Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (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.
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)
| 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 |
-
1954
- 1954-11-03 GB GB31850/54A patent/GB749810A/en not_active Expired
Cited By (2)
| 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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