PL411238A1 - Bromides of butanamide 2-cyano-3-oxy-N-substituted derivatives and method for producing them - Google Patents
Bromides of butanamide 2-cyano-3-oxy-N-substituted derivatives and method for producing themInfo
- Publication number
- PL411238A1 PL411238A1 PL411238A PL41123815A PL411238A1 PL 411238 A1 PL411238 A1 PL 411238A1 PL 411238 A PL411238 A PL 411238A PL 41123815 A PL41123815 A PL 41123815A PL 411238 A1 PL411238 A1 PL 411238A1
- Authority
- PL
- Poland
- Prior art keywords
- bromides
- butanamide
- oxy
- cyano
- general formula
- Prior art date
Links
- 150000001649 bromium compounds Chemical class 0.000 title 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- PZKHBPYJZIMLMO-UHFFFAOYSA-N butanamide;hydrobromide Chemical class Br.CCCC(N)=O PZKHBPYJZIMLMO-UHFFFAOYSA-N 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- DJOJFYVMGCYKJV-UHFFFAOYSA-N ethyl 4-cyano-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CC#N DJOJFYVMGCYKJV-UHFFFAOYSA-N 0.000 abstract 1
- FCVMPRQTRCSXKE-UHFFFAOYSA-N methanol propan-2-ol Chemical compound OC.CC(C)O.CC(C)O.CC(C)O FCVMPRQTRCSXKE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QJFMCHRSDOLMHA-UHFFFAOYSA-N phenylmethanamine;hydrobromide Chemical class Br.NCC1=CC=CC=C1 QJFMCHRSDOLMHA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem wynalazku są bromki 2-cyjano-3-oksy-N-podstawione pochodne butanamidu o wzorze ogólnym 1, gdzie X oznacza podstawnik alifatyczny odpowiednio etyl, butyl, heksyl, oktyl, dodecyl. Związki o wzorze ogólnym 1 otrzymuje się w reakcji acylowania odpowiednich bromków 4-[(2-trifenylofosfino)alkiloksy]benzyloaminy, 2-cyjanoacetylooctanem etylu reakcję prowadzi się w środowisku rozpuszczalnika polarnego, w temperaturze pokojowej przez 4 - 6 godzin, stosując proporcje molowe 1 : 1. Po zakończeniu reakcji, wytrącony osad odsącza się i oczyszcza przez krystalizację z mieszaniny metanol-propan-2-ol. Pochodne o wzorze ogólnym 1, gdzie X oznacza podstawnik alifatyczny odpowiednio etyl, butyl, heksyl, oktyl, dodecyl bromku do zastosowania w leczeniu chorób nowotworowych.The present invention relates to 2-cyano-3-oxy-N-substituted butanamide bromides of general formula 1, wherein X is an aliphatic substituent ethyl, butyl, hexyl, octyl and dodecyl, respectively. Compounds of general formula 1 are obtained by the acylation reaction of the corresponding 4 - [(2-triphenylphosphino) alkyloxy] benzylamine bromides, ethyl 2-cyanoacetylacetate, the reaction is carried out in a polar solvent medium at room temperature for 4-6 hours, using molar proportions 1: 1. After completion of the reaction, the precipitate is filtered off and purified by crystallization from a mixture of methanol-propan-2-ol. Derivatives of general formula 1, wherein X is an aliphatic substituent ethyl, butyl, hexyl, octyl and dodecyl bromide, respectively, for use in the treatment of cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL411238A PL229106B1 (en) | 2015-02-11 | 2015-02-11 | Bromides of butanamide 2-cyano-3-oxy-N-substituted derivatives and method for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL411238A PL229106B1 (en) | 2015-02-11 | 2015-02-11 | Bromides of butanamide 2-cyano-3-oxy-N-substituted derivatives and method for producing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL411238A1 true PL411238A1 (en) | 2016-08-16 |
| PL229106B1 PL229106B1 (en) | 2018-06-29 |
Family
ID=56617361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL411238A PL229106B1 (en) | 2015-02-11 | 2015-02-11 | Bromides of butanamide 2-cyano-3-oxy-N-substituted derivatives and method for producing them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL229106B1 (en) |
-
2015
- 2015-02-11 PL PL411238A patent/PL229106B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL229106B1 (en) | 2018-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MX2021006283A (en) | Heteroaromatic derivatives for use as regulator, preparation method therefor and use thereof. | |
| MX2013007490A (en) | Fused aminodihydrothiazine derivatives. | |
| EA201992253A1 (en) | NEW HETEROCYCLIC DERIVATIVES APPLICABLE AS SHP2 INHIBITORS | |
| BR112012010186A2 (en) | heteroaryl derivatives containing n as jak3 kinase inhibitors. | |
| EA201290260A1 (en) | BENZIMIDAZOL-IMIDAZOL DERIVATIVES | |
| MD20160106A2 (en) | Bicyclic-fused heteroaryl or aryl compounds and their use as IRAK4 inhibitors | |
| NO20092770L (en) | Novel aminopyrimidine derivatives as PLK1 inhibitors | |
| PH12022552034A1 (en) | Pyridone derivative having tetrahydropyranyl methyl group | |
| MY160785A (en) | Manufacturing process for pyrimidine derivatives | |
| NZ627250A (en) | Novel nicotinamide derivative or salt thereof | |
| PH12014501719A1 (en) | Pyridone derivatives | |
| EA201591239A1 (en) | SUBSTITUTED PHTHALAZIN-1 (2H) -ONEAL DERIVATIVES AS SELECTIVE POLYMERASE INHIBITORS (ADP-RIBOSE) POLYMERASE-1 | |
| CY1118150T1 (en) | ESTETROL INTERMEDIATE PRODUCTION METHOD | |
| UA105786C2 (en) | Amine addition salts containing hydroxyl and/or carboxylic groups with amino nicotinic acid derivatives as dhodh innhibitors | |
| MY192641A (en) | Novel pyrimidine and pyridine compounds and their usage | |
| MX2017003238A (en) | Method for preparing 2'-o-fucosyllactose. | |
| MX394835B (en) | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds | |
| PH12017501652A1 (en) | Kv1.3 inhibitors and their medical application | |
| MX2018014164A (en) | INTERMEDIATES FOR SYNTHESIS OF BILIAR ACID DERIVATIVES, IN PARTICULAR, OF OBETICOLIC ACID. | |
| NZ742952A (en) | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds | |
| BR112017018580A2 (en) | One kind of MEK kinase inhibitor of p-toluene sulfonate, its crystalline form and method of preparation | |
| MX359069B (en) | Salt and crystal forms of plk-4 inhibitor. | |
| SG10201810361TA (en) | 4'-vinyl substituted nucleoside derivatives as inhibitors of respiratory syncytial virus rna replication | |
| SA516371323B1 (en) | Fluorophenyl pyrazol compounds | |
| NZ735032A (en) | Novel heterocyclic compound, method for preparing the same, and pharmaceutical composition comprising the same |