MD4485C1 - Способ получения 9-бутиламино-3,3-диметил-3,4-дигидроакридин-1(2H)-она гидрохлорида - Google Patents
Способ получения 9-бутиламино-3,3-диметил-3,4-дигидроакридин-1(2H)-она гидрохлорида Download PDFInfo
- Publication number
- MD4485C1 MD4485C1 MDA20150115A MD20150115A MD4485C1 MD 4485 C1 MD4485 C1 MD 4485C1 MD A20150115 A MDA20150115 A MD A20150115A MD 20150115 A MD20150115 A MD 20150115A MD 4485 C1 MD4485 C1 MD 4485C1
- Authority
- MD
- Moldova
- Prior art keywords
- dimethyl
- hydrochloride
- dihydroacridin
- butylamino
- obtaining
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- JCJITGOVWIQPIC-UHFFFAOYSA-N 9-(butylamino)-3,3-dimethyl-2,4-dihydroacridin-1-one;hydrochloride Chemical compound Cl.C1=CC=C2C(NCCCC)=C(C(=O)CC(C)(C)C3)C3=NC2=C1 JCJITGOVWIQPIC-UHFFFAOYSA-N 0.000 title claims abstract description 4
- -1 anthranilic acid nitrile Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 claims abstract description 7
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000004996 alkyl benzenes Chemical class 0.000 claims abstract description 6
- 230000003993 interaction Effects 0.000 claims abstract description 6
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 6
- 230000029936 alkylation Effects 0.000 claims abstract description 5
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 5
- 150000005027 9-aminoacridines Chemical class 0.000 abstract description 5
- AZWDTOZMJCBVKT-UHFFFAOYSA-N CC1(COC=C(C1)NC1=C(C#N)C=CC=C1)C Chemical group CC1(COC=C(C1)NC1=C(C#N)C=CC=C1)C AZWDTOZMJCBVKT-UHFFFAOYSA-N 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- WBMPYOXBHLVYMK-UHFFFAOYSA-N 1-amino-10h-acridin-9-one Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N WBMPYOXBHLVYMK-UHFFFAOYSA-N 0.000 description 12
- 150000002081 enamines Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000012467 final product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000013067 intermediate product Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- MRJDUNSBSYZCCN-UHFFFAOYSA-N 2-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]benzonitrile;hydrochloride Chemical class Cl.C1C(C)(C)CC(=O)C=C1NC1=CC=CC=C1C#N MRJDUNSBSYZCCN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BFCYBMUHOVZFJL-UHFFFAOYSA-N 9-amino-2h-acridin-1-one Chemical class C1=CC=C2C(N)=C(C(=O)CC=C3)C3=NC2=C1 BFCYBMUHOVZFJL-UHFFFAOYSA-N 0.000 description 1
- XJGFWWJLMVZSIG-UHFFFAOYSA-N 9-aminoacridine Chemical compound C1=CC=C2C(N)=C(C=CC=C3)C3=NC2=C1 XJGFWWJLMVZSIG-UHFFFAOYSA-N 0.000 description 1
- BPXINCHFOLVVSG-UHFFFAOYSA-N 9-chloroacridine Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=NC2=C1 BPXINCHFOLVVSG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229960001441 aminoacridine Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003496 anti-amnesic effect Effects 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Изобретение относится к химико-фармацевтической промышленности, а именно к способу получения производного 9-аминоакридина, точнее 9-бутиламино-3,3-диметил-3,4-дигидроакридин-1(2H)-она гидрохлорида.Способ, согласно изобретению, включает стадии взаимодействия нитрила антраниловой кислоты с димедоном, циклизации полученного гидрохлорида замещенного 2-[(5,5-диметил-3-оксациклогекс-1-енил)амино]бензонитрила и алкилирования 9-амино-3,3-диметил-3,4-дигидроакридин-1(H)-она. Способ получения промежуточных соединений осуществляется в среде алкилбензолов.Способ позволяет получить продукт с высоким выходом.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2014150132/04A RU2567388C1 (ru) | 2014-12-10 | 2014-12-10 | Способ получения 9-бутиламино-3,3-диметил-3,4-дигидроакридин-1(2н)-она гидрохлорида |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| MD20150115A0 MD20150115A0 (ru) | 2016-02-29 |
| MD4485B1 MD4485B1 (ru) | 2017-05-31 |
| MD4485C1 true MD4485C1 (ru) | 2017-12-31 |
Family
ID=54537009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20150115A MD4485C1 (ru) | 2014-12-10 | 2015-11-16 | Способ получения 9-бутиламино-3,3-диметил-3,4-дигидроакридин-1(2H)-она гидрохлорида |
Country Status (3)
| Country | Link |
|---|---|
| EA (1) | EA201501038A1 (ru) |
| MD (1) | MD4485C1 (ru) |
| RU (1) | RU2567388C1 (ru) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0179383A2 (en) * | 1984-10-25 | 1986-04-30 | Hoechst-Roussel Pharmaceuticals Incorporated | 9-Amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds, a process for their preparation and their use as medicaments |
| US4695573A (en) * | 1984-10-25 | 1987-09-22 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| EP0268871A1 (en) * | 1986-10-31 | 1988-06-01 | Sumitomo Pharmaceuticals Company, Limited | Quinoline derivatives |
| EP0282959A2 (en) * | 1987-03-17 | 1988-09-21 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 9-amino-tetrahydro-acridines and related compounds, a process for their preparation and their use as medicaments |
| EP0371388A2 (en) * | 1988-11-28 | 1990-06-06 | Fujisawa Pharmaceutical Co., Ltd. | Acridine derivatives |
| US5053513A (en) * | 1990-03-29 | 1991-10-01 | Hoechst-Roussel Pharmaceuticals Incorporated | Method of reducing a carbonyl containing acridine |
| RU2017730C1 (ru) * | 1990-09-17 | 1994-08-15 | Химический факультет МГУ им.М.В.Ломоносова | Способ получения 6-нитро-9-амино-2-этоксиакридина |
| RU2024509C1 (ru) * | 1991-05-07 | 1994-12-15 | Всероссийский научный центр по безопасности биологически активных веществ | Производные 9-аминоакридина или их соли с органическими или неорганическими кислотами, проявляющие психотропную, антиамнестическую и липидрегулирующую активность |
-
2014
- 2014-12-10 RU RU2014150132/04A patent/RU2567388C1/ru not_active IP Right Cessation
-
2015
- 2015-11-16 MD MDA20150115A patent/MD4485C1/ru not_active IP Right Cessation
- 2015-11-19 EA EA201501038A patent/EA201501038A1/ru unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0179383A2 (en) * | 1984-10-25 | 1986-04-30 | Hoechst-Roussel Pharmaceuticals Incorporated | 9-Amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds, a process for their preparation and their use as medicaments |
| US4695573A (en) * | 1984-10-25 | 1987-09-22 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| EP0268871A1 (en) * | 1986-10-31 | 1988-06-01 | Sumitomo Pharmaceuticals Company, Limited | Quinoline derivatives |
| EP0282959A2 (en) * | 1987-03-17 | 1988-09-21 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 9-amino-tetrahydro-acridines and related compounds, a process for their preparation and their use as medicaments |
| EP0371388A2 (en) * | 1988-11-28 | 1990-06-06 | Fujisawa Pharmaceutical Co., Ltd. | Acridine derivatives |
| US5053513A (en) * | 1990-03-29 | 1991-10-01 | Hoechst-Roussel Pharmaceuticals Incorporated | Method of reducing a carbonyl containing acridine |
| RU2017730C1 (ru) * | 1990-09-17 | 1994-08-15 | Химический факультет МГУ им.М.В.Ломоносова | Способ получения 6-нитро-9-амино-2-этоксиакридина |
| RU2024509C1 (ru) * | 1991-05-07 | 1994-12-15 | Всероссийский научный центр по безопасности биологически активных веществ | Производные 9-аминоакридина или их соли с органическими или неорганическими кислотами, проявляющие психотропную, антиамнестическую и липидрегулирующую активность |
Non-Patent Citations (2)
| Title |
|---|
| Деева Э. Г. Сравнительный анализ противогриппозной активности соединений ряда азоло-азинов, флуоренов и акридонов. Автореферат на соискание ученой степени канд. мед. наук, СПб., 2000, p. 16-22 * |
| Ершов Ф.И., Чижов Н.П., Тазулахова Э.Б. Противовирусные средства, СПб., 1993, p. 11-15 * |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2567388C1 (ru) | 2015-11-10 |
| MD20150115A0 (ru) | 2016-02-29 |
| MD4485B1 (ru) | 2017-05-31 |
| EA201501038A1 (ru) | 2016-06-30 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |