AR078975A1 - Procedimiento para producir derivados de piripiropeno - Google Patents
Procedimiento para producir derivados de piripiropenoInfo
- Publication number
- AR078975A1 AR078975A1 ARP100104185A ARP100104185A AR078975A1 AR 078975 A1 AR078975 A1 AR 078975A1 AR P100104185 A ARP100104185 A AR P100104185A AR P100104185 A ARP100104185 A AR P100104185A AR 078975 A1 AR078975 A1 AR 078975A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- group
- acetate
- branched
- crude product
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 4
- 239000012043 crude product Substances 0.000 abstract 4
- 125000004122 cyclic group Chemical group 0.000 abstract 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- -1 acetate butyl Chemical compound 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 238000004090 dissolution Methods 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 2
- 230000008020 evaporation Effects 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Abstract
Reivindicacion 1: Un procedimiento para producir el compuesto C, representado por la formula (1) en la que R representa un alquil-C2-6-carbonilo de cadena lineal, cadena ramificada o cíclico, con la condicion de que cuando la fraccion alquílica en el grupo alquilcarbonilo es del tipo de cadena ramificada o cíclico, R representa alquil-C3-6-carbonilo, caracterizado porque comprende: la acilacion selectiva de grupos hidroxilo en la posicion 1 y en la posicion 11 del compuesto B1, representado por la formula (2) con un agente acilante, en uno a tres pasos, en presencia o ausencia de una base. Reivindicacion 5: El procedimiento de acuerdo con cualquiera de las reivindicaciones 1 a 4, caracterizado porque además comprende como paso para producir el compuesto B1 la hidrolisis de los grupos acilo en la posicion 1, en la posicion 7 y en la posicion 11 del compuesto A1, representado por la formula (3): en la que A1, A7 y A11, que pueden ser iguales o diferentes, representan acetilo o propionilo en presencia de una base. Reivindicacion 16: Un método para aislar y purificar cristales de solvato del compuesto C, representado por la formula (1): en la que R representa un alquiI-C2-6-carbonilo de cadena lineal, cadena ramificada o cíclico, con la condicion de que cuando la fraccion alquílica en el grupo alquilcarbonilo es de un tipo de cadena ramificada o cíclico, R representa alquil-C3-6-carbonilo, caracterizado porque comprende: (a) la extraccion de una solucion de reaccion que contiene el compuesto C, con un disolvente orgánico seleccionado de entre el grupo constituido por acetato de metilo, acetato de etilo, acetato de butilo, tolueno, etilbenceno, clorobenceno, cloroformo, diclorometano, éter dietílico, éter diisopropílico, tetrahidrofurano y dioxano, y la concentracion del extracto después del secado o sin secado previo; (b) la evaporacion hasta sequedad de la solucion de reaccion que contiene el compuesto C para obtener un producto bruto y luego la disolucion del producto bruto en un disolvente orgánico seleccionado de entre el grupo constituido por acetato de metilo, acetato de etilo, acetato de butilo, tolueno, etilbenceno, clorobenceno, cloroformo, diclorometano, éter dietílico, éter diisopropílico, tetrahidrofurano, dioxano, metanol y etanol, a temperatura ambiente o calentando; o (c) la evaporacion hasta sequedad de la solucion de reaccion que contiene el compuesto C para obtener un producto bruto, la disolucion del producto bruto en un disolvente orgánico seleccionado de entre el grupo constituido por acetato de metilo, acetato de etilo, acetato de butilo, tolueno, etilbenceno, clorobenceno, cloroformo, diclorometano, éter dietílico, éter diisopropílico, tetrahidrofurano, dioxano, metanol y etanol, a temperatura ambiente o calentando, y la adicion de un mal disolvente, seleccionado de entre el grupo constituido por heptano, hexano y ciclohexano, a la solucion.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010044416 | 2010-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR078975A1 true AR078975A1 (es) | 2011-12-14 |
Family
ID=43528310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100104185A AR078975A1 (es) | 2010-03-01 | 2010-11-11 | Procedimiento para producir derivados de piripiropeno |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8853414B2 (es) |
| EP (1) | EP2542555B1 (es) |
| JP (1) | JP5717752B2 (es) |
| KR (1) | KR101787789B1 (es) |
| CN (1) | CN102947312B (es) |
| AR (1) | AR078975A1 (es) |
| BR (1) | BR112012021911B8 (es) |
| CA (1) | CA2791660C (es) |
| CR (1) | CR20120487A (es) |
| DK (1) | DK2542555T3 (es) |
| EC (1) | ECSP12012203A (es) |
| ES (1) | ES2607191T3 (es) |
| IL (1) | IL221651A (es) |
| MX (1) | MX2012010173A (es) |
| NZ (1) | NZ602719A (es) |
| RU (1) | RU2578605C2 (es) |
| TW (1) | TWI504602B (es) |
| UA (1) | UA111151C2 (es) |
| WO (1) | WO2011108155A1 (es) |
| ZA (1) | ZA201207335B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8853413B2 (en) | 2009-05-13 | 2014-10-07 | Meiji Seika Pharma Co., Ltd. | Process for producing pyripyropene derivatives |
| UA111151C2 (uk) | 2010-03-01 | 2016-04-11 | Мейдзі Сейка Фарма Ко., Лтд. | Спосіб одержання похідних пірипіропену |
| WO2012035015A2 (en) * | 2010-09-14 | 2012-03-22 | Basf Se | Composition containing a pyripyropene insecticide and an adjuvant |
| US9861104B2 (en) * | 2012-03-12 | 2018-01-09 | Basf Se | Method for producing an aqueous suspension concentrate formulation of a pyripyropene insecticide |
| AU2014206958B2 (en) * | 2013-01-16 | 2017-08-10 | Basf Se | Method for preparing a pyripyropene compound |
| JP6215355B2 (ja) * | 2013-01-25 | 2017-10-18 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 水性懸濁製剤の調製方法 |
| US10150777B2 (en) | 2013-03-28 | 2018-12-11 | Basf Se | Production of pyripyropenes from dry biomass |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5192887A (en) * | 1991-09-23 | 1993-03-09 | Emerson Electric Co. | Starting multi-speed motors at a low speed connection |
| JP3233476B2 (ja) | 1992-10-22 | 2001-11-26 | 社団法人北里研究所 | Ｆｏ−１２８９物質およびその製造法 |
| JPH08239385A (ja) | 1995-03-03 | 1996-09-17 | Kitasato Inst:The | Ｆｏ−１２８９物質およびその製造法 |
| JP3725198B2 (ja) | 1995-03-27 | 2005-12-07 | 社団法人北里研究所 | ピリピロペン誘導体 |
| JPH08269065A (ja) | 1995-04-03 | 1996-10-15 | Kitasato Inst:The | ピリピロペン誘導体 |
| KR100522446B1 (ko) | 2003-01-07 | 2005-10-18 | 한국생명공학연구원 | 아실 코에이:콜레스테롤 아실 트란스퍼라제의 저해활성을갖는 화합물 또는 그 염을 유효성분으로 하는 살충제 |
| BRPI0511621A (pt) | 2004-05-28 | 2008-01-02 | Speedel Experimenta Ag | compostos orgánicos |
| TWI388282B (zh) * | 2005-06-01 | 2013-03-11 | Meiji Seika Pharma Co Ltd | 害蟲控制劑 |
| US7491738B2 (en) | 2005-06-01 | 2009-02-17 | Meiji Seika Kaisha, Ltd. | Pest control agents |
| JP2008050997A (ja) | 2006-08-24 | 2008-03-06 | Matsushita Electric Ind Co Ltd | 密閉型電動圧縮機 |
| ATE539080T1 (de) | 2006-11-30 | 2012-01-15 | Meiji Seika Pharma Co Ltd | Schädlingsbekämpfungsmittel |
| JP4488033B2 (ja) | 2007-02-06 | 2010-06-23 | ソニー株式会社 | 偏光素子及び液晶プロジェクター |
| CN101821272B (zh) | 2007-08-13 | 2013-03-27 | 明治制果药业株式会社 | 生产pyripyropene衍生物的方法及其生产中间体 |
| US9434739B2 (en) | 2007-12-21 | 2016-09-06 | Meiji Seika Pharma Co., Ltd. | Systemic insecticide |
| US8853413B2 (en) | 2009-05-13 | 2014-10-07 | Meiji Seika Pharma Co., Ltd. | Process for producing pyripyropene derivatives |
| UA111151C2 (uk) | 2010-03-01 | 2016-04-11 | Мейдзі Сейка Фарма Ко., Лтд. | Спосіб одержання похідних пірипіропену |
-
2010
- 2010-10-11 UA UAA201211289A patent/UA111151C2/uk unknown
- 2010-11-10 EP EP10788151.8A patent/EP2542555B1/en active Active
- 2010-11-10 CN CN201080065119.7A patent/CN102947312B/zh active Active
- 2010-11-10 NZ NZ602719A patent/NZ602719A/en unknown
- 2010-11-10 BR BR112012021911A patent/BR112012021911B8/pt active IP Right Grant
- 2010-11-10 RU RU2012141555/04A patent/RU2578605C2/ru active
- 2010-11-10 WO PCT/JP2010/070414 patent/WO2011108155A1/en not_active Ceased
- 2010-11-10 CA CA2791660A patent/CA2791660C/en active Active
- 2010-11-10 US US13/581,857 patent/US8853414B2/en active Active
- 2010-11-10 JP JP2012540182A patent/JP5717752B2/ja active Active
- 2010-11-10 KR KR1020127025488A patent/KR101787789B1/ko active Active
- 2010-11-10 ES ES10788151.8T patent/ES2607191T3/es active Active
- 2010-11-10 DK DK10788151.8T patent/DK2542555T3/da active
- 2010-11-10 MX MX2012010173A patent/MX2012010173A/es active IP Right Grant
- 2010-11-11 TW TW099139126A patent/TWI504602B/zh active
- 2010-11-11 AR ARP100104185A patent/AR078975A1/es active IP Right Grant
-
2012
- 2012-08-27 IL IL221651A patent/IL221651A/en active IP Right Grant
- 2012-09-26 CR CR20120487A patent/CR20120487A/es unknown
- 2012-10-01 ZA ZA2012/07335A patent/ZA201207335B/en unknown
- 2012-10-01 EC ECSP12012203 patent/ECSP12012203A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR101787789B1 (ko) | 2017-10-18 |
| US8853414B2 (en) | 2014-10-07 |
| RU2578605C2 (ru) | 2016-03-27 |
| IL221651A (en) | 2017-05-29 |
| JP2013521224A (ja) | 2013-06-10 |
| WO2011108155A1 (en) | 2011-09-09 |
| DK2542555T3 (da) | 2017-01-02 |
| EP2542555B1 (en) | 2016-09-21 |
| TW201139447A (en) | 2011-11-16 |
| BR112012021911B8 (pt) | 2022-08-02 |
| CA2791660C (en) | 2020-09-22 |
| TWI504602B (zh) | 2015-10-21 |
| JP5717752B2 (ja) | 2015-05-13 |
| KR20130040180A (ko) | 2013-04-23 |
| NZ602719A (en) | 2015-01-30 |
| ES2607191T3 (es) | 2017-03-29 |
| BR112012021911A2 (pt) | 2015-09-29 |
| ECSP12012203A (es) | 2013-06-28 |
| US20130060042A1 (en) | 2013-03-07 |
| RU2012141555A (ru) | 2014-04-10 |
| ZA201207335B (en) | 2014-01-29 |
| UA111151C2 (uk) | 2016-04-11 |
| BR112012021911B1 (pt) | 2021-06-08 |
| AU2010347354B2 (en) | 2016-09-01 |
| CN102947312B (zh) | 2015-05-27 |
| CR20120487A (es) | 2013-01-11 |
| EP2542555A1 (en) | 2013-01-09 |
| CN102947312A (zh) | 2013-02-27 |
| MX2012010173A (es) | 2012-10-03 |
| CA2791660A1 (en) | 2011-09-09 |
| AU2010347354A1 (en) | 2012-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration |