AR080656A1 - Sintesis de magnolol y sus compuestos analogos, y composicion farmaceutica - Google Patents
Sintesis de magnolol y sus compuestos analogos, y composicion farmaceuticaInfo
- Publication number
- AR080656A1 AR080656A1 ARP110100579A ARP110100579A AR080656A1 AR 080656 A1 AR080656 A1 AR 080656A1 AR P110100579 A ARP110100579 A AR P110100579A AR P110100579 A ARP110100579 A AR P110100579A AR 080656 A1 AR080656 A1 AR 080656A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- organic solvent
- reaction
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 17
- VVOAZFWZEDHOOU-UHFFFAOYSA-N magnolol Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 title 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 239000003960 organic solvent Substances 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003223 protective agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/52—Preparation of compounds having groups by reactions producing groups by substitution of halogen only
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Reivindicacion 1: Un método para producir un compuesto de la formula (1) donde R representa H, un alquilo, un fenilo sustituido o no sustituido; o sus sales oralmente o farmacéuticamente aceptables, caracterizado porque comprende: (a) reaccion de un compuesto de formula (2) con bromuro en un solvente orgánico para obtener un compuesto de formula (3); (b) reaccion del compuesto de formula (3) con MOM-Cl en un solvente orgánico en la presencia de una base orgánica para obtener un compuesto de formula (4); (c) reaccion del compuesto de formula (4) con R-CH=CH-CH2-Br, donde R se define como se indico anteriormente, en un solvente orgánico con magnesio y bromuro de etilo para obtener un compuesto de formula (5); y (d) conversion del compuesto de formula (5) con un agente des-protector adecuado en un solvente orgánico para obtener un compuesto de formula (1); y (e) opcionalmente, convertir el compuesto de formula (1) a sus sales oralmente o farmacéuticamente aceptables. Reivindicacion 13: Un método para producir el compuesto de formula (5) caracterizado porque comprende la reaccion de un compuesto de la formula (4) con R-CH=CH-CH2-Br, donde R representa H, alquilo, un fenilo sustituido o no sustituido, en un solvente orgánico por una cantidad de tiempo suficiente para obtener un compuesto de la formula (5), y opcionalmente convirtiendo el compuesto de la formula (5) a un compuesto de la formula (1). Reivindicacion 21: Una composicion caracterizada porque comprende un vehículo aceptable oral farmacéuticamente, y una cantidad efectiva de un anti-bacterial de un compuesto de formula (1) preparado de acuerdo al método de la reivindicacion 1 donde R representa H, alquilo, un fenilo sustituido o no sustituido.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2010/025378 WO2011106003A1 (en) | 2010-02-25 | 2010-02-25 | Synthesis of magnolol and its analogue compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR080656A1 true AR080656A1 (es) | 2012-04-25 |
Family
ID=42028117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110100579A AR080656A1 (es) | 2010-02-25 | 2011-02-24 | Sintesis de magnolol y sus compuestos analogos, y composicion farmaceutica |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8519197B2 (es) |
| EP (1) | EP2539310B1 (es) |
| JP (1) | JP2013520495A (es) |
| CN (1) | CN102884035B (es) |
| AR (1) | AR080656A1 (es) |
| AU (1) | AU2010346597B2 (es) |
| BR (1) | BR112012020603A2 (es) |
| CA (1) | CA2789140C (es) |
| DK (1) | DK2539310T3 (es) |
| ES (1) | ES2507615T3 (es) |
| MX (1) | MX2012009817A (es) |
| MY (1) | MY162466A (es) |
| PH (1) | PH12012501619A1 (es) |
| PL (1) | PL2539310T3 (es) |
| RU (1) | RU2510938C1 (es) |
| SG (1) | SG183120A1 (es) |
| TW (1) | TWI438185B (es) |
| WO (1) | WO2011106003A1 (es) |
| ZA (1) | ZA201206020B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112013015973B1 (pt) | 2010-12-21 | 2018-12-11 | Colgate-Palmolive Company | bifenóis halogenados como agentes antibacterianos. |
| US9414587B2 (en) | 2011-12-15 | 2016-08-16 | Cologne-Palmolive Company | Solubilized magnolol analogs |
| CN104023700B (zh) | 2011-12-15 | 2015-10-07 | 高露洁-棕榄公司 | 含溶解的厚朴酚类似物和ppg-1-peg-9月桂二醇醚的口腔护理或清洁剂组合物 |
| US9000231B2 (en) | 2011-12-20 | 2015-04-07 | Colgate-Palmolive Company | Processes for making magnolol and derivatives thereof |
| JP2015500875A (ja) | 2011-12-20 | 2015-01-08 | コルゲート・パーモリブ・カンパニーＣｏｌｇａｔｅ−Ｐａｌｍｏｌｉｖｅ Ｃｏｍｐａｎｙ | マグノロール類似体を製造するための方法 |
| MX351329B (es) | 2013-01-23 | 2017-10-11 | Colgate Palmolive Co | Proceso para elaborar derivados de magnolol. |
| JP2015007054A (ja) * | 2014-07-24 | 2015-01-15 | コルゲート・パーモリブ・カンパニーＣｏｌｇａｔｅ−Ｐａｌｍｏｌｉｖｅ Ｃｏｍｐａｎｙ | マグノロールおよびその類似体化合物の合成 |
| MX389172B (es) * | 2015-10-23 | 2025-03-20 | Colgate Palmolive Co | Sintesis mejorada de honokiol. |
| CN109053387B (zh) * | 2018-09-19 | 2021-07-09 | 九江学院 | 一种厚朴酚的合成方法 |
| WO2020126347A1 (en) | 2018-12-18 | 2020-06-25 | Unilever N.V. | An antimicrobial composition |
| CN115581690A (zh) * | 2021-07-05 | 2023-01-10 | 北京红惠新医药科技有限公司 | 厚朴酚或和厚朴酚的芳环氨基取代衍生物在用于制备抗心肌缺血药物中的应用、药物组合物 |
| CN116139115A (zh) * | 2021-11-19 | 2023-05-23 | 北京红惠新医药科技有限公司 | 厚朴酚和/或和厚朴酚芳环氨基取代类衍生物的抗低氧/缺氧损伤用途及药物组合物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0544488T3 (da) * | 1991-11-25 | 1998-04-06 | Lilly Co Eli | Substituerede phenylphenolleukotrienantagonister |
| US6544409B2 (en) * | 2001-05-16 | 2003-04-08 | Petroleo Brasileiro S.A. - Petrobras | Process for the catalytic oxidation of sulfur, nitrogen and unsaturated compounds from hydrocarbon streams |
| CN1147286C (zh) * | 2001-07-18 | 2004-04-28 | 广州美晨股份有限公司 | 一种中药牙膏 |
| CN1723011A (zh) * | 2002-06-25 | 2006-01-18 | Wm·雷格利Jr·公司 | 含有厚朴提取物的口气清新和口腔清洁产品 |
| US20060140885A1 (en) * | 2004-12-29 | 2006-06-29 | Abdul Gaffar | Method of reducing oral tissue inflammation using magnolia extract |
| WO2008098056A2 (en) * | 2007-02-06 | 2008-08-14 | Epix Pharmaceuticals, Inc. | High relaxivity chelates |
-
2010
- 2010-02-25 US US13/577,627 patent/US8519197B2/en active Active
- 2010-02-25 AU AU2010346597A patent/AU2010346597B2/en not_active Ceased
- 2010-02-25 WO PCT/US2010/025378 patent/WO2011106003A1/en not_active Ceased
- 2010-02-25 JP JP2012554971A patent/JP2013520495A/ja active Pending
- 2010-02-25 RU RU2012140748/04A patent/RU2510938C1/ru not_active IP Right Cessation
- 2010-02-25 SG SG2012056404A patent/SG183120A1/en unknown
- 2010-02-25 PL PL10705965T patent/PL2539310T3/pl unknown
- 2010-02-25 ES ES10705965.1T patent/ES2507615T3/es active Active
- 2010-02-25 BR BR112012020603A patent/BR112012020603A2/pt active Search and Examination
- 2010-02-25 CN CN201080064851.2A patent/CN102884035B/zh not_active Expired - Fee Related
- 2010-02-25 PH PH1/2012/501619A patent/PH12012501619A1/en unknown
- 2010-02-25 MX MX2012009817A patent/MX2012009817A/es active IP Right Grant
- 2010-02-25 CA CA2789140A patent/CA2789140C/en not_active Expired - Fee Related
- 2010-02-25 EP EP10705965.1A patent/EP2539310B1/en active Active
- 2010-02-25 MY MYPI2012003487A patent/MY162466A/en unknown
- 2010-02-25 DK DK10705965.1T patent/DK2539310T3/da active
-
2011
- 2011-02-24 AR ARP110100579A patent/AR080656A1/es unknown
- 2011-02-24 TW TW100106113A patent/TWI438185B/zh not_active IP Right Cessation
-
2012
- 2012-08-10 ZA ZA2012/06020A patent/ZA201206020B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2789140C (en) | 2015-01-27 |
| BR112012020603A2 (pt) | 2017-07-11 |
| MX2012009817A (es) | 2012-09-12 |
| WO2011106003A1 (en) | 2011-09-01 |
| AU2010346597B2 (en) | 2013-09-19 |
| MY162466A (en) | 2017-06-15 |
| PL2539310T3 (pl) | 2015-01-30 |
| US8519197B2 (en) | 2013-08-27 |
| EP2539310B1 (en) | 2014-07-16 |
| EP2539310A1 (en) | 2013-01-02 |
| ES2507615T3 (es) | 2014-10-15 |
| CN102884035A (zh) | 2013-01-16 |
| US20120302647A1 (en) | 2012-11-29 |
| TWI438185B (zh) | 2014-05-21 |
| DK2539310T3 (da) | 2014-10-20 |
| PH12012501619A1 (en) | 2014-09-24 |
| CA2789140A1 (en) | 2011-09-01 |
| JP2013520495A (ja) | 2013-06-06 |
| SG183120A1 (en) | 2012-09-27 |
| AU2010346597A1 (en) | 2012-08-23 |
| HK1180297A1 (en) | 2013-10-18 |
| CN102884035B (zh) | 2016-01-20 |
| RU2510938C1 (ru) | 2014-04-10 |
| RU2012140748A (ru) | 2014-03-27 |
| TW201141823A (en) | 2011-12-01 |
| ZA201206020B (en) | 2014-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |