MX2020000408A - Proceso para la preparacion y purificacion de misoprostol. - Google Patents
Proceso para la preparacion y purificacion de misoprostol.Info
- Publication number
- MX2020000408A MX2020000408A MX2020000408A MX2020000408A MX2020000408A MX 2020000408 A MX2020000408 A MX 2020000408A MX 2020000408 A MX2020000408 A MX 2020000408A MX 2020000408 A MX2020000408 A MX 2020000408A MX 2020000408 A MX2020000408 A MX 2020000408A
- Authority
- MX
- Mexico
- Prior art keywords
- sup
- sub
- general formula
- group
- cuprate
- Prior art date
Links
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 title abstract 2
- 229960005249 misoprostol Drugs 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- -1 vinyl stannane Chemical compound 0.000 abstract 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 229910000080 stannane Inorganic materials 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Proceso para la preparación de los compuestos de fórmula general I, entre ellos, misoprostol (ver Fórmulas) donde R representa un grupo alquilo C1-4 de cadena lineal o ramificada por acoplamiento con cuprato del cuprato de vinilo de fórmula general II preparado haciendo reaccionar el vinil estannano de fórmula general III con haluro de cobre CuX y alquillitio R1Li (ver Fórmula) en donde: R2 representa H o un grupo protector de alcohol que puede contener un átomo de silicio, como, por ejemplo, un grupo trimetilsililo, trietilsililo, terc-butildimetilsililo, o un grupo alquilo de cadena cíclica o abierta que contiene un átomo de oxígeno, como, por ejemplo, un grupo tetrahidropiranilo, metoximetilo o etoximetilo; X significa I, Br, grupo CN, SCN, OSO2CF3, R1 representa un grupo alquilo C1-6,n >2, si R2 no es un átomo de hidrógeno, n>3, si R2 es un átomo de hidrógeno, y la enona protegida de la fórmula general IV (ver Fórmula) donde R3 representa un grupo THP o trialquilsililo y el significado de R es como se ha definido anteriormente toma parte en la reacción del cuprato de una manera que a.) el exceso del alquillitio, que se aplica en comparación con el yoduro de Cu(I). en el caso de R2 ? H en una relación molar 2 a 2.4, en el caso de R2 = H en una relación molar 3 a 3.4, se descompone antes de la reacción de acoplamiento de II y IV, b.) los grupos protectores del compuesto resultante de la fórmula general V (ver Fórmula) donde los significados de R, R2 y R3 son como se han definido anteriormente, se eliminan, el compuesto obtenido de la fórmula general I se purifica por cromatografía.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1700308A HU231185B1 (hu) | 2017-07-11 | 2017-07-11 | Eljárás Misoprostol előállítására és tisztítására |
| PCT/EP2018/067560 WO2019011668A1 (en) | 2017-07-11 | 2018-06-29 | PROCESS FOR THE PREPARATION AND PURIFICATION OF MISOPROSTOL |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2020000408A true MX2020000408A (es) | 2020-08-06 |
Family
ID=89992488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2020000408A MX2020000408A (es) | 2017-07-11 | 2018-06-29 | Proceso para la preparacion y purificacion de misoprostol. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10759734B2 (es) |
| EP (1) | EP3652142B1 (es) |
| JP (1) | JP7292255B2 (es) |
| KR (1) | KR102606739B1 (es) |
| CN (1) | CN111148730B (es) |
| BR (1) | BR112020000452B1 (es) |
| ES (1) | ES2897902T3 (es) |
| HU (2) | HU231185B1 (es) |
| MX (1) | MX2020000408A (es) |
| TW (1) | TWI786149B (es) |
| WO (1) | WO2019011668A1 (es) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US904820A (en) * | 1908-07-13 | 1908-11-24 | Joseph M Vail | Rail-clamp. |
| US3965143A (en) | 1974-03-26 | 1976-06-22 | G. D. Searle & Co. | 16-Oxygenated prostanoic acid derivatives |
| US4777275A (en) * | 1987-06-09 | 1988-10-11 | G. D. Searle & Co. | Process of preparing higher order cuprate complexes |
| US4904820A (en) * | 1987-06-09 | 1990-02-27 | G. D. Searle & Co. | Process for substituting a hydrocarbon group |
| US4952710A (en) * | 1988-10-07 | 1990-08-28 | G. D. Searle & Co. | Cyclopenteneheptenoic acid derivatives and method of preparation thereof |
| US5055604A (en) | 1990-04-17 | 1991-10-08 | G. D. Searle & Co. | Process for preparing prostaglandin analogs using organozirconium compounds |
| US5817694A (en) | 1992-06-08 | 1998-10-06 | New Pharma International Corp. | 16-methyl-11,16-dihydroxy-9-oxoprost-2,13-dien-1-oic acid and derivatives |
| US5618959A (en) | 1995-03-10 | 1997-04-08 | Vivus Incorporated | Process for preparing prostaglandin E1, E2 and analogs thereof using furylcopper reagents |
| US5684177A (en) * | 1996-05-17 | 1997-11-04 | Torcan Chemical Ltd. | Misoprostol |
| JP4153998B2 (ja) * | 1996-11-14 | 2008-09-24 | 第一ファインケミカル株式会社 | プロスタグランジン類の製造方法 |
| US8519178B2 (en) | 2009-06-22 | 2013-08-27 | Johnson Matthey Public Limited Company | Method for the purification of prostaglandins |
| CN106349138A (zh) * | 2011-06-02 | 2017-01-25 | 奇诺因私人有限公司 | 用于制备前列腺素酰胺的新的方法 |
| CN105254657B (zh) | 2014-07-10 | 2018-06-15 | 台湾神隆股份有限公司 | 金属催化不对称1,4-共轭加成反应产生前列腺素和前列腺素类似物 |
-
2017
- 2017-07-11 HU HU1700308A patent/HU231185B1/hu unknown
-
2018
- 2018-06-29 WO PCT/EP2018/067560 patent/WO2019011668A1/en unknown
- 2018-06-29 JP JP2020501347A patent/JP7292255B2/ja active Active
- 2018-06-29 CN CN201880046087.2A patent/CN111148730B/zh active Active
- 2018-06-29 BR BR112020000452-9A patent/BR112020000452B1/pt active IP Right Grant
- 2018-06-29 MX MX2020000408A patent/MX2020000408A/es unknown
- 2018-06-29 US US16/630,125 patent/US10759734B2/en active Active
- 2018-06-29 ES ES18735563T patent/ES2897902T3/es active Active
- 2018-06-29 EP EP18735563.1A patent/EP3652142B1/en active Active
- 2018-06-29 KR KR1020207003719A patent/KR102606739B1/ko active IP Right Grant
- 2018-06-29 HU HUE18735563A patent/HUE056431T2/hu unknown
- 2018-07-09 TW TW107123642A patent/TWI786149B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112020000452A2 (pt) | 2020-07-21 |
| KR20200033876A (ko) | 2020-03-30 |
| HUE056431T2 (hu) | 2022-02-28 |
| RU2020106128A3 (es) | 2021-11-11 |
| RU2020106128A (ru) | 2021-08-11 |
| ES2897902T3 (es) | 2022-03-03 |
| EP3652142A1 (en) | 2020-05-20 |
| US10759734B2 (en) | 2020-09-01 |
| JP7292255B2 (ja) | 2023-06-16 |
| KR102606739B1 (ko) | 2023-11-24 |
| JP2020526559A (ja) | 2020-08-31 |
| US20200165186A1 (en) | 2020-05-28 |
| EP3652142B1 (en) | 2021-09-01 |
| BR112020000452B1 (pt) | 2023-03-14 |
| HUP1700308A1 (en) | 2019-01-28 |
| WO2019011668A1 (en) | 2019-01-17 |
| CN111148730A (zh) | 2020-05-12 |
| TW201920093A (zh) | 2019-06-01 |
| TWI786149B (zh) | 2022-12-11 |
| HU231185B1 (hu) | 2021-07-28 |
| CN111148730B (zh) | 2023-02-17 |
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