DK2368871T3 - Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol - Google Patents
Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol Download PDFInfo
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- DK2368871T3 DK2368871T3 DK11004087.0T DK11004087T DK2368871T3 DK 2368871 T3 DK2368871 T3 DK 2368871T3 DK 11004087 T DK11004087 T DK 11004087T DK 2368871 T3 DK2368871 T3 DK 2368871T3
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- carbon
- dimethylamino
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J25/00—Catalysts of the Raney type
- B01J25/02—Raney nickel
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
- C07C225/08—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
- C07C225/10—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings with doubly-bound oxygen atoms bound to carbon atoms not being part of rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (7)
1. Fremgangsmåde til fremstilling af (lR,2R)-3-(3-dimethylamino-l-ethyl-2-methyl-propyl)-phenol, der har formlen (IV)
eller et syreadditionssalt deraf, hvilken fremgangsmåde omfatter de følgende trin: trin (a): at fremstille en forbindelse ifølge formel (II)
eventuelt i form af et syreadditionssalt, ved at reagere en forbindelse ifølge den generelle formel (I)
med ethylmagnesiumbromid eller ethylmagnesiumchlorid i en organisk ether valgt fra gruppen bestående af diethylether, tetrahyd rof uran, 2-methyltetrahydrofuran, tert-butyl-methylether eller en hvilken som helst blanding deraf under Grignard-betingelser; trin (b): at fremstille en forbindelse ifølge den generelle formel (III)
eventuelt i form af et syreadditionssalt, hvorved trin (b) udføres ved (b') at underkaste forbindelsen ifølge den generelle formel (II) til dehydrering og (b") at hydrere den således tilvejebragte forbindelse ifølge den generelle formel (VII)
ved anvendelse af en katalysator i et inert reaktionsmedium under tilstedeværelse af hydrogen; trin (c): at afbeskytte forbindelsen ifølge formel (III) for at tilvejebringe (1 R,2R)-3-(3-dimethylamino-l-ethyl-2-methyl-propyl)-phenol ifølge formel (IV); og eventuelt et trin (d), navnlig at konvertere forbindelse ifølge formel (IV) til et syreadditionssalt, hvor i ovennævnte forbindelser ifølge generelle formel (I), (II) og (III), R står for methyl, benzyl eller tetrahydropyranyl.
2. Fremgangsmåde ifølge krav 1, hvor trin (b) omfatter de følgende trin (b') og (b"), navnlig trin (b'): at underkaste forbindelsen ifølge den generelle formel (II) til en syrekatalyseret dehydreringsreaktion for at give en forbindelse ifølge formel (VII)
trin (b") at underkaste forbindelsen ifølge formel (VII) til en hydreringsreaktion ved heterogen katalyse under tilstedeværelse af hydrogen, hvor katalysatoren er valgt blandt en gruppe bestående af Raney-nikkel, palladium, palladium på carbon, platin, platin på carbon, ruthenium på carbon og rhodium på carbon.
3. Fremgangsmåde ifølge et hvilket som helst af krav 1 eller 2, hvor reaktionen ifølge trin (a) udføres i tetrahydrofuran med ethylmagnesiumchlorid ved en koncentration af ethyl-magnesiumchloriden fra 0,5 M til 2 M.
4. Fremgangsmåde ifølge et hvilket som helst af krav 1 til 3, hvor i forbindelserne ifølge den generelle formele (I), (II) og (III) R står for methyl.
5. Fremgangsmåde ifølge krav 4, hvor i trin (c), reageres forbindelsen ifølge formel (III) med brombrintesyre eller methansulfonsyre og methionin eller diisobutylaluminiumhy-drid i et reaktionsmedium, valgt fra gruppen bestående af diethylether, tetrahydrofuran, toluen, 2-methyltetrahydrofuran, dioxane, tert-butylmethylether og blandinger deraf for at opnå (1 R,2R)-3-(3-dimethylamino-l-ethyl-2-methyl-propyl)-phenol ifølge formel (IV).
6. Fremgangsmåde ifølge et hvilket som helst af krav 1 til 5, hvor den heterogene katalysator i hydreringstrinnet er valgt fra gruppen bestående af Raney-nikkel, palladium, palladium på carbon (1 - 10 vægt%), platin, platin på carbon (1 - 10 vægt%), ruthenium på carbon (1-10 vægt%) og rhodium på carbon (1-10 vægt%).
7. Fremgangsmåde ifølge et hvilket som helst af krav 1 til 5, hvor den heterogene katalysator i hydreringstrinnet er palladium på carbon (1 - 10 vægt%).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06015338 | 2006-07-24 | ||
EP07786260.5A EP2046724B1 (en) | 2006-07-24 | 2007-07-23 | Process for the preparation of (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
Publications (1)
Publication Number | Publication Date |
---|---|
DK2368871T3 true DK2368871T3 (da) | 2017-06-12 |
Family
ID=37198995
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK11004087.0T DK2368871T3 (da) | 2006-07-24 | 2007-07-23 | Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol |
DK17161440.7T DK3210965T3 (da) | 2006-07-24 | 2007-07-23 | Fremgangsmåde til fremstilling af (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
DK07786260.5T DK2046724T3 (da) | 2006-07-24 | 2007-07-23 | Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
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DK17161440.7T DK3210965T3 (da) | 2006-07-24 | 2007-07-23 | Fremgangsmåde til fremstilling af (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
DK07786260.5T DK2046724T3 (da) | 2006-07-24 | 2007-07-23 | Fremgangsmåde til fremstilling af (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
Country Status (27)
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US (7) | US8877974B2 (da) |
EP (4) | EP3210965B1 (da) |
JP (1) | JP5612308B2 (da) |
KR (1) | KR101423996B1 (da) |
CN (1) | CN101495445B (da) |
AU (1) | AU2007278464C1 (da) |
BR (1) | BRPI0714558B8 (da) |
CA (1) | CA2657104C (da) |
CO (1) | CO6160221A2 (da) |
CY (3) | CY1115651T1 (da) |
DK (3) | DK2368871T3 (da) |
ES (4) | ES2901953T3 (da) |
HK (2) | HK1130246A1 (da) |
HR (3) | HRP20211902T1 (da) |
HU (2) | HUE056642T2 (da) |
IL (3) | IL196049A (da) |
LT (2) | LT3210965T (da) |
MX (1) | MX2009000667A (da) |
NO (2) | NO341939B1 (da) |
NZ (1) | NZ573911A (da) |
PL (3) | PL2046724T3 (da) |
PT (3) | PT3210965T (da) |
RU (1) | RU2466124C2 (da) |
SI (3) | SI2368871T1 (da) |
TW (2) | TWI496762B (da) |
WO (1) | WO2008012047A1 (da) |
ZA (1) | ZA200900136B (da) |
Families Citing this family (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI496762B (zh) * | 2006-07-24 | 2015-08-21 | 製備(1r,2r)-3-(3-二甲胺基-1-乙基-2-甲基-丙基)-酚之方法 | |
US20100272815A1 (en) * | 2009-04-28 | 2010-10-28 | Actavis Group Ptc Ehf | Amorphous form of tapentadol hydrochloride |
CN102002065B (zh) * | 2009-09-02 | 2014-09-10 | 上海特化医药科技有限公司 | 他喷他多的制备方法及其中间体 |
US8288592B2 (en) | 2009-09-22 | 2012-10-16 | Actavis Group Ptc Ehf | Solid state forms of tapentadol salts |
IT1397189B1 (it) | 2009-12-01 | 2013-01-04 | Archimica Srl | Nuovo processo per la preparazione di tapentadol e suoi intermedi. |
WO2011080736A1 (en) | 2009-12-29 | 2011-07-07 | Mapi Pharma Hk Limited | Intermediate compounds and processes for the preparation of tapentadol and related compounds |
WO2011080756A1 (en) * | 2009-12-29 | 2011-07-07 | Ind-Swift Laboratories Limited | Process for the preparation of 1-phenyl-3-dimethylaminopropane derivatives |
CA2790519A1 (en) | 2010-03-05 | 2011-09-09 | Actavis Group Ptc Ehf | Improved resolution methods for isolating desired enantiomers of tapentadol intermediates and use thereof for the preparation of tapentadol |
CA2793948A1 (en) | 2010-04-05 | 2011-10-20 | Actavis Group Ptc Ehf | Novel process for preparing highly pure tapentadol or a pharmaceutically acceptable salt thereof |
EP2383255A1 (en) | 2010-04-28 | 2011-11-02 | Lacer, S.A. | New compounds, synthesis and use thereof in the treatment of pain |
ITMI20100924A1 (it) * | 2010-05-21 | 2011-11-22 | Fidia Farmaceutici | Nuovo metodo di sintesi delle due forme enantiomeriche del tapentadol |
EP2582659B1 (en) | 2010-06-15 | 2015-03-11 | Grünenthal GmbH | Process for the preparation of substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds |
IT1401109B1 (it) * | 2010-07-02 | 2013-07-12 | Archimica Srl | Nuovo processo per la preparazione di tapentadol e suoi intermedi. |
WO2012010316A1 (en) | 2010-07-23 | 2012-01-26 | Grünenthal GmbH | Salts or co-crystals of 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
US8853456B2 (en) | 2010-08-16 | 2014-10-07 | Indoco Remedies Limited | Process for the preparation of tapentadol |
CN101948397A (zh) * | 2010-09-07 | 2011-01-19 | 天津泰普药品科技发展有限公司 | 镇痛药他喷他多重要中间体的制备方法 |
CZ2010997A3 (cs) * | 2010-12-30 | 2012-02-08 | Zentiva, K.S. | Zpusob výroby (2R,3R)-N,N-dimethyl-3-(3-hydroxyfenyl)-2-methylpentylaminu (tapentadolu) |
CZ2010995A3 (cs) * | 2010-12-30 | 2012-04-11 | Zentiva, K.S. | Zpusob výroby (2R,3R)-N,N-dimethyl-3-(3-hydroxyfenyl)-2-methylpentylaminu |
EP2545028A4 (en) | 2011-01-27 | 2013-07-03 | Symed Labs Ltd | STEREOSPECIFIC SYNTHESIS OF (-) (2S, 3S) -1-DIMETHYLAMINO-3- (3-METHOXYPHENYL) -2-METHYLPENTAN-3-OLE |
CN102617501A (zh) * | 2011-01-31 | 2012-08-01 | 中国科学院上海药物研究所 | 取代正戊酰胺类化合物、其制备方法及用途 |
CN102206164A (zh) * | 2011-04-11 | 2011-10-05 | 中国药科大学 | 一种他喷他多中间体的制备方法 |
WO2012146978A2 (en) | 2011-04-28 | 2012-11-01 | Actavis Group Ptc Ehf | A novel process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof |
EP2530072A1 (en) | 2011-06-03 | 2012-12-05 | Lacer, S.A. | New compounds, synthesis and use thereof in the treatment of pain |
WO2013105109A1 (en) | 2011-11-09 | 2013-07-18 | Indoco Remedies Limited | Process for the preparation of tapentadol |
US20130150622A1 (en) | 2011-12-12 | 2013-06-13 | Boehringer Ingelheim International Gmbh | Stereoselective synthesis of tapentadol and its salts |
CN102557851B (zh) * | 2011-12-13 | 2014-03-26 | 安徽省新星药物开发有限责任公司 | 一种盐酸他喷他多及其类似物的合成方法 |
WO2013120466A1 (en) | 2012-02-17 | 2013-08-22 | Zentiva, K.S. | A new solid form of tapentadol and a method of its preparation |
EP2674414A1 (en) | 2012-06-15 | 2013-12-18 | Siegfried AG | Method for the preparation of 1-aryl-1-alkyl-3-dialkylaminopropane compounds |
CN103159633B (zh) * | 2012-07-06 | 2015-08-12 | 江苏恩华药业股份有限公司 | 他喷他多的制备方法及用于制备他喷他多的化合物 |
CN102924303B (zh) * | 2012-10-31 | 2013-11-20 | 合肥市新星医药化工有限公司 | 盐酸他喷他多晶型c及其制备方法和应用 |
CN103553940A (zh) * | 2013-11-07 | 2014-02-05 | 南京艾德凯腾生物医药有限责任公司 | 一种新晶型盐酸他喷他多的制备方法 |
WO2015075678A1 (en) | 2013-11-21 | 2015-05-28 | Unimark Remedies Ltd. | A novel process for the preparation of 1-phenyl-3-aminopropane derivatives |
SI3083551T1 (en) | 2013-12-16 | 2018-04-30 | Farma Grs, D.O.O. | CRYSTAL FORM INTERMEDIATE TAPENTADOL |
CN104803861B (zh) * | 2014-01-27 | 2017-05-24 | 上海博邦医药科技有限公司 | 一种合成盐酸他喷他多的方法 |
CZ307492B6 (cs) | 2014-02-04 | 2018-10-17 | Zentiva, K.S. | Pevná forma maleátu tapentadolu a způsob její přípravy |
CN106278915A (zh) * | 2015-05-19 | 2017-01-04 | 重庆圣华曦药业股份有限公司 | 一种制备他喷他多中间体的方法 |
PL3377049T3 (pl) | 2015-11-17 | 2021-06-28 | Msn Laboratories Private Limited | Krystaliczne formy soli tapentadolu i sposób ich wytwarzania |
CN106674029B (zh) * | 2016-12-23 | 2018-08-21 | 四川久凌制药科技有限公司 | 一种他喷他多中间体的制备方法 |
SK812017A3 (sk) | 2017-08-18 | 2019-03-01 | Saneca Pharmaceuticals A. S. | Spôsob prípravy tapentadolu a jeho medziproduktov |
CN112262121A (zh) * | 2018-06-15 | 2021-01-22 | 法尔玛赞公司 | 用于制备他喷他多的新方法 |
EP4116288A1 (en) | 2021-07-08 | 2023-01-11 | KRKA, d.d., Novo mesto | Racemization of (s) and/or (r)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1- one and its mixtures |
EP4269384A1 (en) | 2022-04-26 | 2023-11-01 | KRKA, d.d., Novo mesto | Method for crystallizing tapentadol intermediate, tapentadol intermediate of high purity, method of making tapentadol and tapentadol of high purity |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE107260C (da) | ||||
DE124521C (da) | ||||
AT322534B (de) | 1972-03-16 | 1975-05-26 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen optisch aktiven 1-(4'-amino-3'-halogenphenyl)-2-aminoäthanolen und deren säureadditionssalzen |
US4012456A (en) * | 1974-11-19 | 1977-03-15 | Chaplits Donat N | Method for separation of isobutylene from C4 hydrocarbon fractions |
DD124521A1 (da) | 1976-03-16 | 1977-03-02 | ||
US4276195A (en) * | 1979-12-20 | 1981-06-30 | Iowa State University Research Foundation, Inc. | Converting homogeneous to heterogeneous catalysts |
US6022637A (en) * | 1984-10-23 | 2000-02-08 | Wilson; John T. R. | High temperature battery |
JPH0690934B2 (ja) * | 1987-08-07 | 1994-11-14 | 日本電信電話株式会社 | 二次電池およびその製造方法 |
US5568594A (en) | 1991-04-08 | 1996-10-22 | Kabushiki Kaisha Toshiba | Image forming apparatus with improved ability to emulate other image forming apparatuses |
US6313240B1 (en) | 1993-02-22 | 2001-11-06 | Tosoh Corporation | Process for producing ethylene/α-olefin copolymer |
SG42938A1 (en) | 1993-02-26 | 1997-10-17 | Ciba Geigy Ag | Ferrocenc diphosphines as ligands for homogeneous catalysts |
SG42925A1 (en) * | 1993-10-01 | 1997-10-17 | Ciba Geigy Ag | Fluoroalkyl-substituted ferrocenyl diphosphines as ligands for homogeneous catalysts |
JPH07326372A (ja) | 1994-05-30 | 1995-12-12 | Yuasa Corp | 固体電解質電池 |
DE4426245A1 (de) | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
IL117114A (en) | 1995-02-21 | 2000-02-17 | Montell North America Inc | Components and catalysts for the polymerization ofolefins |
ES2150653T3 (es) * | 1995-02-24 | 2000-12-01 | Novartis Ag | Ferrocenildifosfinas sililadas, ferrocenildifosfinas sililadas unidas a soportes inorganicos o polimeros organicos, asi como complejos metalicos de estas, su obtencion y empleo. |
ATE222932T1 (de) | 1995-02-24 | 2002-09-15 | Novartis Erfind Verwalt Gmbh | An seitenketten von polymeren gebundene diphosphine und deren metall-komplexe |
DE19609847A1 (de) * | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
US6337156B1 (en) * | 1997-12-23 | 2002-01-08 | Sri International | Ion battery using high aspect ratio electrodes |
JPH11345629A (ja) | 1998-03-31 | 1999-12-14 | Canon Inc | 二次電池及びその製造方法 |
JPH11345623A (ja) | 1998-06-01 | 1999-12-14 | Aisin Seiki Co Ltd | 燃料電池装置 |
DE10000311A1 (de) * | 2000-01-05 | 2001-07-12 | Gruenenthal Gmbh | Aminomethyl-Phonyl-Cyclohexanonderivate |
GB0010437D0 (en) * | 2000-04-28 | 2000-06-14 | Darwin Discovery Ltd | Process |
DE10049481A1 (de) | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte C-Cyclohexylmethylamin-Derivate |
JP4951809B2 (ja) | 2000-11-21 | 2012-06-13 | 日油株式会社 | 二次電池用電解質および二次電池 |
JP4777593B2 (ja) * | 2002-11-29 | 2011-09-21 | 株式会社オハラ | リチウムイオン二次電池の製造方法 |
JP4366101B2 (ja) * | 2003-03-31 | 2009-11-18 | キヤノン株式会社 | リチウム二次電池 |
CA2521635A1 (en) * | 2003-04-07 | 2004-10-21 | Solvias Ag | Amine-substituted diphenyldiphosphines and the use thereof in metal complexes for asymmetric syntheses |
DE10326097A1 (de) * | 2003-06-06 | 2005-01-05 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen |
DE10328316A1 (de) * | 2003-06-23 | 2005-01-20 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe |
US7258757B2 (en) | 2004-10-28 | 2007-08-21 | Film Technologies International, Inc. | Method of manufacturing an impact resistant and insulated glass unit composite with solar control and low-E coatings |
AU2006219293A1 (en) | 2005-03-02 | 2006-09-08 | National Institute Of Advanced Industrial Science And Technology | Biosensor coupled with needle |
KR101057284B1 (ko) * | 2005-10-26 | 2011-08-16 | 일라이 릴리 앤드 캄파니 | 선택적 vpac2 수용체 펩티드 작동제 |
TWI496762B (zh) | 2006-07-24 | 2015-08-21 | 製備(1r,2r)-3-(3-二甲胺基-1-乙基-2-甲基-丙基)-酚之方法 |
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