UA94931C2 - Способ получения (s)- n-метил-3-(нафтилокси)-3-(2-тиенил)пропиламингидрохлорида (дулоксетина) - Google Patents
Способ получения (s)- n-метил-3-(нафтилокси)-3-(2-тиенил)пропиламингидрохлорида (дулоксетина)Info
- Publication number
- UA94931C2 UA94931C2 UAA200810089A UAA200810089A UA94931C2 UA 94931 C2 UA94931 C2 UA 94931C2 UA A200810089 A UAA200810089 A UA A200810089A UA A200810089 A UAA200810089 A UA A200810089A UA 94931 C2 UA94931 C2 UA 94931C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- naphthyloxy
- thienyl
- propylamine
- dimethyl
- Prior art date
Links
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 title abstract 2
- 229960002866 duloxetine Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- BFFSMCNJSOPUAY-LMOVPXPDSA-N (S)-duloxetine hydrochloride Chemical compound Cl.C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 BFFSMCNJSOPUAY-LMOVPXPDSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 5
- 229960001270 d- tartaric acid Drugs 0.000 abstract 4
- JFTURWWGPMTABQ-SFHVURJKSA-N (3s)-n,n-dimethyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCN(C)C)=CC=CS1 JFTURWWGPMTABQ-SFHVURJKSA-N 0.000 abstract 3
- 239000002253 acid Chemical class 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- JFTURWWGPMTABQ-UHFFFAOYSA-N n,n-dimethyl-3-naphthalen-1-yloxy-3-thiophen-2-ylpropan-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1OC(CCN(C)C)C1=CC=CS1 JFTURWWGPMTABQ-UHFFFAOYSA-N 0.000 abstract 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Способ получения (S)-N-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина формулы I и его фармацевтически приемлемых солей, который включает: а) взаимодействие (RS)-N,N-диметил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина формулы III с оптически активной D-винной кислотой или кислой солью, полученной из D-винной кислоты, с образованием смеси диастереоизомерных солей N,N-диметил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина и D-винной кислоты (2:1), b) выделение соли (S)-N,N-диметил-3-(нафтилокси)-3-(2-тиенил)пропиламин/ D-тартрата (2:1) из смеси диастереоизомерных солей в органическом растворителе, воде или их смеси, и выделение (S)-N,N-диметил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина формулы (S)-(III) путем воздействия неорганической или органической основы, с) деметилирование (S)-N,N-диметил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина путем воздействия алкилхлорформиата формулы ClCOOR (R=C1-C5-алкил, или С6-С12-арил или алкиларил), в частности фенил-, этил- или метилхлороформата, и d) гидролитическое выделение основы дулоксетина формулы I и необязательное преобразование основы в соль пригодной кислотой или в соль слабой основы, в котором, как оптически активное вещество, на стадии (а) используют D-винную кислоту в молярном соотношении 1:2 в отношении вещества формулы III или кислый D-тартрат щелочного металла, или тартрат аммония, или, альтеративно, тартрат алкиламония формулы IV в молярном соотношении 1:1 в отношении вещества формулы III.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20060007A CZ299270B6 (cs) | 2006-01-04 | 2006-01-04 | Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA94931C2 true UA94931C2 (ru) | 2011-06-25 |
Family
ID=38042666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200810089A UA94931C2 (ru) | 2006-01-04 | 2006-12-22 | Способ получения (s)- n-метил-3-(нафтилокси)-3-(2-тиенил)пропиламингидрохлорида (дулоксетина) |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8071791B2 (ru) |
| EP (2) | EP1968965B1 (ru) |
| AT (1) | ATE523503T1 (ru) |
| CZ (1) | CZ299270B6 (ru) |
| EA (1) | EA014559B1 (ru) |
| PL (1) | PL1968965T3 (ru) |
| PT (1) | PT1968965E (ru) |
| UA (1) | UA94931C2 (ru) |
| WO (1) | WO2007076733A2 (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007119116A2 (en) * | 2005-12-12 | 2007-10-25 | Medichem, S.A. | Improved synthesis and preparations of duloxetine salts |
| EP2107057A1 (en) | 2008-04-04 | 2009-10-07 | Ranbaxy Laboratories Limited | Process for the preparation of pure duloxetine hydrochloride |
| CN107429542B (zh) * | 2015-02-24 | 2019-07-05 | 特种油管有限责任公司 | 用于井下钻探装置的可操纵液压喷射喷嘴和导向系统 |
| US20180357365A1 (en) * | 2015-10-02 | 2018-12-13 | Phylagen, Inc. | Product authentication and tracking |
| CN114163415B (zh) * | 2021-12-01 | 2023-03-03 | 珠海润都制药股份有限公司 | 一种盐酸度洛西汀中间体的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR880007433A (ko) | 1986-12-22 | 1988-08-27 | 메리 앤 터커 | 3-아릴옥시-3-치환된 프로판아민 |
| US5362886A (en) * | 1993-10-12 | 1994-11-08 | Eli Lilly And Company | Asymmetric synthesis |
| DE10212301A1 (de) | 2002-03-20 | 2003-10-02 | Bayer Ag | Verfahren zur Herstellung von Aryl-aminopropanolen |
| CN1891683A (zh) | 2002-07-09 | 2007-01-10 | 隆萨股份公司 | N－单取代β－氨基醇的制备方法 |
| GB0229583D0 (en) * | 2002-12-19 | 2003-01-22 | Cipla Ltd | A process for preparing duloxetine and intermediates for use therein |
| GB0410470D0 (en) | 2004-05-11 | 2004-06-16 | Cipla Ltd | Pharmaceutical compound and polymorphs thereof |
| CZ297560B6 (cs) * | 2004-10-26 | 2007-02-07 | Zentiva, A. S. | Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (duloxetinu) |
| CZ297555B6 (cs) * | 2004-10-26 | 2007-02-07 | Zentiva, A. S. | Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (duloxetinu) |
| US20060270861A1 (en) * | 2005-03-14 | 2006-11-30 | Santiago Ini | Process for the preparation of optically active (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine |
| WO2006126213A1 (en) * | 2005-05-24 | 2006-11-30 | Matrix Laboratories Ltd | An improved process for the preparation of duloxetine |
-
2006
- 2006-01-04 CZ CZ20060007A patent/CZ299270B6/cs not_active IP Right Cessation
- 2006-12-22 PT PT06840860T patent/PT1968965E/pt unknown
- 2006-12-22 WO PCT/CZ2006/000096 patent/WO2007076733A2/en not_active Ceased
- 2006-12-22 UA UAA200810089A patent/UA94931C2/ru unknown
- 2006-12-22 US US12/159,905 patent/US8071791B2/en not_active Expired - Fee Related
- 2006-12-22 PL PL06840860T patent/PL1968965T3/pl unknown
- 2006-12-22 EP EP06840860A patent/EP1968965B1/en not_active Not-in-force
- 2006-12-22 AT AT06840860T patent/ATE523503T1/de not_active IP Right Cessation
- 2006-12-22 EA EA200801635A patent/EA014559B1/ru not_active IP Right Cessation
- 2006-12-22 EP EP10000373.0A patent/EP2172464B1/en not_active Not-in-force
-
2011
- 2011-10-05 US US13/253,441 patent/US8207356B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PT1968965E (pt) | 2011-11-10 |
| EA014559B1 (ru) | 2010-12-30 |
| EP2172464A3 (en) | 2010-05-12 |
| WO2007076733A3 (en) | 2007-08-23 |
| EP1968965A2 (en) | 2008-09-17 |
| EP2172464A2 (en) | 2010-04-07 |
| CZ299270B6 (cs) | 2008-06-04 |
| CZ20067A3 (cs) | 2007-07-11 |
| EP1968965B1 (en) | 2011-09-07 |
| US20120029212A1 (en) | 2012-02-02 |
| US8207356B2 (en) | 2012-06-26 |
| WO2007076733A2 (en) | 2007-07-12 |
| PL1968965T3 (pl) | 2011-12-30 |
| ATE523503T1 (de) | 2011-09-15 |
| EP2172464B1 (en) | 2015-08-26 |
| US20080293952A1 (en) | 2008-11-27 |
| US8071791B2 (en) | 2011-12-06 |
| EA200801635A1 (ru) | 2008-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| UA89652C2 (en) | Method of manufacturing (s)-n-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride (duloxetine) | |
| IL184189A0 (en) | Process for the preparation of optically active (s)-(+)-n,n-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine | |
| BRPI0500585A (pt) | Processo para a sìntese de ivabradina e sais de adição desta com um ácido farmaceuticamente aceitável | |
| HUP0203902A2 (hu) | Szubsztituált oxazolidinonok, eljárás az előállításukra, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk | |
| ATE309801T1 (de) | Heteroaryloxy 3-substituierte propanamine s serotonin und norepinephrin reuptake-inhibitoren | |
| BRPI0500480B8 (pt) | processo para a síntese de ivabradina bem como processos para a resolução de amina e para a síntese de composto relacionado com a síntese de ivabradina | |
| MX2011008501A (es) | Compuestos heterociclicos fusionados que contienen nitrogeno y su uso como inhibidores de la produccion de beta-amiloide. | |
| NZ592543A (en) | 4-[2-(2-fluorophenoxymethyl)phenyl]piperidine compounds | |
| WO2007120379A3 (en) | Sulfonanilide analogs as selective aromatase modulators | |
| UA94931C2 (ru) | Способ получения (s)- n-метил-3-(нафтилокси)-3-(2-тиенил)пропиламингидрохлорида (дулоксетина) | |
| WO2007095200A3 (en) | A process for the preparation of (s)-(+)-n,n-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, a duloxetine intermediate | |
| AR058321A1 (es) | Sintesis mejorada y preparaciones de sales de duloxetina | |
| MX2007006081A (es) | Tetrahidroisoquinolinas 4-fenil-sustituidas y uso de las mismas para bloquear la recaptacion de norepinefrina, dopamina y serotonina. | |
| CA2513542A1 (en) | 3-methylamino-1-(2-thienyl)-1-propanone, production and use thereof | |
| MX2007006082A (es) | Tetrahidroisoquinolinas aril- y heteroaril-sustituidas, y uso de las mismas para bloquear la recaptacion de norepinefrina, dopamina y serotonina. | |
| MA32193B1 (fr) | Procede de preparation de combretastatine | |
| ATE396189T1 (de) | Cyanopyrrolhaltige cyclische carbamat- und thiocarbamatbiaryle und verfahren zu deren herstellung | |
| EA201290127A1 (ru) | Способ кристаллизации (s)-n-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина гидрохлорида (дулоксетина) | |
| WO2006103696A3 (en) | Process for preparing levetiracetam and racemization of (r)- and (s)-2-amino butynamide and the corresponding acid derivatives | |
| UA98631C2 (ru) | Способ очистки (s)-n-метил-3-(1-нафтилокси)-3-( 2-тиенил)пропиламина гидрохлорида (дулоксетина) | |
| WO2011033366A3 (en) | Process for the preparation of duloxetine hydrochloride and its precursors | |
| WO2008093360A3 (en) | A process for preparation of (s)-(+)-n-methyl-3(1-naphthyloxy)-3(2-thienyl)propylamine hydrochloride | |
| WO2008021559A3 (en) | Crystalline and amorphous forms of tiagabine | |
| UA89619C2 (ru) | Соединения пиперазина, способ их получения и фармацевтическая композиция, которая их содержит | |
| WO2009130708A3 (en) | Preparation of duloxetine and its salts |