ES2587527T3 - Preparación de 3-[2-[4-((6-fluoro-1,2-bencisoxazol-3-il)-l-piperidinil)-6,7,8,9-tetrahidro-9-hidroxi-2-metil-4H-pirido[1,2 a]-primidin-4-ona (paliperidona) y palmitato de paliperidona - Google Patents
Preparación de 3-[2-[4-((6-fluoro-1,2-bencisoxazol-3-il)-l-piperidinil)-6,7,8,9-tetrahidro-9-hidroxi-2-metil-4H-pirido[1,2 a]-primidin-4-ona (paliperidona) y palmitato de paliperidona Download PDFInfo
- Publication number
- ES2587527T3 ES2587527T3 ES12792315.9T ES12792315T ES2587527T3 ES 2587527 T3 ES2587527 T3 ES 2587527T3 ES 12792315 T ES12792315 T ES 12792315T ES 2587527 T3 ES2587527 T3 ES 2587527T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrido
- tetrahydro
- methyl
- hydroxy
- paliperidone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- VOMKSBFLAZZBOW-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl hexadecanoate Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC3=C(C)N=C4N(C3=O)CCCC4OC(=O)CCCCCCCCCCCCCCC)=NOC2=C1 VOMKSBFLAZZBOW-UHFFFAOYSA-N 0.000 title 1
- PMXMIIMHBWHSKN-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCC(O)C4=NC=3C)=NOC2=C1 PMXMIIMHBWHSKN-UHFFFAOYSA-N 0.000 title 1
- 229960001057 paliperidone Drugs 0.000 title 1
- 229960000635 paliperidone palmitate Drugs 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract 1
- -1 3- (2-chloroethyl) -6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido [1,2-a] pyrimidin-4-one palmitate ester Chemical class 0.000 abstract 1
- JKVUGXRJSYRXFN-UHFFFAOYSA-N 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound OC1CCCN2C(=O)C(CCCl)=C(C)N=C21 JKVUGXRJSYRXFN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Procedimiento para preparar éster de palmitato de 3-(2-cloroetil)-6,7,8,9-tetrahidro-2-metil-9-hidroxi-4Hpirido[ 1,2-a]pirimidin-4-ona de fórmula V**Fórmula** que comprende las etapas de: (i) combinar 3-(2-cloroetil)-6,7,8,9-tetrahidro-2-metil-9-hidroxi-4H-pirido[1,2-a]pirimidin-4-ona de fórmula IV con un derivado de ácido graso en presencia de un derivado de piridina, al menos una base y al menos un disolvente orgánico para obtener una mezcla de reacción y (ii) añadir haluro de ácido a la mezcla de reacción obtenida en la etapa (i) y mantener la mezcla durante un tiempo suficiente para dar el compuesto, éster de palmitato de 3-(2-cloroetil)-6,7,8,9-tetrahidro-2-metil-9- hidroxi-4H-pirido[1,2-a]pirimidin-4-ona de fórmula V:**Fórmula**
Description
Claims (1)
-
imagen1 imagen2 imagen3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1854CH2011 | 2011-05-31 | ||
| INCH18542011 | 2011-05-31 | ||
| PCT/IN2012/000375 WO2012164582A1 (en) | 2011-05-31 | 2012-05-30 | Preparation of 3-[2-[4-((6-fluoro-1, 2-benzisoxazol-3-yl)-l-piperidinyl)-6, 7, 8, 9-tetrahydro-9-hydroxy-2-methyl-4h-pyrido[ 1, 2-a]-pyrimidin-4-one (paliperidone) and paliperidone palmitate. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2587527T3 true ES2587527T3 (es) | 2016-10-25 |
Family
ID=47258492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12792315.9T Active ES2587527T3 (es) | 2011-05-31 | 2012-05-30 | Preparación de 3-[2-[4-((6-fluoro-1,2-bencisoxazol-3-il)-l-piperidinil)-6,7,8,9-tetrahidro-9-hidroxi-2-metil-4H-pirido[1,2 a]-primidin-4-ona (paliperidona) y palmitato de paliperidona |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8940749B2 (es) |
| EP (1) | EP2683717B1 (es) |
| ES (1) | ES2587527T3 (es) |
| PL (1) | PL2683717T3 (es) |
| WO (1) | WO2012164582A1 (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013080220A2 (en) * | 2011-11-28 | 2013-06-06 | Davuluri Rammohan Rao | An improved process for the preparation of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydio-9-hydroxy-2-methyl-4h-pyrido[1,2-a]pyrimidin-4-one. |
| KR101867988B1 (ko) * | 2016-11-02 | 2018-06-15 | 주식회사 엔지켐생명과학 | 팔리페리돈 중간체 및 이를 이용한 팔리페리돈의 제조방법 |
| CN112110914A (zh) * | 2019-06-19 | 2020-12-22 | 上海天慈中商药业有限公司 | 一种帕潘立酮棕榈酸酯的制备方法 |
| CN111440168A (zh) * | 2020-05-22 | 2020-07-24 | 烟台大学 | 6-甲氧基帕利哌酮棕榈酸酯制备方法及应用 |
| CN111533737A (zh) * | 2020-05-22 | 2020-08-14 | 烟台大学 | 4-氟帕利哌酮棕榈酸酯及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5158952A (en) | 1988-11-07 | 1992-10-27 | Janssen Pharmaceutica N.V. | 3-[2-[4-(6-fluoro-1,2-benzisoxozol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9 tetrahydro-9-hydroxy-2-methyl-4H-pyrido [1,2-a]pyrimidin-4-one, compositions and method of use |
| US5254556A (en) * | 1988-11-07 | 1993-10-19 | Janssen Pharmaceutica N.V. | 3-piperidinyl-1,2-benzisoxazoles |
| TW487572B (en) * | 1996-05-20 | 2002-05-21 | Janssen Pharmaceutica Nv | Aqueous suspensions of 9-hydroxyrisperidone fatty acid esters |
| CN101163702B (zh) | 2005-04-25 | 2011-09-07 | 詹森药业有限公司 | 制备无菌的3-[2-[4-(6-氟-1,2-苯并异唑-3-基)-1-哌啶基]乙基]-6,7,8,9-四氢-9-羟基-2-甲基-4H-吡啶并[1,2-a]嘧啶-4-酮棕榈酸酯的方法 |
| US20090048272A1 (en) * | 2007-08-16 | 2009-02-19 | Pratap Reddy Padi | Preparation of paliperidone |
| US20090209757A1 (en) * | 2008-01-10 | 2009-08-20 | Santiago Ini | Processes for the preparation and purification of paliperidone palmitate |
-
2012
- 2012-05-30 ES ES12792315.9T patent/ES2587527T3/es active Active
- 2012-05-30 EP EP12792315.9A patent/EP2683717B1/en not_active Not-in-force
- 2012-05-30 US US13/819,372 patent/US8940749B2/en active Active
- 2012-05-30 WO PCT/IN2012/000375 patent/WO2012164582A1/en not_active Ceased
- 2012-05-30 PL PL12792315.9T patent/PL2683717T3/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2683717T3 (pl) | 2016-11-30 |
| US20140073787A1 (en) | 2014-03-13 |
| WO2012164582A1 (en) | 2012-12-06 |
| US8940749B2 (en) | 2015-01-27 |
| EP2683717B1 (en) | 2016-05-25 |
| EP2683717A4 (en) | 2014-08-27 |
| EP2683717A1 (en) | 2014-01-15 |
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